Essential Oils: Extraction, Characterization and Applications 0323917402, 9780323917407

Table of contents :
Front Cover
Essential Oils: Extraction, Characterization and Applications
Copyright
Contents
Contributors
Chapter 1: Essential oils in plants: Plant physiology, the chemical composition of the oil, and natural variation of the ...
1.1. Introduction
1.2. Phytochemistry of different essential oils
1.2.1. Major phytochemicals in the plant-based essential oils
1.2.1.1. Terpenes
1.2.1.2. Alpha-pinene
1.2.1.3. Steroids
1.2.1.4. Tannins
1.2.1.5. Flavonoids
1.2.1.6. Glycosides
1.2.1.7. Alkaloids
1.2.1.8. Phenols
1.2.1.9. Coumarin
1.2.1.10. Saponins
1.3. Natural variation of the oils (chemotaxonomy and environmental effects, etc.)
1.4. Extraction methods of essential oils
1.4.1. Conventional extraction methods
1.4.1.1. Hydrodistillation
1.4.1.2. Steam distillation
1.4.1.3. Hydrodiffusion
1.4.1.4. Solvent extraction
1.4.2. Innovative extraction methods
1.4.2.1. Supercritical fluid extraction
1.4.2.2. Subcritical extraction liquid
1.4.2.3. Solvent-free microwave extraction
1.5. Characterization of all essential oil
1.6. Applications of all essential oils
1.6.1. Antioxidant
1.6.2. Antiinflammatory
1.6.3. Antihyperpigmentation
1.6.4. Antidiabetic
1.6.5. Antimicrobial
1.6.6. Antiviral
1.6.7. Anticancer
1.6.8. Cardioprotective
1.6.9. Neuroprotective
1.6.10. Hepatoprotective
1.7. Safety concerns
1.8. Conclusion
References
Further reading
Chapter 2: Extraction and analysis of essential oils: Extraction methods used at laboratory and industrial level and chem ...
2.1. Introduction
2.2. Extraction, isolation, and purification methods of essential oils at laboratory level
2.2.1. Innovatory extraction methods
2.2.1.1. Supercritical fluid extraction (ScFE)
2.2.1.2. Subcritical liquid extraction (SLE)
2.2.1.3. Solvent-free microwave extraction (SFME)
2.2.1.4. Pulsed electric field extraction (PEFE)
2.2.2. Isolation and purification techniques of essential oils at laboratory level
2.2.2.1. High-performance thin layer chromatography (HPTLC)
2.2.2.2. Optimum performance laminar chromatography (OPLC)
2.3. Extraction, isolation, and purification methods used for essential oils at the industrial level
2.3.1. Extraction methods
2.3.1.1. Water distillation (hydrodistillation)
2.3.1.2. Steam distillation
2.3.1.3. Solvent extraction
2.3.2. Isolation and purification techniques of essential oils used at the industrial level
2.3.2.1. Thin layer chromatography (TLC)
2.3.2.2. Column chromatography (CC)
2.3.2.3. High-performance liquid chromatography (HPLC)
2.4. Chemical transformation
2.4.1. Supercritical fluid chromatography (SFC)
2.4.2. Simulated moving bed chromatography (SMBC)
2.4.3. Ultrasound-assisted extraction (UAE)
2.4.4. Microwave-assisted extraction (MAE)
2.4.5. Enzyme-assisted extraction (EAE)
2.5. Conclusion
References
Chapter 3: Importance of essential oils and current trends in use of essential oils (aroma therapy, agrofood, and medicin ...
3.1. Introduction
3.2. Aromatherapy
3.2.1. Eucalyptus
3.2.2. Lavender
3.2.3. Lemon
3.2.4. Rosemary
3.2.5. Tea tree
3.3. Agrofood uses
3.3.1. EOs as green pesticides
3.3.2. Utilization of EOs as food preservatives
3.3.3. Presence of EOs in packaging materials
3.4. Medicinal uses
3.4.1. Antioxidant
3.4.2. Antibacterial
3.4.3. Antifungal
3.4.4. Anticancer
3.4.5. Antiinflammatory
3.4.6. Antiviral
3.4.7. Antidiabetic
3.4.8. Antiprotozoal
3.4.9. Anxiolytic potential
3.4.10. Anticholinesterase potential
3.5. Economic importance
3.6. Current trends
3.6.1. Food preservation
3.6.2. Medicinal uses
3.6.2.1. Antibacterial properties
3.6.2.2. Antifungal properties
3.7. Future perspective
3.8. Conclusion
References
Chapter 4: Lavender essential oil: Nutritional, compositional, and therapeutic insights
4.1. Introduction
4.2. Current status
4.3. Biochemical profile
4.4. Extraction techniques
4.5. Structural and nutritional characterization
4.6. Chemistry and their properties
4.6.1. Linalool
4.6.2. Linalyl acetate
4.6.3. Eucalyptol
4.6.4. Carvacrol
4.6.5. α-Terpineol
4.7. Therapeutic potential
4.7.1. Aromatherapy
4.7.2. Antidepressant
4.7.3. Antimicrobial
4.7.4. Antioxidant
4.7.5. Cardioprotective
4.7.6. Antiinflammatory
4.7.7. Digestive system
4.7.8. Anticancer
4.7.9. Antihair fall
4.8. Applications
4.8.1. Application in agrofood
4.8.2. Nonfood applications
4.9. Safety, toxicity, and regulation
4.9.1. Toxicity
4.9.2. Legislations
4.9.3. Trade, storage stability, and transportation
4.10. Conclusion
References
Chapter 5: Peppermint essential oil
5.1. Introduction
5.2. Production and composition
5.3. Extraction techniques
5.3.1. Steam distillation
5.3.2. Hydrodistillation
5.3.3. Solvent extraction
5.3.4. Microwave assisted extraction
5.3.5. Supercritical fluid extraction
5.3.6. Other methods
5.4. Characterization of peppermint essential oil components
5.5. Properties of peppermint essential oils
5.5.1. Antimicrobial properties
5.6. Applications of peppermint essential oil
5.6.1. Relieves pain
5.6.2. Cures irritable bowel syndrome (IBS)
5.7. Toxicity associated with usage of peppermint essential oil
5.8. Conclusion and future perspective
References
Chapter 6: Sandalwood essential oil
6.1. Introduction
6.2. Comparative account on sandalwood essential oil
6.2.1. Santalum album (Indian sandalwood)
6.2.2. Santalum spicatum (Western Australian sandalwood)
6.2.3. Santalum paniculatum (Hawaiian sandalwood)
6.2.4. Santalum yasi
6.2.5. Santalum austrocaledonicum
6.2.6. Santalum lanceolatum
6.2.7. Santalum macgregorii
6.3. Methods of extraction of sandalwood essential oil
6.4. Therapeutic benefits of sandalwood essential oil
6.5. Production and composition of sandalwood essential oil
6.6. Safety, toxicity, and regulation of sandalwood essential oil
6.7. Trade and storage stability of sandalwood essential oil
6.8. Current understanding and prospects
6.9. Conclusion
References
Chapter 7: Jasmine essential oil: Production, extraction, characterization, and applications
7.1. Introduction
7.1.1. The jasmine plants
7.1.2. Major species
7.2. Production and composition
7.2.1. Production and market trends
7.2.2. Planting and propagation
7.2.3. Growth and development
7.2.4. Husbandry
7.2.5. Harvesting and handling
7.2.6. Composition and physicochemical properties
7.3. Extraction techniques
7.3.1. Steam distillation
7.3.2. The steam distillation process
7.3.3. Super critical fluid extraction (SFE)
7.3.4. Supercritical fluid extraction process
7.3.5. Analysis of jasmine essential oils
7.4. Characterization of jasmine essential oils using NMR spectroscopy
7.5. Chemistry and properties
7.6. Applications of jasmine essential oil: Pharmacological, agrofood, and nonfood applications
7.6.1. Antimicrobial potential
7.6.2. Antioxidant and anticancer potential
7.6.3. Acaricidal potential
7.6.4. Xanthine oxidase inhibitory activity
7.6.5. Food preservation potential
7.7. Safety, toxicity, and regulations
7.8. Trade, storage stability, and transport
7.9. Conclusion
References
Chapter 8: Citrus essential oil (grapefruit, orange, lemon)
8.1. Introduction
8.2. Extraction and characterization of citrus essential oils (CEOs)
8.2.1. Cold pressing (CP) method
8.2.2. Solvent extraction (SE) method
8.2.3. Steam distillation (SD) method
8.2.4. Hydrodistillation (HD) method
8.2.5. Ultrasound-assisted extraction (UAE)
8.2.6. Microwave-assisted extraction (MAE) method
8.2.7. Microwave-assisted hydrodistillation (MAHD) method
8.2.8. Ionic liquid-based microwave-assisted extraction (MAE-IL) method
8.2.9. Microwave-assisted hydrodiffusion and gravity method (MHG)
8.2.10. Microwave accelerated distillation (MAD) method
8.2.11. Supercritical fluid extraction
8.2.12. Enzyme assisted extraction (EAE)
8.3. Composition of citrus essential oils (CEOs)
8.4. Applications of citrus essential oils
8.4.1. Antioxidant activity
8.4.2. Antiinflammatory activity
8.4.3. Antitumor assay
8.4.4. Antiprotozoal activity
8.4.5. Antimicrobial and antifungal activity
8.4.6. Insecticidal activity
8.5. Future concerns and perspectives
8.6. Conclusion
References
Chapter 9: Eucalyptus essential oils
9.1. Introduction
9.2. Eucalyptus essential oil history
9.3. Some important types of eucalyptus essential oil
9.3.1. Eucalyptus globulus (blue gum)
9.3.2. Eucalyptus polybractea (blue mallee)
9.3.3. Eucalyptus radiata (Eucalyptus radiata)
9.3.4. Eucalyptus citridora (lemon eucalyptus)
9.4. Production and composition
9.4.1. Production
9.4.2. Composition
9.4.2.1. E. oleosa essential oils
9.4.2.2. E. oleosa stems essential oil
9.4.2.3. E. oleosa leaves essential oil
9.4.2.4. Essential oil of E. oleosa fruits
9.5. Techniques
9.5.1. Extraction strategies
9.5.2. Hydro-distillation
9.5.3. Steam distillation
9.5.4. Vacuum distillation
9.5.5. Supercritical fluid extraction (SFE)
9.5.6. Subcritical-water extraction (SWE)
9.5.7. Microwave-assisted essential oil extraction (MAEOE)
9.6. Characterization and identification of essential oil components by techniques like NMR-13C
9.7. Eucalyptus essential oil chemistry and properties
9.7.1. Chemical makeup
9.8. Essential oil yield
9.9. Functional applications of Eucalyptus essential oil
9.9.1. Aromatherapy
9.9.2. Antimicrobial properties
9.9.3. Antifungal activity
9.9.4. Insecticidal activity
9.9.5. Antioxidant activity
9.10. Eucalyptus essential oils application in pharmacological, agro food, and nonfood products
9.10.1. Eucalyptus oils use in pharmaceuticals
9.10.2. Anticancer
9.10.3. Antidiabetic
9.10.4. Antibacterial
9.11. Eucalyptus essential oils use in agro-industry
9.11.1. Eucalyptus essential oils use as insect repellent
9.11.2. Development of herbicides
9.11.3. Eucalyptus essential oils application in nonfood products
9.12. Eucalyptus essential oils as additives in active food packaging
9.12.1. Impact of eucalyptus oil addition on the in vitro antioxidant properties
9.13. Eucalyptus oils use in the fragrance industry
9.13.1. Eucalyptus oils use in air fresheners
9.13.2. Eucalyptus essential oils benefits for skin
9.13.3. Eucalyptus essential oil used in a humidifier
9.14. Safety, toxicity and regulation
9.14.1. Safety
9.14.1.1. Safety assessment of cosmetics ingredients
9.14.1.2. Safety assessment of food ingredients
9.14.1.3. Safety assessment of drug ingredients
9.14.1.4. Other
9.14.2. Toxicity and regulation
9.14.2.1. Oral ingestion of Eucalyptus globulus leaf oil
9.14.2.2. Inhalation of essential leaf oil
9.15. Trade, storage stability and transport of eucalyptus essential oil
9.15.1. World-wide trade and markets for eucalyptus oil
9.15.2. Storage stability of eucalyptus essential oil
9.15.3. Transport of eucalyptus essential oil
9.16. Conclusion
References
Chapter 10: Essential oils from Apiaceae family (parsley, lovage, and dill)
10.1. Introduction
10.2. Factors influencing essential oil production of parsley, dill, and lovage
10.2.1. Factors influencing essential oil production of parsley
10.2.2. Factors influencing essential oil production of dill
10.2.3. Factors influencing essential oil production of lovage
10.3. Extraction techniques of parsley, dill, and lovage essential oil
10.3.1. Extraction techniques for parsley essential oil
10.3.2. Extraction techniques for dill essential oil
10.3.3. Extraction techniques for lovage essential oil
10.4. Chemical profile of parsley, dill, and lovage essential oil
10.4.1. Chemical profile of parsley essential oil
10.4.2. Chemical profile of dill essential oil
10.4.3. Chemical profile of lovage essential oil
10.5. Bioactivity of parsley, dill, and lovage essential oil
10.5.1. Antioxidant activity of parsley, dill, and lovage essential oil
10.5.2. Antimicrobial activity of parsley, dill, and lovage essential oil
10.6. Applications of parsley, dill, and lovage essential oil
10.6.1. Pharmacological applications of parsley, dill, and lovage essential oil
10.6.1.1. Pharmacological applications of parsley essential oil
10.6.1.2. Pharmacological applications of dill essential oil
10.6.1.3. Pharmacological applications of lovage essential oil
10.6.2. Food applications of parsley, dill, and lovage essential oil
10.6.3. Non-food applications of parsley, dill, and lovage essential oil
10.7. Safety and toxicity of parsley, dill, and lovage essential oil
10.8. Trade and regulation of parsley, dill, and lovage essential oil
10.9. Conclusion
References
Chapter 11: Essential oils from Lamiaceae family (rosemary, thyme, mint, basil)
11.1. Chemical composition of essential oils
11.2. Lamiaceae family
11.2.1. Essential oil of Lamiaceae family
11.3. Composition of basil, mint, rosemary, and thyme oil
11.4. Extraction techniques
11.5. Safety, toxicity, and regulation of basil, mint, rosemary, and thyme oil
11.6. Storage stability of basil, mint, thyme, and rosemary oil
11.7. Applications of essential oils of basil, mint, rosemary, and thyme
11.7.1. Pharmacological
11.7.2. Agro-food
11.7.3. Non-food applications
11.8. Conclusion
References
Chapter 12: Clove oil
12.1. Introduction
12.2. Botanical description
12.3. Impurities and their removal from clove oil
12.3.1. Phospholipids
12.3.2. Free fatty acids
12.4. Oil extraction by enzymes
12.4.1. Super critical fluid extraction (SCF)
12.5. Lipid oxidation in clove oil
12.6. Fortification of foods with clove oil
12.7. Future applications of clove oil
12.7.1. Bakery and table margarine
12.7.2. Dairy whitener tea/coffee whitener
12.7.3. Whipped cream dairy and nondairy versions
12.7.4. Use of stearin and olein fractions of clove oil in ice cream and frozen desserts
12.7.5. Mayonnaise
12.8. Summary of some clinical trials of polyunsaturated fatty acids
References
Chapter 13: Ginger essential oil: Chemical composition, extraction, characterization, pharmacological activities, and app ...
13.1. Introduction
13.2. Productions of GEO
13.3. Chemical composition and yield of GEO
13.3.1. Effect of geographical location on chemical components and yield of GEO
13.3.2. Effect of maturity and variety on chemical components and yield of GEO
13.3.3. Effect of drying methods on chemical components and yield of GEO
13.3.4. Effect of extraction method on chemical components and yield of GEO
13.4. Extraction methods of GEO
13.4.1. Conventional methods of extraction
13.4.1.1. Hydro-distillation
13.4.1.2. Steam distillation
13.4.1.3. Solvent extraction/liquid-liquid extraction
13.4.1.4. Soxhlet extraction
13.4.2. Advanced methods of extraction of GEO
13.4.2.1. Supercritical CO2 extraction
13.4.2.2. Subcritical water extraction
13.4.2.3. Solvent-free microwave extraction
13.4.2.4. Microwave-assisted hydro-distillation
13.4.2.5. Microwave hydro-diffusion and gravity
13.5. Analytical method for characterization of GEO
13.5.1. GC-MS analysis of GEO
13.5.2. 13C NMR analysis of GEO
13.6. Pharmacological activities of GEO
13.6.1. Antioxidant activity
13.6.2. Anti-inflammatory and analgesic effects
13.6.3. Antimicrobial activity
13.6.4. Anticancer activity
13.6.5. Neuroprotection
13.6.6. Anti-obesity activity
13.6.7. Antidiabetic activity
13.6.8. Bronchodilatory effects
13.6.9. Anti-ulcer effects
13.6.10. Immunomodulatory effects
13.6.11. Other pharmacological activities
13.7. Applications of GEO
13.8. Safety, toxicity, and regulation
13.9. Trade, storage stability and transport
13.10. Conclusion
References
Chapter 14: Cinnamon essential oil
14.1. Introduction
14.2. Production and composition of cinnamon EO
14.2.1. Extraction techniques
14.3. Characterization of cinnamon essential oil
14.4. Health benefits of cinnamon essential oil
14.4.1. Antiinflammatory
14.4.2. Antitumor and anticancer
14.4.3. Antidiabetic
14.4.4. Antioxidant activity
14.5. Application of cinnamon essential oil in food and nonfood industries
14.6. Conclusion
References
Chapter 15: Nutmeg essential oil
15.1. Introduction
15.2. Botanical aspects
15.3. Essential oil production
15.4. Composition of nutmeg
15.5. Extraction of nutmeg essential oil
15.6. Uses and applications
15.6.1. Applications of nutmeg and nutmeg oil in food industry
15.7. Safety, toxicity, and regulation of nutmeg essential oil
15.8. Conclusion
References
Chapter 16: Rosewood essential oil
16.1. Introduction
16.2. Production of rosewood essential oil
16.3. Composition of rosewood oil
16.4. Extraction of rosewood oil
16.4.1. Conventional extraction methods
16.4.1.1. Steam distillation
16.4.1.2. Hydro-distillation
16.4.1.3. Hydro-diffusion
16.4.1.4. Solvent extraction
16.4.2. Innovative extraction technology
16.4.2.1. Supercritical fluid extraction
16.4.2.2. Microwave-assisted extraction
16.4.2.3. Ultrasonic assisted extraction
16.5. Chemical characterization
16.6. Characteristics of rosewood
16.7. Applications of rosewood essential oil
16.7.1. Pharmacological applications
16.7.2. Food applications
16.8. Safety and toxicity of rosewood essential oils
16.9. Storage stability
16.10. Trade of rosewood oil
16.11. Conclusion
References
Chapter 17: Juniper essential oil: An overview of bioactive compounds and functional aspects
17.1. Introduction
17.2. Production and composition
17.3. Extraction techniques (distillation)
17.4. Applications
17.5. Health claims
17.5.1. Antioxidant activity
17.5.2. Hepatoprotective activity
17.5.3. Antiinflammatory activity
17.5.4. Antidiabetic activity
17.5.5. Antihyperlipidemic activity
17.5.6. Analgesic activity
17.5.7. Antibacterial activity
17.5.8. Antimicrobial activity
17.5.9. Antifungal activity
17.5.10. Antimalarial activity
17.5.11. Anticataleptic activity
17.5.12. Neuroprotective activity
17.6. Conclusion
References
Chapter 18: Patchouli essential oil
18.1. Introduction
18.2. Production and composition
18.2.1. Adulteration and contamination
18.2.2. Odor of patchouli essential oil
18.3. Extraction techniques
18.3.1. Steam distillation
18.3.2. Hydrodistillation
18.3.3. Microwave hydrodistillation
18.3.4. Microwave air-hydrodistillation
18.3.5. Solvent-free microwave extraction
18.3.6. Ultrasonic assisted solvent extraction
18.4. Characterization
18.4.1. Two-dimensional gas chromatography (2D-GC)
18.4.2. Chiral GC
18.4.3. Chromatographic fingerprint of patchouli oil
18.5. Chemistry and properties
18.6. Applications
18.6.1. Aromatherapy
18.6.2. Pharmacological activities
18.6.2.1. Gastrointestinal protective effect
18.6.2.2. Effect on intestinal microecology
18.6.2.3. Antidiarrheal effect
18.6.2.4. Antiemetic effect
18.6.2.5. Antidiabetic effect
18.6.2.6. Antihypertensive effect
18.6.2.7. Effect on ischemia/reperfusion (I/R) injury
18.6.2.8. Antioxidant effect
18.6.2.9. Antiinflammatory effect
18.6.2.10. Antitumor effect
18.6.2.11. Analgesic effect
18.6.2.12. Immunoregulatory effect
18.6.2.13. Antimicrobial effect
18.6.2.14. Insecticidal effect
18.7. Safety, toxicity, and regulation
18.8. Trade, storage stability, and transport
18.9. Conclusion
References
Chapter 19: Clary sage essential oil
19.1. Introduction
19.2. Clary sage oil production and chemical composition
19.3. Extraction techniques (distillation)
19.3.1. Distillation
19.3.1.1. Steam distillation
19.3.1.2. Hydrodistillation
19.3.1.3. Hydrodiffusion
19.3.2. Solvent extraction
19.3.2.1. Supercritical carbon dioxide
19.3.2.2. Subcritical water
19.3.3. Solvent-free microwave extraction (SFME)
19.3.4. Combination methods
19.4. Characterization of essential oil components
19.5. Chemistry and properties
19.6. Applications
19.6.1. Pharmacological
19.6.1.1. Antianxiolytic
19.6.1.2. Significance in women health
19.6.1.3. Antibacterial
19.6.1.4. Antifungal
19.6.1.5. Antiviral
19.6.1.6. Antidepressant and stress-relieving properties
19.6.1.7. Cytotoxic
19.6.1.8. Antioxidant
19.6.1.9. Antiinflammatory
19.6.1.10. Antidiabetic
19.6.2. Agro-food
19.6.3. Nonfood
19.6.3.1. Perfumery
19.6.3.2. Cosmetics
19.6.3.3. Wound dressings and smart packaging
19.7. Safety, toxicity and regulation
19.8. Trade, storage, stability, and transport
19.9. Conclusion
References
Chapter 20: Tea tree essential oil
20.1. Introduction
20.2. Phytochemistry of tea tree EO
20.3. Extraction of tea tree EO
20.3.1. Steam distillation extraction
20.3.1.1. Pretreatment of raw material for steam distillation
20.3.2. Steam distillation process
20.3.3. Modifications in steam distillation process
20.3.4. Other extraction methods
20.4. Applications of tea tree essential oils
20.4.1. Pharmacological applications
20.4.1.1. Antimicrobial applications
20.4.1.2. Antiinflammatory properties
20.4.1.3. Antioxidant
20.4.1.4. Anticancer
20.4.1.5. Acaridical properties
20.4.1.6. Topical, herbal and therapeutic applications
20.4.2. Agrofood applications
20.4.3. Nonfood applications
20.5. Safety concerns
20.6. Conclusions
References
Index
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ESSENTIAL OILS

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ESSENTIAL OILS Extraction, Characterization and Applications Edited by

GULZAR AHMAD NAYIK MOHAMMAD JAVED ANSARI

Academic Press is an imprint of Elsevier 125 London Wall, London EC2Y 5AS, United Kingdom 525 B Street, Suite 1650, San Diego, CA 92101, United States 50 Hampshire Street, 5th Floor, Cambridge, MA 02139, United States The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, United Kingdom Copyright © 2023 Elsevier Inc. All rights reserved. No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording, or any information storage and retrieval system, without permission in writing from the publisher. Details on how to seek permission, further information about the Publisher’s permissions policies and our arrangements with organizations such as the Copyright Clearance Center and the Copyright Licensing Agency, can be found at our website: www.elsevier.com/permissions. This book and the individual contributions contained in it are protected under copyright by the Publisher (other than as may be noted herein). Notices Knowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary. Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility. To the fullest extent of the law, neither the Publisher nor the authors, contributors, or editors, assume any liability for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions, or ideas contained in the material herein. ISBN: 978-0-323-91740-7 For information on all Academic Press publications visit our website at https://www.elsevier.com/books-and-journals

Publisher: Nikki Levy Acquisitions Editor: Nina Bandeira Editorial Project Manager: Clark Espinosa Production Project Manager: Bharatwaj Varatharajan Cover Designer: Vicky Pearson Esser Typeset by STRAIVE, India

Contents

3. Importance of essential oils and current trends in use of essential oils (aroma therapy, agrofood, and medicinal usage)

Contributors ix 1. Essential oils in plants: Plant physiology, the chemical composition of the oil, and natural variation of the oils (chemotaxonomy and environmental effects, etc.)

Ajay Sharma, Khushbu Gumber, Apurba Gohain, Tejasvi Bhatia, Harvinder Singh Sohal, Vishal Mutreja, and Garima Bhardwaj

3.1 Introduction 53 3.2 Aromatherapy 55 3.3 Agrofood uses 58 3.4 Medicinal uses 64 3.5 Economic importance 69 3.6 Current trends 75 3.7 Future perspective 76 3.8 Conclusion 77 References 78

Sipper Khan, Amna Sahar, Tayyaba Tariq, Aysha Sameen, and Farwa Tariq

1.1 Introduction 1 1.2 Phytochemistry of different essential oils 2 1.3 Natural variation of the oils (chemotaxonomy and environmental effects, etc.) 8 1.4 Extraction methods of essential oils 16 1.5 Characterization of all essential oil 20 1.6 Applications of all essential oils 21 1.7 Safety concerns 26 1.8 Conclusion 27 References 28 Further reading 36

4. Lavender essential oil: Nutritional, compositional, and therapeutic insights Farhan Saeed, Muhammad Afzaal, Muhammad Ahtisham Raza, Amara Rasheed, Muzzamal Hussain, Gulzar Ahmad Nayik, and Mohammad Javed Ansari

4.1 Introduction 85 4.2 Current status 86 4.3 Biochemical profile 87 4.4 Extraction techniques 87 4.5 Structural and nutritional characterization 89 4.6 Chemistry and their properties 90 4.7 Therapeutic potential 92 4.8 Applications 96 4.9 Safety, toxicity, and regulation 97 4.10 Conclusion 98 References 99

2. Extraction and analysis of essential oils: Extraction methods used at laboratory and industrial level and chemical analysis Muhammad Modassar Ali Nawaz Ranjha, Syeda Mahvish Zahra, Shafeeqa Irfan, Bakhtawar Shafique, Rabia Noreen, Umar Farooq Alahmad, Saba Liaqat, and Saba Umar

2.1 Introduction 37 2.2 Extraction, isolation, and purification methods of essential oils at laboratory level 38 2.3 Extraction, isolation, and purification methods used for essential oils at the industrial level 41 2.4 Chemical transformation 44 2.5 Conclusion 49 References 49

5. Peppermint essential oil Jaspreet Kaur and Kamaljit Kaur

5.1 Introduction 103 5.2 Production and composition 104

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5.3 Extraction techniques 107 5.4 Characterization of peppermint essential oil components 110 5.5 Properties of peppermint essential oils 111 5.6 Applications of peppermint essential oil 112 5.7 Toxicity associated with usage of peppermint essential oil 115 5.8 Conclusion and future perspective 116 References 116

6. Sandalwood essential oil Tridip Boruah, Prastuti Parashar, Chayanika Ujir, Suraj Kr. Dey, Gulzar Ahmad Nayik, Mohammad Javed Ansari, and Amir Sasan Mozaffari Nejad

6.1 Introduction 121 6.2 Comparative account on sandalwood essential oil 123 6.3 Methods of extraction of sandalwood essential oil 128 6.4 Therapeutic benefits of sandalwood essential oil 129 6.5 Production and composition of sandalwood essential oil 131 6.6 Safety, toxicity, and regulation of sandalwood essential oil 135 6.7 Trade and storage stability of sandalwood essential oil 137 6.8 Current understanding and prospects 140 6.9 Conclusion 140 References 141

7. Jasmine essential oil: Production, extraction, characterization, and applications Mohammad Makeri and Aliyu Salihu

7.1 7.2 7.3 7.4 7.5 7.6

7.7 7.8

Introduction 147 Production and composition 149 Extraction techniques 155 Characterization of jasmine essential oils using NMR spectroscopy 160 Chemistry and properties 161 Applications of jasmine essential oil: Pharmacological, agrofood, and nonfood applications 165 Safety, toxicity, and regulations 170 Trade, storage stability, and transport 171

7.9 Conclusion 172 References 173

8. Citrus essential oil (grapefruit, orange, lemon) Gurpreet Kaur, Kamalpreet Kaur, and Preeti Saluja

8.1 Introduction 179 8.2 Extraction and characterization of citrus essential oils (CEOs) 180 8.3 Composition of citrus essential oils (CEOs) 195 8.4 Applications of citrus essential oils 198 8.5 Future concerns and perspectives 206 8.6 Conclusion 207 References 207

9. Eucalyptus essential oils Rabia Shabir Ahmad, Muhammad Imran, Muhammad Haseeb Ahmad, Muhammad Kamran Khan, Adeela Yasmin, Hafiza Saima, Khadija Abbas, Rabbiya Chaudhary, and Muhammad Abdul Rahim

9.1 9.2 9.3

Introduction 217 Eucalyptus essential oil history 219 Some important types of eucalyptus essential oil 219 9.4 Production and composition 220 9.5 Techniques 222 9.6 Characterization and identification of essential oil components by techniques like NMR-13C 224 9.7 Eucalyptus essential oil chemistry and properties 225 9.8 Essential oil yield 225 9.9 Functional applications of Eucalyptus essential oil 226 9.10 Eucalyptus essential oils application in pharmacological, agro food, and nonfood products 228 9.11 Eucalyptus essential oils use in agro-industry 230 9.12 Eucalyptus essential oils as additives in active food packaging 230 9.13 Eucalyptus oils use in the fragrance industry 231 9.14 Safety, toxicity and regulation 232 9.15 Trade, storage stability and transport of eucalyptus essential oil 234 9.16 Conclusion 236 References 236

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10. Essential oils from Apiaceae family (parsley, lovage, and dill) Giorgiana M. Ca˘tunescu, Ioana M. Bodea, Adriana P. David, Carmen R. Pop, and Ancuța M. Rotar

10.1 Introduction 241 10.2 Factors influencing essential oil production of parsley, dill, and lovage 243 10.3 Extraction techniques of parsley, dill, and lovage essential oil 260 10.4 Chemical profile of parsley, dill, and lovage essential oil 268 10.5 Bioactivity of parsley, dill, and lovage essential oil 276 10.6 Applications of parsley, dill, and lovage essential oil 288 10.7 Safety and toxicity of parsley, dill, and lovage essential oil 294 10.8 Trade and regulation of parsley, dill, and lovage essential oil 298 10.9 Conclusion 300 References 302

11. Essential oils from Lamiaceae family (rosemary, thyme, mint, basil) Sumeyye Inanoglu, Gulden Goksen, Gulzar Ahmad Nayik, and Amir Sasan Mozaffari Nejad

11.1 Chemical composition of essential oils 309 11.2 Lamiaceae family 310 11.3 Composition of basil, mint, rosemary, and thyme oil 310 11.4 Extraction techniques 313 11.5 Safety, toxicity, and regulation of basil, mint, rosemary, and thyme oil 314 11.6 Storage stability of basil, mint, thyme, and rosemary oil 316 11.7 Applications of essential oils of basil, mint, rosemary, and thyme 317 11.8 Conclusion 320 References 320

12. Clove oil Muhammad Nadeem, Muhammad Imran, Ahmad Din, and Awais Khan

12.1 Introduction 325 12.2 Botanical description 326

12.3 Impurities and their removal from clove oil 329 12.4 Oil extraction by enzymes 329 12.5 Lipid oxidation in clove oil 331 12.6 Fortification of foods with clove oil 331 12.7 Future applications of clove oil 333 12.8 Summary of some clinical trials of polyunsaturated fatty acids 339 References 340

13. Ginger essential oil: Chemical composition, extraction, characterization, pharmacological activities, and applications Jalal Uddin, Humam Ahmed, Yahya Ibrahim Asiri, Ghulam Mustafa Kamal, and Syed Ghulam Musharraf

13.1 13.2 13.3

Introduction 345 Productions of GEO 346 Chemical composition and yield of GEO 348 13.4 Extraction methods of GEO 352 13.5 Analytical method for characterization of GEO 358 13.6 Pharmacological activities of GEO 361 13.7 Applications of GEO 367 13.8 Safety, toxicity, and regulation 368 13.9 Trade, storage stability and transport 368 13.10 Conclusion 369 References 370

14. Cinnamon essential oil Atif Liaqat, Samreen Ahsan, Muhammad Shoaib Fayyaz, Ayesha Ali, Syeda Aiman Ashfaq, Sonia Khan, Mujib Arjumund Khan, Tariq Mehmood, Adnan Khaliq, Muhammad Farhan Jahangir Chughtai, Saeme Asgari, Masoumeh Parzadeh, Amir Sasan Mozaffari Nejad, and Gulzar Ahmad Nayik

14.1 Introduction 377 14.2 Production and composition of cinnamon EO 378 14.3 Characterization of cinnamon essential oil 383 14.4 Health benefits of cinnamon essential oil 383 14.5 Application of cinnamon essential oil in food and nonfood industries 386 14.6 Conclusion 387 References 387

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15. Nutmeg essential oil 391

18. Patchouli essential oil

Mahpara Khanam, Aamir Hussain Dar, Fiza Beg, Shafat Ahmad Khan, Gulzar Ahmad Nayik, and Ioannis Konstantinos Karabagias

Syeda Saniya Zahra , Gulzar Ahmad Nayik, and Tooba Khalid

15.1 15.2 15.3 15.4 15.5 15.6 15.7

Introduction 391 Botanical aspects 392 Essential oil production 392 Composition of nutmeg 393 Extraction of nutmeg essential oil 393 Uses and applications 394 Safety, toxicity, and regulation of nutmeg essential oil 397 15.8 Conclusion 397 References 398

18.1 Introduction 429 18.2 Production and composition 430 18.3 Extraction techniques 432 18.4 Characterization 434 18.5 Chemistry and properties 437 18.6 Applications 444 18.7 Safety, toxicity, and regulation 449 18.8 Trade, storage stability, and transport 450 18.9 Conclusion 451 References 451

19. Clary sage essential oil

16. Rosewood essential oil Muhammad Haseeb Ahmad, Muhammad Faizan Afzal, Muhammad Imran, Muhammad Kamran Khan, Muhammad Sajid Arshad, Muhammad Bilal Hussain, and Marwa Waheed

16.1 16.2 16.3 16.4 16.5 16.6 16.7 16.8

Introduction 401 Production of rosewood essential oil 402 Composition of rosewood oil 402 Extraction of rosewood oil 403 Chemical characterization 406 Characteristics of rosewood 407 Applications of rosewood essential oil 407 Safety and toxicity of rosewood essential oils 409 16.9 Storage stability 409 16.10 Trade of rosewood oil 410 16.11 Conclusion 410 References 411

17. Juniper essential oil: An overview of bioactive compounds and functional aspects Tabussam Tufail, Huma Bader Ul Ain, Arooj Saeed, Muhammad Imran, Shahnai Basharat, and Gulzar Ahmad Nayik

17.1 Introduction 415 17.2 Production and composition 419 17.3 Extraction techniques (distillation) 419 17.4 Applications 420 17.5 Health claims 420 17.6 Conclusion 426 References 426

Monika Hans, Deeksha, Gulzar Ahmad Nayik, and Ameeta Salaria

19.1 Introduction 459 19.2 Clary sage oil production and chemical composition 460 19.3 Extraction techniques (distillation) 463 19.4 Characterization of essential oil components 466 19.5 Chemistry and properties 467 19.6 Applications 467 19.7 Safety, toxicity and regulation 473 19.8 Trade, storage, stability, and transport 474 19.9 Conclusion 474 References 474

20. Tea tree essential oil Iahtisham-Ul-Haq, Sipper Khan, Muhammad Sohail, Muhammad Jawad Iqbal, Kanza Aziz Awan, and Gulzar Ahmad Nayik

20.1 20.2 20.3 20.4

Introduction 479 Phytochemistry of tea tree EO 480 Extraction of tea tree EO 485 Applications of tea tree essential oils 489 20.5 Safety concerns 495 20.6 Conclusions 496 References 497

Index 501

Contributors Khadija Abbas Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan

Ayesha Ali Institute of Food Science and Technology, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan

Muhammad Afzaal Food Safety and Biotechnology Laboratory, Department of Food Science, Government College University Faisalabad, Faisalabad, Pakistan

Mohammad Javed Ansari Department of Botany, Hindu College Moradabad (Mahatma Jyotiba Phule Rohilkhand University Bareilly), Bareilly, India

Muhammad Faizan Afzal Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan

Muhammad Sajid Arshad Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan Saeme Asgari Department of Biochemistry and Biophysics, Islamic Azad University, Tehran Medical Sciences Branch, Tehran, Iran

Muhammad Haseeb Ahmad Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan

Syeda Aiman Ashfaq Institute of Food Science and Technology, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan

Rabia Shabir Ahmad Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan

Yahya Ibrahim Asiri Department of Pharmacology and Toxicology, College of Pharmacy, King Khalid University, Abha, Saudi Arabia

Humam Ahmed Silesian University of Technology, Faculty of Energy and Environmental Engineering, Environmental Biotechnology Department, Gliwice, Poland

Kanza Aziz Awan Department of Food Science and Technology, University of Central Punjab, Lahore, Pakistan

Samreen Ahsan Institute of Food Science and Technology, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan

Shahnai Basharat University Institute of Diet and Nutritional Sciences, The University of Lahore, Lahore, Pakistan Fiza Beg Department of Food Technology, Islamic University of Science and Technology, Awantipora, Kashmir, India

Huma Bader Ul Ain University Institute of Diet and Nutritional Sciences, The University of Lahore, Lahore, Pakistan

Garima Bhardwaj Department of Chemistry, Sant Longowal Institute of Engineering and Technology, Sangrur, Punjab, India

Umar Farooq Alahmad Institute of Food Science and Nutrition, University of Sargodha, Sargodha, Pakistan

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Contributors

Tejasvi Bhatia Department of Forensic Science, School of Bioengineering and Biosciences, Lovely Professional University, Phagwara, Punjab, India Ioana M. Bodea Department of Paraclinical and Clinical Sciences, Faculty of Veterinary Medicine, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Cluj-Napoca, Romania Tridip Boruah P.G. Department of Botany, Madhab Choudhury College, Barpeta, Assam, India Giorgiana M. Ca˘tunescu Department of Technical and Soil Sciences, Faculty of Agriculture, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Cluj-Napoca, Romania Rabbiya Chaudhary Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan Muhammad Farhan Jahangir Chughtai Institute of Food Science and Technology, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan Aamir Hussain Dar Department of Food Technology, Islamic University of Science and Technology, Awantipora, Kashmir, India Adriana P. David Department of Technical and Soil Sciences, Faculty of Agriculture, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Cluj-Napoca, Romania Deeksha Department of Pharmacology, Delhi Institute of Pharmaceutical Sciences and Research (DIPSAR), New Delhi, India Suraj Kr. Dey P.G. Department of Botany, Madhab Choudhury College, Barpeta, Assam, India Ahmad Din Faculty of Food, Nutrition & Home Sciences, National Institute of Food Science and Technology, University of Agriculture, Faisalabad, Pakistan Muhammad Shoaib Fayyaz Institute of Food Science and Technology, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan

Apurba Gohain Department of Chemistry, Assam University Silchar, Silchar, Assam, India Gulden Goksen Department of Food Technology, Vocational School of Technical Sciences at Mersin Tarsus Organized Industrial Zone, Tarsus University, Mersin, Turkey Khushbu Gumber Department of Chemistry, University Institute of Science (UIS), Chandigarh University, Gharuan, Mohali, Punjab, India Monika Hans Department of Food Science and Technology, Padma Shri Padma Sachdev, Government PG College for Women Gandhi Nagar, Jammu, Jammu & Kashmir, India Muhammad Bilal Hussain Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan Muzzamal Hussain Department of Food Science, Government College University Faisalabad, Faisalabad, Pakistan Iahtisham-Ul-Haq Kauser Abdulla Malik School of Life Sciences, Forman Christian College (A Chartered University), Lahore, Pakistan Muhammad Imran Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad; University Institute of Diet and Nutritional Sciences, The University of Lahore, Lahore, Pakistan Sumeyye Inanoglu Department of Food Science, Rutgers, The State University of New Jersey, New Brunswick, NJ, United States Muhammad Jawad Iqbal Department of Food Science and Technology, Minhaj University, Lahore, Pakistan Shafeeqa Irfan Institute of Food Science and Nutrition, University of Sargodha, Sargodha, Pakistan Ghulam Mustafa Kamal Department of Chemistry, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan

Contributors

Ioannis Konstantinos Karabagias Department of Food Science and Technology, School of Agricultural Sciences, University of Patras, Agrinio, Greece

Mahpara Khanam Department of Food Engineering and Technology, Institute of Chemical Technology, Jalna, Maharashtra, India

Gurpreet Kaur Department of Zoology, Mata Gujri College, Fatehgarh Sahib, India

Atif Liaqat Institute of Food Science and Technology, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan

Jaspreet Kaur Department of Food Science and Technology, Punjab Agricultural University, Ludhiana, Punjab, India Kamaljit Kaur Department of Food Science and Technology, Punjab Agricultural University, Ludhiana, Punjab, India Kamalpreet Kaur Department of Chemistry, Mata Gujri College, Fatehgarh Sahib, India Tooba Khalida Department of Pharmacognosy, Shifa College of Pharmaceutical Sciences, Shifa Tameer-e-Millat University, Islamabad, Pakistan Adnan Khaliq Institute of Food Science and Technology, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan Awais Khan Department of Dairy Technology, University of Veterinary and Animal Sciences, Lahore, Punjab, Pakistan Muhammad Kamran Khan Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan Mujib Arjumund Khan Department of Nutritional Sciences, La-Mak Foods, Ltd. Shakir Kot Tehsil Sadiqabad, Rahim Yar Khan, Pakistan

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Saba Liaqat Department of Environmental Design, Health, and Nutritional Sciences, Allama Iqbal Open University, Islamabad, Pakistan Mohammad Makeri Food Technology Department, NAERLS, Ahmadu Bello University, Zaria, Kaduna State, Nigeria Tariq Mehmood Institute of Food Science and Technology, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan Amir Sasan Mozaffari Nejad School of Medicine, Jiroft University of Medical Sciences, Jiroft, Iran Syed Ghulam Musharraf Faculty of Science, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan Vishal Mutreja Department of Chemistry, University Institute of Science (UIS), Chandigarh University, Gharuan, Mohali, Punjab, India Muhammad Nadeem Department of Dairy Technology, University of Veterinary and Animal Sciences, Lahore, Punjab, Pakistan

Shafat Ahmad Khan Department of Food Technology, Islamic University of Science and Technology, Awantipora, Kashmir, India

Gulzar Ahmad Nayik Department of Food Science & Technology, Government Degree College Shopian, Srinagar, Jammu & Kashmir, India

Sipper Khan University of Hohenheim, Institute of Agricultural Engineering, Tropics and Subtropics Group, Stuttgart, Germany

Rabia Noreen Institute of Food Science and Nutrition, University of Sargodha, Sargodha, Pakistan

Sonia Khan Institute of Food Science and Technology, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan; Government College Women University, Faisalabad, Pakistan

Prastuti Parashar P.G. Department of Botany, Madhab Choudhury College, Barpeta, Assam, India Masoumeh Parzadeh Department of Microbiology, Islamic Azad University, Science and Research Branch, Tehran, Iran

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Contributors

Carmen R. Pop Department of Food Science, Faculty of Food Science and Technology, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Cluj-Napoca, Romania

Preeti Saluja Department of Chemistry, RKMV, Shimla, Himachal Pradesh, India

Muhammad Abdul Rahim Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan

Bakhtawar Shafique Institute of Food Science and Nutrition, University of Sargodha, Sargodha, Pakistan

Muhammad Modassar Ali Nawaz Ranjha Institute of Food Science and Nutrition, University of Sargodha, Sargodha, Pakistan Amara Rasheed Department of Food Science, Government College University Faisalabad, Faisalabad, Pakistan Muhammad Ahtisham Raza Department of Food Science, Government College University Faisalabad, Faisalabad, Pakistan Ancuța M. Rotar Department of Food Science, Faculty of Food Science and Technology, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Cluj-Napoca, Romania Arooj Saeed University Institute of Diet and Nutritional Sciences, The University of Lahore, Lahore, Pakistan Farhan Saeed Department of Food Science, Government College University Faisalabad, Faisalabad, Pakistan Amna Sahar Department of Food Engineering, University of Agriculture, Faisalabad, Pakistan Hafiza Saima Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan Ameeta Salaria Department of Food Science and Technology, Padma Shri Padma Sachdev, Government PG College for Women Gandhi Nagar, Jammu, Jammu & Kashmir, India Aliyu Salihu Department of Biochemistry, Ahmadu Bello University, Zaria, Kaduna State, Nigeria

Aysha Sameen Department of Food Science and Technology, Government College, Women University, Faisalabad, Pakistan

Ajay Sharma Department of Chemistry, University Institute of Science (UIS), Chandigarh University, Gharuan, Mohali, Punjab, India Muhammad Sohail Research and Development Section, Punjab Food Authority, Government of the Punjab, Lahore, Pakistan Harvinder Singh Sohal Department of Chemistry, University Institute of Science (UIS), Chandigarh University, Gharuan, Mohali, Punjab, India Farwa Tariq National Institute of Food Science and Technology, University of Agriculture, Faisalabad, Pakistan Tayyaba Tariq National Institute of Food Science and Technology, University of Agriculture, Faisalabad, Pakistan Tabussam Tufail University Institute of Diet and Nutritional Sciences, The University of Lahore, Lahore, Pakistan Jalal Uddin Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, Abha, Saudi Arabia Chayanika Ujir P.G. Department of Botany, Madhab Choudhury College, Barpeta, Assam, India Saba Umar Institute of Food Science and Nutrition, University of Sargodha, Sargodha, Pakistan Marwa Waheed Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan Adeela Yasmin Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan

Contributors

Syeda Mahvish Zahra Institute of Food Science and Nutrition, University of Sargodha, Sargodha; Department of Environmental Design, Health, and Nutritional Sciences, Allama Iqbal Open University, Islamabad, Pakistan

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Syeda Saniya Zahra Department of Pharmacognosy, Shifa College of Pharmaceutical Sciences, Shifa Tameer-e-Millat University, Islamabad, Pakistan

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C H A P T E R

1 Essential oils in plants: Plant physiology, the chemical composition of the oil, and natural variation of the oils (chemotaxonomy and environmental effects, etc.) Sipper Khana, Amna Saharb, Tayyaba Tariqc, Aysha Sameend, and Farwa Tariqc a

University of Hohenheim, Institute of Agricultural Engineering, Tropics and Subtropics Group, Stuttgart, Germany bDepartment of Food Engineering, University of Agriculture, Faisalabad, Pakistan cNational Institute of Food Science and Technology, University of Agriculture, Faisalabad, Pakistan dDepartment of Food Science and Technology, Government College, Women University, Faisalabad, Pakistan

1.1 Introduction Essential oils are extricated from different bioactive rich plants exhibiting aroma. These essential oils (EOs) are natural, volatile complex constituents characterized by the aroma of their respective plants (Mironescu and Georgescu, 2021). A plethora of applications have been recorded in the food, cosmetics, perfumeries, and pharmaceutical industries owing to their antioxidant and antimicrobial activities (Dhifi et al., 2016; Mironescu and Georgescu, 2021). As per the “International Standard Organization on Essential oils (ISO 9235:2013)” and “European Pharmacopoeia (Council of Europe 2004),” EOs are defined as the output retained by extracting through hydrodistillation, steam distillation, or dry distillation or via another suitable mechanical extraction process, used for Citrus fruits only (cold pressing generally used as the bioactive constituents are thermosensitive and unstable). As per the definition,

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00016-5

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Copyright # 2023 Elsevier Inc. All rights reserved.

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1. Essential oils in plants

other aromatic products extracted using solvent-based extrication, supercritical fluid extraction (SFE), and microwave-assisted extraction (MAE) are excluded (Hanif et al., 2019). Worldwide production of EOs is evaluated to be greater than 150,000 tons with revenue generation of USD 6B, approximately increasing three times than 1990 with a 50% increase observed since 2007. Different economic analyses have indicated the amount to reach 370,000 tons annually after the 2020s with a value of more than USD 10B (Barbieri and Borsotto, 2018). The major producers of EOs include China, India, Indonesia, Sri Lanka, and Vietnam while minor contributions are also obtained from African countries including Morocco, Tunisia, Uganda and Ethiopia, Egypt, and Algeria; the Ivory Coast, South Africa, Ghana, Kenya, and Tanzania (Barbieri and Borsotto, 2018). This increase in consumption is owing to the demand from these principal markets: food and beverage (35%), fragrances, aromatherapy and cosmetics (29%), household (16%), and pharmaceutical (15%). The food and beverage industry mainly employs essential oils from orange, lemon, and lime (Manion and Widde, 2017). EOs are also distinguished with different names including essences, volatile oils, etheric oils, or aetheroleum. They contain more than 300 different compounds containing hydrocarbons (in natural mixtures) (terpenes), oxygen- (alcohols, aldehydes, ketones, carboxylic acids, esters, lactones), and sulfur-containing (sulfides, disulfides, trisulp hides) organic constituents (Conde-Herna´ndez et al., 2017). EOs are obtained from different plant parts including roots, shoots, flowers, fruits, and seeds; where they are initially produced and stored in the secretory structures. These secretory structures vary in their morphological, functional, and distribution sections as they reduce the autotoxicity. Being found on either the internal and external plant organs surface or within the tissues structure, they are considered as external or internal secretory structures, respectively. Internal structures consist of idioblasts, secretory cavities, and ducts both while the counterparts contain glandular trichomes, epidermal cells, and osmophores. Some storage organs in roots, tubers, and wood sections require mechanical degradation to facilitate extraction from the oil storage organs (De Sousa, 2015). The compositional profile varies according to both intrinsic and extrinsic factors. Intrinsic include genetically variations, sexually, seasonal and ontogenetic based while extrinsic ones include both environment and ecological-based (Mironescu and Georgescu, 2021). Among different sources, not only does the chemical composition varies but also the bioactive constituents obtained contribute to numerous functional contributions. These EOs have antimicrobial, antioxidant, anticancer, acaridical, herbal, and therapeutic contributions. For instance, cinnamon EO exhibited the highest antibacterial effect while the fumigant potential was recorded in both cinnamon, clove, and anise EOs (Tu et al., 2018). This chapter will highlight the phytochemistry, chemical characteristics, and administration of different essential oils obtained from the plants while considering the safety concerns related to them in different industrial applications.

1.2 Phytochemistry of different essential oils Phytochemicals are nonnutrimental chemical constituents or secondary metabolites generated by plants through many chemical pathways (Budisan et al., 2017). They exhibit a critical role in physiological activities of plant growth such as symbiotic relationships,

1.2 Phytochemistry of different essential oils

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reproduction, and their interactions with the environment and other organisms. Phytochemicals include flavonoids, polyphenols, steroidal saponins, vitamins, and organosulfur compounds (Forni et al., 2017). The majority of phytochemicals, food, herbal items, and beverages are frequently referred to as “nutraceuticals” in the literature, focusing on their health-promoting effects, including the prevention as well as treatment of cardiovascular disease, cancers, Alzheimer’s disease along with some neural disorders (Winter et al., 2017).

1.2.1 Major phytochemicals in the plant-based essential oils Essential oils are made up of a complex blend of chemicals at different concentrations ranging from 20 to 60 (Chouhan et al., 2017). Some major phytochemicals in plant-based essential oils are given below: 1.2.1.1 Terpenes Terpenes, commonly known as terpenoids, are the largest and most diversified family of naturally occurring chemicals. They are divided as mono, di, tri, tetra, and sesquiterpenes based on the number of isoprene units they contain. They’re mostly found in plants and comprise the majority of essential oils. Terpenes have an important and diverse role among the natural substances that deliver medical benefits to an organism. Terpenes can be found in thyme, cannabis, tea, Spanish sage, and citrus fruits (e.g., lemon, orange, and mandarin). Terpenes offer a wide range of therapeutic potential, including antiplasmodial activity, which is significant because its mechanism of action is comparable to that of the widely used antimalarial drug chloroquine. Antiviral effects of monoterpenes, in particular, have been intensively studied. Terpenes have the potential to operate as antidiabetic and anticancer agents, which is highly crucial due to the rise in the incidence of cancer and diabetes. Besides these properties, Terpenes also can suppress the side effects and change the route of administration (Cox-Georgian et al., 2019). They have a complex structure with a wide range of effects and different mechanisms of action (Yang et al., 2020). The chemical structures of classes of terpenes are provided in Fig. 1.1 below: 1.2.1.2 Alpha-pinene Alpha-pinene is among two isomers of pinene, a terpene chemical component. It can be found in the oils of a variety of coniferous plants, the most prominent of which being the pine. This molecule is usually found in essential oils and is used in oils and diffusers as a flavoring ingredient. The racemic combination is found in several oils, such as eucalyptus oil and orange peel oil. Essential oils’ antiinflammatory properties are linked to this molecule, which € has a powerful antiinflammatory effect (Ozbek and Yılmaz, 2017). The chemical structure of the Alpha-Pinene is presented in Fig. 1.2. 1.2.1.3 Steroids Steroids are a class of phytochemicals produced by plants. Sterol and its derivatives are examples of steroids. The chemical structure of steroids is provided below in Fig. 1.2. The three primary types of sterols are zymosterol, zoosterol, and phytosterol. The largest concentrations of steroids are found in foods including vegetable oils, nuts, and seeds. They are also

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1. Essential oils in plants

FIG. 1.1 Chemical structures of different classes of terpenes including isoterprene unit, moniterpene (limonene), sesquiterpenoid (aristolane), diterpene (abietane), and tetracyclic triterpene (dammarane).

FIG. 1.2 Chemical structures of alpha-pinene and steroid (estrange).

found in plant-based essential oils like citrus and bergamot oils as essential oils are rich in essence-giving chemicals. Steroids provide certain benefits to plants as well as to humans after consumption. Plants utilize steroids in their metabolism. For humans, they are a kind of cholesterol-like molecule and the most widely utilized cholesterol-lowering agent by restricting the amount of cholesterol that may enter the body (Siano and Cautela, 2020). Moreover, steroids are utilized in medicine for the management of some diseases. The most frequent sterol derivations are bile acid and vitamin D, both of which are crucial for growth and development (Kolekar et al., 2019). 1.2.1.4 Tannins Tannin, commonly recognized as tannic acid, is a collection of phenolic chemicals found in woody flowering plants as well as essential oils. Tannins are stashed in vacuoles within the plant cell as bioactive compounds, which shield the other cell structures. Many plants have

1.2 Phytochemistry of different essential oils

5

FIG. 1.3 Chemical structures of flavonoid, tannin, coumarin, and glycoside.

them naturally in their roots, wood, bark, leaves, and fruit, especially the bark of oak species, sumac, and myrobalan species. They can also be found in galls, which are diseased lesions caused by insect bites ( Jafari et al., 2019). Tannins act as herbivore repellents and have a variety of commercial uses. They are nonvolatile chemicals generated in leaves that are toxic and are frequently employed by plants to ward off predatory animals. Tannins’ intrinsic antioxidant and antibacterial action are attributed to their phenolic constituents. Their antioxidant action is determined by their structure and redox characteristics, which are crucial in the absorption and neutralization of free radicals as well as the breakdown of peroxides. Tannins have been demonstrated to have positive qualities to help protect the environment (Cano et al., 2020). The chemical structure of Tannin is given in Fig. 1.3. 1.2.1.5 Flavonoids Flavonoids are chemically complex secondary metabolites that serve a range of roles in plants. They are water-soluble and are polyphenolic compounds with 15 carbon atoms. Flavonoids are the most prevalent form of polyphenolic chemical present in essential oils. Some flavonoids are found in high concentrations in plants’ oil glands, whereas others were found in areas where carotenoids were present. Certain flavonoids markers detected are present in essential oil-rich locations and carotenoids. Some flavonoids also block specific spores, which helps to protect plants from illness (Kaurinovic and Vastag, 2019). They provide a wide range of pharmacological and physiological benefits for humans, including free radical scavenging ability, antioxidative activity, antiatherosclerotic, hepatoprotective, prevention of coronary heart disease, anticancer, and antiinflammatory properties (Go´rniak et al., 2019). The chemical structure of Flavonoid is given in Fig. 1.3. 1.2.1.6 Glycosides Glycosides are generally plant-derived chemicals mostly found in essential oils. One or more sugars are coupled with alcohol, phenol, or a complex molecule such as a steroid nucleus to form these compounds. Because they do not contain nitrogen, they are incorrectly referred to be alkaloids. Glycosides are used as medicines and have various pharmacological

6

1. Essential oils in plants

properties. One of the important uses of glycosides is treating cardiac failure and irregular heartbeats and they are specifically known as cardiac glycosides (Saroj et al., 2020). Cardiac glycosides may be found in a wide variety of plants, including Digitalis purpurea and Digitalis lanata. Cardiac glycosides work by increasing calcium availability to cardiac fibers and blocking sodium-potassium-adenosine triphosphatase, resulting in higher intracellular sodium and lower intracellular potassium levels (Hosseini et al., 2019). The chemical structure of Glycosides is given in Fig. 1.3. 1.2.1.7 Alkaloids Alkaloids are tiny secondary metabolites of plants that contain nitrogen in a ring; alkaloids make up around 20% of plant species. These are natural chemicals that prevent herbivorous animals due to their bitter taste. Most of the plant essential oils are rich in alkaloids. They are utilized as natural insecticides in some plants as alkaloids shield against the harmful activities of some insect species. Plant alkaloids include morphine, which is used to relieve muscle spasms, emetine, and cephalin. They are used as cures for intoxication; caffeine, which has stimulant characteristics; and quinine, which has antimalarial effects and a slightly bitter taste (Fialova et al., 2017). The chemical structures of Alkaloids are given in Fig. 1.4. 1.2.1.8 Phenols Phenolic compounds are undoubtedly the most extensively studied natural compounds due to their potential health benefits. Generic terms “phenolics,” “polyphenolics,” or “phenolic compounds” refer to more than 8000 compounds found in the plant kingdom. A phenolic compound’s fundamental structure consists of an aromatic ring with one or more hydroxyl (–OH) groups including functional derivatives like esters glycosides and methyl ethers. Naturally, phenolics contain diverse structures from simple to complex. As a result, the presence of –OH groups in the structure of phenolics can be linked to their antibacterial properties. The amount and position of double bonds in the structure influence the relative toxicity of phenolics against microorganisms (Bhuyan and Basu, 2017). Phenolics are usually concentrated in essential oils and give them aromatic properties. Most citrus essential oils contain phenols and have a specific aroma (Ahmed et al., 2019). The chemical structure of Phenol is given in Fig. 1.5. 1.2.1.9 Coumarin Coumarins are a group of secondary metabolites obtained from plants that are formed through the phenylpropanoid pathway. Coumarins are present in a wide variety of plant

FIG. 1.4 Chemical structures of alkaloids.

7

1.2 Phytochemistry of different essential oils

FIG. 1.5 Chemical structures of phenol and saponin (liquorice).

species including essential oils of Rubiaceae, and Poaceae plants, and are best recognized in the form of Citrus, Bergamini’s, and bergamot oil. They have a role in plant defense against phytopathogens, environmental stresses response, oxidative stress control, and perhaps as signaling molecules. Coumarins have been widely investigated for their capacity to fight infections in both plants and animals, in addition to their function in iron absorption (Silveira et al., 2020). The chemical structure of Coumarin is given in Fig. 1.5. 1.2.1.10 Saponins Saponins are derived from the roots of the soapwort plant (Saponaria), which were once used as soap. They are usually found in onion and garlic essential oils. Saponins decrease blood lipids, reduce cancer risks, and improve blood glucose control. A high-saponin diet can help prevent dental cavities and platelet clumping, as well as cure hypercalciuria in humans, and act as an antidote to acute lead poisoning (Runde, 2020). A list of major phytochemicals in different essential oils is given in Table 1.1. The chemical structure of Saponin is given in Fig. 1.5. TABLE 1.1

Phytochemicals present in different plant-based essential oils.

Phytochemicals

Essential oils

Citation

Terpenes

Tea, thyme, cannabis, Spanish sage, and citrus fruits (e.g., lemon, orange, mandarin)

Cox-Georgian et al. (2019)

Alpha-pinene

Coniferous plants (pines), rosemary, eucalyptus, orange peel oil, cypress, juniper berry, frankincense, helichrysum, wild orange

€ Kumar et al. (2021); Ozbek and Yılmaz (2017)

Steroids

Citrus, bergamot

Siano and Cautela (2020)

Tannins

Eucalyptus, peppermint, fennel, rosemary, lavender

Shankar et al. (2021)

Flavonoids

Lavender, peppermint, grapefruit

Russo (2018) Continued

8

1. Essential oils in plants

TABLE 1.1 Phytochemicals present in different plant-based essential oils—cont’d Phytochemicals

Essential oils

Citation

Glycosides

Clove oil

Sadiq et al. (2019)

Alkaloids

Mint, orange, rosemary, clove

Misharina and Alinkina (2017)

Phenols

Orange, lemon, mandarin, tangerine, neroli, cinnamon, clove, thyme, oregano, savory, rosemary, neem

Sujatha and Sirisha (2019)

Coumarin

Citrus, Bergamini, bergamot, cinnamon, sweet clove, cassia, lavender, woodruff oil

Ogawa et al. (2020); Silveira et al. (2020)

Saponin

Onion, garlic

Runde (2020); Shahrajabian et al. (2020)

1.3 Natural variation of the oils (chemotaxonomy and environmental effects, etc.) Generally, the EOs composition varies according to geographical reasons, harvesting seasons in each type of plant. In thymus and Origanum species, 1-methyl-4-(1-methylethyl) -1,4-cyclohexadiene (γ-terpinene) and 1-methyl-4-(1-methylethyl)-benzene (p-Cymene) are considered as the initial constituents of 5-methyl-2-(1-methylethyl) phenol (thymol) and 2-methyl-5-(1-methylethyl)- phenol (carvacrol). While in the Greek oregano plants, these compounds are approximately considered equal in their potency with stable concentrations even though collected from different geographical regions (with delayed harvesting). This indicates that p-cymene forms thymol through g-terpinene with this theory also supported by T. vulgaris both biologically and functionally. Other EOs have exhibited strong antimicrobial properties during or after the flowering season (Hashemi et al., 2017). Other variations have been observed in the EOs obtained from different plant parts. For instance, EO extracted from coriander seeds (Coriandrum sativum L.) exhibited different oil composition as compared to the on from cilantro immature leaves (Delaquis et al., 2002; Falleh et al., 2020). Similarly, some EOs are highly volatile and sensitive to thermal conditional incorporated in their extraction and hydrodistillation resulting in chemical alterations in the compositions. This impact can be reduced especially for stem EOs by employing supercritical fluids (carbon dioxide) (Chemat et al., 2020; Fornari et al., 2012). Seasonal variations have also been observed in some studies along with terpene dynamics variations during the fruit ripening stage. At the semiripe stage, the monoterpenes concentration was high that later decreased. Sesquiterpenes intensively increased during the ripening stage while the ester occurrence was very low. Although the cosmetic industry is growing exponentially, the EOs from fruits and leaves are rarely employed. Moreover, the impacts of environmental and genetic factors are still unknown. Another aspect of the alterations of EOs includes the drying method employed. An investigation explained both dried and fresh ginger increasing the terpene hydrocarbons while decreasing the concentration of gingerol and monoterpene alcohols formation to the complementary acetates. Another study also highlighted that the drying process helped in decreasing the monoterpenes and citrals as compared to sesquiterpenes owing to the significant contrast in volatile conditions among the classes of compounds present (Eslahi et al., 2017; Neri-Numa et al., 2019) (Tables 1.2–1.4).

TABLE 1.2 Characteristic attributes of different extraction methodologies in the processing industry. Types of extraction

Principle

Advantages

Examples of plant Name of Disadvantages extraction plants

(SPME) Solid Separating the phase micro analyte between extraction the sorbent coated fibers and sample

1: Don’t require a 1: Sample must Rosmarinus solvent. be clean officinalis L. 2: Simple. 2: Matrix effect leaves of 3: Fast Eucalyptus 4: Sensitive citriodora

(LLE) Liquidliquid extraction

Dividing the analyte among the two immiscible liquids to extract the compound of interest

1: It is best suitable for thermolabile compounds and azeotropic mixtures

1: Intensive workforce 2: Emulsion formation. 3: Consumption of large number of solvents 4: Difficulty in automate

Leaves of Veronica longifolia

(SPE) Solid phase extraction

Separation of the analyte between the solid and liquid phases for extraction of the target compound

1: Cheap 2: Less organic compound consumption and less time 3: Simple

1: Analyte discoloration. 2: Need filtration 3: Sorbent absorption capacity is limited.

carob fruits

(DIC) Instant controlled pressure drop extraction

A sudden drop in pressure and high temperature for short time increase the quality of extract

1: Other compounds can be extracted by processing residue 2: Appropriate for essential oil extraction 3: Less consumption of solvent and require less time

Cananga oil 1: Efficiency depends on the optimization Orange peel of the parameters

Compounds to be extracted

Cosmeticeutics

Sample size

Reference

–

Bicchi et al. (2000), Zini et al. (2001)

–

Kuba´tova´ et al. (2001), Suomi et al. (2000)

–

Ozel et al. (2003), Papagiannopoulos et al. (2004)

kava root

Thymbra spicata L. carob fruits

(Olive) Olea europaea leaves

Vanillic acid Oleuropein Luteolin 7 glucoside

(Grape stalk) Ellagic acid Vitis vinifera Gallic acid L. powder Quercetin

Anticancer Antioxidant Antiinflammatory

Mkaouar et al. (2015), Ribeiro et al. (2015) Georgiev et al. (2014), SanchezValdepenas et al. (2015)

Continued

TABLE 1.2 Characteristic attributes of different extraction methodologies in the processing industry—cont’d Types of extraction (UAE) Ultrasoundassisted extraction

(MAE) Microwaveassisted extraction

(PLE) Pressurized liquid extraction

(SFE) Supercritical fluid extraction

Principle

Advantages

Examples of plant Name of Disadvantages extraction plants

The strength of ultrasound allows cavitation which disturbs the cell wall of the sample

1: Less power and solvent consumption, Minimum time 2: Appropriate for the extraction of thermolabile compounds

Different types of plants require different optimization of parameters Cell disruption is high

Lychee seed by-product

1: Require filtration 2: Cell disruption

Fucus vesiculosus alga

The release of the 1: Less solvent target compound consumption and occurs from the reduced time sample when the microwave radiations heats the water

Prunella vulgaris L. plant

Grape seeds

1: Solvent should be chosen carefully 2: Not suitable for thermolabile compounds

Hight temperature increases the release of the target compound with the aid of pressure, which enhances filling of extraction cell

1: Less solvent consumption 2: More extraction yield

Qualities of supercritical fluid use to alter the solvent selectivity and increase the extraction for the compound of interest

1: Need high 1: Appropriate maintenance for compounds having high boiling point and thermally stable 2: Online coupling with the chromatography analysis

Bran, wheat straw and germ Algae: Himanthalia elongate and synechocystis sp. Pitanga leaves

Compounds to be extracted

Cosmeticeutics

(Haskap berries) Lonicera caerulea L.

Anthocyanins Anti-aging

(Lamiaceae) Thymus serpyllum L.

Caffeic acid Rosmarinic acid Salvianolic acid

Analgesic agent Anti-septic

Myrtus communis L. leaves

Gallic acid Galloylquinic acid

Stimulant Hair tonic

(Tomato) Solhanum lycoperiscum

Naringenin Chlorogenic acid Rutin

Anti-allergic

(Blackberry) residue Rubus fruticous L. (Jabuticaba) skin Myrciaria cauliflora

Sample size

Reference

600 L

Celli et al. (2015)

Jovanovic et al. (2017)

150 L

Aleksic and Knezevic (2014), Dahmoune et al. (2015) Li et al. (2012a, b), Yamamoto et al. (2004) Machado et al. (2015), Sariburun et al. (2010)

Anticancer Antiinflammatory Anthocyanins

Santos et al. (2013, 2012)

Coffea arabica Oleic acid Palmitic acid Linoleic acid

Antiinflammatory 300 L Anti-photoaging

Del Carmen Velazquez Pereda et al. (2009), HurtadoBenavides et al. (2016)

(Grape) skin Qurcetin V. vinifera Catechin Epicatechin

Skin conditioning agent

Belsito et al. (2012), Chafer et al. (2005)

Cherry

(SWE) Subcritical water extraction

Extraction process is increased by hot water while the pressure keeps the water in a liquid state

1: Less time consuming 2: Less in cost 3: Environmentally friendly

1: It is selective because of different dielectric constants of the compounds

Moringa oleifera (PEF) Pulsed electric fields

Electroporation of the walls cells

Difficult ease of operation

Steam Distillation or Hydro Distillation

Large scale production

Temperature limitation

Solvent Extraction

Large scale production

Ohmic heating

Cell disruption is Should have high known how

Singh and Saldan˜a (2011)

(Potato) peel Chlorogenic Solanum acid tuberosum Gallic acid Ferulic acid By product Coumaric acid of onion skin By product of rice bran biomass

Khoza et al. (2014), Mishra et al. (2011)

Quercetin Caffeic acid Quinic acid Continuous

>1000 L Solubility limitation

>1000 L Continuous

TABLE 1.3 Chemical classes, structural representation, and therapeutic properties of essential oil constituents (Aumeeruddy-Elalfi et al., 2016; Sharifi-Rad et al., 2017). Compounds chemical class Hydrocarbons

Characteristics

Chemical structural representation

They mainly contain hydrogen and carbon molecules. Classified into terpenes (mono-, sesqui-, and di-terpenes) (C10, C15 and C20 respectively). They can be acyclic, alicyclic (mono-, bi-, or tri- cyclic) or aromatic

Farnesene CH3

CH3

Therapeutic properties

CH2 CH2

H3C

Examples

Antitumor, antiviral, antibacterial stimulant, hepatoprotectant, decongestant

(+)-limonene, ( )-αpinene, myrcene, sabinene, β-phellandrene, p-cymene, cadinene, fenchane, farnesene, thujane

Stimulant, Antiinflammatory, expectorant

Linalool oxide, ascaridole bisabolone oxide and sclareol oxide

Limonen CH3

CH3

H2C

Myrcene CH2

CH3

CH2

H3C

Oxides

They are strongest odorants with 1,8-cineole being the most widely occurring

1,8-Cineole H3C O CH3 CH3

Bisabolone oxide CH3 O

O

H3C

CH3

CH3

Linalool oxide H2C

H3C

CH3 O H3C

OH

Lactones

Lactones reportedly have high molecular weight

Esters

It contributes to a sweet smell, commonly present in many EOs

Geranyl acetate O

CH3

CH3 H3C

O

CH3

Antimicrobial, analgesic, antipyretic, sedative, hypotensive, antiviral

Alantrolactone, bergaptene, psoralen, costuslactone, aesculatine, citroptene, nepetalactone, dihydronepetalactone

Antiinflammatory, antispasmodic, sedative, antifungal, anesthetic

Eugenol acetate, geranyl acetate, bornyl acetate, linalyl acetate

Antimicrobial, antiseptic, balancing, tonifying, spasmolytic, anesthetic, antiinflammatory

Linalool, (+)-citronellol, nerol, geraniol, borneol, menthol, santalol, nerol

Bornyl acetate CH3

O H 3C

CH3 O

CH3

Linalyl acetate CH3 H3C

CH3

H3C H2C

Alcohols

Alcohols have the highest therapeutic contributions without any contraindications

O

Linalool CH3 H3C

O

H3C H2C

OH

Continued

TABLE 1.3 Chemical classes, structural representation, and therapeutic properties of essential oil constituents (Aumeeruddy-Elalfi et al, 2016; Sharifi-Rad et al., 2017)—cont’d Compounds chemical class

Characteristics

Chemical structural representation

Therapeutic properties

Examples

Menthol CH3

OH H3C

CH3

Citronellol CH3

CH3 H3C

Phenols

Phenols are considered most reactive, potentially toxic, can cause irritation to the skin and mucous membrane with crystalline structural properties at the room temperature

OH

Thymol CH3

HO H3C CH3

Carvacrol CH3 OH

H3C

CH3

Chavicol HO

CH2

Spasmolytic, anesthetic, irritant, immune stimulating

Thymol, carvacrol, eugenol, chavicol

Ketones

Ketones are considered relatively stable and not easily metabolized by the liver. They can also be neurotoxic and abortifacients in the case of thujone and camphor

Carvone O CH3 H2C

Mucolytic, regenerative, sedative, antiviral, neurotoxic, analgesic, digestive and spasmolytic

Pulegone, menthone, carvone, camphor, fenchone, thujone, verbenone

Antimicrobial, antipyretic, antiviral, soothing, hypotensive, sedative, spasmolytic, tonic, vasodilators

Benyaldehyde, citronellal, cinnamaldehyde, myrtenal, citral (geranial and neral), citronellal

CH3

Pulegone CH3 H3C O

H

CH3

Thujone H3C

O

H

H3C

Aldehydes

Aldehydes irritate the skin and mucous membranes. They exhibit sweet, pleasant fruity smell

CH3

Citronellal CH3 O

H3C

CH3

Geranial CH3 H3C

CH3

O

Neral CH3

CH3

H3C O

16

1. Essential oils in plants

TABLE 1.4 Summary of LD50 values for some essential oils with the experimented animal and mode of administration (Hashemi et al., 2017). Plant name

LD50 concentration

Mode of administration

Animals

References

Aegle marmelos L.

23.66 g/kg b.wt.

Oral

Mice

Kuttan and Liju (2017), Hashemi et al. (2017)

Baccharis dracunculifolia

DC >2 g/kg b.wt.

Oral

Rats

Kuttan and Liju (2017), Hashemi et al. (2017)

Cuminum cyminum

>2 g/kg b.wt.

Oral

Rats

Hashemi et al. (2017), Kuttan and Liju (2017)

Eucalyptus globulus Labill

3.8 g/kg b.wt.

Oral

Rats

Kuttan and Liju (2017), Hashemi et al. (2017)

Ligusticum chuanxiong

2.25 g/kg b.wt.

Intraperitoneal

Mice

Kuttan and Liju (2017), Hashemi et al. (2017)

Mentha longifolia L.

470 mg/kg b.wt.

Oral

Rats

Kuttan and Liju (2017), Hashemi et al. (2017)

Vitex negundo

300) generally with a lower molecular weight. High vapor pressure of EOs generally, at atmospheric pressure and room temperatures enables them to be partially in the vapor state. Structurally EOs have two major families

1.6 Applications of all essential oils

21

FIG. 1.7 General pathway of biosynthetic pathways of secondary metabolites in plants.

related to their hydrocarbon skeleton, including terpenoids and phenylpropanoids. Terpinoids and phenolic acids have distinct primary metabolic precursors that are biosynthesized through different pathways, as shown in the figure below (Fig. 1.7). For example, mevalonate and mevalonate-independent pathways are responsible for the biosynthesis of terpenoid, while the shikimate pathway was used for derivation of phenylpropanoid (Sharifi-Rad et al., 2017). Other than phenylpropanoids, terpenes, and terpenoids, numerous other chemical structures are also present contributing to a plethora of properties including antimicrobial, virucidal, insecticidal, antiparasitic, anticancer, antidiabetic, antioxidant, cardiovascular, cosmetic, and food-based contributions (Aumeeruddy-Elalfi et al., 2016). Some of these characteristics are summarized below in the table.

1.6 Applications of all essential oils 1.6.1 Antioxidant Free radicals and reactive oxygen species (ROS) are associated with inflammation, cancers, cardiovascular diseases, brain dysfunction, immune-related and age-based disorders. Plant EOs are mainly recognized as a useful source of natural antioxidants as depicted in various experimental models ( Jugreet et al., 2020). The secondary metabolites and phenolics with conjugated double bonds specifically exhibit the antioxidant properties, for example, monoterpene phenols including thymol and carvacrol, being active ingredients display redox properties. They also perform a fundamental role in the decomposition of the peroxide along with the neutralization of free radicals ( Jugreet et al., 2020; Sharifi-Rad et al., 2017). Recent work of EOs as an antioxidant (Elansary et al., 2018; Mehdizadeh and Moghaddam, 2018; Mutlu-Ingok et al., 2020; Valdivieso-Ugarte et al., 2019) include spices (Diniz Do Nascimento et al., 2020), basil (Ahmed et al., 2019), Thymus vulgaris and Thymbra spicata (Gediko glu et al., 2019), Mentha spp. (Stringaro et al., 2018), etc.

22

1. Essential oils in plants

1.6.2 Antiinflammatory Many EOs are clinically is used for its antiinflammatory potential. They are mainly used against allergies, rheumatism, or arthritis, in a research involving the geranium’s cutaneous application on mice, inflammation linked to accumulation of edema and neutrophil accumulation and edema. In research conducted on EO obtained from leaves and flowers of Cymbopogon nardus (L.) against egg albumin-induced paw edema model in Wistar rats. Similarly, it also hindered the release of mediators (serotonin and histamine) initially after inflammation (Rungqu et al., 2016). Another study evaluated an in vitro experiment conducted on spearmint, geranium, and lemongrass EOs restraining the human neutrophil’s adhering reaction by tumor necrosis factor-α (TNF- α) at lower concentrations. The principal antiinflammatory components include carvone, citral, citronellol, and geraniol; however, in vivo studies have also highlighted the intraperitoneal administration of EOs in mice to be effective in preventing deposition of neutrophil into the peritoneal cavity mainly triggered by the casein injection (Abe et al., 2004, 2003; Mao et al., 2021; Santos et al., 2019). Moreover, cinnamaldehyde and linalool from Cinnamomum osmophloeum Kanei are also found effective in several endotoxin-induced body weight loss and lymphoid organ enlargement in mice in a dose-dependent manner (0.9 and 5.2 mg/kg respectively). Studies have also associated them with the prevention of TRL4 NLRP3 pathway functioning as an antiinflammatory agent (Dorri et al., 2018; Kim et al., 2019; Kumar et al., 2019; Lee et al., 2018).

1.6.3 Antihyperpigmentation Various dermatological disorders including freckles, melasma, age spots, etc. are caused by tyrosinase enzymes that catalysis the melanin formation in the skin resulting in epidermal hyperpigmentation. The antityrosinase potential of various plant metabolites including EOs has been scrutinized for skin whitening purposes. For instance, Eucalyptus camaldulensis Dehnh. Flower EO is used for both antityrosinase and in the reduction of melanin synthesis. EO inhibited the signaling pathway regulating tyrosinase activities along with depletion of ROS in both cellular and intracellular levels (Di Martile et al., 2020; Huang et al., 2015). Similarly, cinnamaldehyde is also known to decline the tyrosinase and melanin content. It is also responsible for the down-regulating the tyrosinase without any cytotoxic display. Likewise, lime mint EO, with β-Caryophyllene constituent mainly decreased melanin in murine B16F10 melanoma cells in a dose-dependent manner. This active ingredient reduced melanogenesis by down-regulating the melanocyte expression including transcription factor (MITF), tyrosinase-related protein 1 and 2, and tyrosinase (Yang et al., 2015). Other antimelanogenic potentials of EOs include Citrus hystrix DC, Citrus reticulate Blanco, and Citrus grandis (IC50:96 15.92  1.06, 23.75  4.47, and 28.99  5.70 μg/mL respectively). This antimelanogenic potential on melanoma cells was evaluated in mice on both intracellular and extracellular levels (Aumeeruddy-Elalfi et al., 2018; El Khoury et al., 2019; Kim et al., 2018; Zhou et al., 2020).

1.6.4 Antidiabetic There is growing research for natural antidiabetic agents owing to their effective diabetes management with reduced tolerance and side effects. Pelargonium graveolens EO is considered effective for hypoglycemic effect along with decreasing lipid peroxidation activity and

1.6 Applications of all essential oils

23

improving antioxidant defense mechanism in the body (Al-Sagheer et al., 2018; Boukhris et al., 2012). Meanwhile, Melissa officinalis leaves EO significantly reduced the plasma glucose while improving the tolerance of glucose in type-2 diabetic mice. The EO at low concentration was effective for hypoglycemic control, mainly triggered by increased glucose uptake and increased adipose tissues and liver metabolism along with prevention of liver glucogenesis (Chung et al., 2010; Wojtunik-Kulesza et al., 2019). Menthol, another dietary monoterpene obtained from Mentha piperita L. plays a significant role as an antidiabetic agent. The research investigated menthol’s role on glucose metabolic enzymes and pancreatic islet cell apoptosis of streptozotocin nicotinamide (STZ-NA) in diabetic rats with 25, 50, and 100 mg/kg menthol and glibenclamide (600 μg/per kilogram body weight basis) for 45 consecutive days. Menthol reportedly decreased the blood glucose levels along with glycosylated hemoglobin while increasing the hemoglobin (total), enhancing the plasma insulin, and escalating the liver glycogen in diabetic rats. Additionally, the hepatic glucose metabolic enzymes and liver damage serum biomarkers were almost also reported to be back to normal levels. Furthermore, other abnormalities in hepatic and pancreatic islets were also diminished. The mechanism adopted was by suppressing the pancreatic β-cells apoptosis, and increase in antiapoptotic Bcl-2 concentration, and decreasing the Bax expressions (pro-apoptosis) resulted in an effective diabetes management (Bouyahya et al., 2020b; Madhuri and Naik, 2017; Muruganathan et al., 2017).

1.6.5 Antimicrobial The antimicrobial role of EOs has been widely researched with the major drive coming due to the incessant emergence of antibiotic resistance around the globe. The antibacterial capacity of EOs is linked with potential of the membrane being reduced, proton pump interruption, and ATP depletion. These changes can result in a cascade effect impacting the cell organelles. Another research mentioned the changed cell permeability, deteriorated cellular respiration, and increased intracellular escape of K+ resulting in alteration of the growth pattern of E. coli and S. aureus (Aumeeruddy-Elalfi et al., 2016; Mehdizadeh and Moghaddam, 2018). Some bioactive constituents including thymol, menthol, and linalyl acetate also resulted in creating disturbances in lipid fractions, and with altered permeability, the intracellular materials escaped in E. coli and S. aureus. Gram-negative bacteria exhibit less sensitivity to the EOs as compared to their counterparts owing to cell wall structures (hydrophilic) that restrict the easy movement of hydrophobic compounds via the membrane of the cells (Burt, 2004; Tariq et al., 2019). Similarly, the role of EOs against Helicobacter pylori, has been widely researched with its impact against peptic, gastric ulcers, gastric cancers, and lymphomas. Additionally, Ocimum basilicum L. and Salvia officinalis L. were also researched to decrease the production of biofilm caused by P. aeruginosa strains (Percival and Suleman, 2014; Sharifi-Rad et al., 2018; Stojanovic-Radic et al., 2016). Moreover, the antifungal role of EOs of C. nardus has been observed against Candida species including C. albicans, C. Krusei, C. glabrata, C. tropicalis, Candida parapsilosis, and C. orthopsilosis. These EOs also helped in the disruption and removal of biofilms along with showing antifungal properties better than citronella (De Toledo et al., 2016). Furthermore, it was highlighted those mitochondria and cytoplasmic membrane are the primarily targeted sites for the anti-Candida EOs obtained from Anethum graveolene L. seeds. Other than

24

1. Essential oils in plants

membrane lesions and reduction in ergosterol concentration entering the plasma membrane damage. ROS formation was also observed after the mitochondrial dysfunction, as a key event in the death of C. albicans. Other antifungal contributions of thymol EO have been observed against Fusarium graminearum where the membrane is damaged by the lipid peroxidation and ergosterol biosynthesis (Gao et al., 2016; Kalagatur et al., 2018).

1.6.6 Antiviral The potential of EOs against the viruses has also been well researched. The antiviral role of eucalyptus EO, thyme, tea tree (>96%), and their monoterpenes (>80%) have been evaluated in vitro experiments against Herpes Simplex Virus 1 (HSV-1). The EO of Melaleuca species has also been virucidal with 99%, 92%, and 91.5% against M. armillaris, M. Leucadendron, and M. ercifolia. The free viral particles were rendered inactive in a dose-dependent way causing HSV-1 inactivation. A combination of different monoterpenes exhibited a 10 higher selectivity index and lower toxicity as compared to individual usage of monoterpenes ( Jugreet et al., 2020). Out of 62, 11 EOs contribute as an antiinfluenza virus (A/WS/33) by reducing the cytopathic symptoms (>30%). Anise, marjoram, and clary sage with linalool as a common compound exhibited approximately 52.8% antiinfluenza properties (Choi, 2018). Moreover, the antiherpetic properties of Thymus bovei Benth (TBEO) is also evaluated against HSV.2 in Vero cells (having HSV.2 infection) with significant preventive potential observed against HSV-2 replication mechanism. Molecular docking of geraniol, the active ingredient of TBEO highlighted that it acts as a contentious inhibiting agent by binding to the HSV-2 protease, a site used for making the replica of viruses. With acyclovir (ACV), it acts synergistically against HSV-2 highlighting its potency as an HSV-2 infection (Hassan et al., 2018; Treml et al., 2020). Another antiviral role was observed by carvacrol active ingredients, extracted from oregano EO against murine norovirus (MNV). It resulted in the losing the infectivity potential of cell culture by impacting the RNA and the capsid of the virus. Carvacrol inactivated MVV within 1 h of exposure along with capsids enlargement from 35 to 800 nm in diameter showing promising antiviral potential for treating MNV (Gilling et al., 2014; Ma and Yao, 2020; Sharifi-Rad et al., 2018).

1.6.7 Anticancer EOs have been tested for suppressing different cancers cell. Among these experimental models, sesquiterpene alcohols specially α-bisabolol (from chamomile and other plants) in EOs are considered as a potent inducer in glioma malignant cells of both the human and rats. Furthermore, the mitochondrial inner transmembrane potential and cytochrome C discharge from the mitochondria of malignant cells highlight apoptotic phenomena. Furthermore, research also indicated that α-bisabolol is nontoxic if the normal glial cell’s viability is not affected (Al-Dabbagh et al., 2019; Cavalieri et al., 2004). Camphene extracted from Piper cernuum EO also exhibited antitumor properties in melanoma cells. It triggered apoptosis by the initiation of the caspase 3 process and signaling of stress conditions in endoplasmic reticulum (Girola et al., 2015; Rodriguez-Vidal et al., 2020). Moreover, the carvacrol methodology

1.6 Applications of all essential oils

25

indicates that phenolic monoterpenes stimulated apoptosis by the mitochondrial permeabilization in the breast cancer cell line of the metastatic origin (MDA-MB-231), resulting in the release of cytochrome C, fragmentation of DNA, and caspase induction via the cleavage of poly ADP ribose polymerase (Aumeeruddy-Elalfi et al., 2016; Quintans et al., 2019). Additionally, Thymus bovei Benth. EO also demonstrated strong cytotoxic activity against the lung adenocarcinoma (A-549-C5), colon cancer (LS-174-D3), and human cervical carcinoma (HeLa-R2) with IC50 values 8.62, 9.30, and 7.22 μg/mL respectively (Hassan et al., 2018). Similarly, different other EO compounds have been used in combination with chemotherapy drugs to improve the cytotoxicity in different cancer cell lines. An example includes D-limonene in combination with the docetaxel sensitized prostate cancer cell line (DU-145) in a dose-depending manner. This combination also suggested a lower dosage of the chemotherapy drug in comparison to the existing usage amount ( Jugreet et al., 2020; Sundaram et al., 2013).

1.6.8 Cardioprotective The therapeutic role of different EOs has been promising against cardiovascular diseases (CVD). On treatment with thymoquinone, active substance of Nigella sativa L. a reduction in oxidative stress was observed in the abdominal aorta ischemia-reperfusion injury of the rats. Similarly, cinnamaldehyde also regulated activities as vascular contractile, prevent hypertension in insulin-resistant or deficient animals and inhibit the hypo-responsive attribute among vasodilatory agents (Acetylcholine). It is also reported to avert the hyperresponsivity to the vasoconstrictor agents (KCl/Phenylephrine) in the aortic rings (El-Bassossy et al., 2011; Zhu et al., 2017). A critical factor in cardiovascular failure and hypertension control is prevention of the angiotensin-converting enzyme (ACE). In this regard, an ACE inhibitor, captopril and geraniol, and EO from Thymus bovei were compared. Results indicated 95.4% and 92.2% of geraniol and EO from Thymus bovei correspondingly at 15 μg/mL significantly inhibited against ACE as opposed to captopril (99.8% at 15 μg/mL) (Hassan et al., 2018). Molecular docking further indicated the geraniol attachment to the ACE (active cavity) via H+ bonding (between the -OH of geraniol and ASP-415). Other cardioprotective examples include 1,8-cineole, with its antihypertensive properties displayed on rats exposed chronically to nicotine for hypertension induction. Oxidative stress and controlling nitric oxide were considered primary reasons for decreased blood pressure (Cai et al., 2020; Moon et al., 2014).

1.6.9 Neuroprotective A rising concern is reported owing to the severe side effects and dependency development of drugs used against different nervous illnesses. Owing to this, increased appeal in plant and plant-based constituents has also been acknowledged ( Jugreet et al., 2020). Antioxidant capacities of EOs have been employed in the treatment of free radicals-induced illnesses, neurological and age-related diseases. An example includes lavender essential oil’s application in CNS and stress, anxiety, cerebral ischemia, and depression management. It is also associated

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with increased cognitive and nervous system protective effects for Alzheimer due to its antioxidant potential (Xu et al., 2017). Another study exhibited the neuroprotective potency of Angelica sinensis and Sophora flavescens EO by increasing the defensive mechanism in cerebral ischemia in experimental rat models. This resulted in enhancing the antioxidant process for lesion pathogenesis by reducing the interleukin 1-β level; TNF-α, and oxidative induced stress. The ischemic injury was recuperated by the brain through the antioxidant homeostasis restoration after reperfusion (Li et al., 2012a, b; Porres-Martı´nez et al., 2013). Moreover, Citrus limon L. peel EO also exhibited a key impact on neurodegenerative conditions including butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) in vitro with dependency on concentration being used. The obstruction of BChE and AChE is associated with the oxidative stress-management induced neurodegeneration potential of EOs (Cutillas et al., 2017; Oboh et al., 2014; Olasehinde et al., 2020; Orhan et al., 2008).

1.6.10 Hepatoprotective Series of both in vitro and in vivo experiments have been ushered to verify the hepatoprotective capacity of EOs. The EO obtained from Achillea biebersteinii Afan was evaluated against the hepatotoxicity induced by CCl4 in rats using various markers. A significant decrease was observed in the increased hepatotoxicity-linked parameters with 0.2 mL/kg EO administration. These results synced with histopathological analysis. The hepatocytes from the counter section exhibited extreme necrosis and deterioration in hepatic lobules. Moreover, the hepatic malondialdehyde (MDA) obtained from lipid peroxidation in the nontreated rats was very high while the group pretreated with EO exhibited a clear decrease in the MDA proportions at the final stage (Al-Said et al., 2016; Daoudi and Bnouham, 2020). Another study involving the prior treatment of rats with EOs (50 mg/kg for 15 days) from Salvia officinalis and Thymus capitatus were exposed to paracetamol intoxication; indicated that EOs sheltered hepatic lactate dehydrogenase (LDH) and other serum pursuits. An increase of SOD and GPx in the blood and liver was also observed. The hepatoprotective role of EOs was associated with their antioxidation capacity (Banna et al., 2013; Bouyahya et al., 2020a).

1.7 Safety concerns The history of EO application in preservation, as a food additive, and in traditional toxicology has established the safety of their usage. Some are mixed with different volume of diluents that can result in the intoxication of the body or the skin. Different results on animals indicate the LD50 range of EOs from 1 to 20 g/kg body weight with few deviations. In the cosmetic industry, numerous applications in antiseptics, liniments, soaps, deodorant, flavors, and cosmetic ingredients are observed. Tea tree EO is used in devising hand washing liquids, antiseptics, and mosquito repellents in many countries owing to the monoterpenes and sesquiterpenes concentration present. Similarly, many EOs are employed widely in the mosquito repellent preparation, perfume and fragrance industry (Hashemi et al., 2017).

1.8 Conclusion

27

In agriculture, they are also used as natural pesticides without imparting toxicities. Some insecticidal EOs have also been researched to impede arthropodic neural network via GABA, octopamine synapsis, and the acetylcholinesterase inhibition (Isman, 2020; Regnault-Roger et al., 2012). In aromatherapy, they are absorbed via olfactory mucosa stimulating the limbic system. On interaction with the neuropsychological network, physiological and psychological effects are apparent. This therapy is associated with a positive contribution in labor, infections, dementia, and anxiety treatments; however, it still needs scientific validation. EO from rosemary is associated with hyperexcitability on cell stage owing to the loss of sodium or potassium gradient. Wound healing time reduction is also associated with the application of tea tree oil while lavender EO is linked to reduction in anxiety presurgery (Hashemi et al., 2017). Similarly, a cutaneous irritation study in human patients was also conducted with Clausena dentata resulting in no harmful impact on the human skin but with few side effects (De Souza et al., 2020; Rajkumar and Jebanesan, 2010). The eye safety aspect of EOs includes the usage of 5% tea tree oil for eyelid scrub treatment for nullifying Demodex infestation with improvement in subjective ocular symptoms. Another study supported the usage of tea tree essential oil for the reduction in eyelid scrub, Demodex infection in eyelids, and corneal pathological conditions along with conjunctival inflammation (Gao et al., 2012; Koo et al., 2012). Ophthalmic observation also highlighted that turmeric EO in rats at 1 g/kg consumed orally did not cause any constriction or retinal vessels branching in any treated groups. Therefore, oral administration of turmeric essential oil was ruled out for causing glaucoma and intraocular changes resulting in inflammation (Liju et al., 2013; Soleimani et al., 2018). Phototoxicity is chemically induced skin irritation due to light. Some EOs from lemon include furocoumarin resulting in causing phototoxicity. Compounds responsible for phototoxicity are identified as oxypeucedanin and bergapten. EO extracted from Tagetes minuta and patula are also phototoxic therefore not used in the preparation of sunscreen products. Moreover, some EOs can be carcinogenic if they are activated after metabolism. These if stimulated may induce the malignancy dependent on estrogen production. Usually, this antimutagenicity and mutagenicity are tested on bacteria, mammalian cells, and insects where the studies concluded that EOs can damage mitochondrial dysfunction and can result in respiratory deficient directly or indirectly (Hashemi et al., 2017). Multipurpose benefits of EOs have bagged acceptance globally but the toxicological studies have revealed that some constituents need to be evaluated carefully before legally marketing them for food or drugs. Therefore, in vivo experiments are needed to evaluate their toxicological status to enable further therapeutic, scientific, economic, and conventional applications (Hashemi et al., 2017).

1.8 Conclusion Among the numerous methods employed for the extraction of EOs, nonconventional ones have been evaluated for their recovery, short extraction time, and higher efficiency, especially ultrasound microwave, supercritical fluid, etc. Other advantages include the reduction in

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energy, wastewater, and solvent cost. However, further studies and experiments are needed to analyze the extraction efficiency of hydrophobic and hydrophilic bioactive agents. With various unique and complex chemical compositions, the EO with a biochemical mechanism of action against pathogen is specific against each pathogen. Permeability of the biomembrane, polarity, cytotoxicity, mitochondrial and genomic toxicity, or electrolyte loss are some likely causes for carcinogenic and antimicrobial effects. Further clinical research is needed to identify the dosage for triggering single or synergistic effects of EOs in food industries, or holistic medicines without imparting any dangers of triggering side-effects (both humans and animals).

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Winter, A.N., Brenner, M.C., Punessen, N., Snodgrass, M., Byars, C., Arora, Y., Linseman, D.A., 2017. Comparison of the neuroprotective and Antiinflammatory effects of the anthocyanin metabolites, protocatechuic acid and 4-hydroxybenzoic acid. Oxidative Med. Cell. Longev. 2017, 6297080. Wojtunik-Kulesza, K.A., Kasprzak, K., Oniszczuk, T., Oniszczuk, A., 2019. Natural monoterpenes: much more than only a scent. Chem. Biodivers. 16, e1900434. Xu, P., Wang, K., Lu, C., Dong, L., Gao, L., Yan, M., Aibai, S., Yang, Y., Liu, X., 2017. The protective effect of lavender essential oil and its main component linalool against the cognitive deficits induced by D-galactose and aluminum trichloride in mice. Evid. Based Complement. Alternat. Med. 2017, 7426538. Yamamoto, T., Yoshimura, M., Yamaguchi, F., Kouchi, T., Tsuji, R., Saito, M., Obata, A., Kikuchi, M., 2004. Antiallergic activity of naringenin chalcone from a tomato skin extract. Biosci. Biotechnol. Biochem. 68, 1706–1711. Yang, C.H., Huang, Y.C., Tsai, M.L., Cheng, C.Y., Liu, L.L., Yen, Y.W., Chen, W.L., 2015. Inhibition of melanogenesis by β-caryophyllene from lime mint essential oil in mouse B16 melanoma cells. Int. J. Cosmet. Sci. 37, 550–554. Yang, W., Chen, X., Li, Y., Guo, S., Wang, Z., Yu, X., 2020. Advances in pharmacological activities of terpenoids. Nat. Prod. Commun. 15, 1934578X20903555. Yildirim, A., Cakir, A., Mavi, A., Yalcin, M., Fauler, G., Taskesenligil, Y., 2004. The variation of antioxidant activities and chemical composition of essential oils of Teucrium orientale L. var. orientale during harvesting stages. Flavour Fragr. J. 19, 367–372. Yousefi, M., Rahimi-Nasrabadi, M., Pourmortazavi, S.M., Wysokowski, M., Jesionowski, T., Ehrlich, H., Mirsadeghi, S., 2019. Supercritical fluid extraction of essential oils. TrAC Trends Anal. Chem. 118, 182–193. Zhou, W., He, Y., Lei, X., Liao, L., Fu, T., Yuan, Y., Huang, X., Zou, L., Liu, Y., Ruan, R., 2020. Chemical composition and evaluation of antioxidant activities, antimicrobial, and anti-melanogenesis effect of the essential oils extracted from Dalbergia pinnata (Lour.) Prain. J. Ethnopharmacol. 254, 112731. Zhu, R., Liu, H., Liu, C., Wang, L., Ma, R., Chen, B., Li, L., Niu, J., Fu, M., Zhang, D., 2017. Cinnamaldehyde in diabetes: a review of pharmacology, pharmacokinetics and safety. Pharmacol. Res. 122, 78–89. Zini, C.A., Augusto, F., Christensen, E., Smith, B.P., Carama˜o, E.B., Pawliszyn, J., 2001. Monitoring biogenic volatile compounds emitted by Eucalyptus citriodora using SPME. Anal. Chem. 73, 4729–4735.

Further reading Hu, Z., Feng, R., Xiang, F., Song, X., Yin, Z., Zhang, C., Zhao, X., Jia, R., Chen, Z., Li, L., 2014. Acute and subchronic toxicity as well as evaluation of safety pharmacology of eucalyptus oil-water emulsions. Int. J. Clin. Exp. Med. 7, 4835. Liu, B.-B., Luo, L., Liu, X.-L., Geng, D., Li, C.-F., Chen, S.-M., Chen, X.-M., Yi, L.-T., Liu, Q., 2015. Essential oil of Syzygium aromaticum reverses the deficits of stress-induced behaviors and hippocampal p-ERK/p-CREB/ brain-derived neurotrophic factor expression. Planta Med. 81, 185–192. Menichini, F., Tundis, R., Loizzo, M.R., Bonesi, M., Provenzano, E., Cindio, B.D., Menichini, F., 2010. In vitro photoinduced cytotoxic activity of Citrus bergamia and C. medica L. cv. Diamante peel essential oils and identified active coumarins. Pharm. Biol. 48, 1059–1065.

C H A P T E R

2 Extraction and analysis of essential oils: Extraction methods used at laboratory and industrial level and chemical analysis Muhammad Modassar Ali Nawaz Ranjhaa, Syeda Mahvish Zahraa,b, Shafeeqa Irfana, Bakhtawar Shafiquea, Rabia Noreena, Umar Farooq Alahmada, Saba Liaqatb, and Saba Umara a

b

Institute of Food Science and Nutrition, University of Sargodha, Sargodha, Pakistan Department of Environmental Design, Health, and Nutritional Sciences, Allama Iqbal Open University, Islamabad, Pakistan

2.1 Introduction Essential oils are basically the liquids extracted from generic sources, either edible or nonedible. Essential oils have been in use since primitive times, especially for medicinal or fragrance purposes; these were removed with the most commonly used technique of that era, “Enfleurage” (Oktavianawati et al., 2019). Enfleurage is a method in which odorless oil of animal and plant sources are settled in a glass tray, petals of desired fragrant flowers are pressed on the fat layer, a rest of at least a week is provided; meanwhile, fragrance and phytoconstituents seep deeper into fat layer and extract later on retrieved with alcoholic washing of “enfleurage pomade” (fat layer with fragrance and bioactive components), it can be done using hot or cold fat (Soe’eib et al., 2017). Extraction is the process that involves mechanical or chemical inputs to collect aromatic or nonaromatic bioactive constituents of plant and animal originated substances (Rifna et al., 2021); nowadays, isolation and

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00021-9

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Copyright # 2023 Elsevier Inc. All rights reserved.

38

2. Extraction and analysis of essential oils

FIG. 2.1 Elaborated industry wise utilization of essential oils.

purification of these constituents involve advanced processing even integration of techniques for improved efficiency and effectiveness to retain improved yield and safety to chemical compounds being isolated and purified (Alexandre et al., 2017). Essential oils are now being used diversely almost in all aspects that can possibly touch any living organism’s life. The most important utilizations, which now have turned into industrial production due to immense demand, are displayed in Fig. 2.1.

2.2 Extraction, isolation, and purification methods of essential oils at laboratory level Separating natural aromatic and essential oils from raw materials is the first step in extraction, which is mainly applicable for different purposes, especially in the cosmetic, pharmaceutical, and food research and development laboratories. The quality of essential oils is generally proportionate to the method of extraction. Inappropriate extraction methods of essential oils can cause rancidity and physical change. Recently, various extraction techniques have been used with modifications in traditional forms ( Jiang et al., 2021). Here we will discuss some innovative ways of essential oil extraction, isolation, and purification methods at the laboratory level.

2.2 Extraction, isolation, and purification methods of essential oils at laboratory level

39

2.2.1 Innovatory extraction methods Extraction methods evolve due to several drawbacks in existing processes, which stimulate essential oils to undergo chemical changes such as hydrolysis and oxidation. Essential oils lose quality due to high temperatures, and extraction times are prolonged. As part of the extraction process for essential oils, it’s vital to keep the oils’ chemical composition and natural proportions at their original states. Innovative extraction methods must consider the extraction time, energy consumption, the solvent employed, and carbon dioxide emissions (Dhifi et al., 2016). 2.2.1.1 Supercritical fluid extraction (ScFE) The critical pressure (Pc) and critical temperature (Tc) are the most important when it comes to a supercritical fluid. Fluids with these critical characteristics have highly intriguing properties such as high low diffusivity, viscosity, and density closer to liquids. Carbon dioxide is used as a supercritical solvent for the extraction of essential oils due to its numerous attractive properties: (i) easily reach a critical point (low critical pressure, Pc: 72.9 atm, and temperature, Tc: 31.2°C); (ii) unaggressive for thermolabile molecules of the plant essence; (iii) chemically inert and toxic; (iv) nonflammable; (v) available in high purity at relatively low cost; (vi) easily eliminated; and (vii) its polarity similar to pentane which makes it suitable for extraction of lipophilic compounds. This process involves recycling and compressing/ decompressing a liquid repeatedly to obtain supercritical fluids. In this method, by heating and compressing the fluid, the supercritical state of CO2 can be achieved, which then passes through the plant sample to plant extract, followed by the decompression where the mixture of plant extract and CO2 is routed to two separators to obtain oil from CO2. The leftover CO2 is then recycled, and the final product is received with no residue left. Preliminary literature revealed that clove buds, rose, and caryophyllene are the best example of this technique. In comparison with hydrodistillation technique, this supercritical fluid extraction method is a more advanced technique in isolating essential oil to be used in the pharmaceutical industry. 2.2.1.2 Subcritical liquid extraction (SLE) Another compelling and alternative method of essential oil extraction is subcritical liquid extraction. Under critical pressure or temperature, a liquid is in a subcritical stage when it has reached a force higher than necessary pressure (Pc) but lower than critical temperature (Tc). In this method, water and CO2 are used to extract essential oils. Fluids in the subcritical state have superior properties, such as lower density, lower viscosity, and enhanced diffusivity between gases and liquids, due to their ability to isolate essential oils instantly at a low working temperature. Aside from that, it’s an eco-friendly and cost-effective process (Gomes et al., 2007). This method extracts essential oils in 15 min instead of 3 h using traditional methods. The essential oils, which contain more oxygenated components and no terpenes, can be obtained at a lower cost in energy and plant materials (Glisˇi
c et al., 2007). 2.2.1.3 Solvent-free microwave extraction (SFME) The solvent extraction technique is exacerbated by the damage of several evaporative components, improper isolation consistency, and poisonous solvent filtrates in the final product.

40

2. Extraction and analysis of essential oils

Solvent-free microwave extraction (SFME) was considered for various applications because of these challenges. As a result of this technique, it is possible to isolate essential oils from spices, aromatic herbs, and dry seeds in a short amount of time. According to researchers, SFME has the following advantages: to obtain essential oils with high yield and choosiness, shorter extraction time, and eco-friendly process. The following procedure is used in SFME: microwave heating of plant samples followed by dry distillation at optimal air pressure without a solvent. From preliminary literature, Oregano essential oil yields were determined by using the SFME method reported by Bayramoglu et al. (2008). According to the data, essential oregano oil produced the most excellent yields at 622 W, 498 W, 373 W, and 249 W power levels. Aside from the lowest microwave power (249 W), all results were higher (P < 0.05). This was about 6% less than the most excellent SFME oregano oil yield obtained via hydrodistillation, 0.048 mL/g. Further research by Ferhat et al. (2007) showed that the SFME approach was superior to standard methods in terms of extraction times and products, environmental effect, solvent residues content, and antibacterial activity. While hydro diffusion takes 3 h to complete the process, microwave extraction takes only 30 min; yields from SFME are much higher than those from hydrodiffusion at 0.21%, and SFME consumes less energy than hydrodiffusion. 2.2.1.4 Pulsed electric field extraction (PEFE) Using a pulsed electric field (PEF) to extract oil enhances the yield (Ranjha et al., 2021) and reduces the extraction time because it increases mass transfer by disrupting membrane structures during extraction. The efficacy of PEF treatment depends on various factors, including specific energy input, field strength, temperature, and pulse number. Also, nonthermal PEF extraction decreases thermolabile chemical disruption. After the PEF treatment (Bouras et al., 2016) observed that the phenolic content (8 times) and antioxidant activity (30 times) of the samples were substantially higher than the untreated ones.

2.2.2 Isolation and purification techniques of essential oils at laboratory level As a result of the complex nature of the components in the extract, further separation and purification are required to produce the bioactive products. Separation is based on the physical or chemical differences between the natural products in a given sample (Sasidharan et al., 2010). Several isolated and purified techniques for natural products are successfully implemented today. 2.2.2.1 High-performance thin layer chromatography (HPTLC) On high performance layers, natural substances are separated, and data is acquisitive by this method. A sorbent with a particle size of 5–7 μm is coated on precoated plates, which are 150–200 μm thick. Declining layer thicknesses and particle sizes improve plate efficiency and the nature of separation. HPTLC plates are a cost-effective alternative to standard chromatography plates. HPTLC plates are four to six times more expensive than standard chromatography plates (Aromatic, S. H.-E. Technologies for Medicinal, 2008).

2.3 Extraction, isolation, and purification methods used for essential oils at the industrial level

41

2.2.2.2 Optimum performance laminar chromatography (OPLC) Advantages of thin layer chromatography (TLC) and HPTLC are combined in this novel approach in the field of parallel chromatography. Research and quality control laboratories can use OPLC as both an analytical and a preparative technique. This technique is user friendly, powerful separation technique. OPLC uses a pump to drive a liquid mobile phase through a stationary phase, such as silica, similar to other chromatographic procedures. Planar columns can be used in the same way as stainless steel or cylindrical glass ones with the OPLC column housing structure. Solvent pumps drive the mobile phase through the column at constant linear velocity under high pressure of 50 bars (Ingle et al., 2017).

2.3 Extraction, isolation, and purification methods used for essential oils at the industrial level Due to the increasing demand for high profile and sophisticated perfumes, health-oriented functional foods, innovative drug delivery mechanisms involving pharmaceuticals, skin sensitive cosmetics, and environmentally safe paints, there has been a drastic change in extraction, isolation, and purification methods of essential oils. Essential oils, especially bioactive components, are being valorized by using agricultural wastes (Ranjha et al., 2020). Essential oils are being mostly used in emulsions of diverse functions in foods, i.e., flavoring agents. The composition of food changes its taste (Mahvish Zahra et al., 2020).

2.3.1 Extraction methods Extraction methods like maceration through stones in the old era to recent traditional use of motor grinders and sieving membranes (Ranjha et al., 2020) twisted to slightly upgraded versions of water or steam distillation, and simple solvent extraction, which are being discussed in this chapter. 2.3.1.1 Water distillation (hydrodistillation) Water distillation by heating is the traditional method for extracting essential plant oils (Wollinger et al., 2016). Firstly, rose petals essential oils were used to be removed and purified by this method. The procedure begins with the petals being immersed directly in water inside the alembic (vessel), and the entire mixture was boiled as displayed in Fig. 2.2. Heating source, decanter (to collect the condensate and different essential oils from water), condenser (to convert the vessel vapor into liquid), and vessel (Alembic) are all included in this set of devices. The oil droplets are surrounded by water that protects the extracted and isolated essential oil below 100°C, few examples have been displayed in Table 2.1. 2.3.1.2 Steam distillation Steam distillation is one of the traditional methods that are broadly applied for the extraction of essential oil. This approach extracts 93% of the essential oils, and the remaining 7% can be removed using alternative methods. Typically, for initiating the process, steam generators provide steam to generate heat. The amount of heat up to 100°C is significant in encountering

42

2. Extraction and analysis of essential oils

FIG. 2.2 Steam distillation to extract essential oils from plant materials.

TABLE 2.1 Isolation of essential oils by hydrodistillation. References

Extraction vessel

Extraction parameters

Extraction source

Veggi et al. (2011)

Vessel: 415 mL, H: 3.4 m, id: 0.01 m Vessel (SS): 415 mL, H: 3.4 m, id: 0.01 m

Time: 40
2 min; temperature: 323 K; gas: carbon dioxide Flow rate: 9.1  10–5 kg/s; temperature: 323 and 333 K; gas: carbon dioxide

Brazilian plants Myrciaria cauliflora

Cavalcanti et al. (2011)

Vessel: 290 mL

Time: 130 min—static mode; 360 min—dynamic mode; temperature: 313 K; gas: carbon dioxide

Clove

Prado et al. (2011)

Vessel: 150 mL

Flow rate: 0.5 g/min; temperature 40–60°C; gas: carbon dioxide

Sea buckthorn leaves

Sajfrtova and Sovova (2012)

HA 121-50-02 supercritical extraction unit

Flow rate: 2.0 L/h; temperature: 45°C; gas: carbon dioxide

Plant volatile oils

Chen et al. (2011)

ISCO SFE extraction system

Flow rate 1 mL/min/ 10 min—dynamic mode; temperature: 40–50°C; gas: carbon dioxide

Aquilaria malaccensis

Ibrahim et al. (2011)

Vessel: 125 mL, H: 300 mm, id: 23 mm

Flow rate: 3.2 kg/h; temperature: 35–60°C; gas: carbon dioxide

Algerian rosemary

2.3 Extraction, isolation, and purification methods used for essential oils at the industrial level

43

the decomposition of the plant to extract the essential oil. This method seems to have the advantage of being able to control the heat and prevent thermal breakdown. The downside of this method is its escalating capital expenditure needed to establish (Mongkholkhajornsilp et al., 2005). 2.3.1.3 Solvent extraction Solvent extraction is considered a viable alternative for essential oils that cannot be extracted by steam or heat. The solvents like petroleum ether, acetone, hexane, ethanol, and methanol are the typical solvents used to remove oils from plants (Chemat et al., 2019). Generally, plant samples are heated and mixed with solvents and then drawn by filtration and solvent evaporation. Resins or a mixture of essential oils, fragrances, and wax are the filtrates. A low-temperature distillation process dissolves necessary oils into the filtrate mixture by adding alcohol to the filtrate mixture. Aromatic absolute oil stays in the pot residue after distillation because alcohol absorbs scent and is dissipated. Due to the complex nature of the extraction process, this method is more expensive and more time-consuming.

2.3.2 Isolation and purification techniques of essential oils used at the industrial level As a result of the complex nature of the components in the extract, further separation and purification are required to produce the bioactive products. Separation is based on the physical or chemical differences between the natural products in a given sample (Sasidharan et al., 2010). Several isolated and purified techniques for natural products are successfully implemented today. 2.3.2.1 Thin layer chromatography (TLC) TLC is one of the most widely used planar chromatographic technologies applied in natural product research. The cheapest and simplest technique, column chromatography analysis, isolation, and parameter setup, may be done with this approach. Usually, the intermediate phase chromatography technique is comprised of two phases: stationary (silica or alumina) and mobile (organic solvents). Contrary to this, the Stationary phase (alkyl bonded silica or alumina) and a mobile phase (polar solvent like water, alcohol, etc.) are used in TLC (Rasul, 2018). 2.3.2.2 Column chromatography (CC) For the purification of crude plant extracts, column chromatography is among the most efficient methods. The stationary phase is packed in a column, whereas the mobile phase passes through this column with loaded extract in the stationary phase on its top. The mobile phase transports the natural products included in the mixture depending on the affinity strength to both fixed and mobile steps, respectively. Also, the isolated compounds are collected by mobile phase (Kemp, 1991).

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2. Extraction and analysis of essential oils

2.3.2.3 High-performance liquid chromatography (HPLC) Isolating natural products is made easier with this adaptable and efficient process. HPLC is gaining popularity in different fields, especially the food and pharmaceutical industries. Prior to using HPLC to identify a compound, a detector must first be chosen. Choosing stationary and mobile phases is dependent upon the degree of separation. C18 is the most commonly used solid phase in modern HPLC. Eluting analytes with high pressure (up to 400 bars) is required before they pass through the diode array detector (DAD). To identify analytes, a DAD examines the absorption spectra. The exciting feature of this method is to detect substances that are not volatile or disintegrate rapidly at high temperatures; HPLC is an excellent complement to gas chromatography (Kemp, 1991).

2.4 Chemical transformation After extraction, isolation, and purification of essential oils, some more advanced techniques have been described here to improve the traditional and conventional techniques outcome efficiency (Chemat et al., 2012; Zhang et al., 2018).

2.4.1 Supercritical fluid chromatography (SFC) The mobile phase in SFC is a supercritical fluid, and due to these supercritical fluids’ high diffusivity, high dissolving capacity, and low viscosity, SFC expresses the advantages of both GC and liquid chromatography (LC) (West, 2019). It is possible to achieve better separation with SFC because it uses a more extended column and smaller stationary phase particles than HPLC. SFC isolated those thermally labile compounds on which the GC technique is not applicable. There is a wide range of detectors that are compatible with SFC systems. For many years, SFC was employed to separate nonpolar natural products such as fatty acids, terpenes, and essential oils. By adding methanol and acetonitrile to the eluent increases the elution strength, has increased the interest of scientists to use SFC for the isolation of natural polar products.

2.4.2 Simulated moving bed chromatography (SMBC) Multicolumn SMB chromatography utilizes stationary phases and multiple columns (bed). The countercurrent rotation of the bed is computer-generated by revolving valves that intermittently switch the inlet (feed and eluent) and outlet of the bed (extract and raffinate). In addition to being an influential device for the significant separation of natural produces at an advanced level, the SMB process has the benefit of lesser solvent utilization over a smaller time period (Dong et al., 2020).

2.4.3 Ultrasound-assisted extraction (UAE) Sonication is termed ultrasonic-assisted extraction (UAE); it is a technique that uses ultrasonic wave energy in the extraction process (Chavan and Singhal, 2013). The ultrasound

45

2.4 Chemical transformation

TABLE 2.2

Essential oils (EOs) extraction by using ultrasound-assisted extraction.

References

Sonication parameters

Extraction time

Extraction source

Velickovi
c et al. (2008)

Temperature: 40°C

20–30 min

Salvia sp. EO

Sereshti et al. (2011)

Temperature: 25°C

10 min

Oliveria decumbens Vent EO

Abbasi et al. (2008)

Temperature: 40–60°C

45 min

Pomegranate seeds Eos

Hashemi et al. (2009)

Temperature: 70°C; sonication time: 12 min

28 min

Cumin seeds Eos

Sereshti et al. (2012)

Temperature: 32.5°C

10.5 min

Elettaria cardamomum Maton EO

L€ u et al. (2011)

Ultrasound frequency: 50 Hz; time: 30 min

5 min at 5000 rpm

Rhizomes Curcumae and Radix Curcumae

waves cause vibrational movements, which accelerate the dissolution and diffusion of the solute in a solvent solution, and the heat transfer increases, improving extraction efficiency. In addition to reducing extraction temperature and time, UAE has a low solvent and energy consumption. Thermolabile and unstable compounds can easily be extracted using UAE as shown in Table 2.2.

2.4.4 Microwave-assisted extraction (MAE) By using the dipole rotation and ionic conduction processes, microwaves create heat by coupling with compounds of polarity, such as water and carbon-based components in the plant matrix (Kaufmann and Christen, 2002). In MAE, heat and mass are transferred in the same direction, resulting in a synergistic effect that speeds up extraction and increases extraction yield. The use of MAE has many benefits, such as expanding the extract yield, dwindling thermal dilapidation, and selective heating of botanical material. With minimum use of organic solvents in this method, MAE is considered a green technology. These methods can be divided into solvent-free (for volatile compounds) and solvent-based (for nonvolatile compounds).

2.4.5 Enzyme-assisted extraction (EAE) While extracting natural products, the most significant barriers are the cell membrane and cell wall structure. As a result, the hydrolytic action of the enzymes on the cell wall and membrane constituents, as well as macromolecules inside the cell, the extraction efficiency of EAE will improve. In the EAE method, cellulose, amylase, and pectinase are commonly used (Nadar et al., 2018). A brief overview of various extraction technologies, conditions of process and how these impact yield has been given in Table 2.3. Taking example of Rosmarinus officinalis L.

46

2. Extraction and analysis of essential oils

TABLE 2.3 Compilation of the various extraction technologies and conditions for Rosmarinus officinalis L. Extraction techniques

Active component

Boutekedjiret et al. (2003)

SD

Presti et al. (2005)

References

Optimized conditions

Findings

EO

Solvent: Water vapor, temperature: 100°C

The extraction yield efficiency of EO was much better in terms of reduced duration as 80% of EOs was recovered by SD in 10 min whereas HD took 30 min for similar results

MAHD

Essential oil (EO)

Solvent: water: time: 15.5 min, power: 900 W

This approach showed similar results to HD and slightly lower quantified volatile fraction than UAE. still, MAHD was demonstrated to be a cleaner method with reduced extraction period and higher repeatability

Bousbia et al. (2009)

MHDG

Essential oil (EO)

Power: 1 W/g for 500 g of sample, time: 15 min, solvent free

This new method obtained the same yield as HD with 180 min. The suitable method was of significantly low cost as well as reduced carbon dioxide emission and energy consumption compared to HD

Ahmed et al. (2012)

SFE

EO

Solvent: CO2, pressure: 220 bar, temperature: 40°C, time: 3 h

The yields of EO was calibrated by manipulating the pressure and temperature conditions of SFE

Filly et al. (2014)

SFME

EO

Microwave power: 150 W for 150 g of sample, time: 30 min, temperature: 100°C, pressure: atmospheric pressure

Pilot-scale study had similar results to lab-scale study in terms of EO’s yields. The power consumption and extraction time were drastically reduced when compared to HD. Overall, study showed applicability of SFME in the industry

Oliveira et al. (2016)

Maceration

CA, RA, and carnosol

Solvent: 70% ethanol, solid-liquid ratio: 1:5 g/mL, time: 55 min

High concentration of the three compounds was obtained in the final extract. Additionally, the final extract contained higher antioxidant properties than the raw material

47

2.4 Chemical transformation

TABLE 2.3 Compilation of the various extraction technologies and conditions for Rosmarinus officinalis L—cont’d Extraction techniques

Active component

Iban˜ez et al. (2002)

SWE

Herrero et al. (2010)

References

Optimized conditions

Findings

CA, RA, carnosol, rosmanol, flavonoids, total antioxidant activity

Solvent: water, temperature: below 100°C for high polar compounds, 200°C for CA and similar compounds, time: 15–30 min

This method is highly effective for both polar and nonpolar compounds as the polarity properties of water can be manipulated by altering the temperature

PLE

CA, RA, carnosol, total antioxidant activity

Solvent: water (high to medium polarity compounds), ethanol (medium to low polarity compounds), temperature: 100–200°C, time: 20 min, solid-liquid ratio: 1:11 g/mL

PLE provided the best results on the basis of individual compounds and antioxidant activity. However, good results for varied polarity compounds were obtained separately

Bellumori et al. (2016)

UAE and MAE

CA, RA, carnosol, flavonoids, total phenols, total terpenoids

For UAE, frequency: 19.5 kHz, power: 140 W For MAE, multimode under N2 (2 MPa) at 100°C Solidliquid ratio: 1:10 g/mL and time: 10 min for both methods Solvents: acetone (for general recovery of CA and RA), n-hexane (specific for CA)

This study investigated multistage extraction with different solvent each time. Overall, it was concluded that acetone, in general, produced the best quality, whereas, n-hexane resulted in highest CA among all the solvents investigated

Liu et al. (2011)

Ionic liquid based microwave assisted simultaneous extraction

CA, RA and EO

For CA and RA Solvent: 1.0 M 1-octyl-3-methylimidazolium bromide, solid-liquid ratio: 1:12 g/mL, time: 15 min, power: 700 W For EO Solvent: water, solid-liquid ratio: 1:10 g/mL, time: 4 h, power: 700 W

The proposed two-step method of microwave pretreatment followed by MAE with IL resulted in simultaneous extraction of highest yield of RA and CA with reduced time. However, most yield of EOs were obtained with MHD

Zu et al. (2012)

Ionic liquid based ultrasound assisted simultaneous extraction

Solvent: 1.0 M 1-octyl-3-methylimidazolium bromide, solid-liquid ratio: 1:20 g/mL, time: 30 min, power: 220 W

The extraction efficiency of RA was improved by more than 40% by using ILs paired with UAE in comparison to 80% ethanol with maceration, heat flux, soxhlet, UAE, and stirring extraction. CA, however, was highest with 80% ethanol despite the extraction method implemented instead of IL Continued

48

2. Extraction and analysis of essential oils

TABLE 2.3 Compilation of the various extraction technologies and conditions for Rosmarinus officinalis L—cont’d Extraction techniques

Active component

del Pilar Sa´nchezCamargo et al. (2014)

Two-step SFE

Sa´nchezCamargo et al. (2016)

Mezza et al. (2013)

References

Optimized conditions

Findings

Extraction yield, TPC, total antioxidant activity, CA, and CR

Step 1 Solvent: neat CO2, time: 60 min, pressure: 300 bar, temperature: 40°C Step 2 Solvent: CO2 with 7% ethanol, time: 120 min, pressure: 150 bar, temperature: 40°C

The yields of CA and CR at the said conditions produced highly enriched fractions at step 2 after removal of waxes and oleoresins in step 1. Even though, the yields of CA and CR were similar to single step SFE, the twostep SFE has the additional advantage of reduced extraction time

SAF

TPC, TEAC antioxidant activity, CA, RA, and CR

Stage 1 (Raffinate) Solvent: CO2, feed: 20% (v/v) water, pressure: 300 bar, feed flow ratio: 0.025 extract/ SC-CO2, temperature: 40°C Stage 2 (Extract) Solvent: CO2, feed: 50% (v/v) water, pressure: 100 bar, feed flow ratio: 0.025 extract/ SC-CO2, temperature: 40°C

By optimizing the conditions through response surface methodology (RSM), the raffinate fraction was enriched with RA by 2.7-fold. The extract was enriched with CA and CR by twofold. Complete fractionation was not achieved as CA and CR were still detected in the raffinate fraction, here, it was noted that this was the maximum separation found in literature till date

MD

EO

Stage 1 and 2 Pressure: 0.078 bar, evaporation temperature: 12°C, feed flow: 0.02 mL/s, condenser temperature: 2°C, Motor speed: 200 rpm Stage 3 Pressure: 0.065 bar, evaporation temperature: 12°C, feed flow: 0.024 mL/s, condenser temperature: 2°C, motor speed: 200 rpm

Through the manipulation of the operating conditions, the concentrations of EOs in residue and distillate fractions can be changed

ASE, accelerated solvent extraction; ATPS, aqueous two-phase system; BAC, bioactive compounds; CA, carnosic acid; CR, carnosol; DES, deep eutectic solvent; EO, essential oil; EU, European union; GHz, Gigahertz; HD, hydrodistillation; MAE, microwave assisted extraction; MAHD, microwave-assisted hydrodistillation; MD, molecular distillation; MHDG, microwave hydro diffusion and gravity; PEF, pulse electric field; PLE, pressurized liquid extraction; RA, rosmarinic acid; RSM, response surface methodology; SAF, supercritical antisolvent fractionation; SD, steam distillation; SC, supercritical; SE, short-path evaporators; SFE, supercritical fluid extraction; SFME, solvent-free microwave distillation extraction; SWE, subcritical water extraction; TFE, thin film-evaporators; UAE, ultrasound-assisted extraction; UATPS, ultrasound-assisted aqueous two-phase system extraction; WHO, World Health Organization.

References

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2.5 Conclusion With passing by times, the valorization of essential oils has changed from traditional to exquisite forms; maximum advancement occurred in the 21st century when the concept of hygiene, health, and safety evolved at extensive self-care levels around the globe. The sensitivity to particles at cellular levels caused transformations in extraction, isolation, and purification of essential oils at the laboratory as well as industrial levels. Processing conditions change the impact of essential oils, which dictates suitable usage, be it in food products, cosmetics, fragrances, medicines, paints, furniture polish, body applications, and many more. Extraction, isolation, and purification of essential oils became sort of more concern when it found its applications as nutraceuticals, pain relievers, and analgesics; this inclined demand led to transform basic solvent extraction and steam distillation, and simple chromatography to more swift and efficient ultrasound-assisted extraction and super critical fluid chromatography techniques, even more enhancement is required to purify essential oils for better yet safe yield.

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C H A P T E R

3 Importance of essential oils and current trends in use of essential oils (aroma therapy, agrofood, and medicinal usage) Ajay Sharmaa, Khushbu Gumbera, Apurba Gohainb, Tejasvi Bhatiac, Harvinder Singh Sohala, Vishal Mutrejaa, and Garima Bhardwajd a

Department of Chemistry, University Institute of Science (UIS), Chandigarh University, Gharuan, Mohali, Punjab, India bDepartment of Chemistry, Assam University Silchar, Silchar, Assam, India cDepartment of Forensic Science, School of Bioengineering and Biosciences, Lovely Professional University, Phagwara, Punjab, India dDepartment of Chemistry, Sant Longowal Institute of Engineering and Technology, Sangrur, Punjab, India

3.1 Introduction Essential oils (EOs) or quinta essentia are the mixture of volatile molecules that have been extracted from different oil secreting glands of plants present in flowers, fruits, seeds, roots, leaves, barks and throughout the body of the plant (Irshad et al., 2019; Naeem et al., 2018). Researchers termed EOs as “the soul of plants” that makes up the odoriferous essence of plants. They are named according to their parent plant from which they are extracted and the odor of the oil also resembles the organ of that plant (Osuntokun, 2017). Schilcher, Hegnauer, and Cohn Richter presented a precise definition of these EOs which was further

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00002-5

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clinched by Sonwa (2000), they described it as a biochemical molecules or a mixture of similar molecules, formed in cytoplasmic fluid present in intercellular spaces as tiny odorous and volatile droplets. Another interesting definition is suggested by International Organization for standardization (ISO). They stated EOs as extract acquired from natural raw material, i.e., plant by steam distillation, mechanical extraction from the epicarp of citrus fruits or by physical extraction as dry distillation along with elution of the aqueous phase followed by post extraction physical study so that no variations in its composition may occur (Dhifi et al., 2016). EOs are known to be highly aromatic which are produced by different parts of the plants. Flowers, fruits, seeds, leaves, wood, bark, and roots of the plant contain the oil-secreting glands which produce essential oils. International Organization for Standardization (ISO) defined EOs as “extract obtained from raw material belonging to natural origin” like steam distillation in which mechanical extraction from the epicarp of citrus fruits or dry distillation and elution of aqueous phase and then postphysical analysis maintaining the same composition (Naeem et al., 2018). Approximately 3000 EOs that consist of complex mixtures of secondary metabolites are identified by the researchers. Their importance dates back to centuries where they were used due to their antioxidant, antiseptic and anesthetic properties. The presence of biologically active components makes EOs of utmost importance. They exhibit antibacterial, fungicidal, insecticidal, herbicidal, nematicidal, antiinflammatory, and antioxidant properties. Nearly 300 EOs are commercialized and utilized as a flavoring ingredient in food and beverages, as spices and in cosmetics (Raveau et al., 2020). These are used for the treatment of various infectious diseases and are widely utilized by variety of pharmaceutical industries to produce different bioactive formulations. EOs have also found their place in the treatment of cancer in recent years but their main usage is limited to food preservation, perfume industries and in aromatherapy (Irshad et al., 2019). Chemically, these EOs are blends of aromatic molecules or the mixture of aromatic and nonaromatic molecules. The foremost components of these are monoterpenes and sesquiterpenes, along with some carbohydrates, alcohols, ethers, aldehydes, and ketones. These are basically secondary metabolites that are imperative for the defense mechanism of the plants, and thus, have many biological properties as well (Tajkarimi et al., 2010). These are composed of traditionally significant molecules that have been used for medicinal, cosmetic, aromatic or pharmacological purposes but their advanced application gets boost from 19th century onward (Carpena et al., 2021; Raveau et al., 2020). These are also said to have the least adverse effects with the recommendation from the US Food and Drug Administration (Bilsland and Strong, 1990). The chemical profiles of these EOs are determined on the basis of species, season and collection area or the methods of extraction and solvents (Carpena et al., 2021). Though they have long lasting list of applications in almost all biological fields but their little unstable nature and susceptibility to degrade on exposure to environmental stress like temperature, oxygen, and light, etc., makes it difficult to utilize it to their fullest. To overcome these drawbacks, the scientists are making attempts to find out the solutions for the same. One of the trending outcomes of all these efforts include, the method of preservation of these essential molecules by encapsulation in different colloidal structures such as nanoemulsions, microcapsules, nanospheres, molecular inclusion complexes and liposomes. This chapter therefore, emphases on the major applications of EOs with their mode of action, new trends in the field and potential techniques used for the enhancement of their activities.

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3.2 Aromatherapy Use of EOs as a major therapeutic agent for the treatment of various diseases is the main idea of aromatherapy which is widely growing all around the globe. It gives relief of stress and pain cause due to indigestion, depression, muscular pain, headache, or any other skin ailment. These oils are gaining popularity in treatment of sleep disorders and cancers. Aromatic cleaning products of personal care and hygiene are increasing in market like soaps, cosmetics, perfumes, air and room fresheners, etc., tea tree oil, peppermint, rosemary, lavender, and lemon are the most popular around the globe. Lavender and rosemary essential oils are widely utilized specifically for the purpose of aromatherapy (Worwood, 2000; Pearson et al., 2019; Lizarraga-Valderrama, 2021). Aromatherapy is amalgamation of aroma and therapy that means utilization of fragrance or smell of the EOs for the treatment of a disease. It is natural mode of soothing a person’s body, soul, and mind. The technique has been used since ancient times in India, China, and Egypt as a prevalent harmonizing and unconventional therapy (Worwood, 2000; Pearson et al., 2019; Lizarraga-Valderrama, 2020) and came back into use after reinterpretation of the antiseptic properties of EOs by the scientists. These EOs are generally employed by inhalation, application, and baths in aromatherapy that helps in penetration of the oil into the human skin surface. When oil enters the system, it remodulates itself to act in a pleasant manner at required site or over an affected area. The actual site of action for these EOs is brain that gets an active response through the olfactory nerves (Lai et al., 2011; Wray, 2011). They are so potent and concentrated, that they act directly on the pressure points to rejuvenate (Ali et al., 2015). Their stimulating action lay in their structure that resembles very closely to the actual hormones (Ali et al., 2015) and their effects are multifaceted and elusive owing to their complex structure (Lizarraga-Valderrama, 2020). Fig. 3.1 represents the different fields of utilization of essentials oils in aromatherapy.

FIG. 3.1 Various fields of aromatherapy involving the use of essential oils.

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EOs, such as eucalyptus oil, can be used as inhalants, orally as peppermint oil, gargles or mouth rinses as thymol oil, lavender oil, and rosemary oil are also used as aromatherapeutic agents. These are also utilized as a stimulator to the brain in psycho-aromatherapy. Several oils exhibit soothing and relaxing effects, whereas others are stimulating and therefore can help reduce anxiety. The inhaling of EOs gave resulted in improved emotional wellbeing, serenity, relaxation, or revival of the human body (Pearson et al., 2019). Also, massage using grape seed, almond, or jojoba oil has been found to have excellent outcomes. The use of EOs in face cosmetics can result in healthier skin. This therapy makes use of EOs in skin care products such as body, face, and hair for like cleaning, moisturizing, drying, and toning purposes (Pearson et al., 2019). Cosmetic aromatherapy involves the use of EOs in cosmetic products for skin, face, body, and hair. These oils act as a good ingredient for all the cleansing, toning, and moisturizing cosmetic produces. Little amount of the appropriate oil provides a rejuvenating and revitalizing experience to whole body (Ziosi et al., 2010). The effect of almond, grape seed, jojoba, or any pure vegetable oil during massage said to add a healing touch in the therapy (Chang, 2008; Soden et al., 2004). Medical aromatherapy is another modern field in which EOs are used to massage patients during surgery and for treating clinically diagnosed medical ailments (Maeda et al., 2012). These EOs help in curing many neurologic diseases, mood disturbances, and pain. The potential effects of EOs are boon in handling pain in fragile patients for whom the other drugs lead to many side effects (Achterberg et al., 2020). The olfactory aromatherapy involves the inhalation of EOs to enhance emotional wellness, relaxation, calmness, or rejuvenation of the human body. The release of stress is also bonded with pleasurable scents (Ali et al., 2015). In psychoaromatherapy also moods and emotions can be altered with the help of these EOs giving the pleasure of relaxation, invigoration, or a pleasant memory. They infused in the room of the patients for inhalation leading to direct action on the mind. Various popular plants used in aromatherapy are listed below.

3.2.1 Eucalyptus EOs of Eucalyptus plant is mainly used for treatment of muscle pains, joint pains, and rheumatoid arthritis. Its major chemical constituents are cineole, aromadendrene, terpinene, pinene, limonene, cymene, and phellandrene that are responsible for the regulation and activation of various systems of body such as nervous system for curing headache, neuralgia, and debility. It provides immunity to the immune system against flu, measles, chickenpox and cold. Also, it can be used for the treatment of cuts, wounds, herpes, burns, and as an insect repellent (Ali et al., 2015).

3.2.2 Lavender The major chemical constituents of lavender are terpinene-4-ol, camphor, linalool, betaocimene, and linalyl acetate responsible for the treatment of the diseases. Linalyl acetate and linalool are characterized by high absorbing properties and sedative effects therefore known to cure depression and for relaxing body. The EOs of lavender are widely used to

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treating burns, abrasions, headache, stress, skin diseases, pain in muscles, and also promote new cell growth and immunity (Kim et al., 2011).

3.2.3 Lemon Lemon contains about 90% of the terpenes, limonene, and D-limonene. It has antiseptic, detoxifying, and astringent properties. In aromatherapy it is used to relieve the first stage labor pain in women. Apart from the aforementioned uses it is used to brighten the skin and to remove blemishes also. Also, it is an immunity booster as it accelerates the white blood cells production. Various digestion problems such as acidity, ulcers can be treated by using lemon as it produces carbonates and bicarbonates of calcium and potassium. Nausea and vomiting are also treated by using this essential oil (Yavarikia et al., 2014).

3.2.4 Rosemary Rosemary belongs to the family lamiacease having three varieties characterized by their green, gold, and silver stripe. The green one is widely used for medicinal purposes and in cosmetic aromatherapy for soothing and brightening skin. The major constituents are resin, volatile oil and tannic acids and the active components comprises of bornyl acetate, esters, camphor, borneol, cineol, camphene, and pinene. The rosemary oil is recognized for soothing menstrual cramps and stimulating hair growth. Medically, it is also utilized for treating indigestion, constipation and for the proper functioning of the gall bladder and liver. Cardiovascular action is also displayed by the EOs of this plant as it balances the blood pressure and stops the hardening of arteries (Atsumi and Tonosaki, 2007; Nabavi et al., 2015; Svoboda and Deans, 1992).

3.2.5 Tea tree Tea tree (Melaleuca alternifolia Cheel) belongs to the family of Myrtaceae contains EOs with major constituent such as terpinene-4-ol. It has recently found its various applications is cosmetic and medicinal aromatherapy to treat abscess, acnes, blisters, burns, cold, herpes, dandruff, oily skin, and sores. It displays antiviral, antibacterial, and antifungal activity. Various respiratory disease treatments such as tuberculosis, asthma, whooping cough, and bronchitis also utilize tea tree oil. Also, it is used to treat various female genital infections and as an immunity booster and as an antiseptic. It has recently found its various applications is cosmetic and medicinal aromatherapy and is widely utilized around the globe and studied by the researchers (Koh et al., 2002; Pazyar et al., 2013). There is a huge opportunity in the aromatherapy industry that in turn contributes toward the economy of the country. However, keep in mind that not all EOs are suitable to use in aromatherapy. In concentrated form, several of the oils can cause significant rashes or even harm the mucosa and stomach lining (Ali et al., 2015). To further understand the benefits of this treatment on human brain and emotions, numerous studies are under process. Some researchers tried to explore the effects of this therapy on human efficiency, time of action, and some natural responses through electroencephalograph patterns and functional imaging

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TABLE 3.1 Important plants used in aromatherapy and their key phytoconstituents (Ali et al., 2015). Plant species

Important component

Clary sage (Salvia sclarea Linn.)

Geranyl, germacrene D, linalool, linalyl acetate, and alpha-terpineol

Eucalyptus [Eucalyptus globulus Labill (E. globulus)]

Cineole, limonene, aromadendrene, cymene, pinene, terpinene, and phellandrene

Geranium (Pelargonium graveolens L’ Herit)

Eugenol, citronellol, geranic, geraniol, linalool, citral, citronellyl formate, terpineol, sabinene, methone, and myrtenol

Lavender (Lavandula officinalis Chaix.)

Linalyl acetate, camphor, terpinen-4-ol, linalool, betaocimene and 1,8-cineole

Lemon [Citrus limon Linn. (C. limon)]

Terpenes, limonene, phellandrene, pinene, and sesquiterpene

Peppermint [Mentha piperita Linn. (M. piperita)]

Carvacrol, carvone, menthol, methyl acetate, menthone, and limonene

Roman chamomile (Anthemis nobilis Linn.)

Pinocarvone, bisabolol, farnesol, cineole, pinene, pinocarveol, betacaryophyllene, camphene, azulene, and myrcene

Rosemary (Rosmarinus officinalis Linn.)

Bornyl acetate, borneol, cineol, pinene, camphor and camphene

Tea tree (Melaleuca alternifolia Cheel)

Terpinen-4-ol, and alpha-sabine

Ylang–ylang (Cananga odorata Hook. F. & Thoms)

Geranyl acetate, geraniol, linalool, benzyl acetate, geranial, farnesol, eugenol, methyl chavicol, betacaryophyllene, pinene, and farnesene

studies. All the important plants used in different types of aromatherapies along with their important components are shown in Table 3.1.

3.3 Agrofood uses The other important field involving the use of EOs is that of agriculture and food industry (Bhavaniramya et al., 2019). It is one of the most important arenas to be focused to meet the food demand of the rising population. The major problem that needs to combat is the overuse of pesticides and preservatives with some green substitute to intensify the yield and shelf life of the food and agricultural crops. This industry is unceasingly growing with the application of novel tools and ingredients to bring an effective, benign, natural, and eco-friendly solution to satisfy the demands of the consumers (Thielmann et al., 2019). EOs are one of the safe and effective alternatives to the existing harmful molecules. The application and evolving trends of using these EOs are explained below.

3.3.1 EOs as green pesticides The pesticides utilized over the crops every year were assessed to be almost 2.5 million tons and the annual global harm instigated due to pesticides is about 100 billion dollars. Pesticides

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based on EOs could be utilized in a variety of ways to control these enormous ranges of pests (Mohan et al., 2011). The green methods bring out the new crop protection tools with novel modes of action makes discovery and commercialization of the existing natural products as green pesticides. These pesticides are eco-accommodating, target-explicit, and economic. The “green pesticides” are now emerging as a powerful tool in many agricultural fields especially for organic food production (Mohan et al., 2011; Mossa, 2016). They show wide spectrum of activity against different agricultural pests and fungi making them a decent insecticide, repellent, antifungal, antifeedant, oviposition deterrent, growth regulators, and antivectors. The development of resistance is always a major concern for many synthetic pesticides but this obstruction development seems to be slow against in the case of EOs based pesticides attributable to the complex combinations of constituents (Mohan et al., 2011; Mossa, 2016). Robu et al. (2015) named these EOs as “reduced risk pesticides” that have been used from quite long for the protection of stored products, in view of their antimicrobial and antifungi activity which disrupts the octopaminergic nervous system of insects. These target sites of insects are not common to mammals, and therefore moderately toxic to mammals. Studies by Banani et al. (2018) reported the wide spectrum bio-potential of EOs against the different plant pathogenic fungi. As Botrytis cinerea is repressed by EO from black caraway and fennel whereas no effect of peppermint oil is visible against the test fungi (Aminifard and Mohammadi, 2013). These results are owed to the presence of phenolic (fennel EOs) or aromatic system (black caraway) in the molecule that seems to influence the activity against B. cinerea. The effectiveness of thyme and savory EOs were also inspected against B. cinerea in apple fruit (Banani et al., 2018). Similarly, Aspergillus sp. was vulnerable to EOs of lemongrass, oregano, thyme, and clove but not to ginger and cinnamon oil. Penicillium digitatum is extremely affected by summer savory as well as thyme EOs but not much by sweet basil and fennel (Ortiz de Elguea-Culebras et al., 2016). Another study showed that phytopathogenic fungi affects cereal production to a great extent and leads to enormous mycotoxins causes negative effects on humans and animals. Morcia et al. (2011) reported the use of more than 23 million kg per year of chemical-based fungicides in the Western and developing countries. In such cases, the usage of EOs would be quite beneficial. The compatibility analysis between essential oil and pesticides in chili peppers, beans, and eggplants to project more sustainable strategies for the production of agro products. According to the physicochemical and microbiological indicators of soil, insect, disease incidence, and crops, the combination of oils is more beneficial than the discrete effect of each product (Mena-Rodrı´guez et al., 2018). The consequence of bio-fumigation, through slow-release diffusors of thyme and savory EOs were also evaluated as an effective strategy for the control of postharvest diseases as well as to improve the quality of peaches and nectarines. The application of these EO decreases the brown rot incidence instigated by the Monilinia fructicola (Santoro et al., 2018) The new trend involved the use of bio- or nano-composites for increasing the efficacy and improving the life span of the existing essential oils. On the same line, Tolen et al. (2017) utilized the antimicrobial properties of eugenol loaded over surfactant micelles to reduce the O157 and non-O157 Shiga toxin-producing E. coli (STEC) infection in beef. Many EOs are already in commercial use owing to their great bio-potential. Table 3.2 lists some commonly used EO based commercial crop protection products.

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TABLE 3.2 Commercial products based on EOs for crop protection (Bhavaniramya et al., 2019). Source of EOs

Brand name

Allium sativum

GC-3

Azadirachta indica

Trilogy

Gossypium hirsutum

GC-3

Melaleuca alternifolia

Timor, Timorex

Mentha

Fungastop

Reynoutria sachalinensis

Milsana

Rosmarinus officinalis

Sporan

Rosemary, thyme, and clove oils

Sporatec

Sesame

Organocide

Simmondsia californica

E-Rase

Thymus vulgaris

Promax

3.3.2 Utilization of EOs as food preservatives The other important field is that of food preservatives. Food preservation is the process of prolonging the life of food while maintaining its safety as well as nutritional quality. The storage life of a food item has been defined as the time span over which it will remain unaffected. The storage life of a food is characterized by its physical, biochemical, and microbiological properties. EOs have also been used as natural antimicrobial and antifungal agents as a preservative for food products such as fruits, vegetables, and sea food (Naeem et al., 2018). Synthetic preservatives were traditionally being used for many years but their ingestion known to add some allergic properties, cancer, degenerative diseases, and other intoxications (Adelakun et al., 2016). Thus, EOs the “natural food additives” have proven are good alternatives for the synthetic preservatives (Odak et al., 2018; Turek and Stintzing, 2013). The EOs are said to be “natural food additives” for the process of preservation. They have multiple target actions (Braga et al., 2006). The novel synergistic effect of these EOs with different nanocarriers is another evolving trend of food industry. The hydrophobic nature of EOs makes them cross the lipid cell membranes of bacteria along with disruption of the cell wall followed by the leakage of ions and other cellular materials leading to the cell death (Abers et al., 2021; Cosentino et al., 1999). Due to the presence of volatile terpenoids and phenolics, EOs inhibit the wide spectrum of microorganisms mediated by disturbing the cytoplasmic membrane, altering the active transport of electrons, and inhibiting protein synthesis. Also, oxidation of fats in food that are rich in polyunsaturated fatty acids usually leaves the food rancid that renders the food unfit for human consumption. The utilization of active packaging materials with antioxidant features has the potential to improve food quality and minimize rancidity. The EOs extracted from the Zataria multiflora, Satureja hortensis, and Mentha pulgium when used for polymer base

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packaging systems exhibit the antimicrobial and antioxidant properties (Fisher and Phillips, 2008). Likewise, the EOs, viz., oregano, mint, murta, ginseng, gingko leaf green tea, rosemary, basil, thyme, sage, citronella possess antimicrobial and antioxidant properties. The EOs of spices, such as clove, lavender, and cinnamon, possess antimicrobial and antifungal properties (Valdes et al., 2015). In addition, edible coatings fused with cinnamon and ginger oil improved the safety and nutritional value of food. Gon˜i et al. (2009) validated the antimicrobial potential of the clove and cinnamon EOs vapors against the growth of four Gram-negative (E. coli, Pseudomonas aeruoginosa, Yersinia enterocolitica, and Salmonella choleraesuis) and Gram-positive bacteria (S. aureus, Bacillus cereus, Listeria monocytogenes, and Enterococcus faecalis). This proved that mixture of various essential oils in the vapor phase also have a great potential of preservation against microorganism proliferation. Twelve EOs (pine, thyme, eucalyptus, orange, sage tea, laurel, myrtle, lavender, lemon, juniper, and rosemary) were tested by disc diffusion method against pathogens borne in food (E. coli, Klebsiella pneumoniae, Salmonella paratyphi A, P. aeruginosa, Y. enterocolitica, A. hydrophila, E. faecalis, Campylobacter jejuni, and S. aureus). Lemon EOs contain oxygenated terpenes that have antifungal properties and exhibit the growth of fungi like C. tropicalis, C. albicans, and C. glabrata (Bhavaniramya et al., 2019). The overall results indicated that most of these EOs showed strong antibacterial activity toward one or more strains. The pine and thyme essential oils are highly effective against food borne pathogen, with large zones of inhibition for both the gram positive and negative bacteria (Ozogul et al., 2015). In another study, EOs of tea tree, cinnamon, clove, mustard, thyme, oregano, lemon, lavender, peppermint, and eucalyptus were exploited for the study of their dynamic role in the inhibition of microbial pathogenic growth along with food preservation (Bhavaniramya et al., 2019). Also, the EOs of other plants, viz., Origanum vulgare, Rosmarinus officinalis, Salvia officinalis, Mentha piperita, Foeniculum vulgare, Allium sativum, Satureja Montana, Thymus vulgaris, and Coriandrum sativum seeds, assessed from Abruzzo territory were found to have strong antimicrobial and antioxidant activities. Gram-positive and Gram-negative strains were utilized for the screening of the antimicrobial activity of these molecules. The results indicated that these essential oils are decent alternatives for prospective use as bio-preservatives in food industry (Pellegrini et al., 2018). Olmedo et al. (2013) estimated the efficacy of oregano and rosemary EOs on the oxidative and fermentative steadiness of flavored cheese. These results are owed to the protective effect of EOs against lipid oxidation and fermentation in cream-based cheese. The efficacy of fennel EOs presented the potential cytotoxic activity of the selected EOs against several cancer cells, which is very significant for its probable application in food products. On the other hand, the properties of EOs from a culinary component broadly used all over the world (garlic) has also been evaluated (Sharopov et al., 2017). In addition, EOs of four Thymus species focuses on the organic growth of food products leading to their possible applications to organic food industries (Ballester-Costa et al., 2017). Tyagi et al. (2014) stated the use of eucalyptus essential oil as a potent antimicrobial molecule against food spoiling yeasts. The structure elucidation of various components of eucalyptus oil supported the presence of oxygenated monoterpenes as an important source of efficacy. The amalgamation of eucalyptus EO with thermal treatment repressed the growth of yeast (Saccharomyces cerevisiae) in fruit juices and mark the eucalyptus oil as antimicrobial agent that provides applications in the beverage industry (Tyagi et al., 2014). In another study,

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Sendanyoye (2018) also reported the potential of EOs from two different eucalyptus spp. viz. Eucalyptus grandis and Eucalyptus crebra in food preservation. The pests involved in the study to evaluate the effectiveness of these essential oils are Acanthoscelides obtectus and Stophilus oryzae against Phaseolus vulgaris and Sorghum condatum, respectively. Rhizopus nigricans was used for bread and cooked Ipomoea batatas. The results indicated that these EOs have a strong potency as insecticide for storing of P. vulgaris and Sorghum condatum. Work reported by Irshad and coworkers also explained the significant effect of Eucalyptus oil as flavoring agents and its efficacy in understanding the development of pathogenic and food spoilage microorganisms (Irshad et al., 2019). The antimicrobial potential of cinnamon essential oil and their components were studied by Nowotarska et al. (2017). The results indicated a strong inhibition of the growth of Mycobacterium avium subsp. paratuberculosis (Map) that infect food, animals and humans and also found present in milk, cheese, and meat. Azadirachta indica and Litsea cubeba EOs were recognized as new potential antimicrobial agents with strong efficacy against the foodborne bacteria viz. S. aureus and E. coli (Thielmann et al., 2019). This EO of L. cubeba is cheaply available with broad spectrum antimicrobial effect owing to its unique and refreshing aroma (Li et al., 2014; Liu and Yang, 2012). The active ingredient of L. cubeba EO is citral, a monoterpene that is found to have an optimistic sensory effect when utilized as an antimicrobial agent for food products (Muriel-Galet et al., 2012). Nardostachys jatamansi and A. indica, important traditional Indian plants, are also interesting and safe molecules for their use in food preservation (Chauhan et al., 2017). The EO obtained from A. indica, also known to be neem-tree oil, consists of two main compounds Azadirachtin and Nimbin. These compounds are found to have a strong antimicrobial potential and is also a known commercial spermicide (Negi, 2012). Kaliamurthi et al. (2019) explained the advances in utilization of EOs with lipid based nanocarriers, functionalization or encapsulation with an application in food preservation with especial reference to grains, rice, and flour against the important microbes. This study advocates the use of special EOs obtained from organic aromatic herbs and spices as potential food preservatives.

3.3.3 Presence of EOs in packaging materials Packaging is essential for protecting food products from the environmental degradation and is intended to ensure food safety as an important industrial and consumer need. Active packaging materials are characterized by incorporating constituents with strong biological potential that are slowly released into the food products. Also, as per the Regulation 1935/2004/EC and the Regulation 450/2009/EC, the active packaging with effective biomaterials is referred to as “materials and articles that are proposed to prolong the shelf-life or to preserve or improve the condition of packaged food” (Carpena et al., 2021). These active packaging materials consist of certain antimicrobial reagent that increases the shelf life without compromising with its quality of food. The demand for EOs as active ingredients for this is quite high due to continued consumer preference owing to their extraordinary antimicrobial and antioxidant properties (Kouhi et al., 2020). Currently, application of EOs in active packaging of food is strongly allied to their assimilation in the biodegradable films in amalgamation with other polysaccharide-protein or

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lipid-based edible films (Mohamed et al., 2020). Hassan et al. (2018) reported the expansion of composite or multicomponent films to yield the advantage of EOs for their valuable properties. Researchers reported the antimicrobial effect of several EOs in culture medium on strains of lactic acid-producing bacteria. The technique was further elaborated over edible films and found to be worth consideration. The other promising option to promote the activity of these EOs is that it may be included into the packaging material as encapsulated compounds that can ultimately lengthen the shelf-life of the food material by preventing the spoilage. The chosen materials for food packaging material should have less viscosity, more hygroscopicity along with good emulsifying capacity, low reactivity, low cost, and with no effect on organoleptic properties of the packed food (Blanco-Padilla et al., 2014; Zhu et al., 2012). SC-based edible layers amalgamated with ginger and cinnamon EOs efficiently protected sunflower oil against oxidation leading to the low permeability of oxygen at lower relative humidity of the atmosphere. But the method considerably affected the optical properties of SC films in case of ginger oil, leading to the increase in the surface coarseness with loss of gloss due to the accumulation of lipids in the film (Atares et al., 2010). The overview of various essential oils incorporated in packaging materials is presented in Table 3.3.

TABLE 3.3

EOs and packaging materials.

Essential oil

Packaging material

Anise essential oil

Chitosan

Basil essential oil

Chitosan (Zivanovic et al., 2005)

Bergamot essential oil

Chitosan (Gutierrez et al., 2010); Gelatin film (Ahmad et al., 2012)

Cinnamon essential oil

Polypropylene and polyethylene-polyvinyl alcohol copolymer (Go´mez-Estaca et al., 2009) Polypropylene wrapped with polyethene/ethylene vinyl acetate (Gutierrez et al., 2010) Polyethylene terephthalate/polypropylene (Montero-Prado et al., 2011) Cellulosic films and paper (Espitia et al., 2011)

Clove essential oil

Paper packaging (Rodriguez-Lafuente et al., 2010); chitosan (Hosseini et al., 2008), fish skin gelatin (Go´mez-Estaca et al., 2009), active paraffin based paper (Rodriguez-Lafuente et al., 2010)

Lemon grass essential oil

Cellulosic films and paper (Espitia et al., 2011) gelatin film chitosan (Ahmad et al., 2012)

Oregano essential oil

Chitosan (Zivanovic et al., 2005), whey protein films (Seydim and Sarikus, 2006), PP and PE/ EVA copolymer coating (Vu et al., 2011), modified chitosan, active paraffin- based paper (Rodriguez-Lafuente et al., 2010), cellulosic films and paper (Espitia et al., 2011), LDPE

Rosemary essential oil

Whey protein films (Seydim and Sarikus, 2006), coextruded bionented PP film, chitosan modified (Abdolahi et al., 2010)

Red thyme essential oil

Modified chitosan (Vu et al., 2011)

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3.4 Medicinal uses Considering the exceptional therapeutic qualities, EOs play a significant role in the medical sector. Several EOs can be utilized as therapeutic agent as fungicidal, antidepressant, antibacterial, antiviral, anticancer, etc., due to their bioactive phytoconstituents that mainly consists of terpene hydrocarbons (consisting of 80% monoterpenes) and oxygenated compounds of alcohols, aldehydes, esters, and phenols. Pathogenic (caused by bacteria, viruses, or fungus) and nonpathogenic disorders are both treated using EOs. Various EOs were screened for their pharmacological potentials and have been discussed in detail below.

3.4.1 Antioxidant Oxygenated monoterpenes like as esters, aldehydes, and ketones are abundant in EOs derived from traditional plants such as Ziziphorac linopodioides, Achillea filipendulina, Anethum rutifolia, Galagania fragrantissima, Anethum graveolens, Hyssopusseravschanicus, and Mentha longifolia (Bhavaniramya et al., 2019). In addition, the EOs from Nigella sativa seeds is a strong antioxidant in vitro, having excellent hydroxyl radical scavenging. Kanuka (Kunzea ericoides), Manuka (Leptospermum scoparium), and Leptospermum petersonii exhibit antimicrobial and antioxidant effects (Amorati et al., 2013). The EOs of Megalaima armillaris has a strong antioxidant activity. Their activity is linked to the existence of phenolic acids, which have substantial redox characteristics as well as serve essential roles in free radical neutralization and peroxide breakdown.

3.4.2 Antibacterial EOs play an important role against various bacterial infections due to the presence of major compounds, namely, cinnamaldehyde, citral, carvacrol, eugenol, thymol, etc. EOs are shown to inhibit both Gram positive and Gram-negative bacteria. However, the antibacterial action of EOs differs with variety of pathogenic bacteria. For instance, Manuka oil (L. scoparium) and sandalwood (Santalum album) only inhibits Gram positive bacteria and does not have any effect on Gram-negative bacteria. In terms of antibacterial properties, Manuka oil outperformed eucalyptus oil, rosmarinus oil, lavandula oil, and tea tree oil (Raut and Karuppayil, 2014). Basil oil has antibacterial properties against Aeromonas, Hydrophila, and Pseudomonas fluorescens. Also, clove, thyme, lemon grass, bay, and oregano oils inhibit the growth of Escherichia coli and Staphylococcus aureus at MIC less than 1% and 0.05%, respectively. Eucalyptus oil with MIC of 1% also inhibits the growth of S. aureus (Edris, 2007). EOs mode of action is ascribed to their lipophilicity, which efficiently inhibits microorganism development by destabilizing cell membranes, leading to changes in electron flow, driving force of protons and facilitated diffusion, and agglomeration of cell contents (Fig. 3.2). Inhibition of various bacterial enzymes and denaturation of cellular lipids and proteins are some other pathways that leads to cell death (Raut and Karuppayil, 2014).

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FIG. 3.2 Mechanism of action of EOs on bacteria.

3.4.3 Antifungal EOs have been shown to be effective against a wide range of plant as well as human pathogen, including yeasts. EOs are abundant in phenylpropanoids notably eugenol and the monocyclic sesquiterpene alcohols such α-bisabolol which are responsible for the inhibition of dermatophytes and spores. The EOs obtained from the Melaleuca ericifolia (M. ericifolia), Melaleuca styphelioides (M. styphelioides), Melaleuca leucadendron (M. leucadendron), and Melaleuca armillaris (Megalaima armillaris) shows antifungal activity against Aspergillus niger. In general, orange, lemon grass and grapefruit oil effectively inhibits the growth of Aspergillus niger as well as shows fungicidal effect against A. flavus, Penicillium verrucosum, and P. chrysogenum. Other plants like M. piperita, black mustard (Brassica nigra), Angelica archangelica, Cymbopogon nardus, Skimmia laureola, Artemisia sieberi, and Cuminum cyminum have been tested positive for their antifungal activity (Raut and Karuppayil, 2014). Terpenoids-rich EOs have been proven to be extremely efficient against drug-sensitive and drug-resistant pathogenic yeasts, particularly against, Candida albicans (C. albicans). The oils derived from Syzygium aromaticum (clove) and Rosmarinus officinalis displayed enhanced antifungal activity against C. albicans. In addition, cinnamon, ginger grass, Japanese mint and lemon grass with MIC of 0.01%–0.15% inhibits the growth of C. albicans. Disruption within the cell cycle, inhibition of the membrane ergosterol and signaling pathways and the

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3. Importance of essential oils and current trends in use of essential oils

FIG. 3.3 Antifungal activity mechanistic pathways of EOs.

permeabilization of mitochondrial membrane leads to apoptosis that ultimately leads to cell death are some of the key mechanisms by which EOs illustrate the antifungal effects (Fig. 3.3) (Raut and Karuppayil, 2014a).

3.4.4 Anticancer EOs assist in the treatment of chemotherapy by decreasing the proliferation of various malignant cells such as leukemia, breast cancer, ovarian cancer, liver cancer, glioma, and others. Various EOs, such as thai lime, grape fruit, citronella grass, palmarosa, beetle leaf, and khus, are found to inhibit the growth of murine leukemia and human mouth epidermal carcinoma cells. Also, cardamom and eucalyptus oil induce apoptosis in human leukemia cells (Raut and Karuppayil, 2014). The EOs extracted from the Foeniculum vulgare, Matricaria chamomilla, Glycine max (soyabean oil), Myristica fragrans, Olea europaea (olive oil), and Tetraclinis articulate (conifer oil) effectively inhibits the proliferation of liver, glioma, colon, human neuroblastoma, colorectal, and breast cancer cell lines, respectively. M. fragrans (nutmeg oil) has been shown to have substantial hepatoprotective properties, which may be attributed to its key component, myristicin. The anticancer effects of Allium sativum (garlic) EOs are widely recognized (Raut and Karuppayil, 2014a). Garlic’s chemopreventive effect is limited to its capacity to inhibit drug detoxification enzymes. Cancer proliferation in rats is also inhibited by Nigella sativa and Melissa officinalis. EOs have the ability to act as antioxidants and to interfere with human cell mitochondrial activities. As a result, EOs reduce metabolic processes say enhanced cellular metabolism, mitochondrial overproduction, and persistent oxidative stress that are associated with the formation of malignant tumors. Terpenoids and polyphenol components in plant oils can induce apoptosis or cause necrosis, consequently inhibiting tumor cell growth.

3.4.5 Antiinflammatory Inflammation is a natural defensive reaction that is triggered by tissue injury or infection and serves to battle intruders in the body (microorganisms and nonself-cells) as well as to eliminate dead or damaged host cells. The potential of EOs to scavenge free radicals is accountable for its antiinflammatory effects (Perez et al., 2011). For instance, chamomile

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67

essential is utilized to alleviate the inflammation related to eczema, dermatitis. In addition, various EOs extracted from Ocimum sanctum, Baphia nitida, L. angustifolia, Eucalyptus sp., Citrus aurantium, T. vulgaris, Cananga odorata, Aloe barbadensis, Illicium verum, Lavandula officinalis, and Juniperus communis shows strong lipoxygenase inhibitory effects (Raut and Karuppayil, 2014a). Some other oils such as clove, rosemary, myrrh, lavender, eucalyptus, pine, and millefolia have been used to reduce inflammation. The presence of cinnamaldehyde in leaves of Cinnamomum osmophloeum suppress the lipopolysaccharide induced secretion of IL-1β and TNF-α. On the other hand, Artemisia fukudo not only inhibits the IL-1β and TNF-α but also slow down the release of IL-6 owing to the presence of camphor, caryophyllene, α-thujone and β-thujone. Inhibition of COX-2 enzyme and pro-inflammatory cytokines are some other pathways responsible for the antiinflammatory activities of EOs (Miguel, 2010).

3.4.6 Antiviral The presence of phenylpropanoids, monoterpenoids, and sesquiterpenoids in EOs is accountable for inhibition of virus replication. Administration of Artemisia arborescens found to inhibit the cell-to-cell virus diffusion of human Herpes Simplex Virus 1 and 2 (HSV-1 and HSV-2) with IC50 2.4 and 4.1 μg/mL, respectively (Adorjan and Buchbauer, 2010). Also, in vitro studies of EOs such as anise, thyme, ginger, chamomile, and sandalwood on RC-37 cells effectively reduces the replication of HSV-2 at IC50 0.016%, 0.007%, 0.004%. 0.003%, and 0.0015%, respectively. The mediated pathway is the disruption of HSV envelope which prevents the virus to enter into the host cells. On the other hand, manuka, pine, santolina, and tea tree oils are efficient against the HSV-1. Citral one of the components of EOs were reported to inhibit the yellow fever virus. EOs also inhibit the Cytomegalovirus (CMV) at early stage and thus inactivates the replication of gene expression (Raut and Karuppayil, 2014a). Components such as eugenol, carvacrol, β-santalol, and germacrene exhibits antiinfluenza activities (Ma and Yao, 2020). EOs extracted from Cymbopogon nardus inhibits HIV-1 reverse transcriptase enzyme at the 1.2 mg/mL concentration whereas oils obtained from Thymus vulgaris, Cymbopogon citratus, and Rosamarinus officinalis inhibits HIV with IC50 values in between 0.05 and 0.83 μg/mL. The components such as 1,8-cineole and isothymol derived from the EOs has been suggested to fight the recently discovered COVID-19.

3.4.7 Antidiabetic Diabetes is a metabolic disorder when pancreas in no longer produces insulin resulting in high glucose level in bloodstream. Various EOs have been studied for its antidiabetic properties but only few have been reported for its efficacy. Rosemary oil and oil obtained from Satureja khuzestanica found to be effective in hyperglycemic rabbits and regulates the blood sugar level in diabetic rats, respectively (Raut and Karuppayil, 2014a). Also, EOs namely, fennel, oregano, cumin, myrtle, and cinnamon when used in combination exhibits antidiabetic potential. Other studies suggested that EOs of Syzygium aromaticum and Cuminum cyminum has a potential to inhibit the enzyme α-amylase (an enzyme responsible for the breakdown of starch into sugars causing diabetes) at IC50 74.53 and 80.01 μg/mL, respectively (Fig. 3.4) (Raut and Karuppayil, 2014; Tahir et al., 2016).

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3. Importance of essential oils and current trends in use of essential oils

FIG. 3.4 Mechanism involved in antidiabetic potential of EOs.

3.4.8 Antiprotozoal EOs have been used traditionally to deal with the common health protozoal diseases namely malaria, giardiasis, amoebiasis, leishmaniasis, trichomoniasis, and chagas disease caused by Plasmodium species, Giardia lamblia, Entamoeba histolytica, Leishmania species, Trichomonas vaginalis, and Trypanosoma cruzi, respectively (Raut and Karuppayil, 2014a). EOs that are rich in eugenol (Ocimum gratissimum) and β-caryophyllene (C. reticulata and C. multijuga) found to be effective against leishmaniasis. Also, EOs of Artemisia herba, Artemisia abrotanum, Chenopodium ambrosioides, Pinus caribara, Piper aduncum, Piper auritum, Cymbopogon, and Croton cajucara were screened for their antileishmanial efficacy. Lemon grass exhibits the antitrypanosomal activity against Trypanosoma cruzi with IC50 of 126.5 and 15.5 μg/mL against the free cells of epimastigote and trypomastigote, respectively. Likewise, clove oil with IC50 value of 99.5 μg/mL for epimastigote and 57.5 μg/mL for trypomastigotes shows trypanocidal activity (Monzote and Alarco´n, 2012). The EOs obtained from the Ocimum basilicum and Achillea millefolium are also determined for its trypanocidal activity and Strychnos spinosa is used to treat Trypanosoma brucei brucei. Nerolidol-rich EOs such as Lippia multiflora and Virola surinamensis exhibit antiplasmodial properties. The EOs derived by Cameroonian plants such as Xylopia aethiopica, Antidesma laciniatum, Pachypodanthium confine, Hexalobus crispiflorus, and Xylopia phloiodora were studied for their antiplasmodial activity. Also, C. planchonii EOs extracted from the leaves is rich in β-caryophyllene and α-farnesene is responsible inactivates the P. falciparum at IC50 of 22–35 μg/mL (Monzote and Alarco´n, 2012). Terpenoids such as carvacrol, thymol and linalool present in Allium sativum and T. vulgaris exhibits antiamoebic activity. Other species Thymbra capitata, O. basilicum, Origanum virens, and Lippia graveolens suppress the G. lamblia.

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3.4.9 Anxiolytic potential Anxiety is the body’s natural response to stress, characterized by symptoms such as fear, restlessness, shortness of breath, palpitations, perspiration, and so on. To ease these psychological and physiological actions, tranquilizers, antipsychotics, beta blockers, and benzodiazepines are employed. Benzodiazepines have strong anxiolytic potential but is not generally recommended due to its limitations such as addiction, sedation, and drug tolerance. Consequently, scientists have observed that EOs can be an alternative therapy to calm the nerves. Various EOs can be used as anxiolytic agents such as lavender (L. angustifolia), orange (Citrus sinensis), sandalwood (Santalum album), clarry sage (Salvia sclarea), rose (Rosa damascene), and bergamot (Citrus bergamia). C. bergamia is used to treat the anxiety and mood swings among cancer patients. Also, oil extracted from the flowers of Citrus aurantium (Neroli oil) exhibits anxiolytic potential (Ayaz et al., 2017).

3.4.10 Anticholinesterase potential Alzheimer’s disease (AD) is a neurological disorder that causes brains cells to shrink and eventually die. The disease is attributed to the oxidative stress, accumulation of amyloid plaques, production of neurofibrillary tangles, memory loss, and cognitive disorder. Inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes (which destroys the acetylcholine (ACh)) results in the improved memory and cognitive function. Recently discovered anti-Alzheimer drugs, namely, rivastigmine, tacrine, and donepezil, block the AChE/BChE and consequently inhibits the degradation of fundamental neurotransmitter ACh. The increase in concentration of ACh in brain results in the relief of AD symptoms. Galantamine, a natural product originally isolated from the snowdrop, belongs to the Amaryllidaceae family is known to exhibit anticholinesterase activity. EOs isolated derived from inflorescence of Polygonum hydropiper successfully inhibited the AChE and BChE having IC50 of 220 and 225 μg/mL, respectively. Likewise, EOs obtained from leaves of P. hydropiper inhibits the AChE and BChE at IC50 120 and 130 μg/mL, respectively. Also, EOs from Rumex hastatus, Salvia leriifolia, Narcissus poeticus, and Marlierea racemosa were also evaluated for anticholinesterase activity. Cistus species were also reported to exhibit neuroprotective and AD modifying ability (Ayaz et al., 2017). Table 3.4 represents the active constituents and different biological properties of different essential oils.

3.5 Economic importance While large-scale industrial production is quickly taking over global agriculture, most essential oil production is still controlled by small farmer production, which contributes considerably to the incomes and livelihoods of relatively underprivileged rural populations in developing countries. Although “naturals”—plant extracts and essential oils—are minor products in comparison to the major commodities and staples that dominate global agricultural production, they have become an integral part of daily life, used in a wide range of consumer products, and their usage is expected to increase year by year. The flavor and fragrance business is projected to employ around 0.01% (250,000 ha) of total world agricultural land to

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TABLE 3.4 Medicinal uses of various EOs (Djilani and Dicko, 2012; Irshad et al., 2019). Essential oil

Species

Active compound

Properties

Lemon oil

Citrus limonum

Limonene

Immunity booster, metabolism regulator, antimicrobial, antiviral, digestive carminative, and purgative

Tea tree oil

Melaleuca alternifolia

Terpinene-1-ol-4

Antimicrobial, antiviral, antiasthenic, neurotonic, radioprotective, lymphatic, and antispasmodic

Lavender oil

Lavandula officinalis

Linalol and linalyle acetate

Antispasmodic, antiinflammatory, sedative, analgesic, and antimicrobial

Peppermint oil

Mentha piperita

Menthol and menthone

Anesthetic, analgesic, stimulant, antimicrobial, antiinflammatory, mucolytic

Eucalyptus oil

Eucalyptus globulus

1,8-cineole

Mucoactive agents, anticatarrhal, antimicrobial

Sweet orange oil

Citrus sinensis

Limonene

Antiseptic, flavoring agent, carminative, stomachic tonic

Cinnamon oil

Cinnamomum cassia

Cinnamaldehyde

Antiparasitic, anticoagulant, insecticide, antimicrobial, uterine syrup

Clove oil

Syzygium aromaticus

Eugenol and eugenyl acetate

Antimicrobial, stomachic, an aesthetic, carminative. Stimulant and hypertensive

Garlic oil

Allium sativum

Diallylle disulfide

Hypertensive, hypoglycemic, antimicrobial, antiparasitic, antioxidant, larvicidal, and insecticidal

Dill oil

Anethum graveolens

Carvone

Maintains fluidity of bronchial secretions

Cedar oil

Cedrus libani

Limonene

Antimoth, larvicidal, lymphatonic, antifungal, astringent, diuretics, and antiseptics

Nutmeg oil

Myristica fragrans

Sabinene, 4-terpineol, and myristicin

Pesticidal, hepatoprotective, carminative, analgesic. Antiseptic and antiparasitic

Anise oil

Pimpinella anisum

Anethole

Emmenagogue, cardiac stimulant, carminative, and diuretic

Chamomille oil

Matricaria chamomilla

Bisabolol and chamazulene

Decongestive, antispasmodic, antiallergic, antiinflammatory, and antipruritic

Peppermint oil

Menthepiperita

Menthol, menthone

Antioxidant, antimicrobial, antiseptic, flavor, antiinflammatory, and antiviral

Rose oil

Rosa species

Farnesol

Antibacterial, antiinflammatory, and antiseptic

Caraway oil

Carum carvi

Carvone, carvacrol

Aromatherapy, carminative, and stimulant

Thyme oil

Thymus vulgaris

Thymol, linalool, and carvacrol

Antimicrobial, food preservative, flavor, irritant, anesthetic, and pesticidal

Oregano

Origanum vulgare

Γ-terpinene, and δ-terpineol

Food preservation, treat the disorders of respiratory tract and nervous system

3.5 Economic importance

TABLE 3.4

71

Medicinal uses of various EOs (Djilani and Dicko, 2012; Irshad et al., 2019)—cont’d

Essential oil

Species

Active compound

Properties

Fennel

Foeniculum vulgare

Ketone, limonene

Antidiabetic and stimulant aromatic

Cumin

Cuminum cyminum

α-pinene and β-pinene

Carminative and stimulant

Garlic oil

A. sativum

Allicin and propyl disulfide

Carminative, disinfectant, and stimulant

Basil oil

Ocimum basilicum

Eugenol

Antidiabetic, bactericidal, antiviral, and anticancer

Rosemary

Rosmarius officinalis

Bornyl acetate and borneol

Relieves from constipation, indigestion, and colitis, rheumatic pain, controls blood pressure and improves cognitive function

Lemon grass oil

Cymbopogon citratus

Neral and citral

Cleanser, antiviral, antimicrobial, antiviral, insect repellent

Neroli oil

Citrus aurantinum var. amara

Linalool

Antianxiolytic, useful for premenstrual syndrome, antispasmodic, pregnancy, and delivery aid

produce 200–250 different plants for the manufacture of these naturals. These crops are essential not just for the socioeconomic well-being of the people that grow them, but they are also crucial for the environment (Devi et al., 2015 and references therein). Many of the crops are short- or long-term perennials, providing stable environments; cultivation of many of the crops is based on long established traditional varieties in balance with the surrounding flora; wild crafted crops support the maintenance of natural vegetation and its complex of flora and fauna. They are commonly utilized in the cosmetics, perfumery, and aromatherapy industries. The latter is meant to be a therapeutic approach that includes massage, inhalations, or baths with these volatile oils (Devi et al., 2015 and references therein). The use of essential oils (EOs) is an area of great interest that contributes to the development of the country. The daily needs have been occupied by EOs from flavor to fragrance, food to pharmaceutics, personal to beauty care products. More than 300 kinds of EOs have been used commercially in food, cosmetic, agronomics, sanitary, and pharmaceutical industries. Countries such as USA, Germany, Japan, UK dominate the world’s EOs market. India is the world’s largest producer of Japanese mint oil, and Indian basil oil all and hence is a global exporter of both EOs (Devi et al., 2015 and references therein). Rose and tuberose are also grown in higher proportions in Uttar Pradesh and Andhra Pradesh (Hyderabad). The southern states such as Tamil Nadu, Kerala, and Karnataka are recognized for producing the jasmine oil. To avoid undesirable odors, EOs are frequently utilized in the perfume, textile, paint, and plastic industries. EOs have an important role in dermatology such as to treat the rashes, boils, urticaria, eczema, and psoriasis that facilitate the growth of the skin industry. By 2024, India’s EOs market would be worth up to $790 million USD. Because India is a vast country, it employed large-scale agronomic systems to cultivate the EOs plants such as

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spices, lemon, and mint (Devi et al., 2015 and references therein). Following are the some top contenders of essentials oils which have a huge market potentiality as well as major economic concern: Rose sector: There are just a few rose farms in Turkey, with the most notable being near Isparta. There are a large number of family-based smallholders with 1–2 acre holdings who cultivate rice. Around 10,000 households are said to be participating in the project. Rose oil may be extracted from up to 3500 kg of fresh rose blossoms, yielding up to 1 kg of oil. Good cultivation techniques can yield up to 3500 kg/acre of fresh roses, however in other regions and with bad cultivation practices, flower yields can be much lower than this. Sebat-United, Gulbirlik, Robertet, IFF-Ercetin, and Biolandes are some of the biggest producers of rose oil. Production of roses has been declining over the last few years and this decline is continuing. Because of unfavorable weather conditions, production fell down in 2015. Flowers are being stunted by late frosts and heavy spring rains (March/April/May), which encourages growth instead of bloom production. In a good season, flower output capacity is expected to be between 7000 and 8000 tons. Flower cultivation in this area produces between 1500 and 1600 kg per year of rose oil, while rose concrete output is in the 7000–8000 kg per annum range (ITC, 2014). Oregano oil: In terms of essential oils, this is the second-largest essential oil after rose. Market share is held by Turkey, which supplies 70% of the world’s oregano oil. About 15–20 tons per annum are produced on a yearly basis. You may get the essential oil from a wide range of plants: from thymus to origanum. This oil is mostly obtained from wild-harvested plants. In addition to the Aegean and Mediterranean, the Marmara region also has some output. 5%–8% of the oil comes from Origanum dubium. The best time to gather the oil is when the flower buds develop (ITC, 2014). Laurel oil (Bay; Laurus nobilis): Around 80% of the world’s laurel oil comes from Turkey, which leads the industry. Only wild herbs are utilized to make this product. Naturally, the plants may be found in the Aegean, Mediterranean, and Black Sea beaches, but the frequent rainfall in the Black Sea region makes it difficult to dry the leaves and produce a high-quality end product (ITC, 2014). Cumin seed oil (Cuminum cyminum): Cumin seed oil is produced at a rate of around 3.5 tons per year. The cultivation of the plant has two major purposes: seed trade and essential oil distillation. Most of the cultivation takes place in the Anatolia, Aegean, and southeast regions surrounding Konya, Ankara Eskisehir Afyon Sanliurfa, and Denizli regions (ITC, 2014). Sage oil (Salvia triloba): Salvia triloba is used to make sage oil in Turkey. About 1.5–2 tons of sage oil are produced annually. 1,8-cineole is the major component of the oil, which distinguishes it from S. officinalis cultivars that are high in thujone. Thujone is known to be poisonous, which is why low-thujone sage leaves and oil are becoming more popular on the market. Wild and farmed sage are both used for harvesting (ITC, 2014). Rosemary oil (R. officinalis): Approximately 500–750 kg of rosemary oil are produced annually. Wild plants in the eastern Mediterranean region are used entirely for its production. As well as being used in the herb/spice trade, it is also used in distillation (ITC, 2014). Aniseed oil (Pimpinella anisum): About 200–300 kg of aniseed oil are produced each year. In the Aegean Sea, where the temperature is hot and humid, the crop is grown, and it is harvested in August. Turkish raki liquor is flavored with aniseed (ITC, 2014).

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Fennel seed oil (F. vulgare): About 250–350 kg of fennel seed oil are produced annually. The Denizli region is the primary agricultural area (ITC, 2014). Myrtle oil (Myrtus communis): About 200–300 kg of this product are produced annually. Wild plants found near the coasts are the only ones that may be harvested. As well as being used for distillation, the leaf is sold to the herb/spice trade (ITC, 2014). Coriander seed oil (C. sativum): There are around 200–250 kg of oil produced each year. As a result, it is farmed mostly in Anatolia and the Aegean Sea. Since the country’s seed output is quite limited, most of the local need is satisfied by imports (ITC, 2014). Ylang Ylang Oil: All ylang oil comes from Comoros, Mayotte & Madagascar. Following Comoros is Madagascar as the world’s largest producer. Mayotte’s production has all but ceased, and it’s hard to believe (due to uncompetitively high labor costs). Due to the fact that ylang ylang is combined with niaouli and clove oils in the Harmonized Codes, it is impossible to acquire comprehensive trade figures for the European Union market for this essential oil. Since the islands of Comoros and Mayotte do not generate large quantities of these other oils, they can all be considered ylang oil imported into the EU. It is impossible to separate the ylang oil from the other oils produced in Madagascar, such as niaouli and clove. Only cananga oil and ylang oil are mixed in US trade statistics, thus the oils can be separated based on where they were produced. Long-term declines in output of ylang ylang oil have occurred in Comoros and Mayotte during the past 30 years. Over the years 2005–2010, Comoros’s output dropped from approximately 90 tons a year into a 30-to-40-ton range. Over the previous 5 years, Mayotte’s production has dropped from about 20 tons to less than 1 ton. Madagascar’s current production levels are unknown, but are expected to be in the vicinity of 15 tons. Therefore, import prices are calculated by taking the average price of all grades of ylang oil. Prices have progressively climbed in recent years since their lows (varying from 60 to 120 euros per kg during the past decade). Both flowers and oil prices at the Comoros distillery have climbed in recent decades as a result of the market’s price hikes. Over the same period prices for oil at the distillery have risen from KMF 375/degree/kg to KMF 1000/degree/kg in 2012, to current prices of KMF 1450/degree/kg (Ylang Ylang Oil—a review of production from Comoros). Geranium oil: Many perfumes and home products utilize geranium oil as an essential floral component. It’s a key ingredient in soap, and it’s also utilized in herbal medicine, aromatherapy, and pharmacy. Clinical and scientific studies have shown that it has antibacterial qualities, as well as a positive impact on human health and psychological condition. Rhodinol is mostly composed of citronellol and geraniol ex geranium. Geranium oil may be produced at a rate of 60–70 kg per hectare with an average oil yield of 0.15%–0.2%. We get the oil via steam distillation of the leaves, which yields the oil. A few days after harvesting, the harvested material is often put out in the sun to dry off before distillation. Around 8000 households are believed to be involved in the manufacture of geranium oil, and if all those participating in the supply chain are included (middlemen, factory employees, etc.), together with their dependents, 30,000–35,000 individuals are expected to be involved in the trade. Other than essential oil, minor amounts of concrete and absolute are also produced. For every kilo of concrete produced from 500 kg of leaf material (0.2% yield). 0.6–0.7 kg of absolute are included in a kilogram of concrete. It is utilized in compositions when alcohol solubility is needed. In China, Yunnan Province is the main producer of the commodity. However, as farmers have acquired access to a larger choice of crops, geranium cultivation has spread

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to less developed areas of Yunnan. Binchuan, on the other hand, remains the most significant collecting center. In the past, there were two harvests a year, but now there is one every month (increasing to every 2 weeks at the height of the season between March and October). Before replanting, plants are typically preserved for 5 years, although in some places where plant losses are severe, replanting occurs after 3 years. Approximately 120,000 trees are planted each hectare (approx. 30 cm  30 cm). The entire planted area is expected to be approximately 1000 ha. Geranium oil has a yield of 0.2%–0.25%, with an average production of 75–105 kg/ha. According to estimates, between 5000 and 7000 households are involved in the manufacturing of geranium oil, with the total number of individuals participating in the entire supply chain and their dependents reaching 25,000–30,000 (Geranium oil). Sandalwood oil: Woody notes and a natural fixative distinguish sandalwood oil, which is extracted from the heart wood and roots of the sandalwood tree. Perfumers admire sandalwood oil for its woody notes, which provide depth and richness to scents. Beyond being a source of oil, the wood is highly prized for its use in carving and furniture building. Wood and essential oil demand is increasing, prices are rising exponentially, a slow-growing tree takes 30–60 years to produce a harvest of roots or heartwood, and there are no sustainable harvesting options, all of which set the stage for uncontrolled and illegal harvesting and destruction of the natural resource. 40 years ago, sandalwood oil cost less than $100/kg; today, it costs more than $2000/kg, demonstrating the scarcity of the supply (Sandalwood oils). Patchouli (Pogostemon cablin) oil: Among the most important ingredients in fragrances is patchouli essential oil. Many exquisite fragrances and various items, from toiletries to soap to detergent to candle and incense use this compound extensively. Pharmacists often employ this component in medicines against acne, dandruff, and other skin diseases because of its potent antimicrobial properties. Additionally, it’s utilized as a repellant for flies. Patchouli oil is mostly produced in Indonesia, which accounts for about 90% of global trade. There is a lot of production going on in China and India but all of it is going to their local markets. Annual production is about 1200 tons, valued in US$70–100 million. Oil from patchouli trees is mostly produced by the steam distillation of shade-dried leaves. The plant is cultivated as a short-term perennial. Harvesting begins 6–7 months after planting and continues every 3–4 months until the plant is 2 years old. Patchouli may be intercropped with other plants. Patchouli is still mostly distilled by local farmers using basic distillation equipment. In most cases, distillation takes 8 h or more. There are many people involved in the supply chain for patchouli oil, including farmers, farmer-distillers, collectors and agents. Indonesian farmers typically possess 0.25–1 ha of land and produce 25–100 kg of patchouli oil per year. Around 4–5 tons/ha of dry leaf yields are expected in most cases. A total of 12,000 farmer households cultivate patchouli. Patchouli is the primary source of income for about 50,000 individuals. Another 2000 people are employed in distillation (425 units, each employing 5 workers) and 300 in the collecting trade (The socio-economic importance of the essential oil production sector). Cornmint (Mentha arvensis) oil: Food, pharmaceutical, perfumery, and flavoring businesses use cornmint oil as a major ingredient in their products. In items such as soaps, detergents, cosmetic and perfumes, toothpaste and industrial scents, it is widely utilized in fragrances. Food goods such as confectionery, liquors, and chewing gums employ it as a flavoring ingredient. Also used in cough syrups, lozenges, herbal teas, lotions, ointments, and nasal sprays for colds and infections, menthol or oil is a significant component. Cosmetics

3.6 Current trends

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utilize both oil and menthol as active ingredients because of their cooling and antibacterial qualities. Since 1977, India has risen from 20% to over 90% of world crude oil output. Approximately 32,000 tons of cornmint oil were produced worldwide in 2009, with India contributing for 30,000 tons and China accounting for 2000 tons. A total of 34,500 tons were produced in India in 2012; this number will likely reach 50,000 tons in 2013. More than 162,000 ha of mint are farmed in Uttar Pradesh, Haryana, and Punjab in India, with the majority of the land being utilized for cornmint (90%). On average, rural farmers control 90% of cornmint output. After rice wheat and rice-potato in India, mint is a seasonal third crop. Most farmers plant their crops between January and March, thus nurseries must be maintained throughout the year. A late rainfall that prevents rice planting will be compensated by late mint harvesting. Mint is distilled by both farmers and nonfarmers. A 2010 survey from India’s Central Institute of Medicinal and Aromatic Plants found that there are 12,750,000 individuals working to produce the oil. Approximately 24,000 tons were produced during that period. There are an estimated 15,000,000 individuals involved in the present production of about 45,000 tons. Producing cornmint oil is a major source of income for many rural households in northern India. Farming communities in rural areas have benefited from the development of cornmint oil production by investing in their children’s education and family health care costs (The socio-economic importance of the essential oil production sector).

3.6 Current trends 3.6.1 Food preservation Essential oils exhibit antimicrobial and antibacterial activities that make them suitable for food preservation purposes. These are used as antifungal agents for food safety items. Also, they exhibit their properties as antimicrobial food packaging materials such as edible thin films and nanoemulsions. Soft drinks, carbonated drinks and various seafood items also contain these oils as a flavoring and preserving agents (Bhavaniramya et al., 2019). Various essential oils like lemon oil, tea tree oil, thyme oil, oregano oil, cinnamon oil, peppermint oil, lavender oil, and eucalyptus oils are used for various purposes in the food industry. For example, lemon essential oils contain oxygenated terpenes that have antifungal properties and exhibit the growth of fungi like C. tropicalis, C. albicans, and C. glabrata (Bhavaniramya et al., 2019; Ooi et al., 2006). Essential oils of oregano, thyme and cinnamon show antimicrobial activities against bacterial pathogens like P. fluorescens, E. coli, etc. Essential oils contain monoterpenes, sesquiterpenes and various oxygenated derivatives that have pathogenic activity against various microorganisms giving various antioxidant and antimicrobial properties (Mith et al., 2014).

3.6.2 Medicinal uses Essential oils present in various plants also act as biocontrol agents. Biocontrol products are mainly micro-organisms, micro-organisms, natural substances from plant, animal, algae, and semichemical products. Essential oils are potential bio-sourced products that can be used against various agents and are safer than the synthetic pesticides and are environment

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3. Importance of essential oils and current trends in use of essential oils

FIG. 3.5 Major monoterpenes present in essential oils (Bhavaniramya et al., 2019).

friendly (Raveau et al., 2020). Various biological activities of these oils are due to their bioactive phytoconstituents that mainly consists of terpene hydrocarbons (consisting of 80% monoterpenes) and oxygenated compounds of alcohols, aldehydes, esters and phenols (Fig. 3.5) (Asbahani et al., 2015). 3.6.2.1 Antibacterial properties Essential oils have antibacterial properties that show various responses to pathogens. Various studies are conducted by the researchers over past years to check the bactericidal property of essential oils and making them a potential biocontrol agents. Example essential oils from basil induce inhibition to various bacterial pathogens like Pseudomonas tolaasii, Xanthomonas citri, Rhodococcus fascians, etc. (Raveau et al., 2020). 3.6.2.2 Antifungal properties Fungi are main concerning pathogens as they damage nearly 30% of the crop starting from harvesting, postharvest to storage. Some of the species like Aspergillus and Fusarium also produce mycotoxins that are carcinogenic. There efficient removal and defense is an important task. Essential oils display various antifungal activities that inhibit the growth of these species. Example clove essential oils displayed antifungal activity against C. albicans (Rattanachaikunsopon and Phumkhachorn, 2010). Most common phytopathogenic fungi are Alternaria, Penicillium, Fusarium, Rhizoctonia, and Botrytis ( Jain et al., 2019; Raveau et al., 2020). Table 3.5 represents various essential oils used against various fungal pathogen.

3.7 Future perspective EOs are the phytocomplexes that have bioactive ingredients. These represent the aromatic and volatile components of plants. Traditionally they have been used in food industries, medicine, and antiseptics only. Now they are finding their place in aromatherapy which helps in treatment of various diseases. Their market value is increasing day by day, majorly credited to food preservatives and cosmetic industry, then to aromatherapy and household products and at last to pharmaceuticals. In food industry also they have found their value as food preserving agents, coloring, flavoring, aromatic agents and also are used to design biofilms and nano-

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3.8 Conclusion

TABLE 3.5

EOs as biocontrol agents for various pathogens.

Pathogen Bacteria

Fungi

Disease caused

Essential oil used

References

Pseudomonas spp.

Ring rot disease, leafy gall disease, bacterial spots, blights

Ocimum ciliatum, Citrus reticulata, Achillea biebersteinii

Behiry et al. (2020), Carezzano et al. (2017), Kotan et al. (2014), and Moghaddam et al. (2014)

Xanthomonas spp.

Bacterial spots and blights, fire blight, ring rot

Achillea biebersteinii, Citrus aurantinum L., Thymus fallax

Agrobacterium tumefaciens

Bacterial spots and blights

Citrus aurantimum L.

Alternaria

Leaf spot, alternariose

Carum carvi L., Carum opticum L., Thymus zygis, Carus nobilis, Asarum heterotropoides

Asperigillus spp.

Ochratoxin producer, rot and mold, aspergillosis

Citrus limon L., Curcuma longa, Eucalyptus spp., Thymus capitatus, Ferula galbaniflua

Botrytis cinerea

Grey mold

Thymus zygis

Fusarium spp.

Fusarium wilt (vascular disease)

Eucalyptus erythrocorys, Genista quadriflora

Penicillium digitatum

Green mold

C. carvi L., Carum opticum L.

Pencillium italium

Blue mold

Foeniculum vulgare, Thymys spp.

Rhizoctonia spp.

Damping off, root, and stem rot

Ginger officinale, Thymus vulgaris

Boubaker et al. (2016), Kacem et al. (2016), Ben Ghnaya et al. (2013), and Hu et al. (2017) Abdolahi et al. (2010), Carezzano et al. (2017), Dan et al. (2010), Dimic et al. (2015), Kotan et al. (2014), Sapper et al. (2018), and Xu et al. (2014)

emulsions. Future of essential oils will see a boon in cosmetic industry and in curing skin diseases. Pharmaceutical companies are designing medicines that are natural plant based and are environment and human friendly. Furthermore, the enhanced interest of scientists and researchers around the globe toward the applications of natural, eco-friendly, low toxic, and more economic drugs indicate huge prospective of EOs as substantial substitutes in a different industry. Moreover, given the availability of more efficient and emergent techniques, like encapsulation, microtechnology, and nanotechnology for improved drug delivery, pesticide delivery and protection against volatility, oxidation, among others, additional industrial applications and utilizations of EOs are to be forecasted in the coming future.

3.8 Conclusion EOs have widespread applications in food, cosmetics, perfume, incense, and pharmaceutical industries. Owing to their attractive fragrance, essential oils are also used largely in the

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3. Importance of essential oils and current trends in use of essential oils

perfume and incense industries. Different essential oils and their individual bioactive phytoconstituents are widely used as natural antioxidant, antimicrobial agents, insect repellent and preservatives in order to decrease the impact of different oxidative deterioration, microbes, pathogens, and insects in food products. Essential oils are also generally used topically to relieve the pain. Further, essential oils are also extensively used for the cure of various ailments and diseases such as anxiety, depression, wound healing, cancer, inflammation, oxidative stress, fungal infection, microbial infection, and parasitic infection. Presently, the better understanding and knowledge of EOs chemistry and their modes of action has led to the advancement of diverse applications of EOs, particularly in human health. These developments widen the therapeutic applications of EOs in the treatment and management of diverse array of ailments. Parenting to all these applications, the worldwide consumption and demand of essential oils increases rapidly. Therefore, the essential oil market is emerging at faster rate and getting more significant day by day. However, in order to establish the optimum dose, real efficacy, safety and toxicology of different essential oils, more scientific evidence and clinical studies are mandatory.

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A study of the variability of rosemary and sage and their volatile oils on the British market: their antioxidative properties. Flavour Fragr. J. 7, 81–87. https://doi.org/10.1002/FFJ.2730070207. Tahir, H.U., Sarfraz, R.A., Ashraf, A., Adil, S., 2016. Chemical composition and antidiabetic activity of essential oils obtained from two spices (Syzygium aromaticum and Cuminum cyminum). Int. J. Food Prop. 19 (10), 2156–2164. https://doi.org/10.1080/10942912.2015.1110166.

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C H A P T E R

4 Lavender essential oil: Nutritional, compositional, and therapeutic insights Farhan Saeeda, Muhammad Afzaalb, Muhammad Ahtisham Razaa, Amara Rasheeda, Muzzamal Hussaina, Gulzar Ahmad Nayikc, and Mohammad Javed Ansarid a

Department of Food Science, Government College University Faisalabad, Faisalabad, Pakistan Food Safety and Biotechnology Laboratory, Department of Food Science, Government College University Faisalabad, Faisalabad, Pakistan cDepartment of Food Science & Technology, Government Degree College Shopian, Srinagar, Jammu & Kashmir, India dDepartment of Botany, Hindu College Moradabad (Mahatma Jyotiba Phule Rohilkhand University Bareilly), Bareilly, India b

4.1 Introduction Lavender is an evergreen herbaceous plant that is also characterized as curative lavender. It is native to the Mediterranean Sea region and Europe, as well as Africa and Middle Eastern countries, as well as southwest Asia and southeast India. There are over 30 species, including many subspecies. It is a Western plant native to Bulgaria, France, Spain, and Italy, although it also planted in so many other areas (Prusinowska and S´migielski, 2014). Most lavender plants were raised and distilled in higher elevations in the Mediterranean Sea (600–1500 m). Its major constituents include Linalyl acetate, linalool, 1, 8-cineol B-ocimene, terpinene-4-ol, and camphor. Their comparative levels arise from species to species. Essential oils are utilized for psychological and physiological aspects of an individual’s sensitivity to volatile biostructures to relieve stress and speed up healing processes, including illness prevention and treatment. The terms “volatile oil,” and “essential oil,” are used to describe a liquid material found in specialized cells of plants and extracted using specific extraction processes. The majority of

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00009-8

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Copyright # 2023 Elsevier Inc. All rights reserved.

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essential oils are liquid; however, depending on the temperature of the environment in which they are stored, they can also be solid or semisolid (Samfira et al., 2015). Oil is the major isolate of the Lavender plant and is processed further for health and nutraceutical purposes. Lavender oil is widely used as an independent alternative medication as well as a constituent in a variety of cosmetic products and over-the-counter (OTC) complementary medicines. The extracts and essential oil of Lavandula angustifolia have been shown to have anticonvulsant, anxiolytic, antioxidant, anticholinesterase, antibacterial, and antifungal properties in the literature. Various compounds in the oil also have beneficial medicinal characteristics, including antimicrobial, antiinflammatory, and antioxidant capabilities. The genus “Lavandula” classifies the Lavandula genus into 37 species depending on leaf shape, corolla structure, calyx, and bract. In the fragrance and pharmaceuticals sector, the lavender oil extracted from three species (L. angustifolia, Lavandula hybrid, and Lavandula latifolia) (Dong et al., 2020). Mostly the oil is produced by glands embedded on the surface of the flowers and leaves indeed, products developed from the common garden herb Lavender have been utilized as a remedial agent for decades, with the essential oils isolated from these plants being widely employed as an antibiotic. In addition to its antibacterial characteristics, the oil is thought to have hypnotic, stomachic, antiinflammatory, and antidepressive properties (Cavanagh and Wilkinson, 2005). Oil is the most valuable constituent, isolated from L. angustifolia. Lavender essential oil (L. angustifolia) has a unique composition that depends on climatic conditions, genotype, reproduction, and morphological traits (Smigielski et al., 2018). In the current book chapter, we discussed the current status; production, extraction, and nutritional profile of lavender oil. Therapeutic potential and bioactivities are also limelighted in this chapter. Extraction is the crucial process of any sample for an analytical study. The majority of chemists take this as a second priority, but two-third attention of chemists should be on the extraction techniques. Essential oils are a mixture of molecules with a lower molecular weight (0.5 kDa) that store in plant glands, oil ducts, and resin ducts. Solvent extraction, hydrodistillation (HD), and steam distillation (SD) methods used in to extract oils. Commercially hydro-distillation is the most preferred method due to its high yield and low cost but now researchers are still working to explore the new techniques through which minimum production time and low cost can be utilized. However, advancements in hydrodistillation like Ohmic assisted hydrodistillation (OAHD), ultrasound-assisted hydrodistillation, and microwave-assisted hydrodistillation techniques are introduced through which maximum isolate can be obtained (Gavahian and Chu, 2018). During the extraction process, many factors can influence the quality of the isolate, i.e., extraction time, extraction temperature, pH of solvent, and total extraction cycles. The yield during extraction can be enhanced by increasing the time but more delay in time leads toward the oxidation of polyphenols. Lavender is one of the world’s top 15 most traded essential oil plants (Pakdemirli, 2020). Bulgaria and France are the largest producers of Lavender oil and export more than 70% all over the world.

4.2 Current status The Lavender plant is cultivated in many countries of the world. France, Bulgaria, United Kingdom, Russia, Spain, and China are the top producers. Lavender is also grown in Italy, Morocco, the former Yugoslav republics, Romania, Ukraine, Poland, Hungary, South Africa, Moldova, Turkey, and United States of America (Grebenicharski, 2016; Stanev et al., 2016). In industrial scale,

4.4 Extraction techniques

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Bulgaria, France, China, Russia, and a few other Eastern European states are most prominent exporters of Lavandula oil, whereas New Zealand is a newcomer toward the global market (Giray, 2018). France and Bulgaria are the biggest lavender oil producers and exporters worldwide. These two countries produce 75% of lavender globally. Bulgaria is the world’s largest lavender producer, has around 4500 ha of producing land and produced 200 tons of lavender essential oil in 2017. According to World lavender oil production by countries (2017), the production of lavender oil in Bulgaria is 52%, France 26%, China 12%, and 10% from other countries (Giray, 2018). In the Xinjiang Autonomous Province of China, collectivist units produce 1500ha of lavender. With a potential of over 40 tons, it has a lot of potentials, but China only sells about 10 tons to the worldwide market. India produces tens of thousands of tons of lavender, although it is often from other genera, and it is largely consumed domestically, with only a small amount exported. Ukraine is a large producer with production capacity of more than 1000ha, however due to adverse climatic conditions, it is currently believed to be around 1000ha, and lavender oil production recorded 10 and 15 tons in current years (Australia, 2017; Giray, 2018).

4.3 Biochemical profile Lavender oil is obtained from L. angustifolia is the most important product of essential oil market. Lavender oil not only contains essential oils it also contain phytosterols, minerals, valeric acid, anthocyanins, sugars, glycolic acid, coumaric acid, ursolic acid, coumarin, herniarin, and tannins which have both nutritional as well as therapeutic potential that promote the biochemical reactions and promote the health. Lavender oil contains more than 100 compounds, out of which 2 more prominent constituents are linalool and linalyl acetate. Further bioactive compounds comprise α-pinene, α-thujene, sabinene, camphene, myrcene, p-cymene, β-pinene, limonene, 1,8-cineole, (Z)and (E)-β-ocimene, camphor, 7-terpinene, terpinene-4-ol, lavandulol, β-caryophyllene, lavandulyl acetate, etc. (Tomi et al., 2018). The biochemical profile of different lavender species depends significantly on the geographical area of plant material. Biało
n et al. (2019) concluded in his study that linalool and linalyl acetate should be greater than 1% in oil for better antimicrobial activity. The high concentration of lavandulol and lavandulyl acetate imparts rosaceous and sharp floral aroma in the oil. The chemical composition of lavender oil was explored by gas chromatography-mass spectrometry (GC–MS) (Ali-Shtayeh et al., 2018). Lavender oil consists of Myrcene (2.05%), α-Phellandrene (0.14%), 3-δ-Carene (0.20%), α-Terpinene (0.15%), Cymene (0.20%), Limonene (0.12%), 1–8-Cineole (0.05%), Ζ-β-Ocimene (2.63%), 2–6-Dimethyl-3-5-7-octatriene-2-ol (0.08%), β-Ocimene (0.20%), Terpinolene (5.34%), p-Cymenene (0.10%), α-Terpinolene (0.04%), Caryophyllene oxide (1.11%) 1–3-8-p-Menthatriene (0.03%), p-Cymen-8-ol (0.53%), 4-Terpineol (0.21%), 4–5-Epoxy-1-isopropyl-4-methyl-1-cyclohexene (0.36%), Cravacrol methylether (5.36%), Thymol (0.26%), Carvacrol (65.27%), Para-menth-1-en-9-ol (1.73%), ε-Caryophyllene (6.21%), α-Humulene (0.20%), and Β-Bisabolene (7.43%) (Table 4.1).

4.4 Extraction techniques Lavender is most common raw material for the fragrance, cosmetic, and foodstuffs due to its unique composition of polyphenols and presence of bioactive ingredients that have a

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TABLE 4.1 Chemical profile of lavender oil. Chemical

Percentage

References

Linalool

20%–45%

Koriem (2021)

Terpinen-4-ol

1.2%–6.0%

Koriem (2021)

Lavandulol

0%–7.01%

Wells et al. (2018)

Linalyl acetate

25%–46%

Koriem (2021)

Borneol

0%–6.2%

Wells et al. (2018)

Camphor

0%–1.7%

Wells et al. (2018)

Lavandulyl acetate

1.0%

Koriem (2021)

γ-Cadinene

1.2%

Wells et al. (2018)

α-Cadinol

1.2%

Wells et al. (2018)

3-Octanone

2.5%

Koriem (2021)

Geranyl acetate

1.8%

Wells et al. (2018)

Camphor

1.2%

Koriem (2021)

Limonene

1.2%

Koriem (2021)

Cryptone

2.7%

Wells et al. (2018)

α-Terpineol

2.0%

Koriem (2021)

1,8-Cineole

2.5%

Koriem (2021)

β-Ocimene

0.4–21.2

Wells et al. (2018)

Camphene

0.4%–0.6%

Wells et al. (2018)

γ-4-Carene

0.2%

Wells et al. (2018)

Hexyl butanoate

0.2%

Wells et al. (2018)

therapeutic effect on the human body. It is extracted through traditional and commercial methods like steam distillation, hydrodistillation, supercritical solvent extraction (SCE), and solvent extraction however, advancement in unit operations introduces new techniques like ultrasonic-assisted heat extraction (UAE) and microwave-assisted heat extraction (MAE) (Perovi
c et al., 2021). The most frequently used method for the extraction of Lavender essential oil (LEO) is hydrodistillation. This method is preferred at a commercial level over other methods despite its drawbacks as it is much time-consuming, performed at a high temperature which can degrade its bioactive components. Hydrodistillation can take time from 1 to 10 h dependent upon the genotype, reproduction, and morphological condition of the flower. The quantity of isolate is determined by the total given time to the process, the temperature, the pressure, and the type of plant material used. Not only for the extraction of LEO but hydrodistillation is also preferred for the extraction of several other oils and bioactive components. A comparative study designed by Fagbemi et al. (2021), in which Soxhlet extraction SE

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and hydrodistillation HD is compared and the outcomes showed that soxhlet extraction is better in terms of quantity (yield) but by the use of the Clevenger method (hydrodistillation) good quality oil can be extracted as it contains oxygenated compounds which can impart better aroma in the isolate. Hydrodistillation is commonly done through the Clevenger apparatus in which plant materials are dipped in to boiling water or steam during distillation to evaporate the essential oil within them. The steam with phenolic compounds are collected and segregated in a jar known as a “Florentine flask” as they condense. Although distillation looks to be a simple method of extracting essential oils. However, advancement in this process leads the seekers toward the invention of new techniques, and many distillation-associated techniques are introduced for the extraction of essential oils. Many distillation techniques such as hydrodistillation, steam-distillation, turbo-distillation, salt-hydrodistillation, enzyme-hydrodistillation, ultraviolet-assisted extraction (UAE) hydrodistillation, subcritical water hydrodistillation, microwave-assisted extraction (MAE), steam hydrodistillation, and micelle-hydrodistillation. Lavender essential oil is enriched with polyphenols which are highly volatile compounds, to preserve their phenolic contents should be the priority in the whole process of extraction.

4.5 Structural and nutritional characterization Lavender is an important aromatic and medicinal plant native to the northwest Mediterranean, it is stress-tolerant and grows well in hot climates. L. angustifolia and L. intermedia are two of the most important species in the genus Lavandula. Both species are cultivated primarily for the extraction of oil, which is utilized in the aromatherapy as well as in perfume and cosmetic (Woronuk et al., 2011). Essential oils are a rich source of phenolic components which vary from species to species. Among all species, oil isolated from L. angustofolia (also called English Lavender) is one of the most supreme and precious oils due to the low contents of camphor (0%–0.6%), which imparts the pungent or medicinal smell in the oil. Lavender oil is utilized in aromatherapy due to presence bioactive compounds include linalool and linalyl acetate due to its peculiar therapeutic mechanisms. The quantification of bioactive compounds can be influenced through plant material, extraction technology, soil, and climatic conditions. Many studies are conducted at different scales to characterization the lavender oil. Linalyl acetate and linalool are the major compounds reported by (Camen et al., 2016) which comprises 30.398% and 23.609%, respectively, which becomes more than half of the total concentration. Characterization of wild lavender plant oil reported by Despinasse et al. (2020) in which linalyl acetate, linalool, and caryophyllene oxide are the main constituents. Another French chemotype was discovered in the south of the Massif Central and contained lavandulyl acetates as major ingredient. These results depict that biochemical composition of essential oil change with the change in their conditions. Similar study conducted through GC-MS and GC-FIR designed by (Truzzi et al., 2021) concluded that lavender oil is mainly composed of 41 phenolic compounds in which linalool (40.38%), linalyl acetate (27.00%), terpinene-4-ol (3.94%), and cis-ocimene (7.67%) present in major concentration.

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Many other studies conducted through GC-MS on L. angustifolia reported that Eucalyptol (52.36%), camphor (11.91%), endoborneol (8.775%), and gamma-terpinene (8.775%) are present as a main phenolic component.

4.6 Chemistry and their properties 4.6.1 Linalool Linalool (2,6-dimethyl-2,7-octadien-6-ol) monoterpenoid with a methyl group at positions 3 and 7 as well as hydroxyl group found at position 7 (National Center for Biotechnology Information, 2021), abundantly present in essential oils with a molecular weight of 154.25 (Fig. 4.1). It is present in a number of fragrant plant species, many of which are employed as analgesics and antiinflammatory medicines in traditional medicine (Letizia et al., 2003) (Table 4.2). Linalool is the major component of many essential oils, and these monoterpene molecules are responsible for a variety of biological functions (Peana et al., 2003). In a study conducted by de Moura Linck et al. (2009), in which mice were placed in an inhalation apparatus for 60 min in an environment comprising either 1% or 3% linalool after which they observed that linalool has a good anxiolytic effect. The same type of study designed by Shaw et al. (2007) depicted that linalool has a great therapeutic as well as dermatological potential due to which it is used in many industries. Linalool has antitumor, neurological, antimicrobial, anxiolytic, antidepressants, cardio-protective, renal protective, and lung-protective properties (An et al., 2021).

FIG. 4.1 Chemical structures of bioactive compounds of lavender oil.

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4.6 Chemistry and their properties

TABLE 4.2

Bioactive compounds of lavender oils and their therapeutic potential.

Bioactive compound

Therapeutic potential

References

Linalool

Antitumor, antimicrobial, anxiolytic and cardio-protective

An et al. (2021) and Harada et al. (2018)

Linalyl acetate

Obstructive pulmonary disease (OPD), antispasmodic, antihyperpigmentation hypertension, serum lipid peroxidation and vascular cytotoxicity

Hsieh et al. (2019) and Moon et al. (2018)

Eucalyptol

Antiinflammatory antioxidant, airway mucus hypersecretion, pancreatitis. Colon damage and neurodegenerative diseases

Seol and Kim (2016)

Carvacrol

Antiinflammatory and antioxidant potential in respiratory disorders, anticancer, antifungal, antibacterial, antioxidant, antiinflammatory, vasorelaxant, hepatoprotective

Carvalho et al. (2016) and Silva et al. (2018)

α-Terpineol

Antidiarrheal, analgesic, antimicrobial, anticholesteremic and reliever in neuropathic pain

dos Santos Negreiros et al. (2019), Soleimani et al. (2019), Li et al. (2014), and de Sousa et al. (2020)

4.6.2 Linalyl acetate Linalyl acetate (1,6-octadien-3-ol,3,7-dimethyl acetate) (Fig. 4.1) is an aromatic component found in a variety of perfumes. It has many nonfood applications and is used as a functional component in different products such as decorative cosmetics, premium scents, shampoos, deodorizers, and other utilities include noncosmetic items like detergents and cleaners (Table 4.2). Linalyl acetate has many nutraceutical properties. It also helps to combat different chronic diseases including obstructive pulmonary disease, hypertension, blood pressure, serum lipid peroxidation, and vascular cytotoxicity. A study designed by Hsieh et al. (2019) concluded that linalyl acetate is beneficial in lowering high blood pressure.

4.6.3 Eucalyptol Eucalyptol (1–8 cineol) is a terpenoid oxide (Fig. 4.1) that is extracted from many plants. It is a natural substance derived from many herbal plants that commonly used in the management of many chronic syndromes like asthma, airway mucus hypertension, and chronic obstructive pulmonary disease. Its recent studies show that eucalyptol have both food and nonfood properties. Many mouthwash and cough medication companies use eucalyptol as a constituent. It is also used in beauty and skincare industry in the treatment and prevention of acne. The oil’s antiinflammatory characteristics help to reduce redness and other inflammatory symptoms, making it a great skin moisturizer (Table 4.2).

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The US Food and Drug Administration (FDA) has approved eucalyptol in preparation of foodstuffs to improve their odor and flavor. Eucalyptol is used to flavor a variety of nutraceuticals, cakes, creams, and other foods in almost every country. Developing and underdeveloped countries must take steps to guarantee that the amount of eucalyptol used in food preparations is safe, as it has some harmful effect because its extensive use could be fetal and consumer can face stomach pain, dizziness and muscle weakness due to some allergic reaction in the body.

4.6.4 Carvacrol Carvacrol (isopropyl-o-cresol-o-thymol) is indeed a monoterpenic phenol produced by converting-terpinene to p-cymene (Fig. 4.1). As a result, these two chemicals can be found in the essential oils (EO) of L. pubescens. It is a plant metabolite that has many pharmacological properties like destruction of viral proteases and angiotensin-converting enzymes which lower blood pressure. Moreover, it imparts the flavor in foodstuffs for which used as additive and also prolongs the shelf life of food items. Therapeutic potential of carvacrol have been demonstrated in many research studies. Multiple pharmacological studies have been discovered in vitro and in vivo, include anticancer, antifungal, antibacterial, antioxidant, antiinflammatory, vasorelaxant, hepatoprotective, and spasmolytic properties which increase its significance in pharmaceutical as well as in food processing industry (Table 4.2).

4.6.5 α-Terpineol α-Terpineol is a tertiary monoterpenoid alcohol with sensory qualities that are widely used in the flavors and perfumes sector (Fig. 4.1). It can be found in a variety of natural sources, but biochemical hydration with turpentine and α-pinene is the most common method to produce synthetically. Furthermore, the literature has numerous reactions to prepare synthetically through microorganisms by biotransformation of monoterpenes. Apart from its conventional usage, α-terpineol has been studied in various domains like medicine and cosmetics, since it exhibits biological qualities other than scent, such as antioxidant, antiproliferative, antibacterial, antiinflammatory, and certain analgesic actions. Moreover, nowadays it has a central role in many pharmacological applications like diarrhea (dos Santos Negreiros et al., 2019), analgesic (Soleimani et al., 2019), antimicrobial (Li et al., 2014), anticholesteremic (de Sousa et al., 2020) as well as in reliever of neuropathic pain (Table 4.2).

4.7 Therapeutic potential 4.7.1 Aromatherapy Aromatherapy is the medical application of herbal plant’s oils and odorous extracts for a number of therapeutic purposes, involving mood enhancement, disease healing and prevention, improved sleep and cognition, and pain relief (Barcan, 2014). Aromatherapy’s most frequent therapeutic modalities include inhalation and massage. Lavandula essential oils have been proven to reduce the effects of sleep-related disorders in a variety of people, involving

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93

middle-aged patients in a postpartum insomniac woman, intermediary care unit, dementia patients in a care facility, healthy students, young infants, and insomniac women (Lytle et al., 2014; Afshar et al., 2015). The oil did not affect the patient’s primary symptoms in a medical investigation on palliative care patients. On the other hand, on the second day following oil administration, the oil generated a deeper sleep. Patients were able to fall asleep and then wake up because of the oil. The oil also improves the quality of sleep. On the first and second days, the oil decreased arousal regularity; however, after oil administration, the oil increased overall sleep quality (Yıldırım et al., 2020). Premenstrual emotional symptoms can also be relieved with lavender oil. Lavender has been shown to help decrease premenstrual emotional symptoms and the variety of symptoms associated with the premenstrual period, generally known as PMS, in women of reproductive age. These advantages were obtained by aromatherapy treatment. Lavender aromatherapy has been shown to help with premenstrual emotional issues (Sharma et al., 2019). Furthermore, alternative study discovered that massage with lavender essential oil was useful in lowering pain and length of labor, which was attributed to the analgesic qualities of linalool (Zahra and Leila, 2013; Janula Raju, 2014). Inhaling scented mixtures including Lavandula essential oil has been found to reduce postsurgical discomfort in women after cesarean deliveries (Olapour et al., 2013). The therapeutic potential of lavender oil is shown in Fig. 4.2.

4.7.2 Antidepressant Lavandula essential oils have been shown to offer significant psychological benefits, including improved stress, neurological function, anxiety, and depression. Both young infants

FIG. 4.2 Therapeutic potential of lavender oil.

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and adults have reported reduced tension and enhanced relaxation after bathing with Lavandula essential oil, either directly or indirectly as a component of scented bath gels (Field et al., 2008). Lavender oil was used to cure restlessness and anxiety, and it also helped people relax (El Sayed et al., 2020). Tinctures and Infusions made from lavender flowers have soothing and analgesic properties. Silexan is a lavender oil that is available in 80-mg gelatin capsules. Within 2 weeks, Silexan was found to have an anxiolytic or anxiety-reducing impact on patients with generalized or subsyndromal anxiety (Sharma et al., 2019). In clinical research, the oil reduced anxiety following inhalation. Respiration was reduced and oxygen saturation was raised as a result of the oil. As a result, the oil reduced anxiety and other main symptoms in people with benign prostatic hyperplasia (Genc and Saritas, 2020). Another clinical trial found a link between bone marrow biopsy and anxiety. In some people, oil inhalation is useful in reducing anxiety. This oil is used to alleviate hematological and oncological symptoms, as well as to reduce anxiety brought on by bone marrow biopsy (Abbaszadeh et al., 2020).

4.7.3 Antimicrobial Lavender oil is effective against a wide range of bacteria, even those that are resistant to antibodies, such as methicillin-resistant enterococcus. Lavender oil has also been discovered to be an efficient antifungal agent against fungi of medical and agricultural value (Sharma et al., 2019). The oil had a stronger effect on both Gram-positive and Gram-negative bacteria, but it did not affect Gram-positive cocci growth. The lavender essential oil has good antimicrobial activity against many Gram-negative and Gram-positive bacteria. The Gram-negative bacteria include E. coli and P. aeruginosa while Gram-positive bacteria include B. subtilis and S. aureus. Depending on the strain, lavender oil inhibits their development at concentrations of 0.4–1.8 g/mL. The minimum inhibitory concentration (MIC) values for all of the lavender essential oils were 1.5–5 times lesser than those for bacteria, indicating that they were far more active against the yeast Candida sp. (Smigielski et al., 2018). The oil reduced the number of mixed microbiota cells on the surface of the skin (Biało
n et al., 2019). In a clinical trial, around 300 patients with acute viral rhinosinusitis who were treated with the oil showed meaningful improvement in symptom scores and improved the health. As a result, oil treatment in adult patients reduced all indications of acute viral rhinosinusitis (Dejaco et al., 2019). In additional clinical trials, the oil improved life safety and alleviated viral symptoms in about 260 individuals with acute bronchitis. As a result, oil is useful in the treatment of severe viral symptoms in adults (K€ahler et al., 2019).

4.7.4 Antioxidant Against lipid peroxidation, lavender essential oil showed the stronger antioxidant activity in a linoleic acid model against different pathogens. Lavender oil has antioxidant properties because of its phenolic component such as carvacrol. It is also protected the food products from oxidative rancidity. It is responsible for the inhibition of the ROS chain by the reduction of reactive oxygen species (ROS). Thus, lavender oil can be used to prevent disorders including Alzheimer’s disease, brain dysfunction, adiposity, cancer, cardiovascular diseases (CVD), and immune disorders that are caused by oxidative stress induced by free radicals (AliShtayeh et al., 2020).

4.7 Therapeutic potential

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4.7.5 Cardioprotective In healthy adult men, lavender aromatherapy has been shown to have beneficial results on heart-related diseases, including enhanced relaxation, lower serum cortisol levels, and improved coronary circulation with enhanced coronary flow velocity reserve (CFVR) (Shiina et al., 2008). The oil prompted olfactory in stroke patients with anxiety in a clinical investigation, which increased diastolic blood pressure with higher levels of typical worry symptoms (Iokawa et al., 2018). Systolic and diastolic blood pressure was reduced by Lavandulae aetheroleum oil. The oil reduced heart rate, as well as systolic and diastolic blood pressure (Ogata et al., 2020; Saritas et al., 2021).

4.7.6 Antiinflammatory Lavender oil has antibacterial and antiinflammatory properties, making it useful for treating small burns and bug bites. Lavandula aetheroleum oil alleviated depressive symptoms. The oil had a neurogenic impact, meaning it boosted neurogenesis and increased dendritic complexity. The oil also increased oxytocin levels in the blood (Sa´nchez-Vidan˜a et al., 2019). The oil improved the psoriasis area severity score by 73.67% and the Thymus-17 cytokines by 87%. Linalool and linalyl acetate, the oil’s two main ingredients, exhibited a 64% and 47.61% recovery in psoriasis area severity index scores, respectively. Thymus-1 tumor necrosis factor and interleukin-1 were recovered using linalool and linalyl acetate. Thymus-17 cytokines were retrieved using linalool (interleukin-17 and interleukin-22) (Rai et al., 2020).

4.7.7 Digestive system Lavender tea can aid with digestive problems such as nausea, vomiting, bloating, upset stomach, and abdominal edema (Sharma et al., 2019).

4.7.8 Anticancer The lavender oil of L. stoechas has cytotoxic properties against human epidermoid carcinoma, hormone-dependent human prostate cancer includes breast, colon, and lung cancer (Bousta and Farah, 2020).

4.7.9 Antihair fall Lavender essential oil is beneficial for stimulating hair growth and also used as hair oil. Previous studies revealed that the use of lavender oil improve hair growth, thicken, reduce dandruff and silkiness. Lavender oil is also effective in the management of alopecia areata, or hair loss. This is a condition in which some or all of the body’s hair is lost. Hair therapy with lavender oil has been shown to minimize hair loss in 1 month and boost hair growth for 4 weeks (Sharma et al., 2019).

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4.8 Applications Due to its use in aromatherapy, cosmetics, perfumes, processed foods, pharmaceutical industries, L. angustifolia Mill. has a vast and significant influence on the global economy (Demasi et al., 2018). Lavender oil also used in dermatology to heal wounds, dermatitis, and psoriasis, as well as to increase hair growth in alopecia areata, albeit there is little proof to back this up. Aromatherapy is one of the most common uses for lavender oil, particularly for anxiety alleviation (de Groot and Schmidt, 2016). Lavender oil is supposed to have carminative, tranquillizing, antidepressive, antibacterial, antifungal, hypnotic, analgesic, and acaricidal qualities in traditional herbal medicine (Nimet and Baydar, 2013). The lavender essential oil has grown to use in aromatherapy and alternative medicine because of its medicinal advantages on central nervous system (CNS) (Wells et al., 2018). It’s used to impart flavor in beverages, ice creams, candies, baked goods, and chewing gums in many culinary industries.

4.8.1 Application in agrofood Lavender essential oil is also used as a food preservative and laxative. It has been extensively studied for its potential antimicrobial properties in foods, combatting common foodborne pathogens such as Escherichia coli O157:H7, Staphylococcus aureus, Listeria monocytogenes, and Salmonella typhimurium (Dadalioglu and Evrendilek, 2004). In comparison to gram-negative bacteria like E. coli, the oils from L. angustifolia and L. hybrida have a higher antibacterial action on gram-positive bacteria like S. aureus and Bacillus cereus (Djenane et al., 2013; Varona et al., 2013).

4.8.2 Nonfood applications Lavender was used as a bath additive by the Romans, which was one of the most valuable essential oil plants used in perfume and soap production during the middle ages. Nowadays lavender and its essential oils are sold in boutiques, grocery stores, farmers’ markets, home stores, and internet businesses all over the world (Wells et al., 2018). Perfume, cosmetics, and household chemicals all include lavender essential oil. It’s in toilet water, lotions, and aftershaves giving them a powerful top note, and it gives household cleaning products a perfume of freshness and purity. Many well-known cosmetic firms, including Avon, Procter & Gamble, and Aloe vera, sell lavender-scented products (Wells et al., 2018). In addition, the essential oils of Lavandula hybrids are used in the treatment of lice. The oil of lavender plant is being used in aromatherapy, baked goods, candles, cosmetics, detergents, jellies, massage oils, perfumes, powder, shampoo, soaps, and tea all around the world (Sharma et al., 2019). Several studies have shown that essential oil may be used as a natural preservative in cosmetics and beauty items to replace synthetic preservatives that might cause adverse responses in certain people (Cardia et al., 2021).

4.9 Safety, toxicity, and regulation

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4.9 Safety, toxicity, and regulation Consumer concerns about food quality and safety have risen dramatically in recent years. The growing desire for better, healthy, and hygiene food is reflected in research into latest technologies for food processing, preservation, transportation, and storage. Furthermore, efforts have been made to stop foodborne contaminations, which impact the number of individuals worldwide and are a major public health problem. In this regard, innovative natural solutions such as the use of essential oils have been investigated. EOs are supplementary metabolites from lamiaceae family that have sparked a lot of interest in the scientific community, not only because of their biological properties but also because of their demonstrable benefits in food and human health. Essential oils have been utilized as perfume scents, flavorings in cooking, and traditional medicine for ages. They are now being researched for their antioxidant, antibacterial, anticancer, analgesic, insecticidal, antidiabetic, and antiinflammatory effects (Ribeiro-Santos et al., 2018). When applied topically, every essential oil, whatever of the plant from which they are derived, should applied with caution, and any massage on irritated or injured skin should be prevented. Persons with a history of skin allergy, massage with lavender oil should be avoided in people who are allergic to lavender oil, as it might cause allergic symptoms and skin irritation., in general, should be given special care. Lavender oil should be diluted in a concentration of 1.5%–3.0% when used externally. If the subject’s face is involved, the dilution should be increased to 0.2%–1.5% to avoid unpleasant responses on the more sensitive facial skin. Large-scale oil exposure should also be avoided due to the risk of causing seizures and bronchospastic attacks in those who are susceptible, additionally, excessively long exposures should be avoided to avoid hypersensitivity (Antonelli and Donelli, 2020). Aromatherapy with lavender essential oil may be useful as an alternative therapy for the indicative management of a variety of situations, including psychological issues and muscle spasms benign disorders, as well as pain management for advanced incurable life-limiting illnesses. When fragrance massage is compared to massage alone, some research suggests significant extra benefits, particularly in the areas of anxiety management and benign musculoskeletal pain treatment. In general, the researched intervention appears to be safe and well-tolerated by patients, as long as therapists take all necessary safeguards. More research into the therapeutic effects of lavender scent massage is urged, particularly in the pediatric population, where published efficacy and safety data are sparse and disputed.

4.9.1 Toxicity Acute toxicity due to essential oils nearly always occurs as a result of mistakenly ingesting a large amount of undiluted oil which leads to polypnea, convulsions, nausea, and vomiting, and in extreme conditions, toxicity leads toward death. At a dose of 0.25% (v/v), Prashar et al. (2004) found that lavender oil is cytotoxic to human skin cells in vitro (endothelial cells and fibroblasts) in all cell types tested (HMEC1, HNDF, and 153BR). The cytotoxicity of the oil’s primary components, linalyl acetate, and linalool, was also tested under comparable conditions. Linalool’s activity matched that of the total oil, suggested that linalool is the active ingredient in lavender oil. The cytotoxicity of linalyl acetate was higher than that of the oil, implying that an unknown component in the oil

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suppressed its activity. Membrane injury has been suggested as a potential mechanism of action.

4.9.2 Legislations Essential oils (EOs), also known as volatile oils, are defined in the Council of Europe (2014) as “odorous products” that generally have a complex chemical composition and are obtained from well-defined plant materials through three main processes: steam distillation, dry distillation, or other appropriate mechanical processes that do not involve heating.

4.9.3 Trade, storage stability, and transportation Lavender has been used for both mummification and perfumes by the Egyptians, Phoenicians, and Arabs for around 2.500 years. Lavender varieties were first introduced to Europe in the early 1600s. The blossoms of the lavender plant, from which essential oils are extracted, are the most economically valuable portion of the plant. Lavender is one of the world’s top 15 most trafficked essential oil plants. Essential oils were worth $5.44 billion in 2017 and were exported all over the world (Pakdemirli, 2020). The top exporters in the essential oil market are the US ($697 million), India ($665 million), China ($522 million), France ($466 million), and Brazil ($409 million), while the top importers are the US ($1.27 billion), France ($444 million), Germany ($353 million), the United Kingdom ($341 million), and India ($258 million). The attractiveness of lavender produces an additional $1.7 billion in tourism in these areas each year (Germain et al., 2015). According to global revenues, the use of lavender oil in cosmetics is expected to hit $716 billion by 2025, up from $420 billion in 2018 (Pakdemirli, 2020). The lavender market is reported to have a lot of different numbers in market studies. Al-Rajab reported that the global market for lavender (including English lavender, lavandin, spike lavender, and others) oil grew from 28 million dollars in 2014 to 36 million dollars in 2017 (Bejar, 2020). Persistence Market Research, on the other hand, estimated that the global lavender oil market was worth US $76 million in 2016 and that it will be worth $124.2 million in 2024 (Bejar, 2020). According to a dataset developed using price data from multiple recent market reports, the price of English lavender oil ranged from $66 to $188/kg in 2018, whereas the price of lavandin oil ranged from $32 to 51/kg (Giray, 2018). The price appears to be influenced by the oil’s country of origin and quality, with lavender oil from France being the most expensive at $188/kg. Hungarian lavender oil, on the other hand, was almost a third of the price ($66/ kg) of French lavender oil (Giray, 2018). Bulk lavender oil prices in 2019 were around $170/kg prices can vary substantially between local markets and international markets.

4.10 Conclusion Lavender oil is an excellent source of many nutritional and bioactive components. It is used as a functional ingredient in many food, pharmaceutical and cosmetic industries. Bioactive components of lavender oil having many technological effects and act as antimicrobial,

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antioxidant, preservative, and flavoring agent in many food products. Moreover, lavender essential oil having therapeutic effect due to its bioactive composition. It is effective against hypertension, neurodegenerative, and obstructive pulmonary diseases. Conclusively, lavender oil act as antiinflammatory, antihyperpigmentation, antidiarrheal, antihair fall, and antispasmodic agent.

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Effects of biostimulants on the chemical composition of essential oil and hydrosol of lavandin (Lavandula  intermedia emeric ex loisel.) cultivated in tuscan-emilian apennines. Molecules 26 (20), 6157. ´ ., Cocero, M.J., Serra, A.T., Crespo, T., Duarte, C.M., 2013. Antimicrobial activity of Varona, S., Rojo, S.R., Martı´n, A lavandin essential oil formulations against three pathogenic food-borne bacteria. Ind. Crop. Prod. 42, 243–250. Wells, R., Truong, F., Adal, A.M., Sarker, L.S., Mahmoud, S.S., 2018. Lavandula essential oils: a current review of applications in medicinal, food, and cosmetic industries of lavender. Nat. Prod. Commun. 13 (10). 1934578X1801301038. Woronuk, G., Demissie, Z., Rheault, M., Mahmoud, S., 2011. Biosynthesis and therapeutic properties of Lavandula essential oil constituents. Planta Med. 77 (01), 7–15. Yıldırım, D., Kocatepe, V., Can, G., Sulu, E., Akıs¸ , H., Şahin, G., Aktay, E., 2020. The effect of lavender oil on sleep quality and vital signs in palliative care: a randomized clinical trial. J. Complement. Med. Res. 27 (5), 328–335. Zahra, A., Leila, M.S., 2013. Lavender aromatherapy massages in reducing labor pain and duration of labor: a randomized controlled trial. Afr. J. Pharm. Pharmacol 7 (8), 426–430.

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C H A P T E R

5 Peppermint essential oil Jaspreet Kaur and Kamaljit Kaur Department of Food Science and Technology, Punjab Agricultural University, Ludhiana, Punjab, India

5.1 Introduction Peppermint (Mentha piperita L.), an aromatic herb, belongs to family Laminaceae. It belongs to genus Mentha that comprises 25 species such as spearmint (M. spicata) and Bergamot mint (M. citrata). It is a hybrid of water mint (M. aquatica) and spearmint (M. spicata). Peppermint is also known as candy mint or black mint and is sweet in flavor. The species name pipertita of this herb is derived from Latin word piper meaning aromatic, characteristic of the variety of aroma chemicals in its leaf essential oil. It is a perennial plant grown in large areas around the globe and is especially suited to temperate and sub-temperate regions of the world. Peppermint growing areas of the world include Asia, North America, Europe, and Australia. Major growing countries include the United States, France, Russia, Brazil, and India (Peter, 2012). Peppermint plant does not grow well in dry conditions. Due to requirement of water, it is found naturally growing in areas close to a water source such as a pond or a water stream. However, excessive water can damage it. Hence good drainage is required. The plant normally grows to a height of 45–80 cm and resembles spearmint in appearance. However, its inflorescence is broader and its leaves have a long petiole. The upper surface of the leaves is smoother and darker than the lower surface. It has a purplish and hairy stem that branches toward the top. When cultivated, the crop gets ready for harvest in almost 90 days. Harvesting is done prior to rainy season. In case the season is dry, another crop of peppermint can be grown (Raghavan, 2007). Cross-breed of water mint (Mentha aquatic) and spear mint (Mentha spicata) forms peppermint (Mentha piperita L.) that belongs to Lamiaceae family (Fig. 5.1). Its production has increased over the last few decades as a precious essential oil that is used in fragrances, mint-flavored products, and pharmaceutical products (Riachi and De Maria, 2015). In 2014, global peppermint production of was 92,296 tons. Africa is the greatest producer (72,880 tons) followed by South America (7100 tons), North America (2980 tons), Europe

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00010-4

103

Copyright # 2023 Elsevier Inc. All rights reserved.

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5. Peppermint essential oil

FIG. 5.1 (A) Peppermint plant, (B) peppermint field, and (C) peppermint oil.

(2231 tons), and Asia (30 tons). Species of mentha are distinguished by a considerable chemical diversification and were described to possess a variety of chemical compounds accountable for pharmacological properties (Table 5.1). The usage of essential oils has a great history being extensively exploited in beverages, food, cosmetic, and confectionery industries. In traditional medicines, it was reported that mentha species possess cooling properties, relieve digestive symptoms, strengthen the stomach, and relieve hemorrhoids and respiratory tract problems (Kee et al., 2017). Peppermint is highly beneficial for animals and humans as an antioxidant, antimicrobial, antitumor, immunomodulating actions, antiallergenic and good for digestion (Lv et al., 2012; McKay and Blumberg, 2006). Peppermint oil has been observed as an effective and safe short-term cure for active irritable bowel syndrome (Khanna et al., 2014; Alam et al., 2013).

5.2 Production and composition Peppermint foliage has been used extensively for essential oil production throughout the _ ¸ can world. Peppermint oil is known world over for flavor as well as medicinal applications (Is et al., 2002). It has antimicrobial, antiallergenic, and antitumor properties and is used in treatment of several diseases of digestive as well as nervous systems. Several flavor, food, confectionary, and pharmaceutical industries are dependent on peppermint oil. Essential oil is one TABLE 5.1 Medicinal applications and chemical compounds in Mentha genus. Pharmacological properties

Chemical compounds accountable for medicinal applications

Antiviral

Eriocitrin, menthol, rosmarinic acid, luteolin 7-O-rutinoside, phytol hesperidin

Antibacterial

Rosmarinic acid, gallocatechin caffeic acid, luteolin, catechins, epigallocatechin gallate, isomenthone, menthone, cis-carveol, hexadecanoic acid, limonene, carvone

Antioxidant

Rosmarinic acid, ascorbic acid, α-terpinene, p-cymene, δ-terpinene, cis-carveol, 1,8-cineole, rosmarinic acid, carvonecynaroside, naringin, cryptochlorogenic acid

Anticancer

Caryophyllene, Eugenol, menthone, t-cadinol, crotonate, cis-carveol and carvone menthol, naringin, cryptochlorogenic acid, rosmarinic acid

Antifungal and antiyeast

Limonene, menthol, menthone, piperitone, piperitenone oxide, carvone, caffeic acid, citronella, naringin, rosmarinic acid, cryptochlorogenic acid

5.2 Production and composition

105

of the most important commercial products of peppermint and its demand is expected to increase in the coming years. Peppermint oil has also been granted a “generally recognized as safe” status by the FDA (Food and Drug Administration). Globally, the leading producer of peppermint oil is the United States of America. According to Baslas (1970), peppermint oil production is governed by several factors such as altitude, climate, and soil as well drying conditions. For oil extraction, peppermint harvesting needs to be done during full bloom stage. Sunny and dry conditions are favorable for harvesting. For instance, in India, April to June is the preferred time for harvest. During harvest, leaves have a moisture content of 75%–85%. For better yield, the herb is allowed to dry in shady conditions. The average yield of peppermint leaves has been reported as 15–20 ton/ha while yield of oil varies from 60 to 70 kg per hectare. Several factors such as wilting and stalking period affect the yield considerably. Drying of peppermint is an important processing operation prior to oil extraction. Several drying parameters such as method used, temperature and duration affect the oil yield and composition. Beigi et al. (2018) studied these aspects for peppermint and concluded that drying in microwave assisted drying was rapid and resulted in higher concentrations of major and minor constituents in the oil (Fig. 5.2). Major components of peppermint leaves include luteolin, rutin, hesperidin, caffeic acid, and tannins such as rosmarinic and chlorogenic acids. Other components include choline; α-carotene, β-carotene; α-tocopherol and γ-tocopherol, α-amyrin and squalene triterpenes, gums; minerals; resin (Bradley, 1992; Wichtl and Bisset, 1994; Bruneton, 1995; Leung and Foster, 1996). Peppermint leaves contain 0.5%–5.0% essential oil. Major components and their proportion in peppermint oil are given in Table 5.2. Peppermint essential oil is a composite of more than 300 compounds (Riachi and De Maria, 2015). Terpenoids are the most abundant compounds present in peppermint EO. In addition, aldehydes, alcohols, lactones, and aromatic hydrocarbons also occur, although in lesser amounts (Riachi and De Maria, 2015). Within the terpenic class, the major compounds include menthol, menthone, isomenthone, menthyl acetate, menthofurane, limonene, etc. (Kot et al.,

FIG. 5.2 Peppermint: a natural hybrid.

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5. Peppermint essential oil

TABLE 5.2 Composition of peppermint essential oil. Component

Value

Menthol (%)

26.0–46.0

Menthone (%)

16–36

Isomenthone (%)

2–8

Menthyl acetate (%)

3–7

Menthofurane (%)

2–8

Limonene (%)

2.5

Pulegone (%)

1.4–4

β-Pinene (%)

1.5–2

From Peter, K.V., (Ed.) (2012). Handbook of Herbs and Spices. Elsevier.

2019; Mogosan et al., 2017; Riachi and De Maria, 2015). The chemical structures of major components of peppermint oil are given in Fig. 5.3. Monoterpenes are the most abundant components of peppermint essential oils. Menthol is the chief constituent of peppermint oil. When cooled to a low temperature, menthol separates, particularly if some crystals are added to initiate crystallization. Menthol occurs in nature as (
)-menthol form which has (1R,2S,5R) configuration. Composition of the oil is very important as it determines value of the oil. Menthyl acetate is the major ester constituent. It possesses a very fragrant mint-like odor, to which the agreeable aroma of the oil is largely due. Menthol is the alcoholic constituent; that possesses the familiar penetrating minty odor and characteristic cooling taste. Skalicka-Woz´niak and Walasek (2014) devised a method for separation of terpenoids from peppermint essential oil using high-performance counter-current chromatography. These FIG. 5.3 Chemical structures of major components of Mentha oil. From https://www.frontiersin.org/files/ Articles/409763/fpls-09-01295-HTML/ image_m/fpls-09-01295-g001.jpg.

5.3 Extraction techniques

107

included menthol and its isomers, terpinen-4-ol, and pulegone. Isomers of menthol separated were isomenthone, neomenthol, and menthone. Using this method, components could be separated with a purity of 94%–99%. In addition, it was a faster method and could be upscaled for industrial use. Pulegone is a potentially toxic ingredient that can also be removed using the process. A study in rats showed that pulegone caused loss of weight, lower blood creatinineatonia, and some histopathological abnormalities in the liver and cerebellum (Loolaie et al., 2017). For such reasons European Union does not allow use of pulegone and menthofuran as flavoring substances in foods (EC, 2008). Even in cosmetic formulations, its use is limited to 1% (Nair, 2001). Fatty acid composition of peppermint oil varies with season (Maffei and Scannerini, 1992). It was found that when harvesting was done toward the end of flowering resulted in higher content of menthol in the oil. Harvesting after 163–178 of sowing resulted in higher content of oil and menthol contents (Duhan et al., 1975). The composition of extracted oil depends on composition of the peppermint foliage, which is dependent on stage of maturity, climate, and geographical location. Further, the processing of leaves plays a significant role in oil composition (Rohloff et al., 2005; Beigi et al., 2018).

5.3 Extraction techniques Peppermint oil is obtained from the peppermint plant prior to the flowering stage. Several methods have been followed to extract oil from peppermint plant. The text below describes some of the traditional as well as novel techniques for peppermint oil extraction (Table 5.3).

5.3.1 Steam distillation One of the most popular techniques to extract peppermint essential oil is steam distillation. It is also one of the simplest methods for extraction of oil. In this case, a boiler may be used to generate steam. Peppermint leaves are placed on a plate with perforations. This plate is placed above the opening from where inflow of steam takes place. This steam is used for distillation and extraction of oil from peppermint foliage. Since steam generation takes place outside the vessel in which peppermint leaves are placed, temperature of the material normally remains below 100°C. Essential oil is extracted from the aerial parts of peppermint using steam distillation (Ammann et al., 1999; Yazdani et al., 2002; Pino et al., 2002). Steam generation may cause degradation of oil quality if vapor pressure not controlled. Although it is an energy and time consuming process, it enables extraction of about 93% of oil (Masango, 2005). However, it may also cause flavor modification and degrade the oil quality (Spiro and Chen, 1995). Oils extracted via steam distillation have been found to have better antioxidant activity as compared to those obtained via hydrodistillation (Yildirim et al., 2004). The loss of polar compounds can be controlled by placing a bed of leafy material over the source of steam. This also improves the yield of oil (Masango, 2005; Salamon et al., 2021). The process even saves the loss of water soluble components. Kant and Kumar (2021) reviewed advancements in steam distillation. One of the innovations is the use of solar energy for steam distillation. This technology makes oil extraction more energy efficient. Further it was suggested that efficiency of

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5. Peppermint essential oil

TABLE 5.3 Comparative assessment of different techniques for peppermint oil extraction. Name of the technique

Benefits

Drawbacks

Remarks

References

Steam distillation

Good yield and recovery of water soluble components

Consumes time and energy, degrades oil quality

Popular, traditional technique

Yazdani et al. (2002), Pino et al. (2002), and Masango (2005)

Hydrodistillation

Simple; conventional technique requires temperature below 100°C

Relatively slow method

Popular technique, can be combined with newer techniques for better efficiency

Okoh et al. (2010) and Pavlic et al. (2021)

Solvent extraction

Higher yield, low temperature

High cost due to solvent use

Milder technique

Pare and Belanger (1994)

Microwave assisted extraction

Faster heating, reduced time, saving on solvent

High power microwaves may alter oil quality

–

Pan et al. (2000) and Dai et al. (2010)

Ultrasound assisted extraction

Environment friendly technology, higher yields

Optimization of process parameters is required

–

ˇ labur et al. Z (2016)

Supercritical fluid extraction

Superior in quality, clean and environment friendly, shorter extraction time

Optimization of process parameters is required

–

Radivojac et al. (2021)

Ohmic assisted hydrodistillation

Solvent free, faster, high yields and environment friendly

Safety and sustainability studies are required, high capital cost

Novel technique

Gavahian et al. (2017)

peppermint oil extraction may be increased through control of size of batch, inlet flow rate and mass flow rate. Radwan et al. (2020) designed a system for extraction of peppermint. The steam distillation system was optimized for providing higher yield, efficiency, and economy of energy use. This was achieved through changes in size of batch and flow rate of boiler inlet water.

5.3.2 Hydrodistillation Hydrodistillation is the oldest technique for essential oil extraction that involves placing the peppermint herb in water. During this process, the leaves are immersed in boiling water. This causes disintegration of cells and release of the oils. It is used normally for those oil bearing materials which are not damaged by heat in water. Oil is transported along with water vapor to a separate part of the apparatus, where it is separated on the basis of gravity € urk, 2019). The essential oil obtained is collected and stored at low temper(Akda g and Ozt€ ature (
18°C) (Pavlic et al., 2021). However, the technique needs to be standardized according

5.3 Extraction techniques

109

to the material being used. Abed et al. (2019) studied the extraction kinetics of essential oil from peppermint using hydrodistillation technique. They found that the oil extraction by this technique was a spontaneous and endothermic process. Temperature increase caused proportional increase in extraction yield. However, hydrodistillation technique does not ensure complete extraction. Certain components that have higher boiling point and are more water soluble, remain in water. Many by-products of hydrodistillation such as the hydrosol and the left over leaves have been found to contain valuable bioactive components such as phenolics and had high antioxidant activity. These hydrosols could be spray dried and incorporated into ice creams (Berktas and Cam, 2021). Moreover, certain biochemical reactions such as partial hydrolysis of esters and polymerization of aldehydes take place. Certain changes in chemical composition (as determined by GC-MS analysis) of peppermint components have also been reported by Taherpour et al. (2017). The apparatus occupies larger space and the fuel requirement is higher. These factors contribute lower efficiency and larger quantities of wastes.

5.3.3 Solvent extraction Essential oil can also be extracted from peppermint through solvent extraction. Hexane and ethanol are the common solvents. This method ensures higher yields and may not require elevated temperature. As reported by Pare and Belanger (1994) solvent extraction using hexane, a nonpolar solvent has been found to increase the rate of extraction by 180 times than to steam distillation. The efficiency of extraction varies with several factors such as type of solvent used, temperature, and ratio of sample and solvent. These factors were found to significantly affect extraction of menthofuran, menthone, and menthol from leaves of peppermint. Solvent extraction is an old, yet simple technique of essential oil extraction. With time newer techniques have evolved and are being used in combination with solvent extraction for peppermint oil.

5.3.4 Microwave assisted extraction Microwave assisted extraction (MAE), developed in the latter part of 20th century, enables prompt heating effect in comparison to traditional techniques. This procedure uses microwave energy to generate heat using ionic conduction and dipole rotation. Dielectric properties of the plant material, thus, play important role in this technique. Water in plant material gains energy from the microwaves and cause pressure to increase inside cells. This may cause their breakdown, enabling the solvent to enter and start its action (Chan et al., 2011; Routray and Orsat, 2012). It significantly curtails time for extraction and has application for a variety of plant materials including peppermint (Dai et al., 2010; Pan et al., 2000; Pastor et al., 1997; Pare and Belanger, 1994). An increase in extraction rate, and lower time of processing and solvent use make microwave-assisted solvent extraction a superior technique (Dai et al., 2010). Temperature of extraction is the most significant and one of the most investigated factors among various variables that affect efficiency of oil extraction (Nemes, 2012; Costa et al., 2014). Microwave assisted extraction (solvent-free hydrodistillation) for peppermint leaf oil was compared with traditional hydrodistillation (Kohari et al., 2020). It was found that the yield obtained was in the range of 0.88%–0.95% by treating with microwaves at 100–500 W for a

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5. Peppermint essential oil

time range of 20–90 min. This was a solvent free method with yields comparable to hydrodistillation. Pavlic et al. (2019) optimized extraction parameters for microwave assisted extraction of peppermint oil using face centered central composite design as well as artificial neural networks. Results suggested that the optimized conditions for concentration of ethanol, time of extraction and liquid to solid ratio resulted in high yields and simultaneous extraction of polyphenolic components as well as terpenoid phytochemicals. Microwave-assisted hydrodistillation has ensured faster and greater extraction of peppermints oils and reduced energy consumption and pollution (Radivojac et al., 2021). However, increasing the power of microwaves indiscriminately may cause chemical alterations in extracted oils. Optimization of such techniques will lead to more adaptable technology for oil extraction.

5.3.5 Supercritical fluid extraction Conventional essential oil extraction has been carried out by use of solvents. Supercritical fluid extraction (SFE) is safe and an environmentally friendly technology. This technology makes use of altered properties of fluids at their critical temperatures and pressures. The process involves control of several physical and chemical properties. Carbon dioxide, one of the most commonly used supercritical fluid, possesses low critical temperature, i.e., 31.1°C and critical pressure of 73.8 bar, high diffusion rate, high power of dissolving and low surface tension. These properties may also be exploited for extracting specific components of the essential oils. By controlling (lowering) pressure, the solvents evaporate from the extract and the components are recovered. This technology has been used for extraction of several sensitive compounds and essential oils. Supercritical fluid extraction has been successfully used to extract essential oils from peppermint in much shorter time than Soxhlet extraction. Since, pressure is one of the key parameters that needs to be controlled during this process, kinetic models were applied to get optimized outputs (Radivojac et al., 2021). This technique is being looked upon as a green technology for producing of peppermint oils free of solvents and extracts plentiful in terpenoids and lipophilic phytochemicals (Pavlic et al., 2021).

5.3.6 Other methods Other methods employed for peppermint oil extraction include reflux temperature extraction, room temperature extraction, and ultrasonic assisted room temperature extraction and ohmic assisted hydrodistillation. Yield of peppermint oils by ohmic assisted hydrodistillation was further improved electrolyte treatment of mint leaves (Gavahian et al., 2017).

5.4 Characterization of peppermint essential oil components Several techniques have been employed for analyzing components in essential oils. Gas chromatography and gas chromatography-mass spectrometry is a popular technique used for identifying and quantifying components of peppermint oil. Gherman et al. (2000)

5.5 Properties of peppermint essential oils

111

identified major volatile compounds in of M. piperita by the gas chromatography-mass spectrometric analysis. These included menthone, menthol, isomenthone, menthyl acetate, limonene, 1,8-cineole, carvone, and beta-myrcene. Dominant fatty acids in peppermint oil include palmitic acid (16:0), linoleic acid (18:2), and linolenic acid (18:3) (Maffei and Scannerini, 1992). Sixteen flavonoids isolated from leaves of M. piperita were characterized as lipophilic aglycones. Voirin et al. (1994) carried out a research on free aglycones of M. piperita. The study that took nearly 2 months concluded that the flavonoid pattern whole peppermint plant was invariable. Principal component analysis (PCA) of the results revealed three groups of flavonoids, equivalent to three groups of terpenoids. A study involving the variation of photoperiod revealed that pattern of flavonoids is significantly affected by length of a day. Solid phase microextraction-gas chromatography-mass spectrometry offers a rapid yet simple solution for analysis of volatile components. This technique was employed for evaluation of bioactive chiral terpenes in M. piperita plants from different biological origin. This technique was, in particular effective, in identifying the variability in enantiomeric distribution of the terpenes (Del Castillo et al., 2004). Results revealed very limited variability for enantiomeric composition of chiral terpenes. Hence, despite differences in geography, composition of terpenes was nearly the same. This finding could be particularly helpful to identify adulterants in essential oil.

5.5 Properties of peppermint essential oils Peppermint oil may be colorless, greenish, or yellowish and has a typical strong odor and a, camphor-like burning taste. On storage, it may become thicker and reddish. However, it can be stored for 10–14 years without losing its quality. It is highly volatile and hydrophobic oil (Riachi and De Maria, 2015). The content of essential oil in peppermint leaves varies from 1.2% to 3.9% (v/w) of oil (Alankar, 2009; Riachi and De Maria, 2015). A number of factors cause variation in yield of oil. These include physiological age of the plants, soil, type of climate, fertilizers, and soil health. The chemical properties vary significantly with the techniques applied for extraction which include distillation techniques and experimental parameters (Orio et al., 2012; Rodrı´guez-Solana et al., 2015).

5.5.1 Antimicrobial properties Antimicrobial assay of essential oils (EOs) are generally tough due to their insolubility in water, volatility, and complex chemistry. Essential oils from Mentha species added into juices from fruits and vegetables could effectively inhibit or reduce spoilage and pathogenic microorganisms. EO’s mechanism of action yet not completely understood (Mamadalieva et al., 2020). Reports suggest that the action of antimicrobial compounds increase the permeability of membranes. EO’s inhibit microorganisms by different mode of action such as lipophilic or hydrophilic character of EO’s, membrane protein damage, destabilization of bacterial membranes and proton motive force depletion. Thus, it causes lipid splitting of microbial cell membranes and mitochondria that lead to lysis of cell and discharge of cell contents. Peppermint EO’s showed excellent antimicrobial activity against Escherichia coli, Salmonella pullorum,

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5. Peppermint essential oil

Streptococcus thermophillus, Comamonas terrigena, Lactobacillus bulgaricus, Staphylococcus pyogenes, Staphylococcus aureus, Salmonella typhi, Mycobacterium avium, Proteus vulgaris, Enterobacter aerogenes, Yersinia enterocolitica, and Shigella dysenteriae (Bohnert et al., 2016; Sun et al., 2014). EO’s from two menthe species were analyzed for its antibacterial properties against seven microorganisms: Salmonella spp., Enterobacter cloacae, Klebsiella pneumoniae, Staphylococcus aureus, E. coli, and Streptococcus pyogenes. Results of antibacterial activity performed by agar disk diffusion technique ranged between 7 and 14 mm of growth inhibition zone. Additionally, both EO’s showed relatively similar antibacterial property against the selected Gram-negative bacteria. However, there was a variation for the antibacterial activity against Gram-positive bacteria (Plˇuchtova´ et al., 2018). Table 5.4 summarizes some of the latest studies on efficacy of PO as antimicrobial agent.

5.6 Applications of peppermint essential oil PEO is the most extensively used oil among all essential oils. It has been used for centuries to treat multiple illnesses such as headaches, colds, digestive problems, antiseptic, antispasmodic, diaphoretic, carminative, antimicrobial, stimulant, and antiemetic. Peppermint oil is also used as a flavoring agent, in aromatherapy, to kill germs, to reduce vomiting, flatulence, muscle spasms, etc. Currently, it has been used to treat Crohn’s disease, irritable bowel syndrome, gallbladder and biliary tract disorders, ulcerative colitis, liver complications, and menstrual cramps.

TABLE 5.4 Efficacy of peppermint oil as antimicrobial agent. Type of essential oil

Microorganisms

Main findings

References

Two species of Mentha piperita EO from Slovakia and from Italy

Salmonella spp., Enterobacter cloacae, Klebsiella pneumoniae, Staphylococcus aureus, Escherichia coli, and Streptococcus pyogenes

Antibacterial activity through agar disk diffusion method ranged between 7 and 14 mm of growth inhibition zone. Both EO’S revealed relatively same antibacterial activity for the selected Gram-negative bacteria. But, there was a variation in antibacterial activity for Gram-positive bacteria

Plˇuchtova´ et al. (2018)

Different extracts of Mentha piperita and peppermint oil

Gram-positive and gramnegative bacterial strains

Agar well diffusion method was used to determine antimicrobial activity These results presented the strong antioxidant and

Singh et al. (2015)

5.6 Applications of peppermint essential oil

TABLE 5.4

113

Efficacy of peppermint oil as antimicrobial agent—cont’d

Type of essential oil

Microorganisms

Main findings

References

antibacterial activities of peppermint oil. The results were comparable with antibiotic gentamycin Peppermint and clove oil

Candida albicans

Peppermint and clove oil at conc. From 0.015 MIC (minimal inhibitory concentration) to 0.5 MIC significantly altered the enzymatic abilities of C. albicans and these variations were majorly linked with the decrease of activity of all nine enzymes that were detected in the untreated yeast

Rajkowska et al. (2017)

Peppermint oil and its microemulsion

Clostridium perfringens

C. perfringens is a type of drugresistant intestinal pathogens that causes necrotic enteritis disease, causing huge economic loss in poultry farms. This study suggested the potential efficacy of PO and its microemulsion in the lowering of necrotic enteritis lesions and count of C. perfringens

Sorour et al. (2021)

PEO or Mentha of Pancalieri

Candida sp., Cryptococcus neoformanus, and Trichophytonmenta grophytes

PEO act as an effective antifungal source and a natural adjuvant for the cure of fungal infections

Tullio et al. (2019)

Menthapiperita EO

Bacteria: Micrococcus flavus, S. aureus, Staphylococcus epidermidis, Bacillus subtilis, and Salmonella enteritides Fungi: Fusarium tabacinum, Alternaria, Fusarium oxyporum, Penicillum spp., and Aspergillus fumigates

EO from Mentha piperita sp. Natural source) possess antimicrobial activity

Desam et al. (2019)

PEO loaded on poly ε-caprolactonelectrospun (PCL) fiber mats

E. coli and S. aureus

PCL electrospunfiber mats loaded with PEO with antibiotic-free antibacterial activity as encouraging option for healing of wounds

Unalan et al. (2019)

Menthapiperita EO

Listeria monocytogenes, S. aureus, Pseudomonas syringae,

S. epidermidis (MIC ¼ 0.625–2.5 mg/mL), L. monocytogenes

_ ¸ can et al. Is (2002) Continued

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5. Peppermint essential oil

TABLE 5.4 Efficacy of peppermint oil as antimicrobial agent—cont’d Type of essential oil

Microorganisms

Main findings

References

S. epidermidis, Xanthomonas campestris

(MIC ¼ 0.156–0.625 mg/mL), Campestris pv. phaseoli (MIC 0.07–1.25 mg/mL)

Menthapiperita EO

S. aureus ATCC 25923, S. saprophyticus ATCC 15305, S. epidermidis ATCC 14990, E. faecium ATCC 25788, E. faecalis ATCC 29212, S. sanguis ATCC 10566, S. salivarius ATCC 9222, S. pneumoniae ATCC 33400, S. pyogenes PTCC 1447, S. agalactiae, S. mutans ATCC 35668, S. sobrinus ATCC 27607, B. subtilis ATCC 6051, Bacillus cereus PTCC 1247,E

The oil had bactericidal effect against S. typhimurium, S. mutans, Sh. Flexeneri, P. aeruginosa, C. albicans, Sh. dysenteriae and A. parasiticus. PEO MIC values were higher against E. faecium, E. faecalis, and C. albicans showed more sensitivity to PEO and the oil had a bactericidal effect on it (MIC ¼ 0.125 μL/mL)

Mahboubi and Kazempour (2014)

Mentha piperita EO

Clostridium hystoliticum, C. perfringens, Clostridium butyricum, C. intestinale, C. ramosum

Highly sensitive to C. intestinale. C. butyricum showed higher susceptibility in tested EO (6.35 mm)

Kaca´niova´ et al. (2014)

Mentha piperita EO

P. aeruginosa, S. aureus, K. pneumonia, Staphylococcus sp., E. coli, Proteus

EO has been disclosed moderate activity against strains of K. pneumonia, Proteus and S. aureus, Staphylococcus sp. (with a diameter of inhibition (13.16, 13.33, 12.66, and 13.43 mm) and MIC (0.5, 0.25, 0.66, and 0.5 μL/mL, respectively)

Goudjil et al. (2015)

Mentha piperita EO

C. tropicalis (INCQS 40096, origin ATCC 28707), C. albicans (INCQS 40277, origin ATCC 90028), S. cerevisiae (INCQS 40001 origin ATCC 2601), P. anomala (INCQS 40101, ATCC 16763)

Effective to inactivate P. anomala, C. albicans, C. tropicalis, and S. cerevisiae at 1.875, 3.75, and 7.5 μL/mL

da Cruz Almeida et al. (2019)

M. pulegium, M. piperita, M. longifolia, M. spicata, M. suaveolens, M. aquatica, M x piperita (two hybrids EtOH extract)

E. coli KF 918342, S. haemolyticus, A. salmonicida KACC 15136, E. coli ATCC 35150, C. sakazakii ATCC 29544, and A. hydrophila KCTC 12487

Ethanolic extracts of nine mint species showed remarkable activity against S. haemolyticus. The extracts from horsemint, chocolate mint, and pennyroyal mint which principally containp-methan3-one and menthol lead to high antimicrobial activity

Park et al. (2016)

5.7 Toxicity associated with usage of peppermint essential oil

115

5.6.1 Relieves pain Menthol has been used to cure pain from migraine headaches, tension headaches, and other causes. A study evaluated the topical applicability of a 10% menthol liquid for the treatment of migraine. They found that when applied to the temples and forehead of the participants, they had a long duration of relief from pain and less light sensitivity and nausea as compared to placebo (St Cyr et al., 2015). In another study the effect of peppermint oil tablets on persons having difficulty in swallowing and noncardiac chest pain. More than half participants reported improvement in symptoms (Khalaf et al., 2018). Distal esophageal spasm (DES) is a rare motility disorder reported mainly in females having symptomatic motility disorder. Elderly female patients received symptomatic relief from peppermint oil (Parvataneni and Vemuri-Reddy, 2020). Further, another study evaluated the effect of nanoemulsion containing rosemary and peppermint essential oils in rats having osteoarthritis. The nanoemulsion with essential oils of rosemary and peppermint reduced the osteoarthritis pain through the increase in antioxidant capacity and enhancing the histopathological attributes of rats’ knee joint (Mohammadifar et al., 2021).

5.6.2 Cures irritable bowel syndrome (IBS) The exact cause of IBS is unknown; it can lead to uncomfortable symptoms that include bloating, stomach cramps and pain, diarrhea, gas, and constipation. Dietary and lifestyle changes can lessen these symptoms. PO is a natural solution that makes digestion more comfortable. PO contains L-menthol that blocks calcium channels in smooth muscle and generate antispasmodic effect on gastrointestinal muscles. Additionally, PO also possess antimicrobial, antioxidant, antiinflammatory, anesthetic activities, and immune-modulating, all of which are relevant for the treatment of IBS (Alammar et al., 2019; Black et al., 2020). PO is often used to treat IBS, despite a need of evidence for potency from high-quality trials. In one study the safety and efficacy of small-intestinal-release PO in persons with IBS and investigated the influence of targeted ileocolonic-release PO. In one of the randomized trial of persons with IBS, it was found that neither ileocolonic-release nor small-intestinal-release PO (8 weeks) generated statistically significant decrease in response to abdominal pain or overall relief of symptoms. The small intestinal-release PO did significantly reduce the abdominal pain, IBS severity, and discomfort (Weerts et al., 2020).

5.7 Toxicity associated with usage of peppermint essential oil Essential oils of medicinal plants are often considered as safe, side effects of peppermint EO are not very severe in multiple studies. However, no long term toxicity studies on humans are available in literature but in sensitive human beings it may cause allergic reactions. Peppermint EO like many other EO’s can interact with other herbs, drugs, or supplements. One study reported that spearmint and Mentha piperita tea can deprive human beings of iron that further causes anemia upon excessive consumption (Akdo gan et al., 2007). G€ urb€ uz (2020) reported that pulegone which occur in low level in menthe piperita oil extracts acts hepatotoxic, and Douros et al. (2016) assessed a likely liver injury upon consumption of M. piperita.

116

5. Peppermint essential oil

Another study reported that pulegone (its metabolite menthofuran) and menthol could be hepatotoxic that occur in small quantities in M. piperita (Balakrishnan, 2015). American College of Gastroenterology had suggested lowering the intake of peppermint as it is risky for lifestyle changes and GERD (gastroesophageal reflux disease) ( Jarosz and Taraszewska, 2014). Peppermint EO has been reported in blockage of bile ducts, severe liver failure, and gallbladder inflammation (Balakrishnan, 2015). In another study, Zong et al. (2011) observed that peppermint EO stimulated bile secretion and involved in regulating the bile fluid synthesis related gene, i.e., nuclear bile fluid receptor farnesoid X receptor mRNA and cholesterol 7α-hydroxylase. Peppermint EO could result in bradycardia, muscle tremor, heartburn, contact dermatitis, hypersensitivity reaction, jaundice in newborn babies, and abdominal pain (Sharma et al., 2014). Earlier studies reported that menthol and peppermint both possess Ca2+ channel obstructing properties that might show their mechanism of effectiveness against irritable bowel syndrome in the clinic. However, peppermint use in some patients results in oral symptoms like oral ulceration and burning mouth syndrome. So peppermint is not recommended for persons who: • Have diabetes as it can increase the chances of hypoglycemia or low blood sugar. • Have gastroesophageal reflux disease (GERD). • Have a hiatus hernia. Peppermint in capsule form should not be used in combination with antacids, because antacid breaks the coating of capsule very rapidly and thus increases the risk of heartburn.

5.8 Conclusion and future perspective Since earlier times, mentha species and its EO’s have attracted the scientific world with their pharmaceutical, cosmetic, biotechnological, and food industry applications. Regarding properties of PEO, it can be stated that PEO has enormous ability to cure multiple human ailments such as inflammation, gastric disorders, stomachaches, parasites, nausea, digestive disorders, headaches, fevers, treating tumors, earache, and skin diseases. Researchers need to standardize the levels for safe human use and there is need to explore more regarding physicochemical properties and reactions or side effects/harmfulness during intake of PEO. This oil possesses significant antimicrobial properties and thus there is need to investigate these oils to lessen microbial drug resistance challenges. Additionally, mode of action of PEO should be assessed by conducting clinical and in vivo studies.

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C H A P T E R

6 Sandalwood essential oil Tridip Boruaha, Prastuti Parashara, Chayanika Ujira, Suraj Kr. Deya, Gulzar Ahmad Nayikb, Mohammad Javed Ansaric, and Amir Sasan Mozaffari Nejadd a

P.G. Department of Botany, Madhab Choudhury College, Barpeta, Assam, India bDepartment of Food Science & Technology, Government Degree College Shopian, Srinagar, Jammu & Kashmir, India cDepartment of Botany, Hindu College Moradabad (Mahatma Jyotiba Phule Rohilkhand University Bareilly), Bareilly, India dSchool of Medicine, Jiroft University of Medical Sciences, Jiroft, Iran

6.1 Introduction People use varieties of plant-based products in their daily life for obvious reasons. One of these products is an essential oil, which is extensively used by people since ancient times. Essential oils are volatile, natural, and odoriferous substances extracted from different parts of plants (Sharmeen et al., 2021). Interestingly, these are also known as ethereal oil in several countries and some researchers also developed a liking for the term. Essential oils are accumulated in various plan parts such as secretory cavities, glands, resin ducts or secretory hairs, and secretory ducts (Djilani and Dicko, 2012). One of the most commonly and extensively used essential oil can be extracted from sandalwood trees known as sandalwood essential oil. Sandalwood trees are small, evergreen, hemiparasitic plants. The sapwood is odorless and white in color and the heartwood which contains the essential oil has a pleasant smell and is yellow-brown in color. Leaves are subacute glabrous, entire and elliptic lanceolate with thin base acute; inflorescence of sandalwood trees are cyme which is shorter than leaves and the length of the petioles fall in the range of 1–1.3 cm. Flowers are brownish-purple in color, present terminally and axillary paniculate cymes; fruit is a drupe, 1.3 cm in diameter, purple black colored; the seed is solitary (Roy et al., 2017). Sandalwood trees are observed to be able to grow in diverse types of soils such as sand, clay, loam, black-cotton soil, and laterite, even very poor and rocky soils as well (Das, 2021). It attains a height up to 60–65 ft. and generally occurs at an altitude of 2000–3000 ft. Sandalwood trees require 20–25 cm of rainfall per year for

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their growth and development. An average Sandalwood tree takes more than 30 years to attain its maturity (Sindhu et al., 2010). The family Santalaceae has 400 species across 30 genera in temperate and tropical areas all over the world. About 25 species of genus Santalum are found predominantly in India, Australia, Malaysia, and Pacific islands (Brand, 2000). Some important species of genus Santalum are Santalum spicatum, S. album, S. acuminatum, S. pyrularium, S. lanceolatum, S. murrayanum, S. obtusifolium, S. boninense, S. elipticum, etc. Mainly Australian sandalwood (Santalum spicatum) and Indian sandalwood (Santalum album) are extensively used in the extraction of essential oils. Santalum album (Indian sandalwood) is also known as “Chandana” in India. Apart from these, Santalum paniculatum is found in Hawaii; Santalum yasi is extensively reported from Samoa, Fiji, and Tonga; Santalum austrocaledoicum is reported from New Caledonia, Papua New Guinea, and Indonesia, and also used in the essential oil production process (Harbaugh, 2007). The roots and heartwood of sandalwood which is yellowish-brown in color and contains essential oil; although the bark and sapwood are white in color does not contain essential oil. It can be extracted by steam distillation method from its root and heartwood. Amount of essential oil production in sandalwood tree increases with the increase in age as heartwood formation increases with time (Subasinghe et al., 2013). As a consequence of spike diseases and illegal poaching, the population of this plant is decreasing significantly; therefore International Union for Conservation of Nature and Natural Resources (IUCN) included this tree in the red data list of threatened species (Misra and Dey, 2013). The chemical compositions of sandalwood essential oil significantly vary in young and mature trees. Some of the major chemical constituents of sandalwood essential oils are cis-β-santalol, 2(E),6(E)-farnesol, sesquiterpene alcohols, cis-αsantalol, (Z)-nuciferol, α-trans-bergamotol, (Z)-α-santalol, epi-cis-α-santalol, epi-α-bisabolol, and (Z)-β-santalol; minor chemical constituents are cis-lanceol, epi-α-santalene, as γ-curcumene, α-santalene, α-bergamotene, trans-β-santalol, α-curcumenr, β-bisabilene, hydrocarbons, β-santalene, β-curcumene, and α-bisabolol ( Jones et al., 2006; Braun et al., 2003). Sandalwood essential oil is largely used in perfumery, cosmetics, and aromatherapy industries. Sandalwood essential oils are utilized for the treatment of headaches, fever, common colds, urinary tract infection, bronchitis, burns, etc. It is also used as antiseptic, antispasmodic, vaginitis, urethritis, gonorrheal recovery, antipyretic, antiscabietic, expectorant, stimulant, diaphoretic, etc. (Djilani and Dicko, 2012). Sandalwood essential oil with other plant mixtures is found to be effective against elephantiasis, stomach illness, and lymphatic filariasis (Rohadi et al., 2000). Sandalwood oil has anticancer and tumor inhibitory properties along with antiviral, antimicrobial and antioxidant properties. Sandalwood essential oil also has an important effect on the nervous system. It has a calming and relaxing effect on nerves and reduces anxiety, depression, stress, nervous exhaustion, fear, and enhances meditations. It has insecticidal activities as it acts as a repellant of various types of pests. It has an effect on body physiology, metabolism, respiratory system, genitourinary system, and integumentary systems also (Misra and Dey, 2013). Various factors affect the quantity and quality of sandalwood essential oil including environmental factors like climate, geographic location, temperature, rainfall, altitude, soil type, etc. Another major but generally ignored factor is the sectioning of the tree, the difference in the percentage of oil constituents seen in different sections of the tree. As oil contents vary from young trees to mature trees; the age of the tree is also a factor and the amount of production of essential oil increases with increasing age. Ageing of the sandalwood essential oil sample may influence the composition of the oil as well (Moretta et al., 2017). As sandalwood trees take a very long period of time to grow its wood

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and essential oil are very expensive. Three important characters determine the value of the sandalwood tree—the volume, quality, and the concentration of the heartwood oil. So, sandalwood essential oil has an enormous value in terms of both qualitative, health and economic perspective and that’s why a comprehensive account on this topic may act as a baseline for preliminary research designs and can be extremely important for guiding future workers of this field.

6.2 Comparative account on sandalwood essential oil It is estimated that about 3000 essential oils are known and among these 150 are commercially important. One of the commercially important essential oil is sandalwood essential oil. As sandalwood tree is a valuable tree, most of the countries from the different continent of the world taking the initiative of planting sandalwood trees in their region. Some commercially important sandalwood species are Santalum album which is found in India and Timor island of Indonesia, Santalum spicatum is found in arid regions of Western and South Australia, Santalum austrocoledonium is found in New Caledonia and Vanuatu, Santalum yasi is reported from Tonga and Fiji, Santalum paniculatum is endemic to islands of Hawaii, Santalum macgregorii is found on Papua New Guinea, and Santalum lanceolatum is found in Australia. Among these the East Indian Sandalwood (Santalum album) and Australian Sandalwood (Santalum spicatum) are commercially more important than all the others mentioned (Page et al., 2010; Thomson, 2020; Nautiyal, 2019). Some of the economically important sandalwood tree species along with their properties with special emphasis on sandalwood essential oil are discussed here.

6.2.1 Santalum album (Indian sandalwood) The sandalwood tree, Santalum album L. famously called white sandalwood (in English), belongs to the Santalaceae family, safed sandalwood (in Hindi) and sriganda (in Sanskrit). Different edaphic and eco climatic conditions are needed for its growth. Few studies indicated that the finest woods are extracted from the trees of the drier regions; but the concentration of the essential oil was found very high in the trees growing mainly in the rocky soil or soils with embedded stones in it (Van Thoai and Srivastava, 2020). It is a key element of the heritage, tradition, and culture of India; sandalwood is also famously acknowledged as East Indian sandalwood and the extracted oil is known as East Indian sandalwood oil. The wellknown Santalum album L. is a hemiparasitic, evergreen tree, depends on different host species for nutrients required for photosynthesis. It attains a height up to 20 m and girth up to 2.4 m. The bark of sandalwood trees is dark grey, reddish, dark brown or nearly black, tight, but also very rough in older tress and very delicate in young ones, red in color inside (Dharani, 2011). The outer wood or sapwood is white in color and does not contain any fragrance; the central part is heartwood which is yellowish-brown in color and has a strong scent. Leaves are opposite, ovate elliptical, glabrous and have reticulate venation; fruit is a drupe, flowers are purple-brown, small, terminal or axillary clusters, paniculate cyme, red, fruits become black to purple when ripe (Kumar et al., 2015). In India, sandalwood flowers appear in the month of March and remain till April which leads to a situation where the fruit has an entire cold season to ripe. Sandalwood trees require adequately about 50–64 cm of rainfall annually for their proper growth and development. These plants grow well in the slopes of hills having loamy

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soils and are prone to damage caused by fire. Santalum album is inhabitant to northern Australia, eastern Indonesia, and Indian Peninsula. The distribution of this plant is mainly confined to the two Indonesian Island Sumba and Timor and relatively dried regions of tropical India. This species is exclusively reported from the dry deciduous forest of districts of Karnataka, Tamil Nadu, Maharashtra, and Andhra Pradesh. As it is hemiparasitic plant, it depends on various hosts for nutrients such as Pongamia glabra, Lantana acuminate, and Cassia siamea. This plant is now planted in various parts of the world such as China, Malaysia, the Philippines, Sri Lanka, Indonesia, and Northern Australia (Kumar et al., 2015). The quantity and quality of oil extracted from sandalwood tree depend upon different environmental factors, genetic factors, and the current maturity stage of the sandalwood tree. The average production of essential oil from a mature tree is 25.6% and the phytochemistry revealed the total chemical constituent of essential oil produced from young to old age varies significantly (Lunz and Stappen, 2021). The majority of essential oil from sandalwood is extracted through the steam distillation process. Major chemical constituents of essential oil extracted from this plant are different types sesquiterpene alcohols such as bergamotols, β- and α-santalols, along their quite a lot of stereoisomers; minor compounds are bisabolol, nuciferal, lanceol, and sesquiterpene hydrocarbons like bergamotenes, β-bisabolene, β- and α-santalenes, and γ-, β-, and α-curcumenes, and phenylpropanoids ( Jones et al., 2006). According to few critical studies, major component of essential oils extracted from this plant are trans-bergamotol, cis-β-santalol, α-sesquiterpene alcohols, cis-α-santalol; minor compounds are hydrocarbon santene, α-santalene, β-santalene, α-bisabolol, β-bisabolene, α-curcumene, epi-β-santalene, α-bergamotene, γ-curcumene, β-curcumene, trans-β-santalol, cis-lanceol, and heterocyclics (Braun et al., 2003; Jones et al., 2006; Bhattacharya, 2016). Other chemical constituents are teresantalol, santenol, alcohol, ketones, nor-tricycloekasantalal, isovaleraldehyde, aldehydes, 1-santenone, and santalone and the percentage of α and β santalol in sandalwood essential oil is 19.6% and 16.0%, respectively (Kumar et al., 2015). Sandalwood tree is used for its wood and timber. Wood is used as fuel but it is very expensive to use it in this way. The oil extracted from the heartwood which is yellow in color with a pleasant smell is utilized in cosmetics, perfumery, aromatherapy, and pharmaceutical industries. This oil act as a base for most of the Indian attars, it is also used as a food flavoring agent in many desserts, baked foods, candy, etc. The bark contains 12%–14% of tannin it is used in tannin industries. The leaves of sandalwood trees are eaten by herbivorous animals. It is also used in the treatment of a handful of diseases. This oil is used for the treatment of dysentery, tension, gastric irritability, and as a stimulant for liver, heart, fever, anti-poison, stomach, and improvement of memory (Choudhary and Chaudhary, 2021). Besides perfumery and cosmetics industries Santalum album has various pharmacological applications. Sandalwood oil has many biological effects from antibacterial to an anticancer agent. Sandalwood oil has a sedative effect on nerves so it is used in nervous tension, insomnia, and headaches. It is reported that chemical constituent santalol have a central nervous system (CNS) depressant effect for which it is used in patients who have sleeping disorders. It is reported that the most important chemical constituent of the sandalwood oil α-santalol have a great effect on tyrosine and cholinesterase in vitro so it is useful for the management of Alzheimer’s disease and also in skincare (Misra and Dey, 2013; Ohmori et al., 2007). East Indian sandalwood oil has antibacterial properties. Gram-negative bacteria Helicobacter pylori which cause gastric, duodenal and stomach ulcers, β- and α-santalol compounds of sandalwood oil is effective in these bacterial diseases. This oil show antidermatophytic properties against

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Trycophyto rubrum, Microsporum canis, and Trichophyton mentagraphytes. Sandalwood essential oil constituents such as α- and β-santalol is effective against Staphylococcus, epi-β-santalene, and Salmonella typhimurium is effective against Salmonella typhimurium, santalbic acid which is a chemical constituent of seeds is effectual against few of the pathogenic fungi and gram-positive bacteria, respectively (Pullaiah et al., 2021). Sandalwood essential oil is effective against various fungi including Microsparmum canis, Trichophyton rubrum, and Trichophyton mentagrophytes. Sandalwood essential oil also has antiviral properties, it is used for the cure of blemishes of skin, warts, skin tumors of viral origin and it is effective against Herpes Simplex Viruses-1 and -2 too (Moy and Levenson, 2017). The anti-cancer effect of sandalwood essential oil is seen in skin carcinogenesis results from the induction of ultraviolet-B in SKH-1 mice along with in vitro melanoma models, prostate and breast cancer, and skin carcinogenesis induced by chemical means in SENCAR, and CD-1 mice (Santha and Dwivedi, 2015). The essential oil also has the property of repellant; it is repellant against Varroa jacobsoni in the colonies of honey bee, Lycoriella mali and also against spider mites Tetranychus urticae (Roh et al., 2012; Roh et al., 2011). For its fragrance sandalwood essential oil is used in aromatherapy. This oil is also used in chronic bronchitis, respiratory tract infections and as an anti-inflammatory agent, antipyretic agent; it has also metabolic effects, physiological effects, genotoxicity effect, genitourinary system effect, etc. (Kumar et al., 2015).

6.2.2 Santalum spicatum (Western Australian sandalwood) Santalum spicatum is a hemiparasitic small tree or shrub belonging to the family Santalaceae which takes 50–90 years to mature and attains a height up to 3–8 m. This tree is comparatively shorter than Santalum album. Flowers come into sight from the month of December to the end of January and their fruit matures from early June to September. As Santalum spicatum is a hemiparasitic plant it depends on the host for essential nutrients. The haustoria of sandalwood trees are protruding out from the root and attach to the roots of the hosts. Various species of genera Acacia and Eremophila are the hosts of Santalum spicatum. Some of them are Acacia acuminata, Acacia aneura, Acacia collectioides, Acacia hemiteles, Acacia linophylla, Acacia tetragonophylla, Cassia chatelainiana, Cassia nemophila, Casuarina cristata, Dodonaea lobulata, Eremophila alterinifolia, Eremophila dempesteri, Eremophila oldfieldii, Eremophila ionantha, Eremophila aldfieldii, Eremophila oppositifolia, Eucalyptus loxophleba, and Eucalyptus wandoo. S. spicatum is distributed throughout the semi-arid climatic regions of South-Western Australia in the states of Western Australia. It covers an area of 161 million hectares (Chapman, 2015). Australian sandalwood tree is reported from the semi-arid and arid areas of the state of Western Australia. Rainfall has a marked effect on the growth rate and regeneration of the tree. It requires 200 and 600 mm rainfall annually for its superior growth. Astonishingly it takes 100 years to mature where annual rainfall is close to 300 mm and takes only 23 years to mature where annual rainfall is 500 mm (Herawan et al., 2014). Santalum spicatum generally grows well in red soil and the pH of the soil may be neutral or slightly acidic. Sandalwood tree grows well in lighter soil like loams and sandy loams with granite components. Potassium present in granite soils serves as nutrition for sandalwood trees. The first essential oil from Santalum spicatum was exploited in 1920. Further analysis confirmed the major chemical constituents of sandalwood essential oil – 2(E), 6(E)-farnesol, epi-αbisabolol, (Z)-α-santalol, (Z)-β-santalol. Santalum spicatum is commercially less important

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than Santalum album due to the quantity and quality of essential oil extracted from it. Apart from that, it contains less amount of santalol and E,E-farnesol which is a suspected allergen and is present in very high quantity in Santalum spicatum. Almost 100 different types of sesquiterpenes are found in the heartwood extract of Santalum spicatum which protect the innermost wood from the fungal pathogens responsible for wood-rotting (Moniodis et al., 2017). The wood and oil of Santalum spicatum is used for the manufacture of joss sticks and ornamental wood carvings. The essential oil of Santalum spicatum is utilized in the cosmetics, perfumes, and sacred unguents. The essential oil is used as a disinfectant for the urinary tract in which infection is caused by a gram-positive bacteria Staphylococcus aureus. QN50, which is a sesquiterpene alcohol found in the Santalum spicatum extract is effective against two larvae of two mosquito species, Culex moestus and Aedes camptorhynchus (Spafford et al., 2007).

6.2.3 Santalum paniculatum (Hawaiian sandalwood) Santalum paniculatum belonging to the family Santalaceae, a hemiparasitic, evergreen tree, or shrub endemic to the Hawaii islands and also known as “The Big Island”. It attains a height up to 3–10 m, leaves are greenish blue, oval-shaped; the flower is green-whitish and fruit is black or purple when matured having a single seed. Well drained neutral or slightly alkaline soil is suitable for its growth (Merlin et al., 2006). Sandalwood trees have a high tolerance to drought and poorly grow in shady places. As it is a hemiparasitic plant it depends on one or more hosts for nutrition. It is a slow-growing plant, grows 30–70 cm in a year but its growth is faster in fertile soil. The chief chemical compounds of the essential oil are (Z)-β-santalol (11%–17%) and (Z)-α-santalol (34%–41%). Some other chemical constituents present in the Satalum paniculatum are (Z)-trans-α-bergamotol, (Z)-γ-curcumen-12-ol, (Z)-lanceol, (Z)-β-curcumen-12-ol, (Z)-nuciferol, (E)-α-santalol, spirosantalol, and epi-β-santalol (Braun et al., 2014). The essential oil of Santalum paniculatum is highly valuable which is used in perfumery, cosmetics, incense sticks, and aromatherapy. Wood is also used in arts, handicrafts, carving, and also for decorative furniture. Powdered heartwood mixed with other plants and laxatives can be used for venereal diseases in males and females. For treating severe sores powdered form of heartwood is mixed with other plants; powdered heartwood is also used for treating dandruff and head lice (Sundharamoorthy et al., 2018).

6.2.4 Santalum yasi The oil yielding capacity of Santalum yasi was reported from Fiji in the first decade of the 19th century. This plant is a hemiparasitic, small tree attaining a maximum height up to 8–12 m (Thomson, 2006). The bark is greyish-brown colored, leaves of this plant is simple, opposite, and lanceolate; the flowers are monoecious, clustered, small and aggregated in panicles in the leaf axils; fruit is drupe and single-seeded (Huish, 2009). Santalum yasi required 125–175 cm of rainfall annually. As it is a hemiparasitic plant it is associated with one or more than one host species such as Cocos nucifera, Casuarina sp., Callophyllum sp., Storckiella vitensis, Hibiscus tiliaceus, Fagraea gracilipes, Acacia sp., it also intercropped in the company of Pinus caribaea in Tonga and Fiji (Thomson, 2006). It grows in well-drained, acidic, or alkaline soils and also grows in shallow and infertile soil and distributed dominantly in Fiji, Tonga, and Niue (Doran et al., 2005). Essential oil of Santalum yasi is extracted from the yellowish-brown,

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heartwood having a pleasant smell. The major chemical constituents are (Z)-β-santalol, (Z)-αsantalol, and minor chemical compounds are, (E)-epi-β-santalol, α-santalene, (Z)-β-santalol, (Z)-α-santalol, and (Bush et al., 2020a, b). Santalum yasi play a noteworthy role in the artistic customs of Tonga and Fiji. It is recognized as “ahi” in Tonga but “yasi” in Fiji. In Tonga, yasi heartwood is very important at weddings and funerals. The wood obtained from Yasi can be used as a fuel, carving, and building material in Fiji. The oil obtained from the Santalum yasi is utilized in the perfumery, cosmetics and incense and religious ceremonies. The grated wood is mixed with the heartwood is valuable so it is rarely used as timber (Huish, 2009).

6.2.5 Santalum austrocaledonicum Santalum austrocaledonicum is a conspicuous, hemiparasitic shrub or tree, belonging to family Santalaceae, native to New Caledonia and Vanuatu. It attains a height up to 5–12 m and 40–50 cm in diameter. The bark is greyish and rough; leaves are simple, opposite, entire, glabrous, dark green/shiny; inflorescence is terminal and axillary panicles; flowers are bisexual, small, white to cream through the maturity; fruit is drupe and single-seeded. It grows well in well-drained acidic or slightly alkaline soils. It needs a rainfall of 800–2500 cm per year and grows at an altitude of 500–800 m (Tate and Page, 2018). Santalum austrocaledonicum naturally occurred in New Caledonia and Vanuatu in earlier times. Espiritu santo, Aneityum, Erromango, Efate, Futuna, Aniwa, Malekula, and Tanna are some of the islands in Vanuatu where Santalum austrocaledonicum occurs naturally. In New Caledonia, Var. austrocaledonicum is found in the Isle of pinus and is less common on Grand Terre the main island, Var. pilosulum is common in near Noumea and low elevations of Grand Terre, Var. minutum is found in North-West of Grand Terre and Var. glabrum is found on Loyalty Island. Santalum austrocaledonicum is not planted outside the natural range (Bottin et al., 2005). Santalum austrocaledonicum is valuable for its oil extracted from the heartwood. The percentage of essential oil concentration is different in different cross-section. The major chemical constituents are (Z)-β-curcumen-12-ol, β-santalol, cis-nuciferol and α-santalol. In individual trees of a population, the commercially important chemical constituent α- and β-santalol are present in 0.8%–47% and 0%–24.1%, respectively (Page et al., 2010). Santalum austrocaledonicum was exploited in the mid-1800s and it is used from then up until now. The wood from sandalwood is utilized for making coffins, carvings, valuable handicrafts, prayer poles, joss sticks, other religious artifacts, and fuel for funeral pyres. The oil extracted from heartwood is used to treat fungal and bacterial infections and it has anti-inflammation properties related to sunburn and joint and muscle pain. It has a sedative effect, helps in relaxing anxiety, sleeping disorders, and promoting relaxation. It has also the properties of coolant, astringnes, erysipelas, antipyretic, and is used to treat migraines, gonorrhea, and cystitis. It is also used in the cosmetic, perfumery, aromatherapy, and soap industries.

6.2.6 Santalum lanceolatum Santalum lanceolatum belonging to the Santalaceae family, is a hemiparasitic, evergreen, small tree or shrub that depends on other hosts for nutrition. It achieves a maximum height

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up to 9 m. Leaves are brown and glabrous; flowers are green, cream-white and blooms in January and October; fruit is a drupe. It grows well in semi-shade or no shade and moist soil (Harbaugh and Baldwin, 2007). This plant is dispersed through temperate regions of south, the rid center to the tropical north of Australia. In these different geographic regions, the characters like leaf shape, color, and size also changes. In the mid-19th century, it is planted in Victoria, New South Wales, and Northern Queensland (Harbaugh, 2007). Santalum lanceolatum wood is used for making joss-sticks, carvings, etc., in Taiwan and China; the burnt leaves can also be used as a repellant to insects.

6.2.7 Santalum macgregorii Santalum macgregorii belonging to Santalaceae family is a hemiparasitic, 7–21-m-high multistemmed with open crowns, crooked and short boles. It requires rainfall of about 1000 mm annually. The bark is rough, moderately tessellated; leaves are light green, opposite, lanceolate (Page et al., 2020). These species grow well in well-drained areas, soil-like pure sand to dappled clay loams having calcrete modules prefer for its growth. It grows at an altitude of 750 m near sea level (Brophy et al., 2009). Santalum macgregorii is endemic in Papua New Guinea (PNG) in savannah woodlands and grasslands. This PNG sandalwood is commercially exploited in the late 1800s. This species is commercially important for its essential oil obtained from the heartwood of the tree. The value of oil depends upon the oil chemical constituents, quality, and quantity of heartwood. The main chemical constituents are (Z)-β-curcumen-12-ol, (Z)-β-santalol, (E,E)-farnesol, (Z)-α-santalol, (Z)-γ-curcumen-12-ol, (Z)-lanceol (Z)-nuciferol (Brophy et al., 2009). The wood of Santalum macgregorii is used for carving and burned as incense. The essential oil yield from its heartwood is used in perfumery, cosmetic, and aromatherapy industries. The oil has a pleasant smell. With the increasing population, the demand for sandalwood essential oil is also rising every day, as it has massive use in our daily life. So it is very necessary to a plantation of sandalwood tree and also modification of conventional extraction method so that we can extract a large amount of essential oil in a lesser period of time. For this more research on the various species of the sandalwood tree is absolutely necessary.

6.3 Methods of extraction of sandalwood essential oil Some of the widely utilized methods of extraction of essential oils are CO2 extraction, steam distillation, hydrodistillation, superficial fluid, liquid extraction, and solvent extraction (Kusuma and Mahfud, 2016). Among these, the most reliable extraction method for sandalwood essential oil is the steam distillation method. In this method, the sample obtained from plant material is boiled in aqueous solvent and heated using steam. This heat is functional to burst and for breaking of cell structure so that the essential oil is released. The temperature is sufficient to break the cell structure. A total of 93% essential oil can be extracted by the application of the steam distillation method. Other extraction methods can be efficiently used for the extraction of the rest of the 7% of essential oil.

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Another alternative technique employed to obtain essential oil from sandalwood is the solvent extraction technique (Zhang et al., 2012). In this method, different types of solvents are used to perform the extraction process that primarily includes acetone, hexane, methanol, petroleum ether, and ethanol. Here, the plant material is grinded thoroughly with the aqueous solvent and heated to obtain the essential oil, which is followed by the process of filtration and the filtrate is accumulated through the solvent evaporation technique. After that, the remaining filtrate along with pure ethanol is mixed to extract the essential oil at a low temperature by distillation. The aroma is absorbed by the ethanol and following the vanishing of the alcohol, the aromatic portion of the essential oil is remained (Nautiyal, 2010). These conventional methods take quite a long duration of time to complete the entire oil yielding procedure. To augment the acquiesce of essential oil, researchers have applied various manipulations to the core technique that includes high pressured distillation, which results in a relatively shorter distillation process. But the end product lacks quality when compared to traditional techniques. This is because the raise in pressure is always supported by an higher temperature. This sudden increase in temperature can cause denaturation of oil components, for which essential oil extracted by this method has less fragrance. Therefore a new “green method” is lately becoming very popular essential oil extraction by using microwave technology. By using this method, the pure essential oil can be extracted using fewer amounts of solvent and in a limited time (Kusuma and Mahfud, 2018). There are three primary elements in this method—a compressor for pushing air into the matrix containing distiller, condenser and a microwave. Airflow is added in the microwave-air-hydrodistillation for obtaining a better quality sandalwood essential oil. As sandalwood essential oil components are heavy and it is difficult to extract, there is always a scope for improvement in various oil extraction methods and as a result, we get these kinds of equipment. Interestingly, a domestic microwave oven is converted for microwave-assisted hydrodistillation operation in this method, and then the sandalwood plant samples were kept in a flask that contains deionized water; it is then placed into the cavity of microwave oven. A condenser is employed at the apex to collect the sandalwood essential oils. To remove the water the essential oils are dried over anhydrous sodium sulfate.

6.4 Therapeutic benefits of sandalwood essential oil The therapeutic benefits of Santalum album essential oil can be credited to its properties as an sedative, carminative, emollient, anti-inflammatory, antiseptic, astringent, diuretic, disinfectant, expectorant, memory booster, antiphlogistic, hypotensive, antispasmodic, and tonic compounds (Shetteppanavar, 2017). The utilization of naturally occurring substances has been encouraged due to their less noxious behavior and capability to transform various signaling pathways involving in the growth of multiple disorders. The phytochemical α-santalol, extracted from sandalwood oil has been potentially utilized for its anticancer, antifungal properties, anti-hyperglycemic, anti-inflammatory nature (Nakatsuka et al., 2016). The inflammation resistant nature of α-santalol is a frequently considered character. Various studies revealed the capability of α-santalol to change the proclamation of chemokines and cytokines, specifically in skin tissue samples (Sharma et al., 2014). The study

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revealed that treatment with Santalum album essential oil can suppress lipopolysaccharidestimulated proclamation of cytokines and chemokines. Generally, the anti-inflammatory nature of α-santalol indicates that they can be utilized to develop anti-inflammatory medicines. A study has been conducted to analyze the significance of Sandalwood oil on the declining inflammatory and thriving nature of psoriasis, keratinocyte hyper-proliferation causing inflammatory plaques. The observation contrasted both in vitro psoriatic skin tissue samples and typical skin tissue and resulted in noncarcinogenic reaction otherwise prominent on typical skin. In the psoriatic skin models, a distinct decline in the proclamation of major inflammatory factors was expressed in inclusion to declined propagation via histological monitoring. In another report, five batches of mice were randomized into diverse dietary clusters distinguished by the enactment of several ordinary oils that were contrasted to Sandalwood oil, a natural reservoir of α-santalol. The report revealed that more than 9% Sandalwood oil in soybean oil as a nutritional inclusion for 8 weeks transformed into an increase in the total polyunsaturated fatty acids (n-3) and a declined ratio of n-6:n-3 polyunsaturated fatty acids in liver and adipose tissues (Li et al., 2013). Polymeric forms of unsaturated acids, specifically n-3 including docosahexaenoic acid and eicosapentaenoic acid that antagonizes the influence of n-6 was found to be nearly correlated with declining heart related infection and danger, along with anti-inflammatory properties. Li et al. (2013) studied through correspondence involving n-6:n-3 ratios in plasma concentrations and rat livers that n-6 is nearly connected to the proclamation of pro-inflammatory cytokines like leukotrienes and prostaglandins. Contrarily, the acids of n-3 types were correlated to the declining cytokines expression and antiinflammatory operations. This evaluation revealed that Sandalwood oil, a natural reservoir for α-santalol, can be correlated to anti-inflammatory action. The antihyperglycemic nature of α-santalol is already a global sensation. In a study of α-santalol, Sandalwood oil, glibenclamide, an antihyperglycemic mediator, which was intraperitoneally organized to rats with chemically incited diabetes. The mice enduring α-santalol and Sandalwood oil proclaimed an enhanced bodyweight, declined intake of water content, enhanced liver protein, liver glycogen and liver weight. Level of blood glucose were crucially declined, these results were significantly differentiable from glibenclamide associated results. The report also revealed that oxidative stress induced rats because the D-galactose administration had enhanced impact when Sandalwood oil and α-santalol were administered. The conclusions were alike to the conclusion of α-tocopherol. The evaluation also proclaimed that some of the useful impute of α-santalol was increased by other constituents of Sandalwood oil (Misra and Dey, 2013). These evaluations proclaimed the probable antihyperlipidemic and antihyperglycemic nature of Sandalwood oil (Bommaredy et al., 2017; Kaur et al., 2005). Several reports have exposed that α-santalol has neuroleptic characteristics. The nerve related impacts of Sandalwood oil and its components in model organisms (mice) indicated through intraperitoneal inoculation that both α-santalol and β-santalol were made accountable for the nervous system associated effects related to Sandalwood oil. These components enhanced the quantity of the metabolites of homovanillic acid, amines, 5-hydroxy indole acetic acid, and/or 3,4-dihydroxy phenylacetic acid in the brain carrying an alike action although to a minor proportion as compared to chlorpromazine (Okugawa et al., 1995). α-Santalol was furthermore proclaimed to be a serotonin 5-HT2A and a dopamine D2 and receptor antagonist, reporting an reverse psychotic activity with an alike but dull action distinguished to chlorpromazine (Okugawa et al., 2000). Another animal evaluation monitored

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the activity of α-santalol on rats which were intentionally made sleep-deprived. Breathing of the substance resulted in a crucial decline in awaken time of the rats enhanced eye movement of nonrapid nature during sleep. No crucial differentiation in the activity of α-santalol upon hindrance of the olfactory organization was noticed; indicating α-santalol manifests its activity by the circulatory system. Sandalwood essential oil possessed anti-ulcer and antiinflammatory actions as indicated by its potential inhibition in the carrageenan influenced paw edema, pylorus ligation influenced ulcer, along cotton pellet influenced granuloma (Dulal et al., 2019). Sandalwood essential oil restores and rejuvenation of skin ageing and wrinkles skin by its antioxidant properties (Misra and Dey, 2012). Evaluation of scavenging activity of NO ( Jagetia and Baliga, 2004), metabolic property (Chhabra and Rao, 1993; Dulal et al., 2019), cell regulatory property, and anti-inflammatory property. Utilizing to the skin, Santalum album L. oil is cooling, soothing, moisturizing, and generally applied for desiccated skin surroundings caused by skin inflammations and moisture loss. Sandalwood oil can be utilized to mitigate psoriasis, eczema, and for the medicament of acne and oily skin (Chhabra and Rao, 1993). It mitigates inflammation and itching of the skin, also has a significant toning action and is utilized with potential results in oily skin state by preventing the skin from forming ugly scars and for confronting dry eczema (Dulal et al., 2019).

6.5 Production and composition of sandalwood essential oil According to Thomson (2020), for thousands of years, sandalwood has been greatly revered in Asian religions and cultures and predominantly in eastern parts of Indonesia and southern parts of India. From early 19th century, the traders from Europe were exploiting the precious sandalwood belongings of the Pacific for the exasperate in the Confucian, Buddhist, and many spiritual temples of Chinese origin. In 1865, the period of traffic had nearly come to an end due to the overuse of the sandalwood resources commercially throughout the Pacific (Merlin and Fleetham, 2013). The quantity and quality of smallholder sandalwood production greatly influenced and guided the Pacific Island sandalwood growers (Page et al., 2012). Ananthapadmanabha (2000) reported that the Santalum album is designated as the jewel amid the species bearing best valued essential oil demanded by the international and domestic industries. Indonesia and India are the main exporters and producers of sandalwood (Santalum album) essential oil. Annually several hundreds of tons of world production are required for the world’s population. France and United states are the two leading importers sandalwood oils from India. Indonesia represents the biggest export market for sandalwood oil to the United States. In India, approximately 85% of sandalwood and sandalwood oil is produced for the world demand, whereas the production rate of Indonesia and additional sources like New Caledonia and Fiji are about 5% and 10%, respectively (Gowda et al., 2006). A major report revealed that in Maharashtra, Tamil Nadu, Madhya Pradesh, Rajasthan, Gujarat, Assam, and Andhra Pradesh, many state subsidized farmers and industrialists are planting Indian sandalwood on a large commercial scale of some approx. 5000 ha (Rao et al., 2016). A sum of 100–400 tons of Indian sandalwood is harvested annually and about 80,000 kg

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of sandalwood oil is produced annually by the domestic industries (Nautiyal, 2019). Looking at the Global demand India produces approx. 5000–6000 tons of sandalwood and approx. 100–120 tons of sandalwood oil per annum. Santalum spicatum syn. or Eucarya spicata is the native species of South West Australia near Perth which prefer desert-like areas. In the northern part of Western Australia principally in Queensland, another species, S. lanceolatum is also found which is commercially less exploited than S. spicatum (Nautiyal, 2019). Shankaranarayana and Parthasarathi (1984) reported that the production rate of Australian sandalwood oil per annum is approx. 30 tons. For the protection of sandalwood trees from extinction, restrictions have been made compulsory in several countries. Santalum ellipticum Gaudich. (‘iliahi alo’e) and S. paniculatum Hook. & Arn. (iliahi) are naturally occurred in Hawaii (Thomson, 2020) and around 7000 ha are managed by sustainable management. Santalum yasi is native to Fiji and Tonga, bearing high valued sandalwood which is frequently similar to S. album sandalwood oil quality but this species becomes vulnerable quickly due to the overuse at the beginning of the 1800s. Therefore, S. yasi is conserved under sustainable management studies. The exportation rate of S. yasi is less than 100 ADTH (Air-Dry Tones Heartwood) from Fiji and Tonga. According to Harbaugh and Baldwin (2007), the two species S. yasi and S. album although having hefty geographic distributions, but are believed to have arisen from a common ancestor in Northern Australia about 3 million years ago. In Fiji and Tonga, when these two species are grown together and they can naturally hybridize with each other. Successful implementation of the sandalwood Development Project of the Ministry of Forestry results in a large increasing scale the plantation of S. album and S. yasi and their hybrids are produced in Fiji and the last 5 years, there has been seen largely increased planting in Tonga (Bolatolu et al., 2019). Santalum austrocaledonicum Viell is naturally distributed throughout the Vanuatu and New Caledonia. The primary means of income generation is managed through the exploitation of sandalwood in many villages of Vanuatu and it also provides both urban and rural employment. In the 1980s the initial export industry was commencing in Vanuatu and continued to become the major export country for many islands (Page et al., 2010). The hybridization of the further distantly connected species S. austrocaledonicum and S. album was done in Mangaia, the Cook Island and also hybridization of S. austrocaledonicum and S. lanceolatum species were performed successfully. Over the last decade, the Pacific Nations supply approx. 270 tons of sandalwood per annum which is equivalent to 10% of the quantity produced in the first half of the 19th century that means the production rate has fluctuated (Thomson, 2020). Sandalwood and its oil had an ancient history of use for over 4000 years as mentioned in the Sanskrit manuscript. The composition of sandalwood essential oils shows variation from one species to another. The alcohols like cis-β-santalol and cis-α-santalol and their overall concentration mainly depict the quality of sandalwood oil. Many standard documents reported that 90% of the total volatile compounds of the sandalwood are the composition of these two compounds (Melanie et al., 2004). More than 100 constituents are found on sandalwood oil. Approx. 7%–60% of total santalols are comprised of α-santalol, and approx. 7%–33% santalols are comprised of β-santalol, and they are responsible for the fragrance. Other minor components like sesquiterpene hydrocarbons (60%) are also present which are more often than not β-santalene and α-santalene, with a little amount of α- and β-curcumene, α-bisabolol, epi-βsantalene, and β-bisabolene (Braun et al., 2003). Some other components found are

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TABLE 6.1 Table showing species wise santalol content of sandalwood. Species name

Origin

Oil content (%)

Santalol content (%)

Santalum album

India, Indonesia

6–7

α-santalol: 41–55 β-santalol: 16–24

Santalum spicatum

Western Australia

2

α-santalol: 15–25 β-santalol: 5–20

Santalum yasi

Fiji

5

α-santalol: 37–39 β-santalol: 26–28

Santalum austrocaledonicum

Vanuatu, New Caledonia

3–5

α-santalol: 48–49 β-santalol: 20–22

From AAG (Australian Agribusiness Group), 2006. Marker Overview—The Australian Sandalwood Industry. Independent Assessment, Australian Agribusiness Group, Melbourne, Australia. 4 p. http:// sandalwood.org.au/wp-content/uploads/2012/06/AAG-2007-Market-Overview.pdf; Nautiyal, O.H., 2019. Sandalwood (Santalum album) oil. In Fruit Oils: Chemistry and Functionality. Springer, Cham, 711–740.

tricycloekasantalal, santene, teresantol, bomeol, santalone, teresantalic acid, and dihydro-βagarofuran. Recently, a novel aromatic ester and three new neoligans have been isolated from the heartwood of S. album by Kim et al. (2005). The quantity of α-santalol (45%) is more profuse than β-santalol (21%) in sandalwood oil. The β-santalol and α-santalol contain amazing fragrance quality and in this 2-furfuryl pyrrole may also have a say. Several factors can influence the quality and concentration of heartwood oil in sandalwoods such as genetic factors, environmental factors, and agro-climatic factors and it also varies from species to species (Doran et al., 2005). The santanol content of various Sandalwood trees is presented in Table 6.1. The highest proportion of oil content or santalol is acquired by the heartwood of S. album or Indian sandalwood species (up to 8%) compared with other commercially important sandalwood tress (Baldovini et al., 2011). The total santalol contents of Indian sandalwood (S. album) are 46.6–59.9 for β-santalol and 24.6–29.0 for α-santalol and in China (S. album) the proportion of β-santalol is 14.6 and α-santalol is 7.3 and also in Indonesia (S. album) the santalol content ranges from 7.1 to 48.6 for β-santalol and 8.7 to 25.2 for α-santalol. The chemical component of Indian sandalwood oil and Chinese sandalwood oil found almost similar in quality. Sesquiterpene alcohols like epi-β-santalene, β-santalol, epi-β-santalol, α-santalol, trans-αbergamotol, trans-α-bergamotene, α-santalene, and β-santalene are found in the heartwood of S. album (Chen et al., 2011). Approx. 85% of the total santalols are extracted from S. album, sandalwood species and for this reason, it is considered as the main demandable and wanted sandalwood in the global market. The Australian sandalwood species S. spicatum, produces only 2% oil content and 40% of total santalol. Therefore, this species is regarded as the least valuable sandalwood species in the commercial field (Brand et al., 2007). With the increasing height of the trees, the extracted oil quantity of S. spicatum is decreased. The major components found in S. spicatum essential oils are E,E-farnesol, α- and β-santalol, α-bisabolol, along with some olefin constituents including dendrolasin, sesquisabinene, santalenes, and sesquiphellandrene (Chen et al.,

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2011). Moretta (2001) reported that the natural distribution of this species also results in variation in the oil component. The higher percentage of E,E-farnesol and this variation leading to the inferior price of S. spicatum essential oil (Moniodis et al., 2015). Sandalwood from New Caledonia and Vanuatu (S. autrocaledonium) and Fiji (S. yasi) of Pacific Islands are almost similar in quality to Indian sandalwood. The Fiji sandalwood produces approx. 5% of essential oil content and α- and β-santalol contents are 37%–39% and 26%–28%, respectively. However, the S. autrocaledonium, produces approx. 3%–5% essential oil content and α- and β-santalol contents are 48%–49% and 20%–22%, respectively, as reported by the AAG (Australian Agribusiness Group) (2006). Some other minor compounds reported in some species of S. yasi, are (Z)-nuciferol, (E)-epi-β-santalal, (Z)-lanceol, α-santalene, (Z)-β-santalal, (E)-β-santalol, (E,E)-farnesol, and (Z)-α-santalal is found in significant levels (Bush et al., 2020a, 2020b). In the species S. autrocaledonium, besides α- and β-santalol two other key components are found viz., cis-nuciferol and (Z)-β-curcumen-12-ol extracted from the sandalwood heartwood. Surprisingly only 1% of oil content is produced by the species S. lanceolatum (Rao et al., 2016). In general, plants are enriched with phytochemicals constituents, which they generate for their protection. Santalum album L. is the source of natural scent with commercial and medicinal potential. Sandalwood oil is assembled in the heartwood after more than three decades of its development in a normal environment (Melanie et al., 2004). Sandalwood oil is being utilized globally majorly for the cosmetics, essential oil, and aromatherapy industries (Bisht and Kumar, 2021). The significance of Sandalwood oil depends on its quality. The quality and potential significance of sandalwood oil is because of the presence of Z-β-santalol, Z-α-santalol, and other phytochemical compounds (Bisht et al., 2020; Kumar et al., 2015). Phytochemical evaluation of various parts of Santalum album L. i.e., bark, seed, leaf, fruit, root, and heartwood expressed the attendance of fatty acids, amino acids, sesquiterpene alcohols, terpenoids (Zhang et al., 2012), flavonoids (Yan et al., 2013), tannins (Shankaranarayana et al., 1980), aldehydes, esters, and vitamin E. The seed of the Sandalwood tree majorly consists of polyunsaturated fatty oil, which is constituted of stearolic acid, oleic acid, palmitic acid, and ximenynic acid (Bisht and Kumar, 2021). Fruit pericarp of sandalwood tree contains various constituents viz., oleic acid, esters, palmitic acid, aldehydes, vitamin E, squalene, stigmasterol, fucosterol, sesquiterpenoids, cedrol, santalol, alkanes, heterocyclic compounds, ketones, alcohol, betulinic acid, phenylalanine, leucine, essential amino acids, glycine, glutamic acid, etc. (Bisht and Kumar, 2021). Sandalwood bark comprised mainly fatty acids, tannins, and less quantity of β-sitosterol. Also, several flavonoids such as isovitexin, vitexin, isoorientin, orientin, and isorhamnetin were extracted from the leaves of Sandalwood. Diagrammatic representation of important phytochemicals in the essential oils was presented in Fig. 6.1. Krishnakumar and Parthiban (2017) had extracted Sandalwood essential oil from the three wood samples, which was evaluated by gas chromatography-mass spectrometry. Several phytochemical constituents were isolated in oil identified from the heartwood, root wood, and sapwood samples. Among the several isolated phytochemical substances, α-santalol is found to be of the highest percentage. Based on the three samples of sandalwood oil, heartwood oil yields higher β-santalol followed by α-santalol in root wood oil and very less amount of β-santalol and α-santalol present in the sapwood oil. The percentage of several isolated phytochemicals were quantified, in heartwood oil and root wood oil, respectively, viz.,

6.6 Safety, toxicity, and regulation of sandalwood essential oil

Cislanceol Trans - β Santalol E-Nuciferol

p-Benzoquinon 0 TereSantatol 10 20 Epi- β-Santalene 30 40 β-Santalene 50 60

β-Santalol

λ-Carene

E-cis, epi- β Santalol

135

Percent composition of Heart Wood Percent composition of Root Wood Percent composition of Sap Wood

α-Santalol

α-Curcumene α-Santalene

Z- α-transBergamotol

FIG. 6.1 Diagrammatic representation of important phytochemicals in the essential oil identified from the wood extracts of Santalum album using GC-MS analysis.

p-Benzoquinone (0.17%, 0.14%), TereSantalol (1.17%, 1.19), β-Santalene (1.87%, 1.89%), α-Curcumene (0.41%, 0.40%), Z-α-trans-Bergamotol (2.06%, 2.15%), E-cis,epi-β-santalol (7.26%, 6.23%), β-santalol (27.01%, 27.40%), E-Nuciferol (1.63%, 0.83%), α-Santalene (0.86%, 1.21%), epi-β-Santalene (1.02%, 1.28%), λ-Carene (0.36%, 0.42%), α-Santalol (54.28%, 55.16%), Cislanceol (0.89%, 1.08%), and trans-β-santalol (1.02%, 0.64%). The identities of phytochemical constituents were also confirmed by 13-Carbon-nuclear magnetic resonance (Asili et al., 2009). This technique is significant for analysis of essential oils, specifically in the isolation of compounds that are poorly separated by gas chromatography-mass spectrometry (Cavaleiro et al., 2002). Hasegawa et al. (2011) investigated the several chemical constituents and secondary metabolites, of the sandalwood tree, which were isolated by nuclear magnetic resonance (NMR) spectroscopic as (Z)-santalals; (E)-santalals; and santalyl formats. The formerly unidentified santalyl formats were evaluated as the latest constituent of Santalum album L. oil. These constituents were characterized and isolated by 1-Hydrogen- and 13-Carbon NMR spectroscopy. Phytomedicinal investigations have led to the evaluation and characterization of medicinally significant secondary metabolites from sandalwood oil. Although, there are many probabilities of finding novel phytochemicals. Pharmacological evaluations have validated the ethnomedicinal practices and helped in isolation of many novel therapeutically significant phytochemical compounds from sandalwood trees (Bisht and Kumar, 2021).

6.6 Safety, toxicity, and regulation of sandalwood essential oil Doing an ancient, historical, and oldest type of essential oil, sandalwood possesses powerful and valuable properties and is also being used in aromatherapy hold very high regard in the essential oil industry. The ancient Egyptians used the sandalwood to preserve bodies. For 4000 years, sandalwood was being used for aromatic and perfumery purposes. Sandalwood was used to build up ancient Indian temples to keep the white ants at bay and also have used in Indian meditation ceremonies (Nautiyal, 2019). Santalol is the main constituent found in

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the sandalwood essential oil. This oil is utilized as a flavoring component and stimulant in food industries. The United States Food and Drug Administration (FDA), Flavor and Extract Manufacturers Association (FEMA), and Council of Europe (CoE) approve the sandalwood essential oils as a safe aromatic food (Burdock and Carabin, 2008). Various important characters found on sandalwood essential oils are due to the presence of different types of chemical components including the (Z)-β-santalol and (Z)-α-santalol; these are the foremost compounds that are the reason of pleasant fragrance of the sandalwood essential oil and some other compounds like exo- and endo-3,8-dihydro-β-santalols of (E)- and (Z)-forms are responsible for the scent of sandalwood oil (Muratore et al., 2010). Sandalwood oil can also act as a very good fixative. Various medicinal properties are the major characteristics of the sandalwood essential oil such as antioxidant (Misra and Dey, 2013); anticancer activity (Saraswati et al., 2013); antimicrobial ( Jirovetz et al., 2006); antiviral (Paulpandi et al., 2012); and neuroprotection (Mohankumar et al., 2018). The primary compounds β- and α-santalol have the antimicrobial (antibacterial to be precise) property against Helicobacter pyleri and β-santalol showed the antiinfluenza virus activity (Paulpandi et al., 2012). Sandalwood essential oil also acts as a relaxing agent. The main ingredient, α-santalol has the capacity of chemopreventive properties on skin cancer ( Jain and Nair, 2019). The chemical compounds β-santalol holding the important characteristic of quintessential sandalwood aroma. The sedative effect of sandalwood oil is mainly contributed by a combination of both the types (β and α) of santalols (Baldovini et al., 2011). The safety of sandalwood essential oil is a chief required concern among various groups of researchers. While 0.1%–2.4% of allergy cases are found usually from tested peoples who were reported sensitive to the oil, but also few of them did not account for purity and quality of the oil. For example, Santalum paniclatum, the essential oil of Hawaiian sandalwood species or Santalum spicatum, the West Australian species consists of considerable amounts of farnesol—a compound which is recognized as an irritant by the EU Cosmetic Regulation (Moy and Levenson, 2017). But in the species of Santalum album, these irritant chemical compounds are not found. Sandalwood essential oil also can lead to some severe troubles in humans such as blood in urine, vomiting, abdominal pain, itching, nausea, and even injury to the kidney. Therefore, it is recommended to never be taken internally. In female hairless SKH-1 mice the formation of skin tumor was reported to enhance by the α-santalol (Dwivedi et al., 2006). Up to 1992, the sandalwood oil was left out from the NACDG (North American Contact Dermatitis Group) and photopatch allergens group but from then it has been included in this list. Out of 203 female patients, three patients were tested positive in photopatch tests during 7.3 years of evaluation of photosensitivity disorders (Fotiades et al., 1995). Due to the utilization of commercial sandalwood oil, one 53 years old male patient was found positive for photocontact dermatitis which made the scientists highly concerned about the safety of the product (Starke, 1967). In another case, an aged 65, old man was reported with hyperpigmented, erythematous, scaly plague above the temple by the positive patch test with paste obtained from sandalwood (Sharma et al., 1987). A patient, who was 64 years old, was reported positive for sandalwood oil during the screening patch test for pigmented contact dermatitis (Trattner et al., 1999). The suspected fragrance allergy cases among patients were determined through a worldwide multicenter investigation of fragrance contact dermatitis. For a fragrance blend

6.7 Trade and storage stability of sandalwood essential oil

137

containing sandalwood oil, a total of 167 samples were studied at 7 centers and from these tests, more than 6.5% were reported allergic to sandalwood oil. In Japan, from the period of 1990–98 positivity rate of patch testing with sandalwood oil was found to be 0.8% annually. A case study in Korea where 422 patients were subjected to fragrance dermatitis test and out of these 83.4% were women and 23.9% had found previously contacted dermatitis history (An et al., 2005). It was reported that 2.4% of positive responses were produced by sandalwood oil. Although some of the scattered information raises the eyebrow of the world, still due to the limited information found on the carcinogenic properties of sandalwood oil from the study of its safety, it is considered as safe and also for its extensive history of application without much side effects and also labeled as a safe food ingredient (Burdock and Carabin, 2008). Sandalwood essential oil is one of the most valuable types of oil extracted by the steam distillation of the mature desiccated wood. It has several characteristics such as is a faded yellow or yellow fluid with a soft and woody odor and tasted like somewhat vinegary resinous. It is often adulterated with some low-grade costs such as “sandalore,” the synthetic or semisynthetic alternates and effective oils due to its several important properties, a wide range of use and high export demand and step rise in the price (Anonis, 1998). Adulteration of this oil creates severe trouble for oil transporters, regulatory agencies, and is also a serious danger to the wellbeing of the customers. Due to these synthetic additives and substitution of the chemical constitutes along with physical properties of the oil can be changed drastically and can influence the quality of oil and may lead to allergic problems. Castor oil is the most common adulterant and some others like low-grade oil of other sandalwood species and cedarwood oil (Anonis, 1998). The sandalwood essential oil should not contain less than 90% alcohol, i.e., santalol as recommended by various authorities such as US Dispensatory 1955; British Pharmaceutical Codex 1949; Food Chemicals Codex 1981; International Standard, ISO: 3518, 1979. In the United States, the same minimum santalol content is recommended as specified by Essential Oil Association (EOA). Again ISO 3518:2002, gave the standard composition of sandalwood oil (S. album) should not be less than 15%–25% of β-santalol and 40%–55% of α-santalol (Melanie et al., 2004). Lower levels of sandalwood oil, i.e., santalol are considered as low graded quality. The ISO 3518:2002 described certain needs of physiochemical properties and also the chromatographic profile of sandalwood oil to prove its quality. On the basis of the data available for per capita consumption of sandalwood oil, The National Academy of Sciences (NAS) reported data of consumption for the average person is 0.0074 mg/day or 0.0000123 mg/kg/day for an standard person weighing 60 kg. On the other hand expenditure of sandalwood oil is on an average 0.0058 mg/day or 0.0001 mg/kg/day by individual as reported by the Flavor and Extract Manufacturers Association (Lucas et al., 1999).

6.7 Trade and storage stability of sandalwood essential oil From the 5th century BC, the rich tradition of sandalwood trade with the East has found to be started and peaked toward the end of that century. The Indian rulers started the sandalwood trade in India in the early years of 13th century to build the economic strength for power and war through the trading of Indian sandalwood resources such as the powerful Vijaya

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Nagara Empire of Deccan region was the classic historic case reported in this regard (Ganeshaiah et al., 2007). In 1772, Tipu Sultan, the king of Mysore, acknowledged the sandalwood tree as a royal tree by understanding the importance of the tree. With the commencement of Buddhism in Chinese provinces from India, the trade of sandalwood trees was proved to be originated on the basis of some earlier pieces of evidence and also in the first few years of the 19th century the extensive use of the Indian sandalwood in the Pacific was reported (Thomson, 2006). Through the smoldering of sandalwood incense in temples, this type of trade was occurred in the first AD and then extended to the Pacific including Hawaii and Australia. Due to the excessive use of the natural stands and lack of initiatives to regenerate trees, leading to the decrease of natural stocks as the artificial stands increase and this can lead to an increase in market prices (Kumar et al., 2012). A decreasing production rate of sandalwood was reported in India over the last few decades such as 4000 tons in 1950, 2000 tons in 1990, and 1000 tons in 1999 (Ananthapadmanabha, 2000). In Indonesia, during the 1990s the sandalwood trade was rapidly decreased in East Nusa Tenggara Province such that almost 50% in the near the beginning of 1990s to more than 12% in the 1990s and the total production decreasing from 7464 tons during 1987–97 to 2178 tons in the 6 years 2001–07 (Pullaiah et al., 2021). Essential oil is obtained from the heartwood of Indian sandalwood by means of distillation process and on the international market, it trades for over $5000/kg. The wild-harvested Australian sandalwood species has an annual supply nearing 2000 tons of S. spicatum, and at the same time as a 500 m3 license exists for S. lanceolatum. A significant annual compounded growth rate can be seen while comparing the standard auction value for the heartwood of wild sandalwood of Indian origin, which exhibited a significant increase from $9410/ton in 1990 to roughly $155,000/ton in the month of July 2014. For the species S. austrocaledonicum, in Vanuatu, a 12% yearly raise has been recorded in the least salary of the owners of the lands from an equivalent of US$4/kg in 2000 to US$20/kg in 2015 (Da Silva et al., 2016). The export prices of S. spicatum ranged from US $3000 to 11,000/ton in 2007–08 which has improved to US$8000–18,000/ton in 2014–15. It was an excellent indication that showed the cost of S. spicatum varies greatly between grades of product. The Indian sandalwood was able to sell it at 10 times higher price than the Australian sandalwood species due to their higher oil yielding properties with a higher proportion of santalols, i.e., the β- and α-santalol (approx. >90%) which are mainly accountable for the fragrance of sandalwood oil (Baldovini et al., 2011). There is no reliable production data available but Indonesia and India are the two chief growers and exporters of Sandalwood oil which cannot be denied. It is difficult to estimate the domestic consumption of Sandalwood oil, which is certainly high in India and probably greater than the combined total for the rest of the world (Coppen, 1995). The quantity of oil exported during 1924–25 was 85,730 kg. Fetching Rs. 39.90/kg this quantity of export is declined gradually, and in 2005–06, it becomes 5700 kg against the export value of Rs. 913.20 lakhs with several folds of average price increased. The users resort to cheaper alternative substitute oil/synthetics due to sporadic supply, widespread shortage. The substitutes used for S. album oil were Australian, African, West Indian Sandalwood oil, Santalum yasi oil and a host of synthetic Sandalwood aroma chemicals, but none of them can be compared with the fragrance quality of the oil of S. album. The prices of S. album continue to rise as the International demand for this oil cross beyond supply.

6.7 Trade and storage stability of sandalwood essential oil

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In the present day international market, Australia is the largest sandalwood oil producer and the Australian companies including Quintis (former TFS), Santalol and Essentially Australia dominated the market. Due to the huge cultivation and management Santalum album trees in Australia, Quintis becomes the largest producer of sandalwood oil which is supplied for perfume and pharmaceutical use. India acquires the second position on the production of sandalwood essential oil because most of their producers are miniature and the pinnacle players include Katyani Exports, RK-Essential Oils, Karnataka Soaps and Detergents, Naresh International, Meena Perfumery, etc. Only several producers situated in Jiangxi and Guangdong province of China such as Jinagxi Xuesong, Sandalwood Forest, and Jiangxi Jishui are of stumpy yielding with not up to the mark in quality. India, North America, and Europe are dominating the consumption market of sandalwood essential oil. In India due to the forest fire, illegal felling, spike diseases, and grazing along with insufficient standardized regulation in the southern parts of India including Karnataka, Tamil Nadu, and Kerala and also for the high domestic and international demand making the sandalwood resources vulnerable. For these reasons in India, the export of sandalwood is banned excluding the handicraft pieces of sandalwood up to 50 g weight (Soundararajan et al., 2015). To retain the quality of essential oil there must be appropriate storage of this oil until their marketing or utilizing in fragrance and flavor consumer products by the industry. If the essential oils are improperly stored several factors like water, air, light influenced the composition of essential oil during long storage (Rao et al., 2011). It is reported that the alcohol-containing essential oil has the capacity to stable and withstand prolong storage. The Indian and Australian sandalwood species acquired up to 6–8 years of shelf life. In fresh conditions, essential oils are found to be free-floating and colorless or lightly colored. Due to oxidation and resinification processes, they become highly viscous and become darker in color on long storage. They are preserved in a chilled and dehydrated place in firmly stoppered amber glass bottles for the prevention of oxidation and resinification. Containers should be completely filled with oil to prevent air inclusion which prolongs the storage life of the oil. Certain chemical reactions including interaction of functional groups, polymerization, resinification, hydrolysis of esters, and oxidation are responsible for the degradation in the quality of the oil. The presence of heat, air, or oxygen and moisture mainly activates these processes of declining oil quality. In clarifications of essential oil, it is said that metallic impurities and moisture should not be present. The crammed, firmly closed containers should be stored at low temperatures and sheltered from light. For small quantities of oil bottles of rigid and shadowy colored glass are appropriate but large quantities of oils should be stored in aluminum containers or metal drums with tin lining. For the replacement of air above oil, a stream of CO2 or N2 gas is blown into the interior the container prior to sealed which prevent the oxidation reaction. Before storing, any dampness should be detached from the oil which is the main reason for spoilage of essential oil. Anhydrous sodium sulfate is used for the dehydration of smaller lots and then the container is shaken meticulously and reserved sideways for 24 h and filtered. For the removal of moisture and also waxy materials from the oil, centrifugation of the oil at a high speed of not less than 14,500 rpm is an exceptional method of purifying essential oils (Amer and Mehlhorn, 2006).

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6.8 Current understanding and prospects Recently, pharmacological studies revealed that the therapeutic significance associated with sandalwood essential oil and its components such as neuroleptic, combating cancer, diseases of viral origin, and skin nourishing agents (Dulal et al., 2019). Several studies expressed that α-santalol is a potential and safe chemotherapeutic agent against cancer. Studies revealed the mechanisms of activity by which α-santalol acts as an anti-cancer agent include antiinflammatory, antioxidant, antiangiogenic, and antiproliferative activities (Choudhary and Chaudhary, 2021). α-Santalol is found to be less toxic or non-toxic to usual cells, which reduces adverse side effects and complement the health of the patient. Although, further experimental studies are needed for enhanced understanding the activity of α-santalol, as a chemotherapeutic agent against several kinds of carcinogens (Santha and Dwivedi, 2015). The Sandalwood essential oil has been utilized as an Ayurvedic therapeutic representative for the medication of skin infections (Choudhary and Chaudhary, 2021). GC-MS and 13C NMR analysis have isolated α-santalol, a naturally appearing terpenoid, which is quantifying about 61% of the total constituent (Hasegawa et al., 2011). Bommareddy et al. (2017) reported that α-santalol stops ultraviolet B-induced skin tumor growth in a concentration-dependent manner. They also reported that α-santalol pretreatment potentially declined the skin tumor growth. Dulal et al. (2019) reported that sandalwood oil has various potential efficacies on the skin. The compounds of sandalwood oil can restore and rejuvenate wrinkle skin by various mechanisms such as anti-oxidative activities, NO (nitric oxide) scavenging activities, metabolic properties, anti-inflammatory properties, and cell regulatory properties. Further investigation is needed for a better understanding of sandalwood oil’s potentiality in the field of dermatological treatments and manufacturing of skincare products. Krishnakumar and Parthiban (2018) have investigated and characterized the sandalwood oil quality taken from various locations indicated the presence of 45 potential constituents and reported that the quality of the β-santalol followed by α-santalol remain almost the same in different localities, which is required in the scent industry. Sandalwood oil has been used in ethnomedicinal practices for the handling of digestive infections developed from gastritis, diarrhea, colic, nausea, coolant, and muscle relaxant. Sandalwood oil possesses antiseptic potentials, which have been significantly validated for the treatment of leucorrhea and gonorrhea (Shetteppanavar, 2017). Sandalwood oil is utilized for the treatment of depression, stress, nervous tension, and stress anxiety. Sandalwood oil also has an antiviral effect against Herpes Simplex Virus (Yadevendra et al., 2020). Sandalwood oil has potential evidence for treating blood pressure and self-rated arousal such as attentiveness, alertness, mood, calmness, vigor, and relaxation in humans (Shetteppanavar, 2017).

6.9 Conclusion Sandalwood is one of the significant and widely utilized plants in the cosmetic and perfume industry. Excluding cosmetic and perfume industrial utilization, sandalwood also has an extensive array of therapeutic properties and should be regarded as one of the most significant medicinal plants. Many researchers, worldwide have been focusing on the

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Sandalwood plant, which has been studied elaborately, although there are many aspects left to be explored to understand the complete benefits of sandalwood oil for humankind. Globally, several studies on sandalwood oil have been conducted to isolate the phytochemical components, especially both α-santalol and β-santalol, for understanding their physiochemical characters, synthesis, and pharmacological potential. Sandalwood oil is highly appreciable, not only for its exotic aroma and intensity but also for its medicinal properties. The application of sandalwood essential oil in the cure of skin diseases is excellent, as it significantly nourishes and moisturizes all types of skin. Based on the ethnomedicinal practices and modern therapeutic approaches, researchers evaluated that sandalwood essential oil is showing promising results against the treatment of many harmful diseases because of its phytochemical constituents. Several reports have validated the significant pharmacological potential of sandalwood oil and its phytochemical constituents from anticancer to antibacterial. All the important claims, facts and results incorporated in the present study may be extended for further scientific and clinical investigation which may lead to the new emergence of knowledge and can be used as a tool for the construction of research design in this field.

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Roy, S., Handique, G., Ahmed, R., Muraleedharan, N., 2017. Sandalwood oil (Santalum album L.): source of a botanical pesticide—present status and potential prospects. In: Nollet, L.M.L, Rathore, H.S. (Eds.), Green Pesticides Handbook. CRC Press, pp. 217–230. Santha, S., Dwivedi, C., 2015. Anticancer effects of sandalwood (Santalum album). Anticancer Res 35 (6), 3137–3145. Saraswati, S., Kumar, S., Alhaider, A.A., 2013. α-Santalol inhibits the angiogenesis and growth of human prostate tumor growth by targeting vascular endothelial growth factor receptor 2-mediated AKT/mTOR/P70S6K signaling pathway. Mol. Cancer 12 (1), 1–18. Shankaranarayana, K.H., Parthasarathi, K., 1984. Compositional differences in sandal oils from young and mature trees and in the sandal oils undergoing colour change on standing. Indian Perfum. 28, 138–141. Shankaranarayana, K.H., Ayyar, K.S., Rao, G.K., 1980. Insect growth inhibitor from the bark of Santalum album. Phytochemistry 19 (6), 1239–1240. Sharma, R., Bajaj, A.K., Singh, K.G., 1987. Sandalwood dermatitis. Int. J. Dermatol. 26 (9). Sharma, M., Levenson, C., Bell, R.H., Anderson, S.A., Hudson, J.B., Collins, C.C., Cox, M.E., 2014. Suppression of lipopolysaccharide-stimulated cytokine/chemokine production in skin cells by sandalwood oils and purified α-santalol and β-santalol. Phytother. Res. 28 (6), 925–932. Sharmeen, J.B., Mahomoodally, F.M., Zengin, G., Maggi, F., 2021. Essential oils as natural sources of fragrance compounds for cosmetics and cosmeceuticals. Molecules 26 (3), 666. Shetteppanavar, V.S., 2017. Recent developments in pharmaceutical and therapeutic applications of sandalwood oil. World J. Pharm. Pharm. Sci., 659–680 (August 2017). Sindhu, R.K., Upma, K.A., Arora, S., 2010. Santalum album Linn: a review on morphology, phytochemistry and pharmacological aspects. Int. J. PharmTech Res. 2 (1), 914–919. Soundararajan, V., Ravi Kumar, G., Murugesan, K., 2015. Trade scenario of sandalwood and its valued oil. Int. J. Novel Res. Mark. Manage. Econ. 2 (3), 52–59. Spafford, H., Jardine, A., Carver, S., Tarala, K., WEINSTEIN, P., 2007. Laboratory determination of efficacy of a Santalum spicatum extract for mosquito control. J. Am. Mosq. Control Assoc. 23 (3), 304–311. Starke, J.C., 1967. Photoallergy to sandalwood oil. Arch. Dermatol. 96 (1), 62–63. Subasinghe, U., Gamage, M., Hettiarachchi, D.S., 2013. Essential oil content and composition of Indian sandalwood (Santalum album) in Sri Lanka. J. For. Res. 24 (1), 127–130. Sundharamoorthy, S., Govindarajan, N., Chinnapillai, A., Raju, I., 2018. Macro-microscopic atlas on heartwood of Santalum album L. (Sandalwood). Pharmacogn. J. 10 (4). Tate, H.T., Page, T., 2018. Cutting propagation of Santalum austrocaledonicum: the effect of genotype, cutting source, cutting size, propagation medium, IBA and irradiance. New For. 49 (4), 551–570. Thomson, L.A., 2006. Santalum austrocaledonicum and S. yasi (sandalwood), ver. 2.1. In: Species Profiles for Pacific Island Agroforestry. Permanent Agriculture Resources (PAR), H olualoa, Hawaii. http://www.traditionaltree.org. Thomson, L.A.J., 2020. Looking ahead–global sandalwood production and markets in 2040, and implications for Pacific Island producers. Aust. For. 83 (4), 245–254. Trattner, A., Hodak, E., David, M., 1999. Screening patch tests for pigmented contact dermatitis in Israel. Contact Dermatitis 40 (3), 155–157. Van Thoai, V., Srivastava, A., 2020. Sandalwood Cultivation and Utilisation. Walnut Publication. Yadevendra, Y., Arun, S., Usha, S., Khemchand, S., 2020. Auspicious offering of Lord Shiva as a source of natural antiviral compounds against COVID 19: a review. Sch. Int. J. Tradit. Complement. Med. 3 (7), 1. Yan, C., Liu, H., Lin, L., 2013. Simultaneous determination of vitexin and isovitexin in rat plasma after oral administration of Santalum album L. leaves extract by liquid chromatography tandem mass spectrometry. Biomed. Chromatogr. 27 (2), 228–232. Zhang, X.H., da Silva, J.A.T., Jia, Y.X., Zhao, J.T., Ma, G.H., 2012. Chemical composition of volatile oils from the pericarps of Indian sandalwood (Santalum album) by different extraction methods. Nat. Prod. Commun. 7 (1). 1934578X1200700132.

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C H A P T E R

7 Jasmine essential oil: Production, extraction, characterization, and applications Mohammad Makeria and Aliyu Salihub a

Food Technology Department, NAERLS, Ahmadu Bello University, Zaria, Kaduna State, Nigeria b Department of Biochemistry, Ahmadu Bello University, Zaria, Kaduna State, Nigeria

7.1 Introduction The essential oil (EO) is a group of volatile and semi-volatile organic compounds that along with some phytochemical and bioactive constituents combined to form complex mixtures of compounds whose properties influences the aroma of their source (usually plants) as well as their flavor and fragrance (Sirousmehr et al., 2014; Tisserand and Young, 2013). They are termed essential oil probably because they represent a distinct essence of aroma and savor of aromatic extracts from plant matter (flowers, leaves, branches, roots, gums, and fruits) as well as animal secretion extracts (Meyer-Warnod, 1984; Tongnuanchan and Benjakul, 2014). The plant-sourced EOs are derived from a variety of plants and diverse sections of those plants, such as rhizomes (ginger), flowers (jasmine) leaves (peppermint), bulbs (garlic), bark (cinnamon), fruits (lemon), seeds (fennel), dried flower buds (clove) grasses (lemongrass), gum (frankincense), tree blossoms (ylang-ylang), wood (cedar), etc., and extensively employed in the cosmetic and food industries (Tisserand and Young, 2013). They are highly volatile secondary metabolites derived from plant material through special extraction methods or other technique (due to their volatility) and named after the plant (or source) from which they are obtained. Majority of ornamental and some flowering plant families including Oleaceae (to which Jasmine belong) are well-known for their ability to synthesize essential oils (EOs) having medical, therapeutic, and industrial applications (Hammer and Carson, 2011; Tisserand and Young, 2013).

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00013-X

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Copyright # 2023 Elsevier Inc. All rights reserved.

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7.1.1 The jasmine plants Jasmine (Jasminum spp.) is a flowering plant in the Oleaceae family that is grown commercially in India and other south-east Asian nations such as Singapore, Malaysia, and the Middle East. Though each part of the plant from the roots, stem, nodules and leaves of the jasmine crop have peculiar perfumery, medicinal and therapeutic uses and applications in the domiciliary area of production, the flower forms the principal product because of its content of essential oil that makes it distinct from other essential oils, and consequently it forms the primary product of the jasmine crop (Ganga et al., 2019). Jasmine is one of India’s most important commercial flower crops; the country is the world’s largest producer of jasmine and jasmine products. Jasmine or jessamine (Jasminum spp.) of the genus Jasminum is a group of fragrantflowered shrubs and vines comprising more than 200 species of the olive family (Oleaceae). The plant, cultivated as ornamental climbing plants with no tendrils, is native to tropical climates, however, sub-tropical and temperate climate varieties are now available. The tubular, flaring, lobed, and pinwheel-like blossoms of the jasmine plant are normally white or yellow but rarely pink in appearance. Jasminum nudiflorum is traditionally ornamental and bear yellow flowers whereas J. officinale and J. grandiflorum are perfumed species and have large white flowers. The flowers are normally single-flowered, however due to demand for aromatherapy and holistic uses, some double-flowered cultivars have been developed ( Jonard, 1989). The leaves are either evergreen or deciduous, consisting of two or more leaflets in most species, with some species having a simple leaf structure. Most species produce a two-lobed black berry that was once planted as a decorative plant and nurtured for cultural and religious purposes, particularly in India, China, Italy, Spain, and the Oceania.

7.1.2 Major species There exist at present many varieties of jasmine plant depending on the climate conditions and values. The main species include commonly grown poet’s jasmine that is native to Iran and produces white, fragrant flowers rich in the attar of jasmine used in perfumes, the Arabian jasmine (Jasminum sambac), Spanish jasmine (J. grandiflorum), Flowering Bush jasmine (Jasminum auriculatum) and the winter jasmine (J. nudiflorum), as shown in Fig. 7.1. Other less cultivated species include White jasmine, Italian jasmine (J. humile), Confederate jasmine

Winter jasmine (Jasminum nudiflorum)

Doubled-flower Arabian jasmine (Jasminum sambac)

Flowering jasmine bush (Jasminum auriculatum)

FIG. 7.1 Some important species of jasmine flowers at bloom ready for harvest. Britannica, 2021. The Editors of Encyclopaedia. "Jasmine". Encyclopedia Britannica. https://www.britannica.com/plant/jasmine-plant (accessed 31.05.2021).

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(Trachelospermum jasminoides), Cape jasmine (Gardenia jasminoides), Madagascar jasmine (Marsdenia floribunda), Jasmine tobacco (Nicotiana alata), Carolina, Chilean jasmine (Mandevilla suaveolens), and others. Among all the species, the most commonly cultivated jasmine plant are: (1) J. grandiflorum, a species native to Arabian peninsula, South Asia, India, East and Northeast Africa and the Yunnan and Sichuan regions of China, is widely cultivated in India and across the Maldives, Mauritius, Java, the Central America and the Caribbean; (2) Arabian jasmine (J. sambac) is a jasmine species native to tropical Asia, ranging from the Indian subcontinent to Southeast Asia. It is widely grown, particularly in South and Southeast Asia. (3) The winter jasmine, J. nudiflorum, comes from China, Burma (Myanmar), Nepal, and Bhutan, and travels through India, Pakistan, and Arabia (Saudi Arabia, Oman, Yemen) to eastern Africa (Egypt, Sudan, Ethiopia, Eritrea, Somalia, Uganda, and Kenya). It is now widely cultivated as an ornamental plant and is reportedly naturalized in France and other places (Texas, Oklahoma, Georgia, Tennessee, Maryland, and New Jersey) across the United States (Oyen and Dung, 1999). J. sambac (L.) especially has its origin from the South-western and Southeast Asian countries (Philippines, Myanmar, India, and Sri Lanka) and classified under the genus Jasminum of the olive family Oleaceae. Fig. 7.1 shows some of the cultivated jasmine flowers and how they differ in their physical properties. In the early 18th century, J. sambac expanded to the Middle East, Persia, and parts of Europe, and it is today cultivated in almost all tropical and subtropical regions of the world, where it is known as Arabian Jasmine and utilized as a significant therapeutic herb for headache and rheumatism (Oyen and Dung, 1999). The popular jasmine tea is made from the aromatic dried flowers of Arabian jasmine (J. sambac). Though most jasmine species are planted for their aroma and perfumes, and also used as decorative plants, some have no fragrance including some genus such as Japanese jasmine (J. mesnyi) or primrose. The true jasmines (Jasminum spp.), however, either as vines or shrubs usually bear white, yellow, or pink intensely fragrant flowers that are generally rich in essential oils. J. sambac, especially, is popular in many Asian and middle-eastern countries, and thus widely grown for its essential oil due to its proven medicinal, therapeutic, and perfumery properties (Patel and Gogna, 2015; Ahmed et al., 2016). The three species usually employed in the commercial production of jasmine essential oil are J. sambac, J. grandiflorum, and Jasminum auriculatum (Ganga et al., 2019; Green and Miller, 2009b; Oyen and Dung, 1999).

7.2 Production and composition 7.2.1 Production and market trends Essential oils production is becoming an important upstream agricultural sector at a number of locations across the globe because of the growing demand for essential oils for use in a wide range of applications ranging from foods, cosmetics to aroma-therapy. The average annual yield of jasmine flower varies with species and method of propagation used, and ranges between 5 and 8 ton/ha, whereas some commercial jasmine plantations yield averaged 8–10 tons per ha under optimum cultural practices. In India, the average annual flower yield for J. auriculatum and J. sambac ranges from 2 to 9 ton/ha and 1 to 7 ton/ha and with average yield

150

7. Jasmine essential oil: Production, extraction, characterization, and applications

of concrete of 0.3%–0.4% and concrete yield of 0.1%–0.2%, respectively (Oyen and Dung, 1999). The flower yield of J. grandiflorum on the other hand ranged from 5 to 5.5 ton/ha with about 8000–8500 flower heads per kg. J. grandiflorum plant grafted on J. officinale produces less flowers of 3–3.5 ton/ha ( Jonard, 1989). An average of 420 kg of jasmine flowers could yield about 2 kg of concrete or 1 kg of absolute (Meyer-Warnod, 1984). The global demand for essential oils was 226.8 kton in 2018, and is expected to reach USD 13 billion by 2024 as customers shift to organic and natural goods (Irshad et al., 2020). This recent trend could be fueled by changing lifestyles of people to counteract “diseases of civilization” that are associated with reduced physical activity and poor lifestyle. According to data on import spending from 2000 to 2008, the top five import markets are the United States of America (US$391 million), France ($199 million), the United Kingdom ($175 million), Japan ($152 million), and Germany ($117 million), with the fastest growing import markets being Vietnam (14% per year), Poland (35% per year), Nigeria (16%), Turkey (25%), and South Africa (13%) (Raju et al., 2015). Globally, the amounts of essential oils produced vary widely between countries. The yearly output of the main essential oils is about 35,000 tons per year on average, while for the minor essential oils, just a few kilos. Around 200 different essential oils are produced and traded globally in quantities ranging from 20 to 30,000 tons for main essential oils (orange, lemon, tangerine, lime, grapefruit, etc.) to less than 100 kg for minor EOs like clove bud, coriander, cinnamon, garlic, nutmeg, onion, and so on. India produces the most jasmine and jasmine products in the world that have huge domestic market demand and exports to distant markets including Europe and USA (the largest user of essential oils), followed by Egypt (Ganga et al., 2019). In 2007, India alone produced 4700 kg of jasmine concrete whereas Egypt produces 3500 and 1000 kg of concrete and absolute, respectively (Lawrence, 2009). A large portion of the jasmine flowers produced is sold to neighboring nations such as Singapore, Malaysia, and the Middle East, as well as to distant international markets such as the United States. J. grandiflorum flowers are primarily grown for the production of jasmine absolute oil in India, Egypt, and Morocco, whereas J. sambac flowers are cultivated in India for ornamental purposes, religious offerings and garlands, with only about 5% of the annual harvest used to produce jasmine absolute oil. J. grandiflorum is also commonly cultivated for its aromatic blooms, which are used as an ornamental and a source of oil in warm temperate, sub-tropical, and tropical regions across the world (Oyen and Dung, 1999). In China, some Southeast Asian countries and the Middle East, the flowers of J. sambac especially are used as flavoring in tea drink to impart the characteristic savory of the jasmine plant. The essential oil is employed in aromatherapy for symptomatic treatment of depression and for reverting moods. Thus, because of the valued medicinal properties of this plant, pharmaceutical companies export jasmine products from countries including India and Bangladesh where cultivation is promoted through in vitro micro-propagation; a rapid method of propagation by cloning of the original parent species under a short time period (Rahman et al., 2018). Prices for major EO that are marketed in volumes vary from US$4 to $60/kg, while prices for specialty minor oils can reach US$100/kg (Schmidt, 2020). However, global EOs production figures should be handled with care because they are based on limited statistical data and because domestic consumption is hardly documented in most producing nations, in addition to the fact that export data is based on records for just the high-volume or major EOs. Specialty EOs like jasmine oil (Jasmine spp.), lavender oil (Lavendula officinalis), rose oil (Rosa damascene spp.), geranium oil (Pelargonium graveolens) and other nonconventional EOs

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are sometimes grouped together under codes that cover a wide variety of small goods (Douglas et al., 2005). In more specialized applications, the bulk of the other oils are utilized in considerably smaller amounts.

7.2.2 Planting and propagation Depending on the cultivar, the jasmine plant can be reproduced by seed or stem/cutting. The few types that can be grown from seed, however, do not generate seeds and successive plants are propagated only by cutting, layering, marcotting, or grafting on chosen root-stocks as well as other asexual methods. Though crop improvement through classical hybridization, genetic manipulation and suckers, grafting, budding and tissue culture (in vitro propagation) has shown some successes, propagation of jasmine by layering and cuttings remain the most promising means of raising the plant (Chaitanya and abd Nataraja, 2018; Palai et al., 2017). This is due to the fact that seed production output is often poor with viability hovering around 50% and barely lasting 6 months. Cuttings of 12–20 cm long are obtained from terminal branches and buried 15 cm deep, but the rooted layer is removed from the parent plant and transferred after layering is completed. For optimum yield, Jasmine plant is supported either individually using stakes or posts or in group or out-door lattice or trellises to the wireand-post systems as in vineyards. Plant spacing of 2 m
1.5 m or 1 m
1 m are usual for a hectarage of between 4000 and 30,000 cuttings per ha, although much tighter planting is occasionally done (up to 30,000 plants per ha). For frost protection, J. grandiflorum is grafted on 2- or 3-year-old rootstocks of J. officinale in areas of France, but this is not usual in milder climates. The plant grows to a height of about 9.8 ft. high producing attractive, white or yellow flower with strong, sweet-scented aroma especially during the hot season. Once the plant attains maturity, it starts producing flowers in clusters of 3–12 at the tip of leaves and branches. The flower has a diameter of 2–3 cm with 5–9 lobes that open at night and close in the morning as it blooms throughout the year, with production maxima between March and July (Leonhardt and Teves, 2002; Skaria et al., 2007). EOs are stored in plant glands as micro duplets in the cytoplasmic cells of the petal, which progressively diffuse through the gland and disseminate on the surface of plant parts as extremely fine volatile micro-droplets.

7.2.3 Growth and development During the first years of life, growth of jasmine plant is slow long before flowering commences at about 6–7 months. Thereafter, flowering becomes profuse and mature plant can flowers for up to 7–9 months per year in warm regions and 4–6 months in temperate regions of the world (Green and Miller, 2009a). High day and low night temperatures stimulate early flowering in J. grandiflorum species, which occurs in Egypt, Europe, and northern India between July and October, and in southern India, from May to December. The flowers open early morning when EO content is at peak and decreases considerably from 10 am in the morning (Oyen and Dung, 1999). In Europe, jasmine blossom oil concentration is significantly higher in August and September than in July and October. Jasmine plantations that are wellmanaged can last up to 15 years or more (Charan, 1979).

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7.2.4 Husbandry Jasmine must be weeded regularly while taking care to prevent damage to roots. The plant reacts well to both organic and inorganic fertilizers distributed in 12 monthly doses of roughly 60 g N, 120 g P, and 120 g K per plant. NPK 10-15-10 is sufficient if plant residues or farmyard manure are not sprayed during planting, but exact amounts should be established by soil analysis. Pruning is required to promote new growth and branches, as well as to eliminate sick or dead shoots and keep flowers within reach for harvesting. Jasmine also suffers from a number of pests, however, only few such as cockchafer (Scarabaeus melolontha) found especially in Europe and the Middle East and Cetonia aurata found in warm climates are economically important. Pythium spp., Phytophthora spp., and Fusarium spp. cause root and stem rots in jasmine. Cercospora spp., Puccinia spp., Alternaria spp., and Septoria spp., on the other hand, can create leaf spots on jasmine plants (Husain, 1984). In severely wet or humid circumstances, Botrytis spp. bud rot can be highly destructive. Almost all infestations, on the other hand, may be avoided or greatly reduced by burning plant cuttings and detritus. Reports of caterpillars that cause damage to foliage in Europe and in the Middle East have been linked to Acherontia Atropos, but in Asia and other warn climates, the army worm (Spodoptera exempta) and bud worm (S. littoralis) are the main concern. Spider mites (Tetranychus spp.) attack and cause severe defoliation of jasmine plant.

7.2.5 Harvesting and handling Only half-opened and fresh, completely opened Jasmine blossoms are collected manually between daybreak and 10 a.m. when they are ripe. This is because harvest time significantly affect the composition and quality of jasmine EO with concentration of indole and cis-jasmone compounds higher in jasmine flower harvested in the morning than that harvested in the afternoon/evening (Ahmad et al., 1998; Charan, 1979). Similarly, compared to eveningharvested flowers, aroma-bearing flowers picked in the morning produce higher quality oil-containing compounds such as linalool, benzyl alcohol, and benzyl acetate, whereas other aroma-bearing compounds such as farnesol, methyl palmitate, eugenol, benzyl benzoate, and methyl salicylate are found higher in concrete derivate (Ahmad et al., 1998). Immediately after harvest, Jasmine flowers are handled by processing them into respective products because delays significantly decrease their essential oil content. And like any other food product, quality of jasmine flower starts to deteriorate immediately after harvest. In a processing facility that should be near to the plantation, the flowers should be kept in the shade and in a cool environment. Fresh flowers gathered before dawn can be kept in polythene bags at 4 to 15 °C for a few days with minimal loss of yield, quality, or odor. Previously, Jasmine concrete was made from flowers using effleurage and solvent extraction, but it is now made from flowers using steam distillation, however, with a consequent lesser yield. The flowers are washed up to three times with petroleum ether or, preferably, food-grade n-hexane in the solvent extraction process and the extract is then distilled to remove the solvent, giving the concrete. Jasmine pure or jasmine essential oil is generally manufactured in the importing nation, whereas concrete is usually created on the plantation. Postharvest handling techniques such as treatment with floral preservatives and packaging can considerably help in extending the shelf life of jasmine flowers. Harvested jasmine flowers should preferably be stored at 4°C or

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153

lower to preserve the scent intensity of the floral volatile components because storage for up to 30 months at ambient temperature substantially reduces the amount and quality of strong odorants including linalool, indole, and methyl anthranilate (Zhou et al., 2019). Flowers are protected from mechanical harm by packaging which acts as a barrier between the interior and outside environment. It shields the flowers from the elements and allows for the development of a microclimate within the package (Ganga et al., 2019; Nowak et al., 1991). During transit and storage, packaging helps to reduce the rate of transpiration, respiration, and cell division.

7.2.6 Composition and physicochemical properties Like most other plant-derived essential oils, jasmine EO comprised of volatile terpenes and nonterpene hydrocarbon molecules such as alcohols, esters, aldehydes, ketones, epoxides, sulfides, and others. The majority of hydrocarbons are monoterpenes, sesquiterpenes, and diterpenes (Bas¸ er and Demirci, 2007). Two broad categories of compounds generally identified in essential oils are the hydrocarbons (carbon and hydrogen only) and oxygenated hydrocarbon derivatives, broadly composed of volatile and nonvolatile components. The volatile and nonvolatile fractions of jasmine essential oil make up 90%–95% and 5%–10% of the oil’s weight, respectively. The volatile fractions consist of hydrocarbons containing oils such as fatty acids, carotenoids, sterols, flavonoids, and waxes, as well as their oxygenated derivatives, aliphatic aldehydes, alcohols, and esters. The nonvolatile residues on the other hand comprised of hydrocarbons containing oils such as fatty acids, carotenoids, sterols, flavonoids, and waxes. Thus, most of the aroma and odor characteristics of the jasmine essential oils are attributed to the volatile oxygenated hydrocarbons including the terpenes (Clarke, 2008). It is the oxygenated constituents that have a significant impact and, along with sesquiterpenes, determine and influence the characteristic aroma of jasmine essential oils. Benzyl acetate, benzyl benzoate, linalool, isophytol, phytol, phytol acetate, methyl jasmonate, jasmine, geranyl, benzyl alcohol, indole, benzyl benzoate, cis-jasmone, and palmitic acid are the primary chemical compounds of jasmine oil present in variable amounts (Mourya et al., 2017; Oyen and Dung, 1999). The other minor components ranged between less than 1% and 5% (Abid Mahmood et al., 2017). Benzyl acetate, benzyl benzoate, phytol, linalool, isophytol, geranyl linalool, methyl linoleate, and eugenol, all of which are present in J. grandiflorum, are the main components responsible for the popular jasmine fragrance (Mourya et al., 2017). Jasmine EO also includes nonterpene aromatic chemicals such as benzyl acetate, methyl anthranilate, and 3-hexenyl benzoate, in addition to terpenes. Linalool and (3E,6E)-farnesene were found to be the main monoterpene and sesquiterpene in all four major jasmine species, respectively. These chemicals are responsible for the jasmine EO’s attractive odor as well as its antidepressant and antibacterial effects. Generally, however, jasmine oil contained about 200 compounds with only 28 that are aroma-bearing. Among all these, indole, cis-jasmone, and methyl jasmonate are the most important constituents that symbolize the jasmine aromatic fragrance (Ahmad et al., 1998; Raju et al., 2015; Husain, 1984). β-Farnesene (52.52%), nerolidol (19.85%), and benzyl alcohol (17.56%) were found in the methanol extract of J. sambac, whereas linalool (35.92%), benzaldehyde (17.92%), and benzyl

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7. Jasmine essential oil: Production, extraction, characterization, and applications

alcohol (17.56%) were found in the headspace solid phase microextraction (HS-SPME) (10.87%). Similarly, hydro-distillation revealed substantially different quantities of the major compounds extracted utilizing the extraction method: farnesene (45.13%), cadinol (26.21%), and linalool (26.21%) (9.96%). Similarly, the methanol extract of J. multiform produced nerolidol (42.44%), benzyl benzoate (39.00%), and jasmolactone (12.02%), whereas HS-SPME eluted nerolidol (76.56%), jasmone (15.31%), and hexyl benzoate (4.40%), while hydro-distillation generated β-farnesene (24.62%), hexenyl benzoate (35.89%), and α-cadinol (14.30%) (Khidzir et al., 2015). Other major chemical components include benzyl acetate, linalool, benzyl alcohol, indole, benzyl benzoate, cis-jasmone, geraniol, methyl anthranilate, and trace quantities of p. cresol, farnesol, cis-3-hexenyl benzoate, eugenol, nerol, ceosol, benzoic acid, y-terpineol, benzaldehyde, isohytol, phytol, nerolidol, cis-3-hexenyl benzoate, etc. The extraction process used in the extraction and recovery of the oil, in general, determines the composition (Sell, 2010) (Table 7.1).

TABLE 7.1 Classes of compounds identified in jasmine essential oils as affected by methods of extraction. Relative abundance (%) Jasminum sambac

a

Jasminum multifloruma

Jasminum multiflorumb

Compounds

Hydrodistillation HS-SPME Hydrodistillation HS-SPME Solvent

trans-4-Hexenal

ND

9.36

ND

ND

Benzaldehyde

0.61

2-Hexenol

ND

5.30

ND

ND

Benzyl alcohol

13.85

Benzaldehyde

4.27

17.92

ND

ND

trans-Linalool oxide 0.12

Mycrene

ND

5.44

ND

ND

Linalool

4.92

Hexenyl acetate

0.25

ND

0.14

ND

Phenethyl alcohol

0.68

Benzyl alcohol

17.56

10.8

0.39

0.10

Indole

0.11

2-Phenylacetaldehyde 3.40

10.24

ND

ND

Benzyl acetate

1.24

Tolualdehyde

1.30

ND

0.71

ND

cis-linalool oxide

0.04

Linalool

9.96

35.92

5.43

0.26

Methyl salicylate

0.15

Phenyl ethyl alcohol

1.23

2.367

0.94

ND

Benzoic acid

0.11

0.58

ND

ND

ND

Phenethyl acetate

0.D3

Benzyl acetate

1.64

ND

0.89

ND

Gamma-elemene

0.14

Indole

ND

ND

ND

0.04

Butyl benzene

0.06

Elemene

0.49

ND

0.26

ND

Alpha-copaene

0.D2

Copaene

0.46

1.11

ND

ND

Ethyl anthranilate

0.46

ND

ND

4.06

15.31

Beta-patchouene

0.04

Caryophyllene

0.50

0.52

ND

ND

Beta-elemene

0.24

Farnesene

45.13

0.82

24.62

1.70

cis-jasmone

0.01

Terpineol

Jasmone

155

7.3 Extraction techniques

TABLE 7.1 Classes of compounds identified in jasmine essential oils as affected by methods of extraction—cont’d Relative abundance (%) Jasminum sambac

a

Compounds

Jasminum multifloruma

Jasminum multiflorumb

Hydrodistillation HS-SPME Hydrodistillation HS-SPME Solvent

Humulene

ND

ND

0.54

0.06

Beta-caryophyllene

0.13

Cadinene

1.32

ND

12.30

ND

Alpha-cubebene

0.07

Di-tertbutyl phenol

ND

ND

ND

ND

Beta-gurjunene

0.06

Jasmolactone

ND

ND

12.02

ND

Alpha-humulene

0.09

Nerolidol

19.85

ND

42.44

76.56

Delta-cadinene

0.11

Hexenyl benzoate

ND

ND

35.89

0.58

Eugenol

0.02

Viridiflorol

3.12

ND

ND

ND

Valencene

0.08

Hexyl benzoate

ND

ND

ND

4.40

Alpha-gurjunene

0.27

26.21

0.14

14.30

ND

Isocryophyllene

7.83

Farnesol

ND

ND

0.34

0.25

Alpha-ylangene

0.48

Benzyl benzoate

5.66

ND

39.00

0.74

Alpha-muurolene

0.13

Cadinol

a

Khidzir et al., 2015. Husain (1984). HS-SPME, head-space solid micro-extraction. b

Benzyl acetate was the most common benzenoid found in jasmine flowers. The composition, amount, and kinds of chemicals released by flowers of these four jasmine species, namely J. sambac, J. auriculatum, J. grandiflorum, and J. multiflorum, differed when volatile profiles were compared (Bera et al., 2015). Linalool’s bioactivity is connected to the antibacterial characteristics of most terpenoids, with the hydroxyl group of phenolic terpenoids, as well as delocalized electrons, being responsible for this antimicrobial activity (Raju et al., 2015).

7.3 Extraction techniques Extraction processes such as solvent extraction, steam distillation, enfleurage, maceration, can be used to obtain Jasmine essential oil from plant materials, each with its advantages and disadvantages. However, some of the most commonly used methods for extracting EOs such as steam distillation, water distillation, hydro-diffusion, manual expression, and supercritical fluid extraction (SFE) are associated with a variety of drawbacks ranging from lower yield to decomposition of oil essence and fragrance to low oil recovery (Zizovic et al., 2007; Carvalho Jr et al., 2005). For example, two different techniques could yield same amount of essential oils from the same plant material but with different composition because not all components are extracted equitably well by each of the methods, and that during the extraction process, several individual components may undergo modifications. Regardless of the

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method utilized, the physical approach used to extract the essential oils has an impact on the chemical makeup of the finished product (Zizovic et al., 2007). Thus, because essential oil also contains both fragile, volatile compounds, extraction process requires specialized method in order to recover quite as much of the delicate products with little or no damage to physical and chemical state of the oils. After extraction, some essential oils could be separated into their respective chemical constituents for use directly, or may be further processed into different aromatic compounds as practiced in the perfumery (De Padua et al., 1999; Oyen and Dung, 1999). Jasmine EO derived by SFE of the flowers is comparable to those obtained through distillation and both may be utilized in aromatherapy and natural perfumery. However, the operating conditions for the extraction process, such as temperatures, pressures and time may change. Jasmine EO extracted using SFE could have higher quality than EO derived through steam or hydrodistillation since the former may not have undergone severe extraction conditions. Because none of the components of the oil come into touch with heat, the CO2 extraction method may generate high-quality EO (Masango, 2005). Additionally, due to the high temperatures used in steam distillation, the compositional components of both the plant matter and the essential oil are significantly altered. CO2 extracts, on the other hand, are chemically closer to the parent plant since they include a wide spectrum of the plant’s original components. The primary difference between distillation and supercritical fluid extraction is that the latter uses CO2 as the extracting solvent instead of hot water or steam (Masango, 2005). In addition, the SFE technique runs at temperatures ranging from 35 to 37°C, whereas steam distillation operates at temperatures ranging from 60 to 105°C. In the former, the waxes, plant pigments, and other odorless or nonodoriferous materials have been eliminated. As a result, the absolute yield is determined by the concrete’s quality (Razaki, 2014). To conserve natural floral, aromatic and the sweet fragrance of the Jasmine essential oils therefore, steam-distillation and supercritical fluid extraction (SFE) are the popular methods used in extracting the EOs. Recent studies, however, showed that Jasmine EO obtained from J. sambac by CO2 supercritical fluid extraction method yielded 0.334% of concrete oil with resulting 0.021% of absolute (or pure EO) and the quality was better than that obtained by hydro-distillation (Younis et al., 2017).

7.3.1 Steam distillation Steam distillation works on the concept where the plant material is exposed to steam (or boiling water) and mixtures of components are volatilized at a temperature slightly over 100° C and atmospheric pressure. The vapors containing the volatiles are cooled in a condenser and the liquid oil recovered. The dried or fresh jasmine flower is placed in the column’s distillation chamber, and steam is allowed to pass through the plant matrix under pressure, wilting the cells and allowing the oils to vaporize in the form of vapor. As both the steam and the oil droplets vaporize and flow through the tube into the condensation chamber of the distillation column, the steam temperature should be high enough and for long enough (about 200°C, distilled for 5–6 h) to volatilize the oil present. Oil vapors condense with water vapors forming an essential oil layer on the water’s surface. The floral water (or hydrosol) is left as a by-product of the distillation process after the thin layer of oil is skimmed away.

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7.3 Extraction techniques

Decanter

Condenser

Plant matter

Steam Essential Oil

Boiling Water

Boiler

Waste Water

FIG. 7.2 Schematic illustration of a steam-distillation extraction process.

The oil-containing distillate can alternatively be collected and dried over anhydrous magnesium sulfate (MgSO4) followed by centrifugation at 1300 rpm for 30 min to separate it further. Typically, a plant mass of 4246 kg dried flowers of J. officinale would yield about 170 g pale yellow Jasmine essential oil; a 0.4% recovery from the plant material. The by-product possesses therapeutic properties widely used in making skin and facial preparations, or employed in the treatment of young persons or the elderly where a very dilute jasmine essential oil is desired (Bousbia et al., 2009; Sharma and Gupta, 2020). The quality of essential oils extracted via the steam distillation technique, on the other hand, varies depending on the temperatures and pressures used, as well as the amount of time it takes to complete the process. The steam generated by the boiler moves into the ground flower materials as heated vapor and removes the aromatic and fragrant compounds and along with it passed into the condenser, as illustrated in Fig. 7.2. By principle, the condenser converts the contents of the vaporized materials into liquid form. The condensate separates into the oily and aqueous components that are by nature immiscible and, based on density differences, the oily part is decanted off the waste water which remains at the bottom and is removed.

7.3.2 The steam distillation process The whole steam-distillation extraction processes can be summarized under three main steps as follows: 1. The macerated plant material is placed in a large stainless-steel container referred to as the Still. 2. Steam is pumped into the plant material containing the essential oils through an input, releasing the aromatic molecules as they vaporize. 3. The vaporized aromatic compounds are transferred to a condensation chamber (where two separator pipes are stationed and where hot water departs and cold water enters the condenser simultaneously) where they are cooled and converted to liquid form, and then to the decanter. 4. The aqueous component (which comprised the waste water and other hydrophilic compounds) settles to the bottom as the oily part is decanted off.

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7. Jasmine essential oil: Production, extraction, characterization, and applications

Finally, the aromatic liquid by-product falls from the condenser and gathers beneath it in a container. The essential oil separates out from the mixture of water and oil by floating on top of the water from where it is decanted off.

7.3.3 Super critical fluid extraction (SFE) SFE (supercritical fluid extraction) is a method of separating one component (the extractant) from another (the matrix) by utilizing supercritical, highly compressed gaseous fluids such as carbon dioxide (CO2) as the extracting medium in a supercritical region. The supercritical condition is usually around 31°C and a pressure of 74 bar. Though many fluids can be used (because the technique raises the temperature and pressure above the fluid’s thermodynamic critical point), CO2 is the most commonly used because it requires less pressure to liquefy, is less reactive, is nonflammable, nontoxic, is inexpensive with high purity and can be separated from the plant material by simply releasing the pressure (Latief et al., 2017; Kamiie et al., 2014). SFE is an extraction method employed in the recovery of premium, highly valued foods and drug materials such as decaffeinated coffee, shark liver oil, essential oils, etc., with little or no damage to the extracting component (Ahmed et al., 2016). One major advantage of SFE, however, is the use of low temperature and a slightly higher pressure leading to the recovery of the component of interest with high purity and no solvent residues. Jasmine EO obtained from J. sambac by supercritical fluid extraction method using CO2 extracting medium yielded 0.334% of concrete oil, with resulting 0.021% of absolute or pure EO, and the quality was better than that obtained by hydro-distillation with a recovery of 0.08 g or 0.008% (Akram et al., 2017). Optimization of the operating conditions allowed rapid recovery of finest quality EO and component selectivity compared to the traditional solvent extraction.

7.3.4 Supercritical fluid extraction process The fundamental operations of the supercritical fluid extraction are presented in Fig. 7.3. The SFE extraction method employ the use of an apparatus which consisted of a storage vessel (or reservoir) for containing the liquid CO2 (A), an extractor (C) and two separating chambers (F). The fresh, early-morning harvested jasmine flowers are first dried at 30°C preferably under shade (to preserve the volatiles), and the ground plant material is placed in the extractor, where it comes in contact with the liquid CO2 at a suitable temperature and pressure (40° C, 300 bar). The extract is then passed through some valve (D) that reduces the pressure and then into the first separating chamber (E) maintained at 90 bar and 15–20°C (Masango, 2005). In this first separator (I), a mix of oil extract that comprised of fixed oils, triterpenes, sterols, carotenoids are recovered. Inside the second separator (II) maintained at lower optimum pressure and temperature conditions (20 bar, 15–20°C), separation by fractionation takes place by stage-wise precipitation, and most of the volatile oil rich extracts are recovered (Kakasy et al., 2001). Thus, the fractions are recovered and collected successively with time as the extraction process progresses with windows for optimization to attain highest recovery because the EO yield is affected by both the pressure and temperature. The pressure between 100 and

159

7.3 Extraction techniques

B

E

Pump A

Separator I Pressure Release Valve

C

Separator II

Liquid CO2

D

Reservoir Plant Matter plus Liquid CO 2

Extractor F

Collector

FIG. 7.3 Schematic diagram of a CO2 supercritical fluid extraction process.

200 bar significantly increased the oil yield with the highest yield obtained at 200 bar. At the optimum SFE conditions of 200 bar and 325 K, the optimal yield of EO recoverable from Jasmine flower stand at 122 mg oil/kg dry flower (Rassem et al., 2019). Concrete yield is around 0.1%, while India has recorded up to 0.3%. As a rough estimate, 1000 kg flowers generate 1 kg concrete when extracted using solvents, with only half of it being absolute. Conditions for optimum yield by SFE are 297.71 bar and of 317.78 K which could result in higher recovery and maximum yield value of 75.83% (Haloui and Meniai, 2017). In general, gentle extraction conditions allowed for greater uptakes of the most volatile compounds, whereas harsh extraction conditions resulted in a higher extraction rate of the semi-volatile compounds, but with increased oxidation of the components as a result (Vichi, 2010). The supercritical fluid extraction process takes place at temperatures ranging from 35 to 38°C, whereas steam distillation takes place at temperatures ranging from 60 to 100°C. The basic operational principles of the CO2 extraction steps are as follows: • Pressurized carbon dioxide is converted to a liquid while staying in a gaseous form, referred to as the “supercritical” phase. The gas is injected into the chamber packed with crushed flowers in this state. • Due to the CO2’s liquid characteristics, it acts as a solvent on the crushed floral matter, removing the oils and other plant materials such as color and resin, and the EO then dissolves in the liquid CO2. • The liquid CO2 is then returned to its original gaseous form by releasing the operating pressure as it evaporates (as is recovered) while the resulting EO is collected. In SFE using CO2, the molecular composition of the essential oil is much closer to that of the original plant from which it is derived than that obtained using steam distillation due to the

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7. Jasmine essential oil: Production, extraction, characterization, and applications

BOX 7.1 Jasmine essential oils are divided into two categories: Jasmine Concrete and Jasmine Absolute. Because it may contain some mixture of other lipid compounds, jasmine concrete is impure jasmine essential oil

produced from the flowers of the jasmine plant. Pure jasmine essential oil (or jasmine absolute) is extracted from Jasmine concrete, a yellowish brown sticky oily material with the exquisite scent of real Jasmine blossoms.

temperature applied in the later. Consequently, the CO2 extracted oil might be higher in quality than steam distilled oils as they have not been affected by the application of high heat (Masango, 2005) (Box 7.1).

7.3.5 Analysis of jasmine essential oils Essential oils may be recovered from steam in a very easy method utilizing gas chromatography combined with mass spectrometry (GC-MS), which is an appropriate technology for EO analysis due to their nature as volatile metabolites with low boiling points. GC-MS in combination with head-space solid-phase micro-extraction (HS-SPME) is another popular technique for EO analysis. The yield of the absolute (40%–60% of the concrete) is determined by the concrete’s quality. Like the other ornamental flowers, Jasmine flowers pass through the stages of budding, blooming and finally wilting (Razaki, 2014). In general, the technique of extraction, packaging, and storage procedures have a significant impact on the composition and physicochemical characteristics of essential oils, which can change the oils’ biological qualities. Indole, cis-jasmone, and methyl jasmonate are particularly important constituents that characterize the jasmine fragrance (Christie, 2014; Indiresh et al., 1989). The scent of jasmine absolute is strong and rich flowery, with penetrant and fruity secondary notes (Temraz et al., 2009). Indole is notably linked with jasmine, where it is found in the absolute form at a concentration of 3%–5% and contributes significantly to the odor. It does, however, appear in a variety of different essential oils. 2-Phenylethanol is found in many plants, but it is notably significant in roses, where it makes up one-third to three-quarters of the oil.

7.4 Characterization of jasmine essential oils using NMR spectroscopy The identification and characterization of compounds complex in mixtures such as essential oils can be accomplished using a single technique or a combination of techniques such as high-performance liquid chromatography (HPLC), gas chromatography (GC), infrared spectroscopy (IR), Raman spectroscopy, or nuclear magnetic resonance (NMR) spectroscopy using mass spectrometry (MS) or flame ionization detectors as the case may be. However, owing to its capacity to offer information on the chemical composition of particular types of hydrogen and carbon atoms in varied and complicated combinations of essential oils,

7.5 Chemistry and properties

161

nuclear magnetic resonance spectroscopy stands out as a preferred method. This is because NMR methods, when combined with multivariate/chemometric analysis in the interpretation of NMR spectra provides discrete information on volatiles such as identification, characteristics, and physical and chemical properties (Silva et al., 2011; Skakovskii et al., 2010). The technology most commonly used in the characterization and elucidation of molecular structures of aromatic substances, notably essential oils, is H NMR spectroscopy. Because of the multitude of signals it gives, using H NMR spectroscopy to analyze and identify complex and comparable complex mixtures provides excessive benefits (Kubeczka and Forma´
cek, 2002). The H NMR is also employed to authenticate analytical data acquired by the GC-MS and to solve special difficulties with nonvolatile mixture components. The comparison of the oils spectrum and their fingerprints using broadband decoupling is the key idea in the use of NMR in the elucidation of essential oils. Using spectra of relative pure oil components or standards analyzed or measured under similar circumstances from solvent, temperature, and other analytic parameters to ensure that chemical shifts for individual NMR finger prints of the compound combination and the reference substance are negligible. The number of detected carbons, the number of intersected signals, and the difference in the chemical shift of each signal in the spectrum mixture and the reference or standard are used to identify each molecule. This enables identification and characterization of compounds that are stereo isomers or have close on GC-MS or do not have sufficiently-resolved spectra or co-elutes (Kubeczka and Forma´
cek, 2002). The NMR spectroscopic approach may also be used to ensure the purity of jasmine and other essential oils, as well as to detect fraud (Skakovskii et al., 2010; Blanc et al., 2006). It has been reported that H NMR has been used to identify, characterize, and/or authenticate a volatile component of essential oil (AbouZid, 2016; Hubert et al., 2011; Blanc et al., 2006). The quantification of important and minor compounds using NMR, however, poses some difficulty due to overlapping resonance and low chemical shift and its low sensitivity compared to chromatography (GC-MS, GC-FID) and need for large sample concentrate, though it provides better information. But when used along with chromatography, they work together to provide a full picture of the chemicals in mixtures, as certain molecules that are not visible with NMR spectroscopy may be identified with GC-MS or GC-FID (Freitas et al., 2018). Thus, for a better result, NMR should be employed in conjunction with GC-MS methods and/or chemometrics to corroborate the analyses as the advantage(s) and disadvantage(s) of the methods are complementary. The complementary use of NMR, GC-MS, and/or chemometric allows for the comprehensive identification, characterization, and/or authentication of the volatile content of essential oils (Freitas et al., 2018). Chemometrics is used in particular to gain a better knowledge and overview of the diversity of volatile components in essential oils from various jasmine plant species (Freitas et al., 2018; Skakovskii et al., 2010).

7.5 Chemistry and properties As secondary metabolites themselves, the most important basic constituents of the essential oils are usually the terpenoids, shikimates, polyketides, and alkaloids. Starting with

162

7. Jasmine essential oil: Production, extraction, characterization, and applications

FIG. 7.4 Some major compounds found in jasmine essential oils. NCBI, 2021. PubChem Compound Summary for CID 445995. National Library of Medicine, National Institutes of Health, Bethesda, MD, USA. Retrieved July 1, 2021 from: https:// pubchem.ncbi.nlm.nih.gov/compound.

photosynthetic reactions, green plants convert CO2 and water into glucose the cleavage of which yields phosphoenolpyruvate. Decarboxylation of phosphoenolpyruvate produces the two-carbon unit of acetate which is esterified by coenzyme-A to acetyl CoA (Bakkali et al., 2008; Carson and Hammer, 2010). Polyketides and lipids are formed when this species selfcondenses. Mevalonic acid is made from acetyl CoA as a starting point (Lis-Balchin et al., 1996), which is the primary raw material for terpenoids. The terpenes, especially monoterpenoids, may be cyclic (ring-form) or acyclic (linear), regular or irregular, with derivatives comprising of alcohols, phenols, esters, aldehydes, ketones, lactones, and oxides (Lambert et al., 2001). Geraniol, linalool, and citronellol, among other acyclic monoterpenes found in essential oils, might be regular, linear structures with a head-to-tail arrangement of isoprene units or cis-trans notation for stereoisomers of β-ocimene (Carson and Hammer, 2010). The schematic representations of the main aromatic components are presented in Fig. 7.4. Linalool, benzyl acetate, and benzyl benzoate are the three main components of jasmine essential oil, as mentioned above. Linalool is a monoterpenoid alcohol that may be found in a variety of antibacterial essential oils. Most terpenoids’ antimicrobial activity is connected to their functional groups, and it’s been shown that the hydroxyl groups of phenolic terpenoids, as well as the presence of delocalized electrons, are crucial for antimicrobial action. Linalool’s mechanism of action is linked to membrane expansion, increased membrane fluidity and permeability, disruption of membrane-embedded proteins, suppression of respiration, and changes in microbial ion transport pathways.

7.5 Chemistry and properties

163

Linalool (1), seen in Fig. 7.4, is an acyclic, monoterpene alcohol molecule found in the jasmine family, as well as lavender (Lavandula spp.), rose (Rosa spp.), and basil (Ocimum basilicum). It’s a molecule with the molecular formula C15H24 that’s present in a variety of essential oils, including jasmine and functions as a precursor to a number of other sesquiterpenes thanks to its open-chain structure and four double bonds (Sell, 2010). It may also be found in a broad range of isomers, including geometrics and stereoisomers. Linalool has a proven sedative, antidepressant, and immune boosting effects (McPartland and Russo, 2001). Linalool has been shown to have a synergistic antibacterial action when coupled with other monoterpenoids, such as phenolic monoterpenoids. Linalool has particularly been shown to have a synergistic antibacterial action when coupled with other monoterpenoids, such as phenolic monoterpenoids (Ahmed et al., 2016). This terpenoid also possesses analgesic and anticonvulsant effects in addition to potent sedative property observed which decreased motility in mouse under ambient condition (Russo and Marcu, 2017). Linalool is the prime suspect in the excellent therapeutic effects of lavender EO in healing skin burns in aromatherapy (Gattefosse, 1993). Additionally, its anticonvulsant properties have been linked to suppression of potassium-stimulated glutamate release in cortical synaptosomes as well as antagonistic effects on certain cell receptors (Elisabetsky, 2002). Linalyl-betaglucopyranosidine (2) is found in flower buds of Jasminum as aroma precursors of linalool monoterpenes. Benzyl acetate (3), another important aromatic compound, is an organic ester formed from the condensation of benzyl alcohol and acetic acid. Like most other esters, it possesses a pleasant and sweet aroma and thus finds applications in personal health care products and aromatherapy. Benzaldehyde (4) is an aromatic aldehyde with only one formyl group and an almond scent. Benzaldehyde is composed of benzene with a single formyl group. It is the smallest aromatic aldehyde and the parent of the benzaldehyde class. The liquid form of benzaldehyde is transparent, colorless to yellow, and it smells like bitter almonds. Although it is heavier than air and is denser than water, it is insoluble in water and thus used to create fragrances and flavors. Benzaldehyde is used in the chemical industry frequently to create different aniline colors, fragrances, flavorings, and medications. Benzyl alcohol (5) is an aromatic alcohol occurring in nature up to 6% in the flowers of jasmine spp. It possesses antimicrobial and preservative properties at concentrations ranging from 0.9% to 2.0% (Corcoran and Ray, 2014). Its derivative, benzyl acetate, is a major component of jasmine oils. Geranyllinalool (6) is a tertiary alcohol diterpenoid; that is, a linalool in which one of the terminal methyl hydrogens is been substituted by a geranyl group (the 6E,10E-geoisomer). It possesses the dual properties of a metabolite, a fragrance-enhancer and as an (serine C-palmitoyltransferase) inhibitor and an insecticidal the defensive mechanism against some termites (Reticulitermes species) at lethal doses of LD50 (Lemaire et al., 1990). Eugenol (7) is a bioactive phenylpropanoid molecule found in many plants, notably jasmine, where it is a primary aromatic component and also the most effective chemical (Taleuzzaman et al., 2021). Antioxidant, antibacterial, anti-inflammatory, anesthetic and neuroprotective effects are all recognized for this molecule. Eugenol is produced from guaiacol, which is made up of phenol and a methoxy group in the ortho position (NCBI, 2021). Methyl jasmonate (8) is another volatile organic compound that is an ester of jasmonate methyl; the methyl ester of jasmonic acid found in plants. It functions primarily as a plant defense and in several developmental pathways including seed germination, root growth, flowering, fruit ripening and senescence, as well as in plant stress responses, growth, and

164

7. Jasmine essential oil: Production, extraction, characterization, and applications

development. S-adenosyl-L-methionine: jasmonic acid carboxyl methyltransferase catalyzes the production of methyl jasmonate with decarboxylation being the most likely pathway to the creation of volatile cis-jasmone (Christie, 2014). Methyl linoleate (9) is a fatty acid methyl ester of linoleic acid discovered as a plant metabolite from Neolitsea daibuensis. Linoleic acid on the other hand is an essential fatty acid and a precursor to arachidonic acid that plays role in the synthesis of some prostaglandins (Whelan and Fritsche, 2013). cis-Jasmone (10), Indole (11), benzyl benzoate (12) and cadinol (13) are key compounds that play significant roles in the fragrance and aromatic properties of jasmine EO. Indoles (11) in particular are widely heterocyclic ring systems with several uses in pathophysiological diseases such as cancer, microbial and viral infections, inflammation, depression, migraine, hypertension, and so on. Indoles are derivative of shikimic acids and are a broadly occurring functional group in nature found in an expansive number of bioactive natural products and pharmaceutical compounds. Since the shikimic acid pathway is responsible for the synthesis of many of the phenolic compounds in and the aromatic amino acids phenylalanine, tyrosine, and tryptophan (Sell, 2010), it is plausible that these amino acids contribute to the aroma and fragrance of the jasmine EO. Because tryptophan has an indole nucleus, it is commonly found in phytoconstituents such as fragrances, neurotransmitters, auxins (plant hormones), indole alkaloids, and so on. Indoles are good candidates for therapeutic discovery because of their intriguing molecular architecture (Chadha and Silakari, 2018). Farnesene (14) occur in essential oil as alpha-farnesene or cis-beta-farnesene. It is a major aroma and flavor compound found in jasmine essential oil. In the biosynthesis of a sesquiterpene, farnesol is first formed from isoprene which is formed from the reaction between geranyl pyrophosphate and isopentenyl pyrophosphate to form the intermediate 15-carbon farnesyl pyrophosphate (Fig. 7.5). Oxidation of the later can then result in sesquiterpenoids such as farnesol. Methyl anthranilate (15), another key jasmine aromatic component, is a derivative of anthranilic acid occurring as methyl ester of benzoate. It is a colorless to pale green-yellow liquid, with fruity aroma,

FIG. 7.5 Biosynthesis of farnesene. NCBI, 2021. PubChem Compound Summary for CID 445995. National Library of Medicine, National Institutes of Health, Bethesda, MD, USA. Retrieved July 1, 2021 from: https://pubchem.ncbi.nlm.nih. gov/compound.

7.6 Applications of jasmine essential oil: Pharmacological, agrofood, and nonfood applications

165

insoluble in water but soluble in benzene, pet ether, and slightly soluble in ethanol. It is used as flavoring, fragrance component, perfuming and masking agent. There has been no report of safety concern at current levels of intake when used as a flavoring agent.

7.6 Applications of jasmine essential oil: Pharmacological, agrofood, and nonfood applications Jasmine essential oil is among the notable oils that showed diverse biological and therapeutic potentials mainly contributed by its phytochemical compositions such as benzyl acetate, linalool, benzyl alcohol, indole, α/β-farnesene, among others. For example, benzyl acetate and linalool present are the key ingredients that conferred a typical characteristic scent of jasmine essential oil; while caryophyllene and its derivatives are responsible for its spicy properties (Ye et al., 2015). The major factors affecting the wider applications and usage of jasmine oil include its exorbitant costs, unavailability, and low extraction yields (Holmes, 1998). Ancient Chinese and Ayurvedic medicine shows that jasmine oil has a prominent position when it comes to aromatherapy. Thus, direct application of this oil by massaging it on the skin or through inhalation has been reported to cause soothing effect on human health, cognitive ability, and mood. Jasmine has been reported by Tiran (2000) to be among the commonly used essential oils to sooth anxiety and depression linked to pregnancy and childbirth. Similarly, antidepressant property of this oil has been reported by Sayowan et al. (2013) which indicated a significant rise in activity and strength with no signs of drowsiness. Jasmine oil possesses an exotic smell which aids in boosting confidence and optimism and its application during child birth is associated with increased uterus contraction and reduced pains. Other functions exhibited by this oil include combating depression postnatally and stimulating the flow of breast milk (Battagla, 1998). Antibacterial and antifungal potentials of jasmine oil were attributed to the presence of linalool which found different applications in the formulation of toothpaste, mouthwashes, candies, and food preservatives (Ahmed et al., 2016). When compared to the control group (Hongratanaworakit, 2010), topical application of jasmine oil on the belly skin had a significant influence on breathing rate and hemodynamic parameters (systolic and diastolic blood pressure, heart rate, and arterial blood pressure). The findings further showed autonomic stimulation in the tested volunteers together with high level of alertness, energy, and enthusiasm which could serve as possible reasons for its utilization in aromatherapy to ease depression and elate mood in humans. Similarly, Arun et al. (2015) showed that raised beta waves were recorded in the brain of individuals that inhaled jasmine oil scent which was linked to their increased alertness and attentiveness. Jasmonoid (a constituent of Jasmine oil) is one of the favorite scents in perfumes and fragrance ingredients used in household products formulation. Effect of jasmine oil message was monitored on females that were clinically diagnosed for about 2 years to have intermittent spike wave burst in their electroencephalogram which was further aggravated by difficulty in sleeping and hunger. There was significant reduction following jasmine oil massage at first instance in spike-wave flow in the patients and subsequent treatment resulted in complete disappearance of the spike-wave activity in electroencephalogram (ECG) for more than 30 days (Howes et al., 1998).

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7.6.1 Antimicrobial potential Generally, the bioactive constituents present in any compounds, solvents used for extraction procedures, nature of the microbial species to be tested, presence of solubilizers and emulsifiers, incubation period, temperature, and pH as well as microbial inoculum is the key factors affecting the efficacy of antimicrobial activity of any substances (Nazzaro et al., 2013). Strong antimicrobial activity had been reported in essential oils whose major compositions include aldehydes and phenols while high proportion of ketones, esters, or terpene hydrocarbons in essential oils conferred weaker antimicrobial activity (Bassole and Juliani, 2012). With minimum inhibitory concentrations (MIC) ranging from 1.9 to 31.25 L/mL, jasmine oil showed antibacterial activity against antibiotic-resistant Escherichia coli (MTCC-443). As a result, MIC is a reliable assay for determining the minimal quantity of any test drug necessary to slow down observable microorganism growth (Rath et al., 2008). The oil was suggested by Rath et al. (2008) to exert its effect based on its inhibitory potential on E. coli cell membrane synthesis. Generally, gram negative bacteria tend to tolerate lipophilic compounds more than gram positive ones and this could be attributed to the longer time taken for the essential oils to exert their inhibitory potential in them (Mangalagiri et al., 2001). However, Jasmine oil showed quick inhibitory response when tested on antibiotics resistant E. coli. The MIC of jasmine oil against clinical isolates of Candida albicans is 500 g/mL; strongly inhibiting the formation of candida biofilms among four out of six isolates. It also showed a promising antifungal potential due to its ability to further inhibit virulence factors linked to phospholipase activity and hemolysin production which are attributed to its bioactive constituent, 2-phenylthiolane (El-Baz et al., 2021). When jasmine oil was tested against Trichosporon ovoides, it had a lower MIC value of 3.1 g/mL than Imidazole (50 g/disc) and Nystatin B (100 g/disc), which had MIC values of 12.5 and 6.2 g/mL, respectively (Saxena et al., 2012). The antimicrobial activity of 53 essential oils were tested using different pathogenic organisms such as E. coli, P. aeruginosa, C. albicans, B. subtilis, and S. aureus by Janssen et al. (1986). They discovered that essential oils had bacteriostatic and bactericidal effects on motile and sessile gram-positive and gram-negative bacteria in varying degrees. Jasmine oil has been found to work as a natural antibacterial agent against a variety of clinical and nonclinical isolates as indicated in Table 7.2; suggesting its potentials to be used in preventing and/or treating infections caused by the tested organisms. Another unique feature of jasmine oil is its application as facial cleanser whose major role involves elimination of dirt and other undesirable substances from human skin. Different cleansers are being developed based on their additional advantages such as acne therapy, humectant formulation and skin soothing effect which contribute more to its wider production, popularity and to some extent its acceptance. Phuc et al. (2019) developed a facial cleanser which when tested on 30 volunteers, showed that the presence of jasmine oil contributed in maintaining the pH of 6.78, viscosity of 16,100 mPa s with high ability of removing dirt and moisturizing the skin and no side effects associated with irritation and dryness were reported. In order to retain the fragrance and minimize the high volatility of essential oil, the use of polymethyl methacrylate as a binder or a stabilizer to encapsulate jasmine oil was studied by Teeka et al. (2014) based on developing an oil-water emulsion system followed by evaporation process and this led to an encapsulation efficiency of 72%. The target of encapsulation is to increase and prolong the bioactivity of the essential oil such as antioxidant, antibacterial, and preservative potentials.

7.6 Applications of jasmine essential oil: Pharmacological, agrofood, and nonfood applications

TABLE 7.2

167

Antimicrobial activity of Jasmine oils against clinical and reference strains of different organisms. Zone of inhibition (mm)

Minimum inhibitory concentration (%)

References

Propionibacterium acnes CMCC 65002

7.5

0.5

Zu et al. (2010)

P. acnes DMST 14916

12.8  0.6

2

Luangnarumitchai et al. (2007)

P. acnes DMST 14917

12.0  1.2

2

P. acnes DMST 14918

11.3  0.8

2

Enterococcus faecalis (Clinical isolate)

10

0.06

Klebsiella pneumoniae (Clinical isolate)

10

0.06

Escherichia coli ATCC 8739

7

0.06

Pseudomonas aeruginosa (Clinical isolate)

23

1

Staphylococcus aureus (Clinical isolate)

25

8

Streptococcus pyrogenes (Clinical isolate)

41

0.5

Salmonella enterica CIP 105150

31

1

Shigella dysenteria CIP 5451

29

1

Candida albicans (Clinical isolate)

13

0.5

Abdoul-Latif et al. (2010)

C. albicans ATCC 10231

8

0.006

Jirovetz et al. (2007)

C. krusei ATCC 6258

26

0.19

Thaweboon et al. (2018)

C. parapsilosis ATCC 22019

17

0.39

C. tropicalis (Clinical isolate)

10

0.78

C. stellatoidia (Clinical isolate)

20

0.19

Microorganism Bacteria

Jirovetz et al. (2007)

Abdoul-Latif et al. (2010)

Fungi

7.6.2 Antioxidant and anticancer potential Jasmine oil contains a variety of phytochemically active compounds with reported health potentials including antioxidant properties. Thus, antioxidants are substances that have ability to inhibit, slow down or put off oxidative damage by removing the damaging effects of free radicals on macromolecules (lipids, DNA, and proteins) and neutralizing any stages of oxidative chain reactions (Khidzir et al., 2015). Wang et al. (2017) conducted extensive research

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into the antioxidant potential of 26 essential oils using the total phenolic content, potassium ferricyanide assay, β-carotene bleaching assay, ABTS (2,20 -azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) assay, and the DPPH (1,1-diphenyl-2-picrylhydrazyl) assay. Clove bud and jasmine absolute essential oils had strong radical scavenging potentials of 94.13%  0.01% and 78.62%  0.01%, respectively, among the essential oils. Jasmine oil (299.60 mg/mL) had a lower EC50 value than Vetiveria zizanioides (7790 mg/mL), Zataria multiflora (2220 mg/mL), and thyme borneol oil (655.45 mg/mL), but was higher than clove bud oil (7.81 mg/mL), cinnamon bark (53 mg/mL), origanum (36 mg/mL), and Petitgrain mandarin (79.84 mg/mL). Clove bud (94.58%  0.11%), thyme borneol (83.87%  0.10%), rose flower (79.10%  0.08%), and jasmine absolute (71.48%  0.01%) are the essential oils with the highest β-carotene bleaching activity. ABTS assay showed a good potential for jasmine oil with a trolox equivalent of 354.56  0.01 mM compared to 186.78  0.01 mM and 159.00  0.01 mM found in chamomile and thyme borneol oils, respectively. Based on these, jasmine oil could be utilized in the formulation of cosmetics and functional foods. When compared to a standard, jasmine oil exhibited an IC50 value of 7.43 g/mL with relative antioxidant activity of 96.6% when antioxidant activity was determined using DPPH free radical scavenging and -carotene bleaching tests (2,6-di-tert-butyl-4-methylphenol) (Abdoul-Latif et al., 2010). The aldehyde/carboxylic acid assay was used to test the long-term antioxidant activity of 13 essential oils at a concentration of 500 g/mL; after 40 days, full suppression (100%) of hexanal oxidation was found in jasmine oil, rose oil, and parsley seed oil. Similarly, 90% DPPH scavenging activity was recorded in jasmine oil which was found to be higher than the control (α-tocopherol) whose activity was found to be 86% (Wei and Shibamoto, 2007). Cytotoxicity study was carried out by Manjunath and Mahurkar (2021) on three cell lines (A431, MKN-45 and U-87 MG); and jasmine oil exhibited significant cytotoxicity on A431 and U-87 MG with an IC50 values of 99.86 and 336.2 μg/mL, respectively. In case of anticancer activity, jasmine oil at 1000 and 250 μg/mL was found to have higher activity on A431 and U87-MG cell lines when compared with the control (5-fluorouracil). Thus, lower concentration of jasmine oil of 125 μg/mL had significant effect on gastric cancer cell line (MKN-45).

7.6.3 Acaricidal potential The economic loss associated with infestation of two-spotted spider mite was studied in egg plants using three essential oils i.e., mustard oil, jasmine oil, and lavender oil. Higher acaricidal effect was observed in jasmine oil at 2.5 mL/L which resulted in significant reduction rate of 49.03% in the pest population with an efficiency value of 68.50% compared to the reduction rate of 19.34% and efficiency value of 50.2% recorded in lavender oil (Farouk et al., 2021). Jasmine oil could serve as a potential acaricidal agent based on its efficiency value as two-spotted spider mite tend to resist most of the conventional pesticides which is the major challenges encountered during the treatment. Similarly, the bioactive constituents of essential oils including jasmine oil exert some inhibitory or regulatory role on arthropods which make to be suitably used as acaricides. Blenau et al. (2012) and Ebadollahi et al. (2017) found that essential oils’ acaricidal ability is connected to their interaction with several receptors and

7.6 Applications of jasmine essential oil: Pharmacological, agrofood, and nonfood applications

169

targets, including tyramine and octopamine receptors, acetylcholinesterases, phosphate hydrolases, oxygenases, and transferases. Thus, application of jasmine oil further improved eggplant growth, photosynthetic pigment, chlorophyll a:b ratio, vitamin C and phenol contents (Farouk et al., 2021).

7.6.4 Xanthine oxidase inhibitory activity Higher uric acid concentration in the body causes hyperuricemia and xanthine oxidase is an important enzyme that increases excretion of uric acid or decreases its production. Gout is one of the inflammatory arthritis associated with deposition of uric acid crystals in the joints; jasmine oil was reported to have xanthine oxidase inhibitory potential when compared with the standard drug Allopurinol. In vitro studies showed 97% and 82% inhibition by Jasmine oil and Allopurinol, respectively, at 0.5 mg/mL suggesting that jasmine oil has better antioxidant potential via reduction of oxidative stress and decrease in concentration of circulating uric acid than the standard drug (Pushparathna et al., 2020).

7.6.5 Food preservation potential The two important components (Jasmonic acid and methyl jasmonate) present in jasmine oil bestow it with the ability to minimize chilling injury through expression of defense genes that favor the release of abscisic acid and polyamines which ultimately enhance its antioxidant potential. Chilling damage has been identified as one of the key problems of utilizing refrigeration to preserve and prolong the shelf life of diverse farm produce (Hamdy et al., 2015; Wang, 2006). For example, cucumber is among the chill-sensitive fruits that cannot be stored even under refrigerated condition for longer periods. Rageh and Abou-Elwafa (2017) studied the combined effect of jasmine oil and yeast extract on chilling injury and shelf life of cucumber fruits; the findings showed that addition of either 2 and 4 mL/L of jasmine oil in the presence of dry yeast (10–20 g/L) significantly reduced the chilling injury and extend the shelf life at 5°C for 12 days without any alteration in the fruit firmness, color and weight loss throughout the study period. Similarly, components of jasmine oil with specific reference to methyl jasmonate cause an increased expression of ethylene synthesis thereby promoting ethylene production. Rudell et al. (2002) showed that application of jasmonate to apples favors increased color formation and build-up of β-carotene and anthocyanins; while in berries, a remarkable increase in titratable acidity and sugar contents were observed. Different treatments using jasmine oil and its combination with gibberellic acid were carried out on Ruby seedless grapevines and the results showed that spraying of jasmine oil alone was better in terms of total soluble solids, reducing sugar, total acidity, and soluble solid/titratable acidity ratio of 19.80%, 16.60%, 0.463%, and 42.74%, respectively (El-Akad et al., 2021). Although jasmine oil and jasmonate treated fruits retained higher sugar and organic acid contents; the findings of Gonzalez-Aguilar et al. (2003) showed that Carica papaya lost its firmness during storage and became highly deteriorated at 20°C due to prior exposure of jasmonate vapor to the fruit for 16 h.

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7.7 Safety, toxicity, and regulations There is consensus that essential oils extracted from natural sources devoid of any modifications or presence of additives are generally regarded as safe (GRAS). As a result, the US Food and Drug Administration (FDA) and the European Commission have approved and recognized numerous essential oils for usage as additives in the manufacture of home and other associated goods (Chen et al., 2020). However, many countries do not have stringent regulations on the use and application of essential oils as such no recommendation is set for acceptable daily intake. Excessive use of essential oils, however, has been linked to negative side effects in several studies; for example, Uter et al. (2010) discovered that lavender, jasmine, and clove essential oils might induce allergic responses when used often. In vitro studies indicated some degree of damage incurred on cell membranes exposed to the essential oils. Thus, essential oils especially in their concentrated forms are better applied externally due to the possibility of causing skin irritation and damages to soft tissues such as mucous membrane, stomach lining, among others (Devi et al., 2015). According to Hammer et al. (2006), any adverse effects of essential oils can be prevented by diluting the oil for topical use, proper storage conditions, and avoiding direct ingestion. Eisenhut (2007) reported that most of the toxicity of essential oils are alluded to hypersensitivity of individuals as so far, no serious injury or toxicity that cause convulsion, stomach upsets, nausea, vomiting and any dysfunctions linked to kidney and central nervous systems. However, efficacy and safety of essential oils are greatly compromised when stored improperly due to possible oxidation and peroxidation of lipids, rancidity, and other unwanted side reactions associated with alcohols and ketones (Sarkic and Stappen, 2018). Jasmine oil is among the essential oils approved by US FDA to be used as flavorant, and recommended quantities are required to ensure that the developed product is safe for utilization (US FDA, 2018). However, through its development and sustainability plans, REACH (Registration, Evaluation, Authorization, and Restriction of Chemicals) regulations (EC No 1907/2006) reiterated that safety to human health and environment should be prioritized for all chemicals used in products formulation or imported into any country in large quantities. This regulation excludes many compounds including essential oils and those within country’s customs control. Thus, CLP (Classification, Labeling, Packaging) regulation (CE) N. 1272/2008) is the one that is applicable to all essential oils which became effective on 1st June 2015 and has the following key objectives: i. To assess the compositions of any substance so as to classify it accordingly. ii. To boost the end user’s confidence by not posing significant threats to human and environment. iii. To ensure uniformity in terms of classification, labeling, and packaging. iv. To come up with unified criteria for shipment of these substances. v. To develop catalogues that meet the specifications set in the UN classification of chemicals. vi. To enable free exchange of these substances or their mixtures with adherence to EU regulations.

7.8 Trade, storage stability, and transport

171

Since essential oils including jasmine oil are used as flavorants, and as additives in feed and cosmetic formulations, then Regulation (EC) No 1334/2008 Article 4 specifies that for any substances to be used as such let there be scientific evidence on their compositions confirming their safety without misleading the consumer. The document further confirmed in Article 20 that monitoring and evaluation systems need to be put in place for feedback and information dissemination to the concerned agencies (Barbieri and Borsotto, 2018).

7.8 Trade, storage stability, and transport Around 200 distinct types of essential oils are believed to be produced worldwide, with yearly production volumes ranging from 30,000 tons for orange oil to 0.1 tons for jasmine, rose, and lavender oil (Wei and Shibamoto, 2007). Depending on the demand and applications, wider variations in the market price for most of the essential oil traded in volumes were within US$4–$60/kg; however, some specialized oils could even be higher than $100/kg (Green, 2002). Reliable global statistical data on the quantity of essential oils produced or traded is often difficult to come by as several countries have no documentation of their domestic production and solely depend on the export statistics. France is the biggest importer of essential oils in the EU, with a total value of $65 billion dollars, followed by Germany ($41 billion dollars) and Ireland ($35 billion dollars). Overall, the United States ranks #1 in the world in terms of essential oil exports (Green, 2002). Similarly, China, India, Egypt, Indonesia, Sri Lanka, and Vietnam are the top producers of essential oils, and their contributions to market expansion have been significant. Other sections of the world, such as the North American continent, Africa (particularly Egypt, Morocco, Tunisia, and South Africa), and Eastern Europe, have also made significant contributions (Barbieri and Borsotto, 2018). Thus, the major players will continue to retain their prominence due to the level of awareness and increased acceptance of natural and organic formulations containing essential oils. According to the Netherlands Ministry of Foreign Affairs’ Centre for the Promotion of Imports from Developing Countries (https://www.cbi.eu/market-information/natural-food-additives/essentials-oils-food), the global market for essential oil has grown dramatically since 2014 (US$ 5.51 billion) and is expected to reach US$ 11.67 billion in 2022 (https://www.cbi.eu/market-information/ essentials-oils-food). Thus, The International Federation of Essential Oils and Aroma Trades (IFEAT), a nonprofit organization that promotes the use of essential oils and trade, indicated that more than 50% of global supply of jasmine oil comes from Egypt, and the country earns up to $6.5 million yearly, where jasmine related trades provide job opportunities (especially in Fakhry essential oils factory and its affiliates) to more than 50,000 people. Statistics showed that 400 ha of lands are currently in use for production of scented plants and daily picking of jasmine flowers amounted to 20 tons (https://www.africanews.com/2020/08/25/egypt-strade-in-fragrant-jasmine-flowers-on-the-hike//). The European Federation of Essential Oils showed the market share of essential oils based on various applications ranked food and beverage to be the highest with 35%, followed by 29% as the share for fragrances, cosmetics, and aromatherapy, whereas 16% and 15% are for household and pharmaceutical applications, respectively (Barbieri and Borsotto, 2018). The data obtained from USDA Marketing Directorate

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showed that the United States, Western Europe, and Japan have the greatest percentages of essential oil users at 40%, 30%, and 7%, respectively (http://www.fao.org/3/ax257e/ax257e. pdf). Specific gravity, optical rotation, refractive index, and gas chromatographic tests, according to Devi et al. (2015), are crucial in determining the quality of jasmine oil. Proper storage of jasmine essential oil determines its shelf life, safety, and bioactivities which are often influenced by storage temperature as well as vessel used. Oxidation, peroxidation, and polymerization are the unwanted reactions that occur in essential oil due to prolonged exposure to sunlight and air as such essential oils are better stored in amber glass bottles aluminum bottle and drums (Devi et al., 2015). Jasmine oil can be preserved for 3–7 years if properly stored, and it is believed that adequate drying of the oil will be required prior to storage for transportation. Filtration, anhydrous calcium sulfate, and nitrogen gas filling of the head space are all advised. Because of its capacity to react with moisture to generate carbonic acid, which causes rapid deterioration of essential oils, carbon dioxide can also be used in place of nitrogen gas with caution (http://www.fao.org/3/ax257e/ax257e.pdf). Depending on the nature of the oil, however, deterioration may result in darkening, lightening and complete loss of color, increase or decrease in aroma, thickening and changes in consistency and muddy appearance of the essential oils (Devi et al., 2015). It has been a recommended practice by producers of essential oils including jasmine oil that prior to bulk purchase a sample is first supplied to the intended buyers indicating all the production specifications for proper evaluation and testing, and, upon meeting the requirements by both parties, a full order is made accordingly. Proper labels and seals to prevent leakages must be put in place.

7.9 Conclusion Benzyl acetate, linalool, benzyl alcohol, indole, α/β-farnesene are among the bioactive chemicals found in Jasminum sp. Jasmine oil is a volatile odoriferous oil derived from Jasminum sp. The plant belongs to the Oleaceae family, and its cultivation is best suited to the tropical and subtropical regions of the world (Asia, Africa, and Australia). Oil extraction from jasmine blossoms has been done using a variety of processes, including steam distillation, solvent extraction, and oil and fat-based extraction (enfleurage and pneumatic). Recently supercritical gas extraction is preferred due to its ability to prevent the loss of heat and water labile compounds so as to overcome the major disadvantages of hydro-distillation and solvent extraction. The quality of essential oils, especially Jasmine oil, is commonly assessed using specific gravity, optical rotation, refractive index, and gas chromatographic tests. Jasmine oil deteriorates quickly when exposed to air and sunshine for an extended period of time, which can be mitigated by using dark tinted glass containers and storing it at a low temperature. Reports consider jasmine oil as one of the GRAS (generally regarded as safe) oils which is widely used as an antidepressant with ability to relieve stress, anxiety, strain, and pain. The antimicrobial activity has been tested on various clinical and reference pathogenic bacterial and fungal strains, where jasmine oil proved effective in exerting static and cidal effects. Inhaling the smells of jasmine oil enhances the brain’s beta waves, which are connected to greater alertness and attentiveness. Jasmine oil’s free radical scavenging action has been

References

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lauded since it was discovered to be comparable to that of common reducing agents like ascorbic acid, tocopherol, and carotenoids. The bioactive constituents of jasmine oil contributed to its acaricidal potential with strong ability to reduce different plant pest populations. Similarly, prolonging the shelf life and minimizing chill injury associated with fruit and vegetable storage could be possible using jasmine oil. The use of jasmine oil as an additive in the manufacture of home and other associated products is permitted by the US Food and Drug Administration (FDA) and the European Commission. Most countries do not have any regulations on the use and application of essential oils as such no recommendation is set for acceptable daily intake. However, excessive application may cause allergic reaction on skin and other soft tissues. The main supply of jasmine oil originates from Egypt, according to the International Federation of Essential Oils and Aroma Trades (IFEAT), and the country generates up to $6.5 million annually from jasmine-related trades. Proper storage needs to be put in place to prevent the deterioration of jasmine oil which could cause its darkening, lightening and complete loss of color; increase or decrease in aroma, thickening and changes in consistency and muddy appearance.

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C H A P T E R

8 Citrus essential oil (grapefruit, orange, lemon) Gurpreet Kaura, Kamalpreet Kaurb, and Preeti Salujac a

Department of Zoology, Mata Gujri College, Fatehgarh Sahib, India bDepartment of Chemistry, Mata Gujri College, Fatehgarh Sahib, India cDepartment of Chemistry, RKMV, Shimla, Himachal Pradesh, India

8.1 Introduction Citrus fruits are one of the valuable crops with an annual production of about 100 million tons worldwide (FAO, 2016; USDA, 2020). A huge portion of citrus fruits is found in Asia (44%), South America (18%), and Europe (20%) (Mahato et al., 2019). Citrus fruits are employed chiefly for juice production in the food processing industry. During food processing, these industries produce approximately 54 million tons of citrus waste worldwide which chiefly contained inedible citrus peel waste (Mahato et al., 2019). Thus, it is very crucial to manage the number of citrus peels from an ecological point of view (Martı´n et al., ´ ngel Siles Lo´pez et al. (2010); Zema et al., 2018). In this aspect, the peels are subjected to 2018; A incineration, ground dumping, or composting. Moreover, peels are used for the production of animal feed and pectin (Martı´n et al., 2018). However, numerous aspects restrict the potential of peel waste of citrus for composting. It contains less quantity of nitrogen which hampers the rate of decomposition. Many bioactive components present in citrus peels cause the degradation of soil microorganisms owing to their antibacterial characteristics. In addition to it, antinutritional properties, low pH, and exorbitant price limit the wide use of citrus peel as animal feed (Ani et al., 2015; Teigiserova et al., 2020; Martı´n et al., 2018; Mahato et al., 2019). Further investigations are going on to scrutinize the citrus peel waste for the isolation of bioactive products (Teigiserova et al., 2020; Zema et al., 2018). It was found that citrus peel waste consists of a wide range of phytoconstituents such as limonene, carotenoids, flavonols, lignins, fibers, sugars, hemicellulose, ascorbic acid, pectin, phenolics, and essential oils (Sharma et al., 2017; Rezzadori et al., 2012). Fascinatingly, the essential oil is the utmost imperative derivative of citrus processing. Essential oil of citrus is authorized as food

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supplement in numerous food products due to its safety profile (Tisserand and Young, 2013; Ferhat et al., 2006). The citrus essential oil shows many medicinal and pharmacological properties which include its ability to control the infection against pathogens like fungus, bacteria, and protozoans like Leishmania. Essential oil of Citrus fruits has been found to behave as antioxidants and is anticancerous. There is a large body of literature illustrating the antimicrobial activity of essential oil in citrus fruits. These biological activities are believed to be due to the more concentration of active compounds like flavonoids, terpenes, carotenes, and coumarins in the citrus oil (Viuda-Martos et al., 2008; Roberto et al., 2010; Ali et al., 2017; Yu et al., 2017). Essential oils of citrus are exploited for their invigorating smell as well as flavor and numerous aromatherapeutic and pharmaceutical applications (Dosoky and Setzer, 2018). These natural citrus oils progressively replace the synthetic compounds in the food industry because of more consumer satisfaction. The essential oils of orange, lemon, and grapefruit hampered the multiplication of few bacteria in the food industry like Staphylococcus carnosus, Lactobacillus curvatus, and S. xylosus and also inhibited the microbes related to food putrefaction such as Enterobacter gergoviae and E. amnigenus. Moreover, the nanoemulsions of essential oil of citrus fruits displayed remarkable antimicrobial, antioxidant, and antibiofilm activities (Zhang et al., 2019). Several researches studied the phytoconstituents of essential oil of leaf, flower, and peel of various citrus species because of their more economic importance. The phytoconstituents of citrus oils showed marked variation because of alterations in source, genetics, maturation stage, environment, extraction method, etc. (Dosoky et al., 2014, 2016; da Silva et al., 2017). Essential oils of orange and grapefruit contain a major part of monoterpenes (Tisserand and Young, 2014). The chief constituents of orange leaf essential oil are linalool and linalyl acetate (De Pasquale et al., 2006), however, the citrus essential oil consisted of maximum linalool, followed by linalyl acetate and limonene (Haj Ammar et al., 2012).

8.2 Extraction and characterization of citrus essential oils (CEOs) The methods employed for the extraction of essential oils (EOs) are mainly governed by their energy requirements, carbon dioxide emission, and the cost of the extraction process. The approach used for extraction should be capable of managing waste, removing bye products as vapors, and producing extraction products efficiently (Sharma et al., 2017; Raimondo et al., 2018). Citrus fruits are considered commodity products such as coffee and tea. The food industries process about 30% of citrus fruits (including limes, lemons, oranges, tangerines, and grapefruits) each year worldwide and generate plenty (approximately 19 million tons annually) of citrus peels as waste. The citrus peels yield about 4% citrus essential oil (CEO) which is used as a fragrance in body-care products for its refreshing aroma. The major components of citrus essential oils include compounds such as terpenes, esters, alcohols, aldehydes like citral and D-limonene (Shaw, 1979). D-Limonene is the major component of orange peel oils (90%–95%) and lemon peel oils (75%). Limonene performs a vital part in flavors and fragrances and finds applications in many consumer products (Angel Siles Lopez et al., 2010). The conventional methods usually employed for the extraction of Eos, viz., maceration, solid–liquid extraction (SLE), soxhlet extraction, infusion, and liquid–liquid extraction (LLE), suffer from the limitation of being lengthy, requiring more energy, and using noxious

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solvents. Moreover, the conventional extraction processes generally take place at higher temperatures and may decompose the heat-sensitive components of EOs (Shirsath et al., 2012). Therefore, the interest in green and benign alternatives of extraction is increasing day by day. The nonconventional and green alternatives of extraction of EOs include supercritical fluid extraction (SCE), microwave-assisted extraction (MAE), steam explosion, ultrasoundassisted extraction (UAE), and enzyme assisted extraction (EAE) not only need lesser solvents and time but also produce EOs in enhanced yields and better-quality (Panda and Manickam, 2019). MAE and UAE are the most extensively employed methods of extraction for EOs from citrus plants owing to the ease of the extraction process and lesser energy demands. Ionic liquids (ILs) also act as green solvents because of their distinct properties like noninflammability, broad liquid range, nonvolatility under usual processing conditions, thermal and chemical stability, insignificant vapor pressure, and ability to dissolve a large number of compounds. Therefore, ILs can be effectively exploited as solvents for the extraction of EOs and other valuable products from plants like alkaloids, lignans, phenols, glycosides, and organic acids. They can form emulsions in water and thus can behave as surfactants for extracting hydrophobic essential oils. Deterpenation of CEOs (combination of hydrocarbons with terpenes and terpenoids as major components) is very important for enhancing the stability and quality of the final products required for their practical applications in the cosmetic, pharmaceutical, or food industry. Presently, alternative solvents like ionic liquids (ILs) which could replace harmful organic solvents mostly used in extraction processes are crucial for sustainable deterpenation of CEOs. Water is generally used as a solvent in the MAE process owing to its microwave absorbing capacity and easier removal from the final products due to its immiscibility in EOs. ILs can absorb microwave radiation easily and thereby enhance the efficiency of the extraction process due to their excellent solvation and dielectric properties (Yang et al., 2012). In ionic liquid-based microwave-assisted extraction (MAE-IL), essential oils are retrieved in the vapor phase along with water and are devoid of ionic liquids. Supercritical fluid extraction (SCE) has the advantages of being noninflammable, nontoxic, and operating at moderate/low pressure and temperature without producing any chemical residue. The hybrid techniques utilizing the blend of the ultrasound-assisted extraction (UAE) with microwave-assisted extraction (MAE), supercritical fluid extraction (SCE), instant-controlled pressure drop technique (DIC), extrusion extraction (Chemat et al., 2017), and microwaveassisted hydrodistillation (MAHD), microwave-assisted hydrodiffusion and gravity (MHG) (Bousbia et al., 2009) method prove to be more advantageous and promising solvent-free techniques for the extraction of EOs from citrus plants. Moreover, extraction methods based on cavitation not only increase the quality and yield of the extraction process but also allow quick extraction. The most commonly used cavitation-based extraction methods are negative pressure cavitation (NPC), UAE, and hydrodynamic cavitation (HCE). The hydrodynamic cavitation method is based on passing a liquid across an orifice/venturi where the kinetic speed is enhanced at the expense of pressure (Holkar et al., 2019). When the pressure falls below the vapor pressure, a cavity is formed in the orifice/venturi which further collapses on recovering the pressure and results in the formation of hotspots. This extraction method is employed for isolating EOs from waste orange peels with increased efficiency, yield, and the possibility of scalability of the extraction process (Meneguzzo et al., 2019; Albanese and Meneguzzo, 2019). Furthermore, the solar hydrodistillation (SSD) method is a green zero-waste biorefinery alternative; utilizing solar energy for

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the extraction of EOs (Hilali et al., 2019). The important techniques employed in the isolation of EOs from citrus species (oranges, lemon, and grapefruits) have been described below.

8.2.1 Cold pressing (CP) method Cold pressing is the primitive oil separation technique (Karaman et al., 2015), in which the oils are discharged from the glandular part located in the peels by mechanical pressure (Ferhat et al., 2007; Mahato et al., 2019). The watery emulsion of the oil is centrifuged to get CEO. Since no heating is applied, the essential oil retains its aromatic properties. Quintero et al. (2001) used the simplest methodology of cold pressing for extracting essential oils from the cortex of Citrus aurantium (bitter orange). The compounds constituting the EO were analyzed by gas chromatography-mass spectrometry. The chief compounds prevailing in the oil were monoterpenes including limonene (77.90%), myrcene (1.81%), β-pinene (3.40%), and trans-ocimene (1.16%); valencene (0.52%); decanal (3.51%), dodecanal (0.36%) and geranial (0.29%), β-nerolidol (0.85%) and linalool (0.89%) and nootkatone. Cold pressing acts as an excellent method as no oxidation product of monoterpenes like p-cimene was found in the EO. No unpleasant odor was detected as terpinen-4-ol was present only in minute amounts in the EO. The bioactivity of orange essential oil was assessed using discs saturated with 20 μL of EO. The EO exhibited moderate activity (17 mm) against S. aureus and was inactive against Pseudomonas and E. coli. Ferhat et al. (2016) demonstrated extraction of essential oils from fresh citrus peels of four types of Algerian sweet oranges (Citrus sinensis), sour orange (Citrus aurantium), grapefruits (Citrus paradisi), citrons (Citrus medica), and tangelos by three different approaches of cold pressing (CP), hydrodistillation (HD) and microwave Clevenger also called microwave accelerated distillation (MAD) methods to draw a comparison in terms of their efficiency. The extracted EOs were characterized with the help of mass spectrometry and Kova´ts retention indices. Cold pressing (CP) was done by tearing the outer layer of oil glands with a needle to create regions of compression enclosed by lower pressure areas. The EO, so isolated, moves down into a decantation container and forms an emulsion with water which is separated by centrifugation in an automatic cold-pressing machine and is dried over a dehydrating agent (anhydrous sodium sulfate). Clevenger-type apparatus is used in the HD method to isolate EO from 200 g of fresh lemon peels in water (2L) for a duration of 3h. The isolated EO is then dried with anhydrous sodium sulfate and stored at low temperatures. MAD was carried out with the help of ’DryDist’ microwave oven by placing 200 g of fresh orange peels in a microwave reactor without any added solvent or water and were heated using a fixed power density of 1 Wg
1 at 100°C for 30 min. Consequently, the distillate was condensed to collect EO which was then dried over anhydrous sodium sulfate and stored at 4°C. The MAD process is different from modified microwave-assisted extraction (MAE) and modified hydrodistillation (HD). GC-MS analysis of all the extracted EOs indicated limonene (a monoterpene hydrocarbon) as the predominant component present in 86.69%–99.3% amounts. The comparison among the three extraction methods of CP, HD, and MAD was performed with the help of canonical discriminant analysis (CDA) and principal components analysis (PCA). The microwave accelerated distillation (MAD) method was found to be the most efficient method of extraction of EOs from citrus species because of shorter distillation times,

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lower energy requirements, solventless and cleaner extraction, better yields, and production of better quality EOs owing to the presence of larger amounts of oxygenated compounds.

8.2.2 Solvent extraction (SE) method Fekadu et al. (2019) used the solvent extraction method for extraction of EO from orange peel employing n-hexane, methanol, and petroleum ether as solvent. They took 10 g of orange peel powder possessing a particle size of 0.6 mm in the Soxhlet apparatus. The solvent evaporated in a heating mantle and consequently condensed down to pass through the sample to extract the EO. The yield of EO was calculated and was compared for different solvents used. The yield was maximum when n-hexane was used as a solvent. Hoshino et al. (2014) extracted EO from citrus fruits like ponkan which is commonly called Chinese honey orange and Yuzu called Japanese citrus lemon through a solvent extraction method. They used liquefied dimethyl ether (DME) as a solvent for extraction because of its many benefits over earlier used solvents. DME forms very weak hydrogen bonds with water, hence its solubility in water is very low. Thus, it does not require a distillation process for separation from water. Moreover, its nontoxic nature (Naito et al., 2005), vigorous dewatering capacity (Li et al., 2014), and ability to work at low temperature and pressure makes it a suitable solvent for EO extraction and to be used as a solvent in the food processing industry (Varlet et al., 2014). The sample consisting of peels of citrus was packed into the extraction column and glass beads were loaded at the top and bottom ends of the column (Kanda et al., 2012). Consequently, liquefied DME was passed through the extraction column at different time intervals to carry out extraction. The pressure-reducing valve was opened to allow the evaporation of DME and the leftover extract was equivalent to the total amount of essential oils and water extracted from the samples. When a comparison is made between the yield of essential oil extracted by using solvent extraction method and Steam distillation method, it was found that yield is lesser in the former case. The extracted EOs were not thermally degraded in the case of extraction with the solvent extraction method. Further, it was seen that the efficiency of extraction of EOs using the DME method also depends upon the thickness of citrus peel. The yield of EOs from the citrus peel with albedo part was 0.3 g whereas from citrus peel without albedo part was 3.4 g which depicted that the increment in thickness leads to a reduction in the yield of EOs.

8.2.3 Steam distillation (SD) method The extraction of essential oils from citrus peels can be carried out with the help of traditional methods of cold pressing and steam distillation (SD) (Sawamura and Kuriyama, 1988; Temelli et al., 1990). In the cold pressing method, a large quantity of essential oil is wasted as residues so the extraction yields are very poor (Suetsugu et al., 2013). SD can be used as an alternative to obtaining pure heat-sensitive essential oils by distilling the biomass at temperatures ranging from 130°C to 150°C. During the distillation step, the essential oils get evaporated with steam. The method is advantageous due to its faster and economical nature in comparison to other extraction techniques (Mercy et al., 2015). Hoshino et al. (2014) attempted dewatering and isolation of essential oils and flavonoids from the peels of Citrus tangerine and peel and leaves of Citrus junos by extraction with liquified DME and SD methods. SD was

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8. Citrus essential oil (grapefruit, orange, lemon)

carried out by distilling cut citrus peels of tangerine (50 g) with distilled water (500 mL) in a flask fitted with a Liebig condenser at atmospheric pressure for a duration of 4 h. During distillation, the essential oils got evaporated with steam and were collected in a container. Dewatering of the peels and leaves was carried out with liquified DME which removed 70%–80% of the water from the samples. The EOs have obtained 4.7% and 2.1% yields from the peels of Citrus tangerine and Citrus junos by employing the SD method. Moreover, the extraction yield by SD method and extraction by liquified DME was found to be similar. Sikdar et al. (2016) extracted essential oil from orange peels by steam distillation (SD) method. The SD process involves placing the pretreated orange peel in a distillation flask along with distilled water and heating the solution for 1 h by fixing the temperature at 88°C. The distillate so obtained is collected and is separated with the help of a separatory funnel. The less-dense layer of CEO is stored in an air-tight vessel. The effect of distillation time, solid to solvent ratio, and temperature on CEO yield was determined by keeping two parameters constant and changing the third one and the conditions were optimized. The maximum yield of citrus essential oil (2.4 mL per 100 g) of orange peel was obtained by carrying out the steam distillation process at 96°C for a duration of 1h and fixing the solid to solvent ratio as 100g/200 mL. Characterization of citrus essential oil (CEO) was established by gas chromatography (GC). D-limonene, α-pinene, β-mycrene, and octanol were identified as the main compounds of CEO present in 94.13%, 1.24%, 3.79%, and 0.84% respectively. In another study, Mercy et al. (2015) extracted essential oils from the peels of two different varieties of oranges: Citrus sinensis and Citrus reticulate, by using an improved steam distillation approach wherein the waste orange peels were preheated at 50°C for half an hour and then subjected to distillation process performed at 100°C for 120 min. The appearance of cloudiness in the distillate confirmed the presence of orange essential oil which is separated from the water layer by extracting it with chloroform. It had been observed that yield of the orange oil was much higher in the improved steam distillation extraction method for both the orange species in contrast to the conventional SD approach. Improved SD produced orange essential oil at almost two times more yield (4.237%) than that produced by using the conventional SD method (2.475%) in Citrus sinensis. Whereas; in Citrus reticulate, improved SD produced CEO in five times more yield (5.865%) than that obtained by using simple SD method (0.98%). The increase in the yield of EOs is probably due to softening of the cell walls of oil glands present on the peels, preheating, which on distillation rupture to release essential oils. The presence of limonene in both the essential oils is verified by FT-IR spectroscopy and GC analysis.

8.2.4 Hydrodistillation (HD) method Hydrodistillation (HD) is a modification of steam distillation (SD) which is used in the laboratories for the extraction of essential oils from dried samples. In place of steam used in SD, the plant extracts are dipped in water and the solid-liquid mixture is then boiled at atmospheric pressure. The heat releases the volatile aromatic constituents present in plant cells. These volatile components make an azeotropic mixture with water which undergoes evaporation followed by condensation and is then separated due to the virtue of its immiscibility. Recycling of water through the siphon enhances both the quality and yield of EOs (Li et al., 2014). Salma et al. (2016) analyzed the chemical composition and biological activity of EOs

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185

separated from aerial parts (stems, leaves, and flowers) of three aromatic and medicinal plants of bitter orange, geranium, and lemongrass. The extraction of EOs was carried out by hydrodistillation method in a Clevenger-type apparatus by boiling the plant material (100 g) with water (500 mL) for a period of 3 h in some distillation steps. The essential oils were analyzed by GC-MS analysis. The essential oils of Citrus aurantium were composed of 14 compounds dominated by limonene (40.81%) as the major component followed by linalool (26.66%), γ-elemene (7.97%), α-terpineol (4.97%), and α-terpinyl acetate (2.07%). Likewise, Ainane et al. (2019) studied the chemical composition and insecticidal activities of five essential oils extracted from Citrus limonum, Cedrus atlantica, Syzygium aromaticum, Rosmarinus officinalis, and Eucalyptus globules. The EOs were isolated from 250 g of leaves, stems, and flowers of the five plant species for a time interval of 3 h using the hydrodistillation approach with the aid of a Clevenger distiller. The vapors of EO mixed with water were first condensed and then separated in a separatory funnel. The EOs were dried with the help of anhydrous sodium sulfate and kept in a cool place in sealed tubes. The predominant components present in the essential oil of Citrus limonum as screened by GC-MS analysis are neral (13.60 %), neryl acetate (10.77%), geranyl isovalerate (6.75%), α-pinene (9.46%), cis- and trans-limonene oxide (6.7%), trans-α-bergamotene (3.36%), β-bisabolene (4.82%), linalool (2.21%), and limonenediol (3.22%), whereas the rest of the components are present in smaller amounts (less than 1%). Lately, Hilali et al. (2019) employed a green, zero-energy consuming, and environmentally friendly solar hydrodistillation process (SHD) containing a biorefinery system comprised of a Scheffler solar reflector for the extraction of essential oils and other nonvolatile components (pectins and polyphenols) from orange peels and compared the quality and yield of the extracted products with that obtained by using the conventional hydrodistillation method. Orange juice was first extracted by manual pressing of oranges and the byproduct (orange peels) was crudely crushed to obtain particles lying between 4 and 5 nm having a density of 0.45 g cm
3. The grounded orange peels so obtained were subjected to solar and conventional hydrodistillation processes. The yield of the extracted EOs by both methods was noticed to be similar with an insignificant deviation; 1.03% for the solar hydrodistillation extraction method and 1.05% for the conventional hydrodistillation process. However, the time required for extraction of EOs in the solar method was smaller (120 min) than that needed for the conventional method (190 min). The EOs present in the peels as quantified by GC-MS analysis indicated that the relative amounts of EO components in both oils extracted by the conventional and solar procedure were equivalent. The major components were limonene and myrcene which were obtained in 95.24% and 1.73% amounts for the conventional method and 95.96% and 1.7% respectively by employing the solar procedure (Table 8.2). However, solar radiations used in the solar hydrodistillation procedure were capable of increasing the extraction time by 36.8% without affecting the composition of EOs.

8.2.5 Ultrasound-assisted extraction (UAE) The prime flaw of many extraction methods using heat energy is the emergence of some thermally modified products like furan derivatives which are not acceptable in the food industry. To overcome this problem, ultrasound-assisted extraction (UAE) provides a better way out as thermal treatment is not needed in this method and thermal degradation of

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8. Citrus essential oil (grapefruit, orange, lemon)

extracted components is also prevented. UAE allows extraction of EOs due to tearing down of cell walls and enhanced mass transfer of cell contents under the influence of ultrasound energy. This technique has additional advantages such as a rapid extraction process, low energy requirements, low solvent consumption, and simple equipment to carry the extraction at a large scale. Ultrasound-assisted extraction is employed for the extraction of volatile components from several natural products at room temperature. Alissandrakis et al. (2003) attempted extraction of EOs from fresh flowers of four citrus species such as lemon, orange, sour-orange, and tangerine using UAE. On a comparative note, the components were also correlated with the volatile components extracted from citrus honey. To extract EOs, a sample consisting of 5 g of flowers along with 30 mL of n-pentane diethyl ether (1:2) was placed in an ultrasound water bath maintained at 25°C for 10 min. Thereafter, the extract was filtered through MgSO4.H2O to eliminate water and other solid matter and concentrated with a stream of nitrogen. The analysis of the extracted volatile components was performed with the help of GC-MS which indicated that linalool was present as the principal component in all the studied citrus species except in lemon. It was present in 80.6% in sour oranges, 51.6% in oranges, and 75.2% in tangerine flowers. The other components present in the essential oil of lemon were found to be β-pinene (11.8%), limonene (16.1%), eucalyptol (35.4%), linalool (11.3%), and α-terpineol (9.1%). However, the compound sabinene was found only in significant amounts in orange and tangerine flower extracts, up to 25.4% and 10.8% respectively. Compounds of ocimene and linalool acetate whose structure is related to the structure of linalool were found only in oranges and sour oranges up to 1% and 10.6% respectively. (Z)-2,6-dimethyl-2,7-octadiene-1,6-diol, a linalool derivative was found in very little amount in sour orange flower extract. The GC-MS analysis of citrus honey extracts indicated that the predominant component was the linalool derivatives (>80%). The flower extracts also encompassed linalool as the major component. The major components of citrus honey were found to be (E)-2,6- dimethyl-2,7-octadiene-1,6-diol (44.7%), 2,6-dimethyl-3,7octadiene-1,6-diol (15.4%) and Hotrienol (3,7-dimethyl-1,5,7-octatrien-3-ol) (4.7%) formed by thermal degradation of 2,6-dimethyl-3,7-octadiene-1,6-diol during GC analysis, (Z)-2,6-dimethyl-2,7-octdiene-1,6-diol (7.2%), lilac aldehydes (5.8%), lilac alcohols (2.5% in total), 2,6dimethyl-6-hydroxy-2,7-octadienal (low proportions), bis(2-ethylhexyl)adipate (in traces) formed as the artifact of storage. The comparison of the extracts of citrus flowers and citrus honey confirmed the presence of similar precursors in both and helped in confirming the geographical and botanical origin of honey. Darjazi (2011) also extracted EO from mandarin flowers employing the UAE method and analyzed it with the GC-MS technique. The presence of 38 components was established which included 17 oxygenated terpenes (3 aldehydes, 13 alcohols, 1 ketone), 14 nonoxygenated terpenes (9 monoterpenes hydrocarbons, 5 sesquiterpenes hydrocarbons), and 7 other components. However, the presence of 29 components including 10 oxygenated terpenes (2 aldehydes, 7 alcohols, 1 ketone), 17 nonoxygenated terpenes (13 monoterpenes hydrocarbons, 4 sesquiterpenes hydrocarbons), and 2 other components was established in EOs extracted using hydrodistillation. It proves the fact that the composition of EO is subject to change with a change in extraction method which is in agreement with many other reports (Lo Presti et al., 2005; Kimbaris et al., 2006; Bendahou et al., 2008; Da Porto and Decorti, 2009). The higher quantity of aldehydes and alcohols found in EOs extracted with UAE method as compared to hydrodistillation method is because of insignificant heating and little presence of water which keeps a check on its degradation. Thus,

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187

the UAE method is favorable for the extraction of aroma compounds which can be utilized as natural flavoring agents in food, aromatherapy products, pharmacy, and cosmetics. Gonza´lez-Rivera et al. (2016) attempted extraction of EOs from orange peels by coaxial solventless microwave-assisted extraction approach (SMWE) and simultaneous ultrasound coaxial microwave-assisted hydrodistillation (US-MWHD) approach which makes use of microwave (MW) and ultrasound (US) radiations and a coaxial dipole antenna dipped directly into the biomass source. The EOs isolated by these innovative techniques were analyzed for their chemical composition and then compared with the outcomes of conventional hydrodistillation (CH) and coaxial MWHD techniques. The solid residue left after the extraction of essential oils was utilized for pectin isolation by employing a biorefining approach. The GC-MS analysis indicated the presence of 11 volatile components in the essential oil. The EOs isolated from waste peels of oranges via different methodologies indicated similar chemical composition. The predominant components of CEOs were observed to be limonene and myrcene and their quantities increased with an increase in the extraction time. The larger amounts of valencene are extracted by using the US-MWHD approach. Valencene is the compound present in orange EOs which imparts a characteristic aroma and flavor and hence defines the quality and commercial value of orange Eos (Fig 8.3). Likewise, Jiang et al. (2011) tried out the extraction of EOs from the buds of bitter orange (Citrus aurantium) by ultrasound-assisted extraction (UAE) and compared it with reflux extraction (RE) and steam distillation (SD) extraction techniques. The quantitative and qualitative composition of EOs was evaluated by GC-MS analysis. Additionally, the EOs of C. aurantium is associated with their broad-spectrum biological activities like antifungal, antimicrobial, antiinflammatory, antioxidant properties, and anxiolytic effects (Quintero et al., 2001; Fisher and Phillips, 2008; Chutia et al., 2009; Senevirathne et al., 2009; De Moraes Pultrini et al., 2006). The EOs were obtained in 2.34%, 2.18%, and 0.16% yields in UAE, RE, and SD extraction respectively. In total, 82 components were identified by GC-MS analysis. The main components present in EO extracted by UAE were heneicosane, tetracosane, and palmitic acid present in 11.06%, 11.32%, and 8.76% respectively. However, the EOs isolated by the RE method contained 2-chloroethyl linoleate, palmitic acid, α-linolenic acid, and tetracosane existing in 14.54%, 20.61%, 11.24%, and 12.26%. On the other hand, terpinen-4-ol, terpinene, and dipentene present in 20.98%, 9.24%, and 11.67% respectively were the components present in CEO as extracted by the reflux extraction method. It was observed that SD helped isolate sesquiterpenes, monoterpenes, carbonyl compounds, and alcohols whereas UAE and RE were beneficial for extracting aliphatic and saturated hydrocarbons, esters, and acids.

8.2.6 Microwave-assisted extraction (MAE) method Generally, the isolation of EOs from citrus fruits or peels occurs in two basic steps of extraction (steam distillation or hydrodistillation) followed by analysis (GC or GC-MS analysis). The second step of analysis is completed in 15–30 min but extraction is a quite lengthy procedure as it needs heating and stirring for longer periods in boiling water (Ferhat et al., 2006). Microwave energy has a considerable influence on the rates of many processes in the food and chemical industry. The extraction of essential oils, phenols, pesticides, aromas, dioxins can be carried out efficiently from diverse matrices by utilizing the dielectric heating effect of

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microwaves. Microwave-assisted solvent extraction (MAE) acts as a practical alternative to conventional methods of extraction because of the diminution of solvents and extraction times as well. A few reports of speeding up the extraction of EOs by microwave energy are available in the literature (Craveiro et al., 1989; De Castro et al., 1999). Microwaves due to their selectivity can expand and rupture plant cell walls and allow the release of chemicals into the neighboring solvents quickly (Chemat and Esveld, 2001). MAE techniques have gained considerable attention from research groups due to smaller installation costs, environment-friendly nature, and smaller energy requirements (Mellouk et al., 2016). Many modules or alternatives of MAE have been used nowadays like microwave-assisted hydrodistillation, microwave steam distillation, microwave accelerated steam distillation, compressed microwave-assisted hydrodistillation, solvent-free microwave extraction, and microwave hydrodiffusion and gravity (MHG). MAE can be accomplished with or without the use of solvent or water. Though heating is facilitated in the presence of solvents, the use of solvent may cause hydrolysis of EO. Solvent-free microwave-assisted extraction (SFME) uses in situ water existing in the biomass for heating (Li et al., 2013). SFME can be carried out in two different manners: against gravity and in-favor of earth’s gravity.

8.2.7 Microwave-assisted hydrodistillation (MAHD) method Bustamante et al. (2016) employed an alternative technique of microwave-assisted hydrodistillation (MAHD) method for the extraction of EOs from waste orange peels (WOP) of Citrus sinensis; Navel Navelate variety which was frozen at low temperature (
18°C), defrosted, and milled to get small-sized particles (size less than 5 mm). The applicability of the process was verified by analyzing fresh peels of limes, lemons, grapefruits, sweet oranges, satsumas, and the quantification and characterization were performed with gas chromatography and time of flight mass spectrometry (GC-TOF) analysis. MAHD method is similar to the conventional hydrodistillation method with the only difference being that microwave radiations are used for heating purposes. The parameters required for increasing the yield and efficiency of the extraction process like the ratio of waste orange peel (WOP) and water, power, pressure, the time required for extraction were investigated and conditions were optimized. The essential oil (EO) yield from the Navel Navelate variety of oranges using MAHD method (1.8%, dry basis) was found to be similar to that obtained using conventional HD (1.7%; dry basis). The ideal conditions for the extraction of CEOs were observed to be WOP: water present in 1:1.5 ratio, constant pressure of 300 mbar during the irradiation process used over two repeated steps requiring 785 W power for 5 min and 250 W for 15 min for the next step. Gas chromatography with time of flight (GC-TOF) spectrometric analysis of the extracted EOs obtained by HD and MAHD method indicated that the composition and yields of the identified compounds present in both the extraction techniques were similar; with D-limonene present as the most abundant component in both (97.38% for MAHD and 96.75% for HD) as indicated in Table 8.1. However, MAHD could recover and quantify trans α-bergamotene and γ-terpinene, signifying that MAHD is a better extraction method than the conventional HD technique. There were significant differences in the yields of EOs not only among the investigated citrus species (oranges, limes, satsumas, lemons, and grapefruits) but also in a varied variety of oranges. More than 96.1% of nonoxygenated monoterpenes were

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TABLE 8.1 Chemical composition of the components present in essential oil extracted by microwave-assisted hydrodistillation method from different Citrus species. Citrus

Orange

Orange

Orange

Grapefruit

Lemon

Variety

Navel Navelate

Valencia Late

Navel Powell

Star Ruby

Primofiore

Monoterpenes

99.34

98.51

98.54

98.39

96.84

γ-Terpinene

0.04

0.04

0.04

4.82

11.35

D-Limonene

97.38

96.54

96.36

89.2

68.42

α-Pinene

0.39

0.35

0.41

0.96

1.89

Β-Pinene

0.06

0.07

0.07

1.59

12.31

R-β-Myrcene

0.79

0.84

0.9

0.93

0.83

Sabinene

0.5

0.53

0.46

0.23

1

M-3-carene

–

–

0.09

–

0.12

p-Cymene

–

–

–

0.1

0.19

α-Thujene

–

–

–

0.17

0.33

α-Terpinolene

0.18

0.13

0.22

0.33

0.27

Terpinene

–

–

–

0.05

0.13

Oxygenated monoterpenes

0.14

0.16

0.16

0.19

1.36

Terpinene-4-ol

0.01

0.01

0.01

0.04

0.42

Linalool

0.05

0.07

0.08

0.02

0.1

Terpineol

0.01

0.01

0.01

0.04

0.32

Geraniol acetate

–

–

–

0.02

0.41

Eucalyptol

0.06

0.06

0.07

0.06

0.12

Sesquiterpenes

0.01

0.52

0.51

0.09

0.1

β-Elemene

–

–

–

0.01

–

Valencene

–

0.08

–

0.04

0.02

β-Bisabolene

–

0.43

0.51

–

–

Trans α-bergamotene

0.01

0.01

–

0.04

0.08

Oxygenated sesquiterpenes

0

0

0

0.01

0.24

E-Citral

–

–

–

–

0.07

Z-Citral

–

–

–

0.01

0.16

Neryl acetate

–

–

0.01

0.04

0.13

Adapted from Bustamante, J., van Stempvoort, S., Garcı´a-Gallarreta, M., Houghton, J.A., Briers, H. K., Budarin, V.L., Matharu, A.S., Clark, J.H., 2016. Microwave assisted hydro-distillation of essential oils from wet citrus peel waste. J. Clean. Prod. 137, 598–605.

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found in the studied essential oils. D-Limonene was again the most abundant compound within the oils extracted from the studied citrus peels, ranging from 68.42% in the case of lemons to more than 96.3% present in oranges. Considerable amounts of gamma-terpinene, α, and β-pinene were also present in lime, lemon, and grapefruit essential oils. Recently Brahmi et al. (2021) also demonstrated extraction of EOs from the zest of four Citrus species including Navel (Citrus sinensis), Lemon (Citrus lemon), Bitter orange (Citrus aurantium), and Berkane clementine (Citrus clementina) by conventional HD as well as MAHD method. The two methods were then compared in terms of chemical composition, the yield of EOs, and their antimicrobial and antioxidant properties. The chemical composition was determined with the help of GC-MS analysis. EOs extracted from all the investigated citrus species for both the extraction methods were majorly composed of limonene (55%–77%) along with other components like α-pinene and β-myrcene. However, there were quantitative as well as qualitative differences that exist between the extracted EOs in HD and MAHD techniques. The number of components present in EOs of bitter orange and lemon oil was found to be 9 and 19 respectively when the HD technique was employed for extraction whereas EOs extracted by the MAHD method contained only 5 and 3 components. Contrarily, EOs extracted from Navel and Berkane clementine species by the MAHD method were analyzed to have a larger number of chemical compounds (9 and 13 respectively) in contrast to EOs extracted by the conventional HD method. Moreover, the yield of EOs obtained by using MAHD is much better than that acquired by the HD method. All the EOs showed excellent antioxidant properties with the highest activity observed in Navel EO having 44.45% activity followed by lemon EOs exhibiting 28.85% activity. The CEOs extracted by the HD method displayed noteworthy antimicrobial activity w.r.to Aspergillus niger with the highest activity being shown by lemon EO having an average inhibition zone of 35 mm whereas Navel displayed an average inhibition value of 14 mm (Fig 8.1).

8.2.8 Ionic liquid-based microwave-assisted extraction (MAE-IL) method Ionic liquids (ILs) have been notified as appropriate solvents/cosolvents/additive media for microwave-assisted extraction due to their capacity to absorb microwave radiation effectively and efficiently (Yang et al., 2012). Ionic liquids can fasten the extraction process of EOs due to their excellent solvation and dielectric properties and their surfactant activity permits better interactions with water molecules ( Jiao et al., 2013; Hou et al., 2019; Liu et al., 2016). Moreover, IL-based MAE allows the EOs to be isolated in the vapor phase mixed with water and devoid of ILs. Recently, Franco-Vega et al. (2021) attempted isolation of EOs from the peels of Citrus sinensis (Valencia variety) by using MAE aided by two imidazolium-based anionic Ionic liquids having varied chain lengths; namely 1-butyl-3-methylimidazolium chloride ([C4mim]Cl) and 1-ethyl-3-methylimidazolium acetate ([C2mim]OAc). The efficiency of the ionic liquid-based microwave assisted extraction (MAE-IL) process along with the yield of EOs and thermal behavior were investigated by taking two different concentrations (5% and 10%) of ILs and compared with MAE using water solvent. The yield of isolated CEOs was higher in the presence of both the ILs in comparison to MAE using water as solvent. However, [C2mim] OAc gave better yields than [C4mim] Cl owing to its better solvating power for cellulose. The yield of EOs increased from 1.33% to 2.13% at 10% concentration level in

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191

FIG 8.1

Comparison of the yield of essential oils extracted from Citrus zest by HD and MAHD methods. Adapted from Brahmi, F., Mokhtari, O., Legssyer, B., Hamdani, I., Asehraou, A., Hasnaoui, I., Tahani, A., 2021. Chemical and biological characterization of essential oils extracted from citrus fruits peels. Mater. Today: Proc. 45, 7794–7799.

comparison to MAE using water solvent. The enhanced efficiency of the MAE-IL process is probably due to the dissolution of cellulose by ILs and the faster release of essential oils from cracked plant cells. The distillation process was also facilitated due to the increase in velocity of microwave heating and homogenization of emulsion of water and essential oils because of the surfactant nature of ionic liquids. Furthermore, a 30% decrease in the time required for isolation of EOs was noticed on using [C2mim] OAc at 10% in contrast to MAE using only water. The chemical components present in EOs as quantified by GC/MS analysis indicated the presence of limonene as the predominant component (>84%); but the composition varied with change in the nature of the ionic liquid (IL) used and its composition. The extraction by microwave-assisted method in absence of IL indicated the presence of 12 components belonging to four varied groups (monoterpene hydrocarbons, esters, aldehydes, and sesquiterpenes) with limonene (84.84%) as the main component along with linalyl formate (1.46%) and α-pinene (1.92%). It is pertinent to note that limonene was present as a major component (95.77%) for [C2mim]OAc and (88.10%) for [C4mim]Cl) at 5% concentration level of ILs. EO comprising of components belonging to six major groups (monoterpene hydrocarbons, sesquiterpenes, aldehydes, phenylpropanoids, oxygenated monoterpenes, and esters) were observed at 5% concentration level of [C2mim]OAc and ten major groups (oxygenated monoterpenes, phospholipids, phenylpropanoids, alcohols, phenols, and phthalates as additional compounds) were detected when concentration was increased to 10%.

8.2.9 Microwave-assisted hydrodiffusion and gravity method (MHG) Microwave hydrodiffusion and gravity (MHG) serves as a green alternative for the extraction of natural products. It is a union of two different processes of microwave heating and

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8. Citrus essential oil (grapefruit, orange, lemon)

gravity under atmospheric conditions of pressure (Bousbia et al., 2009). When the plant material required for the extraction of EOs is put in a microwave reactor without using water or any other solvent, the heating of the water present in plant cells expands and ruptures the cell glands and receptacles, allowing the release of plant extract mixed with water already present in plant cells by a physical process of hydrodiffusion and gravity of the earth allows the collection and separation of plant extracts (metabolites and in situ water). The energy and solvent consuming steps of distillation and solvent extraction are eliminated in this green extraction method, so it permits faster and efficient extraction without any solvent consumption and a considerable energy saving too. Bousbia et al. (2009) extracted EOs from lemon peels using the MHG technique and compared the rate, yield, composition, and energy requirements of the process with the conventional HD and cold pressing (CP) methods. The final yield and composition of essential oils and secondary metabolites obtained by MHG, CP, and HD from lime peels were quite similar. The yield of EO given by MHG in 15 min is comparable to that obtained by HD in 180 min. The composition as analyzed by GC-MS analysis indicated limonene (monoterpene hydrocarbon) as the major component of EO extracted from lemon (70.9% in MHG, 71.86% in CP, and 71.22% in HD) followed by geranial (oxygenated monoterpene) (1.37% in MHG, 1.82% in CP and 0.85% in HD). The microwave treatment had only hastened the extraction process without causing any compositional change (Chen and Spiro, 1995; Pare and B
elanger, 1997). However, the EOs extracted by using these three techniques differed in their organoleptic properties. EOs extracted by MHG and CP possessed the fragrance of terpenes hydrocarbons with a sweet, light, fresh citrusy scent. Whereas, the essential oils extracted by HD possessed the smell of terpenes hydrocarbons which was pungent and different from the odor of fresh citrus fruit. Likewise, Fidalgo et al. (2016) attempted simultaneous extraction of EOs and pectin from lemon peels and waste orange by using an innovative solvent-free microwave extraction (SFME) method and microwave hydrodiffusion and gravity (MHG) method followed by freeze-drying. In this process, water was used as a dispersion medium and microwave radiation was used as an energy source. The analysis of extracted EOs and pectin at semi-industrial and laboratory scales was performed by Infrared Fourier transform spectroscopy in diffuse reflectance mode (DRIFT). A similarity in the IR spectra of EOs isolated from waste lemon peels and orange peels (both fresh and waste) was detected. The appearance of IR bands at 3100 and 2800 cm
1 represented the characteristic band of C-H stretch of sp3 and sp2 hybridized carbons, the bands at 1645, 1376 and 1437 cm
1 are indicative of C¼C bond and bending modes of CH3 group, whereas the bands at 887 and 797 cm
1 represented out of a plane (oop) bending vibration of ¼CH2 of vinylidene group and ¼C-H (oop) bending vibration of trisubstituted alkene (Socrates, 2004). The IR signified the presence of limonene (Zapata et al., 2009). Whereas, the EOs isolated from fresh lemon rind displayed strong IR bands at 1232, 1679, and 1740 cm
1 and weaker peaks at 1020 and 1690 cm
1. The ratio of the intensities of the bands at 1740 (ν C¼O) and 1232 cm
1 indicated (ν C-O-C) the occurrence of linalyl acetate (Sawamura, 2011).

8.2.10 Microwave accelerated distillation (MAD) method Ferhat et al. (2006) carried out microwave accelerated distillation (MAD), a blend of microwave heating and distillation, for extraction of EO from orange using the "DryDist"

8.2 Extraction and characterization of citrus essential oils (CEOs)

193

microwave oven. In this method, 200 g of fresh orange peels are placed in a microwave reactor without any added solvent or water and were heated using a power density of 1 Wg
1 at 100°C for 30 min. Consequently, the distillate was condensed to collect EO which is then dried over anhydrous sodium sulfate and stored at 4°C. The MAD process is different from modified microwave-assisted extraction (MAE) which uses organic solvents and modified hydrodistillation (HD) which requires a large quantity of water. GC-MS analysis revealed that limonene, β-myrcene, linalool, α-sisensal, and decanal were the major components of extracted EO from orange peels. However, relative amounts of different components vary with the method of extraction. The percentage of oxygenated fraction (11.7%) which is more odorous than hydrocarbon fraction (7.9%) in EO extracted by the MAD process increases the value of this process. The elevated amount of oxygenated fraction may be due to diminished thermal and hydrolytic effects as the process was carried out in the absence of any solvent. The MAD process serves as a quicker (requiring 30 min over 3 h required by HD), environment-friendly, economical, more efficient (0.42% yields over 0.39% in HD) technique producing larger amounts of oxygenated products and preserving the natural aroma of CEOs over the conventional HD process (Fig 8.2).

8.2.11 Supercritical fluid extraction Xiong and Chen (2020) utilized a supercritical CO2 extraction technique for the extraction of EO from tangerine which is a type of orange. This technique for extraction has been gaining importance because of its environment-friendly nature. Furthermore, physicochemical properties of carbon dioxide like nontoxic nature, adequate solvent power, economical, incombustible, low critical temperature (31.1°C), and pressure (7.38 MPa) enabled low working temperature and prevented thermal degradation of certain compounds. Thus, this technique

100% 80% 60% 40% 20% 0% Extraction time (min)

Electric consumption (kWh)

MAD

CO2 rejected (g)

HD

FIG 8.2 Comparison of extraction time, energy consumption and CO2 released for EOs extracted by MAD and HD methods. Adapted from Ferhat, M.A., Meklati, B.Y., Smadja, J., Chemat, F., 2006. An improved microwave Clevenger apparatus for distillation of essential oils from orange peel. J. Chromatogr. A 1112 (1–2), 121–126.

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8. Citrus essential oil (grapefruit, orange, lemon)

improves the quality and yield of extracted essential oil. The experimental procedure consists of filling the extraction vessel with 270 g dried sample and fluid vessel with carbon dioxide and then converting it into supercritical carbon dioxide. The stream of supercritical carbon dioxide was then passed into the extraction vessel at optimum values of temperature, pressure, particle size, and extraction time which are 45°C, 25 MPa, 0.35 mm, and 120 min respectively. Eventually, essential oil from tangerine was collected and its yield was calculated. Optimum conditions were obtained by experimenting with a wide range of variables like the pressure of 15–35 MPa, the temperature of 35–55°C, the particle size of 0.3–1.25 mm, and the extraction time 60–120 min. It was seen that yield of EO increased from 0.72% to 0.89% on decreasing particle size from 1.0 to 0.4 mm though it decreases from 0.89% to 0.8% if particle size was further reduced to 0.2 mm. This is because initially, the surface area of tangerine peel increases with a decrease in particle size which allows proximity of supercritical carbon dioxide thus greater amounts of EO are extracted. However, further decrease in size causes reabsorption of extracted EO on the surface of peel powder thereby decreasing the yield. It also promotes a better flow of scCO2 through micro-channels formed in the packed bed giving rise to insufficient contact between scCO2 and peel powder (Pourmortazavi and Hajimirsadeghi, 2007). The yield of EO from tangerine peel was increased by increasing the temperature from 35°C to 45°C but decreased with a further increase in temperature. This observation is due to a decrease in the density of scCO2 and an increase in the diffusion rate of extracted EO with an increase in temperature. A decrease in density lessens the solubility of extracted EO in scCO2 thus decreases its yield and an increase in the diffusion rate of extracted EO enhances its yield. There are many reports (Herzi et al., 2013; Sodeifian et al., 2016; Palsikowski et al., 2019, 2020; Santos et al., 2019) verifying the fact that as these two factors operate in opposite directions so their integrated effect determines the yield. Effect of change in pressure was also checked and it was found that at first yield increased with an increase in pressure. The yield was maximum at 15 MPa pressure, however, it began to reduce with a further increase in pressure to 25 MPa and it was not much affected if pressure was increased from 25 to 30 MPa. These changes in yield were observed on account of an increase in the density of scCO2 with an increase in pressure which enhances its solvating capacity toward extracted EO though further increase in pressure restricts diffusion of scCO2 (Frohlich et al., 2019; Palsikowski et al., 2019; Santos et al., 2019). GC-MS analysis recognized 35 chemical components in the tangerine peel EO among which the major components were n-hexadecanoic acid (14.62%), linoleic acid (32.3%), and oleic acid (20.42%).

8.2.12 Enzyme assisted extraction (EAE) Many researchers (Bhat, 2000; Sowbhagya et al., 2011) have started using nonconventional methods like enzymatic treatment for the extraction of some important compounds from agro-industrial waste. Along the same lines, Cha´vez-Gonza´lez et al. (2016) utilized enzymatic treatment for extracting EO from orange, lemon, and grapefruit peels. 100 g of peels combined with 250 mL of citric acid/sodium citrate buffer 0.1 M (pH 4.5) was heated in a ball flask at 100°C for 10 min to deactivate the endogenous enzymes. The mixture was cooled and then

8.3 Composition of citrus essential oils (CEOs)

195

1 mg of cellulase enzyme per gram of the sample was added. Again, it was heated at 50°C under constant stirring for hydrolysis and subsequently put through hydrodistillation. Ultimately EO was extracted and its yield was noted. Enzyme-assisted extraction enhances the yield of essential oil extracted from orange, lemon, and grapefruit as compared to the traditional hydrodistillation method. Along with high yield, this method also liberates a remarkable quantity of sugars that can be used in fermentation processes. The major component of EO was limonene in all citrus fruits under investigation. Orange peel oil has its maximum concentration (90.18  1.20%), followed by grapefruit (80.34  0.96%) and then lemon (80.02  0.48%). Similar results were obtained by earlier reports (Njoroge et al., 2005; Rezzoug and Louka, 2009; Singh et al., 2010; Hosni et al., 2010; Misharina et al., 2011; Sahraoui et al., 2011) (Table 8.2).

8.3 Composition of citrus essential oils (CEOs) CEOs are a combination of oxygenated monoterpenes, oxygenated sesquiterpenes, monoterpene hydrocarbons, and other oxygenated compounds. The composition of EOs is dependent on many factors like the type, variety, origin, sweetness or bitterness, maturity, and harvesting season of citrus fruits (Lo´pez et al., 1993; Lota et al., 2002; Argyropoulou et al., 2007; Hamdan et al., 2010; Kamal et al., 2011; Al-Jabri and Hossain, 2014; Kamaliroosta et al., 2016). The gas chromatography study and mass spectrometry analysis are performed to find the composition of CEOs. Approximately 20–60 compounds are present in each CEO (Bakkali et al., 2008). The volatile components comprise more than 85% of this number whereas nonvolatile components are present in 1%–15% of the composition. The volatile components comprise sesquiterpenes, monoterpenes, and sesquiterpenoids (Smith et al., 2001). Monoterpenes are present as the predominant component (about 97%) of CEOs and are made up of two isoprene units. The remaining part (1.8%–2.2%) is aldehydes (sinensal, citronellal), alcohols (α-bisabolol, geraniol), phenols (thymol), and esters (cedryl acetate, γ-terpinyl acetate) (Moufida and Marzouk, 2003; Modzelewska et al., 2005; Fisher and Phillips, 2008). Limonene is the major monoterpene compound present in citrus essential oils and is present in 32%–98% concentration depending upon the variety of citrus fruits; sweet oranges contain 68%–98%, lemons contain 45%–76 % and bergamot contains 32%–45% of limonene (Moufida and Marzouk, 2003). The peculiar aroma of CEOs is dependent on the length of the unsaturated un-branched aldehydes with chain length ranging from (C8-C14), nootkatone, acetate and α-selinenone. The main odor causing components of Citrus aurantium peel oil were geraniol, geranyl acetate, linalool and linalyl acetate (Tamura et al., 1993). The lemon peel oil is enriched with monoterpene components other limonene like γ- terpinene present in lemon rind and outer skin as well as β-pinene existing in the peel, outer skin, and lemon waste which imparts it its characteristic "green peely" smell (Ciriminna et al., 2017). Additionally, borneol, linalool polymethoxy flavones (PMFs), hydroxylated polymethoxy flavones (HPMFs), and other oxygen heterocyclic compounds, such as furanocoumarins, e.g., isoimperatorin must be considered as important constituents of CEOs. Maximum limonene (86.3%) along with myrcene (6.28%) is present in EO obtained from grapefruit. Structures of some common constituents of EOs from citrus fruits are given in Table 8.3.

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8. Citrus essential oil (grapefruit, orange, lemon)

TABLE 8.2 GC-MS analysis of composition of essential oil extracted from waste orange peels by conventional hydrodistillation and solar hydrodistillation. S. No.

Compound

Conventional hydrodistillation (%)

Solar hydrodistillation (%)

1.

α-Pinene

0.39

0.37

2.

Myrcene

1.73

1.7

3.

Sabinene

0.19

0.16

4.

Camphene

0.01

0.01

5.

β-Pinene

0.02

0.02

6.

δ-3-Carene

0.14

0.08

7.

α-Phellandrene

0.08

0.05

8.

Limonene

95.24

95.96

9.

α-Terpinene

0.02

0.01

10.

Υ-Terpinene

0.03

0.02

11.

Linalool

0.3

0.23

12.

Nerol

0.01

0.01

13.

Citronella

0.01

0.01

14.

Geraniol

0.01

0.02

15.

Neral

0.01

0.01

16.

Geranial

0.01

0.01

17.

α-Copaene

0.02

0.02

18.

β-Elemene

0.02

0.02

19.

β-Cubebene

0.01

0.01

20.

Valencene

0.11

0.13

21.

β-Caryophyllene

0.02

0.02

22.

Caryophellene oxide

0.02

0.01

23.

α-Sinensal

0.01

0.01

24.

β-Sinensal

0.01

0.02

25.

Nootkatone

0.01

0.02

26.

Decanal

0.16

0.17

27.

Citronellyl acetate

0.01

0.01

28.

α-Terpenyl acetate

0.02

0.02

Adapted from Hilali, S., Fabiano-Tixier, A. S., Ruiz, K., Hejjaj, A., Ait Nouh, F., Idlimam, A., Bily, A., Mandi, L., Chemat, F., 2019. Green extraction of essential oils, polyphenols, and pectins from orange peel employing solar energy: toward a zero-waste biorefinery. ACS Sustain. Chem. Eng. 7 (13), 11815–11822.

8.3 Composition of citrus essential oils (CEOs)

TABLE 8.3 Structures of well-known components present in the essential oils from citrus (oranges, lemon and grapefruits).

Monoterpenes

Oxygenated monoterpenes (terpenoids)

Polymethoxyflavones (PMFs) and hydroxylated PMFs

Other oxygen heterocyclic compounds (furanocoumarins)

197

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8. Citrus essential oil (grapefruit, orange, lemon)

8.4 Applications of citrus essential oils Citrus essential oils are being valued for their broad range of properties such as antimicrobial, cytoprotective, antioxidant, antiinflammatory, and anthelmintic (Table 8.4). The Food and Drug Administration authenticates the essential oils as flavoring agents in some foods. Citrus oils are used as antimicrobial within the food industry and these are considered to be safe for food and beverages. Citrus oils can decrease the putrefaction and increase organoleptic assets in food products (Bajpai et al., 2012; Dosoky and Setzer, 2018). Hamdan et al. (2013) displayed that lemon oil is employed as an additive and flavoring agent due to its functional characteristics. They can enhance the shelf life of foodstuffs and in the manufacture of a few kinds of cheese as they markedly decrease the microbes, particularly those from the Enterobacteriaceae family (Gonza´lez-Molina et al., 2010; Randazzo et al., 2016). Thus, citric essential oils have a broad range of applications in food safety, wrapping, and preservation. These essential oils’ phenolic components are encapsulated and used for the protection of foods from microbial decomposition and phospholipid oxidative degradation. In addition, citric essential oils are cost-efficient, eco-friendly, and comparatively harmless and can be used for nanoemulsions for their role in food manufacturing. The protective efficacy of citrus essential oil nanoemulsions (orange, lemon, and grapefruit) were examined for antioxidant and antibacterial activity against preserved rainbow trout fillets. Nanoemulsions of oil showed remarkable inhibitory activity against the multiplication of bacteria in contrast to TABLE 8.4 Chief phytoconstituents of various citrus essential oil and functions. Phytoconstituents

Citrus species

Biological activity

References

Limonene

Lemon, orange, mandarin

Antiinflammatory, antidiabetic, anticancer, antioxidant

Hosni et al. (2010) Jing et al. (2013)

ά pinene

Lemon, orange, mandarin, pummelo

Antimicrobial

Lota et al. (2002)

Camphene

Lemon, sour orange, lime, mandarin, pummelo

Lipid lowering

Vallianou et al. (2011)

β pinene

Lemon, orange, mandarin, pummelo

Antifungal

Jabalpurwala et al. (2009)

Sabinene

Lemon, orange, mandarin, pummelo

Antifungal

Hosni et al. (2010) Lota et al. (2002)

ά Phellandrene

Orange, mandarin

Insecticidal

Hosni et al. (2010)

β Myrcene

Lemon, orange, mandarin, pummelo

Antifungal Embryofetotoxicity

Lota et al. (2002) Jabalpurwala et al. (2009)

Ocimene

Lemon, orange, mandarin, pummelo

Antiviral, Antifungal, antibacterial, antioxidant, antiinflammatory

Hosni et al. (2010) Lota et al. (2002) Jabalpurwala et al. (2009)

199

8.4 Applications of citrus essential oils

TABLE 8.4

Chief phytoconstituents of various citrus essential oil and functions—cont’d

Phytoconstituents

Citrus species

Biological activity

References

Valencene

Citrus limon, orange

Antiinflammatory, antiallergic

Moufida and Marzouk (2003)

β Elemene

Lemon, orange, grapefruit, pummelo

Anticancer

Lota et al. (2002) Zhu et al. (2011)

β Caryophyllene

Lemon, orange, mandarin, pummelo

Antibiotic, antibacterial, antioxidant, antiinflammatory

Lota et al. (2002) Jabalpurwala et al. (2009) Legault and Pichette (2007)

ά Humulene

Lemon, orange, mandarin, pummelo

Anticancer

Hosni et al. (2010) Lota et al. (2002) Legault and Pichette, 2007

Geranial

Mandarin, orange, lemon

Antifungal

Lota et al. (2002) Jabalpurwala et al. (2009) Wuryatmo et al. (2003)

Geraniol

Lemon, orange, grapefruit, pummelo

Anticancer, antibacterial, antioxidant, antiinflammatory

Lota et al. (2002) Jabalpurwala et al. (2009)

ά/β Citronellol

Mandarin, orange, lemon

Antiinflammatory

Lota et al. (2002) Jabalpurwala et al. (2009)

Neral

Lemon

Antifungal

Lota et al. (2002) Wuryatmo et al. (2003)

Nerol

Lemon, orange, mandarin, pummelo

Antibacterial

Lota et al. (2002) Jabalpurwala et al. (2009)

ά-Terpineol

Lemon

Antifungal

Lota et al. (2002)

Linalool

Lemon, orange, mandarin, pummelo

Antidiabetic

Lota et al. (2002) Jabalpurwala et al. (2009) Deepa and Anuradha (2011)

Thymol

Orange, mandarin

Antibacterial

Jabalpurwala et al. (2009) Betancur-Galvis et al. (2011)

200

8. Citrus essential oil (grapefruit, orange, lemon)

FIG 8.3 Coaxial microwave assisted technology to obtain citrus essential oil. Adapted from Gonza´lez-Rivera,J., Ducea, C., Falconieri, D., Ferrari, C., Ghezzi, L., Piras, A., Tinea, M.R., 2016. Coaxial microwave assisted hydrodistillation of essential oils from five different herbs (lavender, rosemary, sage, fennel seeds and clove buds): chemical composition and thermal analysis. Innov. Food Sci. Emerg. Technol. 33, 308–318.

the control (Durmus, 2020). Calo et al. (2015) reported that the essential citrus oils can alter the cellular structure of microorganisms along with oxidative stress which leads to apoptosis (Fig. 8.3).

8.4.1 Antioxidant activity Citrus essential oil is a reservoir of active constituents which assist in the inhibition of oxidative stress and related infections (Fig 8.4). It is a worthy alternative for synthetic antioxidants in food applications. The antioxidant potential of oils of 14 Chinese Citrus species was examined (Guo et al., 2018). It was observed that bergamot and lime essential oil showed robust antioxidant potential and can be employed as a natural food additive to hamper oxidation. Citrus lumia oil showed good antioxidant properties which might be ascribable to the higher amount of linalool and limonene (Smeriglio et al., 2018). Essential oil of C. pyriformis and Citrus jambhiri showed remarkable antioxidant potential with an IC50 of

FIG 8.4 Chemical composition and biological potential of citrus essential oil.

8.4 Applications of citrus essential oils

201

28.9 and 37.7 mg/mL, respectively (Hamdan et al., 2010). Essential oil of C. acida revealed an antioxidant effect with 92% of DPPH scavenging activity (Mahmud et al., 2009). C. sinensis oil displayed DPPH radical scavenging potential with IC50 values of 9.5 μL/mL depicting their robust antioxidant activity (Singh et al., 2010). Essential oil of C. aurantium, and C. bergamia revealed marked radical scavenging action and IC50 values were found to be 201.3, 192.9, and 188.9 μg/mL, respectively (Tundis et al., 2012). Essential oil of Citrus medica showed significant variations in antioxidant properties during diverse ripening phases of the fruit. Essential oil of citrus at immature, intermediate, and mature phases revealed 78.4%, 64.7%, and 63.8% DPPH scavenging activity respectively (Wu et al., 2013). Essential oil of C. reticulata demonstrated IC50 of 22.60 and 1.62 mg/mL through different assays (Yi et al., 2018). The antioxidant efficacy of essential oil of citrus fruits is attributed to the number of active components present in them. The main phytoconstituents responsible for antioxidant activity were thymol, α-terpineol, citral, γ-terpinene, α-sinensal, and citronellal. The antioxidant potential of thymol and citral were observed to be comparable with that of α-tocopherol. Essential oil of C. bergamia might be used for the cure of several chronic infections related to oxidative damage as they showed antioxidant and lipoxygenase inhibitory activity (Wei and Shibamoto, 2010). Essential oil from Navel Orange peel demonstrated antioxidant effect with inhibitory concentration 2 mg/mL, respectively (Yang et al., 2017). Likewise, Ben Hsouna et al. (2019) reported that the essential oil of orange displayed antioxidant activity in a concentrationdependent manner in contrast to the ascorbic acid. Sajid et al. (2016) monitored the antioxidant potential of essential oils of C. pseudolimon and C. grandis through DPPH radical scavenging assay. It was observed that C. pseudolimon has revealed more antioxidant potential in contrast to the C. grandis (IC50 ¼332.64 μg/mL). Similarly, Shahzad et al. (2009) demonstrated the antioxidant potential of a few citrus species about 77%. The antioxidant potential of citrus oils might be accredited to the existence of phenolic constituents. In phenolic components, -OH groups present in the aromatic ring could be accountable for its potential to produce hydrogen atoms and it alleviated the production of radicals (Senthilkumar and Venkatesalu, 2013). Brahmi et al. (2021) reported the maximum antioxidant activity of essential oil of Navel was observed to be 44.45% and the minimum antioxidant activity of essential oil of Bigarade was found to be 10.66%. These essential oils might be used in the food industry as bio-fungicide but also as additives in the pharmaceutical and cosmetic industries. In another investigation, the antioxidant activity of the Citrus limon oil was tested and IC50 of oil was observed to be 284.7 μg/mL (Ghoorchibeigi et al., 2017). Various studies indicated the DPPH radical inhibitory activity of oil of C. aurantium was observed to be 13.93% (Khettal et al., 2017; Kaca´niova´ et al., 2020). However, the previous study of Bendaha et al. (2016) demonstrated the antioxidant potential of C. aurantium was found to be 15.33%. In another study, citrus essential oils and their constituents like limonene, β-pinene, phellandrene, myrcene, geranial, α-pinene, and geraniol) were investigated against dysmenorrhea. It was observed that these oils have the ability to enhance the antioxidant markers (Catalase, Superoxide dismutase, and Glutathione) and decreasing the concentration of malondialdehyde and nitric oxide synthase in estradiol benzoate injected rats, thus bettering the squirming movements. This study presented that essential oils of citrus can remarkably hamper oxidative stress and prostaglandins stimulate uterine contraction, depicting an effective therapeutic agent against dysmenorrhea (Bi et al., 2021). The antioxidant potential of essential oils of mandarin and geranium at different concentrations (25–200 μg/mL) were monitored. The mandarin and geranium essential oils decreased the DPPH free radical concentration with an

202

8. Citrus essential oil (grapefruit, orange, lemon)

efficiency identical with ascorbic acid which is a standard antioxidant. The 50% effective concentration of mandarin essential oil was observed to be 79.84 μg/mL in contrast to geranium essential oil where it was found to be 66.45 μg/mL (Fayed, 2009).

8.4.2 Antiinflammatory activity Chronic pain caused due to exaggerated inflammatory processes is a huge clinical problem globally. Antiinflammatory drugs like aspirin, diclofenac, and indomethacin hinder the prostaglandins biosynthesis pathway by impeding the cyclooxygenase enzymes and showing analgesic and antiinflammatory effects. However, these drugs exhibit adverse effects upon chronic administration. This motivated further search for natural products which could serve in the battle against inflammatory diseases and could provide a novel antiinflammatory agent. In this aspect, citrus essential oil serves as an efficient antiinflammatory agent (De Almeida Barros et al., 2010). The leaves and peel essential oil of Citrus sinensis showed a significant (P < 0.01) reduction in swelling in the hind paw in rats. The presence of limonene in the essential oil of peels and β-elemene and sabinene in the essential oil of leaves revealed an active part in the antiinflammatory potential of Citrus sinensis (Matuka et al., 2020). Bhutia (2020) demonstrated that essential oil made from Citrus macroptera was found to be more effective as an antiinflammatory agent in contrast to standard diclofenac. It was observed that citrus essential oil hampers the heat-stimulated denaturation of albumin. In another study, treatment of essential oil from Citrus limetta peels displayed marked inhibition of proinflammatory cytokines in macrophages upon stimulation through lipopolysaccharides. Macrophages pretreated with citrus essential oil showed a reduction in the levels of free radicals in Hydrogen peroxide-stimulated oxidative stress. Further topical treatment of citric essential oil was observed to diminish the 12-O-tetradecanoylphorbol-13-acetate-stimulated ear thickness and weight, pro-inflammatory cytokines, lipid peroxidation, and recover the impairment in the mice ear tissue. This study indicates the safe antiinflammatory potential of citrus essential oil against inflammation-associated skin infections (Maurya et al., 2018). Lombardo et al. (2020) demonstrated the antiinflammatory potential of essential oil extracted from Citrus bergamia. Supplementation of Citrus bergamia oil displayed marked inhibition of paw edema in rats caused by carrageenan. It was found that treatment with Citrus bergamia oil revealed a remarkable decrease in the pathological alterations of paw edema. Pretreatment with Citrus bergamia oil caused a significant decrease in the concentration of TNF-α, IL-1, and IL-6 in the paw homogenates.

8.4.3 Antitumor assay Deng et al. (2020) demonstrated that essential oil extracted from grapefruit displayed remarkable inhibition against the HepG2 hepatoma and HCT116 colon cancer cells. The viability of the cancer cells was observed to be about 7.4% after the treatment of grapefruit oil. The C. pseudolimon oil revealed more protective efficacy (81.25%) against the cancer cells in comparison to the standard drug vincristine (78.69%). However, C. grandis was found to be less effective against the cancer cells and the inhibition against the cancer cells was observed to be 61.53% (Sajid et al., 2016). Da Silva et al. (2020) displayed that the essential oils of C. aurantium might be potent therapeutic agents due to their anticancer efficacy with negligible adverse

8.4 Applications of citrus essential oils

203

effects on the blood cells. The antitumor efficacy of Citrus essential oils is accredited to the presence of flavonoids and limonoids in citrus plants. These compounds showed their effect by hindering cell proliferation, signaling, and angiogenesis (Kundusen et al., 2011). The potential of orange peel oil against the A549 (mammalian lung cancer) and 22RV1 (mammalian prostate cancer) cells were determined. The 50% inhibition concentration of orange peel oil against the A549 cells was observed to be 17.5  0.9, 10.7  0.5, and 7.8  0.38 at the different incubation periods (24–72 h). Moreover, 50% inhibition concentration of orange peel oil against the 22RV-1 cells was found to be 45.7  1.7, 42.8  1.6, and 39.8  1.6, at 24–72 h incubation, respectively. It was noticed that maximum inhibition against the A549 and 22RV1 cells has been shown by essential oil of orange peel at 6.3–200 μg/mL (Yang et al., 2017). Citrus reticulata oil induces hindrance of non–small cell lung carcinoma cells and inhibits the multiplication of cancer in nude mice. It causes cell cycle arrest in the G0/G1 phase and induces the reduction in Ras protein along with stimulation of apoptosis. Treatment of Citrus reticulata oil showed no toxicological outcome in hepatic markers and histology of the organ was observed to be normal. Therefore, citrus oil displays remarkable anticancer potential without inducing systemic harmfulness, recommending citrus oil as a nutritional supplement that might assist in the cure of cancer (Castro et al., 2018). The antitumor action of the essential oils of mandarin and geranium at different concentrations (25–200 μg/mL) against mammalian promyelocytic leukemia cell lines (HL-60 and NB4) were determined. Essential oil of geranium displayed the maximum antitumor potential with the LC50 of 63 and 87 μg/mL against NB4 and HL-60 cell lines respectively. However, mandarin essential oil gave the LC50 of 85 and 105.73 μg/mL against the similar type of cells respectively (Fayed, 2009).

8.4.4 Antiprotozoal activity Essential oil of citrus revealed significant inhibitory activity against promastigotes of Leishmania amazonensis and IC50 was observed to be 8.2 μg/mL. Essential oil of citrus displayed marked larvicidal potential against 3rd instar Aedes aegypti larvae at a lethal dose of 58.35 μg/mL and 100% death rate at 150 μg/mL (Oliveira et al., 2021). In another study, essential oil of citrus fruits was observed to be effective against the amastigotes of L. major and IC50 was observed to be 4.2 μg/mL. The efficacy of citrus oil was found to be comparable with miltefosine. Moreover, citrus oil displayed negligible cytotoxicity against macrophages and a high therapeutic index, indicating the safe profile of citrus oil. The mechanism behind the leishmanicidal activity of essential citrus oil might be related to the lipophilic characteristics of terpenes which are remarkably responsible for the disruption of intracellular metabolic signaling of the parasite (Maaroufi et al., 2021). Citrus limon was found to show significant activity against L. major and L. tropica. The protective efficacy of Citrus limon was attributed to the presence of major constituents like 62% limonene, 17% sabinene, 3.1% trans-limonene oxide, and 2.3% cis-limonene oxide (Zarenezhad et al., 2020).

8.4.5 Antimicrobial and antifungal activity Citrus peels exclusively of lemon peels display a robust antimicrobial potential (Table 8.5) against microbes like Salmonella typhi, Pseudomonas aeruginosa, and Micrococcus aureus. It was

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8. Citrus essential oil (grapefruit, orange, lemon)

TABLE 8.5 Antifungal and antimicrobial activity of Citrus essential oils. Essential oil of citrus species Orange, bergamot, lemon

Orange, bergamot, lemon EO (Linalool)

Microorganisms/fungi

Effects

References

Arcobacter butzleri Escherichia coli , Klebsiella pneumoniae Mycoplasma pneumoniae, Mycoplasma fermentans

MIC > 4% MIC 0.6–5 mg/mL

Fisher et al. (2007) Sonboli et al. (2005)

MIC 0.03–1% (v/v)

Furneri et al. (2012)

MIC 0.06, 0.125, 0.25% (v/v) MIC 0.6–5 mg/mL

Fisher et al. (2007)

Arcobacter butzleri Staphylococcus epidermidis

Sonboli et al. (2005)

Orange, bergamot, lemon EO (Citral)

Campylobacter jejuni Staphylococcus aureus

0.03–0.06% (v/v)

Fisher and Phillips (2006)

Citrus aurantium

E. coli S. Typhimurium S. aureus B. cereus L. monocytogenes

20.1 mm (inhibition zone) 18.2 mm 21.53 mm 20.4 mm 20.8 mm

De girmenci and Erkurt (2020)

Citrus limon

E. coli Bacillus subtilis

MIC > 6.4 mg/mL MIC > 12.8 mg/mL

Prabuseenivasan et al. (2006)

C. reticulata

E. coli

16 mm inhibition zone

Sultana et al. (2012)

Orange, bergamot, lemon

Klebsiella pneumoniae Staphylococcus aureus

MIC 0.00125–0.050 mL/mL

Fabio et al. (2007)

Arcobacter butzleri

MIC > 4% (v/v)

Fisher et al. (2007)

C. limon

Aspergillus niger

10 mm

Souza et al. (2005)

C. sinensis (Orange)

A. flavus

100% inhibition at 750 ppm

Singh et al. (2010)

C. sinensis

A. fumigatu

100% inhibition at 750 ppm

Singh et al. (2010)

C. maxima

A. terreus

100% inhibition at 750 ppm

Singh et al. (2010)

C. sinensis

Penicillium chrysogenum

18.99 mm

Tao et al. (2009)

C. sinensis

P. expansum

34.9% inhibition at 2000 ppm

Van Hung et al. (2013)

C. limon

Rhizopus spp.

12 mm

Souza et al. (2005)

C. sinensis

Botryodiplodia theobromae, Myrothecium roridum

MIC ¼ 600 ppm

Sharma and Tripathi (2006)

C. sinensis

Mucor hiemalis

36.5% inhibition at 2000 ppm

Van Hung et al. (2013)

C. sinensis

Helminthosporium oryzae, Trichoderma viride

100% inhibition at 750 ppm

Singh et al. (2010)

8.4 Applications of citrus essential oils

205

observed that essential oil from the citrus peel revealed the antimicrobial action against Bacillus subtilis, Penicillium chrysogenum, S. aureus, and E. coli (Tao and Liu, 2012; Dhanavade et al., 2011). Citrus reticulata oil demonstrated strong antimicrobial potential against Staphylococcus aureus which is known for spreading food poisoning and purulent infections. It displayed irrevocable cellular impairment and this impairment was verified by enhanced cell membrane penetrability, more seepage of proteins, nucleic acids, and ATP. This study suggested that citrus essential oil can pierce the cell membrane of bacteria and kill S. aureus cells, thereby indicating its potential as a good natural microbicidal agent for the preservation of food (Song et al., 2020). In another study, supplementation of essential oil of C. limon showed a 100% decline in the multiplication of C. albicans. The essential oils of citrus showed protective efficacy against E. coli, B. subtilis, and P. multocida. Maximum inhibition was observed to be 18.21.3 against E. coli after treatment of C. pseudolimon oil. The lowest zone of inhibition against Escherichia coli was revealed by Citrus grandis (Sajid et al., 2016). Various studies demonstrated that the antimicrobial potential of citrus essential oils might be due to the presence of active compounds in them. It was observed that components present in essential oils give hydrophobicity which reveals a part in unraveling the phospholipid layer of the membrane of bacteria and the mitochondria, abolishing the integrity of cells and enhancing the permeability of cells. It leads to the wide seepage of essential molecules and ions from the surface of bacteria which cause their death (Prabuseenivasan et al., 2006). Raspo et al. (2020) reported that citrus essential oils contained the active compound limonene. Essential oils from grapefruit and lemon revealed robust antimicrobial potential against E. coli, and Lactobacillus plantarum. Denkova-Kostova et al. (2021) displayed that the essential oils showed potent antimicrobial potential against Staphylococcus aureus, Aspergillus flavus, Bacillus subtilis, Pseudomonas aeruginosa, Aspergillus niger, Salmonella abony, Fusarium moniliforme, Penicillium chrysogenum, Saccharomyces cerevisiae, E. coli, and Candida albicans with the maximum inhibition showed by cinnamon oil, followed by grapefruit, tangerine and lemon zest oil. Moreover, Ozogul et al. (2021) demonstrated that the essential oil of grapefruit peel has inhibitory activity against the growth of Salmonella parathypi A, Seratia liquefaciens, and Vibrio vulnificus at the concentration of 25 mg/mL. The essential oil of orange peel was observed to reveal effectiveness against Staphyloccocus aureus, Pseudomonas aeruginosa, Enteroccocus feacalis, E. coli, and fungi (Candida albicans) (Kirbas¸ lar et al., 2009; Obidi et al., 2013). The protective efficacy of Citrus essential oils was monitored against fungal strains through the disc diffusion technique. C. pseudolimon and C. grandis showed maximum inhibition against the Penicillium notatum and the zone of inhibition was observed to be 25.7  0.75 mm and 130.29 mm respectively (Sajid et al., 2016). The active constituents such as pinene, linalool, and terpineol in the essential oil of C. pseudolimon and C. grandis are responsible for antifungal (Table 8.5) and antibacterial activity (Vasudeva and Sharma, 2012; Asbahani et al., 2014).

8.4.6 Insecticidal activity Essential oils of orange peel at the concentration of 33.33 μL/L showed 74% mortality in Acyrtosiphon pisum and Rhopalosiphum padi, 54%–60% in Macrosiphum euphorbiae and Aphis fabae respectively. The 50% lethal concentration was observed to lie between 16.12 and

206

8. Citrus essential oil (grapefruit, orange, lemon)

31.27 μL/L for A. pisum and A. fabae respectively. It revealed the significance of essential oils of orange peels as a substitute to synthetic pesticides (Chaieb et al., 2018). Campolo et al. (2017) monitored the lethal and sublethal potential of essential oils extracted from citrus peel against the Tuta absoluta which is a tomato pest. It was observed that essential oils of citrus peels revealed a remarkable insecticidal effect with a significant death rate. The nano-formulation of essential oils of citrus also markedly decreased the noticeable noxious effects on the herbs. Likewise, the essential oil of orange was examined against houseflies and contact toxicity and fumigation bioassay revealed the 50% of the lethal concentration of the essential citrus oil against larvae was observed to be in the range between 3.93–0.71 L/cm2 and 71.2–52.6 L/L. The percentage inhibition of the citrus oil was found to be 27.3%–73% and 46%–100% against housefly pupae found by contact toxicity and fumigation assay respectively (Kristensen and Jespersen, 2003). In another study, Sanei-Dehkordi et al. (2016) revealed the larvicidal action of Citrus aurantium and Citrus paradisi oil against Anopheles stephensi and 50% of lethal concentration was observed to be 31 ppm and 36 ppm, respectively. Oboh et al. (2017) demonstrated that orange peel oil displayed significant potential against Tribolium confusum, Sitophylus oryzae, and Callosobruchus maculatus. It was found that mortality in these insects was enhanced with an increment in the concentration and exposure of orange peel oil. LC50 of orange peel oil against T. confusum was observed to be about 39 L/L, 27 L/L, and 14.5 L/L after the treatment of 24–72 h respectively. The insecticidal Potential of citrus oils was found to be enhanced against C. maculatus and showed 100% mortality at higher concentrations 100–150 L/L and LC50 was observed to be 17.8 L/L and 10 L/L after the incubation of 48–72 h, respectively. A similar pattern of insecticidal activity was shown by citrus oil against S. oryzae and LC50 was observed to be 29.51 L/L. It was observed that citrus essential oils displayed more insecticidal potential against T. confusum and C. maculatus in contrast to S. oryzae. The biochemical investigation showed that the citrus essential oils can hamper the action of acetylcholinesterase and Na/K-ATPase. It indicates that the essential oil of orange peel can play a crucial role in the control of T. confusum, C. maculatus, and S. oryzae.

8.5 Future concerns and perspectives The use of citrus essential oil for the preservation and safety of food eradicates the requirement of artificial additives. However, few issues limit the usage of citric essential oil and consumer’s acceptance. For instance, the citric essential oil can be employed for the preservation of meat and fish, but the active volatile constituents of essential oil amalgamate with the proteins and yield undesirable complexes (Mahato et al., 2019). Further, more research is required to detect how the citrus essential oil and its components react with the food matrices (Chouhan et al., 2017). It was observed that more volume of citric essential oil changes the flavor of food which affects the superiority and acceptance of consumers, subsequently, citric essential oil at low concentration gives an improved taste and fragrance. Additionally, intake of citric essential oil is considered to be innocuous, less-allergenic, and safe, but it induces irritation of skin and allergies in few cases. This problem can be solved by the encapsulation of citric essential oil with appropriate green coating materials that can release

References

207

the precise amount of biologically active constituents to the target site. Moreover, the quantity and composition of citric essential oil play a huge role in the wrapping and preservation of different food matrices. Thus, future studies should be carried out to find the efficient green extraction techniques of citric essential oils, safe concentration limits, allergic reactions, and their influences on the quality and safety of food. In addition, bioanalytical techniques related to recombinant technology can be explored to grow disease-resistant citrus plants (Caserta et al., 2019).

8.6 Conclusion Therefore, the isolation of oils from the citrus waste peel is an efficient approach that reduces environmental pollution and is also employed for various food and medicinal applications. Citrus essential oils are eco-friendly, cheap, and natural substitutes to artificial additives for the safety and preservation of food. However, there is a continuous need to give attention to find the safe dose limits of citric essential oil, its probable allergic responses, and numerous green innovative techniques for the isolation of oil. Further comprehensive experimentation of citric essential oil is required to ensure the safety and security of food.

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Xiong, K., Chen, Y., 2020. Supercritical carbon dioxide extraction of essential oil from tangerine peel: experimental optimization and kinetics modelling. Chem. Eng. Res. Des. 164, 412–423. Yang, L., Sun, X., Yang, F., Zhao, C., Zhang, L., Zu, Y., 2012. Application of ionic liquids in the microwave-assisted extraction of proanthocyanidins from Larix gmelini bark. Int. J. Mol. Sci. 13 (4), 5163–5178. Yang, C., Chen, H., Chen, H., Zhong, B., Luo, X., Chun, J., 2017. Antioxidant and anticancer activities of essential oil from Gannan navel orange peel. Molecules 22, 1–10. Yi, F., Jin, R., Sun, J., Ma, B., Bao, X., 2018. Evaluation of mechanical-pressed essential oil from Nanfeng mandarin (Citrus reticulata Blanco cv. Kinokuni) as a food preservative based on antimicrobial and antioxidant activities. LWT- Food Sci. Technol. 95, 346–353. Yu, L., Yan, J., Sun, Z., 2017. D-limonene exhibits anti-inflammatory and antioxidant properties in an ulcerative colitis rat model via regulation of iNOS, COX-2, PGE2 and ERK signaling pathways. Mol. Med. Rep. 15 (4), 2339–2346. Zapata, R.B., Villa, A.L., de Correa, C.M., Williams, C.T., 2009. In situ Fourier transform infrared spectroscopic studies of limonene epoxidation over PW-Amberlite. Appl. Catal. Gen. 365 (1), 42–47. Zarenezhad, E., Agholi, M., Ghanbariasad, A., Ranjbar, A., Osanloo, M., 2020. A nanoemulsion-based nanogel of Citrus limon essential oil with leishmanicidal activity against Leishmania tropica and Leishmania major. J. Parasit. Dis., 1–8. Zema, D.A., Calabro`, P.S., Folino, A., Tamburino, V.I.N.C.E.N.Z.O., Zappia, G., Zimbone, S.M., 2018. Valorisation of citrus processing waste: a review. Waste management 80, 252–273. Zhang, H., Lou, Z., Chen, X., Cui, Y., Wang, H., Kou, X., Ma, C., 2019. Effect of simultaneous ultrasonic and microwave assisted hydrodistillation on the yield, composition, antibacterial and antibiofilm activity of essential oils from Citrus medica L. var. sarcodactylis. J. Food Eng. 244, 126–135. Zhu, T., Zhao, Y., Zhang, J., Li, L., Zou, L., Yao, Y., Xu, Y., 2011. ss-Elemene inhibits proliferation of human glioblastoma cells and causes cell-cycle G0/G1 arrest via mutually compensatory activation of MKK3 and MKK6. Int. J. Oncol. 38 (2), 419–426.

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9 Eucalyptus essential oils Rabia Shabir Ahmad, Muhammad Imran, Muhammad Haseeb Ahmad, Muhammad Kamran Khan, Adeela Yasmin, Hafiza Saima, Khadija Abbas, Rabbiya Chaudhary, and Muhammad Abdul Rahim Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan

9.1 Introduction Scientists and environmentalists across the world are interested in eucalyptus plants as they are a rapid-growing supply of timber, while a source of oil that can be utilized for a variety of reasons. The oil is obtained from leaves, buds, bark, and fruits, it has antibacterial, antioxidant, antiseptic, antiinflammatory, and anticancer properties, thus it is used to treat respiratory illnesses like sinus congestion, influenza, and the common cold (Vecchio et al., 2016). Eucalyptus essential oils have been utilized for over 5000 years in folk medicine. Eucalyptus essential oils are also known as ethereal or unstable oils which is a fragrant oil derived from various plant ingredients and is mostly used as a dietary flavoring. This volatile oils have antioxidant, antibacterial, insecticidal, antiviral, and other biological properties. The oils have been used as a flavor agent in the food preservation, aromatherapy and cosmetic industries. These oils are widely used for its excellent antiseptic and antioxidant properties, such as preserving processed and fresh foods from oxidation and is used as an alternative medicine for many purposes. Furthermore, it is used in essential oil therapy as a substitute technique of repair the wound due to its fragrant chemical content. It is also used for relaxation. However, this information is not included in the report (Seymour, 2003). There are around 700 species of Eucalyptus, and more than 300 of them have volatile oils in their leaflets. The cosmetics, toiletry, pharmaceutical, and food sectors all utilize essential oils from a variety eucalyptus species. The antibacterial, antihyperglycemic, antioxidant, antiinflammatory and flavoring characteristics of the chemicals in the oil lead to their Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00005-0

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numerous uses. The antibacterial action of essential oils has been discovered to differ greatly between various species of microorganism and their linear strains (Boukhatem et al., 2020). Eucalyptus essential oils offer a wide range of medical and commercial applications. They are used as painkiller, antiperiodic, anodyne, astringent, antiphlogistic, antibacterial, disinfectant, antiperspirants, expectorant, fumigant, febrifuge, hemostatic clamp, insect repellent, inhalant, preventive, suppurative, rubefacient, sedative yet stimulating, vermifuge, and tonic. Its nine species are utilized both medicinally and commercially. Other treatments are E. cinerea and E. cneorifolia are curative plants, and E. macarthurii which is used in fragrance (Darji et al., 2021). The high antibacterial action might be due to the oil’s key components (such as α-pinene and 1,8-cineole) or interaction among the foremost and insignificant components. According to previous findings, gram-positive bacteria pathogens are relatively sensitive procedure to gram-negative bacteria, and action alongside fungus and Saccharomyces cerevisiae and Candida albicans has also been found. Eucalyptus odorata has the highest antibacterial and yeast action, while E. bicostata has the highest antiviral activity (Damjanovi
c-Vratnica et al., 2011). Although there have been numerous studies on eucalyptus oils, only a few of them have tested their effectiveness against pathogenic and food spoilage bacteria. Despite their antibacterial action in vitro, eucalyptus vital oils are mostly used as flavoring agents in food sector. As a result, the use of essential oils is restricted as food preservatives. Since the relations of the essential oils components with the chemical interaction between compounds impact the necessary concentration against bacteria, larger concentrations are required to obtain adequate activity. This has a detrimental influence on the organoleptic characteristics of the finished products. A viable option to this problem is to use of a mixture of lower temperature therapy with eucalyptus oils. In fact, a modest heat treatment improves the antimicrobial effectiveness of the essential oil by modifying vapor pressure of the molecules (Safaei-Ghomi and Ahd, 2010). The antiviral activity of eucalyptus essential oils against mumps, adenovirus, and herpes simplex viruses has been shown in a few studies. The practical use of these essential oils in vivo studies is one of the key problem. This is challenging and trial experiments must be used to overcome it. The antiviral activity of natural chemicals is significant because of their potential use against these diseases. Enteroviruses are much more common in the environments as compared to the viruses described above, so it’s worth researching them to see whether they have any antiviral properties (Usachev et al., 2013). By utilizing the disc diffusion technique to observe the antimicrobial activity of 35 eucalyptus essential oils toward four reference gastrointestinal microorganisms (Pseudomonas aeruginosa, ATCC 227853, Escherichia coli, ATCC 25922, Staphylococcus aureus, ATCC 25932, and Enterococcus faecalis, ATCC 292112). Eucalyptus essential oils of eight eucalyptuses were considered for their action which was not in favor of bacterial strains derived from patients with respiratory illnesses based on the greatest diameter inhibition against such pathogens. These oils were also evaluated for antifungal properties (Silva et al., 2003; Kumar et al., 2007; Sartorelli et al., 2007). Eucalyptus essential oils has excellent biological, pharmaceutical, and medicinal properties that are very useful for many purposes.

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9.2 Eucalyptus essential oil history In all over the world, 700 varieties of Eucalyptus tree are found and it is marketed as a cure-all medicine. It is considered to be an effective treatment for respiratory infections. As mentioned, eucalyptus is native to Australia, with a limited number also found in Indonesia and New Guinea. Eucalyptus was first identified in 1642. The word eucalyptus is derived from the Greek terms eu, which means lovely, and kalyptos, which means hat, because the pistils and stamen resemble a hat (Govindan, 2002).

9.3 Some important types of eucalyptus essential oil In recent years, the interest of people in these essential oils has increased exponentially and becoming one of the most popular natural health products on the market. These essential oils are great source of fragment, as well as their potential to do anything from treat skin issues and relieve anxiety to clean the home. Not surprisingly, these small bottles of essential oil are currently in high demand. For a variety of reasons, eucalyptus essential oil is one of the most helpful and widely used oil. However, since it comes in so many types, it can be difficult to determine which eucalyptus will be best suited to the demands. The eucalyptus tree is found in hundreds of varieties, yet humans have just discovered the best ways to use a few of them. One of the most important variables in the essential oil of each eucalyptus oil is a chemical compound called cineol or eucalyptol. Cineol has powerful therapeutic potential and a fresh minty scent, making it ideal for fragrance, flavoring, and medical applications., on the other hand, the health effects of high dosages have been found, so the type of eucalyptus used in each product should be carefully selected. Most common types of eucalyptus are Eucalyptus globulus, Eucalyptus polybractea, Eucalyptus radiata, and Eucalyptus citridora (Clarke, 2009).

9.3.1 Eucalyptus globulus (blue gum) Eucalyptus globulus most common type of eucalyptus contains between 60% and 85% cineol. Cineol has the eucalyptus fragrance properties that are very strong, rich, and sharp, it is used for a variety of medicinal purposes such as, expectorant, decongestant, and antiinflammatory. As a result, blue gum eucalyptus is a natural component that is used against germs, clarifying the mind, relieving respiratory pain, and calming restless muscles. Gum is found in a variety of products such as, topical muscle rubs, mouthwash, and bath salts. Furthermore, blue gum eucalyptus is not recommended for use a large amount in products designed for children under the age of six, as it contain high concentration of cineol which is not good for children health (Skolmen and Ledig, 1990).

9.3.2 Eucalyptus polybractea (blue mallee) Blue mallee oil is the most powerful eucalyptus essential oil which contain a high amount of eucalyptol. Therefore, blue mallee oil is used as medicine for multiple purpose but it also

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needs dilution before use; may cause disorders in some individuals. Blue mallee oil is used as antiseptic, antibacterial, antioxidant, and antiviral to stimulate the immune system, reducing the body pain, clear the respiratory problems and claiming the nervous system. It is also used in pharmaceutical formulations with complementary oils such as peppermint, lemon, and rosemary. Because of blue mallee oil high cineole content, it is recommend avoiding use of this oil with elders, epileptics, pregnant, nursing women, and children under age 18 (Milthorpe et al., 1998).

9.3.3 Eucalyptus radiata (Eucalyptus radiata) This softer and milder form of eucalyptus is therapeutically flexible and ideal for children and individuals with delicate health issues. It has a pleasant, cooling, and zesty fragrance. Eucalyptus radiata oil is frequently used in products aimed at strengthening the immune system, facilitating clean breathing, and energizing a fatigued mind and body (Luı´s et al., 2016).

9.3.4 Eucalyptus citridora (lemon eucalyptus) This distinctive type of eucalyptus has a rosy lemon-citronella, and a sweet fragrance, as well as all of the highly beneficial medicinal properties of eucalyptus. It can combat fungus and germs, alleviate respiratory problems, and cleanse the air to destroy bacteria. Lemon Eucalyptus is also an extremely efficient and harmless insect repellent. This oil works well in room mists, insect’s sprays, skincare oils, and lotions (Han et al., 2011).

9.4 Production and composition 9.4.1 Production The majority of eucalyptus plantation in Brazil is dedicated to the manufacture of paper and charcoal however; its utilization in logging, building, and for essential oil extraction is also expanding. In a research trial 11 eucalyptus species were evaluated for their essential oil extraction potential, nine of which had never been used for commercial essential oil production before. The results were compared to those of Eucalyptus globulus and Eucalyptus citriodora, which have already been studied extensively for oil production for fragrances and medicines. The main objective of this study was to understand the link between oil and gas production and climatic factors as well as to increase the availability of moneymaking species (Silva et al., 2006). In a related study, seasonal samples of eucalyptus leaves were taken (at 3-month intervals) for distillation and assessment of oil extraction ability. The largest potential for cineol was found in Eucalyptus viminalis, which stood out among all yet it is not employed commercially for this purpose. The minimum and maximum oil production was recorded in spring and summer, respectively, as a result of soil humidity content and air temperature. The lowest oil output may be attributed to the lack of water in the spring season. Contrarily, during summer, maximum oil output is due to increased temperature and water availability.

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Interestingly, primary oil chemical composition remained unaffected by weather conditions (Kringel et al., 2017).

9.4.2 Composition Eucalyptus (family: Myrtaceae) is a large class native to Tasmania and Australia with around 800 species, hybrids and subspecies. Members of this genus are recognized as a significant pool of a large variety of substances, in which most of them have a wide range of biological activities. Essential oils are extracted from different varieties of Eucalyptus including E. robusta, E. alba, E. camadulensis, E. citriodora, E. globulus, E. saligna, E. baueriana, E. pulverulenta Sims, E. erythrocorys, E. microtheca, and E. oleosa with varied chemical compositions. Following is a brief and comprehensive discussion on essential oil composition of E. oleosa (Su et al., 2006). 9.4.2.1 E. oleosa essential oils The E. oleosa stems, fruits, adult leaves, and immature flowers yield about 0.52%, 1.12%, 0.45%, and 0.53% of essential oil, respectively. According to the literature, oil yields from leaves of E. oleosa collected in Sahara’s of north Africa in winter were 4.45%. moreover, the essential oil content of E. oleosa from north Africa research center was 2.25% higher than those from south. The disparities among overall eucalyptus oil output of species growing throughout research center may be associated to dust and environmental parameters, environmental factors, growth and harvest time of plant (Marzoug et al., 2011). 9.4.2.2 E. oleosa stems essential oil Approximately 40 different compounds were identified in the essential oil pulled out from E. oleosa stems, accounting for 98.8% of the entire essential oil. Furthermore, 84.0% of total terpene derivatives were found in the essential oil of stems as sesquiterpenes (18.5%) and monoterpenes (65.5%). When compared to monoterpene hydrocarbons, (52.9%) oxygenated monoterpenes (12.6%) were the most frequent ones. Additionally, out of sesquiterpenes, oxygenated species have been found in a larger percentage (16.7%) as compared to hydrocarbons (1.8%). The major components in the essential oil of E. oleosa stems were transpinocarveol (9.9%), 1,8-cineole (31.5%), pinocarvone (3.5%), y-eudesmol (5.6%), spathulenol (3.5%), and limonene (4.2%) (Marzoug et al., 2011). 9.4.2.3 E. oleosa leaves essential oil E. oleosa leaf essential oil contained 38 compounds, accounting for 99.1% of the total oil content. Sesquiterpenes were nearly twice as abundant as monoterpenes in the essential oil pulled out from mature leaves (44.3% and 28.7%, correspondingly). The major oxygenated sesquiterpenes in leaf essential oil were y-eudesmol (25%) and spathulenol (16.1%) accompanied by p-cymene (10.6%), p-cymen-8-ol (4.4%), 1,8-cineole (8.7%), cis-sabinol (4.2%), verbenone (3.7%) and p-cymen-7-ol (4.0%) (Franco et al., 2014).

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9.4.2.4 Essential oil of E. oleosa fruits The eucalyptus oil extracted from the fruit further comprised of 51 components in total. Among these sesquiterpenes cover 45.7% of the total, while 40.4% are monoterpenes while, oxygenated monoterpenes contributing the most (35.9%). The major components in fruits essential oil were 1,8-cineole (29.1%), y-eudesmol (16.4%), α-selinene (10%) and p-cymene (9.0%) (ben Marzoug et al., 2010). Essential oils from various regions were shown to be more efficient against Gram-positive bacteria when compared to Gram-negative. Many investigations on further plant species, such as E. citriodora, E. robusta, E. camadulensis, E. alba, E. globulus, E. saligna, E. globulus, etc. came to the similar conclusion. As gram-negative bacteria have a different cell membrane than those of gram-positive bacteria, which might explain their high resilience. Diderm bacteria have a surface covering that surrounds the plasma membrane and prevents hydrophobic substances from diffusing through the lipopolysaccharide coating. Without this membrane, the active transport, electron movement, proton motive force, and coagulation of the cell components in Gram-positive bacteria can be disrupted more effortlessly (Mulyaningsih et al., 2011). The eucalyptus oils from leaves sampled in October 2007 in south east of Lebanon and Tunisia showed promising antibacterial action against all pathogens apart from S. aureus and E. coli. The season of harvest as well as the age of the samples are most likely responsible for the substantial variation. Eucalyptus oils from various sections of this species are believed to have antibacterial effects due to their maximum concentration of various organic molecules. Antimicrobial action is found in α-pinene, 1,8-cineole, sphathulenol, and p-cymene. Other minor components in eucalyptus essential oils, like carvacrol, borneol, limonene, y-terpinene, myrtenal, camphene, and cuminaldehyde are also known to have effective antibacterial activities (Rahimi-Nasrabadi et al., 2013).

9.5 Techniques One of the important elements that might alter the chemical composition of essential oil is its method of extraction. As essential oils are an unstable odorant multipart mixture produced by distillation. An essential oil may be pulled out using a range of processes, including microwave-assisted extraction, solvent extraction and expression. Essential oils are highly concentrated compounds resulting from flowers, leaves, roots, stalks, barks, resins, seeds or fruit rinds of plants. These oils are frequently exploited in a range of products for their flavor and medicinal or odoriferous characteristics, including meals, medications, and cosmetics. The extraction of essential oils is one of the most time-consuming and labor-intensive procedures. Hence, it is critical to understand how oils are extracted from plants since certain methods utilize solvents that might damage their desired medicinal properties. There are numerous techniques for extracting essential oils, but their effectiveness may vary. Many scientists have explored the method of extracting oils from different segments of plants using the “Steam Distillation” method, which is the most lucrative approach. The steam is suitable to travel across the extraction chamber, which include plant resources, throughout this procedure. When steam is forced through the plant material, the cells weaken and the essential oil

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escapes in vapor form. These vapors are directed to flow through the condenser, eventually, the oil is collected and separated in a separating funnel. According to researchers, eucalyptus oil may be utilized as a cosolvent, resulting in decreased cloud point temperature (Saoud et al., 2006; Abed et al., 2015; Ho et al., 2020).

9.5.1 Extraction strategies Resultant metabolites generated by flowers in reaction to pathogens, parasites and diseases are known as essential oils. Eucalyptus oils are volatile chemical molecules obtained from fruits, flowers, seeds, wood, roots, and barks. They are, however, mostly derived from plants. There are five different extraction methods:

9.5.2 Hydro-distillation For this procedure, plant fibers placed in a container full of water, which is then heated at low temperature. Heat-sensitive aroma, which condenses into a fluid containing a little amount of water. The oil output towers as the distillation time increases however the precept component (percent) decreases, correspondingly. To extract essential oil from the leaves of Eucalyptus, traditional techniques such as solvent extraction (SE), hydrodistillation (HD), a new supercritical carbon dioxide (SC-CO2) extraction, and ultrasonic-assisted extraction (UAE), strategy were employed. HPTLC (high-performance thin layer liquid chromatography) and FTIR (Fourier transform infrared spectroscopy) fingerprinting were used to evaluate each oil, and gas chromatography–mass spectrometry was utilized to establish the semiquantitative and qualitative and composition of the extracted essential oil (GC–MS) (Singh et al., 2016; Singh, 2016).

9.5.3 Steam distillation This method requires inserting plant sample inside a 500 mL of volumetric flask. After that, pushing and heating the plant fibers to evaporate the unstable components in the oils. This method is worked similarly like hydro distillation method (Kumar, 2010).

9.5.4 Vacuum distillation Vacuum distillation at reduced temperatures is used to extract essential oils from various eucalyptus species, avoiding changes in essential oil chemical composition at some point during the distillation process (Inman et al., 1991).

9.5.5 Supercritical fluid extraction (SFE) It makes use of the capacity of particular gases to work as nonpolar solvents at specific temperatures and pressures (typically CO2). It is highly environment friendly and more rapid technique than hydro distillation (Della Porta et al., 1999; Singh et al., 2016).

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9.5.6 Subcritical-water extraction (SWE) High temperature and pressure are used as extractants. It is both faster and more costeffective than hydro distillation. Advantages include shorter extraction times, higher extract quality, reduced costs and biodegradability ( Jim
enez-Carmona and Luque De Castro, 1999).

9.5.7 Microwave-assisted essential oil extraction (MAEOE) MAEOE is a variation of the commercial process in which the energy source is replaced with a microwave instead of the traditional electric heating cap. The advantage here is the hypothetic improvement in pulled out oil yield. Although crushing plant material is preferred, however when compared to the classical distillation, the eucalyptus oil output is approximately the similar. The basis of the technique is the polarity of water being changed by waves, as well as heating, which will serve the same function as in traditional distillation. In addition to the limitations of traditional distillation, microwave can cause chemical change from one isomer to another (Tran et al., 2020).

9.6 Characterization and identification of essential oil components by techniques like NMR-13C A combination of (GC-IRFT, GC(RI), GC–MS, HPLC-MS) these methods are widely used to analyze natural mixtures. In an innovative procedure, 13C NMR spectroscopy might be utilized to identify specific components of complicated mixtures without having to separate them (resins, vegetable oils, essential oils, extracts,). An experimental method was devised on computer-aided interpretation of the 13C NMR spectrum of the mixture, which enables the recognition of the major components of essential oils and extracts. A variety of essential oils have been studied using this technology that have components with diverse structures and roles. This approach allows the precise recognition of terpenes in essential oils (including diastereoisomers, stereoisomers, as well as other compounds with inadequately determined mass spectral patterns or that co-elute on GC, as well as thermo labile substances) and solvent extracts. The use of 13C NMR for the explicit identification of unique terpenes found in essential oils from family labiatae, as well as its effectiveness and comparison with traditional methods, has also been explored (Tomi and Casanova, 2006). Individual component extraction from essential oils for NMR study is challenging, timeconsuming, and impractical for complex oils. However, NMR essential oil assessment as a mixture is difficult because the possibility of overlaying chemical shifts rises with the complexity of the mixture. Furthermore, due to background superposition, many of the absorptions of chemicals present in low yields are undetectable. This explains why 13C NMR spectroscopy is commonly used to identify and determine the structure of pure substances but is seldom utilized when the analytic is a complex combination like an essential oil. It is also documented that volatile oils compositional analysis only by using mass spectroscopy might cause difficulties, necessitating the use of additional spectroscopic data to supplement

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it. The 13C NMR procedure technique compares every carbon chemical shift hybridization to the same parameters recorded in libraries of mono and sesquiterpenes. The FoxPro for Windows language is used to write computer programs that compare experimental 13C NMR oil chemical shifts and carbon hybridization (Alencar et al., 1997).

9.7 Eucalyptus essential oil chemistry and properties Although eucalyptus trees are extensively cultivated across the world, Australia may be the only place where a single species dominates the landscape. Its essential oils have a wide variety of medicinal and economic applications. Eucalyptus leaf extracts have been permitted for use as additives in food and cosmetic formulations. These functional properties of extracts have recently captured a lot of popularity. According to previous investigation, the extracts were found to have antioxidant, antihyperglycemic, and antibacterial properties. The reason for this study was to elaborate the chemical formation of essential oils from three eucalyptus types widely found in Australia: E. dives, E. olida, and, Eucalyptus staigeriana as well as their antibacterial properties on some of the most severe infections and bacterial food spoilage (Waterman, 1996).

9.7.1 Chemical makeup The oil content of several eucalyptus species is being explored since 1998. The number of components discovered to increase 1,8-cineole concentration and the key components in the essential oils of the unusual eucalyptus species have been presented in various studies. The major components are monoterpenes and sesquiterpenes. Though, the chemical makeup and major components of eucalyptus leaf oils vary considerably. In eucalyptus oils, the proportion of 1,8-cineole ranges between 10% and 90% (Sefidkon et al., 2008).

9.8 Essential oil yield Eucalyptus oil production from leaves varies from 0.10% to 9% depending on the variety of analyzed. The production of eucalyptus oils is influenced by a variety of factors, including tree age, leaf maturity level, altitude, climate, harvest time, and fertilizer treatment. The oil content of younger leaves is higher than that of older leaves, although the oil content of elder tree leaves is somewhat higher. The effect of altitude on oil production is greater than the effect of age. Eucalyptus citriodora leaves collected in Pakistan from April to May contained 0.9% oil content which was 1.3% in December. Between January and July, substantial volumes of eucalyptus oil were extracted in central Thailand. The fertilizers application including nitrogen, potassium, and phosphorus boosted essential oil output of eucalyptus (Kakaraparthi et al., 2011).

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9.9 Functional applications of Eucalyptus essential oil 9.9.1 Aromatherapy Eucalyptus oils have been utilized to change and stimulate nervous system to modulate the symptoms of neuralgia, debility and headaches. In this connection, immunity to flu, measles and chickenpox is boosted by the immune mechanism. It can also be used to treat leucorrhea, throat infections, coughs, catarrh, bronchitis, sinusitis, and bronchial allergies caused by respiration machines. It may also be used to treat skin problems such as wounds, burns, cuts, herpes, bug bites, lice, and may also be employed as insect repellant. The essential oils of this plant are effective in the treatment of muscle and joint problems, rheumatoid arthritis and body aches. Similarly, research has proven that eucalyptus oil contains antioxidant, antiproliferative, antiinflammatory, and antibacterial properties and that it is effective in the treatment of a variety of metabolic and infectious diseases. The findings are intriguing and might be used to treat a variety of multifactorial ailments in people (Dhakad et al., 2018).

9.9.2 Antimicrobial properties Eucalyptus essential oils from three most regular Australian eucalyptus type, such as E. olida Eucalyptus staigeriana, and E. dives, have exhibited antiseptic characteristics. It was confirmed using agar disc diffusion and gas chromatography/mass spectrometry procedures, correspondingly. When compared to different strains tested, eucalyptus essential oils demonstrated varying degrees of antibacterial activity. The Staphylococcus aureus and Candida albicans were presented naturally in the eucalyptus essential oils, whereas P. aeruginosa was found to be the most resilient gram-negative spoilage-causing bacteria. The antibacterial activity of essential oils differed significantly among various eucalyptus species, including E. dives, Eucalyptus staigeriana and E. olida. Against all the microorganisms, the eucalyptus oil of Eucalyptus staigeriana demonstrated the maximum activity. Additionally, when tested alongside pathogenic S. aureus, E. dives depicted much higher activity than E. olida. Subsequently, when compared to yeast C. albicans and gram-positive E. faecalis; the other two eucalyptus species showed similar antibacterial efficacies. Although there was no inhibitory action in the essential oils from E. oilda, when it was used to treat Pseudomonas aeruginosa. Antibacterial action of eucalyptus oils, particularly those from Eucalyptus staigeriana and blue peppermint, was recorded to be significantly higher than that of conventional antibiotics. As a result, the findings of the testing of the conventional antibiotic between the eucalyptus essential oil of Eucalyptus staigeriana and E. dives were extremely promising (Gilles et al., 2010; Ghalem and Mohamed, 2014). The Gram-negative spoilage bacteria Pseudomonas aeruginosa was observed as more resistant to essential oil testing, whereas oils from E. olida showed no antimicrobial action against this bacterial specie. Similarly, oils from E. dives and Eucalyptus staigeriana revealed relatively mild inhibition (5–10 mm). Hence, Pseudomonas aeruginosa has a high level of intrinsic resistance to a variety of antimicrobials and antibiotics. Owing to the occurrence of a relatively limited outer barrier layer, it is extremely resistant to synthetic medicines (Damjanovi
cVratnica et al., 2011).

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Although the essential oils from these three eucalyptus species have strong antibacterial action against the yeast Candida albicans; Eucalyptus staigeriana oil has the strongest antibacterial activity, with inhibition zone diameter of 25.9 mm. The presence of chemicals that give antimicrobial resistance is most likely responsible for the comparatively strong antibacterial activity of Eucalyptus staigeriana with a smaller amount of broad-leaved peppermint essential oils. In this regards; 1,8-cineole (eucalyptol), comprising around 31% of the essential oil from Eucalyptus staigeriana is particularly noteworthy. As it has been discovered to have rather significant antibacterial effects against a variety of decay causing pathogens, including S. aureus, E. coli, Fusarium solani, and Bacillus subtilis. Additionally, the essential oil from Eucalyptus staigeriana, known as Geraniol has a two to nine times greater antibacterial activity against Staphylococcus aureus than 1,8-cineole. It might be possible to make a vital impact on the antibacterial action of eucalyptus essential oil. Linalool, c-terpinene, a-pinene, a-terpineol, and p-cymene, are examples of compounds with antibacterial properties. The eucalyptus essential oil of E. dives included a sum of 22 components, the most important of which were piperitone, terpin-4-ol, and p-cymene. There were 26 chemicals identified in Eucalyptus staigeriana, with 1,8-cineole, geranial, a-phellandrene, neral, and methyl geranate being the most abundant. Conclusively, gram-positive bacteria were found to be more sensitive to eucalyptus essential oils than gram-negative bacteria (Smale et al., 2000).

9.9.3 Antifungal activity Numerous studies have documented the antifungal properties of essential oil from E. citriodora specie. The antifungal action of this specie is mostly prominent against Trichophyton mentagrophytes, Microsporum nanum, and Trichophyton rubrum fungi. It proved more effective for mammalian skin than commonly used synthetic antifungal medications up to a concentration of 5% without any negative side effects. Because the volatile oil of E. citriodora has been used as an antimycotic ointment, it has clinical use in dermatopharmacy. Other species with antibacterial and antifungal properties consist of Swamp messmate, Setosphaeria rostrata, Eucalyptus tereticornis, Eucalyptus camaldulensis, Eucalyptus citriodora, and Eucalyptus globulus. Furthermore, Eucalyptus citriodora has antifungal properties, making it resistant to mildew and timber decay fungi. However, Microsporum gypseum, Epidermophyton floccosum, and Trichophyton rubrum are all susceptible to E. dalrympleana’s antifungal properties (Boukhatem et al., 2020). One of the types of eucalyptus is Eucalyptus camaldulensis Dehnh. Known for its general name of river red gum, it is native to Australia. It is a very adaptable tree that can withstand drought and fluctuations of salt content in the soil. It is a fast growing medium sized tree that can reach a height of 25–30 m and a width of about 1 m at breast height however, it can be as tall as 50 m in height. Several extracts from E. camaldulensis have been showed as having antifungal properties not only in various pharmacological but also in phytochemical tests. Antifungal activity of E. camaldulensis extracts (organic and aqueous) against Fusarium solani has been well documented. In this regard, the solvent extract of river red gum has been shown to be more effective than Alternaria alternate fungus, a phytopathogenic fungi that cause leaf mark and further illnesses on more than 380 type. River red gum eucalyptus oil has been analyzed for its antifungal activity toward a diverse range of economically important

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phytopathogenic fungi such as green mold, C. gloeosporioides, R. solani, saprophytic mold, Cochliobolus heterostrophus, Pythium ultimum, sorokiniana, Fusarium Sporothrix fungus, and Fu€ uner et al., 2018). sarium graminearum (USt€

9.9.4 Insecticidal activity Eucalyptus species, belonging to the Myrtaceae family, are indigenous to Australia and Indonesia, with highly valued essential oils contents. Volatile chemicals found in their leaves include a- and p-pinene, terpineol, globulol, and 1,8-cineole (CIN). The 1,8-cineole (CIN) is the main monoterpene in most eucalyptus species. These essential oils also possess antimicrobial, antiviral, antifungal, and insecticidal properties, hence they are used for fumigant insecticidal action against insects’ pests of stored commodities. A study in 2004 showed the fumigant toxicity of 42 type of Myrtaceae family against stored commodities pests like red flour beetle, rice weevil, and lesser grain borer (Russo et al., 2015).

9.9.5 Antioxidant activity Eucalyptus essential oils also function as antioxidants and have radical scavenging abilities due to the presence of phenolic components. Pertaining to their antioxidant properties, they can also result in a variety of promoted chemical defense reactions. Antioxidant properties of the E. camaldulensis and Eucalyptus staigeriana species has been well established (Zhao et al., 2008).

9.10 Eucalyptus essential oils application in pharmacological, agro food, and nonfood products Essential oils with substituted phenols (carvacrol, thymol, eugenol, and guaiacol) have powerful antibacterial and antioxidant properties. The antifungicidal, antiseptic, and antiseptic properties of the eucalyptus have been well recognized for hundreds of years. Eucalyptus essential oil is one of the most widely traded oils on the planet. Eucalyptus oil is also higher in quality and has advantages over other essential oils because it has multiple applications in perfumery, pharmaceuticals and other industries. It exhibits therapeutic, fragrance, flavoring, antibacterial, antifungal, antimicrobial, and bio-pesticide characteristics (Olawore and Ololade, 2017).

9.10.1 Eucalyptus oils use in pharmaceuticals Eucalyptus essential oil is often used in various fields, mostly natural medicine and integrative therapies. Essential oil is a healing plant used to cure colds, flu, pyrexia, diabetes plus bronchial infections, as well as to prevent and control various damaging illnesses. Eucalyptus oil-based products are utilized as a topically administered medicine to alleviate muscle discomfort, as well as a solvent/sealer or disinfectant in dentistry. The bioactive components

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discovered in eucalyptus essential oils might lead to the development of novel analgesic and antiinflammatory medicines (Olawore and Ololade, 2017). (a) Treatment of allergy Eucalyptus is used to treat a variety of allergies i. Bronchitis: bronchitis is characterized by a persistent cough that causes difficulty in breathing. ii. Congestion: when the airways, lungs, sinuses, and chest are clogged, breathing becomes harder, and being ill becomes even more unpleasant. iii. Sinus: it’s possible that the lingering cold isn’t just a cold. a sinus infection might be causing congestion and headache. iv. Asthma: eucalyptus has been found to aid asthmatic breathing (Mehani and Ladjel, 2012; Gibbs, 2015).

9.10.2 Anticancer The euglobal-G1 (EG-1), a phloroglucinol-monoterpene derivative resultant from the leaves of Eucalyptus grandis, suppressed the progressional phases of two-stage model of carcinogenesis produced by structural different tumor promoters and 4-NQO and glycerol-induced pulmonary cancer. As a result, the chemical EG-1 may be useful as a chemotherapeutic agent in cancer treatment (Abdo, 2019).

9.10.3 Antidiabetic Traditional diabetic therapy includes eucalyptus globulus. It was noticed that, adding eucalyptus in the food (62.5 g/kg) and water (2.5 g/L) decreases hyperglycemia and promotes weight loss in mice treated with streptozotocin. In abdominal muscles of rat, an Aqueous Extract of Eucalyptus (AEE) (0.5 g/L) increased 2-deoxy-glucose transport by 50%, glucose oxidation by 60%, and glucose absorption into glycogen by 90%. The intake of 0.25–0.5 g AEE/L elicited a stepwise 70%–160% increases insulin production from the colonel pancreatic betacell line in acute, 20-min incubations (BRIN-BD11). These findings suggested that Eucalyptus globulus is an excellent antihyperglycemic dietary supplement for managing diabetes and a possible supply for the development of novel orally active agents for future therapy (Abdo, 2019).

9.10.4 Antibacterial The major constituents of the eucalyptus essential oil; 1,8-cineole, provides remarkable antibacterial activity against many of the harmful bacteria that include: methicillin-resistant staphylococcus aureus known as MRSA, fungi (Candida), many viruses, and mycobacterium tuberculosis. Also, the eucalyptus essential oil can act against carcinogenesis that cause tooth decay and periodontopathic bacteria (Mehani and Ladjel, 2012).

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9.11 Eucalyptus essential oils use in agro-industry 9.11.1 Eucalyptus essential oils use as insect repellent Likewise, the insecticidal ability of eucalyptus oils may open the door to new biodegradable pest management systems. Since 1948, the oil has been utilized as an insect repellent, and various commercial repellents are currently available in the United States and China. P-methane-3, 8-diol, which was extracted from E. citriodora, was also used to create a commercial mosquito repellent. Eucalyptus oil-based treatments rated 4th among insecticides used to keep insects out of beehives (Thappa et al., 1990; Ebadollahi and Setzer, 2020).

9.11.2 Development of herbicides The extensive utilization of artificial herbicides has contributed to the fast progression of herbicide-resistant weeds, as well as growing public concern over artificial herbicides’ impact on humans and environment. In this regard, research is being done on alternative strategies for controlling herbs based on natural ingredients, in which plant essential oils are gaining much attention due to the readily available natural and cheap alternatives. Depending on the natural chemistry of natural monoterpene, the essential monoterpene in the essential oils of eucalyptus has become a marketable herbicide containing the active ingredient cinmethylin. The chemical structure and bioactivity of the chemicals found in eucalyptus essential oils may also provide new possibilities for the development of herbicides with unique mechanisms of action (Thappa et al., 1990).

9.11.3 Eucalyptus essential oils application in nonfood products Studies have shown the use of commercial essential oils from Eucalyptus globulus as alternative preservatives for various tanned leather. It also boosts bacterium resistance against E. coli. The resistance of chromed leather treated with Eucalyptus globulus essential oil to E. coli bacteria was significantly reduced (five times). Eucalyptus globulus essential oil also reduces leather sensitivity to B. cereus while, Lavandula officinalis essential oil reduces leather sensitivity to P. aeruginosa (Sendanyoye, 2018).

9.12 Eucalyptus essential oils as additives in active food packaging The antibacterial action of wrapped cut sausages was investigated after adding eucalyptus oil to chitosan. Results illustrated that raising the essential oil concentration could enhance the log reduction value. Essential oils and their derivatives are also being involved in active films in a variety of ways. Eucalyptus essential oil contained chitosan films like that, have been created for the packing of square sausage with a strong possible for reducing antibacterial activity and foodborne contamination in food systems. The UV-blocking property of eucalyptus films (10 wt%) was 40% higher than the control film, while the UV-blocking property of PLA/ PBAT-cinnamon films (10 wt%) was 80% higher. Due to an elevated density of the phenolic component eugenol, which may absorb UV light, PLA/PBAT-cinnamon films had the best UV-blocking characteristic. Essential oils including eucalyptus, hinoki, nutmeg, oregano,

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and cinnamon are combined into a polyolefin-based polymer matrix to provide biodegradable packaging for fruits and vegetables. The antifungal plus antibacterial effects of these essential oils are considerably enhanced when they are encapsulated in biodegradable packaging (Sendanyoye, 2018).

9.12.1 Impact of eucalyptus oil addition on the in vitro antioxidant properties The polymers poly-lactic acid as well as poly-(butylenes adipate co terephthalate) in eucalyptus essential oil produce the following results: • Increased UV jamming property by 40%. • Decreased S. aureus and E. coli expansion by 3.04 and 3.58 log CFU/mL, respectively. • Suppresses E. coli bio-film by 84.37% (Ebadollahi and Setzer, 2020).

9.13 Eucalyptus oils use in the fragrance industry Eucalyptus oils are commonly utilized in the perfume industry (detergents, soaps, lotions, creams, deodorizers, and fragrances) as well as in the food sector as flavoring ingredients. Eucalyptus oils are also employed in the mining sector as a flotation agent and as a supply of citronellal in the chemical industry (Barbosa et al., 2016).

9.13.1 Eucalyptus oils use in air fresheners Aroma lamps, spray mists, and electric room diffusers, contain the majority of eucalyptus oils. To produce a simple mist spray, combine the ingredients in a spray bottle, 50–100 drops of essential oils in 4 fluid ounces (120 mL) clean water Spray to clean and refresh the air (Yatagai and Takahashi 1984; Barbosa et al., 2016).

9.13.2 Eucalyptus essential oils benefits for skin Since eucalyptus primary oil is sterile and antibacterial, it scrubs the epidermis of pollutants that add to skin inflammatory breakouts. Even if the proof is episodic, some believe eucalyptus oil will both ease up and fix the skin, decreasing the permeability of wrinkles and easing up spots fading. (Karpanen et al., 2010).

9.13.3 Eucalyptus essential oil used in a humidifier Cineole is the dynamic compound in eucalyptus oil and is liable for its trademark smell. When breathed in, the cineole goes about as an expectorant and calming feeling, which slackens and eliminates bodily fluid. Hence, unadulterated, undiluted eucalyptus oil can incite cerebral pains when breathed in directly, so it works best when added to the water of a humidifier since limited quantities breathed in throughout a significant period are less inclined to cause distress (Olawore and Ololade, 2017).

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9.14 Safety, toxicity and regulation Essential oils derived from sweet-smelling plants such as Eucalyptus are suitable and safe substitute because of their minimal toxicity to animals and high environment friendly nature. The most beneficial essential oils are Eucalyptus sideroxylon, Eucalyptus globulus ssp. maidenii, and Eucalyptus globulus ssp. globulus, with KT (Knockdown time) 50 values of 24.75, 31.39, and 27.73 min, respectively. A linear advanced study between the proportion of 1,8-cineole and the KT50 values of essential oils revealed a substantial association at a P < 0.01. Eucalyptus essential oils can be used in pediculicide formulations since they are efficient in opposition to head lice and are considered safer chemicals (Hu et al., 2014).

9.14.1 Safety Eucalyptus oil comes in several forms, including essential oils, medicinal and cleaning products, inhalational/volatile fluid, and topical applications. The idea that essential oils are natural does not negate the reality that incorrect handling might result in dangers or hazards. It’s more difficult to evaluate essential oil toxicity from evidence on one of the suspected hazardous chemicals since essential oils are composed up of several chemical components. When essential oil blends or mixtures are used, the condition gets considerably more intricate since blended components may interact to provide an antagonistic, additive, and synergistic. Because of the small number of reported toxicity problems, most essential oils are considered safe. Aromatherapy needs knowledge, and essential oils in the incorrect hands may be harmful. Essential oils, like aspirin, and paracetamol which are available almost everywhere, should be kept out of the reach of children. Contact the local poison control center if a kid shows to have consumed some spoonfuls of essential oil. Keep the bottle to identify the kid and to motivate him or her to drink the entire bottle of milk. Not attempt to promote emesis. If eucalyptus oils come into contact with the eyes, they should be watered as soon as possible with milk and vegetable oil. As a result, the eucalyptus oil will be diluted. Then, after rinsing with water, seek medical assistance. If you have a skin sensitivity to essential oil, dilute it with vegetable oil and then rinse the affected area with a nonscented soap. Because most of the components in essential oils are nonpolar, they don’t mix well or dissolve in water (Mengiste et al., 2020). 9.14.1.1 Safety assessment of cosmetics ingredients Cosmetic compounds made from plants such as eucalyptus can contain hundreds of ingredients, some of which are potentially toxic. For example, geraniol is said to be a possible skin sensitizer. 9.14.1.2 Safety assessment of food ingredients Eucalyptus globulus is mostly utilized as a food ingredient in the United States. Eucalyptus globulus (Eucalyptus globulus Labill) leaflets are used as a flavoring ingredient that can be added directly to meals for human consumption. In Australian aborigines, the roots are used as a water resource, cooked and eaten. The leaves of Eucalyptus globulus are used as feed for cattle, horses, and sheep in a dry form. Excess tolerance is maintained for the accumulation of

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eucalyptus globules oil in honey and honeycombs as biochemical residues in foods when 2 g or less of eucalyptus globules oil per hive is maintained. Eucalyptus oil should be used in and where possible eucalyptus oil percentage or more. The European Commission’s Scientific Committee on Food (SCF) found that the existing toxicological researches and studies of eucalyptol are limited and insufficient to derive an appropriate daily dosage. However, based on the little information available the existing animal data do not indicate a reason for concern when it comes to daily food consumption (Eisenbrand et al., 2021). 9.14.1.3 Safety assessment of drug ingredients Essential oil is used in over the counter products to in a mouthwash, cutaneous irritation, rhinosinusitis, cold sores, and Toxicodendron radicans, quercus, and somak, as well as adstringent and analgesic topical medicinal formulations. It is not an approved drug. However, there is insufficient evidence to establish universal acceptance of the safety and efficacy of these substances for specific use based on available data. Essential oil is allowed in nasal polyp’s decongestants (1.21%–1.32%) and nonsteroidal antiinflammatory drug combinations. A combination of menthol, Eucalyptus globulus oil, and camphor is worked as an active component against the allergy, cough, a cold, and bronchodilator (Smith et al., 2005). 9.14.1.4 Other Essential oil is most commonly used in the production of rum, spirit, and many other denatured alcohols.

9.14.2 Toxicity and regulation The toxicity of essential oil is determined by the number of neurotoxic components which is naturally present in the oil. As relatively small amounts of eucalyptus oil can be fatal, it should never be given orally. Children and infants are more susceptible to neurotoxic and convulsant effects. Photosensitization happens when a photo toxin in essential oil is practical directly to the dermis under the influence of UVA rays. Severe burns, pigmentation, and blistering to the entire body are all possible consequences (Kumar et al., 2015). 9.14.2.1 Oral ingestion of Eucalyptus globulus leaf oil According to the studies, adults are more likely to die at a dose of 0.05–0.5 mL/kg. When Eucalyptus globulus leaf oil is taken orally, it might cause a sweltering feeling in the oral cavity, emesis, acute diarrhea, and upper part of your abdomen discomfort. After a few minutes to 4 h the oil is directly digested and vomited. Although symptoms such as the presence of abnormal, fatigue, and tiredness may infrequently occur for 15 days after recovery from an acute illness, long-term effects have not been reported. This oil is good for people who have severe abdominal pain, it cures vomited more quickly, although practically everyone usually recovers within 24 h. Furthermore, bronchopneumonia is another component found the essential oils that can cause recovery disruption or reversed. People die within 15 min to 15 h after consumption. A small oral intake of Eucalyptus globulus leaf oil up to 5 mL that can affect the central nervous system (e.g., depression of reflexes, loss of consciousness, convulsions, and

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hypoventilation), the gastrointestinal and respiratory systems. The most common side effects are gastrointestinal, however, sleepiness and unconsciousness can happen in a matter of minutes. Many studies have indicated that urinary tract symptoms are rarely reported in adults or older children if the use of essential oils does not exceed 30 mL. Nephrotoxicity is one of common diseases occur rapid deterioration in the kidney function due to the toxic effect of essential oils. Furthermore, nephritis is uncommon but has also been reported in some cases. Aspiration is a real concern and the person can also vomit while unconscious. Tachycardia a well as a mild irregular pulse has also been recorded. Ataxia is a possibility of occurrence of muscle weakness. Mydriasis and (more often) miosis have also been appeared in some cases. On the other hand, vomiting and central nervous system depression have been postponed for up to 4 h. recovery usually takes less than 24 h (Tibballs, 1995; Flaman et al., 2001; Karunakara and Jyotirmanju, 2012; Kumar et al., 2015).

9.14.2.2 Inhalation of essential leaf oil The research on essential leaf oil inhalation toxicity in human beings is limited, and the following is a review of what is known. In the literature, the compounds are referred to as eucalyptus, eucalyptus oil, and other similar names, with almost no information about the source plant parts, manufacturing technique, or concentration/purity. Pneumonitis can be caused by inhaling eucalyptus oil as a liquid or aerosol. Vapor inhalation may be utilized medicinally, however, there is no information on the toxicity of this method. After inhalation of the oil, however, respiratory issues such as tachypnea, bronchospasm, pulmonary edema, pneumonitis and, respiratory depression might occur (Dhakad et al., 2017).

9.15 Trade, storage stability and transport of eucalyptus essential oil 9.15.1 World-wide trade and markets for eucalyptus oil As stated from the United Nations Food and Agriculture Organization, defining the global market for eucalyptus oils is challenging. The people’s republic of China dominates global eucalyptus oil production and export, accounting for around 70% of global output and export in both rich medicinal oils and fragrance oil. It is impossible to estimate the overall global demand for eucalyptus oils (Chaffey and Smith, 2008). The limited efficacy of published trade statistics for analytical purposes is due to the inadequacy of production and household utilization statistics in the making national markets, particularly for such a major producer and customer as the people’s republic of China. Moreover, some importing nations, such as Portugal, Spain, and Australia, are also manufacturers and processors of eucalyptus oils and re-export a large portion of what they import. In summary, global eucalyptus oil consumption is expected to be over 7000 tons per year and rising. Most of the world’s eucalyptus oil is used in niche markets because of its distinct odor and flavor. The majority of it is now offered for usage in pharmacies as inhalants, liniments, and expectorants, as well as flavor and fragrance use in domestic items like cleaning products (Ruiz and Lo´pez, 2010).

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New markets have emerged as a result of research and development, including medicine, pest management, fuel additives, industrial solvents, and as a raw material for a variety of industrial processes. As a byproduct of the eucalyptus wood plantation business, China produces the majority of the world’s eucalyptus oil. Each year, around 7000 tons of eucalyptus oil are sold on the global market for medicinal and household usage. The price has been very constant in recent years, ranging between 4500 and 5000 US dollars per ton (Southwell, 1992). In the 1970s, the number of Australian producers declined as a result of cheap imports from other countries, particularly China. There have been recent demonstrations in India about cheap Chinese imports undermining efforts to grow the indigenous manufacturing. Nigeria’s eucalyptus oil business has decided to request the Union Government to apply 150% antidumping taxes on Chinese oil imports in order to secure the indigenous sector. India’s domestic demand is predicted to surpass 400 tons per year (Small, 1981).

9.15.2 Storage stability of eucalyptus essential oil Eucalyptus oil products should be kept in well-filled containers at a temperature of not more than 25°C and protect to the sunlight. Liquid eucalyptus oil products should be kept in a child-resistant container. Sensitivity to volatilization, low water solubility, and instability in the presence of air ‘and light are among the drawbacks of this oil, which, in addition to limiting its therapeutic activity, disrupt the development of effective formulations (de Godoi et al., 2017). Nano encapsulation is one way to improve the stability and effectiveness of these essential oils. The application of nanotechnology in the field of medicinal plants provides benefits, for example, increased apparent solubility, biocompatibility, bioavailability, and protection against physiochemical degradation of the active ingredient, increasing pharmacological action, and toxicity prevention. Nanoemulsions are the ideal nanosystems for carrying essential oils or their constituents because of the high affinity they give in the production of droplets, allowing for easy internalization in biological coverings. Nanoemulsions are oil beads with a standard size of fewer than 100 nm that are produced by two incompatible phases that become constant by a surfactant. Depending on the required structure and usefulness, they can be obtained in a variety of ways. When compared to traditional emulsions, nanoemulsions have a clear or translucent look and are more stable (de Godoi et al., 2017).

9.15.3 Transport of eucalyptus essential oil Before placing the items into containers, they should be thoroughly examined for symptoms of leaking. Packages that are surface contaminated should not be used for shipment. When combining into containers with other cargo, pay careful attention to the other cargo’s susceptibility. Eucalyptus oil can also be transported in tank containers as well as flexible bags within 20-ft general purpose containers. Because this oil affects some materials, it’s critical to choose the right bag material (Coppen, 2002; Ribeiro-Santos et al., 2017; Sharma et al., 2021).

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9.16 Conclusion Eucalyptus species are known for their high water absorption capacity as well as their ability to withstand dry conditions. Root growth and variations in osmotic potential, gas exchange, stomatal conductance, photosynthesis, and transpiration rates are examples of morphological and physiological characteristics that reflect this feature. In addition, biochemical alterations in proline, sugar, and total protein concentrations were detected. Detailed study of eucalyptus Eco physiological responses, growth behavior, and biochemical reactions, and sub specific variation in water stress situations might aid in the selection of promising varieties and the sustainability of reforestation efforts. After selecting resistant varieties, we may plant them in dry zones on marginal soils utilizing treated wastewater irrigation, since wastewater irrigation can increase Eucalyptus plantation wood growth and production. As a result, silvicultural systems tailored to upgrade tree behavior under stress conditions should be studied. Finally, the use of Eucalyptus for reforestation in low-water areas, particularly in areas affected by climate change, would raise issues relating to water consumption, biodiversity loss, and environmental damage. Eucalyptus is a world forest heritage of considerable importance, despite its benefits and drawbacks. As previously stated, there is substantial evidence that essential oils might be produced as preventative or therapeutic medicines for a variety of oral illnesses. Although many other potential uses of Essential Oils have been reported, and several petitions of therapeutic potential have been sufficiently authenticating by whichever in vitro experiments or in vivo medical studies, more investigation is needed to establish the protection and efficacy of these Essential Oils prior to the utilization in medical practice. They may be highly beneficial in dental therapy and contribute to enhancing the quality of dental treatments if utilized appropriately. In specific, clinical trials that validate the therapeutic efficacy of Essential Oils in vivo and address concerns such as toxicity, side effects, and interactions with other pharmacological molecules, would be extremely beneficial.

References Abdo, B.M., 2019. Physico-chemical profile and antioxidant activities of Eucalyptus globulus Labill and Eucalyptus citriodora essential oils in Ethiopia. Med. Aromat. Plants 08 (02). https://doi.org/10.35248/2167-0412.19.8.332. Abed, K.M., Kurji, B.M., Abdul-Majeed, B.A., 2015. Extraction and modelling of oil from eucalyptus camadulensis by organic solvent. J. Mater. Sci. Chem. Eng. 3 (08), 35. Alencar, J.W., de Vasconcelos Silva, M.G., Machado, M.I.L., Craveiro, A.A., de Abreu Matos, F.J., de Abreu Magalha˜es, R., 1997. Use of13C-NMR as complementar identification tool in essential oil analysis. Spectroscopy 13 (4), 265–273. https://doi.org/10.1155/1997/930701. Barbosa, L., Filomeno, C., Teixeira, R., 2016. Chemical variability and biological activities of Eucalyptus spp. Essential oils. Molecules 21 (12), 1671. https://doi.org/10.3390/molecules21121671. Ben Marzoug, H.N., Bouajila, J., Ennajar, M., Lebrihi, A., Mathieu, F., Couderc, F., Abderraba, M., Romdhane, M., 2010. Eucalyptus (gracilis, oleosa, salubris, and salmonophloia) essential oils: their chemical composition and antioxidant and antimicrobial activities. J. Med. Food 13 (4), 1005–1012. https://doi.org/10.1089/jmf.2009.0153. Boukhatem, M.N., Boumaiza, A., Nada, H.G., Rajabi, M., Mousa, S.A., 2020. Eucalyptus globulus essential oil as a natural food preservative: antioxidant, antibacterial and antifungal properties in vitro and in a real food matrix (Orangina fruit juice). Appl. Sci. 10 (16), 5581. https://doi.org/10.3390/app10165581. Chaffey, D., Smith, P.R., 2008. E-Marketing: Excellence. Butterworth Heinemann, UK. Clarke, S. (Ed.), 2009. Essential Chemistry for Aromatherapy E-Book. Elsevier Health Sciences.

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C H A P T E R

10 Essential oils from Apiaceae family (parsley, lovage, and dill) Giorgiana M. Ca˘tunescua, Ioana M. Bodeab, Adriana P. Davida, Carmen R. Popc, and Ancuța M. Rotarc a

Department of Technical and Soil Sciences, Faculty of Agriculture, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Cluj-Napoca, Romania bDepartment of Paraclinical and Clinical Sciences, Faculty of Veterinary Medicine, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Cluj-Napoca, Romania cDepartment of Food Science, Faculty of Food Science and Technology, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Cluj-Napoca, Romania

10.1 Introduction Parsley (Petroselinum crispum Mill), dill (Anethum graveolens L.), and lovage (Levisticum officinale KOCH.) are herbs from the Apiaceae or Umbelliferae family which contains aromatic flowering plants. The Apiaceae family is less studied compared to the Lamiaceae family (basil, mint, oregano, rosemary, thyme) (Catunescu et al., 2016), thus it can be of great interest for current research. All three herbs are usually cultivated in the Mediterranean, with lovage predominantly being used in Eastern Europe. Current studies have shown that many factors related to the cultivated varieties of the three herbs and agronomic practices profoundly affect the yield of essential oils and their chemical composition. The production of essential oils is affected by herb variety (Petropoulos et al., 2004; Sabry et al., 2013; Salehiarjmand et al., 2014); pedo-climatic conditions of the growing area (Farouk et al., 2018); cultivation season (Tsamaidi et al., 2010; ´ lvaro et al., 2015; Tsamaidi Tsamaidi et al., 2017); fertilization (Petropoulos et al., 2009b; A et al., 2010; Salmasi et al., 2016; Rostaei et al., 2018; Khoramivafa et al., 2018); salinity ´ lvaro et al., 2015; Ghassemi-Golezani et al., 2011; Ghassemi(Petropoulos et al., 2009a; A Golezani and Nikpour-Rashidabad, 2017; Tsamaidi et al., 2017); plant density (El-Zaeddi et al., 2016; Aziz et al., 2013); irrigation treatments (Petropoulos et al., 2008; El-Zaeddi

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00015-3

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10. Essential oils from Apiaceae family (parsley, lovage, and dill)

et al., 2016); developmental stages (Petropoulos et al., 2004; El-Zaeddi et al., 2020; Lo´pez et al., 1999; Tsamaidi et al., 2010; Tibaldi et al., 2010; Salmasi et al., 2016; Novak and Nemeth, 2002); sowing date (Petropoulos et al., 2004; Aziz et al., 2013; Novak and Nemeth, 2002), among others. Additionally, the plant organ or part used for essential oil extraction influences both yield and chemical composition (Kostova et al., 2020; Kaur et al., 2021; Teneva et al., 2021; Kurowska and Gała˛zka, 2006; Semeniuc et al., 2018; Jianu et al., 2012; Li et al., 2019; Mirjalili et al., 2010; Spr
ea et al. 2020a). The type of herb processing, prior to extraction, has a substantial effect on the yield and chemical profile, as well. Essential oils are usually present in low concentration in herbs such as parsley, dill, and lovage, as low as 0.02% in hairy dill roots (Santos et al., 2002), and as high as 9.3% in parsley seeds extracted by supercritical CO2 extraction (Misic et al., 2020). Thus, suitable extraction techniques are needed to obtain high-performance separation and to generate a high enough recovery yield (Najafipour et al., 2021). Usually, Clevenger hydrodistillation and hydrodistillation are the go-to extraction methods (Rivera-P
erez et al., 2021; Farouk et al., 2018; Najafipour et al., 2021; Semeniuc et al., 2018; Rana and Amparo Blazquez, ´ lvaro et al., 2015; Santos et al., 2002; El-Zaeddi et al., 2020). 2015; Ruangamnart et al., 2015; A A solvent extraction of the essential oil contained in the distillate is generally performed after the Clevenger hydrodistillation, usually with diethyl–ether at a ratio of solvent:distilled of 1:1, followed by a drying over anhydrous Na2SO4 (Weisany et al., 2015). Solvent extractions can be used as well, employing solvents such as hexane (Bailer et al., 2001). However, their main shortcomings are that they require high volumes of solvent, need long extraction cycles, and solvents can extract non-volatile compounds as well (Farouk et al., 2018). Press and leaching can also be used (Najafipour et al., 2021). Lately, novel extraction procedures were developed and proposed such as ultrasound-assisted (Bailer et al., 2001) or supercritical fluid extraction (CO2 being the preferred solvent) (Li et al., 2019; Misic et al., 2020), solid-phase extraction (Farouk et al., 2018), to counteract the thermal degradation, oxidation, or possible solvent residues. However, they all present certain disadvantages: supercritical fluid extraction is efficient, but expensive which limits its industrial application, hydrodistillation employs heat that can affect the monoterpenes in the essential oil, solvent extractions poses the risk of volatile compounds evaporation during the procedure (Farouk et al., 2018). Parsley, dill, and lovage display various pharmacological activities (Romeilah et al., 2010; Chahal et al., 2017). Essential oils are lipophilic mixtures of volatile compounds such as terpenes, esters, ethers, aldehydes or various hydrocarbons, which confer their biological activities (Bartonkova and Dvorak, 2018). It was shown that parsley essential oil has antibacterial ( Jugreet and Mahomoodally, 2020; Marin et al., 2016), antiviral (Romeilah et al., 2010), antioxidant (Marin et al., 2016), anti-diabetic (Eissa et al., 2012), hepatoprotective (Abdellatief et al., 2017), gastroprotective (Punosˇevac et al., 2021), immunomodulating (Yousofi et al., 2012), with genitourinary effect (Abdel-Wahhab et al., 2006), and protective effect against kidney toxicity (Al-Ghamdi and AL-Amri, 2016). The active compounds contained in dill confer pharmacological properties to the extracted essential oils, among which: antibacterial (Saleh et al., 2017), antifungal (Saleh et al., 2017) anti-inflammatory (Naseri et al., 2012), hepatoprotective (Rabeh et al., 2014), gastroprotective effect (Harries et al., 1977; Dhiman et al., 2017), hypolipidemic effect (Hajhashemi and Abbasi, 2008), wound healing

10.2 Factors influencing essential oil production of parsley, dill, and lovage

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(Manzuoerh et al., 2019), spasmolytic (Dhiman et al., 2017), antifoaming and carminative effect (Harries et al., 1977), and hypolipidemic (Hajhashemi and Abbasi, 2008). Several studies reported the main pharmacological properties of lovage essential oil: antibacterial activity (Ciocarlan et al., 2018; Mirjalili et al., 2010; Miran et al., 2020; Nevas et al., 2004; Semeniuc et al., 2017), antifungal activity (Ciocarlan et al., 2018), and antioxidant activity (Mohamadi et al., 2017). Essential oils extracted from parsley, dill, and lovage have various use-cases in food industry as flavoring agents, but also as alternatives to synthetic preservatives because of their antioxidant and antibacterial properties (Teneva et al., 2021). Several studies reported the efficacy of essential oils obtained from parsley, dill, and lovage as antifungals and antibacterials, thus acting as natural preservatives and improving the shelf life of foods (Semeniuc et al., 2017; Semeniuc et al., 2018; Chahal et al., 2017; Jianu et al., 2012; Kaur et al., 2021). They are also used in cosmetics industry and aromatherapy (CBI, 2021a, 2018a) and as natural insect repellents and pest management substances (Kong et al., 2006; Kim et al., 2013a, b; Hori, 2003; Seo et al., 2015; Knio et al., 2008; Babri et al., 2012; Hieu et al., 2010). The toxicity of parsley, dill, and lovage has not been thoroughly investigated. There are only a handful of studies assessing the in vitro (Yousofi et al., 2012; Misic et al., 2020; LisBalchin and Hart, 1997; Tavakkol et al., 2019; Sharaf et al., 2009; Sertel et al., 2011; Coggins et al., 2011; Bartonkova and Dvorak, 2018) and in vivo toxicity (Lazutka et al., 2001; Sharaf et al., 2009). In Europe, parsley, dill, and lovage essential oils are considered hazardous substances (CBI, 2018b); and they fall under the Regulation EC 1272/2008 on classification, labeling, and packaging of chemicals. Additionally, the flammability, risk and safety phrase must be stated according to the Directive 2001/59/EC on the classification, packaging, and labeling of dangerous substances. The world leader in the demand of essential oils is Europe (GVR, 2020; CBI, 2018a, 2021b) and it is very likely to increase further in the following years because of the increased interest of the food and beverage industry, cosmetics and health care, and aromatherapy for essential oils (GVR, 2020). Parsley, dill, and lovage essential oil are considered niche essential oils, whose market is seeing a significant increase (CBI, 2021b). Parsley seed, dill seed and dill weed, and lovage root essential oil are the most common on the global market. The quality of parsley, dill, and lovage essential oils falls under the recommendations of ISO/TS 210:2014 (E) (ISO, 2014) in terms of packaging and ISO/TS 211:2014(E) in terms of labeling, while the specific standards are ISO 11019:1998 (ISO, 1998) for oil of roots of lovage and ISO 3527:2016 (ISO, 2016) for parsley seeds essential oil.

10.2 Factors influencing essential oil production of parsley, dill, and lovage 10.2.1 Factors influencing essential oil production of parsley The essential oil yield and phytochemical profile varies among the three species and their varieties (Table 10.1). Sabry et al. (2013) showed that the chemical composition of parsley essential oil was different for soft parsley (Petroselinum hortense), Italian cultivar clause (Petroselinum crispum), rough parsley (Petroselinum crispum), curled parsley (Petroselinum crispum ssp. crispum), and plain leaf parsley (Petroselinum crispum). Plain leaf parsley was

TABLE 10.1 Influence of origin, variety, and agronomic practices on the yield and chemical composition of essential oils extracted from parsley, dill, and lovage. Herb

Specie, variety

Origin

plant part

Factor considered

Effect

References

Parsley

Petroselinum crispum (Mill) Nym ssp. neapolitanum Danert cv. plain leaf, P. crispum ssp crispum cv. curly leaf, P. crispum ssp. tuberosum (Bernh) Crov cv. Fakir

Greece

Petioles, leaves, and roots

3 Varieties, 2 developmental stages; 2 harvest dates; plant part (petioles, leaves, and roots)

Winter-grown parsley was richer in β-phellandrene compared to spring-grown parsley (39.0% vs 22.0%), poorer in 1,3,8-p-menthatriene (17.4%– 45.7%); very low yield for root oil than herb oil; high difference in composition for the aerial organs and roots; different ratios for major compounds from petioles and leaves

Petropoulos et al. (2004)

Petroselinum crispum

Kingdom of Saudi Arabia and Egypt

Herb

2 Regions (Kingdom of Saudi Arabia and Egypt)

Variations in the essential oil yields and variations in the content of myrcene, β-phellandrene, trans-carvone oxide, α-phellandrene, 1,3,8p-menthatriene, and myristicin

Farouk et al. (2018)

Petroselinum hortense, Petroselinum crispum, Petroselinum crispum ssp. crispum

Egypt

–

5 Varieties: soft parsley (Petroselinum hortense), Italian cultivar clause (Petroselinum crispum), rough parsley (Petroselinum crispum), curled parsley (Petroselinum crispum ssp. crispum) and plain leaf parsley (Petroselinum crispum)

Plain leaf parsley was richer in bisabolene (14.19%) and carotol (5.7%); curly parsley had the highest content of myristicin (60%), followed by rough parsley (42%), plain leaf (20%), soft parsley (16%), and clause (Italian cultivar) (9%).

Sabry et al. (2013)

Petroselinum crispum (parsley varieties original from Iran, Iraq, Syria, Turkey, USA, and the former Republic of Yugoslavia)

USA

Herb

Regional differences

Variation in β-phellandrene (3.6%–33.5%); 1,3,8p-menthatriene (20.1%–68.8%); β-myrcene (15.7%–16.4%)

Simon and Quinn (1988)

Petroselinum crispum (Mill.) Fuss

Estonia

Herb

Seasonal differences (summer and winter)

A higher yield for summer parsley (0.29% vs 0.24%); variations in the content of myristicin, 1,3,8p-menthatriene, β-phellandrene, and β-myrcene

Vokk et al. (2011)

Petroselinum crispum Mill. (cultivar Gigante Italiano Darkness (plain type))

Spain

Herb

Vegetative stages (initial growth, before bud formation, and flowering)

9-Week-old parsley had the highest yield and was richest in 1,3,8-p-menthatriene and β-phellandrene

El-Zaeddi et al. (2020)

Petroselinum crispum (Mill) Nym ssp. neapolitanum Danert cv. plain leaf, P. crispum ssp crispum cv. curly leaf, P. crispum ssp tuberosum (Bernh) Crov cv. Fakir

Greece

Leaves and roots

35%–40% and 45%–60% water deficit

Water stress (up to 35% water deficit) produced higher yield in leaves essential oil extracted from plain leaf and curly leaf, but not turnip-rooted parsley; it affected the content of various compounds such as: 1,3,8p-menthatriene, myristicin, and terpinolene, p-cymenene.

Petropoulos et al. (2008)

Petroselinum crispum Mill. (cultivar Gigante Italiano Darkness (plain type)

Spain

Herb

Irrigation treatments and plant densities

Water deficit enhanced the concentration of: 1,3,8p-menthatriene (150 mg/kg), myristicin (46.8 mg/kg), and myrcene (33.7 mg/kg); the highest total content of volatiles was obtained for a moderate plant density (5.56 plants/m2)

El-Zaeddi et al. (2016)

Petroselinum crispum (Mill) Nym ssp. neapolitanum Danert cv. plain leaf, P. crispum ssp tuberosum (Bernh) Crov cv. Fakir

Greece

Leaves and roots

Salinity: adding NaCl or CaCl2 to irrigation water

Increased yield of leaves essential oil for curly leaf parsley; no effect for yield of leaves oil for turnip rooted and plain leaf parsley, nor for parsley roots oil; β-phellandrene in curly-leafed parsley increased with an increase concentration of NaCl or CaCl2; apiole increased in parsley roots oil in low salt stress

Petropoulos et al. (2009a)

Continued

TABLE 10.1 Influence of origin, variety, and agronomic practices on the yield and chemical composition of essential oils extracted from parsley, dill, and lovage—cont’d Herb

Specie, variety

Origin

plant part

Factor considered

Effect

References

Petroselinum crispum Mill.

Morocco

Herb

Salinity and nutrient solution concentrations in soilless culture

The highest essential oil yield was obtained for a salinity of 1.2–2.2 dS/m.

´ lvaro et al. A (2015)

Petroselinum crispum ssp. crispum L.

Egypt

Herb

Salt stress (1.7, 3.1, and 4.7 dS/m); 2 cuts (April and May)

The yield of essential oil varied from 0.11% to 0.21%, with the lowest for the highest salinity; β-myrcene, β-phellandrene, 1,3,8-p-menthatriene, myristicin, D-limonene, and p-cymene were affected by salinity

Aziz et al. (2013)

Petroselinum crispum (Mill) Nym ssp. neapolitanum Danert cv. plain leaf, P. crispum ssp crispum cv. curly leaf, P. crispum ssp tuberosum (Bernh) Crov cv. Fakir

Greece

Leaves and roots

4 Levels of nitrogen (3.2, 16.2, 32.4, and 48.6 g/m2)

The mean foliar oil yield doubled at 16.2 g/m2, but the root oil yield was not affected; a higher N dose caused the reduction of β-phellandrene in parsley leaves, and myristicin and apiole in roots

Petropoulos et al. (2009b)

Petroselinum crispum (Mill) Nym ssp. neapolitanum Danert cv. plain leaf, P. crispum ssp tuberosum (Bernh) Crov cv. Fakir

Greece

Leaves and roots

Freezing, drying, and storage

Freezing, drying, and storage affected the composition of essential oils, mainly by decreasing 1,3,8-p-menthatriene and increasing β-phellandrene, β-myrcene

Petropoulos et al. (2010)

Petroselinum crispum Mill.

Brazil

Leaves

Cleaning and drying

Drying at temperatures below 60°C did not change the oil yield, no effect on the content of myristicin and apiol when employing temperatures below 50°C

Corr^ea Filho et al. (2018a)

Dill

Anethum graveolens 26 commercially available accessions

Austria

Seeds

Cultivar, year of harvest, harvest period

Harvest time influenced oil composition, especially the carvone:limonene ratio; matured dill produced higher yields and better quality essential oil

Bailer et al. (2001)

Anethum graveolens L. (18 Iranian local landraces)

Iran

Seeds

18 Varieties grown in different parts of Iran

Yield variations 0.3% to 2%; variations in carvone (31.3–60.8%); dillapiole (0.2–31.9%); transdihydrocarvone (3.6–14.5%), α-phellandrene (0.2%–6.6%), dihydrocarvon (0.3%–4.3%)

Salehiarjmand et al. (2014)

Anethum graveolens (Aneto variety)

Spain

Shoots

Vegetative stages (initial growth, before bud formation, and flowering)

The total amount of compounds changed with the maturing of the herb; the content of limonene, dillether, and carvone increased, while the α-phellandrene, β-phellandrene, myristicin, and apiol contents decreased

El-Zaeddi et al. (2020)

Anethum graveolens

Italy

Leaves

Vegetative stages (preblossoming phase and end of blossoming phase)

The individual compounds were not affected by maturity, except for myristicin; a maximum yield of 0.12% occurred in the pre-blossoming phase

Tibaldi et al. (2010)

Anethum graveolens L.

Estonia

Herb, seeds

Seasonal differences (summer and winter)

Higher yield in summer than in winter (0.56% vs 0.65%); summer dill had a higher relative content of α-phellandrene

Vokk et al. (2011)

Continued

TABLE 10.1 Influence of origin, variety, and agronomic practices on the yield and chemical composition of essential oils extracted from parsley, dill, and lovage—cont’d Herb

Specie, variety

Origin

plant part

Factor considered

Effect

References

Anethum graveolens L.

Iran

Seeds

Irrigation treatments (irrigation after 70, 100, and 130 mm evaporation from class A pan) and nitrogen levels (0, 40, 80, 120 kgN/ha)

The content of cisdihydrocarvone, translimonene oxide, limonene, and dill ether increased with water limitation; N application (80 kg/ha) increased carvone and dihydrocarvone in dill seeds; the content of cisdihydrocarvone, translimonene oxide, limonene, dillapiole, dill ether, apiole and l-phellandrene was increased in plant subjected to water stress, while carvone and dihydrocarvon were affected negatively

Salmasi et al. (2016)

Anethum graveolens L.

–

Seeds

Irrigation (50, 100, 150, and 200 mm) cumulative pan evaporation), farmyard manure (0, 15, and 30 t/ha), storage conditions (0 vs 30 days) (cloth bag at room temperature, cloth bag in deep fridge, poly bag at room temperature, poly bag in deep fridge)

The highest content of carvone was reported for the medium dose (15 t/ha); increased levels of manure decreased the content of dillapiole; the content of limonene and carvone in seed oil was higher in water stress conditions; dillapiole accumulated better in medium irrigated dill

Vineeta et al. (2018)

Anethum graveolens L.

Iran

Herb, flowers, and seeds

Water stress, plant part, developmental stages

The yield of dill seeds and flower oils seemed to increase with the water deficit, but the highest yield per unit area was reported for a moderate deficit; the effect is related to the developmental stage at which water stress appears

GhassemiGolezani et al. (2008)

Anethum graveolens

–

Leaves

Fertilization (1.2 mS/cm, 2.4 mS/cm, 3.6 mS/cm containing NO3-N, P, K, Ca, Mg)

Higher yield (0.08 mg/plant) at medium nutrient solution (2.4 mS/cm vs 3.6 mS/cm)

Udagawa (1994)

Anethum graveolens L. cv. Ducat

–

Leaves

N fertilization, season of cultivation and stage of harvest

Higher yield in spring for 300 ppm N; in spring dill all oil constituents (except π-cymene) were higher at 300 ppm N, but only α-phellandrene, β-phellandrene, and dill ether in autumn/winter dill

Tsamaidi et al. (2010)

Anethum graveolens L.

Italy

Herb

Various nitrogen levels (4–16 mM), various NO3
N/NH4+-N ratios, 2 films with varying permeability, and 2 storage temperatures

No significant effect on the essential oil profile by neither N level nor NO3
-N/NH4+-N ratio

Fontana et al. (2010)

Anethum graveolens

Iran

Leaves, flowers, and seeds

Salinity stress (0–12 dS/m NaCl)

The essential oil yield increased with salinity; the highest mean essential oil percentage was obtained from seeds (0.804%), while the lowest for leaves (0.335%)

GhassemiGolezani et al. (2011)

Anethum graveolens L.

–

Leaves, flowers, and seeds

3 Saline (4, 8 and 12 dS/m NaCl) conditions in response to seed polymer coating and priming with gibberellic acid and salicylic acid

A reduction of essential oil content and yield of dill organs under severe salinity

GhassemiGolezani and NikpourRashidabad (2017)

Anethum graveolens L. cv. Ducat

Greece

Leaves, flowers, fruits and seeds

Salinity, season

Higher essential oil content in spring than in autumn (0.13–1.29 mL/100 g fresh weight vs 0.10–0.14 mL/100 g fresh weight); the season of cultivation had a higher effect on the yield and quality of dill essential oil than water stress and salinity

Tsamaidi et al. (2017)

Anethum graveolens L.

–

Herb

3 Levels of citric acid (0, 1000, and 3000 mg/L) and three levels of malic acid (0, 1000, and 3000 mg/L) as preharvest foliar sprays

Citric acid caused a decrease in dillapiole and carvacrol; citric and malic acids increased the content of α-phellandrene

Jaafari et al. (2015)

Continued

TABLE 10.1 Influence of origin, variety, and agronomic practices on the yield and chemical composition of essential oils extracted from parsley, dill, and lovage—cont’d Herb

Lovage

Specie, variety

Origin

plant part

Factor considered

Effect

References

Anethum graveolens

Iran

Herb

Organic manure and chemical fertilizer, ole and intercropped with soybean

The highest yield (1.84 g/m2) was obtained in soybean:dill (2:1) intercropping; the highest α-phellandrene (34.49%) and p-cymene (33.69%) content in the lot treated with organic manure

Rostaei et al. (2018)

Anethum graveolens inoculated with Agrobacterium rhizogenes, strain LBA 9402

Portugal

Fruits, aerial parts and roots

Inoculation with Agrobacterium rhizogenes, development stages

No significant qualitative changes during the development stages, only slight variations in the proportion of falcarinol, β-pinene, myristicin, noctanal, carvacrol

Santos et al. (2002)

Anethum graveolens L.

Iran

Leaves and shoots

Arbuscular mycorrhiza (Funneliformis mosseae) colonization and cropping system cropping at different densities (25–75 plants/m2) the additive intercropping of dill + common bean (25 + 40, 50 + 40 and 75 + 40 plants/m2)

Arbuscular mycorrhiza colonization significantly increased the yield; the inoculated and intercropped dill plants had different essential oil compositions

Weisany et al. (2015)

Anethum graveolens L. (Mesten variety)

Bulgaria

Seeds inflorescences, and shoots

Metal contaminated soils

High concentrations of Cu reduced yields; no metal transferred to the essential oil

Zheljazkov et al. (2008)

Anethum graveolens L. (‘Bouquet’ variety)

U.S.

Herb

Coal-bed methane water (CBWM) (tap water only; 25% CBMW, 75% tap water; 50% CBMW, 50% tap water; 75% CBMW, 25% tap water; and 100% CBMW)

No effect of the CBMW on the yield, an increase in dill ether content with the levels of CBMW, and a decrease in transdihydrocarvone and carvone

Poudyal et al. (2016)

Levisticum officinale KOCH

Hungary

Leaves, roots

Harvesting time (leaves at 10 day intervals from the middle of July through the beginning of November; roots beginning of September until the end of October) and plant age (1-year old and 2-year old populations)

Both the age and harvesting date influenced the essential oil content, older leaves and roots had higher essential oil content; the highest volatile oil contents in leaves were obtained in midAugust, while in the roots in the last 2 weeks of October

Novak and Nemeth (2002)

10.2 Factors influencing essential oil production of parsley, dill, and lovage

251

richer in bisabolene (14.19%) and carotol (5.7%). Curled parsley had a specific high content of myristicin (60%) and it was followed by rough parsley (42%), plain leaf (20%), and soft parsley (16%), while clause (Italian cultivar) had the lowest content (9%). Petropoulos et al. (2004) observed that the essential oil obtained from the leaves of curly leaf parsley had a higher content of β-elemene than in plain leaf and turnip rooted parsley (Table 10.1). Similarly, later on, Petropoulos et al. (2010) reported a higher total essential oil content in plain-leafed parsley compared to turnip rooted parsley, and a higher content of the major contributors to the parsley aroma (1,3,8-p-menthatriene; apiole; β-phellandrene; myristicin). This difference in the composition of essential oils was reported among various parsley varieties by other studies (Petropoulos et al., 2009b) (Table 10.1). The cultivation area of parsley greatly impacts the yield and phytochemical profile of the essential oil (Table 10.1). Farouk et al. (2018) obtained by hydrodistillation a yield of 0.28  0.08% from Egypt-grown parsley, while only 0.21  0.05% from parsley harvested in the Kingdom of Saudi Arabia. Simon and Quinn (1988) reported that the major compounds in essential oils extracted from parsley varied according to the country of origin (Iran, Iraq, Syria, Turkey, USA, and the former Republic of Yugoslavia) as follows: the content of β-phellandrene ranged from 3.6% to 33.5%; 1,3,8-p-menthatriene was found as low as 20.1% and as high as 68.8%, while β-myrcene had a lower variation from 15.7% to 16.4%. In the same note, the essential oil from Saudi Arabia was richer in β-phellandrene, myrcene, and trans-carvone oxide than Egyptian oil. Additionally, it had some unique minor compounds with concentration below 4%, in descending concentration as follows: 2-bornanol, 2-methyl-, cis-pinocarveol, p-methyl guaiacol, linalool. However, the parsley essential oil from Egypt had higher concentration of some major compounds responsible for the characteristic aroma (1,3,8-p-menthatriene, α-phellandrene, myristicin) (Farouk et al., 2018). The cultivation season was also shown to have a considerable impact on the phytochemical profile of parsley essential oil (Vokk et al., 2011; Petropoulos et al., 2004; Farouk et al., 2018). Vokk et al. (2011) reported that the essential oil yield was 0.24% of dry weight for wintergrown parsley and 0.29% for summer-grown parsley. The profile of essential oil was different as well. Petropoulos et al. (2004) observed that winter-grown parsley was richer in β-phellandrene compared to spring-grown parsley (39.0% vs 22.0%), while poorer in 1,3,8p-menthatriene (17.4%–45.7%). Similarly, summer-grown parsley was richer in myristicin and 1,3,8-p-menthatriene (42.7% and 10.0% vs 30.7% and 5.4%, respectively), while winter grown parsley had a higher content of β-phellandrene and β-myrcene (35.9% and 8.7% vs 21.8% and 4.5%, respectively) (Vokk et al., 2011). Additionally, Farouk et al. (2018) indicated that the content of 1,3,8-p-menthatriene might be a marker for the cultivation season of parsley. This could be explained by the fact that herbs growing in winter develop at relatively lower temperatures, lower light intensity, and shorter days, while spring and summer parsley benefit from higher temperatures and longer days (Petropoulos et al., 2004). Parsley is considered a herb sensitive to water stress (Najla et al., 2012); thus, there are several studies assessing how irrigation and draught affect the yield and chemical composition of essential oils. The yield of essential oil extracted from the leaves of both plain and curly leaf parsley seemed to increase by water stress (up to 35% water deficit) (Petropoulos et al., 2008). However, this was not the case for turnip-rooted parsley. This was seen despite a significant reduction in the fresh biomass. Moreover, the water deficit had a beneficial effect on curly-leafed parsley because the oil yield was reported to increases with the water stress

252

10. Essential oils from Apiaceae family (parsley, lovage, and dill)

on an area (m2) basis (Petropoulos et al., 2008). However, the impact on the essential oil yield affected the relative content of various compounds such as: 1,3,8-p-menthatriene, myristicin, and terpinolene + p-cymenene, but the effect was depended on parsley variety. In this respect, 1,3,8-p-menthatriene in plain leaf parsley was negatively affected by water stress, while the relative content myristicin was enhanced. However, in curly-leafed parsley the compound negatively impacted by water deficit was myristicin, while b-phellandrene, terpinolene, and p-cymenene met an increase in relative concentration. El-Zaeddi et al. (2016) had another approach and tested both water deficit (at 861 m3/ha) and excess (at 1788 m3/ha). They concluded that water deficit led to an increase in the concentration of the main parsley herb essential oil compounds (1,3,8-p-menthatriene, myristicin, and myrcene). Callan et al. (2007) showed that plant density affected the content of essential oil in parsley—an increased density determined a higher oil content. But the results also showed a threshold effect, that is, when reaching a density of 5.56 plants/m2 at an irrigation dose of 1290 m3/ha the positive effect on the yield of essential oils was lost (Callan et al., 2007). Petropoulos et al. (2008) reported that the yield of oil per m2 can be increased by increasing the plant density of plain leaf and curly leaf parsley. However, El-Zaeddi et al. (2016) showed that the highest yield of essential oil of 409 mg/kg can be achieved by employing a moderate plant density compared to 277 and 279 mg/kg for a lower and higher density, respectively; similarly, the highest yields of the major essential oil compounds (1,3,8-p-menthatriene, β-phellandrene, myristicin). Fertilization is another agronomic practice that impacts the yield but also the individual components of essential oils. Petropoulos et al. (2009b) tested the effect of four nitrogen (N) levels (3.2, 16.2, 32.4, and 48.6 g/m2) on the yield and chemical compounds of essential oils extracted from three parsley verities (plain and curly leaf parsley, and turnip rooted parsley). The concentration of essential oils was negatively affected by an increasing N concentration, but only in curly-leafed parsley. However, the 2.5-fold increase in foliage biomass observed for all three varieties at the 16.2 g/m2 level compared with the 3.2 g/m2 generated the doubling in mean foliar oil yield (0.68 vs 1.38 g/m2). Additionally, although the root biomass was enhanced, the increase in oil yield was not significant (0.3 vs 0.4 g/m2) at the same conditions. A higher N dose was reported to affect the profile of essential oils: β-phellandrene was reduced in parsley leaves, while myristicin and apiole decreased in the root (Petropoulos et al., 2009b). Thus, although a higher essential oil yield might be obtained at a higher N dose, the profile can be affected, and the quality might decrease. In conclusion, moderate N doses were recommended for the production of parsley for essential oil (Petropoulos et al., 2009b). Water and soil salinity stress are other agronomic factors taken into account by current research in the context of climate change. Petropoulos et al. (2009a) studied the effect of irrigation water mixed with various proportions of two salts (NaCl and CaCl2) on flat leaf, curly leaf, and turnip-rooted parsley. An increase in the yield of essential oil extracted from leaves was reported for curly leaf parsley as an effect of a higher concentration of NaCl (13.8–22.3 L/ha vs 11.7–15.6 L/h). No effect was observed for the leaf essential oil yield of turnip rooted and plain leaf parsley, nor for parsley roots oil. The profile of essential oil components was affected for curly leaf parsley, mainly attributed to the increased content of β-phellandrene observed at higher concentration of both NaCl and CaCl2. Additionally, an

10.2 Factors influencing essential oil production of parsley, dill, and lovage

253

increase in apiole content was observed in the parsley roots oil under conditions of low salt stress. Aziz et al. (2013) assessed salt stress (1.7, 3.1, and 4.7 dS/m) on curly-leafed parsley and reported that the yield of essential oil ranged between 0.11% and 0.21%, with the lowest for the highest salinity. Thus, an increased salinity seemed to lead to a decrease in the essential oil yield. Contrary to Petropoulos et al. (2009a) the lowest level of salinity was reported to favor the accumulation of the highest levels of β-myrcene and β-phellandrene. Moreover, an increased salinity up to 3.1 dS/m seemed to lead to an increase in the relative content of 1,3,8-p-menthatriene from 0.89% to 12.83.% and the highest levels generated the highest relative concentrations of myristicin (46.41%) (Aziz et al., 2013). However, β-myrcene, δ-limonene, β-phellandrene, and p-cymene were negatively affected at a salinity of 4.7 dS/m. Another study assessed the effect of solutions containing incremental macronutrient concentrations up to 3.2 dS/m, and NaCl at 3.2 dS/m on the growth of parsley cul´ lvaro et al., 2015). The highest essential oil yield was reported for a tivated soilless (A moderate salinity of 1.2–2.2 dS/m. The developmental stage to harvest parsley is crucial for essential oil production. Lo´pez et al. (1999) compared the volatile compounds from parsley at five different stages (at 5, 7, 9, 11, and 13 weeks) and concluded that the main essential oil compounds develop with the growth stages of the herb. Thus, the profile of the essential oil would vary with the growth cycle. Petropoulos et al. (2004) compared two vegetative stages at the formation of six to eight leaves and a month after the first harvest. The yield and relative content of the compounds varied significantly. They observed a decrease of β-phellandrene content in the herb from first to second stage for winter-grown parsley, and an increase for the spring-grown parsley. Myristicin increased from the first to the second stage, regardless of cultivation season. Additionally, 1,3,8-p-menthatriene seemed stable in the winter-grown parsley but decreased in the second stage for spring-grown parsley. On the contrary, apiole increased in the second stage for spring parsley. However, these variations were reported only for the herb, as the root essential oil, obtained in a very small yield, had significant qualitative differences that proved difficult to interpret. El-Zaeddi et al. (2020) recommended harvesting parsley at 9 weeks because this could ensure the highest yield of essential oil (2543 mg/kg). At this developmental stage the oil was the richest in 1,3,8-p-menthatriene and β-phellandrene, however, the highest content of myristicin and myrcene were obtained at 4 weeks after the planting date. Another factor significantly affecting the yield and quality of parsley essential oil is the plant part used for extraction. All parsley part can be used: the herb as a whole, leaves, and roots (Petropoulos et al., 2004; Petropoulos et al., 2009b, 2010). Generally, the highest difference appears when comparing the aerial organs with the roots (Petropoulos et al., 2004). Usually, the yield of parsley leaf oil ranges from 0.04% to 0.4% (Charles, 2012; Petropoulos et al., 2004; Petropoulos et al., 2009b), while being only 0.01% to 0.03% for root oil (Petropoulos et al., 2009b). Thus, only turnip rooted parsley is usually used for root oil production because of the higher root biomass. Parsley herb oil usually contains a variety of compounds, among which β-phellandrene, 1,3,8-p-menthatriene, myristicin, apiole, α-pinene, and β-pinene (Charles, 2012; Petropoulos et al., 2004; Petropoulos et al., 2008), while the roots have apiole as a major compound (Petropoulos et al., 2004). Although the oils extracted from leaves and petioles are rather similar, several differences were reported mainly in respect to the ratios among the major compounds (Petropoulos et al., 2004).

254

10. Essential oils from Apiaceae family (parsley, lovage, and dill)

Additionally, the storage and processing of parsley before essential oil extraction plays a significant role as well. Catunescu et al. (2016) reported that most of the major aroma compounds of minimally processed parsley stored at 4°C reached the maximum concentration after a storage of 5–8 days, with 1,3,8-p-menthatriene and α-phellandrene accumulating later, toward the 8th day. However, the highest quantities of β-phellandrene, β-myrcene, and o-cymene were determined at the beginning of storage, with β-myrcene decreasing by 37% toward the 12th day of cold storage (Catunescu et al., 2016). Freezing, on the other hand, reduced the content of β-phellandrene and 1,3,8-i-menthatriene in plain leaf and turnip rooted parsley (Petropoulos et al., 2010). The storage of parsley leaves in a frozen state produced an additional decrease in the content of 1,3,8-p-menthatriene, but an increase in apiole, myristicin, and terpinolene. In turnip rooted parsley, however, the content of β-myrcene and β-phellandrene increased with no perceivable decrease of 1,3,8-p-menthatriene. Drying caused a significant reduction in the content of 1,3,8-p-menthatriene and an increase in β-phellandrene in plain-leafed parsley (Petropoulos et al., 2010). It, however, increased the percentage of 1,3,8-p-menthatriene in turnip-rooted parsley. The content of 1,3,8p-menthatriene decreased gradually during storage in dried state, while β-phellandrene, β-myrcene, p-α-dimethylstyrene, and terpinolene increased. However, Corr^ea Filho et al. (2018a) concluded that convective-drying of parsley leaves at temperatures below 60°C and air velocity of 0.5 m/s did not significantly affect the yield of essential oil in relation to the fresh plant. Moreover, they reported no effect of drying on the content of myristicin and apiol when employing temperatures below 50°C, but significant losses were, in fact, reported at 60°C. Additionally, washing and sanitizing (sodium hypochlorite at 200 ppm) parsley leaves before drying at 40°C produced a significant reduction of myristicin (Corr^ea Filho et al., 2018b).

10.2.2 Factors influencing essential oil production of dill Yields of 0.2% to 1.2% are usually reported for dill weed essential oil (Tibaldi et al., 2010; Vokk et al., 2011; Tsamaidi et al., 2017), with variations dependent on dill variety, cultivation system, plant growth stage, and plant organ used, among others. Similarly, the growing area of dill will generate various yields and essential oils rich in different compounds. Thus, the yield of dill seed essential oil can vary between 0.3% to 2%, depending on the harvest region, as shown in Iran (Salehiarjmand et al., 2014), while major compound scan differ in the relative concentration as follows: carvone 31.3%–60.8%; dill apiole 0.2%–31.9%; trans-dihydrocarvone 3.6%–14.5%, α-phellandrene 0.2%–6.6%, dihydrocarvon 0.3%–4.3%. Tsamaidi et al. (2017) concluded that the season of cultivation affected more the yield and quality of dill essential oil rather than water stress and salinity. Spring-grown dill had a higher essential oil content in the leaves that autumn-grown dill (0.13–1.29 mL/100 g fresh weight vs 0.10–0.14 mL/100 g fresh weight), regardless of the other factors (Tsamaidi et al., 2017). This increase was also perceived in the increase of dill-specific aroma of spring-grown plants. Similarly, winter-grown dill herb had a smaller yield than summer-grown dill (0.56% vs 0.65%) (Vokk et al., 2011). The chemical profile of the oil depends on the season as well. Although α-phellandrene together with dill ether were reported to be the main compounds in dill leaves, regardless of season (Vokk et al., 2011; Tsamaidi et al., 2010), but with a higher relative content in summer dill (Vokk et al., 2011).

10.2 Factors influencing essential oil production of parsley, dill, and lovage

255

The yield of dill essential oil is influenced by the fertilization procedure as well. Udagawa (1994) reported a higher yield (0.08 mg/plant) at lower nutrient solution (2.4 mS/cm vs 3.6 mS/cm) containing NO3-N, P, K, Ca, Mg. Tsamaidi et al. (2010) observed that the essential oil concentration within the leaves was not affected by a N fertilization (NH4NO3) in autumn/winter, but it was higher at a moderate 300 ppm N application in spring. Various authors have reported an increase in the essential oil yield produced by using manure, vermicompost, and compost tea (Rostaei et al., 2018; Khoramivafa et al., 2018; Vineeta et al., 2018). However, the comparison bases for the studies were the non-fertilized lots, and not a proper control by using a conventional fertilization. Additionally, the essential oil profile is also affected by fertilization. In spring dill all oil compounds (except for π-cymene) were higher at 300 ppm N, but only α-phellandrene, β-phellandrene, and dill ether in autumn/winter dill (Tsamaidi et al., 2010). A higher N level increases the leaves biomass and their succulence, thus, leading to an elongation of the oil glands and a subsequent dilution of oil concentration (Salmasi et al., 2016). But, N application (80 kg/ha) was reported to increased carvone and dihydrocarvone in dill seeds (Salmasi et al., 2016). On the contrary, Fontana et al. (2010) reported no significant effect on the + essential oil profile by neither N level nor NO
3 -N/NH4 -N ratio. But there seem to be some + effects of the N level on apiol, neophytadiene, and phytol, and of the NO
3 -N/NH4 -N on α-phellandrene, β-phellandrene, and myristicin, which would need further studying. Khoramivafa et al. (2018) reported that the content of carvone could be enhanced by applying compost tea (foliar and soil applications) and cow manure. Similar results were observed for the content of limonene in dill seeds which was increased by fertilization with a high dose of farm yard manure, but the highest content of carvone was reported for the medium dose (15 t/ha) (Vineeta et al., 2018). However, an increased level of vermicompost affected negatively the content of carvone (Khoramivafa et al., 2018) and an increased levels of manure decreased dillapiole (Vineeta et al., 2018). The yield of dill seed and flower oils seemed to increase with the water deficit, but the highest yield per unit area was reported for a moderate level (Ghassemi-Golezani et al., 2008). Thus, water stress in another agronomic factor that affects the yield and composition of dill essential oil. Additionally, it seems that the effect is related to the developmental stage at which water stress appears. The lowest oil yield was reported for vegetative parts subjected to severe water deficit during early growth, while the highest yield was observed for flowers during flowering and seeding under moderate water stress conditions (Ghassemi-Golezani et al., 2008). Moreover, water stress influences the chemical composition of dill oil. The content of cis-dihydrocarvone, trans-limonene oxide, limonene, dillapiole, dill ether, apiole, and l-phellandrene was increased in plant subjected to water stress, while carvone and dihydrocarvon were negatively affected (Salmasi et al., 2016). Similarly, Vineeta et al. (2018) reported a positive effect of water stress on the content of limonene and carvone in seed oil, while dillapiole accumulated better in medium irrigated dill (up to 150 mm cumulative pan evaporation). Additionally, excessive irrigations had a negative effect on the major oil constituents. Dill is generally considered more resistant to salinity than to drought (Tsamaidi et al., 2017). However, salinity was reported to significantly affect the essential oil yield of dill, attributed mainly to the impairment of plant growth and accumulation of nutrients. The quality of dill essential oil can be affected as well, because of the impact of salt stress on the synthesis

256

10. Essential oils from Apiaceae family (parsley, lovage, and dill)

on secondary metabolites. Ghassemi-Golezani et al. (2011) reported that essential oil yield was enhanced by increasing salinity, while Ghassemi-Golezani and Nikpour-Rashidabad (2017) reported a small increase for moderate salinity conditions (8 dS/m) and a significant decrease for severe salinity (12 dS/m). It was showed that this reduction was significant in leaves, compared with other plant parts, while salinity significantly improved essential oil percentage in flowers and dill seeds (about 7.43%) (Ghassemi-Golezani and NikpourRashidabad, 2017). It was also explained that a reduction in the content of K+ inhibited the activity of several antioxidant enzymes: superoxide dismutase (SOD), acid extracellular protease (AXP), and peroxidase (POX), that might reduce the yield of essential oil in various dill parts grown in severe salinity conditions (Ghassemi-Golezani and Nikpour-Rashidabad, 2017). In terms of dill oil quality, it was reported that the content of α-phellandrene was higher in dill leaves grown in salinity levels of 4 and 6 dS/m, but the content of dill ether was lower (Tsamaidi et al., 2017). In flowers, on the other hand, both the content of α-phellandrene and dill ether decreased, while carvone increased proportionally (Tsamaidi et al., 2017). However, no effect was perceived on the quality of seed/fruit oil (Tsamaidi et al., 2017). It seems that the development stages of dill had no significant influence on the essential oil composition (Santos et al., 2002; Tibaldi et al., 2010). No relevant qualitative changes in oil composition were observed, only slight fluctuations in the relative content of some components were reported. Thus, falcarinol and β-pinene ranged from 11% to 25% and from 3% to 5%, respectively, during the first 30 days of growth, however, both decreased to 0.4% and 0.2%, respectively, at the end of the growth cycle. Myristicin showed major fluctuations during the growth cycle, ranging from 2% to 20%, the highest amount being attained 15 days after inoculation (Santos et al., 2002). Similar results were obtained by Tibaldi et al. (2010), who reported no effect of the growth stages on the main compounds of dill essential oil with the exception of myristicin that registered the peak value (0.12%) for the 1st harvest. The amount of noctanal decreased from 5% to 2% at 13 days after inoculation and attained 6% at the end of the growth cycle. Carvacrol increased to 6% at the fiftieth day of growth, reaching 2% during the first 30 days of growth (Santos et al., 2002). However, Tibaldi et al. (2010) reported a lower content of carvone which is a positive aspect, as a the presence of carvone in high quantities affects negatively the quality of dill essential oil. Additionally, they proposed an indirect relationship between β-phellandrene and carvone. On another hand, El-Zaeddi et al. (2020) concluded that the content of the individual compounds varies during the developmental stages of dill (initial growth, before bud formation, and flowering): the content of limonene, dill ether, and carvone were reported to increase with the maturing of the herb, and α- and β-phellandrene, myristicin, and apiol were found in lower quantities. Similarly, Khoramivafa et al. (2018) stated that α-phellandrene in dill essential oil increased during vegetative growth but decreased in productive phase. Tibaldi et al. (2010) reported that the content of myristicin in dill weed oil varied between the pre-blossoming and end-blossoming stages, maybe because its conversion to dill ether, α-phellandrene or β-phellandrene in the mature dill. Dill is mainly used as a condiment, thus the main interest is on the green mass production (weed and leaves) and not on the seeds yields (Bailer et al., 2001). In this context, the currently cultivated varieties are not always suitable for harvesting seeds. Vineeta et al. (2018) observed that dill apiole was converted to oxygenated terpenes during seed-growing stages. Bailer et al. (2001) reported that harvest time influenced the composition of the essential oil: the

10.2 Factors influencing essential oil production of parsley, dill, and lovage

257

carvone:limonene ratio varied between the two studied years. More immature dill seeds were harvested during the first year, while more mature seeds were lost during harvesting by shattering. The quality of the obtained essential oil differed as well between the 2 years, with the major differences found for limonene. Therefore, dill seeds for essential oil production should be harvested only at maturation. Additionally, it was shown that seed yield and quality are significantly affected by windy weather during the maturation of seeds because they can be rapidly dispersed by wind and shattered during harvesting (Bailer et al., 2001). In a similar note, Ghassemi-Golezani et al. (2008) evaluated the effect of harvest at vegetative, full flowering, and seed maturity stages. They concluded that both water availability and developmental stage at harvest time significantly affects the yield and quality of the extracted essential oil content. Zheljazkov et al. (2008) conducted field experiments in soils contaminated with metals and assessed the effect of heavy metals (ZndCu smelter area) on dill essential oil yield. Results showed that high concentrations of heavy metals in soil or growth medium reduced essential oil yields, but no metal transfer was observed in the essential oil. Moreover, of the tested metals, only high concentrations of Cu caused a reduction in the oil content (Zheljazkov et al., 2008). Soilless culture system and young stage harvesting (38-day crop cycle) were shown to limit the synthesis of characteristic dill essential oil components: α- and β-phellandrene carvone, or limonene, and enhance the production of apiol, neophytadiene, and phytol (Fontana et al., 2010). Weisany et al. (2015) reported that the yield of dill essential oil was significantly influenced by arbuscular mycorrhiza (Funneliformis mosseae) colonization and cropping system. The additive intercropping of dill with the common bean (Phaseolusvulgaris L.) significantly enhanced the essential oil yield, and content of α- and β-phellandrene, carvone, and limonene. The mechanism behind these changes could be attributed to better nutrition. Similarly, the intercropping with soybean and fertilizing with organic manure enhanced not only the yield and quality of dill essential oil, but also its antioxidant activity (Rostaei et al., 2018). The best reported intercropping ratio was 2:1 soybean:dill which yielded the highest level of essential oil (1.84 g/m2), and the highest content in the main oil compounds (34.49% α-phellandrene and 33.69% p-cymene) was obtained for the fertilization with organic manure. The highest proportion of carvone (49.66%) was obtained when dill was cultivated alone and fertilized with organic manure. However, no positive controls (experimental lots treated with conventional fertilizer) were used in these experiments, thus, the conclusion that organic manure might enhance essential oil production and bioactivity needs to be thoroughly tested in an experiment employing all needed controls. The influence of citric acid and malic acid treatments as preharvest foliar sprays on dill essential oil were analyzed by Jaafari et al. (2015). The results showed that some major components such as dillapiole and carvacrol were reduced by the citric acid treatments. However, the content of α-phellandrene was increased by a treatment containing both citric and malic acids. Additionally, citric acid and malic acid seemed to have an antagonistic effect upon the content of dillapiole: dillapiole was not found for a treatment of 3000 mg citric acid per L, while a similar content of malic acid cause a slight increase. Thus, these organic acids could be considered as regulators of dill essential oil production ( Jaafari et al., 2015). Similarly, the treatment of dill seeds with gibberellic acid and salicylic acid increased the yield in essential

258

10. Essential oils from Apiaceae family (parsley, lovage, and dill)

oil for all dill organs up to 26.60% and 37.59%, respectively. These results could be attributed to the stimulation of plant growth, increase uptake of nutrients, modifications in the distribution of the oil glands, and enhancement of the biosynthesis of monoterpenes (GhassemiGolezani and Nikpour-Rashidabad, 2017). Poudyal et al. (2016) tested the Coal-Bed Methane Water Sustainable (CBMW) disposal influence on the yield of dill essential oil. The results showed that the oil content ranged from 0.16% to 0.2% with an increase in dill ether content, but a decrease in trans-dihydrocarvone and carvone content, as the level of CBMW increased. In contrast, dill essential oil yield did not seem affected by the various tested CBMW treatments. The yield of essential oil from dill is also significantly influenced by the plant organs used for extraction (Tables 10.1 and 10.3). The essential oil yield of dill seeds, sometimes called fruit, ranges between 0.80% and 4% (Santos et al., 2002; Tibaldi et al., 2010; GhassemiGolezani et al., 2011; Ghassemi-Golezani et al., 2008) and it is usually much higher than in other organs (Ghassemi-Golezani and Nikpour-Rashidabad, 2017; Ghassemi-Golezani et al., 2011). It has a density of 0.895–0.925 kg/dm3 (Tibaldi et al., 2010) and its main constituents are monoterpenes up to 99% (Santos et al., 2002) with carvone and limonene as major components (Tibaldi et al., 2010; Santos et al., 2002; Sintim et al., 2015; Radulescu et al., 2010; Singh et al., 2017). However, the actual proportion of these compounds varies in different studies: limonene (39.37–42.67 mg/100 g FW) and carvone (40.34–54.98 mg/100 FW) (Tsamaidi et al., 2017), limonene (21.56%) and carvone (75.21%) (Radulescu et al., 2010), limonene (12.4%) and carvone (47.7%) (Singh et al., 2017). The aerial parts or the weed have a lower essential oil yield of about 0.3% (Santos et al., 2002) and a density of 0.884–0.900 kg/dm3 (Tibaldi et al., 2010). The content of monoterpenes was reported lower, of only 79% (Santos et al., 2002), and α-phellandrene as the major constituent (Santos et al., 2002; Sintim et al., 2015; Tsamaidi et al., 2017; Radulescu et al., 2010; Vokk et al., 2011). On the contrary, α-phellandrene is only a minor component in seeds oil (0.12%) (Radulescu et al., 2010). Other compounds were reported in dill weed oil such as phenylpropanoids (17%), dill apiole (10%), and myristicin (7%) (Santos et al., 2002), or β-phellandrene (12.08–12.88 mg/100 g FW) and dill ether (8.80–12.17 mg/100 g FW) (Tsamaidi et al., 2017), limonene (13.28%) and dill ether (anethofuran) (16.42%) (Radulescu et al., 2010), myristicin (1.7%–28.2%), dill ether (0.9%–14.8%), β-phellandrene (7.4%–7.5%), and limonene (3.7%–3.8%) (Vokk et al., 2011). However, other authors reported dillapiole as the major constituent of dill weed oil (Singh et al., 2017). In this respect, Bailer et al. (2001) states that some compound such as dill apiole and myristicin could be typical for certain varieties, indicating different dill chemotypes. When the weed is split in leaves and flowers, the leaves have the lowest essential oil yield (0.12%–0.335%) (Ghassemi-Golezani et al., 2011; Ghassemi-Golezani and NikpourRashidabad, 2017; Radulescu et al., 2010). While the chemical composition of leaves is very similar to that of dill weeds, the major components of dill flower oil were reported to be α-phellandrene (15.85–35.26 mg/100 g FW), limonene (32.00–37.55 mg/100 g FW), and carvone (22.89–40.58 mg/100 g FW) (Tsamaidi et al., 2017), and α-phellandrene (30.26%), limonene (33.22%), and dillapiole (22%) (Radulescu et al., 2010). Additionally, Tsamaidi et al. (2017) showed that when harvesting dill weed after flowering it includes flowers or even seeds, thus the quantity of essential oil will be higher and composition richer in compounds specific for flowers and seeds. The yield in essential oils (w/w%) was dependent on the

10.2 Factors influencing essential oil production of parsley, dill, and lovage

259

anatomical parts and the plant developmental stages, as follows: immature fruits (1.5%), followed by green mature fruits (1.0%), then ripened fruits (0.6%), and lastly flowers (0.1%) (Mirjalili et al., 2010). The yield of essential oil extracted from roots was reported 0.06%, and 0.02% for hairy root cultures (Santos et al., 2002). The major constituents in root oil were monoterpenes (65%) and phenylpropanoids (62%) in hairy roots. The quantity and quality of dill oil is also influenced by storage. Fontana et al. (2010) reported that the permeability of the packaging film, the storage temperature and duration significantly affect the chemical composition of dill oil. Catunescu et al. (2016) reported that until the 8th day of storage at 4°C of minimally processed dill the content of α- and βphellandrene increased, while δ-limonene and β-myrcene were reduced by 92% and 73%, respectively. Similarly, Vineeta et al. (2018) reported a decrease in limonene and dillapiole and an increase in carvone during storage.

10.2.3 Factors influencing essential oil production of lovage Lovage is an understudied herb, with only a handful of studies reporting the effects of various factors on essential oil production. Only one study was found reporting the effect of harvest time, herb part, and herb age on the essential oil yield (Novak and Nemeth, 2002). Both age and harvest were reported to significantly affect the yield of essential oil, mainly that the 2-year herbs and roots had a significant higher content (2.78% DW vs 1.84% DW); leaves had their peak essential oil content in mid-August, while roots in the last 2 weeks of October. However, the essential oil major compounds did not seem to be influenced by these factors. Mirjalili et al. (2010) reported that the content of β-phellandrene varied with the development stage of the herb and the plant organ used for extraction. The highest relative content (62.4%) of β-phellandrene was found in green mature fruits, then in ripe fruits (60.5%), followed by immature fruits (56.4%), and lastly, the lowest amount was obtained from flowers (11.7%). Additionally, the essential oil obtained from lovage flowers contained sesquiterpenes, mainly spathulenol (8.9%) whose relative content decreased as the fruits developed and matured (Mirjalili et al., 2010). Miran et al. (2018b) identified pentylcyclohexa-1,3-diene (28.1%), (Z)- ligustilide (24.5%), neocnidilide (15.9%), methyl eugenol (8.5%), and E-3-butylidene-phthalide (4.6%) as the major constituents of the aerial part essential oil, at flowering stage. However, the lovage essential oil chemical profile changes during fruiting stage, having the following components: (Z)-ligustilide (26.0%), pentyl-cyclohexa1,3-diene (22.7%), neocnidilide (23.0%), methyl eugenol (6.5%) and E-3-butylidene-phthalide (1.0%) (Miran et al., 2018b). Similarly, the developmental stages of lovage can influence the relative content of the major constituents of roots essential oil. Therefore, the major compounds in the roots oil at the time of flowering were: α-terpineol acetate (42.1%), β-phellandrene (13.3%), Z-β-ocimene (13.0%) neocnidilide (11.6%), and (Z)-ligustilide (5.8%). But the percentages of (Z)-β-ocimene and β-phellandrene were higher at the fruiting time 28.1% and 17.3%, respectively; while the α-terpineol acetate neocnidilide, and (Z)ligustilide were lower, reaching 21.1%, 4.8%, and 0.8%, respectively (Miran et al., 2018b). Perineau et al. (1992) concluded that the water content in the sample influences both the yield and the quality of essential oil. Thus, the yield, in terms of FW, was much higher for the

260

10. Essential oils from Apiaceae family (parsley, lovage, and dill)

dried roots (12% water content) than for the fresh (68% water content) (0.41%–0.47% vs 0.16%–0.24%). However, the drying did interfere with the essential oil content in the roots, as when expresses per DW, the fresh roots yielded a higher essential oil content (0.50%– 0.74% vs 0.47%–0.54%). In terms of quality, the essential oil obtained from dry roots had a higher content of phthalides and sesquiterpenes, because the more volatile constituents were lost during storage and processing. When using fresh roots, a higher yield of monoterpenes was obtained. Catunescu et al. (2016) showed that storing minimal processed lovage at 4°C for 5 days generated a 21% increase in the content of β-phellandrene and a 96% decrease in α-terpinolene. Additionally, δ-limonene and α-phellandrene were shown to decrease significantly after 12 days while β-myrcene doubled in content.

10.3 Extraction techniques of parsley, dill, and lovage essential oil 10.3.1 Extraction techniques for parsley essential oil Several studies employed Clevenger hydrodistillation (Table 10.2) on fresh leaves and herb (Corr^ea Filho et al., 2018b; Aziz et al., 2013), dry leaves and herb (Vokk et al., 2011; Corr^ea ´ lvaro et al., 2015; Farouk et al., 2018), and frozen leaves or roots Filho et al., 2018b; A (Petropoulos et al., 2009a). The usual boiling time varied from 2 to 4 h depending on the amount of sample, sometimes the removal of essential oil was done periodically (i.e. every 30 min) (Corr^ea Filho et al., 2018b). However, the time for hydrodistillation in a Clevenger apparatus is quite long, and this led to the developing of micro-steam distillation which is performed in a Likens–Nickerson apparatus (Petropoulos et al., 2008; Petropoulos et al., 2009b). Petropoulos et al. (2004) used this apparatus for the simultaneous distillation–extraction (SDE) of essential oil from various parsley parts (leaves, petioles, and roots) of three types of parsley harvested on three dates. Pentane was used as extraction solvent at a ratio solvent:herb of 3:5 (v/w) to extract the samples for 1 h. No reports of total essential oil yield are available, only the proportion of the various components. El-Zaeddi et al. (2016) used a Polish version of the Clevenger—called the Deryng system— to extract essential oil from fresh parsley herb. A water:sample ratio of 10:1 (v/w) was used together with NaCl in a proportion of 1:15 (w/w) and as internal standard, a volume of 50 μL of benzyl acetate (1470 mg/L) was added. At the beginning of the hydrodistillation 1 mL of cyclohexane was added and the mixture was kept boiling for 1 h. The essential oil obtained had a very similar profile with those obtained by other procedures such as Clevenger distillation (Vokk et al., 2011) or SDE (Petropoulos et al., 2004). A total of 18 compounds, with β-phellandrene, 1,3,8-p-menthatriene, myristicin, myrcene, terpinolene, limonene, α-pinene, and α-phellandrene as main constituents were extracted. A similar technique was employed by El-Zaeddi et al. (2020). Supercritical fluid extraction is a widely used procedure nowadays because of the mild processing parameters (Misic et al., 2020). The low employed temperatures enable the recovery of thermolabile compounds and the advanced separation from CO2 by pressure reduction. Misic et al. (2020) proposed a supercritical fluid extraction procedure to extract a

TABLE 10.2 Extraction method Hydrodistillation

Influence of extractions conditions on the yield and chemical composition of essential oils extracted from parsley, dill, and lovage. Herb

Part

Conditions

Essential oil yield

References

Parsley

Herb

Dried herb, Clevenger apparatus

0.24%–0.29% D.W.

Vokk et al. (2011)

Deryng system, 10:1 (v/w) water:sample ratio; NaCl in a proportion of 1:15 (—); 50 μL of benzyl acetate (1470 mg/L) as internal standard; 1 mL of cyclohexane at the beginning of hydrodistillation; 1 h

Up to 2543 mg/kg

El-Zaeddi et al. (2020)

Deryng system; 10:1 (v/w) water:sample; 1:15 (—) NaCl; internal standard—50 μL benzyl acetate

NA

El-Zaeddi et al. (2016)

Clevenger apparatus, 4 h

Up to 450 μL/100 D.W.

´ lvaro et al. A (2015)

Clevenger apparatus, distilled water:sample ratio of 15:1 (v/w), 3 h

0.16% (v/w)

Semeniuc et al. (2018)

Dried leaves, Clevenge apparatus, 3 h

NA

Farouk et al. (2018)

Frozen leaves, Clevenger apparatus

0.68–1.38 g/m2

Petropoulos et al. (2009a)

Roots

Clevenger apparatus

0.3–0.4 g/m2

Petropoulos et al. (2009a)

Weed

Dried herb, Clevenger apparatus

0.56%–0.65% D.W.

Vokk et al. (2011)

Deryng system, 10:1 (v/w) water:sample ratio; NaCl in a proportion of 1:15 (—); 50 μL of benzyl acetate (1470 mg/L) as internal standard; 1 mL of cyclohexane at the beginning of hydrodistillation; 1 h

Up to 2619 mg/kg

El-Zaeddi et al. (2020)

Clevenger apparatus, 3 h

0.3% F.W.

Rana and Amparo Blazquez (2015)

Clevenger apparatus, 3 h

0.3%

Santos et al. (2002)

Leaves

Dill

Continued

TABLE 10.2 Influence of extractions conditions on the yield and chemical composition of essential oils extracted from parsley, dill, and lovage—cont’d Extraction method

Herb

Lovage

Part

Conditions

Essential oil yield

References

Leaves

Clevenger apparatus

0.9%

Singh et al. (2017)

Seeds

Schilcher apparatus; 20% NaCl aqueous solution as solvent, a solvent:sample ratio of 35:1; 12 h; cooling water at 19°C, and no organic solvent in the receiver vessel

4% yield

Bailer et al. (2001)

5:1 Water: dill seeds ratio

1.310 g/100 g seeds

Sintim et al. (2015)

Clevenger apparatus

2.4%

Singh et al. (2017)

Clevenger apparatus, 3 h

2%

Santos et al. (2002)

Industrial hydrodistillation unit equipped with a pulsed sieve plate column, 16.67:1 water:seed ratio, 6 h

Up to 38.65%

Najafipour et al. (2021)

Clevenger apparatus, 10:1 water:seeds ratio, 5 h

2.01  0.25%

Ruangamnart et al. (2015)

Hairy roots

Clevenger apparatus, 3 h

0.02%

Santos et al. (2002)

Herb

Clevenger apparatus, 150 g of crushed plant, 3 h

2.5% (v/w)

Miran et al. (2018a)

Clevenger apparatus, 150 g of crushed plant, 3 h

2.5%–3.0% (v/w)

Miran et al. (2018b)

Clevenger apparatus, distilled water:sample ratio of 15:1 (v/w), 3 h

0.28% (v/w)

Semeniuc et al. (2018)

Clevenger apparatus

1.84% 2.7% D.W. for fresh leaves 1.72%–2.22% D.W. for dry leaves

Novak and Nemeth (2002)

Clevenger apparatus

NA

Cu et al. (1990)

–

0.15%

Perineau et al. (1992)

Leaves

Roots

Simultaneous distillation– Extraction (SDE)

Parsley

Dill

Clevenger apparatus

NA

Novak and Nemeth (2002)

Clevenger apparatus, 150 g of crushed plant, 3 h

2.5%–3.0% (v/w)

Miran et al. (2018b)

Petioles

Lickens–Nickerson apparatus; pentane:herb ratio of 3:5 (v/w); extracted for 1 h

NA

Petropoulos et al. (2004)

Leaves

Lickens–Nickerson apparatus; pentane:herb ratio of 3:5 (v/w); extracted for 1 h

NA

Petropoulos et al. (2004)

Roots

Lickens–Nickerson apparatus; pentane:herb ratio of 3:5 (v/w); extracted for 1 h

NA

Petropoulos et al. (2004)

Weed

Nickerson apparatus, n-pentane as solvent, 3 h

NA

Santos et al. (2002)

Seeds

Nickerson apparatus, n-pentane as solvent, 3 h

NA

Santos et al. (2002)

Hairy roots

Nickerson apparatus, n-pentane as solvent, 3 h

NA

Santos et al. (2002)

Steam distillation

Dill

Seeds

Modified Clevenger apparatus with an upper chamber, 50 g seeds, 5 h

1.05  0.07%

Ruangamnart et al. (2015)

Micro-steam distillation

Parsley

Leaves Leaves

Likens–Nickerson apparatus; water: diethyl ether:herb ratio of 10:0.5:(1–1.2) (v/v/w)

0.03%–0.11% F.W.

Petropoulos et al. (2009b)

Likens–Nickerson apparatus; water: diethyl ether:herb ratio of 10:0.5:(1–1.2) (v/v/w)

0.04%–0.11% F.W.

Petropoulos et al. (2008)

Roots

Likens–Nickerson apparatus; water: diethyl ether:herb ratio of 10:0.5:(1–1.2) (v/v/w)

0.01–0.05 mL/100 g F.W.

Petropoulos et al. (2008)

Roots

Likens–Nickerson apparatus; water: diethyl ether:herb ratio of 10:0.5:(1–1.2) (v/v/w)

0.01%–0.03% F.W.

Petropoulos et al. (2009b)

Parsley

Seeds

CO2; 40°C; 10 and 30 MPa;

4.20% (10 MPa); 9.3% (30 MPa)

Misic et al. (2020)

Dill

Seeds

60 Mesh particle size, 25 L/h CO2, for 120 min at 40°C, and 20 MPa pressure

6.7%

Li et al. (2019)

Supercritical fluid extraction

Continued

TABLE 10.2 Influence of extractions conditions on the yield and chemical composition of essential oils extracted from parsley, dill, and lovage—cont’d Extraction method Headspace solid-phase microextraction

Solvent extraction

Herb

Part

Conditions

Essential oil yield

Parsley

Leaves

the leaves cut in pieces of 1–2 cm, 2 g of sample placed in a 20 mL SPME vial and sealed; SPME device coated (fused-silica fiber) with a 100-μm layer of polydimethylsiloxane; 60°C for 30 min.

NA

References Farouk et al. (2018)

Lovage

Roots

N passed over 900 g of lovage root for 24 h; elution of headspace with diethyl ether, then adsorbed on XAD-4 and evaporated for 48 h at room temperature

NA

Cu et al. (1990)

Dill

Seeds

Hexane:sample ratio of 3:1, sonication for 10 min, centrifugation and separation of the solvent, then reextracted twice with fresh solvent

4% yield

Bailer et al. (2001)

Lovage

Roots

Soxhlet apparatus, various solvents, number of: extraction repetitions and of siphonages, sample: solvent ratios, lovage roots grinding degree

66.25% ethanol, 62.4% CFC-113, 54.19% sylvan, 66.82% benzene, 63.04% dichloromethane, 44.39% cyclohexane, hexane 50.04%

Cu et al. (1990)

Where: F.W.—fresh weight; D.W.—dry weight; NA—not available.

10.3 Extraction techniques of parsley, dill, and lovage essential oil

265

volume of 150 mL of ground parsley seeds (0.4 mm in average diameter) with CO2 at a flow rate of 0.3 kg/h. The extraction was performed under mild conditions (40°C; 10 and 30 MPa). A yield of 9.3% was reported for 30 MPa, thus much higher than the usual yield obtained by hydrodistillation (up to 4%). At this pressure the fatty oils contained in the seed can be extracted as well, explaining the high yield. However, a content of apiol above 85% was reported and no significant differences in essential oil profile between the 10 and 30 MPa samples. Farouk et al. (2018) proposed headspace solid-phase microextraction (SMPE) to extract essential oil from dried parsley leaves as a better substitute to hydrodistillation by Clevenge apparatus for 3 h. Prior to extraction the leaves were cut in pieces of 1–2 cm, then 2 g of sample were placed in a 20 mL SPME vial, and the vial was sealed. A SPME device coated (fusedsilica fiber) with a 100-μm layer of polydimethylsiloxane was used to expose the vial at 60° C for 30 min. The sample was then analyzed by gas chromatography. The difference between the 2 methods was radical in terms of number of identified volatile compounds (39 for hydrodistilation vs 16 for SMPE), but monoterpenes were the major compounds in both. The most significant differences were reported for myristicin (26.21% for hydrodistilation vs 4.87% for SMPE), other compound such as bornyl acetate and α-ionone found in SMPE, were only found below in traces in the hydrodistilled extract. These differences can be attributed to the effect of heat and pH on the aroma compounds during hydro distillation. However, although SMPE is simpler, more rapid and economic, it can only be employed at a laboratory scale to study the aromatic volatile compounds in herbs, and not to obtain essential oil at a commercial scale. The revers is also true, as hydrodistilation should not be employed as a preliminary step for the study of aromatic volatile compounds.

10.3.2 Extraction techniques for dill essential oil Similar to parsley, Clevenger hydrodistillation is widely used to extract essential oil from dill hairy roots (Santos et al., 2002), fruits or seeds (Santos et al., 2002; Singh et al., 2017; Najafipour et al., 2021), weed (Santos et al., 2002; Weisany et al., 2015; Singh et al., 2017) as seen in Table 10.2. The usual boiling time was 2–3 h for areal parts and roots (Santos et al., 2002; Weisany et al., 2015). However, Najafipour et al. (2021) needed 6 h to obtain dill seeds essential oil using an industrial hydrodistillation unit in which they extracted 9 kg of dill seeds using 150 L of distilled water. A Nickerson apparatus can also be used, with n-pentane as solvent, and an extraction time of 3 h (Santos et al., 2002). Weisany et al. (2015) suggested the concentration of the organic layer of the obtained distillate at 35°C, by using a Vigreux column. Sintim et al. (2015) showed the dynamics of compounds extraction during the a 195-min hydrodistillation of dill seeds. A ratio of water:dill seeds of 5:1 was used, and samples were collected at 10 time intervals. It was reported that the highest yield was obtained in the first 2 min of the extraction, then it decreased progressively and only 7% was extracted in the last hour. Almost all the content of δ-limonene and p-cymenene were extracted up to the 7th minute of hydrodistillation, most trans-dihydrocarvone in the interval 7–45 min, carvone and most of the apiole during 45–75 min, and lastly the cis-dihydrocarvone at the end of the process (45–165 min). Thus, regression models were proposed for the prediction of dill seeds essential oil composition.

266

10. Essential oils from Apiaceae family (parsley, lovage, and dill)

Bailer et al. (2001) presented the use of a Schilcher apparatus—a Clevenger-apparatus equipped with a second cooler—to extract essential oil from crushed dill seeds. In this way, the essential oil can be completely extracted from the sample because the tissues dissolve during the long extraction periods (12 h). However, the disadvantage is that some of the more volatile compounds, such as limonene, can be lost. The proposed procedure was as follows: the solvent used was a 20% NaCl aqueous solution, a solvent:sample ratio of 35:1, 12 h of hydrodistillation, cooling water at 19°C, and no organic solvent was used in the receiver vessel. However, despite its wide use, some authors showed hydrodistillation had limitation compared to other methods, such as solvent extraction paired with sonication, especially in terms of a very prolonged duration (12 h vs under 1 h) (Bailer et al., 2001). El-Zaeddi et al. (2020) used the Deryng system to extract essential oil from fresh dill following the procedure previously proposed for parsley (El-Zaeddi et al., 2016): a water:sample ratio of 10:1 (v/w), then adding NaCl in a proportion of 1:15 (—), 50 μL of benzyl acetate (1470 mg/L) as internal standard, then adding 1 mL of cyclohexane at the beginning of hydrodistillation and boiling for 1 h. But, a high amount of essential oil is still present in the waste waters produced in the hydrodistillation process. Najafipour et al. (2021) showed that using a pulsed sieve plate column can increase the essential oil recovery from dill seeds up to 38.65%. For their experiment they employed a liquid–liquid extraction of the essential oil in n-hexane using a glass column with a 0.090 m diameter cylindrical shell and a length of 1.270 m containing stainless steel plates with 3 mm holes. The n-hexane had varying flow rates 10–35 mL/min, while the waste waters containing the essential oil had a constant flow rate of 1.1 mL/min. The optimal proposed extraction conditions were as follows: 1.6 cm/s pulse intensity, 35 mL/min n-hexane flow rate, and a 1.1 mm nozzle size. The obtained essential oil had dihydrocarvone as the main constituent (35.93%). Thus, the essential oil yield obtained by hydrodistillation can be enhanced further by developing methods of extraction from the resulted waste waters. Bailer et al. (2001) proposed a hexane solvent triple extraction and an ultrasonic treatment to obtain essential oil from crushed dill seeds. The following procedure was used: a solvent: sample ratio of 3:1, sonication for 10 min while cooling under cold tap water, centrifugation, separation of the solvent, then a double reextraction adding fresh solvent each time. The yields obtained were very similar to a Schilcher hydrodistillation, around 4%. Higher yields of carvone (up to 5%) were obtained by hydrodistillation, but lower yields of limonene (up to 2%). This can be explained by the fact that carvone is less soluble in hexane, and that limonene, a highly volatile compound, can be lost during prolonged extraction times. However, the percentages were considered small, and the quality of the oil was reported as being similar. Li et al. (2019) tried to optimize the supercritical fluid extraction of dill seeds essential oil and to achieve a yield of 6.7% proposed the following optimal extraction parameters: 60 mesh particle size, a CO2 flow of 25 L/h, extraction temperature of 40°C, extraction period of 120 min, and pressure of 20 MPa. The main extracted compounds were d-carvone (40.36%), D-limonene (19.31%), apiol (17.50%), 9-octadecenoic acid (9.00%) and α-pinene (6.43%).

10.3.3 Extraction techniques for lovage essential oil As in the case of parsley and dill, hydrodistillation is the main extraction method for lovage essential oil, regardless of the plant organ used: roots (Cu et al., 1990; Perineau et al., 1992; Novak

10.3 Extraction techniques of parsley, dill, and lovage essential oil

267

and Nemeth, 2002; Miran et al., 2018b), aerial parts (Novak and Nemeth, 2002; Miran et al. 2018a; Ciocarlan et al., 2018; Miran et al., 2018b), or leaves (Semeniuc et al., 2017; Semeniuc et al., 2018). The employed technique is usually Clevenger hydrodistillation (Table 10.2). However, earlier studies showed that a solvent extraction could also be employed to extract essential oils from lovage roots (Cu et al., 1990). This endeavor tried to avoid the second step of hydrodistillation that completes the separation of the essential oil from aromatic waters by extraction with ethyl ether. They used a Soxhlet apparatus and an array of solvents, including 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113), dichloromethane, benzene, hexane, cyclohexane, and methyl furan (sylvan). The following parameters were optimized: number of extraction repetitions and of siphonages, sample:solvent ratio, the grinding degree of the lovage roots. The obtained yields varied from 44.39% (cyclohexane) to 66.25% (ethanol) and showed that the yield varied mainly related with to the polarity, more polar solvents generated higher yields. Additionally, the ratio between the volatile and non-volatile compounds varied, from 4.6%:95.4% for ethanol and 56.6%:43.4% for CFC-113, showing that a higher yield does not necessarily mean a better aroma profile. Perineau et al. (1992) studied the hydrodistillation of lovage roots for essential oil production because the phthalides (present in a proportion of 60%–85%) pose difficulties upon extraction. Thus, lovage essential oil is usually difficult to coalesce. For this purpose, a hydrodistillation pilot unit equipped with a cohobation system was used to assess the effect of water:sample ratio, loading ratio, and the water-essential oil mixture separation step in terms of pH and temperature. They reported that the water content of the roots plays an important role in the extraction procedure. For dried lovage roots the hydrodiffusion phase is slower (8 vs 6 h for fresh roots). The following optimal processes parameter when extracting essential oil from lovage roots extraction were proposed: a sample:water ratio of 1:4 for dry roots and 1:1 for fresh roots; a 100% loading of the extraction tank volume for dry roots and only 50% for fresh roots, because they cause foaming and the tank cannot be filled. Thus, when considering a drying pre-processing step, it must be considered that although the loading of the tank can be double for dry roots, the hydrodistillation is 33% longer.

β-phellandrene

1,3,8-p-menthatriene

myristicin

apiol

α-pinene

β-pinene

FIG. 10.1 Chemical compound in parsley essential oil.

268

10. Essential oils from Apiaceae family (parsley, lovage, and dill)

In terms of oil components, it was observed that the recovery of monoterpenes and C11 compounds is mostly done up to the 5th hour of hydrodistillation, with a decreasing yield from the 1st to the 5th hour, while the content of phthalides are mainly extracted at the end of the process, their yield increasing by 2.7 folds in this period (Perineau et al., 1992). Another step studied by Perineau et al. (1992) was the separation of essential oils from the aromatic waters obtained in the hydrodistillation. They proposed a liquid–liquid extraction controlled by 1,1,2-trichloro-l,2,2-trifluoroethane (CFC-113) and ethyl ether successively. However, CFCs were phased out under an international convention, thus the use of CFC-113 is no longer an option. The recommended temperatures for this separation are 50–52°C under alkaline pH. Semeniuc et al. (2017) and Semeniuc et al. (2018) used the following procedure to hydrodistill essential oil from dried lovage leaves using a Clevenger apparatus: a distilled water:sample ratio of 15:1 (v/w), an extraction time of 3 h, drying over anhydrous Na2SO4.

10.4 Chemical profile of parsley, dill, and lovage essential oil 10.4.1 Chemical profile of parsley essential oil The essential oil yield of dry parsley was reported between 0.14% (v/w) (Semeniuc et al., 2018; Ouis et al., 2014) and 0.2% (v/w) (Linde et al., 2016). The chemical profile of parsley essential oil varies because of an array of factors related to the herb cultivation and processing (Section 10.2.1), extraction method (Section 10.3.1), but also plant organ used for the extraction procedure (Table 10.3). Some of the major components identified in parsley essential oil are monoterpenes, and the content of the main compounds varying widely: α-pinene (2.1%–37.5%), β-pinene (1.3%– 26.6%), β–myrcene (0.1%–12.71%), apiol (10.1%–50.3%), β-phellandrene (4.9%–32.44%), myristicin (14.0%–18.3%), 1,3,8-p-menthatriene (13.93%) (Table 10.3). But also other minor compounds were reported such as: α-thujene (0.2–0.5%), camphene (0.2%), sabinene (0.42%–1.7%), α-phellandrene (0.1%–2.93%), p-cymene (1.65%), terpinolene (1.5%–3.76%), υ-terpinene (0.1%–0.68%), elemicin (0.6%–2.4%), 1-allyl-2,3,4,5-tetramethoxybenzene (12.8%), 2,6-dimethylstyrene (6.43%), trans-β-ocimene (0.13%), β-terpinyl acetate (0.24%), β-gurjunene (2.8%), z-β-farnesene (4.3%), γ-curcumene (8.0%), pathulenol (8.9%), β-sesquiiphellandrene (2.1%) (Table 10.3) (Fig. 10.1). ISO 3527 (ISO, 2016) states the limits of the main compounds of parsley seeds essential oil: myristicin (25%–50%), apiol (5%–35%), α-pinene (10%–22%); β-pinene (7%–15%), 1,2,3,4tetramethoxy-5-allylbenzene (1%–12%), elemicin (1%–13%).

10.4.2 Chemical profile of dill essential oil Dill essential oil can be extracted from all plant organs (roots, stems, leaves, flowers, seeds) but with a chemical composition that varies widely (Table 10.3). Several studies present the essential oil composition is greatly influenced by agronomic factors and environment, as well as by crop type (Section 10.2.2). The essential oil yield of dill aerial parts (also known as weed) varies between 0.06% and 2.0 (v/w), respectively, but essential oil obtained from dill seeds was obtained at higher yields (up to 3.4%).

TABLE 10.3

No. Compound

Chemical composition of parsley, lovage, and dill essential oils depending on the plant part. Lovage, Parsley, rc (%) rc (%) Herb Flowers Herb Seeds Roots

Dill, rc (%)

References

Flowers Weed

Seeds

Fruit

–

0.60

0.30

Kostova et al. (2020) Kaur et al. (2021) Teneva et al. (2021) Kurowska and Gała˛zka (2006) Semeniuc et al. (2018) Spr
ea et al. (2020a)

1.

α-Thujene

0.2–0.5

0.094–0.26

–

2.

α-Pinene

2.1–37.5 5.3

0.93–3.63 2.9

0.091–0.3 0.08–1.2 2.00–9.61

0.13–1.06

2.22

Kostova et al. (2020) Kaur et al. (2021) Jianu et al. (2012) Rana and Amparo Blazquez (2015) Kaur et al. (2019) Teneva et al. (2021) Massango et al. (2017) Linde et al. (2016) Semeniuc et al. (2018) Spr
ea et al. (2020a) Spr
ea et al. (2020b) Miran et al. (2018b) Mirjalili et al. (2010)

3.

Camphene

0.2

0.135–0.33

–

–

0.05

–

0.17

Kostova et al. (2020) Teneva et al. (2021) Kurowska and Gała˛zka (2006) Semeniuc et al. (2018) Spr
ea et al. (2020a)

4.

Sabinene

0.42–1.4 1.7

1.39

3.0

–

0.12

0.68

0.39

Kostova et al. (2020) Kaur et al. (2019) Teneva et al. (2021) Massango et al. (2017) Kurowska and Gała˛zka (2006) Semeniuc et al. (2018) Spr
ea et al. (2020a) Miran et al. (2018b) Mirjalili et al. (2010)

1.1

2.06

Continued

TABLE 10.3

Chemical composition of parsley, lovage, and dill essential oils depending on the plant part—cont’d

No. Compound

Lovage, Parsley, rc (%) rc (%) Herb Flowers Herb Seeds Roots

Dill, rc (%) Flowers Weed

Seeds

Fruit

References

5.

β-Pinene

1.3–26.6 17.7

0.270–0.89 2.9

0.59–0.7

–

–

0.29

0.73

Kostova et al. (2020) Kaur et al. (2019) Massango et al. (2017) Kurowska and Gała˛zka (2006) Linde et al. (2016) Semeniuc et al. (2018) Spr
ea et al. (2020a) Spr
ea et al. (2020b) Miran et al. (2018b) Mirjalili et al. (2010)

6.

β–Myrcene

0.1–12.71 1.3

4.20–11.36 –

0.2

–

–

2.36

0.70

Kostova et al. (2020) Kaur et al. (2019) Massango et al. (2017) Kurowska and Gała˛zka (2006) Linde et al. (2016) Semeniuc et al. (2018) Spr
ea et al. (2020a) Miran et al. (2018b) Ciocarlan et al. (2018) Mirjalili et al. (2010)

7.

α-Phellandrene

0.1–2.93 –

1.53–2.69 –

0.2

32.26

29.12–62.71 0.80–20.61 20.11–61.00 Kostova et al. (2020) Kaur et al. (2021) Jianu et al. (2012) Kaur et al. (2019) Teneva et al. (2021) Kurowska and Gała˛zka (2006) Linde et al. (2016) Semeniuc et al. (2018) Spr
ea et al. (2020a) Miran et al. (2018b) Ciocarlan et al. (2018)

8.

p-Cymene

1.65

–

0.99–20.53 –

0.028

28.66

14.72–22.42 0.77–1.12

4.40

Kostova et al. (2020) Kaur et al. (2021) Jianu et al. (2012) Semeniuc et al. (2018) Spr
ea et al. (2020a) Spr
ea et al. (2020b)

9.

Limonene

10. Terpinolene

12.46

–

1.5—3.76 –

–

–

–

33.22

3.70–26.34 9.60–83.00 18.78 33.00

Kostova et al. (2020) Kaur et al. (2021) Li et al. (2019) Kaur et al. (2019) Semeniuc et al. (2018)

0.093–1.53 –

–

–

–

Kostova et al. (2020) Massango et al. (2017) Linde et al. (2016) Semeniuc et al. (2018) Spr
ea et al. (2020a)

–

0.15

Mirjalili et al. (2010) 11. p-Cymenene

–

–

–

–

–

–

–

0.10

0.27

Kostova et al. (2020) Kaur et al. (2019)

12. β-Linalool

–

–

–

–

–

–

–

0.49

0.18

Kostova et al. (2020) Kaur et al. (2019)

13. p-Cymen-8-ol

–

–

–

–

–

0.34

Kostova et al. (2020)

14. Dill ether

–

–

–

–

–

22.00

0.90–19.63 1.02

9.06

Kostova et al. (2020) Kaur et al. (2021) Kaur et al. (2019) Teneva et al. (2021)

15. Methyl chavicol

–

–

–

–

–

–

–

–

1.91

Kostova et al. (2020)

16. Trans-dihydrocarvone

–

–

–

–

–

–

0.54

3.35–10.99 2.90

Kostova et al. (2020) Kaur et al. (2021) Kaur et al. (2019)

17. p-Cymen-9-ol

–

–

–

–

–

–

–

–

0.41

Kostova et al. (2020)

18. Cis-carveol

–

–

–

–

–

–

–

–

0.51

Kostova et al. (2020)

19. Carvone

–

–

0.051

–

0.115

–

13.10

30.00–89.98 32.26

Kostova et al. (2020) Kaur et al. (2021) Kaur et al. (2019) Spr
ea et al. (2020a) Spr
ea et al. (2020b)

20. Cis-carvone oxide

–

–

–

–

–

–

–

–

0.21

Kostova et al. (2020)

21. Trans-carvone oxide

–

–

–

–

–

–

–

–

0.17

Kostova et al. (2020)

22. Limonen-10-ol

–

–

–

–

–

–

–

–

0.78

Kostova et al. (2020)

23. Carvacrol

–

–

–

–

–

–

0.03

–

0.69

Kostova et al. (2020) Continued

TABLE 10.3

Chemical composition of parsley, lovage, and dill essential oils depending on the plant part—cont’d

No. Compound

Lovage, Parsley, rc (%) rc (%) Herb Flowers Herb Seeds Roots

Dill, rc (%) Flowers Weed

Seeds

Fruit

24. Cis-2,3-pinanediol

–

–

–

–

–

–

–

0.32

0.86

Kostova et al. (2020) Kaur et al. (2019)

25. Isodihydro carveol acetate

–

–

–

–

–

–

–

–

0.31

Kostova et al. (2020)

26. Decyl acetate

–

–

–

–

–

–

–

0.13

Kostova et al. (2020)

27. υ-Terpinene

0.1–0.68 –

0.78–6.84

4.3

–

13.96

0.03–2.02

–

Kaur et al. (2021) Jianu et al. (2012) Li et al. (2019) Kaur et al. (2019) Kurowska and Gała˛zka (2006) Semeniuc et al. (2018) Spr
ea et al. (2020a)

References

Miran et al. (2018b) Ciocarlan et al. (2018) 28. Phellandral

–

–

–

–

–

–

34.17–52.70 –

Jianu et al. (2012)

29. Apiol

10.1–50.3 –

–

–

–

–

16.79–32.78 –

Kaur et al. (2021) Jianu et al. (2012) Kurowska and Gała˛zka (2006) Linde et al. (2016)

30. β-Phellandrene

4.9–32.44 –

4.65–53.89 60.5

1.26–22.39 –

–

–

Massango et al. (2017) Kurowska and Gała˛zka (2006) Linde et al. (2016) Semeniuc et al. (2018) Spr
ea et al. (2020a)

–

Spr
ea et al. (2020b) Miran et al. (2018b) Ciocarlan et al. (2018) Mirjalili et al. (2010)

31. Myristicin

14.0–18.3 –

–

–

–

–

–

Massango et al. (2017) Kurowska and Gała˛zka (2006) Linde et al. (2016)

32. Elemicin

0.6–2.4

–

–

–

–

–

–

–

–

Massango et al. (2017) Kurowska and Gała˛zka (2006)

33. 1-Allyl-2,3,4,5tetramethoxybenzene

12.8

–

–

–

–

–

–

–

–

Kurowska and Gała˛zka (2006)

34. 2,6-Dimethylstyrene

6.43

–

–

–

35. 1,3,8-p-Menthatriene

13.93

–

–

–

–

–

–

–

–

Semeniuc et al. (2018)

36. Trans-β-ocimene

0.13

–

7.00

–

13.0

–

–

–

–

Semeniuc et al. (2018) Miran et al. (2018b)

37. β-Terpinyl acetate

0.24

–

12.73–33.6 –

–

–

–

–

–

Semeniuc et al. (2018) Spr
ea et al. (2020a)

Semeniuc et al. (2018)

Ciocarlan et al. (2018) 38. (Z)-Ligustilide

–

–

11.18–22.2 –

5.8–8.5

–

–

–

–

Spr
ea et al. (2020a) Spr
ea et al. (2020b) Miran et al. (2018b) Ciocarlan et al. (2018)

39. Kessane

–

–

–

–

2.1

–

–

–

–

Spr
ea et al. (2020b)

40. Spathulenol

–

–

–

–

6.3

–

–

–

–

Spr
ea et al. (2020b)

41. 3-Butylphthalide

–

–

–

–

6.8

–

–

–

–

Spr
ea et al. (2020b)

42. z-Butylidenephthalide

–

–

–

–

29.0

–

–

–

–

Spr
ea et al. (2020b)

43. e-Butylidenephthalide

–

–

–

–

8.3

–

–

–

–

Spr
ea et al. (2020b)

44. Neocnidilide

–

–

–

–

8.9–11.6

–

–

–

–

Spr
ea et al. (2020b) Miran et al. (2018b) Continued

TABLE 10.3 Chemical composition of parsley, lovage, and dill essential oils depending on the plant part—cont’d

No. Compound

Lovage, Parsley, rc (%) rc (%) Herb Flowers Herb Seeds Roots

Flowers Weed

Seeds

Fruit

45. e-Ligustilide

–

–

–

–

–

–

–

1.5–1.87

Dill, rc (%)

–

References

Spr
ea et al. (2020b) Miran et al. (2018b)

46. α-Terpineol acetate

–

–

–

47. β-Gurjunene

–

2.8

–

48. z-β-farnesene

–

4.3

–

49. γ-Curcumene

–

8.0

50. Spathulenol

–

51. β-Sesquiiphellandrene

–

–

42.1

–

–

–

–

Miran et al. (2018b)

–

–

–

–

–

Mirjalili et al. (2010)

0.2

–

–

–

–

–

Mirjalili et al. (2010)

–

0.3

–

–

–

–

–

Mirjalili et al. (2010)

8.9

–

2.7

–

–

–

–

–

Mirjalili et al. (2010)

2.1

–

5.1

–

–

–

–

–

Mirjalili et al. (2010)

10.4 Chemical profile of parsley, dill, and lovage essential oil

275

The major compounds present in essential oils extracted from all herb parts are essentially carvone, limonene, and α-phellandrene, but may vary depending on many factors (different geographic origins and extraction method) (Sections 10.2.2 and 10.3.2) (Fig. 10.2). Usually, dill is considered to have four chemotypes characterized by the presence of (1) myristicin; (2) dill apiole; (3) myristicin and dill apiole; (4) neither myristicin nor dill apiole (Bailer et al., 2001; Tibaldi et al., 2010). Some of the major components identified in dill weed and aerial organs essential oil are: α-pinene (0.08%–9.61%), α-phellandrene (29.12%–62.71%), p-cymene (14.72%–28.66%), limonene (3.70%–33.22%), dill ether (0.90%–22.00%), carvone (13.10%), and υ-terpinene (13.96%). But also other minor compounds were reported, such as: α-thujene (2.06%), camphene (0.05%), sabinene (0.12), trans-dihydrocarvone (0.54%), and carvacrol (0.03%) (Table 10.3). In dill seeds essential oil usually, the following major compounds were reported: α-phellandrene (0.80%–61.00%), limonene (9.60%–83.00%), dill ether (1.02%–9.06%), trans-dihydrocarvone (2.90%–10.99%), carvone (30.00%–89.98%), phellandral (34.17%– 52.70%), and dill apiol (16.79%–32.78%), and the following minor compounds: α-thujene (0.30%–0.60%), α-pinene (0.13%–2.22%), camphene (0.17%), sabinene (0.39%–0.68%), β-pinene (0.29%–0.73%), β–myrcene (0.70%–2.36%), p-cymene (0.77%–4.40%), terpinolene (0.15%), p-cymenene (0.10%–0.27%), β-linalool (0.18%–0.49%), methyl chavicol (1.91%), p-cymen-9-ol (0.41%), cis-carveol (0.51%), cis-carvone oxide (0.21%), trans-carvone oxide (0.17%), limonen-10-ol (0.78%), carvacrol (0.69%), cis-2,3-pinanediol (0.32%–0.86%), isodihydro carveol acetate (0.31%), decyl acetate (0.13%), and υ- terpinene (0.03%– 2.02%) (Table 10.3).

-phellandrene

dill ethe r

carvone

-pinene

dill apiole

geraniol

-phellandrene

myristicin

-myrcene

FIG. 10.2 Chemical compound in dill essential oil.

276

10. Essential oils from Apiaceae family (parsley, lovage, and dill)

10.4.3 Chemical profile of lovage essential oil Terpenes and phthalides are the main chemical classes of compounds dominating lovage essential oils (Mirjalili et al., 2010; Venskutonis, 2016). However, various factors influence the chemical profile of lovage essential oil (Section 10.2.3), the compounds concentration in different anatomical parts may vary widely as well (Section 10.2.3) (Table 10.3), together with the extraction method (Section 10.3.3). The hydrodistillation of aerial parts yielded essential oil between 0.28% (v/w) (Semeniuc et al., 2018) and 2.5% (v/w) (Miran et al., 2018b). Some of the major chemical compounds reported in lovage herb essential oil are: β-pinene (0.270%–17.7%), β–myrcene (1.3%–11.36%), p-cymene (0.99%–20.53%), β-phellandrene (4.65%–53.89%), β -terpinyl acetate (12.73%–33.6%), and (Z)-ligustilide (11.18%–22.2%) with the following minor components: α-thujene (0.094%–0.26%), α-pinene (0.93%–5.3%), camphene (0.135%–0.33%), sabinene (1.39%–1.7%), terpinolene (0.093%–1.53%), carvone (0.051%), υ-terpinene (0.78%–6.84%), trans-β-ocimene (7.00%), β-gurjunene (2.8%), z-βfarnesene (4.3%), γ-curcumene (8.0%), spathulenol (8.9%), and β-sesquiiphellandrene (2.1%) (Table 10.3). The lovage seed essential oil are rich in β-phellandrene (60.5%), while the roots are rich in: β-phellandrene (1.26%–22.39%), trans-β-ocimene (13.0%), α-terpineol acetate (42.1%), neocnidilide (8.9%–11.6%), z-butylidenephthalide (29.0%) (Table 10.3). Some of the following minor compounds of lovage seed essential oil were reported: α-pinene (2.9%), sabinene (1.1%), β-pinene (2.9%), z-β-farnesene (0.2%), γ-curcumene (0.3%), spathulenol (2.7%), β-sesquiiphellandrene (5.1%), while for roots: α-pinene (0.091%–0.3%), sabinene (3.0%), β-pinene (0.59–0.7%), β–myrcene (0.2%), p-cymene (0.028), carvone (0.115%), υ- terpinene (4.3%), (Z)-ligustilide (5.8%–8.5%), kessane (2.1%), spathulenol (6.3%), 3-butylphthalide (6.8%), 3-butylphthalidee-butylidenephthalide (8.3%), and e-ligustilide (1.5%–1.87%) (Table 10.3) (Fig. 10.3).

10.5 Bioactivity of parsley, dill, and lovage essential oil 10.5.1 Antioxidant activity of parsley, dill, and lovage essential oil The essential oils of parsley, dill, and lovage have shown good antioxidant activity due to their chemical structure. The essential oil extracted from parsley showed good antioxidant properties, compared with vitamin C (control) (Romeilah et al., 2010). It was reported that parsley essential oils displayed an antioxidant activity at 5, 10, 20, and 50 g/L, exhibiting an inhibition of DPPH radical of 28.87%, 44.22%, 53.34%, and 64.28% respectively and ferric reducing power of 0.40, 0.56, 0.82, and 0.93 mmol/L Trolox respectively (Marin et al., 2016). Zhang et al. (2006) reported that parsley essential oil showed a significant antioxidant activity. Among the components of the essential oil, they concluded that myristicin, which had the highest relative concentration (32.75%), had only a moderate antioxidant activity. However, apiol, the second most important compound (17.54%), was the major contributor to the total antioxidant activity of the tested oil. Thus, this might suggest that parsley essential oil,

277

10.5 Bioactivity of parsley, dill, and lovage essential oil

β-phellandrene

β-myrcene

p-cymene

α-terpinolene

α-terpineol acetate

(Z)-butylidenephthalide

FIG. 10.3 Chemical compound in lovage essential oil.

together with its components myristicin and apiol can be potential natural alternatives to the synthetic antioxidants. Semeniuc et al. (2018) reported that parsley and lovage essential oils are rich in oxygenated monoterpenes, and that they have significant antioxidant activity. Sintim et al. (2015) suggested that the antioxidant capacity of dill seeds is related to the essential oil content of d-limolene and p-cymenene and that it varies during the hydrodistillation process. Thus, it was shown that the essential oil extracted in the first 2 min of the extraction are the most potent antioxidants. Dill essential oil, generally obtained from its seeds and leaves, contains monoterpene hydrocarbons and oxygenated monoterpenes, which are responsible for its antioxidant properties (Kaur et al., 2021). A similar study, reported that compounds from the monoterpenes class, that are also found in dill essential oils, such as: carvone, myrcene, and γ-terpinene showed a high antioxidant activity measured by the DPPH radical scavenging assay (Ciesla et al., 2012). The results reported by Kaur et al. (2019) compared the antioxidant activity of the polar and non-polar fractions of the dill seeds essential oil and reported the highest antioxidant activity for the polar compounds, with carveol as the most potent compound. The antioxidant activity of dill root essential oil and potential use against oxidative stress was also reported by Saleh et al. (2017). Dill essential oil nanoemulsions showed good antioxidant potential as well, with an IC50 of 500 μg/mL as measured by the DPPH radical scavenging assay and 420 μg/mL by the ABTS assay (Tavakkol et al., 2019). This report has therapeutic potential, as these dill essential oil nanoemulsions could be used as antioxidants for oxidative stress.

278

10. Essential oils from Apiaceae family (parsley, lovage, and dill)

The antioxidant activity of lovage essential oil was showed to be dependent on the plant developmental stages (Mohamadi et al., 2017). The highest antioxidant activity was reported for oils extracted from the flowering stage of dill herb (83%), followed by the vegetative stage (68%), and the seed-producing stage generated the oil with the lowest antioxidant activity (60%). The major compounds identified in lovage oil were: β-phellandrene and α-terpinyl acetate, γ-cadinene, and sabinene, which were responsible for the high reported antioxidant properties.

10.5.2 Antimicrobial activity of parsley, dill, and lovage essential oil Several studies have reported wide-scale antimicrobial property of parsley, dill, and lovage essential oils (Semeniuc et al., 2018; Semeniuc et al., 2017; Chahal et al., 2017; Jianu et al., 2012; Kaur et al., 2021). An overview of the antifungal and antibacterial activity of parsley, dill, and lovage essential oils was summarized in Tables 10.4 and 10.5. Various studies reported that parsley essential oils were effective against different microorganisms. Parsley essential oil extracted from aerial parts inhibited ATCC stains Escherichia coli (ATCC 29194) and clinical isolated K. pneumoniae, with a minimal inhibitory concentration (MIC) of 32 mg/mL ( Jugreet and Mahomoodally, 2020). It showed a medium antibacterial effect against Bacillus spisizeciaela (ATCC 6633), Staphylococcus aureus (ATCC 25923), Staphylococcus aureus (MRSA), and clinical isolated Enterococcus faecalis, with a MIC of 16 mg/mL. Also, it showed a mild bacteriostatic activity against Staphylococcus epidermidis (ATCC 12228) (MIC 4 mg/mL), but no effect against Pseudomonas aeruginosa (ATCC 27853). Parsley essential oils were moderately effective against Listeria innocua, but it did not inhibit Pseudomonas fluorescens (Marin et al., 2016). Parsley oil obtained by supercritical fluid extraction inhibited Bacillus stains with antibacterial activity ranging from strong to moderately strong (Misic et al., 2020). However, its antibacterial activity was weak against Staphylococcus aureus, Listeria spp., and Salmonella Enteritidis (Misic et al., 2020). Shaaban (2012) tested the susceptibility of isolated uropathogenic bacteria to parsley essential oil. The results showed that the essential oil had a stronger effect against Gram-positive cocci (56%) than against Gram-negative bacilli (48%), with a much lower inhibition (29%) of E. coli. On another hand, Semeniuc et al. (2017) reported only a low antibacterial activity against S. aureus (ATCC 6538P), E. coli (ATCC 25922), B. cereus (ATCC 11778), P. aeruginosa (ATCC 27853), and S. typhimurium (ATCC 14028). Linde et al. (2016) assessed the antibacterial properties of essential oils extracted from the aerial parts of parsley against 7 microorganisms. Parsley essential oils showed bacteriostatic activity at low concentrations against L. monocytogenes (NCTC 7973), S. enterica subsp. enterica (ATCC 13311), and S. aureus (ATCC 6538) strains. Moreover, it exhibited a bactericidal effect at minimum bactericidal concentration (MBC) as low as 0.15–10.00 mg/mL. The oil was least effective against E. cloacae (clinical isolate), and E. coli (ATCC 35218). The most susceptible bacteria were P. aeruginosa (ATCC 27853), S. enterica subsp. enterica (ATCC 13311) and S. aureus (ATCC 6538). Additionally, the oil was effective against all fungi, thus presenting good fungistatic activity. The most susceptible fungi were Penicillium ochrochloron (ATCC 9112), Trichoderma viride (IAM 5061) and Penicillium funiculosum (ATCC 8725). The values

TABLE 10.4 Antimicrobial (antifungal and antibacterial) activity of parsley, dill, and lovage essential oils. Essential oils Parsley

Plant part Dried leaves

Commercially available

Bacterial strain

Microbial load/ volume

Concentration of EO/volume or weight

Zone of inhibition/ diameter of paper disc

Minimum inhibitory concentration

S. aureus (ATCC 25913)

1.0  10 CFU/mL/ 100 μL

50% EO in DMSO/10 μL

15.0 mm/6 mm

0.3%

E. coli (ATCC 8739)

14.0 mm/6 mm

1.0%

S. Typhimurium (PTCC 1709)

12.5 mm/6 mm

1.0%

S. aureus (ATCC 13563)

8

1.0  108 CFU/mL/ 100 μL

100% EO/ 24 mg

33.0 mm/6 mm

P. aeruginosa (ATCC 9027)

16.0 mm/6 mm

Escherichia coli O157:H7 (ATCC 35150)

13.0 mm/6 mm

Salmonella Typhimurium (ATCC 14028)

16.0 mm/6 mm

Dried leaves (winter season, summer season)

E. coli (UNS)

UNS

100% EO/5 μL

Dried leaves

Salmonella enteritidis (ATCC 13076)

1.5  108 CFU/mL/ 10 μL

10% EO/100 μL

Osman et al. (2009) 22.68 μg/mL

Semeniuc et al. (2018)

5.14 μg/mL

9.46 mm/9 mm

22.68 μg/mL

S. aureus (ATCC 6538P)

10.07 mm/9 mm

10.80 μg/mL

P. aeruginosa (ATCC 27853)

NI

47.62 μg/mL

E. coli (ATCC 25922)

9.60 mm/9 mm

10.80 μg/mL

B. cereus (ATCC 11778)

Fahimi et al. (2015)

Elgayyar et al. (2001)

10.0–29.0 mm/UNS

Listeria monocytogenes (ATCC 19114) Dried leaves

Reference

1.5  108 CFU/mL/ 10 μL

40 μL EO 10% EO/100 μL

Semeniuc et al. (2017)

Continued

TABLE 10.4 Antimicrobial (antifungal and antibacterial) activity of parsley, dill, and lovage essential oils—cont’d Essential oils

Plant part

Zone of inhibition/ diameter of paper disc

Minimum inhibitory concentration

9.77 mm/9 mm

47.62 μg/mL

UNS

UNS

UNS

UNS

17.0, 21.0, 16.0 mm/UNS

3.8, 3.7, 3.6 mg /mL

P. aeruginosa (ATCC 27852)

11.0, 8.0, 9.0 mm/UNS

> 15.2, > 14.4, > 14.4 mg/mL

E. coli (ATCC 25922)

19.0, 18.0, 15.0 mm/UNS

15.2, 7.2, 7.2 mg/mL

Bacillus subtilis ATCC 9372

25.0, 36.0, 35.0 mm/UNS

3.8, 0.9, 0.9 mg/mL

Enterococcus faecalis ATCC 15753

19.0, 17.0, 13.0 mm/UNS

15.2, 7.5, 7.2 mg/mL

Staphylococcus epidermidis ATCC 12228

23.0, 26.0, 25.0 mm/UNS

1.9, 0.9, 1.8 mg /mL

Klebsiella pneumoniae ATCC 3583

10.0, 10.0, 9.0 mm/UNS

> 15.2, > 14.4, > 14.4 mg/mL

Bacterial strain

Microbial load/ volume

Concentration of EO/volume or weight

S. Typhimurium (ATCC 14028) Aerial parts

Listeria innocua (CECT 910)

UNS

UNS

Pseudomonas fluorescens (CECT 844) Lovage

Immature fruits, green mature fruits, ripened fruits

S. aureus (ATCC 25923)

UNS

Aerial parts

Mycobacterium tuberculosis (H37Rv)

108 CFU/mL

Roots at flowering stage and fruiting stage

S. aureus (ATCC 25923)

108 CFU/mL

Enterococcus faecium (Vancomycin-resistant clinical strain)

100% EO/10 μL

100 μL

UNS

Reference

Marin et al. (2016)

Mirjalili et al. (2010)

252 μg/mL

Miran et al. (2018b)

32.0, 32.0 mg/mL

Miran et al. (2018a)

32.0, 32.0 mg/mL

Dried leaves

E. coli (ATCC 25922)

32.0, 32.0 mg/mL

Pseudomonas aeruginosa (PTCC1430)

>32.0, >32.0 mg/mL

S. enteritidis (ATCC 13076)

1.5  108 CFU/mL/ 10 μL

10%EO/100 μL

10.80 μg/mL 2.45 μg/mL

L. monocytogenes (ATCC 19114) Dried leaves

Dill

Commercially available

9.53 mm/9 mm

47.62 μg/mL

Staphylococcus aureus (ATCC 6538P)

10.38 mm/9 mm

2.45 μg/mL

P. aeruginosa (ATCC 27853)

9.44 mm/9 mm

22.68 μg/mL

E. coli (ATCC 25922)

9.85 mm/9 mm

10.80 μg/mL

Salmonella typhimurium (ATCC 14028)

10.29 mm/9 mm

47.62 μg/mL

Bacillus cereus (ATCC 11778)

S. aureus (ATCC 6538)

Semeniuc et al. (2018)

1.5  108 CF/mL/ 10 μL

107 CFU/mL

40 μL EO 10% EO/100 μL

100% EO/50 μL

15.1 mm/8 mm

B. subtilis (ATCC 6633)

14.4 mm/8 mm

E. coli (ATCC 8739)

15.8 mm/8 mm

P. aeruginosa (ATCC 9027)

14.1 mm/8 mm

Salmonella abony (NTCC 6017)

16.9 mm/8 mm

Saccharomyces cerevisiae (ATCC 2601)

16.3 mm/8 mm

Semeniuc et al. (2017)

Kostova et al. (2020)

Continued

TABLE 10.4 Antimicrobial (antifungal and antibacterial) activity of parsley, dill, and lovage essential oils—cont’d Essential oils

Plant part

Seeds

Fruits

Bacterial strain

Microbial load/ volume

Concentration of EO/volume or weight

Zone of inhibition/ diameter of paper disc

Candida albicans (ATCC 10231)

16.3 mm/8 mm

Aspergillus brasiliensis (ATCC 16404)

25.9 mm/8 mm

C. albicans (ATCC 62342)

5  106 cells/mL

100 μL

Minimum inhibitory concentration

8.75 mg/mL

C. albicans (ATCC 23778)

8.75 mg/mL

C. albicans (ATCC 23651)

8.75 mg/mL

C. albicans (ATCC 23609)

8.75 mg/mL

C. albicans (ATCC 24073)

8.75 mg/mL

C. albicans (ATCC 23536)

8.75 mg/mL

Candida parapsilosis (ATCC 2340)

8.75 mg/mL

C. parapsilosis (ATCC 23459)

8.75 mg/mL

C. glabrata (ATCC 23453)

17.5 mg/mL

Candida krusei (ATCC 23932)

8.75 mg/mL

S. aureus (ATCC 6538) S. aureus (ATCC 25923) S. aureus (ATCC 29213)

108 CFU/mL

8% EO in DMSO

>10 mg/mL >10 mg/mL >10 mg/mL

Reference

Vieira et al. (2019)

Ruangamnart et al. (2015)

Flowers

Methicillinresistant S. aureus (MRSA) (ATCC 43300) B. subtilis (ATCC 6633)

>10 mg/mL

K. pneumoniae (ATCC 700603)

10 mg/mL

Salmonella Typhimurium (ATCC 14028)

10 mg/mL

E. coli (ATCC 8739)

10 mg/mL

P. aeruginosa (ATCC 9027)

>10 mg/mL

P. aeruginosa (ATCC 27853)

>10 mg/mL

Shigella flexneri (ATCC 12021),

>10 mg/mL

3  106 cells/mL

20 μL

9 mm/6 mm

K. pneumoniae (ATCC 13882),

16.93 mm/6 mm

S. typhimurium (ATTC 14028), S. aureus (ATCC 25923),

NI. N.I.

E. coli (ATCC 25922), Streptococcus pyogenes (ATTC 19615

14.96 mm/6 mm N.I.

Clostridium perfringens (ATCC13124).

N.I.

Notes: UNS, unspecified; DMSO, dimethyl sulfoxide; N.I, no inhibition.

Jianu et al. (2012)

TABLE 10.5

Pharmacological properties of parsley, dill, and lovage essential oils.

Plant

Plant part

Pharmacological activity

Effect

References

Parsley

Herb

Antioxidant activity

Intercept the oxidative processes in the human body

Romeilah et al. (2010) Marin et al. (2016) Zhang et al. (2006) Khalil et al. (2015)

Seed

Mert and Timur (2017) Wei and Shibamoto (2007)

NA

Hepato-cardio protective

Protective effect against the Cisplatin-induced hepato-cardiotoxicity

Abdellatief et al. (2017)

NA

Hepatoprotective

Protective effect against alcohol-induced hepatotoxicity

Abou Seif (2014)

Aerial part

Decreased aspartate transaminase (AST), alanine aminotransferase (ALT), alkaline phosphatase (ALP) and bilirubin serum levels; increased serum total protein and albumin

Khalil et al. (2015)

NA

Hepatoprotective effect against cadmium chloride toxicity

El-Shall and Badr (2016)

Escherichia coli (ATCC 29194), Klebsiella pneumoniae, Bacillus spisizeciaela (ATCC 6633), Staphylococcus aureus (ATCC 25923), S. aureus (MRSA), Enterococcus faecalis, Staphylococcus epidermidis (ATCC 12228)

Jugreet and Mahomoodally (2020)

Seed

Bacillus cereus, Bacillus circulans

Misic et al. (2020)

NA

64 bacterial isolates uropathogens: E. coli (28 isolates), Klebsiella pneumonia (9 isolates), Pseudomonas aeruginosa (6 isolates), Proteus mirabilis (6 isolates), S. aureus (5 isolates), E. faecalis (4 isolates), Morganella morganii (4 isolates), Pseudomonas fluorescens (2 isolates)

Shaaban (2012)

Fruits

S. aureus ATCC 6538, E. coli ATCC 8739, Micrococcus luteus ATCC 9341

Khalil et al. (2018)

Leaves

B. cereus (ATCC 11778), S. aureus (ATCC 6538P), E. coli (ATCC 25922), Salmonella typhimurium (ATCC 14028)

Semeniuc et al. (2017)

Aerial part

Antibacterial

Leaves

Immunomodulating activity

Suppress cellular and humoral immune response

Yousofi et al. (2012)

NA

Protective effect against testicular toxicity

Increase testosterone level, sperm count and motility; decrease chromosomal abnormalities induced by Zearalenone

Abdel-Wahhab et al. (2006)

NA

Protective role against kidney toxicity

Maintained a natural appearance of glomeruli and urinary tubules and absence Arcoxia-induced hemorrhage

Al-Ghamdi and AL-Amri (2016)

Dill

E. coli 2799, P. aeruginosa, B. cereus

Saleh et al. (2017)

NA

Brochothrix thermosphacta, Closridium botulinum type B Clostridium botulinum type E, Clostridium perfringens, Lactobacillus sakei, S. aureus.

Nevas et al. (2004)

NA

64 Bacterial isolates uropathogens: E.coli (28 isolates), Klebsiella pneumonia (9 isolates), P. aeruginosa (6 isolates), P. mirabilis (6 isolates), S. aureus (5 isolates), E. faecalis (4 isolates), M. morganii (4 isolates), P. fluorescens (2 isolates)

Shaaban (2012)

Seeds

B. cereus, M. luteus, S. aureus, Streptococcus faecalis, Enterobacteriaceae, Alcaligenes faecalis, E. coli, P. aeruginosa,

Chao et al. (2000)

Fruits

S. aureus ATCC 6538, E. coli ATCC 8739, M. luteus ATCC 9341

Khalil et al. (2018)

root

Antibacterial

NA

Wound healing

Dill essential oil ointment accelerating healing of infected wounds with MRSA isolated from burn wounds

Manzuoerh et al. (2019)

Root

Antioxidant

intercept the oxidative processes in the human body

Saleh et al. (2017)

Intercept the oxidative stress and cancer in the human body

Tavakkol et al. (2019)

Aspergillus niger, Candida albicans, Sacharomyces cerevaceae

Saleh et al. (2017)

Seeds

Aspergillus flavus, Aspergillus oryzae, Aspergillus niger, Alternaria alternata

Tian et al. (2011)

Seeds

C. albicans, Rhizopus oligosporus

Chao et al. (2000)

Seeds

C. albicans ATCC 64550

Chen et al. (2014)

Seeds

Aspergillus flavus CCAM 080001

Tian et al. (2012)

NA Root

Antifungal

Leaves and seeds

Anti-inflammatory

Reduction of the inflammation

Naseri et al. (2012)

NA

Spasmolytic

Reduction of intestine contractions

Dhiman et al. (2017)

NA

Antifoaming and carminative effect

Relieve of discomfort and distension in the gastrointestinal tract

Harries et al. (1977)

Aerial part

Hypolipidemic activity

Decreased total cholesterol, triglycerides, low density lipoprotein cholesterol (LDL-C) Increased high density lipoprotein cholesterol (HDL-C)

Hajhashemi and Abbasi (2008)

Seed

Hepatoprotective

Decreased aspartate transaminase (AST), alanine aminotransferase (ALT), alkaline phosphatase (ALP) and bilirubin serum levels; Increase serum total protein and albumin

Rabeh et al. (2014)

Improvement of the hepatocellular characteristics; hepatic lobules kept normal morphology, nearly normal histology of hepatocytes

Abd El Monein Solaiman and Mahmoud Elagawany (2015)

NA

Continued

TABLE 10.5 Plant Lovage

Pharmacological properties of parsley, dill, and lovage essential oils—cont’d

Plant part

Pharmacological activity

Aerial part

Antibacterial

Effect

References

Bacillus subtilis CNMN BB-01, P. fluorescens CNMN-PFB-01, Xanthomonas campestris, Erwinia amylovora, Erwinia carotovora

Ciocarlan et al. (2018)

Flower and fruits

B. subtilis ATCC 9372, E. faecalis ATCC 15753, S. aureus ATCC 25923, S. epidermidis ATCC 12228, E. coli ATCC 25922, P. aeruginosa ATCC 27852, and K. pneumoniae ATCC 3583

Mirjalili et al. (2010)

NA

B. cereus, B. thermosphacta, Closridium botulinum type B, C. botulinum type E, C. perfringens, L. sakei and S. aureus

Nevas et al. (2004)

Aerial part

MDR Mycobacterium tuberculosis

Miran et al. (2020)

leaves

B. cereus (ATCC 11778), S. aureus (ATCC 6538P), Pasteurella aeruginosa (ATCC 27853), E. coli (ATCC 25922), S. typhimurium (ATCC 14028)

Semeniuc et al. (2017)

Aerial part

Antifungal

Candida utilis

Ciocarlan et al. (2018)

Aerial part

Antioxidant

Intercept the oxidative processes in the human body

Mohamadi et al. (2017)

Where: NA—not available.

10.5 Bioactivity of parsley, dill, and lovage essential oil

287

of minimum fungicidal concentration (MFC) varied between 1.25 and 2.50 mg/mL (Linde et al., 2016). Romeilah et al. (2010) tested the antiviral activity of parsley essential oil against herpes simplex virus 1 (HSV-1). The results showed that the incubation of virus-infected cells with 200, 500 and 1000 μg/mL of parsley essential oil increased the viability of those cells with 52.59%, 59.54% and 64.46% respectively, when compared to untreated virus-infected cells (control). Thus, parsley essential oil significantly increased the antiviral activity percentages. Kaur et al. (2021) assessed the antibacterial activity of dill seeds essential oil. It inhibited Staphylococcus aureus (ATCC 25923) and Escherichia coli (ATCC 25922) but had no effect against Pseudomonas aeruginosa (ATCC 27853). Similarly, essential oil extracted from the aerial parts of dill was the most effective against the tested E. coli strain than against P. aeruginosa, S. aureus, or B. cereus (Sharopov et al., 2013). Additionally, essential oil extracted form dill seeds inhibited Staphylococcus aureus, Escherichia coli, and Yersinia enterocolitica with a diameter of inhibition zone (DIZ) ranging from 36 to 69 mm (Chahal et al., 2017). Salmonella typhimurium was only moderately inhibited by the oil (DIZ of 26 mm). However, there was no effect reported for Lactobacillus plantarum, Listeria monocytogenes, or Pseudomonas aeruginosa. Jianu et al. (2012) indicated that the essential oils extracted from dill seeds extracted in the 3 different development stages exhibited different antibacterial activities. Thus, essential oils isolated from mature seeds were most effective against C. perfringens and S. typhimurium, while the essential oils extracted from inflorescences displayed only moderately effective. On the other hand, none of the tested oils inhibited Streptococcus pyogenes and S. aureus. Essential oil extracted from dill roots showed the highest antibacterial activity against E. coli 2799, followed by P. aeruginosa, with a moderate activity against B. cereus, depending on the different dosage level (400–800 μg/well), but with a higher potency than tetracycline (Saleh et al., 2017). On the other hand, the oil had no effect against Enterococcus faecalis. However, it showed a moderate to weak activity compared to synthetic antibiotics against S. aureus, B. subtilis, E. coli 12079, S. enteritidis 1375, S. typhi, and Acetobacter aceti (Saleh et al., 2017). Dill essential oil also showed an inhibitory effect against Brochothrix thermosphacta, Closridium botulinum type B, Clostridium botulinum type E, Clostridium perfringens, Lactobacillus sakei, and S. aureus, with the highest efficiency against the latter (Nevas et al., 2004). Additionally, the Gram-positive bacteria were more susceptible to dill essential oil than Gramnegatives, with S. aureus, Clostridium perfringens, and Clostridium botulinum type E being the most susceptible (Nevas et al., 2004). Shaaban (2012) tested the effect of dill essential oil against bacteria isolated from the urinary tract (UTI). The results showed that among other plants, dill oil inhibited the most effectively E. coli isolates, which were reduced by 61%. Additionally, Gram-positive bacteria were inhibited by 56%, while other Gram-negatives by only 33%. Overall, dill essential oil inhibited 48% of all tested UTI bacteria. Several studies have assessed the antifungal activity of essential oils extracted from various dill parts. Dill seeds essential oil showed antifungal activity against Aspergillus niger by producing degeneration in conidial heads and affecting the morphology of the hyphae (Chahal et al., 2017; Kaur et al., 2021). The antifungal activity of dill root essential oil was analyzed by Saleh et al. (2017) and it was observed that the highest inhibition zone was shown against A. niger at 800 μg/well, followed by Candida albicans and Sacharomyces cerevaceae, but Trichoderma spp. seemed to be resistant.

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Tian et al. (2011) tested the antifungal activity of dill seed oil against Aspergillus flavus, Aspergillus oryzae, Aspergillus niger and Alternaria alternata and reported a 2.0 μL/mL MIC for all the tested fungi. Similarly, Tian et al. (2012) acknowledged dill seeds essential oil as a potential natural antifungal substance. Additionally, they proposed an inhibition mechanism of A. flavus: the oil disrupts the permeability of the plasma membrane, and thus, reactive oxygen species (ROS) van accumulate which, in turn can induce mitochondrial dysfunctions. Several studies reported the antimicrobial activity of lovage essential oils. It was shown to be linked to the compounds present in the oils, their functional groups, but also on their synergic interactions (Ciocarlan et al., 2018). The antibacterial and antifungal properties of lovage essential oil were assessed against five bacteria Bacillus subtilis, Pseudomonas fluorescens, Xanthomonas campestris, Erwinia amylovora, Erwinia carotovora, and Candida utilis. Lovage essential oil was both an antibacterial and an antifungal agent, with MBC ranging between 0.015% and 0.030% (Ciocarlan et al., 2018). The antimicrobial activity of lovage essential oil can be linked to the presence and concentration of the major compounds such as as β-phellandrene, α-terpinyl acetate, and (Z)–ligustillide. The mechanism of action of these compounds was explained by their effect on the permeability of the cell wall and of the cytoplasmic membrane, causing breakage, followed by leakage of the intracellular content. It was also reported that the developmental stages of the lovage herb influenced the antibacterial activity of the essential oil (Mirjalili et al., 2010). The obtained essential oils were effective against the tested Gram-positive bacteria and the Gram-negative E. coli. S. epidermidis ATCC 12228 was the most susceptible among the tested bacteria to oil obtained from mature and ripe fruits. This oil was also the most effective, of the tested types, against B. subtilis ATCC 9372 (MIC ¼ 0.90 mg/mL). The most resistant bacteria proved to be K. pneumoniae ATCC 3583 and P. aeruginosa ATCC 27852 with the highest MICs (14.4–15.2 mg/mL). Lovage essential oil inhibited B. cereus, Brochothrix thermosphacta, Clostridium botulinum type B, Clostridium botulinum type E, Clostridium perfringens, Lactobacillus sakei, and S. aureus, as well (Nevas et al., 2004). Similar to the results reported by Mirjalili et al. (2010) the Gram-positives were more susceptible that Gram-negatives, with the most sensitive bacteria being Clostridium botulinum type E, Clostridium perfringens, and S. aureus. Miran et al. (2018b) evaluated the antibacterial activity of lovage essential oil against four bacteria and reported the efficacy of the oil extracted from the herbs at fruiting stage against S. aureus, Enterococcus faecium, and E. coli. However, its inhibition of Pseudomonas aeruginosa was weak. Similarly, lovage essential oil of aerial part showed a good inhibition of M. tuberculosis, with a MIC of 252 μg/mL (Miran et al., 2020).

10.6 Applications of parsley, dill, and lovage essential oil 10.6.1 Pharmacological applications of parsley, dill, and lovage essential oil 10.6.1.1 Pharmacological applications of parsley essential oil The antioxidant properties of parsley essential oil could intercept the oxidative processes in the body, among which lipid peroxidation. These processes are usually linked to a series of pathologies such as atherosclerosis, diabetes, premature aging, and even cancer (Romeilah

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et al., 2010). Additionally, parsley essential oil and the major contained components could be a natural alternative to synthetic antioxidants (Zhang et al., 2006). Yousofi et al. (2012) studied the suppressive effect of parsley seeds essential oil on Balb/c mice splenocytes and macrophages proliferation and concluded that all tested concentrations (0.01–100 μg/mL) suppressed the cellular and humoral immune response, without showing any cytotoxic effect. This result showed that parsley seeds essential oil could be used as a natural treatment for a wide array of autoimmune pathologies and allergies. Additionally, several components of parsley essential oil were reported to stimulate the secretion of digestive juices, thus helping with the digestion processes (Punosˇevac et al., 2021). Eissa et al. (2012) assessed the effect of parsley essential oil as anti-diabetic and antihyperglycemic effect in vivo, on rats with induced diabetes. Albino rats were injected intraperitoneally with 50 mg/kg Streptozotocin (STZ) to induce diabetes mellitus. The rats treated with parsley essential oil had a decreased level of blood glucose and an increased insulin level. The treatment also determined a significant improvement in the lipid profile. However, a significant increase of reduced glutathione was reported in the blood of diabetic rats injected with parsley oil. These findings suggest a possible anti-peroxidative role derived from parsley essential oils. Abdellatief et al. (2017) assessed the protective effect of orally administered parsley essential oil against Cisplatin (cis-diamminedichloroplatinum, CDDP) induced hepatocardiotoxicity by intraperitoneal injection in male rats. The rats treated with CDDP presented hepatic and cardiac lesions confirmed by a series of alterations (biochemical, histopathological, and immunohistochemical) and an increase in the levels of specific biomarkers of heart and liver. The administration of parsley oil significantly improved the rate and severity of the reported damages produced by CDDP. It was concluded that parsley oil showed promising antioxidant, anti-inflammatory, and antiapoptotic properties, and that it might be useful in treating CDDP-induced hepatic and cardiac injuries. The hepatoprotective properties of parsley essential oil were reported by various studies. Abou Seif (2014) showed its efficiency in preventing oxidative stress together with its hepatoprotective properties against the hepatotoxic effect of alcohol. Khalil et al. (2015) reported that parsley leaves oil was effective in protecting the liver against the hepatotoxic damages caused by carbon tetrachloride (CCL4) in a rat model. The orally administered oil lowered the impact and severity of CCl4-induced biochemical alterations such as limiting the increase in triglycerides, cholesterol, liver lipid peroxidation malondialdehyde (MDA), superoxide dismutase (SOD), and glutathione (GSH). This hepatoprotective property was linked to the antioxidant activity of parsley essential oil, especially its free radical scavenging action. Similarly, El-Shall and Badr (2016) showed a significant hepatoprotective effect of parsley oil against cadmium chloride toxicity. While Mohammed and El Haliem (2013) assessed the effect of parsley essential oil on the chronic hepatotoxic effect of prednisolone in a rat model. They reported that parsley oil could improve the therapeutic efficiency of prednisolone while reducing its hepatotoxicity and established that the antioxidant properties of parsley essential oil are linked to this protective effect. Additionally, Mohammed and El Haliem (2013) showed that parsley essential oil protected the lungs against the toxic effects of prednisolone, using the same rat model. It was concluded that a higher dose and a longer treatment was needed to achieve a significant level of protection in lungs than for liver protection.

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Al-Ghamdi and AL-Amri (2016) examined the protective role of parsley essential oil against Etoricoxib drug (Arcoxia) on kidneys using albino rat fetuses as model. Histologic results showed that parsley essential oil prevented the toxic effects of Arcoxia which affects the structure and functions of kidney. The effect of parsley essential oils on genitourinary system was assessed by Abdel-Wahhab et al. (2006) who assessed the effect of zearalenone, a nonsteroidal estrogenic mycotoxin which induces testicular toxicity. They determined the testosterone level, sperm abnormalities and germ cells chromosomal analysis, and observed that parsley oil significantly increased the testosterone level, sperm count, and motility, but also inhibited chromosomal abnormalities. 10.6.1.2 Pharmacological applications of dill essential oil Dill essential oil was reported to have anti-inflammatory properties. Manzuoerh et al. (2019) reported that an ointment containing dill essential oil administrated topically was efficient in accelerating the healing of wounds infected with methicillin-resistant Staphylococcus aureus (MRSA). A BALB/c mice model was used, and the wounds were infected experimentally with MRSA isolated from burns. It was observed that the dill ointment inhibited the proliferation of bacteria and decreased the wound area by limiting the inflammation, but also accelerating the re-epithelialization process, angiogenesis, and the deposition of both fibroblast and collagen. Naseri et al. (2012) assessed the anti-inflammatory potential of dill essential oil administered alone or in combination with Diclofenac-gel on a rat model. The inflammation was experimentally induced by injecting formalin in the paws of male rats and the effect was determined by measuring the paw volume with a plethysmometer. The results showed a significant anti-inflammatory effect of the combined administration of dill essential oil and Diclofenac, but also that dill essential oil was more efficient than Diclofenac alone. The hypolipidemic activity of dill essential oil was reported by Hajhashemi and Abbasi (2008) on Wistar male rats fed with a hyperlipidemic diet. Doses of 45–180 mg/kg b.w./ day were administered for 2 weeks, and it was observed that dill essential oil reduced the levels of total cholesterol, triglycerides, and low-density lipoprotein cholesterol proportionally with the oil dose. Dill essential oil presents documented hepatoprotective properties as well. Rabeh et al. (2014) determined the effect of dill seeds oil against the hepatotoxicity of CCL4 in a rat model. The exposure to dill essential oil was oral, in a concentration of 1 mL/kg b.w. The oil inhibited the hepatotoxic effects of CCL4 by decreasing the levels of aspartate transaminase (AST) and alanine aminotransferase (ALT), while increasing the serum total protein and albumin levels. Additionally, dill essential oil inhibited the activity of alkaline phosphatase (ALP) and bilirubin which was increased by CCL4, thus stabilizing the CCL4-induced dysfunction of the bile. Abd El Monein Solaiman and Mahmoud Elagawany (2015) assessed the hepatoprotective effect of dill essential oil in a rat model exposed to 0.2% formaldehyde. They showed that an oral treatment with 1 mL/kg b.w. of dill oil helped reduce the formaldehydeinduced high hepatic transaminases’ levels. The effect of dill essential oil as anti-diabetic or antihyperglycemic was investigated on induced diabetic rats, by measuring the oxidative damage and antioxidant defense system. The results showed that dill essential oil caused a significant reduction in the levels of blood

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glucose, while significantly increasing insulin. The treatment also produced a significant improvement in the lipid profile. However, a significant increase of reduced glutathione was also detected. These findings suggest a possible anti-peroxidative role derived from dill essential oils (Eissa et al., 2012). Harries et al. (1977) demonstrated, in vitro, the mild antifoaming and carminative effect of dill essential oil by having a beneficial effect on the relieve feelings of discomfort and distension in the gastrointestinal tract. Dill essential oil was reported to help reduce intestine contractions in a rabbit model (Dhiman et al., 2017) and to have anti-bloating and anti-flatulence effect when administered to women after caesarean section (Fazel et al., 2017). The results of the study, which included 118 women, showed a 33% reduction compared to placebo in the intensity of flatulence 20 min after a 3rd dose of dill essential oil was administered. A significant decreased in the severe intestinal pain was also observed (10% for dill oils vs 3.5% for placebo). Additionally, no adverse effects were reported. The spasmogenic effect on smooth muscle of dill essential oil was also reported in vitro on a rat isolated phrenic nerve diaphragm (Lis-Balchin and Hart, 1997). 10.6.1.3 Pharmacological applications of lovage essential oil Several studies reported the main pharmacological properties of lovage essential oil: antibacterial activity (Ciocarlan et al., 2018; Mirjalili et al., 2010; Miran et al., 2020; Nevas et al., 2004; Semeniuc et al., 2017), antifungal activity (Ciocarlan et al., 2018) and antioxidant activity (Mohamadi et al., 2017) (Tables 10.4 and 10.5).

10.6.2 Food applications of parsley, dill, and lovage essential oil In recent years, as the reports of contaminated foodstuffs are increasing, essential oils could be a potential natural and environmentally friendly alternative to synthetic antioxidants and preservatives (Teneva et al., 2021). In Thailand, dill weed and seeds essential oils are used as a seasonings and flavoring agents for various types of foods (Ruangamnart et al., 2015; Chahal et al., 2017). Additionally, the food and beverage industry use essential oils as flavorings, an alternative to herbs and juices as they provide stronger flavor, thus, limiting the use of herbs (CBI, 2021a). Based on its antibacterial activity, Jianu et al. (2012) recommend dill flowers essential oil or its constituents as possible alternatives to natural antiseptics with applicability in the food industry. Kaur et al. (2021) showed that dill seeds essential oil can be used in pan bread to extend its shelf life because of its antifungal activity, but it also can improve its quality. Teneva et al. (2021) reported the possibility of using dill essential oil in combination with L. plantarum LBRZ12 in mayonnaise to reduce the alteration microflora to safe levels. Thus, the use of the two agents could become a hurdle technology for mayonnaise assuring food safety, but also good sensory properties throughout the shelf-life. Due to a good antibacterial activity, lovage essential oil ca be a low-cost natural antibiotic against the alteration and pathogen microflora (Mirjalili et al., 2010). It is able to inhibit the growth of bacteria, acting as a natural preservative, and thus extending the shelf life of food products. Lovage essential oil can be used in various foodstuffs in a wide range of concentrations, from 0.02 ppm added to hard candies up to 32.21 ppm used in alcoholic beverages

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(Venskutonis, 2016; Burdock, 2016). However, the usage of lovage essential oil is still limited because of its strong specific flavor. But more in-depth studies are needed that focus on its health-benefits in order to extend more broadly its uses in food industry. Thus, lovage can be considered a very promising herb for developing natural ingredients for the food industry (Venskutonis, 2016). On another note, smart and active packaging have become of high interest for the food industry, and the developing of antimicrobial packaging are a new focus for current research. The food-contact materials can benefit from the incorporation of essential oils such as dill, lovage, and parsley, because of their antioxidant and antibacterial properties (Tongnuanchan and Benjakul, 2014).

10.6.3 Non-food applications of parsley, dill, and lovage essential oil Parsley, dill, and lovage essential oils are widely used in aromatherapy products as natural remedies become increasingly popular (CBI, 2021a, 2018a). Based on this consumer trend, the cosmetic industry is increasingly creating products with aromatherapeutic properties by incorporating various types of essential oils (CBI, 2018a). Essential oils are used in creating fragrances in perfumery because they are a natural alternative to synthetic compounds. While the cosmetics industry uses essential oils in personal care products because they are a natural alternative to synthetic fragrances in product formulations (CBI, 2021a). Additionally, essential oils are used as active ingredients because of their calming, relaxing, and refreshing properties mainly in products such as skin care products (face, hand, and body lotions and creams), hair care products (shampoos and conditioners), bath salts, and even lipsticks and glosses (CBI, 2018a, 2021a). Thus, cosmetic products use herb oils both as main ingredients or as additives in moisturizing and cleansing lotions for the skin or shampoos and conditioners for the hair (Griggs, 2014). Among others, parsley essential oil is well known for its benefits as a basic ingredient in homemade skin care cosmetics (Griggs, 2014). It is also used in fragrances for men and hair products for dark hair or treatment of dandruff (Sarwar et al., 2019). The essential oil extracted from parsley was effective against the root-knot nematode (Meloidogyne incognita), Northern root knot nematode (Meloidogyne hapla), and peanut root knot nematode (Meloidogyne arenaria) (Seo et al., 2015). The most significant nematicidal activity was exhibited against M. incognita, with an EC50/72h value of 795  125 mg/L. Kong et al. (2006) tested the nematocidal activity parsley seeds essential oil against Bursaphelenchus xylophilus, however it showed little or no lethal activity. Similar, Lasioderma serricorne (Fabricius) seems to be immune to parsley leaf oil (Hori, 2003). Additionally, parsley essential oil is intensively studied for its benefits as insect repellent or as an insecticide agent (Kong et al., 2006; Kim et al., 2013a, b; Hori, 2003). Parsley seeds essential oil was an effective larvicide against the nymph of the citrus flatid planthopper, Metcalfa pruinose (Kim et al., 2013a, b). The results showed a 93% mortality of nymphs by direct contact when using 1000 mg/L for 24 h by leaf-dipping method, but only 17% when using 500 mg/L for 24 h. Massango et al. (2017) reported that parsley essential oil was able to control the bean weevil, Callosobruchus maculatus, being able to be more efficient than phosphine in reducing the emergence of C. maculatus. Additionally, a synergetic effect was observed when

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using parsley essential oil together with piperonyl butoxide, triphenyl phosphate, and diethyl maleate attributed to glutathione S-transferases which apparently increased the toxicity of parsley essential oil against C. maculatus. Parsley essential oil was also effective against the Asian tiger mosquito, Aedes albopictus showing a strong larvicidal activity, with above 90% mortality at 0.1 mg/mL, and 60% at 0.05 mg/mL (Seo et al., 2015). Similarly, Knio et al. (2008) evaluated the larvicidal activity of parsley seeds essential oil against the larvae of seaside mosquito, Ochlerotatus caspius. The oil exhibited strong larvicidal activity (LC50 of 34.3 ppm and 23.4 ppm after 24 h and 48 h respectively) against Oc. Caspius. The antifeedant, growth inhibitory, and insecticidal activities of parsley essential oil was assessed against the larvae of the true armyworm moth (Pseudaletia unipuncta) (Sousa et al., 2013). The oil was acutely toxic with feeding and growth indexes above 70%, and satisfactory toxic in the contact assay (>70%). These results suggest that parsley essential oil may be integrated into the control of several insect pests such as: the citrus flatid planthopper, Metcalfa pruinose, the bean weevil, Callosobruchus maculatus, the Asian tiger mosquito, Aedes albopictus, seaside mosquito, Ochlerotatus caspius, or Pseudaletia unipuncta. In another note, Bitire et al. (2021) investigated the potential production of biodiesel starting from parsley seeds essential oil by using catalytic potassium hydroxide (KOH). Biodiesel could be generated by the alcoholysis of parsley oil using KOH as catalytic at a 6:1 M ratio of ethanol to parsley seeds essential oil. Additionally, the fuel properties of parsley seeds oil were within the limits established by D6751 of the American Society for Testing and Materials (ASTM). Similar to parsley, dill essential oil extracted from seeds, leaves, and stems, are not only utilized as seasoning and flavoring agents for food production, but also in perfumery, and cosmetic industry as flavoring, but also sometimes as a cheaper substitute of caraway oil ( Jana and Shekhawat, 2010). Additionally, compounds of dill essential oil when added to insecticides increased the effectiveness of insecticides or can be used as insecticides ( Jana and Shekhawat, 2010). Kong et al. (2006) reported that dill weed essential oil showed little to no lethal activity against the nematode Bursaphelenchus xylophilus as determined by immersion bioassay. Dill essential oil possesses interesting properties that confer its documented insecticidal activity. Ebadollahi et al. (2012) assessed the insecticidal activity of dill essential oil against Callosobruchus maculates L. adults by fumigation. It exhibited a significant insecticidal activity with an LC50 value of 25.48 μL/L air. This suggested that dill essential oils could be used in the management of C. maculatus as an alternative to conventional insecticides. Dill seed essential oil was found to have insecticidal activity against Periplanata americana L., Musca domestica L., and Tribolium castaneum, as well, with mortalities varying from 25% to 100% after continuous exposure bioassays and fumigant toxicity bioassays (Babri et al., 2012). Khani and Basavand (2013) assessed its efficiency against 2 pantry pests: the confused flour beetle (Tribolium confusum Duval) and cowpea seed beetle (Callosobruchus maculates Fabricius) in a laboratory setting. The results of the fumigant toxicity assay showed that C. maculates (LC50 ¼ 0.54 μL/L air) was more sensitive to dill essential oil than T. confusum (LC50 ¼ 143.8 μL/L air) and considerable differences in the mortality of the two insects were observed at different concentrations and exposure times. The insecticidal potential and inhibition of acetylcholinesterase of dill essential oil was also reported against the rice weevil (Sitophilus oryzae) with a high

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fumigant toxicity (LC50 of 3.29 mg/L air) against adult insects (Kim et al., 2013b). Dill fruits essential oil was evaluated for its insecticidal action against the true armyworm moth (Pseudaletia unipuncta) (Sousa et al., 2013). The oil was acutely toxic by fumigation with a mortality above 80%, a feeding and growth indexes above 70%, and satisfactory toxic in the contact assay (>70%). Thus, dill oil was effective against P. unipuncta and could be used as repellent and/or insecticide (Sousa et al., 2013). Additionally, the larvicidal activity of dill essential oil and its components was reported against the larvae of Asian tiger mosquito, Aedes albopictus, with a reported mortality above 90% at 0.1 mg/mL (Seo et al., 2015). However, Kim et al. (2013a, b) observed no effect of dill essential oil against the nymph and adults of the citrus flatid planthopper, Metcalfa pruinosa. Seo et al. (2009) tested the antitermitic activity of dill seeds essential oil against the Japanese termites (Reticulitermes speratus Kolbe). The results showed a mortality of above 80% after 2 days when using a concentration of 2 mg/filter paper. Torki et al. (2018) assessed the effects of adding dill essential oil to the diets of laying hens that were exposed to heat stress in terms of biochemical parameters and their performance and egg quality. The dill oil intake decreased the serum cholesterol and triglycerides, with a significant effect on the egg index as well. This showed that dietary dill essential oil could improve some performance indexes of laying hens under heat stress. Lovage essential oils were frequently studied by many authors, but, most of the studies were aimed at identifying the chemical composition, antimicrobial, and biological activities and few studies were focused on its non-food applications (Venskutonis, 2016). Among others, lovage essential oil is well known for its benefits as a basic ingredient in homemade skin care cosmetics (Griggs, 2014). Kong et al. (2006) tested the effect of lovage root essential oil against the pine wood nematode (Bursaphelenchus xylophilus) and the results showed little or no lethal activity in an immersion bioassay. Most studies analyze its applicability as an insecticide or insect repellent (Hieu et al., 2010; Kim et al., 2013a, b; Halawa and Hustert, 2014). Lovage root essential oil together with tamanu oil (Calophyllum inophyllum L.) was reported to have repellent properties against the stable fly (Stomoxys calcitrans) in an exposed human hand assay (Hieu et al., 2010). The results based on the protection time showed that lovage essential oil displayed a repellence lasting for 3.36 h. Kim et al. (2013a, b) showed that lovage root displayed 100% mortality against nymphs of citrus flatid planthopper (Metcalfa pruinose) when using 1000 mg/L for 24 h by leaf-dipping method and 43% when treated with 500 mg/L for 24 h. This could reduce the level of highly toxic commercial insecticides, by using essential oils as alternatives. Halawa and Hustert (2014) tested the effect of lovage essential oil on migratory locus (Locusta migratoria (Linneus)) and observed a strong short-term neurotoxic effect in the central nervous system of the insect, and a subsequent moderate to long-term neural depression.

10.7 Safety and toxicity of parsley, dill, and lovage essential oil The toxicity of parsley essential oil is not well understood, however several in vivo and in vitro studies revealed its potential cytotoxic and beneficial effects, as seen in

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(Table 10.6). NIH (2021) reported no toxicity of parsley essential oil on rabbit or guinea pig skin at a dose over 5 g/kg. But an oral ingestion of a dose of 1520 mg/kg induced somnolence (general depressed activity), dyspnea, and a decreased urine volume in mice. In rats, an oral dose of 3300 mg/kg did not induce any adverse effect. However the studies cited by NIH (2021) are rather old and are not available on-line. The cytotoxic activity of parsley essential oil extracted by supercritical CO2 extraction was tested by cell metabolic activity MTT assay on RK 13 cell line (rabbit kidney) (Misic et al., 2020). The results showed no toxicity for concentrations up to 320 μg/mL. However, a weak cytotoxic effect was reported at 640 μg/mL, with a minimum value for the cell survival rate of 88%, while a concentration of 2560 μg/mL produced a survival rate of above 50%. Yousofi et al. (2012) reported no cytotoxic effect of parsley essential oil against splenocytes and macrophages of Balb/c mice. Dill essential oil and its components in certain doses can display cytotoxic effects (Table 10.6). NIH (2021) reported the acute oral toxicity of dill essential oil assessed by LD50 on a rat model to be 4040 mg/kg b.w, and 3000 mg/kg b.w. on a mouse model. The dermal toxicity was reported to be 5000 mg/kg b.w. on a rabbit model, while the subcutaneous LD50 was 1350 mg/kg b.w. on a mouse model. However the studies cited by NIH (2021) are rather old and are not available on-line. Even though dill essential oil is usually safe, rarely and in sporadic cases, it can cause allergic reactions, oral pruritus, swelling in the tongue and throat, urticaria, vomiting and diarrhea (Al-Snafi, 2014). Also, dill essential oil cand cause skin irritation (Mohsin et al., 2020). However, the average daily recommended dose of essential oil is 0.1–0.3 g (Al-Snafi, 2014). Dill root essential oil was reported to be more toxic than vincristine sulfate (standard anticancer drug) in a brine shrimp cytotoxicity assay, with an LC50 of 0.81 μg/mL (Saleh et al., 2017). This toxicity was attributed to apiol. However, it was further concluded that both dill root essential oil and dill apiol are potent antioxidant agents that can prevent lipid peroxidation, thus they could have a potential use in premature aging or cancer therapy (Saleh et al., 2017). Sharaf et al. (2009) investigated the genetic and reproductive toxicity of dill oil in male rats. The results showed that dill oil did not induce genotoxic effect in bone marrow cells. There were also no significant differences in testosterone level between the dill treated group and control. However mild disturbances, degeneration, and partial detachment of the spermatogenic cells and signs of abnormal division of spermatocyte cells was observed. Histochemical results showed significant decrease in total protein and DNA content of spermatogenic cells and spermatocytes, thus it could be concluded that due to the high estrogenic components, dill oil has some adverse effect on testicular tissue. Lazutka et al. (2001) evaluated the cytotoxicity and genotoxicity of dill weed and seeds essential oils combining in vitro chromosomes aberration and sister chromatid exchange tests in human lymphocytes with an in vivo somatic mutation and recombination test on Drosophilia melanogaster. Dill essential oils induced somatic mutations with a dose dependent response, dill herb at a concentration of 0.25% and 0.75%, and dill seed only at the highest dose of 1.50%. The oils were reported to produce mutations and induce cell and chromosome aberrations, and, thus, having a pregnant clastogenic effect and genotoxicity. (Lazutka et al., 2001). Al-Sheddi et al. (2019) explored the cytotoxicity of dill essential oil by cell metabolic activity MTT assay of human hepatocellular carcinoma cell line (HepG2 cells) and assessed cell cycle

TABLE 10.6 Potential cytotoxic and beneficial effects of parsley, dill, and lovage essential oils. Herb Parsley

Dill

Test type

Model (cell type/ animal)

Effect

References

In vitro

RK 13 (rabbit kidney) cell line

No cytotoxic effect

Misic et al. (2020)

In vivo

Splenocytes and macrophages of Balb/c mice

No cytotoxic effect

Yousofi et al. (2012)

Male mice

Increase of testosterone, sperm count and motility; decrease of chromosomal abnormalities

Abdel-Wahhab et al. (2006)

Male rats

Hepatoprotective effect

Khalil et al. (2015)

Albino rats

Ameliorate hepato-cardiotoxicity induced with Cisplatin

Abdellatief et al. (2017)

Male wister albino rats

Significant hepatoprotective effect against cadmium chloride toxicity

El-Shall and Badr (2016)

Albino rats fetuses

Decrease Arcoxia induced toxicity effect

Al-Ghamdi and AL-Amri (2016)

Adult male albino rats

Ameliorative effect against alcohol-induced hepatotoxicity and oxidative stress

Abou Seif (2014)

Adult male albino rats

Mild protective effect against prednisoloneinduced liver and lung injury

Mohammed and El Haliem (2013)

Male albino Sprague Dawley rats

Anti-diabetic and antihyperglycemic effect

Eissa et al. (2012)

Human caucasian colon adenocarcinoma cell line LS180 (ECACC No. 87021202), Human 155 caucasian hepatocellular carcinoma cells HepG2 (ECACC No. 85011430), human cervix; 156 epitheloid carcinoma cells HeLa (ECACC No. 93021013), human prostate carcinoma 157 epithelial cells 22Rv1 (ECACC No. 105092802)

Mixed anti-glucocorticoid and VDRstimulatory activities; the toxicological significance is very low, may be considered safe

Bartonkova and Dvorak (2018)

Human lymphocytes

Pregnant clastogenic effect and genotoxicity; inhibited cell replicative kinetics

Eissa et al. (2012)

Bone marrow micro-nucleated polychromatic erythrocytes (MNPCEs)

No genotoxic effect

Lis-Balchin and Hart (1997)

Human hepatocellular carcinoma (HepG2 cells)

Anticancer potential against hepatocellular carcinoma

Al-Sheddi et al. (2019)

Liver cancer cell lines (HepG2), human umbilical vein endothelial cells (HUVECs)

A higher cytotoxicity against cancer cells than normal cells

Tavakkol et al. (2019)

In vitro

In vivo

Lovage

In vitro

In vivo

Drosophilia melanogaster

Induced somatic mutations

Lazutka et al. (2001)

Albino male rats

Mild testicular damage

Sharaf et al. (2009)

Male rats

Anti-inflammatory effect

Naseri et al. (2012)

Wistar male rats

Hypolipidemic effect

Hajhashemi and Abbasi (2008)

Male Sprague Dawley rats

Hepatoprotective effect

Rabeh et al. (2014)

Male albino rats

Hepatoprotective effect against 0.2% formaldehyde induced hepatotoxicity

Abd El Monein Solaiman and Mahmoud Elagawany (2015)

BALB/c male mice

Accelerating healing of MRSA infected wounds

Manzuoerh et al. (2019)

Women

Treatment of post C-section flatulence and abdominal pain

Fazel et al. (2017)

UMSCC1 cells derived from T2N0M0 squamous cell carcinoma

Cytotoxic effect with a IC50 value at 292.6 μg/mL

Sertel et al. (2011)

Salmonella strains

No mutagenicity or cytotoxicity activity

Coggins et al. (2011)

Human caucasian colon adenocarcinoma cell line LS180 (ECACC No. 87021202), human 155 caucasian hepatocellular carcinoma cells HepG2 (ECACC No. 85011430), human cervix 156 epithelioid carcinoma cells HeLa (ECACC No. 93021013), human prostate carcinoma 157 epithelial cells 22Rv1 (ECACC No. 105092802)

Mixed anti-glucocorticoid and VDRstimulatory activities; the toxicological significance is very low, may be considered safe

Bartonkova and Dvorak (2018)

Woman

Contact dermatitis

Lapeere et al. (2013)

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10. Essential oils from Apiaceae family (parsley, lovage, and dill)

arrest and apoptosis. The cytotoxicity results showed a dose-dependent decrease in the viability of HepG2 cells, with an IC50 of 59.6  5.64 mg/mL. Thus, dill essential oil could be a potential antiproliferative and anticancer agent against human hepatocellular carcinoma cells. A dill essential oil nanoemulsions displayed a dose-dependent toxic effect on 2 tested cell lines: HepG2 (liver cancer) and HUVECs (human umbilical vein endothelial cells) (Tavakkol et al., 2019). A higher effect was observed against HepG2, thus, the cytotoxicity was higher toward the cancer cells than normal cells. The activity of dill fruits essential oil as endocrine disruptor was assessed based on the transcriptional activities of glucocorticoid receptor, androgen receptor, and vitamin D receptor (VDR) (Bartonkova and Dvorak, 2018). The results showed that the oil exhibited mixed effects on the anti-glucocorticoid and VDR-stimulatory properties, thus, a very low endocrine toxicity. According to EC 1272/2008 guidelines dill essential oil was classified in hazard category 2 as skin corrosion irritation, hazard category 1 as skin sensitizer, and category 3 as aspiration hazard. Additionally, it is considered a hazardous substance to the aquatic environment and categories as category 1 long term chronic hazard. Lovage essential oil is less studied compared to other plants, but some of its main toxic and beneficial effects are described in Table 10.6. NIH (2021) reported the oral toxicity of lovage essential oil assessed by LD50 on a mouse model to be 3400 mg/kg b.w. based on rather old studies. The cytotoxicity of lovage leaf essential oil was tested against the head and neck squamous carcinoma cells (HNSCC) by the cell proliferation (XTT) assay with an IC50 value of 292.6 μg/ mL (Sertel et al., 2011). Additionally, the microarray hybridization analyses showed that lovage essential oil affected mainly the genes involved in apoptosis, cellular growth, and cell cycle regulation. Coggins et al. (2011) assessed the toxicology of lovage root oils added to experimental cigarettes. The smoke from the experimental cigarette was evaluated using analytical chemistry and in vitro bacterial (Salmonella) mutagenicity and cytotoxicity assays. The results showed no increases in bacterial mutagenicity under any of the conditions of the test. The activity of lovage essential oils as endocrine disruptor was assessed similarly to dill essential oil on the transcriptional activities of glucocorticoid receptor, androgen receptor, and vitamin D receptor (Bartonkova and Dvorak, 2018). The results showed that the oil was inactive against all the tested receptors, thus, having a very low endocrine toxicity. Lapeere et al. (2013) reported that lovage essential oil caused contact dermatitis in a 31-year-old woman. The lesions were clearly demarcated, exhibiting abnormal redness with scaling. A patch test reaction confirmed that lovage essential oil was responsible. Thus, lovage essential oil might cause skin irritation due to contact dermatitis.

10.8 Trade and regulation of parsley, dill, and lovage essential oil The demand for essential oils world-wide was evaluated at about 247.08 kt in 2020, and market specialists expect it to have an annual increase of 7.5% from 2020 to 2027 (GVR, 2020). The main distribution channel was direct selling (70% in 2019) and multi-level marketing selling practiced by players like doTerra and Young Living Essential Oils (GVR, 2020).

10.8 Trade and regulation of parsley, dill, and lovage essential oil

299

The world leader in the demand of essential oils is Europe (GVR, 2020; CBI, 2018a, 2021b) with a volume share of 43.65% in 2019. The European market is expected to reach $12.9 billion 2023, and the demand to increase annually by 8.7% to 11.7% (CBI, 2018a). This increase is expected to be attributed mainly to food and beverage industry, cosmetics and health care, and aromatherapy (GVR, 2020). The food and beverage industries were the major consumers of essential oils with a volume share of 38.6% in 2019 because of the increasing desire for natural, safe, and minimally processed foods. Another driver for the increasing demand for essential oils is the salt reduction tendency and the increase appetite for ethnic foods (CBI, 2018b). On the European market, the essential oils intended for food industry must be 100% pure and natural. When essential oils are mixed together the mixture must be labeled as a blend of essential oils, while when it is diluted with solvents (i.e. propylene glycol) it must be labeled as flavor (CBI, 2018b). About a third of the market is formed by fragrances, cosmetics, and aromatherapy industries (CBI, 2021b). Another growing market in Europe is that of the natural and organic cosmetics, valued at EUR 3.64 billion in 2018 because consumers are increasingly forming a robust demand for natural ingredients (CBI, 2021b). Apart from Europe, the aromatherapy segment is growing strongly in the U.S., while emerging markets are appearing in Asia and Latin America (CBI, 2018b). The market of niche essential oils is on the rise (CBI, 2021b). Parsley, dill, and lovage essential oil are among the 150 essential oils that can be found on the European market, and they can be considered niche essential oils (CBI, 2018b). Douglas et al. (2005) reported the traded quantities and market value of some essential oils among which parsley, dill, and lovage (data pre-1993). Dill weed had the largest traded quantity (114 t), followed by dill seed (23 t), parsley seed (8 t), parsley herb (4 t), lovage root and herb (both at 2 t), and lovage seed (0.9). However, lovage root essential oil had the highest value market, being the most expensive of the seven types ($800.000/t), followed by parsley seed oil ($140.000/t) and dill weed oil, which was the cheapest of the 7 ($7.000/t), but was traded in much higher quantities. More recently, Brud (2020) approximated based on production volume that dill essential oil was used between 100 and 500 t per year world-wide, but the consumption could be higher as no data on the domestic consumption are available for major producers such as China, India, Indonesia, and South America. India is the main producer and exporter of dill seed essential oil, and the main markets are Europe, the Americas, Middle East, and Africa because of the health-related attributes of dill essential oil (GMI, 2019). It was reported that the market of dill seed essential oil was estimated at $1.5 billion in 2018 and that the demand was expected to grow at 82,500 t by 2025 (GMI, 2019). In Asia and Pacific region an increase of 4% by 2025 is forecasted, while in Europe dill seed essential oil market is expected to exceed $100 million by 2025. This increase is attributed to flavor, fragrance, and pharmaceutical industries, especially in skincare and skin-related pathologies (GMI, 2019). The use of dill seed essential oil in fragrance industry is forecast to increase with 3.5% by 2025, reaching $308.5 million, because of its characteristic scent, which is light, fresh, warm, spicy, similar to spearmint and caraway, but with softer notes. Dill seeds essential oil is used in skincare products because it promotes quick healing and maintains skin structural integrity, thus it is used in anti-aging products and sunscreen. The market value of dill seeds essential oil used in skincare industry is expected to increase with 2.5% by 2025, exceeding $190 billion.

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The use of dill seeds essential oil in packaged foods is also expected to increase, especially in product such as soups, pickles, salads, fish, sandwich fillings, and sauces (GMI, 2019). Additionally, its use as a pest-control substance which will also influence the rise in the demand. No recent data on the market value of lovage essential oil are available, but in terms of lovage extract, the market is expected to grow in size significantly in the period 2021–2027 (GMI, 2021), especially because of the lovage root extract increased popularity among the healthconscious consumers. Additionally, lovage essential oil has wide applications in soaps and cosmetics, but also in cuisine as it can add an intense flavoring to pork, poultry, and potato dishes, but also stews and soups, in an effort to reduce salt intake. Recently, Knorr marketed the Zero Salt Bouillon cube which is obtained from vegetables, herbs and spices, including lovage. ISO provide the standards for oil of roots of lovage ISO 11019:1998 and essential oil of parsley fruits ISO 3527:2016 which specify the physical and chemical properties of these oils. ISO/ TS 210:2014(E) states the general rules for packaging essential oils for commercial purpose and recommends the use inert containers (i.e. glass, lacquered or lined steel, aluminum), the use of inert gases (i.e. N or CO2) in the headspace to avoid oxidation, and the storage in dark, dry, cool places. ISO/TS 211:2014(E), on the other hand, states the general rules for labeling. In Europe several essential oils are classified as hazardous substances, including parsley, dill, lovage (CBI, 2018b) and they must abide by the Regulation EC 1272/2008 on classification, labeling, and packaging of chemicals. Thus, the following must be included on the label: relevant safety phrases, risk phrases, and hazard symbols. Additionally, the flammability, risk and safety phrase must be stated according to the Directive 2001/59/EC on the classification, packaging, and labeling of dangerous substances. The commercially available parsley essential oil (Oils4life, Limited, 2021) was characterized according to EC 1272/2008 as follows: flammable liquid (category 3), can cause acute toxicity by oral ingestion (category 5), skin corrosion, skin irritation, serious eye damage and eye irritations (category 2), causing skin sensitization, and aspiration hazard (category 1), hazardous to the aquatic environment, (category 2), and long-term hazard. The commercially available parsley seeds essential oil (Oils4life 2021) was characterized according to EC 1272/2008 as follows: flammable liquid (category 3), can cause acute toxicity by oral ingestion (category 5), skin corrosion, skin irritation, serious eye damage and eye irritations (category 2), causing skin sensitization, and aspiration hazard (category 1), hazardous to the aquatic environment (category 2), and long-term hazard. Similarly, commercially available dill seeds essential oil (Oils4life 2021) is classified according to EC 1272/2008 as: skin corrosive (category 2), skin sensitizer hazard (category 1), aspiration hazard (category 3), hazardous to the aquatic environment, (category 1).

10.9 Conclusion Parsley (Petroselinum crispum Mill), dill (Anethum graveolens L.), and lovage (Levisticum officinale KOCH.) essential oils can be obtained from various organs of the herbs: roots, arial parts (sometimes called weed), leaves, flowers, seeds (also known as fruits), by different

10.9 Conclusion

301

extraction techniques (hydrodistillation, supercritical fluid extraction, simultaneous steam distillation and extraction, or solvent extraction). The chemical profile of the obtained essential oil varies greatly, especially since agronomic factors have a significant influence upon the essential oil yield and the proportion of various components. Among the agronomic factors, the most studied factors for parsley, dill, and lovage seem to be the developmental stage of the herb (eight studies), followed by fertilization (six studies), and salinity (five studies), while the growing area is the most understudied factor. Usually, the highest yield is obtained from seeds (up to 9.3% for parsley seeds), while the lowest yield is obtained from leaves and roots (as low as 0.02% for hairy dill roots). Usually, hydrodistillation is the go-to extraction methods, but novel extraction procedures like ultrasound-assisted extractions, supercritical fluid extraction are gaining interest. However, all extraction methods have specific disadvantages: supercritical fluid extraction is efficient, but expensive, which limits its industrial application; hydrodistillation employs heat that can affect the monoterpenes in the essential oil; and solvent extractions pose the risk of volatile compounds evaporation during the procedure. Thus, there is no golden standard extraction procedure, especially when the essential oil yield and chemical profile can vary greatly dependent on a wide range of factors. Of the three herbs, dill is the most studied in terms of essential oil production, followed by parsley, and lovage, which is a rather underutilized herb with a very high potential. The major compounds identified in parsley essential oil obtained by hydrodistillation usually are monoterpenes such as: β-phellandrene; 1,3,8-p-menthatriene; apiol; β-myrcene; α-pinene. Dill, on the other hand is considered to have four chemotypes characterized by the presence of (1) myristicin; (2) dill apiole; (3) myristicin and dill apiole; (4) neither myristicin nor dill apiole. Lovage essential oils are dominated by terpenes and phthalides. In terms of bioactivity, the essential oils of parsley, dill, and lovage have shown good antioxidant activity due to their chemical structure, but also antibacterial and antifungal properties. All three essential oil have also insect repellent properties. Additionally, several pharmacological properties of these essential oils or extracted compounds were reported in vitro or in vivo by various studies such as antiviral, anti-diabetic, hepatoprotective, gastroprotective, immunomodulating, and protective effect over kidney toxicity. However, the toxicity of parsley, dill, and lovage essential oil has not been thoroughly investigated and further studies are needed in this respect. The European Union considers essential oils as hazardous substances, and they must abide by the Regulation EC 1272/2008. However, parsley, dill, and lovage essential oils are increasingly used in the food industry as flavoring agents, but also as alternatives to synthetic preservatives, in cosmetics industry and aromatherapy, but also as natural insect repellents and pest management substances. Moreover, they are considered niche essential oils, and their market is seeing a significant increase. Further studies are needed to precisely establish the toxicological profile of parsley, dill, and lovage essential oils prior to establishing their possible industrial or pharmacological use. Of the three herds, lovage essential oil is very little studied, although it has very promising results in terms of its bioactivity. Additionally, little information is available on the market value and volume of parsley and lovage essentials oil because all niche essential oils are usually reported together in trade reports.

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10. Essential oils from Apiaceae family (parsley, lovage, and dill)

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C H A P T E R

11 Essential oils from Lamiaceae family (rosemary, thyme, mint, basil) Sumeyye Inanoglua, Gulden Goksenb, Gulzar Ahmad Nayikc, and Amir Sasan Mozaffari Nejadd a

Department of Food Science, Rutgers, The State University of New Jersey, New Brunswick, NJ, United States bDepartment of Food Technology, Vocational School of Technical Sciences at Mersin Tarsus Organized Industrial Zone, Tarsus University, Mersin, Turkey cDepartment of Food Science & Technology, Government Degree College Shopian, Srinagar, Jammu & Kashmir, India dSchool of Medicine, Jiroft University of Medical Sciences, Jiroft, Iran

11.1 Chemical composition of essential oils Essential oils (EOs) are complex mixtures containing several different molecules, the majority of which are polymolecular in nature, and contain between 20 and 60 components in a wide range of concentrations. These are characterized by the presence of up to three main components at relatively high concentrations (20%–70%) in comparison to the presence of other compounds in trace levels. For example, thymol (27%) and carvacrol (30%) are the primary components of the Origanum compactum EO, camphor (24%), and α- and β-thujone (57%) of the Artemisia herba-alba EO, linalool (68%) of the Coriandrum sativum EO, 1,8-cineole (50%) of the Cinnamomum camphora EO, limonene (31%) and a-phellandrene (36%) of leaf and limonene (37%) and carvone (58%) of seed Anethum graveolens EO, menthone (19%) and menthol (59%) of Mentha piperita EO. In general, these main constituents decide the EOs biological properties. Analysis of EO shows that certain essences are made up of a predominant component alongside a dozen other minorities. Others, on the other hand, are particularly complex and may contain more than a hundred compounds. We can give as an example in the first case, the clove (Eugenia caryophyllata) essential oil, which contains 80% eugenol, 10% β-caryophyllene, and small amounts of 10 other products; in the second case, let us cite as an example, vetiver essence (Vetiver/nigritana) which contains 160 constituents, the most abundant of which does not exceed 8%. Based on their metabolic origin, the components

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are separated into two groups (Bakkali et al., 2008; Croteau et al., 2000; Pichersky et al., 2006). The primary group consists of terpenes and terpenoids, while the other group consists of aliphatic and aromatic constituents, all of which have a low molecular weight.

11.2 Lamiaceae family Lamiaceae is a significant family for the synthesis of EO with antimicrobial (AM) and antioxidants (AO) properties. EOs are abundant in aromatic plants, which are mostly located in the Mediterranean region, where their oil production is a rich source of economic and ecological progress. The use of antioxidant and antimicrobial containing EOs to extend the food shelf life is a viable technology, and the EO of thyme, basil, and rosemary have been intensively examined for their potential use as food preservatives. The most frequently used plants in traditional treatments are rosemary, thyme, mint, and basil for the curing of dermatitis, infections, bronchitis, inflammation, and gastritis. Rosemary and sage, in particular, have been widely studied for their antioxidative and antibacterial properties. (Nieto, 2017). Lamiaceae is Angiosperms’ sixth largest family, with 12 subfamilies, 16 tribes, 9 subtribes, 236 genera, and about 7000 species (Frezza et al., 2019) more or less cosmopolitan species. Because a large portion of these plants is aromatic and high in essential oils, they are valued for their economic and medicinal value. Lamiaceae is a family of plants that can be found all over the world.

11.2.1 Essential oil of Lamiaceae family The volatile sesquiterpenes, monoterpenes, and diterpenes, which have 15, 10, and 20 carbon atoms, respectively, are abundant in the EO of Lamiaceae species. The b-pinene, a-pinene, 1,8-cineole, menthol, g-terpinene, and limonene are the most common monoterpenes (Bozin et al., 2007; Carovi
c-Stanko et al., 2010; Panizzi et al., 1993). Indeed, the primary sesquiterpene compounds are germacrene D, spathulenol, and caryophyllene (Daferera et al., 2000; Mohagheghzadeh et al., 2000). Additionally, the EO of the Lamiaceae species contains fatty acids (Taarit et al., 2010). These can be found in their natural state or combined in the form of triglycerides and diglycerides. Furthermore, its structure may contain medium (C14 and C16) or long (C18) chains and even double and single in saturations.

11.3 Composition of basil, mint, rosemary, and thyme oil Rosmarinus officinalis L. is a member of the Rosmarinus genus, which belongs to the Lamiaceae family. The main terpenoids composing rosemary oil are 1,8-Cineole, α-Pinene, and Camphene. The antioxidant effect of rosemary essential oil comes from phenolic compounds in the group of flavonoids and tocopherols including rosmanol, carnosic acid, rosmadiphenol, carnosol, 1,8-cineol, and rosmarinic acid. The components of carvone, carvacrol, eugenol, thymol, and cinnamaldehyde in rosemary oil can enhance microbial activation (Rasˇkovi
c et al., 2014).

11.3 Composition of basil, mint, rosemary, and thyme oil

311

Thyme oils are an essential oil obtained from Thyme (Thymus vulgaris L.), which is under the category of the Lamiaceae family. The genus Thymus is a well-known plant over the world, and its major components can be represented in four groups phenolic acids (rosmarinic acid, caffeic acid, gallic acid), phenolic diterpenes, volatile compounds (thymol), and flavonoids (Shan et al., 2005). Ocimum basilicum L. is one of the members of Ocimum genus, known as basil, which is considered the most cultivated aromatic herb. Basil oil is a mixture of sesquiterpenes, monoterpenes, and phenols. Major components from basil are phenol derivatives—eugenol, methyl chavicol, and linalool. Basil leaves also contain flavonoids such as isoquercetin, quercetin, rutin, caffeic acid, and esculin (Dhar, 2002). The major types of phenolic compounds of sweet basil are phenolic acids (caffeoyl derivatives, rosmarinic acid), carvacrol, phenolic diterpenes, and catechin (Shan et al., 2005). The AO properties of EOs are dependent on the monoterpenes including α-Terpineol, camphor, pinene, thymol, 1,8-Cineole, limonene, and carvacrol. Thyme and bush-basil consist of higher concentrations of antioxidant terpenes, especially thymol and carvacrol. Therefore, thyme and bush-basil essential oils show better antioxidant effects compared to other essential oils such as rosemary (Alsaraf et al., 2020). Mints are classified within the genus Mentha belonging to the Lamiaceae family. Phenolic acids such as rosmarinic acid, caffeic acid, flavonoids, and volatile compounds (menthol) are representative components for mint (Mentha canadensis L.) (Shan et al., 2005). The components of mint oil, which are derived from aerial parts of the herb, are linalyl acetate menthol, carvone, linalool, menthone, menthofuran, and isomenthone (Verma et al., 2010). The main compounds are phenolic acids (rosmarinic acid, caffeic acid), menthol, and flavonoids (Shan et al., 2005). Table 11.1 represents some major components of thyme, rosemary, peppermint, and basil. The chemical makeup of essential oils determines their biological and functional properties. These natural aromatic oils are a mixture of several compounds (20–60) such as ketones, terpenoids, aldehydes, lactones, esters, terpenes, alcohols, and other organic substances at different concentrations. Two or three compounds share a higher percentage in the total content, and therefore the properties of essential oils depend on these major compounds while the remaining part consists of other metabolites with trace amounts. The antimicrobial effects of EOs are highly dependent on phenolic compounds such as carvacrol, thymol, and eugenol. Not only significant components displayed antibacterial activity, but also minor components, possibly as a result of a synergistic impact among other components, which was found in certain species of Thymus (Burt, 2004). Large amounts of essential oils are produced from raw materials obtained from plants or plants organs such as seeds, flowers, buds, fruits, and leaves. Several methods including fermentation, enfleurage, expression, or extraction can be applied to plants to obtain essential oils. Steam distillation has been widely accepted as a process for commercial essential oils production. Steam and hydrodistillation extraction method, which requires high temperature, might cause chemical alterations in all compositions of EOs since EOs are volatile and sensitive to temperature. Therefore, supercritical fluids, particularly carbon dioxide was used to mitigate this problem (Eslahi et al., 2017). In this regard, most often aroma profiles are still intact after extraction, and therefore the method of supercritical extraction is often used in the fragrance and flavor industry. This method is only used in the food industry when there is no risk of any harmful residue left in food products (Kubeczka, 2020).

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TABLE 11.1 Some major components of thyme, rosemary, peppermint, and basil. Family and scientific

Common name

Thymus vulgaris L.

Thyme

Thymol Carvacrol γ-Terpinene β-Cymene

Eslahi et al. (2017)

Rosmarinus officinalis L.

Rosemary

α-pinene Bornyl acetate Camphor 1,8-cineole

Eslahi et al. (2017)

Mentha piperita L.

Peppermint

Menthol ρ-menthone Isomenthyl acetate

Aziz and Craker (2010)

Representative picture

Major components

Reference

313

11.4 Extraction techniques

TABLE 11.1

Some major components of thyme, rosemary, peppermint, and basil—cont’d

Family and scientific

Common name

Ocimum basilicum L.

Basil

Representative picture

Major components Linalool Methyl chavicol Eugenol

Reference Simon et al. (1990)

11.4 Extraction techniques Although the modern-day equipment has made the extraction of essential oils easier than in the previous century, the researchers still use some modified versions of steam distillation (SD), hydro-distillation (HD), distillation by a modified Clevenger, supercritical CO2 method, and microwave-assisted hydro-distillation method followed by Gas chromatography (GC) and Gas chromatography-mass spectrometry (GC-MS) for analysis and quantification (Boutekedjiret et al., 2003; Lo Presti et al., 2005; Masango, 2005). In the steam distillation (SD) method, a glass column is among the major requirement of the process. The aerial parts of the plants can be placed inside the glass column. The upper part of the glass column is connected to a condenser while the lower part is connected to a waster flask. When the system is subjected to heat, water vapor starts to form within the flask and becomes charged with essential oils present in the sample before moving to the condenser. After the condensation process is over, the essential oil is extracted from the water-oil mixture by decantation. EOs from rosemary, mint, thyme and basil can also be extracted by the hydro-distillation process. It can be carried out in the same ambient conditions as prescribed for the steam distillation method. The major difference between SD and HD occurs in the case that, in the HD process, the aerial parts of the rosemary plant are placed in the water flask and allowed to boil. This water-oil mixture produced in the flask was then passed on to the condenser fitted above the water flask. After the condensation process was over, the essential oil is recovered through decantation. The distillation by a modified Clevenger method is a universally used method for extraction of EOs from aromatic plants including Rosemary, Thyme, Mint, and Basil. Fresh leaves of 150 g were kept in the Clevenger and the distillation unit was run for 1 h using three liters of water. The entire system was made to attain a boiling point by heating it at a fixed power of 800 W in the atmospheric pressure. An internal thermometer is adjusted to the system to monitor the temperature. The reflux of condensed water through a circulating cooling system

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maintained a constant and stable water quality. The separation of essential oils from the water mixture was done by a decantation system associated with the modified Clevenger. The supercritical CO2 method is a popular method for the extraction of EOs from aromatic plants since it is a relatively easy process under standard operating conditions. Modern extractors such as SFE LAB 0.2 are perfect for this method of essential oil extraction. Fresh leaves of 50 g are needed to be placed in the compartments of the extractors. The volatile fractions present in the plant materials were completely extracted at 60°C and 250 atm pressure at a 5 mL/min fluid rate for 30 min through supercritical CO2. Since the advancement in microwave technologies, researchers are always tempted to utilize it in oil extraction procedures and the Microwave-assisted hydro-distillation method was one of the major examples of this temptation (Lucchesi et al., 2004). A PTFE coated “Dry Dist” microwave reactor with cavity dimensions of 35
35
35cm is perfect for this extraction. Although the distillation process was carried out at atmospheric pressure, the temperature was needed to be fixed through a power supply of 900 W. An external infra-red sensor was employed to monitor the temperature. A circulating cooling system responsible for refluxing condensed water was fixed to the system to ensure constant temperature and water quality. Fresh plant leaves of 150 g weight are needed to be placed in a 0.8 L water bath for up to 20min before placing it into the reactor. Complete distillation of EO can be obtained in 18 min through this method. The essential oils extracted through these methods can be quantified and analyzed by GC and GC-MS (Boutekedjiret et al., 1997). A column is a prerequisite needed to be fitted properly for GC and GC-MS analysis. The column is generally a capillary column made up of silicacoated with a 1.5 μm film of polydimethylsiloxane (DBP-1). The ambient temperature of the column was decided to be started at 60°C and slowly increase up to 200°C at a rate of 3°C per minute. Nitrogen and Helium at 1 mL/minute were used as a carrier gas for GC and GC-MS respectively. The essential oil produced was although collected at regular intervals and analyzed through GC to keep a track of the composition and yield of EOs. The estimation of EO components present in the plant samples was done according to the production of dry vegetal matter applying the following formula: R% ¼

m
100 s

where R ¼ yield of EO in percentage m ¼ mass of EO in gram s ¼ mass of dry vegetal matter in gram.

11.5 Safety, toxicity, and regulation of basil, mint, rosemary, and thyme oil EOs have been utilized to enhance the functionalities of medications, cosmetics, and foods without jeopardizing their safety. Recent years have seen a surge in interest in the production of EOs, owing to the growing consumer desire for natural products. Although the vast majority of EOs are GRAS (generally regarded as safe), analyzing their composition has become more significant. As a result, the essential oils are characterized chemically and toxicologically. According to Dima and Dima (2015), concepts such as “the principle of self-limitation”

11.5 Safety, toxicity, and regulation of basil, mint, rosemary, and thyme oil

315

and “the long history of safe usage” are utilized for consumption of essential oils as “safe under normal conditions of use.” Various international organizations such as the FDA (Food and Drug Administration), IOFI (the International Organization of Flavor Industries), FEMA Manufacturers Association, FCC (Food Chemical Codex), Codex Alimentarium, and the CoE (Council of Europe), have developed and approved specific protocols for toxicological and chemical analyses, as well as processing guidelines. Additionally, these procedures incorporate safety constraints regarding the volatile component composition of essential oils (Dima and Dima, 2015). The FDA decided that 160 essential oils including rosemary, thyme, spearmint oils are GRAS to use in food preparation, cosmetics, and drugs (Baker and Grant, 2018; Tisserand and Young, 2013). Mint and mint oils are exempt from the requirement of a tolerance under 40 CFR 180.950(a). According to U.S. Environmental Protection Agency (EPA), corn mint oil is permitted for food use, whereas in FDA requirements, corn mint is not accepted as GRAS in 21 CFR 182 (Baker and Grant, 2018). Even though these oils are recognized as GRAS, their appropriate dose should be determined by toxicity/safety studies since all essential oils could be toxic at very high doses, particularly when consumed orally (Burfield, 2000). Each essential oil should be validated in terms of its safety limit before its usage as a food preservative since some essential oils have possible cancer-causing effects (McGuffin et al., 1997). Excessive use of essential oils in animals and possibly in humans may result in functional harm to organs such as the stomach and liver (Ngahang Kamte et al., 2018). While there are numerous toxicity/safety tests available, one of the most frequently used is the acute toxicity test, which allows for the estimate of the median fatal dose (LD50), which is the dose at which 50% of the tested population died (Dahham et al., 2016; Falleh et al., 2020). The higher LD50 value of EO presents stronger suitability as a food preservative (Falleh et al., 2020). According to Tisserand and Young (2013), the EO of thyme is not considered toxic unless ingested orally. However, thyme is not recommended to use by pregnant women due to its chemotype. The most toxic one is the red thyme chemotypes, which contain phenols (Veal, 1996). Chemotypes of thymol and/or carvacrol are the compounds in the majority of thyme oils and can be moderately irritant. The compounds of thymol, menthol, and eugenol may irritate mouth tissues when applied in root canal treatments (Burt, 2004). The toxicity of some essential oils may change significantly depending on chemotypes (Young and Williamson, 2014). Lee et al. (2001) studied the toxicity of EOs and reported that the primary component of rosemary, 1,8-cineole, was the major toxic compound. Ben Abada et al. (2020) reported that 1,8-cineole/camphor/α-pinene is the predominant rosemary chemotype. The EOs of 156 other aromatic plants including thyme and rosemary were recognized as safe under the regulatory limitations by the Code of Federal Regulations Title 21 (Falleh et al., 2020). Several EOs are toxic to a wide range of insect pests. The potent toxicity of essential oils can be utilized as an alternate to fumigant, insecticidal, antifeedant against agriculture and storage food insects due to their volatility in nature. The primary chemical ingredients of insecticidal essential oils are monoterpenes. Carvacrol (T. vulgaris) and thymol can cause convulsions in insects when consumed or administered topically. Essential oils from R. officinalis, T. vulgaris are well-known due to their varied properties of pest control. In comparison to synthetic insecticides, these essential oils are considered environmentally safe pesticides and insecticides since they do not have non-toxic residues in the treated products (Kuttan and Liju, 2017).

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11. Essential oils from Lamiaceae family

Most people are unaware of EOs compounds that are irritating, allergic, or cause toxic reactions. As a result, worldwide authorities are requiring new precautions for the ingestion of essential oils due to their unpleasant effects, which can be unpredictable in the majority of cases (Do et al., 2015). In this regard, regulations play an important role to control the use of EOs and prevent their possible adverse effects. Global institutions including the WHO (World Health Organization), FAO (Food and Agriculture Organization of the United Nations), FAO/WHO CAC (Codex Alimentarius Commission), ISO (International Organisation for Standardisation), FDA, and EU commission has been working diligently to ensure the safety of EOs. These organizations’ tactics and policies had a favorable effect on the global safety of these compounds. Still, each nation should consider another control mechanism at the national level for a specific consumer society (Hashemi et al., 2017).

11.6 Storage stability of basil, mint, thyme, and rosemary oil Lipophilic and highly volatile components of essential oils are susceptible to conversion reactions such as isomerization, oxidation, polymerization (Turek and Stintzing, 2011). Many essential oils are easily affected by physicochemical factors such as light, pH, oxygen, and temperature during storage, transport, and processing. Therefore, microencapsulation is applied to essential oils to preserve their flavor and extend their shelf lives (Dima and Dima, 2015). Alikhani-Koupaei et al. (2014) compared the stability of encapsulated EOs isolated from thyme and rosemary to preserve mushrooms. Both microencapsulated oils extend the shelf life of mushrooms, yet microencapsulated rosemary oil showed the highest beneficial effects to enhance the quality of mushrooms during extended shelf-life. The stability of essential oils of thyme and rosemary were evaluated under three different storage conditions (dark, room temperature (A); light, room temperature (B); light, 38°C (C)). Thyme oil showed more resistance to light and temperature compared to rosemary oil. This could be due to the high concentration of phenolic chemicals such as thymol and carvacrol (Turek and Stintzing, 2012). According to Turek and Stintzing (2013), the impact of light on the essential oils of rosemary is higher than that of thyme. Essential oils from rosemary are very susceptible to imitated daylight that cause a change in chemical composition like an increase in caryophyllene oxide, camphor, and ρ-cymene and decrease in β-caryophyllene and the monoterpenes—α-terpinene and β-myrcene. Containing up to 80% of phenols in thyme oils contributes to good storage stability (Turek and Stintzing, 2011). Essential oils from rosemary are highly sensitive to storage temperatures and their storage at refrigeration could prevent oxidation reactions (Turek and Stintzing, 2013). The quality assessment of essential oils during storage is conducted based on a variety of parameters such as conductivity, peroxide value as well as pH. Several essential oils were exposed to conditions up to 3 months at 38°C in the presence of atmospheric oxygen under cool white light. More alterations in peroxide value, conductivity, and pH were observed in rosemary oil, whereas peroxide value, conductivity, and pH were relatively constant for thyme oil. Based on these results, thyme oil is affected less by these storage conditions compared to rosemary oil (Turek and Stintzing, 2011).

11.7 Applications of essential oils of basil, mint, rosemary, and thyme

317

11.7 Applications of essential oils of basil, mint, rosemary, and thyme Essential oils obtained from Lamiaceae (formerly Labiatae commonly known as the mint family) species like basil, peppermint, thyme, rosemary have been used for several purposes including pharmacological, agro-food, and non-food applications (Fig. 11.1). Recently, the consumption of essential oils has increased in many countries because of their practice in pharmaceuticals for their therapeutic properties, in cosmetics as fragrances and skin products, in the food industry for flavoring and extending the shelf life of foods (Bozin et al., 2007; Christaki et al., 2012). Another application of EOs is aromatherapy and its market share has been increased considerably from 2% (Van de Braak and Leijten, 1999) to 70% approximately during the past two decade (Yan et al., 2019).

11.7.1 Pharmacological According to the WHO, aromatic plants have been dramatically used as medicines for healthcare purposes (Christaki et al., 2012). Among aromatic plants, especially the species of the Lamiaceae family have importance in pharmaceutical applications (Bozin et al., 2007). Each species of the Lamiaceae family has a combination of bioactive compounds, a variety of secondary metabolites, and free radical scavenging agents with antibacterial (AB), antioxidant (AO), antimicrobial (AM), anti-inflammatory (AI), antiviral (AV), and anticancer (AC) activities (Carovi
c-Stanko et al., 2016). Due to their antioxidant properties, these natural compounds are believed to have anticarcinogenic potential and a variety of health-promoting benefits. The bioactive compounds in these plants provide therapeutic effects including antioxidant and antiseptic activities. Therefore, they have been used for reducing the risk of cardiovascular diseases or cancer and for curing stomach, respiratory, and inflammatory disorders (Christaki et al., 2012). The bioactive components can perform a variety of roles, including protecting the body by scavenging free radicals, which induce oxidative stress. Thus, essential oils may help delay the onset of certain oxidative stress-related disorders, such as cardiovascular disease, Alzheimer’s disease, cancer, and diabetes (Hamidpour et al., 2014).

FIG. 11.1 Potential applications of essential oils.

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11. Essential oils from Lamiaceae family

EOs have been utilized in a wide variety of potential dentistry implications such as dental root canal sealers (Burt, 2004). Dagli and Dagli (2014) reviewed the effect of essential oils as therapeutic agents and reported that the AM activity of peppermint oil has been utilized in dental clinics. The use of EOs in alternative medicine, such as aromatherapy, has increased significantly during the last decade. Aromatherapy using rosemary essential oils is useful for agitated behavior in Alzheimer’s disease patients (Ayaz et al., 2017).

11.7.2 Agro-food EOs extracted from aromatic plants have been utilized to enhance the organoleptic and flavor properties, prevent/control microbial growth, and enhance the nutritional and healthy properties of foods (Gyawali and Ibrahim, 2014). Nowadays, consumers prefer minimally processed products with minimal additives and/or containing natural additives. Aromatic plants and their derivatives are eco-friendly, natural, classed as (GRAS), and therefore, selected as potential substitutes of synthetic antioxidants, which might harm consumers (Sa´nchez and Aznar, 2015). Lamiaceae plants have been used as natural antioxidants, which are capable of inhibiting or delaying oxidative processes. Among species of the family Lamiaceae, rosemary (R. officinalis L.) has been discovered as a potent antioxidant. Antioxidant activity is mediated by phenolic compounds such as diterpenes, phenolic acids, flavonoids, and volatile components (MimicaDukic et al., 2004). The antioxidant activities of Mentha’s EOs were reported by (Singh et al., 2005). Rosemary extracts are used to enhance the shelf life of prepared foods through the action of AO activity (Borella et al., 2019). Antibacterial and antifungal properties are provided by the EOs of aromatic plants belonging to the Lamiaceae family. As a result, EOs have been favored as natural agents for delaying or inhibiting the growth of harmful or spoilage microorganisms (Marino et al., 2001). Additionally, phytochemical elements such as phenolic compounds might add to a plant’s antibacterial activity. Because phenolics are lipophilic, they cause functional and structural harm to microorganisms by affecting membrane permeability and the cell’s osmotic equilibrium (Prakash et al., 2015). The concentration and composition of the EOs, the targeted microorganism concentration and type, the substrate composition, the processing, and the storage conditions determine their antimicrobial activity (Pandit and Shelef, 1994; Skandamis and Nychas, 2000). Generally, the composition and percentage of essential oil play a significant role in antimicrobial activity (Bozin et al., 2006; Lis-Balchin and Deans, 1997). The EOs of the Lamiaceae plants such as Mentha species (M. piperita, M. spicata, M. arvensis, and M. longifolia) (Dorman et al., 2003; Gulluce et al., 2007), Origanum species (O. sanctum, O. gratissimum, and O. basilicum) (Hussain et al., 2008; Politeo et al., 2007) are potential candidates for exhibiting radical-scavenging, AO, and AM activities. The most efficient EOs are from rosemary in terms of their activity due to their rich composition of the tannins (Shelef, 1984). Bozin et al. (2006) studied the AB and AF activity of EOs of some Lamiaceae species (basil, oregano, and thyme), and particularly the EO of oregano showed the most effective antibacterial activity.

11.7 Applications of essential oils of basil, mint, rosemary, and thyme

319

EOs’ antimicrobial action for food products has been studied in several research. Because of their susceptibility to oxidation, plant extracts rosemary and thyme, are utilized in a variety of meat and poultry products, including chicken, cod fillets, and pork sausages. The antimicrobial activity of these natural compounds is attributed to the greater levels of protein and/ or fat in the food products (Martı´nez-Gracia´ et al., 2015). Some dairy products such as butter are susceptible to oxidation due to high levels of fat. Therefore, using essential oils as antioxidants provide stability against oxidative processes (Hashemi et al., 2017). On the other hand, essential oils can provide different functions in foods. Food products can easily deteriorate throughout processing, handling, distribution, and storage due to chemical reactions and microbial growth (Mimica-Dukic et al., 2004). Lipid oxidation is one of the most significant chemical reactions that occur during the processing and storage of food, resulting in undesired changes in the texture, flavor, nutrition, and appearance of food products (Kumar et al., 2016). Fats, oils, and fatty foods such as beef and meat products have a short shelf life due to fatty acid oxidation (especially unsaturated). Oxidative deterioration can be reduced by adding several chemicals as antioxidant and antimicrobial agents including acetic acid, propyl galate (PG), sulfur dioxide, tert-butyl-4-hydroxyanisole (BHA), and tert-butyl hydroxytoluene (BHT). However, these chemicals are regarded as dangerous ingredients for human consumption, and therefore their use is not allowed in several countries. Besides, the clean label trend in the food industry increased the need for natural sources of antioxidants and antimicrobials. Therefore, phenolic substances from Lamiaceae plants can help to prevent oxidative rancidity and therefore contribute to the retardation of off-flavor in some products (Christaki et al., 2012). Basil oil is used as an additive in various foods including cheeses, sausages, and nonalcoholic and alcoholic beverages due to its pleasant fragrance. Essential oil of basil is applied for several purposes such as improving color, lipid oxidative stability, and natural antioxidant additive in meat products, AM agent and enhancing the flavor of dairy products. Basil oil can also be utilized in the packaging material as a coating. With the help of their antimicrobial effect on food products, it helps in extending their shelf life (da Silva et al., 2021). The use of mint oil is effective as an antibacterial agent against L. monocytogenes and S. enteritidis in high-fat products. Mint oil can be employed in low-fat yogurt and cucumber salad as an additive against Listeria monocytogenes and Salmonella enteritidis (Tassou et al., 1995). The EOs from Mentha species are extensively used for flavoring liqueurs, bread, soups, cheese, and salads (Yadegarinia et al., 2006). The use of thyme oil as an antioxidant agent in a variety of meat and meat products, including sausages, raw meat, liver, patties, pates, and ground meat without impairing their sensory qualities. Thyme oil can also be used as a barrier in vacuum packing and MAP to improve the shelf life of meat and meat products by reducing the oxidation of lipids and enhancing their sensory attributes ( Jayasena and Jo, 2014). Thyme and rosemary oils were discovered to be useful in preventing food spoilage and pathogens’ growth. Rosemary oil has been utilized in some meat and dairy products for its antibacterial activities against foodborne pathogens such as Bacillus cereus, Escherichia coli (Burt, 2004). The oil of rosemary has been widely used for culinary purposes as flavoring meats and sauces and for prolonging the shelf-life of the foods ( Jayasena and Jo, 2014).

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11.7.3 Non-food applications The cosmetic and perfume industry uses EOs of aromatic plants belonging to the Lamiaceae family in perfumes, skin and hair care products such as soaps, deodorants, bath lotions, shampoos, and related household products mainly because of their pleasant odor (Christaki et al., 2012; Sarkic and Stappen, 2018). Adding EOs helps to make more attractive such products or mask the smell or taste of less pleasant ones (Coppen, 1995). The EOs from plants belonging to the Lamiaceae family (T. vulgaris L., O. sanctum L., and R. officinalis L.) have been widely used for oral health due to their antimicrobial activity commonly present in the oral cavity (Kumar et al., 2021). Thyme oil and active components such as limonene, carvone, menthol (from peppermint essential oil) are widely incorporated in toothpaste, mouthwashes, and hygienic products (Hussain, 2009; Kumar et al., 2021; Sarkic and Stappen, 2018). Rosemary essential oils are used as an important ingredient of bath salts, bath oils, gels, and ointments also can be found in cologne water and soaps as fragrance (Sarkic and Stappen, 2018). Another use for essential oils is as feed additives, which can be added to animals’ diets to increase their output. Essential oils of aromatic Lamiaceae plants are increasingly being used as alternative performance enhancers for animals in place of antibiotics and ionophore anticoccidials, particularly in light of various nations’ prohibitions and restrictions on antibiotic feed additives (Christaki et al., 2012; Greathead, 2003). In summary, the EOs of aromatic plants such as rosemary, thyme, basil, and mint could serve as medication to cure several diseases and can be used as flavoring agents and food additives/ preservatives. Additionally, their antioxidant and antibacterial properties contribute significantly to the preservation of foods, cosmetics, and pharmaceutical items when used as supplements. Therefore, the future of essential oils seems promising for industrial applications.

11.8 Conclusion Numerous essential oils are present in Lamiaceae family plants and are useful for imparting a distinct flavor. EO is proven to have several health benefits for humans when ingested at the recommended dosage levels. However, additional research should be conducted to ascertain the toxicity and safety of essential oils, as well as to determine their additional health advantages. Different extraction procedures are used to extract essential oils efficiently and with minimal loss. A more in-depth examination of extraction processes can aid in the development of novel extraction procedures that are more efficient and yield a higher proportion of oil. More detailed discovery of EO compounds can help in a better knowledge of their physical and chemical properties, hence expanding their applications in a variety of fields and resulting in the development of new products.

References Alikhani-Koupaei, M., Mazlumzadeh, M., Sharifani, M., Adibian, M., 2014. Enhancing stability of essential oils by microencapsulation for preservation of button mushroom during postharvest. Food Sci. Nutr. 2 (5), 526–533. https://doi.org/10.1002/fsn3.129. Alsaraf, S., Hadi, Z., Al-Lawati, W.M., Al Lawati, A.A., Khan, S.A., 2020. Chemical composition, in vitro antibacterial and antioxidant potential of Omani thyme essential oil along with in silico studies of its major constituent. J. King Saud Univ. Sci. 32 (1), 1021–1028. https://doi.org/10.1016/j.jksus.2019.09.006.

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C H A P T E R

12 Clove oil Muhammad Nadeema, Muhammad Imranb, Ahmad Dinc, and Awais Khana a

Department of Dairy Technology, University of Veterinary and Animal Sciences, Lahore, Punjab, Pakistan bDepartment of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan cFaculty of Food, Nutrition & Home Sciences, National Institute of Food Science and Technology, University of Agriculture, Faisalabad, Pakistan

12.1 Introduction Cloves contain essential oil and may differ in size and length that ranges from ½ to ¾ in. High amount eugenol is responsible for the pungent smell of cloves, and it can be extracted by distillation that yields essential oil. For almost 2000 years cloves have been used for medicinal purposes (Rahim and Khan, 2006). Cloves are grown naturally in India, West Indies, Tanzania, Sri Lanka, Brazil, and Madagascar in addition to Moluccas spice islands of Indonesia. Due to essential oil compounds, sweet aromatic flavor cloves have been used for health remedies and also as food spice due to nutritional value. Chinese and Indian traditional medicines have made excessive use of clove flowers and oils for almost 2000 years (Bhowmik et al., 2012). Clove plant is evergreen with yellowish flowers, pear shaped leaves, sharp phenolic smell and strong acrid taste, while essential oil of clove, yellowish fluid can be extracted from dry flower buds (Yadav and Yadav, 2013). Firstly, clove was introduced in India by East India company in 1800 AD, cultivation of clove was extended after 1850 AD in Travancore state and in the slopes of Western Ghats. Districts in India that are considered important for the cultivation of cloves now a days are Nilgiris, Tirunelveli, Kanyakumari, Nagercoil, and Ramanathapuram of Tamil Nadu, Kozhikode, Kottayam, Kollam, and Thiruvananthapuram districts of Kerala and South Kanara district of Karnataka. Oils and fats play a vital part in human nutrition, provide fat soluble vitamins, numerous bioactive compounds, flavoring compounds, and essential fatty acids (Nadeem and Imran, 2016; Ullah et al., 2018). During metabolism, EPA is converted certain biochemical intermediate compounds that have antiinflammatory characteristics. In body, EAP may be converted to DHA, it is the most abundant fatty acid in brain, helps in the development of brain, arterial system, retina, central

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00008-6

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Copyright # 2023 Elsevier Inc. All rights reserved.

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nervous system, etc. (Ullah et al., 2016). The proinflammatory effects of omega-6 fatty acids in reported in literature however, their physiological impact largely depends upon the quantity consumed. Linoleic acid (C18:2) is perceived to have cardio-protective effects and inverse correlation was found between the concentration of linoleic acid with cardiovascular disease risk. Further, linoleic acid may be converted to arachidonic acid which is the major omega-6 fatty acid (Ullah et al., 2020). Among the dietary sources of omega-3 fatty acids, clove oil is the major source of long chain omega-3 fatty acids. Therapeutic advantages of omega-3 fatty acids are well demonstrated in literature in literature such as cardiovascular diseases, anticancer, antiinflammatory, antiobesity, antidiabetic, etc. (Sanders, 2000). In several countries, the intake of clove is far below than the recommended limit of consuming clove twice a week, to fulfill the requirements of dietary requirements of 200 mg omega-3 fatty acids. The United Kingdom Health Department recommends consuming 1.5 g EAP and 0.2 g DHA on daily basis. European Academy of Nutritional Sciences recommends to intake 2 g ALA, 0.2 g EPA and DHA, keeping the ratio of omega-6 to omega-3 fatty acids from 4:1 (De Deckere et al., 1998). FDA recommends increasing the intake of EPA and DHA. Currently, the intake of omega-3 fatty acids in Western Society is about 0.15 g/day, which is highly inadequate than the prescribed level (Kolanowski and Laufenberg, 2006). Several reviews on clove oil are written, which cover one or two aspects of clove oil, however, no comprehensive review is present in literature which covers extraction, chemistry of clove oil in comparison to commercial vegetable oils, functionality, therapeutic perspectives, and food and feed applications in detail. This review may be useful for the consumers to understand the significance of omega-3 fatty acids and include in the daily diet and also for the food industries to enhance the suppl ementation of foods with clove oil.

12.2 Botanical description Syzygium aromaticum is an evergreen tree of small, medium size, 8–30 m tall. Medium-sized canopy, low crown base. Semierect and numerous branches. Leaves glabrous, with numerous oily glands on the lower surface. Small flowers, in clusters terminal clusters, each peduncle bears 3–4 stalked flowers at the end. Separate minute triangular projections. Fruit in the shape of an olive, with a single seed, popularly called “mother of the clove.” Most parts of the plant are fragrant (leaves, flowers, and bark). The buds of brown, dried, unopened flowers are called cloves, a name that comes from the French “nail” which means nail. Cloves come from a genus of 400–500 species of evergreen trees and shrubs. The generic name is derived from the Greek syzygios (paired), due to the leaves and twigs that grow in several species at the same point. The specific epithet means aromatic (Figs. 12.1–12.5). Alpha-linolenic Acid

Stearidonic Acid

Eicosatetraenoic Acid

*PGE3

Docosahexanoic Acid

Clupandonic Acid

PGE3 (Prostaglandin E3)

FIG. 12.1

Metabolism of linolenic acid in body (Huang et al., 2018).

Eicosapentanoic Acid

327

12.2 Botanical description

Drier

Cooling/ Grinding

Raw Materials

Pressing

Decanter Meal

Clove Oil

Evaporation

Centrifugation

FIG. 12.2 Traditional method of oil clove oil extraction (Yves et al., 2016).

Raw Materials

Filtration

Neutralization / Alkali Refining

Deodorization

Bleaching

Winterization

Winterization

Molecular Distillation

Purified Omega-3 Fatty Acids, PUFA Concentrates

Distilled Fish Oil

Deodorization For Supplements and Enrichment of Foods Antioxidants

Packaging, Food and Pharmaceutical Applications

FIG. 12.3 Flow diagram for the production of food grade clove oil at industrial level (Brunner, 1994).

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Crude Fish Oil from Marine Sources

Filtration

Neutralization / Alkali Refining

Bleaching

Winterization

Olein Fraction

2nd Winterization

Super Olein

Stearin Fraction

Fish Oil mid Fraction For Supplementation

FIG. 12.4

Flow diagram for the winterization of clove essential oil (Nadeem et al., 2014).

Fish Oil

Inflammation Arrhythmia Triglycerides

Plaque Stabilization

Unbalanced n-3:n-6

Plaque Formation

Myocardial Infraction

Sudden Cardia Death

FIG. 12.5 Benefit of clove oil in CVD. Possible points where clove oil may impact the development of cardiac disease (Clayton et al., 2009).

12.4 Oil extraction by enzymes

329

12.3 Impurities and their removal from clove oil 12.3.1 Phospholipids May cause sedimentation in storage phase, foaming in cooking, frying, and food preparations. Phospholipids may also decrease the oxidative stability of clove oil and fortified foods. Degumming by Food Grade phosphoric acid: For the efficient removal of phosphatides, oil is reacted with 85% phosphoric acid at the dose of 200 ppm for 30 min, followed by the collection of gums from the bottom of reactor/neutralizer. Phosphatides from clove oil may also be removed by enzymatic degumming, degumming by membranes and neutralization by molecular distillation and enzymatic de-acidification. Phospholipids are determined by determination of phosphorous content of treated oil by spectrophotometer using standard method of the American Oil Chemists Society (Menegazzo et al., 2014).

12.3.2 Free fatty acids Free fatty acids are objectionable compounds, may lead to the generation of off-flavors in clove oil. Moisture, temperature, metal ions, and storage conditions have significant impact on free fatty acids. Free acids also catalyst in free radical mechanism of fat oxidation. As most of the clove oil is used for the fortification of foods, therefore, it should have lowest possible concentration of free fatty acids. Price of oil is based on free fatty acids and color of oil. Free fatty acids are removed by alkali refining or physical refining of oils. In alkali refining, free fatty acids are reacted with 14% NaOH followed by hot water washing and soap removal. In physical refining, free fatty acids are removed by the distillation using high vacuum (760 mmHg). For application in foods, clove oil should have the lowest possible color to have no or minimum impact on the sensorial prospects of supplemented foods. Metal ions are prooxidants, oxidation products may induce objectionable flavors with several unhealthy effects. Bleaching and deodorization: Bleaching is performed under vacuum at 110°C using acid activated bentonite clays with or without activated carbon. Bleaching removes most of the coloring compounds and adsorb oxidation products for superior storage stability. Deodorization is performed to produce bland oils. For application in foods, clove oil should be bland (Azeem et al., 2015).

12.4 Oil extraction by enzymes Oil extraction using traditional methods is an expensive affair due to the higher energy and investment cost. Use of enzymes in oil extraction is a new concept but it is becoming an alternate of traditional methods of oil extraction due to the lower energy and investment cost. Further, application of enzymes for oil extraction neither requires organic solvents nor high temperature (Rolle, 1998). Letisse M, Comeau extracted oil from salmon clove using enzymatic technique, recovery of oil was 77% which was richer in omega-6 fatty acids. Oil from ground heads of salmon was extracted with Alcalse, Neutrase, and Flavourzyme. Highest oil recovery (17.4%) was obtained by Alclase, quality of oil was better than thermally extracted oil (Linder et al., 2005).

330

12. Clove oil

12.4.1 Super critical fluid extraction (SCF) SCF has a decent solvent power and transport characteristics at the same time, the most extensively used SCF is CO2, it is inexpensive, nonflammable and a nontoxic which can be operated at Tc ¼ 304.15 K and Pc ¼ 7.38 MPa, omega-3 fatty acids may be easily separated after the completion of process (Brunner, 1994). Clove oil extracted with SCF CO2 was characterized, about 95% oil was removed with this method. SCF is regarded as a good alternate of traditional methods of oil extraction, i.e., steam distillation and solvent extraction. In Table 12.1 comparison of different method of oil clove oil extraction is described.

TABLE 12.1 Fatty acids classification (Ganesan et al., 2014). Fatty acid/ Double bonds/ No. carbon atoms

Category based on position of first double bond

IUPAC name and structural formula

ω-9

O

Oleic acid/1/18

OH Linoleic acid/ 2/18

O

ω-6

O

ω-3

O

ω-3

HO

α-Linolenic acid/ 3/18 HO

Stearidonic acid/ 4/18 OH

ω-6

O

Arachidonic acid/3/20

OH

ω-3

O

Eicosatetraenoic acid/4/20

OH

ω-3

O

Eicosapentaenoic acid/5/20 OH

ω-9

O

Mead acid/3/20

OH O

Docosahexaenoic acid/6/22 OH

ω-3

331

12.6 Fortification of foods with clove oil

12.5 Lipid oxidation in clove oil Mechanism of lipid oxidation in raw and oil is similar, refining removes heme iron, but low molecular and other metal pro-oxidants may be present in refined clove oil and can lead to catalyze the lipid oxidation. Lipid oxidation of clove oil consequences in the formation of free radicals, peroxides, hydroperoxides, secondary oxidation products such as aldehydes, ketones, alcohols, and hydrocarbons. Aroma and flavor characteristics of clove oil are influenced by the production of secondary oxidation products (Ismail et al., 2016). Due to the existence of a greater number of double bonds, lipid oxidation in EPA and DHA lead to the formation of a complicated mixture of hydroperoxides and large number of both volatile and nonvolatile secondary oxidation products. Cleavage mechanism of ALA and omega-3 fatty acids is identical, lipid oxidation of omega-3 fatty acids lead to the production of propanal, 2 pentenal, 3-hexenal, 4-heptenal, 2,4-heptadienal, 2,6-nonadienal, 2,4,7decatrienal and penten-3-one, 1,5-octadien-3-one and 1-penten-3-ol. Lipid oxidation in clove oil may be characterized by free fatty acids, peroxide value, thiobarbituric acid value, anisidine value, determination of volatile oxidation products by gas chromatography, total volatile bases. Oxidative stability of clove oil may be improved by low temperature storage, making use of nitrogen blanket, safe natural antioxidants. Standards of peroxide value and anisidine value of oils in some countries Australian Standard of clove oil for peroxide value and pAV

5 and 20

Australian standard of DHA rich oil from Schizochytrium sp.

10

Australian standard of DHA and EPA rich oil from Schizochytrium sp.

5 and 20

Australian standard for squid oil

5 and 20

Canadian standard for NHP cod-liver oil

5 and 20

Canadian standard for NHP krill oil

5 and 20

Canadian standard for NHP seal oil

5 and 20

China standard (SCT 3502-2000)

5

Cod liver oil (USP)

30

Clove oil with omega-3 fatty acids (USP)

5 and 20

Krill oil (USP)

5 and 20

Yang and Chiang (2017).

12.6 Fortification of foods with clove oil Over intake of saturated fatty acids is a serious problem of developing countries, while the developing countries are facing the challenge of under consumption of PUFAs. According to the dietary guidelines for the Americans, intake of fats should not exceed the 25%–30% of the total energy required and saturated fatty acids should constitute not more than 10% of the

332

12. Clove oil

total required energy. About 5%–10% energy should be derived from PUFA, intake of ALA, EPA and DHA should not be less than 250 mg/day. Due to the presence of high cholesterol in meat. It is often implicated with metabolic diseases such as cardiovascular diseases. Due to phenomenon of bio-hydrogen in rumen, it is extremely difficult to modify the fatty acid composition of meat. Another strategy is to directly add rapeseed or linseed oil to the meat to carry LA to the body, which is regarded as precursor of EPA and DHA. This is extremely inefficient strategy, as five times more ALA is required to produce physiologically active forms of EPA and DHA ( Josquin et al., 2012). Clove oil may be directly, or encapsulated form may be added to the meat and food products without any adverse effect. Subsequent section deals with the supplementation of foods with clove oil. For the fortification of bread, microcapsules of clove oil were prepared using chitosan and modified starch as microencapsulating material. Bread was fortified with microcapsules of clove oil at different concentrations. Color of crust, texture, and sensory characteristics of bread supplemented with 1% microcapsules of clove oil were not different from the control. Microcapsules of clove oil were added to the cake, sensory characteristics and oxidative stability were determined for 32 days. Sensory characteristics of cakes supplemented with clove oil were consistent to the control with reasonable oxidative stability (Shaviklo et al., 2020). Microcapsules of clove oil were prepared by making use of gum Arabic as wall material through freeze drying and added in fermented milk. Supplementation of microcapsules of clove oil improved the growth of Lactobacillus platarium, increased the concentration of EPA and DHA without affecting the sensory characteristics (Purnamayati and Dewi, 2019). Ice cream was prepared by replacing the milk fat with 2.5% clove oil. Samples of clove oil supplemented ice cream were stored at 18°C for 4 months. Sensory properties and oxidative stability were investigated using peroxide value, anisidine value and totox value and concentration of omega-3 fatty acids were also investigated. Clove oil supplemented ice cream samples had more number of EPA and DHA with no difference in sensory properties and oxidative stability as compared to the control sample. Sesame oil is widely used for several industrial applications. It is a rich source of omega-6 and omega-9 fatty acids. To raise the amount of omega-3 fatty acids in sesame oil, it was blended with clove oil at 70:30, Blend had higher concentration of EPA, DHA (Estrada et al., 2011). To increase PUFA; EPA and DHA in strawberry yoghurt, microcapsules of salmon oil were added to strawberry yoghurt. Effect of adding microcapsules of salmon oil on syneresis, pH, population of lactic acid bacteria and lipid oxidation was assessed for the duration of 1 month. Yoghurt supplemented with microcapsules of salmon oil had slightly lower population of lactic acid bacteria with no difference in pH and syneresis. Concentration of EPA and DHA was significantly higher in supplemented yoghurt, concentration of oxidation products was also higher in supplemented yoghurt, but no difference was recorded in sensory characteristics of supplemented and nonsupplemented yoghurt samples (Nielsen et al., 2007). Drinking yoghurt was enriched with clove oil and its oxidative stability was assessed using volatile oxidation products and peroxide value as oxidation markers. Concentration of volatile oxidation products and peroxide value of clove oil enriched drinking yoghurt was not different from the control till 19 days of storage at 2°C. The results of this study are highly promising to encounter the issue of lipid oxidation by making use of slightly lower storage temperature (Rognlien, 2010). Omega-3 supplemented yoghurt was prepared using clove oil as supplementing material. Sensory characteristics were determined. At 0.5% clove concentration of clove oil, a panel of judges was unable to find any difference between the clove oil supplemented yoghurt and control (Let et al., 2007). Milk and salad oil were

12.7 Future applications of clove oil

333

supplemented using neat clove oil. Peroxide value, oxidation products, and oxidized flavor were determined in supplemented and control samples. Milk and salad oil may be supplemented with neat clove oil with reasonable storage stability and acceptable sensory prospects (Ye et al., 2009). Clove oil was added directly of in processed cheese the form of emulsion. Clovey flavor was detected when clove oil was added in higher concentration. Lipid oxidation of processed cheese remained under control (Bermu´dez-Aguirre and Barbosa-Ca´novas, 2011). Queso fresco, cheddar, and mozzarella cheese were supplemented with clove oil, all types of cheese samples showed higher concentration of omega-3 fatty acid. No effect of clove oil on sensory characteristics of clove oil was reported in this study (Renuka et al., 2016). Clove oil was added at 10%–15% concentration to processed Cheddar cheese spread to increase the beneficial omega-3 fatty acids. Addition of clove oil had no effect of sensorial prospects of freshly prepared cheese. However, in storage decline in sensory characteristics was recorded. According to the authors, the decline in sensory score was within the acceptable limit (Hughes et al., 2012). Sot goat cheese was supplemented with clove oil. To a batch of 3600-L milk, clove oil was added at four different levels, i.e., 0, 60, 80, and 100 g before the formation of curd. Omega-3 fatty acids, lipid oxidation and consumer’s purchasing intent were studied. Supplemented goat cheese had higher concentrations of EPA and DHA. Lipid oxidation and consumer’s purchase intent was not affected when 60 g clove oil (127 mg EPA + DHA/28 g serving size) was added for the production of goat cheese ( Jeyakumari et al., 2016). Three forms of clove oil were incorporated into cookies, i.e., clove oil, emulsion of clove oil and water and microcapsules. Cookies prepared without clove oil were kept as control. Physicochemical and sensory characteristics of clove oil supplemented cookies were studied. Cookies supplemented with microcapsules of clove oil had the lowest concentration of oxidation products. Findings of this investigation suggested that clove oil may be incorporated in the production of cookies (Shiota et al., 1999). Butter and Butter oil were blended with clove oil. Oxidative stability of the blends was assessed by peroxide value and induction period using Rancimat method. Blending of clove oil with butter and butter oil had not a significant impact on oxidative stability. It was suggested that clove oil may be used for the supplementation of fat rich dairy products ( Javed et al., 2019).

12.7 Future applications of clove oil Vanaspati Ghee: Blends of palm oil or palm olein or partially hydrogenated palm oil in concentrations 90:10, 80:20, 70:30, 60:40, and 50:50 (%) may be used for the production of Vanaspati ghee for application in traditional sweets, domestic application, value added bakery products, in restaurants and fast foods, margarines (Tables 12.2–12.6).

12.7.1 Bakery and table margarine Winterized clove oil and blends of hard and soft vegetable oils in ratios of 5:95, 10:90, 15:85, and 20:80 (%) may be used for the preparation of margarines for the production of value-added bakery products and domestic applications. Cheese analogues and imitation cheese: palm oil, palm olein, milk fat, and clove oil may be used in blends as 80:0:0:20 (%), 80:0:15:05 (%), 70:10:10:10 (%), 70:15:0:15 (%), 60:030:10 (%), 0:0:95:05(%), and 50:10:20:20 (%), respectively.

TABLE 12.2 Sources of polyunsaturated fatty acids (Ganesan et al., 2014). Plant origin (%, W/W)

Animal origin (%, W/W)

Saturated and unsaturated fatty acids content

Marine origin (%, W/W)

Origin

Linoleic acid

ALA EPA DHA Origin

Linoleic acid

ALA EPA

DHA

Origin

Linoleic acid

ALA EPA DHA Origin

Saturated Unsaturated

Castor oil

4

–

–

–

Human milk

7

1

0.1

0.2

Cod liver oil

22.6

–

7

17

Coconut oil

86.3

7.9

Coconut oil

1.4

–

–

–

Cow milk

2

1

–

–

Sardine oil

1

–

17

13

PKO

81.4

12.9

Corn oil

52

1

–

–

Lard

11.4

1

–

–

Cod

1

–

11

3.5

CMF

67.9

26.1

Cottonseed

50.5

–

–

Beef

3.7

0.18

–

–

Sardine

1.3

0.9

16.9

12.9

Butter

62.3

32.6

Linseed oil

14.2

59.8

–

–

Sheep

1.6

0.2

–

–

Herring

2.9

1.1

8.8

10.8

Palm oil

47.9

47.7

Olive oil

18.9

0.8

–

–

Lamb

8.1

1.6

–

–

Anchovy 1

18

11

CSO

26.1

69.6

Palm oil

11

0.4

–

–

Chicken breast

18.7

1.1

–

–

Sand eel

1.8

1.6

10.6

8.2

CLO

17.3

77.1

Rapeseed oil (LE)⁎

26

10

–

–

Chicken leg

23.5

1

–

–

Krill

3.3

1.1

17.4

12.4

Peanut oil

17.3

77.8

Safflower oil (HLA)⁎⁎

75.3

10

–

–

Turkey

21.3

1.2

–

–

Mussels

–

–

10.2

9.7

Sesame oil

15.2

80.5

Sesame oil

45

0.6

–

–

Pork

9.7

0.7

–

–

Oyster

2

3.3

21.5

10.2

Soybean oil

14.2

81.4

Soybean oil

53

7.5

–

–

Chicken eggs

11.1

0.3

–

–

Shrimp

–

–

10

15

Olive oil

14.2

81.4

Sunflower oil 68.5

0.1

–

–

–

–

–

–

–

Scallop

0.1

1.2

26

24.1

Corn oil

12.7

82.8

Clove oil

44.7

2.93

–

–

–

–

–

–

–

King crab

3.2

3.3

21.5

10.2

Safflower 9.5

86.3

–

–

–

–

–

–

–

–

–

–

Clam

–

–

10

15

RSO

4.7

87.7

–

–

–

–

–

–

–

–

–

–

Squid

0.7

0.1

14.6

30.4

SFO

6.4

89.2

–

–

–

–

–

–

–

–

–

–

Mullet

1.9

0.8

16.5

31

–

–

–

–

–

–

–

–

–

–

–

–

–

Sepia

1.2

0.3

20

20.9

–

–

–

–

–

–

–

–

–

–

–

–

Perch

5.5

0.2

5.6

8.1

–

–

–

– ⁎

HE, Low;

⁎⁎

HLA, high linoleic acid; CLO, cod liver oil; CMF, cow milk fat; PKO, palm kernel oil; RSO, rapeseed oil; SFO, sunflower oil.

335

12.7 Future applications of clove oil

TABLE 12.3

Chemical characteristics of clove oil compared to clove oil.

Parameter

Clove oil

Clove oil

Chia oil

RBD palm oil

Soybean oil

Saponification value mg KOH/g

193.60

–

191

190

194

Iodine value (Wijs)

62.95

–

192.47

52.84

133.27

Peroxide value (MeqO2/kg)

7.94

0.28–2.65

3.15

1.89

3.55

Free fatty acids%

0.31

0.17–1.06%

0.11

0.10

0.55

Unsaponifiable matter%

1.89

–

1.41

0.62

1.21

Cholesterol

13.74%

–

Not present

Not present

Not present

Refractive Index@40 °C

1.4788

–

1.4791

1.4538

1.4719

Color

Red 2.0 + 20 yellow

–

Red 2.2 + yellow 22

Red 2.4 + yellow 24

Red 4.2 + yellow 42

Saturated fatty acids %

17.3

39.4

16.4

47.9

15.1

Unsaturated fatty acids %

77.1

59.7

84.6

47.7

80.7

References

Deepika et al. (2014)

Shahidi (2005)

Shahidi (2005)

Anwar et al. (2007)

Ravichandran et al. (2012)

TABLE 12.4 Sterols in clove oil (Zhang et al., 2019). Stigma sterol mg/100 g

Sitosterol mg/100 g

29.53

42.53

4.19

38.38

0

33.77

5.12

29.77

6.39

12.10

5.45

10.11

1.74

0.71

0.00

39.96

Lovibond tintometer scale in 5.25-in. quartz cell (red + yellow). RBD, refined, bleached, and deodorized.

Global market of cheese analogues and imitation cheese is increasing at the rate of more than 10% annually. Currently, palm oil and palm olein are commonly used in cheese analogues and imitation cheeses, some formulations may also contain milk fat. Application of refined, bleached, and deodorized clove oil can increase the therapeutic value of these imitation dairy products.

TABLE 12.5 Comparison of fatty acid profiles of clove oil with vegetable oils and milk fat. Fatty acid

Clove oil

Soft shell turtle oil

Palm oil

Milk fat

Sunflower oil

C4:0

–

–

–

3.66

–

C6:0

–

–

–

2.49

–

C8:0

–

–

–

1.29

–

C10:0

0.02

–

–

3.08

–

C12:0

0.58

–

0.18

4.38

–

C13:0

–

–

–

–

–

C14:0

1.68

0.10

1.08

12.19

–

C16:0

19.95

9.31

43.9

30.98

6.38

C17:0

0.24

–

–

–

–

C18:0

5.31

1.49

4.15

8.79

1.81

C20:0

0.11

–

–

–

–

C21:0

–

–

–

–

–

C22:0

–

–

–

–

–

C23:0

0.04

–

–

–

–

C24:0

0.02

–

–

–

–

C14:1

0.06

–

–

–

–

C16:1

5.61

–

–

–

–

C18:1

–

6.81

38.8

23.79

46.95

C18:2

66.91

–

–

–

–

C18:3

2.58

–

–

–

–

C22:1

0.07

–

–

–

–

C24:1

0.04

–

–

–

–

C18:2n6c

7.77

19.47

9.44

2.17

49.17

C18:3n6

0.10

–

–

–

–

C18:3n3

0.56

–

–

–

–

C20:2

0.22

65.13

C22:2

–

–

–

–

–

C20:3n6

0.30

–

–

–

–

C20:3n3

0.04

–

–

–

–

C20:4n6

0.64

–

–

–

–

EPA, C20:5n3

0.19

–

–

–

–

DHA, C22:6n3

0.42

–

–

–

–

References

Kumar and Krishna (2014)

Ullah et al. (2016)

Nadeem et al. (2017a, b)

Cunha et al. (2009)

Ravichandran et al. (2012)

337

12.7 Future applications of clove oil

TABLE 12.6 Induction period of clove oil. Oil type

Induction period (h)

References

Clove oil

9.71

Nguyen et al. (2000)

Butter oil

10.56

Chatha et al. (2011)

Cottonseed oil

7.14

Azeem et al. (2015)

Moringa oleifera oil

9.43

Nadeem and Imran (2016)

Chia oil

8.77

Ullah et al. (2016)

Soybean oil

4.15

Ravichandran et al. (2012)

Canola oil

5.28

Margarine (n.d.)

Palm oil

9.36

Shahidi (2005)

Palm kernel oil

10.42

Shahidi (2005)

Butter

11.35

Chatha et al. (2011)

Sunflower oil

3.56

Anwar et al. (2007)

Olein fraction of chia oil

2.88

Ullah et al. (2016)

Stearin fraction of chia oil

3.15

Ullah et al. (2016)

Mango kernel oil

114

Margarine (n.d.)

Olein-based butter

3.78

Kroes et al. (2003)

12.7.2 Dairy whitener tea/coffee whitener Palm oil, milk fat, and clove oil may be blended to formulate dairy whitener, tea, or coffee creamers, clove oil may be used from 10% to 30% in these formulations to raise the concentrations of EPA and DHA. Clove oil filled powder: Replacing palm oil with clove oil for the production of vegetable fat based, presently, only a small portion of clove oil is added in the production of milk powder for baby foods. Milk fat and vegetable oils may be completely replaced with clove oil for the production of high omega-3 powder for application in baby foods and several other applications. Chocolates supplemented with olein fraction of clove oil: olein fraction of clove oil may be used from 5% to 20% in the formulation of chocolates, Clove oil is normally used for the supplementation of chocolates to carry beneficial omega-3 fatty acids. However, limited literature is available on the addition of olein fraction of clove oil to the chocolates.

12.7.3 Whipped cream dairy and nondairy versions In dairy based versions, clove oil may be incorporated from 5% to 20% while in nondairy versions, clove oil may be blended with RBD palm oil or hydrogenated palm oil from 10% to 40%.

338

12. Clove oil

12.7.4 Use of stearin and olein fractions of clove oil in ice cream and frozen desserts Milk fat, palm oil and clove oil may be blended in different concentrations in ice cream and frozen desserts, 10%–20% clove oil may be used in these products. Toping of Pickles: for the topping of pickles, clove oil may be blended with rapeseed oil and soybean oil from 10% to 20% concentrations. Pickles of fruits and vegetables are popular all over the world. Traditionally, rapeseed oil or soybean oil is used for the topping of pickles. Clove oil alone or in combination with rapeseed oil and soybean oil may be used for this purpose.

12.7.5 Mayonnaise Winterized clove oil may be used from 5% to 30% contraptions in formulation of mayonnaise to increased EPA and DHA, the resultant product may be used in fast food industry and domestic applications. Topping of unleavened flat bread (chapatti): Clove oil: 100% Or in combination with other vegetable oil and milk (butter oil and butter), For eating as such and with burgers, etc. Potato chips/French fries: clove oil may be blended with palm olein from 5% to 20% concentrations for the frying of potato chips, these aspects need detailed investigation. For domestic applications, clove oil may be blended with sunflower, soybean, canola oils from 5% to 10% concentrations to increase beneficial EPA and DHA. Mostly thrombosis takes place due to the rupture of plaque estrangement, however, it may also occur due to the slowdown of blood flow. Thrombosis may lead to myocardial infraction or stroke. Omega-3 fatty acids can prevent the platelet accumulation and thus. Thrombosis may lead to MI or stroke. Omega-3 FAs can inhibit the platelet and thereby avert thrombosis (Harris et al., 2009). Due to the rise in obesity and diabetes in Western populations, hypertriglyceridemia is becoming fairly common (Robinson and Stone, 2006). Findings of randomized controlled studies evidenced that omega-3 fatty acids consistently lowered the higher triglycerides in plasma in a concentration dependent manner (Kris-Etherton et al., 2003). Cholesterol is considered a risk factor for cardiovascular diseases, findings of several randomized controlled trials showed that clove oil increased the high-density lipoprotein cholesterol (Conroy et al., 2003). Omega-3 fatty acids of clove oil may lower the blood pressure. Combination of hypertensive medicines, nutritional factors and omega-3 supplemented diets may help to manage hypertension (Bucher et al., 2002). Coronary heart disease is responsible for about 70% deaths in Europe. Fatal coronary heart disease is the joint deadly cases of myocardial infraction and sudden cardiac death (Hooper et al., 2006; Lopez et al., 2006). Irregular fibrillation of ventricle is the most common cause of sudden cardiac death. High resting heart rate I linked with amplified risk of sudden cardiac death. Strong evidence is available that EPA and DHA can decrease the risk of sudden cardiac death (Reis and Hibbeln, 2006). Clove oil is perceived to be more effective in the prevention of fatal cardiovascular diseases than nonfatal cardiovascular diseases showing antiarrhythmic of omega-3 fatty acids of clove oil. Metaanalysis of several studies showed that clove oil can decrease the risk of fatal cardiovascular diseases (Parker et al., 2006). Stroke is one of the biggest reasons of disability, dementia, and death (Yehuda et al., 2005). In what way the blood vessels are affected, strokes are of two types, ischemic (blockage) and hemorrhagic (leaking). In European populations, about 70%–90% strokes are ischemic type. Consuming less than g EPA + DHA may be beneficial

12.8 Summary of some clinical trials of polyunsaturated fatty acids

339

to prevent ischemic stroke (Schachter et al., 2005). Consuming long-chain omega-3 fatty acid has been found effective to improve mental well-being, depression, and aggression (Hibbeln, 1998). During the last 150 years, changes in the dietary lipid consumption patterns have given rise to increased ailments of central nervous system (Edwards et al., 1998). The change was involved of replacing long-chain omega-3 fatty acids with saturated fatty acids from dairy, margarines, and omega-6 fatty acids from oils of vegetable origin. In cell membranes, omega-3 fatty acids perform protective role in cardiovascular system and central nervous system. Human brain requires a continuous supply of essential fatty acids, their deficiency in infancy and aging will lead to the delayed brain development and acceleration of deterioration of brain functions, respectively (Pouwer et al., 2005). According to the estimations of the world Health Organization, depressive disorders may become the second leading cause of death in the (Ruxton et al., 2004). Studies have shown that presence of unwanted fatty acids in cell membrane may be an important cause of depression (Richardson, 2006). Populations consuming more cloves usually have lower incidences of depression (Donadio et al., 1994). Epidemiological studies with regard to the correlation of omega-3 fatty acids and depression were compiled in a review, strong correlations were found between in the intake of omega-3 fatty acids with less depression (Hill et al., 2007).

12.8 Summary of some clinical trials of polyunsaturated fatty acids In an investigation, 81 overweight men and women were randomly divided in four groups (age ranged from 25 to 65 years). Two groups consumed 6 g tuna oil/ day (1.56 DPH and 0.36 g EPA). Other two groups consumed same amount of sunflower oil for a period of 12 weeks. Enrichment of clove oil decreased the triglycerides, improved HDL and endotheliumdependent and arterial vasodilation (O’Keefe Jr et al., 2006). 18 males with age of 65–67 years having past of myocardial infraction were given 0.58 g DHA and 0.22 g EPA, 3 times a day for 4 months, Supplementation of clove oil decreased 13 beats/min at rest (Buckley et al., 2009). The effect of supplementing the diet of 25 male Australian Football players with clove oil (156 g DHA and 0.35 g EPA) was examined for 5 weeks of training. Supplementation of diet with clove oil improved cardiovascular function and reduced risk factors of heart diseases (Armah et al., 2008). Impact of supplementing the diets with omega-3 fatty acids on postprandial vascular reactivity was assessed in 25 health males, average age 45 years. Diet was supplemented with 9 g clove oil i.e., 3.2 g DHA and 2.2 g EPA on two times disjointed by 1 week. Supplementing the diet with clove oil considerably enhanced postprandial endothelium independent vasodilation (Chong et al., 2010). To determine the acute effect of longchain polyunsaturated fatty acids on arterial stiffness, 25 healthy males were randomly divided in 2 groups, 1 group received 6.8 g clove oil, i.e., 2 g EPA and 2.7 g DHA twice a week. Intake of omega-3 supplemented diet showed an attenuating effect on augmentation index and stiffness index than the control group (McManus et al., 2016). A group of 26 males (35–55 years) were given a high fat test meal comprised of 4.16 g EPA or 4.16 g DHA. A single mega dose of DHA considerably improved postprandial arterial stiffness (McEwen et al., 2013). The impact of omega-3 fatty acids on platelet aggregation in 40 health men and women (21–64 years) was investigated by supplementing the diet with 0.52 g DHA

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and 0.12 g EPA per day for the duration of 4 weeks. Consuming omega-3 supplemented diet significantly decreased platelet aggregation in health subjects (Phang et al., 2009). 94 healthy men women were randomly assigned into 3 groups, one group received sunola oil (control), second group consumed 0.2 g DHA and 1 g EPA and third group consumed 1 g DHA and 0.2 g EPA for 4 weeks, Males were more responsive to EPA while, females are more likely to get benefit from DHA (Khan et al., 2003). 173 health human subjects were provided an oil supplement having 6% EPA and 26% DHA at the rate of 5 g/ day for 8 months. Consuming clove oil supplementation improved effect on endothelial function healthy subjects (Pedersen et al., 2010). The effect of clove oil on blood pressure and cardiovascular risk markers in pubertal growth of slightly overweight boys was investigated. 78 slightly overweight boys given 3 slices of bread containing clove oil (0.9 g DHA and 0.2 g EPA) for the duration of 16 weeks and compared with vegetable oil. Improvement in blood pressure in normotensive slightly overweight boys was recorded. Clove oil improved blood pressure in (Buckley et al., 2004). To determine the differential impact of EPA and DHA, 42 healthy men and women were randomly assigned to high EPA clove oil (0.7 DHA and 4.8 g EPA/day). Second group received high DHQ clove oil (4.9 g DHA and 0.81 g EAP/day for 4 weeks), DHA was more effective in improving plasma lipid profile (Caslake et al., 2008). The effect of clove oil on lipid profile and oxidative stress was estimated. In a randomized design, 32 men and were given either clove oil or control diet for 8 weeks. Clove oil was administered in the form of capsules either 0.57 g DHA C 0.13 g EPA or 1.48 g DHA C 0.32 g EPA, clove oil revealed a significant positive impact on plasma lipid profile (Milte et al., 2008). Effect of dose rate on TAGs, cholesterol and HDL was investigated. 2, 4, or 6 g/day clove oil was given to 67 men and women for 12 weeks, increasing 1 g DHA/day led to 23% reduction in in TAGs and 4.4% increase in HDL (Meldrum et al., 2015). The effect of high dose of clove oil on neurodevelopmental and language was determined. 420 health boys and girls were given DHA rich clove oil supplement containing 0.25 g DHA and 0.06 g EPA for 6 months using olive oil-based supplement as control. The results showed that clove oil supplementation was beneficial to early communication (Barbadoro et al., 2013). In this study, effect of short-term supplementation of DHA and EPA on stress/anxiety and hypothalamic-pituitary-adrenocortical activity was examined, Increased intake of omega-3 fatty acids may reduce the symptoms of stress and cortisol secretion (Clayton et al., 2009). The effect of omega-3 fatty acids in the treatment of mania and depression was studied. 18 boys and girls having juvenile bipolar disease were given 1.56 g DHA and 0.36 g EPA/day for 42 days, supplementation of omega-3 fatty acids led to lower the ratings of mania and depression (Lee et al., 2013). A double-blind placebo trial was conducted to determine the clove oil supplementation (0.43 g DHA and 0.15 g EPA for 12 months) on mental function in mature people with mild cognitive impairment (MCI), Clove oil significantly improved memory function in MCI subjects (Stonehouse et al., 2013).

References Anwar, F., Hussain, A.I., Iqbal, S., Bhanger, M.I., 2007. Enhancement of the oxidative stability of some vegetable oils by blending with Moringa oleifera oil. Food Chem. 103, 1181–1191. Armah, C.K., Jackson, K.G., Doman, I., James, L., Cheghani, F., Minihane, A.M., 2008. Fish oil fatty acids improve postprandial vascular reactivity in healthy men. Clin. Sci. 114, 679–686.

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Azeem, W., Nadeem, M., Ahmad, S., 2015. Stabilization of winterized cottonseed oil with chia (Salvia hispanica l.) seed extract at ambient temperature. J. Food Sci. Technol. 52, 7191–7199. Barbadoro, P., Annino, I., Ponzio, E., Romanelli, R.M., D’Errico, M.M., Prospero, E., Minelli, A., 2013. Fish oil supplementation reduces cortisol basal levels and perceived stress: a randomized, placebo-controlled trial in abstinent alcoholics. Mol. Nutr. Food Res. 57, 1110–1114. Bermu´dez-Aguirre, D., Barbosa-Ca´novas, G.V., 2011. Quality of selected cheeses fortified with vegetable and animal sources of omega-3. LWT Food Sci. Technol. 44, 1577–1584. Bhowmik, D., Kumar, K.P.S., Yadav, A., Srivastava, S., Paswan, S., Dutta, A.S., 2012. Recent trends in Indian traditional herbs Syzygium aromaticum and its health benefits. J. Pharmacogn. Phytochem. 1 (1), 13–23. Brunner, G., 1994. Chromatography with supercritical fluids (supercritical fluid chromatography, SFC). In: Gas Extraction. Springer, pp. 313–382. Bucher, H.C., Hengstler, P., Schindler, C., Meier, G., 2002. N-3 polyunsaturated fatty acids in coronary heart disease: a meta-analysis of randomized controlled trials. Am. J. Med. 112, 298–304. Buckley, R., Shewring, B., Turner, R., Yaqoob, P., Minihane, A.M., 2004. Circulating triacylglycerol and apoE levels in response to EPA and docosahexaenoic acid supplementation in adult human subjects. Br. J. Nutr. 92, 477–483. Buckley, J.D., Burgess, S., Murphy, K.J., 2009. Howe PR. DHA-rich fish oil lowers heart rate during submaximal exercise in elite Australian rules footballers. J. Sci. Med. Sport 12, 503–507. Caslake, M.J., Miles, E.A., Kofler, B.M., Lietz, G., Curtis, P., Armah, C.K., Kimber, A.C., Grew, J.P., Farrell, L., Stannard, J., 2008. Effect of sex and genotype on cardiovascular biomarker response to fish oils: the FINGEN study. Am. J. Clin. Nutr. 88, 618–629. Chatha, S.A.S., Hussain, A.I., Sherazi, S.T.H., Shaukat, A., 2011. Wheat bran extracts: a potent source of natural antioxidants for the stabilization of canola oil. Grasas Aceites 62, 190–197. Chong, M.F.F., Lockyer, S., Saunders, C.J., Lovegrove, J.A., 2010. Long chain n-3 PUFA-rich meal reduced postprandial measures of arterial stiffness. Clin. Nutr. 29, 678–681. Clayton, E., Hanstock, T., Hirneth, S., Kable, C., Garg, M., Hazell, P., 2009. Reduced mania and depression in juvenile bipolar disorder associated with long-chain ω-3 polyunsaturated fatty acid supplementation. Eur. J. Clin. Nutr. 63, 1037–1040. Conroy, R.M., Py€ or€al€a, K., Fitzgerald, A., Sans, S., Menotti, A., De Backer, G., De Bacquer, D., Ducimetiere, P., Jousilahti, P., Keil, U., 2003. Estimation of ten-year risk of fatal cardiovascular disease in Europe: the SCORE project. Eur. Heart J. 24, 987–1003. Cunha, D.C., Crexi, V.T., Pinto, L.A., 2009. Winterization of fish oil with solvent. Food Sci. Technol. 29, 207–213. De Deckere, E., Korver, O., Verschuren, P., Katan, M., 1998. Health aspects of fish and N-3 PUFA from plant and marine origin. Summary of a workshop. Eur. J. Clin. Nutr. 52, 749–753. Deepika, D., Vegneshwaran, V., Julia, P., Sukhinder, K., Sheila, T., Heather, M., Wade, M., 2014. Investigation on oil extraction methods and its influence on omega-3 content from cultured salmon. J. Food Process. Technol. 5, 140–159. Donadio, J.V., Bergstralh, E.J., Offord, K.P., Spencer, D.C., Holley, K.E., 1994. A controlled trial of fish oil in IgA nephropathy. N. Engl. J. Med. 331, 1194–1199. Edwards, R., Peet, M., Shay, J., Horrobin, D., 1998. Omega-3 polyunsaturated fatty acid levels in the diet and in red blood cell membranes of depressed patients. J. Affect. Disord. 48, 149–155. Estrada, J., Boeneke, C., Bechtel, P., Sathivel, S., 2011. Developing a strawberry yogurt fortified with marine fish oil. J. Dairy Sci. 94, 5760–5769. Ganesan, B., Brothersen, C., McMahon, D.J., 2014. Fortification of foods with omega-3 polyunsaturated fatty acids. Crit. Rev. Food Sci. Nutr. 54, 98–114. Harris, W.S., Mozaffarian, D., Lefevre, M., Toner, C.D., Colombo, J., Cunnane, S.C., Holden, J.M., Klurfeld, D.M., Morris, M.C., Whelan, J., 2009. Towards establishing dietary reference intakes for eicosapentaenoic and docosahexaenoic acids. J. Nutr. 139, 804S–819S. Hibbeln, J.R., 1998. Fish consumption and major depression. Lancet, 351–1213. Hill, A.M., Buckley, J.D., Murphy, K.J., Howe, P.R., 2007. Combining fish-oil supplements with regular aerobic exercise improves body composition and cardiovascular disease risk factors. Am. J. Clin. Nutr. 85, 1267–1274. Hooper, L., Thompson, R.L., Harrison, R.A., Summerbell, C.D., Ness, A.R., Moore, H.J., Worthington, H.V., Durrington, P.N., Higgins, J.P., Capps, N.E., 2006. Risks and benefits of omega 3 fats for mortality, cardiovascular disease, and cancer. Syst. Rev. 332, 752–760.

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Huang, T.H., Wang, P.W., Yang, S.C., Chou, W.L., Fang, J.Y., 2018. Cosmetic and therapeutic applications of fish oil’s fatty acids on the skin. Mar. Drugs, 16–256. Hughes, B.H., Perkins, B.L., Calder, B.L., Skonberg, D.I., 2012. Fish oil fortification of soft goat cheese. J. Food Sci. 77, S128–S133. Ismail, A., Bannenberg, G., Rice, H.B., Schutt, E., MacKay, D., 2016. Oxidation in EPA- and DHA-rich oils: an overview. Lipid Technol. 28, 55–59. Javed, A., King, A.J., Imran, M., Jeoh, T., Naseem, S., 2019. Omega-3 supplementation for enhancement of egg functional properties. J. Food Process. Preserv. 43, e14052. Jeyakumari, A., Janarthanan, G., Chouksey, M., Venkateshwarlu, G., 2016. Effect of fish oil encapsulates incorporation on the physico-chemical and sensory properties of cookies. J. Food Sci. Technol. 53, 856–863. Josquin, N.M., Linssen, J.P., Houben, J.H., 2012. Quality characteristics of Dutch-style fermented sausages manufactured with partial replacement of pork back-fat with pure, pre-emulsified or encapsulated fish oil. Meat Sci. 90, 81–86. Khan, F., Elherik, K., Bolton-Smith, C., Barr, R., Hill, A., Murrie, I., Belch, J.J., 2003. The effects of dietary fatty acid supplementation on endothelial function and vascular tone in healthy subjects. Cardiovasc. Res. 59, 955–962. Kolanowski, W., Laufenberg, G., 2006. Enrichment of food products with polyunsaturated fatty acids by fish oil addition. Eur. Food Res. Technol. 222, 472–477. Kris-Etherton, P.M., Harris, W.S., Appel, L.J., 2003. Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Arterioscler. Thromb. Vasc. Biol. 23, e20–e30. Kroes, R., Schaefer, E.J., Squire, R.A., Williams, G.M., 2003. A review of the safety of DHA45-oil. Food Chem. Toxicol. 41, 1433–1446. Kumar, P.P., Krishna, A.G., 2014. Physico-chemical characteristics and nutraceutical distribution of crude palm oil and its fractions. Grasas Aceites 65, 018. Lee, L.K., Shahar, S., Chin, A.V., Yusoff, M., 2013. Docosahexaenoic acid-concentrated fish oil supplementation in subjects with mild cognitive impairment (MCI): a 12-month randomised, double-blind, placebo-controlled trial. Psychopharmacology (Berl) 225, 605–612. Let, M.B., Jacobsen, C., Meyer, A.S., 2007. Lipid oxidation in milk, yoghurt, and salad dressing enriched with neat fish oil or pre-emulsified fish oil. J. Agric. Food Chem. 55, 7802–7809. Linder, M., Fanni, J., Parmentier, M., 2005. Proteolytic extraction of salmon oil and PUFA concentration by lipases. Marine Biotechnol. 7, 70–76. Lopez, A.D., Mathers, C.D., Ezzati, M., Jamison, D.T., Murray, C.J., 2006. Measuring the global burden of disease and risk factors, 1990–2001. In: Global Burden of Disease Risk Factors. vol. 1, pp. 1–14. Margarine, R.F., n.d. Codex Committee on Fats and Oils. McEwen, B.J., Morel-Kopp, M.-C., Chen, W., Tofler, G.H., Ward, C.M., 2013. Effects of omega-3 polyunsaturated fatty acids on platelet function in healthy subjects and subjects with cardiovascular disease. In: Seminars in Thrombosis and Hemostasis. Thieme Medical Publishers, pp. 25–032. McManus, S., Tejera, N., Awwad, K., Vauzour, D., Rigby, N., Fleming, I., Cassidy, A., Minihane, A.M., 2016. Differential effects of EPA versus DHA on postprandial vascular function and the plasma oxylipin profile in men. J. Lipid Res. 57, 1720–1727. Meldrum, S., Dunstan, J.A., Foster, J.K., Simmer, K., Prescott, S.L., 2015. Maternal fish oil supplementation in pregnancy: a 12 year follow-up of a randomised controlled trial. Nutrients 7, 2061–2067. Menegazzo, M.L., Petenuci, M.E., Fonseca, G.G., 2014. Production and characterization of crude and refined oils obtained from the co-products of Nile tilapia and hybrid sorubim processing. Food Chem. 157, 100–104. Milte, C.M., Coates, A.M., Buckley, J.D., Hill, A.M., Howe, P.R., 2008. Dose-dependent effects of docosahexaenoic acid-rich fish oil on erythrocyte docosahexaenoic acid and blood lipid levels. Br. J. Nutr. 99, 1083–1088. Nadeem, M., Imran, M., 2016. Promising features of Moringa oleifera oil. Recent updates and perspectives. Lipids Health Dis. 15, 212. Nadeem, M., Situ, C., Mahmud, A., Khalique, A., Imran, M., Rahman, F., Khan, S., 2014. Antioxidant activity of sesame (Sesamum indicum L.) cake extract for the stabilization of olein based butter. J. Am. Oil Chem. Soc. 91, 967–977. Nadeem, M., Imran, M., Iqbal, Z., Abbas, N., Mahmud, A., 2017a. Enhancement of the oxidative stability of butter oil by blending with mango (Mangifera indica L.) kernel oil in ambient and accelerated oxidation. J. Food Process. Preserv. 41, e12957.

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C H A P T E R

13 Ginger essential oil: Chemical composition, extraction, characterization, pharmacological activities, and applications Jalal Uddina,⁎, Humam Ahmedb,⁎, Yahya Ibrahim Asiric, Ghulam Mustafa Kamald, and Syed Ghulam Musharrafe a

Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, Abha, Saudi Arabia bSilesian University of Technology, Faculty of Energy and Environmental Engineering, Environmental Biotechnology Department, Gliwice, Poland cDepartment of Pharmacology and Toxicology, College of Pharmacy, King Khalid University, Abha, Saudi Arabia d Department of Chemistry, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan eFaculty of Science, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan

13.1 Introduction Essential oils (EOs) are secondary plant metabolites and possess several biological activities. EOs are complex combinations of volatile chemicals taken from the entire plant or a portion of a plant of the same taxonomic origin, such as ginger essential oil (GEO) produced from ginger (Z. officinale Roscoe) (H€ usn€ u Can Bașer and Buchbauer, 2015; Tongnuanchan and Benjakul, 2014). Ginger is a member of the plant family Zingiberaceae, order Zingiberales, and is native to South Asia and East Asia. It is spread to China and parts of Australia, Japan, ⁎

Authors contributed equally.

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00014-1

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Jamaica, Latin America, and Africa (Kumari et al., 2020). Ginger is a medicinally significant fragrant plant native to tropical and subtropical regions. It is made up of 50 genera and around 1500 species of perennial plants, out of which 70–90 are the genus Zingiber (Ravindran et al., 2016). The genus name comes from the Greek term “Zingiberis,” which comes from the Sanskrit word “Shringavera,” which means “deer horn-shaped.” The term “officinale” refers to the plant’s medicinal qualities since it has long been used as a culinary spice and traditional herbal medicine (Shahrajabian et al., 2019). The complex composition of ginger rendered it an essential therapeutic scaffold that includes from a few to several hundred diverse components. The reported study shows that the ginger rhizome contains essential oil (1.5%–3%), starch (6%–20%), fixed oil (40%–70%), ash (9%–12%), protein (3%–8%), fiber (8%), cellulose, water, trace minerals, and saccharides (Gangadharappa et al., 2017; Sˇvarc-Gajic et al., 2017). Ginger has been divided into three major groups: volatile part, non-volatile part, and diarylheptanoids. The essential oil of ginger predominantly contains a volatile compound composed of terpenes (monoterpenes), sesquiterpenes, and their oxygenated products (Kiyama, 2020; Mao et al., 2019). The non-volatile part of the GEO primarily consists of phenolic compounds such as gingerols, shogaols, and paradols. By virtue of these compounds, ginger widely studies for anti-cancer activity (Mahomoodally et al., 2021). These non-volatile compounds are classified into gingerols, shogaols, paradols, zingerones, gingerdiones, and gingerdiols (Ansari et al., 2021; Shahrajabian et al., 2019). Ginger and its extracts are commonly used as a food additive in a variety of victuals. It is valued for its volatile and non-volatile components, such as 6-gingerol, 6-shogaol, 6-paradol, which give it a pungent, spicy, and pleasant aroma, as well as the volatile compounds that give ginger flavor (Menon et al., 2021). The presence of heavy metals in the ginger rhizome is significant because these minerals are interconnected and balanced against each other in human anatomy (Majkowska-Gadomska et al., 2018; Uba et al., 2019). GEO has been commercially recognized across the globe and used in the pharma and food processing industries (Bag, 2018; Kumari et al., 2020). Ginger is used as an important dietary supplements that contributes to the taste and flavor of food and its oil considered as a folk and traditional medicine in different culture such as in traditional Chinese medicines (TCM), Ayurveda, and Tibb Unani (Kiyama, 2020). GEO is recently gaining popularity and attention in the pharmaceutical industry owing to its therapeutic potential in managing several diseases (Mao et al., 2019; Munda et al., 2018). GEO possesses several pharmacological activities including, anti-oxidant (H€ oferl et al., 2015), antiinflammatory ( Jeena et al., 2013), anti-cancer (Mahomoodally et al., 2021), anti-obesity (Ebrahimzadeh Attari et al., 2018), neuroprotective (Choi et al., 2017), cardioprotective (Choi et al., 2017), anti-diabetic (Choi et al., 2017), anti-dengue (Hassan et al., 2021), and anti-emetic (Choi et al., 2017). Additionally, ginger is a potential ingredient functional for food and nutraceutical, due to its products i.e., essential oil and oleoresin (Munda et al., 2018).

13.2 Productions of GEO According to a report (Ginger Oil Market - Forecasts from 2020 to 2025, n.d.), the GEO market is likely to expand at a CAGR (compound annual growth rate) of 9.41% to reach a total market size of USA$ 189.431 million by 2025, increasing from USA$ 110.435 million. This entails the medicinal importance of GEO and its application in different industries such as cosmetics, personal care, food, beverages, and aromatherapy. The worldwide production

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13.2 Productions of GEO

TABLE 13.1 Top 10 ginger producing countries (FAOSTAT, 2019). Sr No.

Countries

Production (tons)

1

India

1,788,000

2

China

1,186,260

3

Nigeria

691,239

4

Nepal

297,512

5

Indonesia

174,380

6

Thailand

166,923

7

Cameroon

83,434

8

Bangladesh

80,234

9

Japan

45,506

10

Philippines

26,929

of ginger is mostly harvested in India followed by China (including the mainland), Nigeria, Nepal, Indonesia, and Thailand (FAOSTAT, 2019). The top 10 ginger-producing countries are shown in Table 13.1 (data fetch from FAOSTAT on 10-08-2021). Production of essential oil depends on several agronomic factors, such as soil type, climate, stresses caused by water and draught, and cultivation practices. Other critical aspects include an accurate understanding of which section of the biomass is used, the location of the oil cells within the plant, harvest time, harvest technique, storage, and processing of the biomass prior to EOs extraction (Nair, 2013). Z. officinale Roscoe requires deep, well-drained sandy, loamy soil enriched in organic matter. The optimum pH of the soil for cultivation is 6.0–6.5. The ginger plant can grow in a hot and humid climate with soil temperature ranges between 25°C and 30°C in an area of annual rainfall between 240 and 300 cm, above 1500 m above sea level. They required partial shade with some filtered sunlight for growth, preferably full shade (Begum et al., 2018a; Mahat et al., 2019; Sommano and Tangpao, 2021). Due to widespread variations in climate, soil characteristics, topography, and the cultivation time of ginger varied across the globe. In most parts of India, ginger is planted from April–June due to rain-fed crops at the arrival of the southwest monsoon season. In Australia, it is grown as an irrigated crop from September to mid-October, whereas in Africa and Jamaica, spring rain plays an important role in the plantation of ginger. Therefore, the crops need regular irrigation, where rainfall is less (Nair, 2019; Vernin and Parkanyi, 2016). Therefore, ginger crops require heavy manuring, and responses of different fertilizers components yield variables amount of ginger crop production. Nitrogen (N), Phosphorus (P), and Potassium (K) as fertilizers were found to be effective individually or in combination with NPK with a variety of organic fertilizers in different ratios to enhance the yield of the crop. In combination with organic fertilizers, these inorganic fertilizers help in improving the macronutrient and micronutrient of the ginger rhizome ( Jabborova et al., 2021; Singh et al., 2016), which indirectly affects the ginger rhizome reflect the chemical composition and yield of GEO.

348

13. Ginger essential oil

Harvesting of ginger also plays an essential role in the crops’ yield and subsequently in GEO production. Ginger crop harvesting depends on the purpose of its use and the economic return of the cultivators. Therefore, the chemical composition of the GEO is vastly affected by agronomics factors and agricultural practices. Typically, ginger takes 8–9 months to attain maturity; however, some farmers harvested it in 6 months before it reached full maturity. This immature and tender ginger rhizome is green and used in pickles, candy preparation, and household use. The peak harvesting time starts from November and continues until January (Nybe and Raj, 2016).

13.3 Chemical composition and yield of GEO Chemical analysis of ginger revealed that there are more than 200 types of components exist, and it is widely divided into three categories such as volatiles, non-volatiles, and diarylheptanoids. The chemical structures of some representatives compounds are given in Fig. 13.1. The yield of GEO from the ginger rhizome is variable from 1% to 3%, depending upon the source of the rhizome. The EOs are also known as volatile oils. Volatile’s fraction is a predominant part of the GEO, approximately (95%–99%) of the total weight of the oil (Liu et al., 2019). It comprises the monoterpenes, sesquiterpenes, and their oxygenated

FIG. 13.1

Chemical structures of major volatile components found in GEO.

13.3 Chemical composition and yield of GEO

349

products. Aldehyde, esters, aliphatic alcohols, and ketones are the other volatile’s constituents of the GEO. These constituents are identified by the analysis of gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS) (Al-Dhahli et al., 2020; Bucur et al., 2020). The volatiles group of the oil contributes to the unique aroma and taste of the GEO (Mahboubi, 2019). The presence of terpenes such as zingiberene, camphene, farnesene, geraniol, β-bisabolene, neral, β-sesquiphellandrene, linalool, α-pinene, citronellal, and borneol are responsible for ginger essential oil’s anti-bacterial and anti-biofilm building action ( Jayasundara and Arampath, 2021). The variation in GEO’s yields and chemical composition is due to the different cultivars and climatic conditions such as harvesting time, region, distillation conditions, and plant’s stage of ripeness (Mahboubi, 2019). In this section, the chemical composition of GEO has been discussed in detail.

13.3.1 Effect of geographical location on chemical components and yield of GEO The study reported 52 volatile components were extracted from the oil of fresh ginger rhizome using the hydro-distillation (HD) technique from Meghalaya, India. These volatiles were predominated by zingiberene, (20.3%), β-sesquiphellandrene (9.4%), (E,E)-α-farnesene, (6.6%), and ar-curcumin (6.3%). The EOs yield was found 0.21% (v/w) on the fresh weight base and the dry weight base were calculated 1.4% (v/w) (Babu et al., 2018). The same ginger species growing in a completely different location of Ghaziabad (India), revealed 80 chemicals in GEO - the most prevalent monoterpenes were citronellyl n-butyrate (19.3%), β-phellandrene (3.7%), camphene (2.6%), and α-pinene (1.1%). The sesquiterpene class was predominant with zingiberene (46.7%), valencene (7.6%), β-funebrene (3.1%), and Selina-4 (14) 7(11)-diene (1%) (Sharma et al., 2016). Another study from North-East India shows the variable yield of GEO, i.e., Arunachal Pradesh (3.3%), Assam (4.17%), Manipur (2.50%), Meghalaya (3.33%), Mizoram (2.86%), Nagaland (3.21%), and Tripura (3.33%) (Kiran et al., 2013). This shows that not only chemical composition but oil yield is also affected by different geographical locations. An investigation on GEO extracted from the air-dried ginger at 25°C yields of 4.07% from China shows α-zingiberene (26%) was the major component followed by β-sesquiphellandrene (8.10%), α-curcumene (7.99%), α-bergamotene (7.99%), β-bisabolene (7.47%), and ar-turmerone (3.86%) (Feng et al., 2018a). Another detailed study on the antioxidant potential and chemical composition of ginger cultivated in south–south Nigeria shows the major type of compound are α-bergamotene with an oil yield of 0.5%. The other principals’ volatile components extracted by Clevenger type apparatus using HD extraction method for 3 h were; α-copaene (10.9%), cadina-1,4-diene (9.1%), α-bisabolol (5.2%), and β-cadinene (5.1%) (Ismaeel and Usman, 2021). The chemical composition and yield of GEO influences with different geographical location in the world, as it impacts by type of soil, climate, and harvesting time. Table 13.2 summarizes the major volatiles constituents of different geographical origins found in GEO with different extraction techniques and rhizome types.

13.3.2 Effect of maturity and variety on chemical components and yield of GEO The effect of maturity, variety, and cultivation location were studied on Sri Lankan ginger cultivars (Rangoon and Sidha). The yield of GEO and chemical composition of the two cultivars were monitored at three maturity stages. This study revealed that GEO yield decrease

350

13. Ginger essential oil

TABLE 13.2 Chemical components and yield of GEO from different geographical location.

Type of rhizome

Extraction method

Yield (%)

Total volatile components identified

Fresh

HD

0.21

52

Dry

HD

4.07

–

HD

Dry

Geographical location

Reference

Zingiberene (20.3), β-sesquiphellandrene (9.4), (E,E)-α-farnesene (6.6), ar-curcumene (6.3)

Meghalaya, India

Babu et al. (2018)

43

α-Zingiberene (26), β-sesquiphellandrene (8.10), α-bergamotene (7.99), α-curcumene (7.99), β-bisabolene (7.47), ar-turmerone (3.86)

Guangzhou, China

Feng et al. (2018a)

–

19

α-Copaene (10.9), cadina1,4-diene (9.1), α-bisabolol (5.2), β-cadinene (5.1)

South–South, Nigeria

Ismaeel and Usman (2021)

HD

3.7

19

Camphene (15), curcumene (9.5), zingiberene (7.1)

Market, Indonesia

Azizah et al. (2019)

Dry

HD

1.38

–

α-Zingiberene (30.21), β-Sesquiphellandrene (13.04), ar-curcumene (10.47)

Chiang Mai, Thailand

Vigad et al. (2021)

Fresh

HD

0.23

15

Zingiberene (41.49), β-phellandrene (9.92), α-citral (9.76), α-curcumene (11.58), camphene (4.6), β-bisabolene (5)

Market, Bangladesh

Nandi et al. (2021)

Dry

HD

0.27

63

α-zingiberene (16.4), citral (10.6), (E,E)-α-farnesene (10.2)

Prana, Brazil

Baldin et al. (2019)

Dry

HD

–

36

α-Zingiberene (27.7), β-bisabolene (7.2), β-Phellandrene (14.7), β-Sesquiphellandrene (8)

Vietnam

Le et al. (2019)

Dry

HD

0.2

30

α-Zingiberene 7.68), β-phellandrene (7.11), ar-curcumene (15.78), β-sesquiphellandrene (6.9), β-bisabolene (7.33)

Al Hasa, Saudi Arabia

Al-Dhahli et al. (2020)

–

–

–

71

α-Zingiberene (17), geranial (10.5), neral (9.1), camphene (7.8), α-farnesene (6.8)

GEO of Ecuador origin purchased in German store

H€ oferl et al. (2015)

Major components (%)

351

13.3 Chemical composition and yield of GEO

TABLE 13.2

Chemical components and yield of GEO from different geographical location—cont’d

Type of rhizome

Extraction method

Yield (%)

Total volatile components identified

Dry

HD

3.36

13

Camphene (13.6), β-phellandrene, (13.6), β-sesquiphellandrene (12.2), geraniol (11.8), α-zingiberene (9.7), α-pinene (8.4)

Makundra, Sri Lanka

Jayasundara and Arampath (2021)

–

HD

–

13

Citral (30.8), zingiberene (17)

Market, Algeria

Meliani et al. (2014)

Major components (%)

Geographical location

Reference

with an increase of maturity stages. Maximum yield of the oil observed at five months (3.36%) maturity and lowest at the eight months (1.6%). Moreover, GEO yield is affected significantly from the location of cultivation and maturity stages, while chemical intensities of the volatile constituents are only affected by the maturity stage. In total, 25 components were detected in two cultivars, where Rangoon was characterized with a variable amount of β-sesquiphellandrene by 10.9% at 5 months and 2.3% at 8 months maturity ( Jayasundara and Arampath, 2021). Another detailed investigation on 10 fresh ginger cultivars from northeast India showed an increase of citral content at 6 months maturity compared to 9 months maturity found in 6 cultivars out of 10 cultivars (Kiran et al., 2013).

13.3.3 Effect of drying methods on chemical components and yield of GEO Different drying methods of the ginger rhizome to extract oil have also affected GEO’s yield and chemical composition. The study confirmed that drying the ginger rhizome at a temperature higher than 70°C prompted the loss of volatile constituents, hence decrease the yields and significantly affect the chemical composition of GEO. Zingiberene is a significant component of GEO found in higher yield (27.8%) in fresh ginger oil, while its intensity decreases to 26.4% at 80°C for 1 h. The same rhizome was subjected to microwave drying yielded 37.1% of zingiberene at 700 W for 2 min, while silica gel dried rhizome yielded 30.2% of zingiberene (Kiran et al., 2013).

13.3.4 Effect of extraction method on chemical components and yield of GEO One Indonesian ginger variety Jahe emprit was studied to evaluate the EOs yield and chemical composition of ginger using different solvent-to-feed (SF) ratios using the HD technique. Gradually increase of the solvent from 0.7:1, 1.7:1, and 2.7:1 was used, and the highest yield of GEO (3.7%) was obtained with an SF ratio of 1.7:1. In total, 19 components were extracted

352

13. Ginger essential oil

from dry ginger-based oil and characterized predominantly with Camphene (15%), Curcumene (9.5%), and Zingiberene (7.1%) (Azizah et al., 2019). These results are different from GEO obtained from Indian (Sharma et al., 2016) and Chinese (Feng et al., 2018a) origin.

13.4 Extraction methods of GEO EOs are liquid extracts from aromatic plants that possess a wide range of uses in several industries. EOs are extracted using a variety of processes, each of which has its own sets of merits and demerits and may be used to determine the biological and physicochemical aspects of the extracted oils (H€ usn€ u Can Bașer and Buchbauer, 2015). Physiochemical characteristics of GEO with accordance of ISO standard 16,928:2014 in different countries are given in Table 13.3. The botanical extract’s properties and components determine the manufacturing process and methodology that used to extract the essential oils. The extraction process utilized is the most crucial factor in ensuring the quality of EOs, since improper extraction techniques can destroy phytochemicals included in aromatic oils and change their function (Aziz et al., 2018). The loss of pharmacological ingredients, stain effect, off-flavor/odor, and physical alteration of EOs are some of the side effects. These methods of extraction are categorized into conventional methods (hydrodistillation, steam distillation, solvent/liquid–liquid, and Soxhlet extraction) and advanced methods (Subcritical extraction liquid, Supercritical fluid extraction, Solvent-free microwave extraction, Microwave-assisted, Microwave hydro-diffusion and gravity extraction) (Ali et al., 2019). The use of sophisticated techniques has enhanced the efficiency of the extraction process in terms of time required for EOs separation and energy dissipation, as well as increased production yield and EOs quality. The production yield, chemical composition, as well as rhizome used, for the extraction of essential oil of ginger by conventional as well as advanced methods are summarized in Table 13.4.

13.4.1 Conventional methods of extraction The conventional methods for the extraction of EOs rely on water distillation using a heating process. TABLE 13.3 Physiochemical characteristics of GEO with accordance of ISO standard 16,928:2014 (ISO Standardization., 2014). Characteristics

China

India

West Africa

Appearance (30°C)

Clear

Clear

Clear

Color

Pale yellow to amber

Yellow

Pale yellow to yellow

Relative density (20°C)

0.873–0.885

0.872–0.890

0.872–0.892

Refractive index (20°C)

1.486–1.495

Optical rotation (20°C)

°

47 and

1.484–1.498 26

°

°

50 and

1.486–1.496 27

°

47° and

18°

353

13.4 Extraction methods of GEO

TABLE 13.4

Comparison of production yield of GEO components obtained from different techniques.

Extraction techniques Extraction conditions

Rhizomes Major condition components %

% Yield of GEO

Steam Distillation

5 h, Ginger:water (1:5)

Dry

Zingiberene (32)

1.2

Kamaliroosta et al. (2013)

Solvent Extraction

24 h, 30°C Ginger: Ethanol (1:3) Dry

Zingiberene (17)

0.38

Oktavianawati et al. (2018)

Soxhlet Extraction

2 h, 100°C Particle size 250 μm

Fresh

–

3

Musa et al. (2021)

Hydrodistillation

130 min, 40°C

Fresh

α-Zingiberene (25.20)

47.95

dos Santos Reis et al. (2020)

MAHD

Power 600 W, 100°C Ginger: water (1:8)

Fresh (dry Zingiberene in dryer) (27.79)

1.71

Argo et al. (2020)

MHG

Power 700 W, 30 min

Fresh

Geranial (30.45)

0.292

Piarasd et al. (2019)

Sc-CO2

20°C, 25 MPa, 3 h

Dry

α-zingiberene (15.90)

1.90

Mesomo et al. (2013)

SFME

Power 640 W, 30 min

Fresh

α-zingiberene (30)

0.25

Shah and Garg (2014)

References

13.4.1.1 Hydro-distillation Hydro-distillation (HD) is one of the simplest and classical methods used to extract EOs from aromatic plants. In this technique, pure water is a key component. EOs are separated by heating plant constituents in the presence of water or another solvent to liquifying the vapors in a condenser. A condenser and a decanter are employed in the system to collect and separate EOs from water (Khan and Dwivedi, 2018). Isotropic distillation is used in the extraction process. In reality, water or any solvent and oil molecules may coexist under atmospheric pressure and throughout the extraction process (heating). HD is a joint process, and it is an alternative form of steam distillation, and it can be utilized in small or large industries. The time needed for distillation is determined by the plant material being treated. Prolonged distillation yields little EOs, but adds up the oxidative products and undesirable high boiling points chemicals (Azizah et al., 2019; dos Santos Reis et al., 2020). The Clevenger apparatus used in HD gives better purification of oil. Moreover, this technique is cheap and simple in operation. Apart from these advantages, HD generates more waste during processing, and it has a longer extraction time than other techniques. Also, HD can alter the chemical composition of EOs (Gavahian et al., 2012). The EOs extracted by HD from three different regions of India have been studied. It has been found that oil contains zingiberene as a significant constituent. Among these oils, the GEO from the Majhauli region contains the highest amount of zingiberene (16.6%), subsequently (E)-citral (12.0%), camphene (7.6%), (Z)-citral (8.8%), and ocimene (6.5%) (Raina et al., 2013). The first reported work on the Sikkim cultivar from two geographical locations of India (Bhaisa and Majhauli) contains 60 constituents representing 94.9% and 92.6% of EOs of ginger, respectively. Surprisingly, geranyl acetate, zingiberene, and geranial were the primary components in Bhaisa oil,

354

13. Ginger essential oil

whereas zingiberene (19.8%) and g ranial (8.2%) were the major compounds in Majulay oil (16.5%). The Bhaisa oil showed a g eater concentration of oxygenated molecules than other ginger cultivar oils (43.1%) (Sasidharan et al., 2012). 13.4.1.2 Steam distillation Steam distillation (SD) is one of the oldest and most commonly used techniques for processing ginger to obtain its oil. It has numerous benefits, including being an active antibacterial and having antioxidant properties. In SD, the plant material in an alembic is subjected to steam without being soaked in the solvent (water). The steam is generated from a steam generator, which results in a breakdown and release of aromatic compounds or essential oil. The main idea behind this method is that when the combined vapor pressure reaches about 100°C, it matches the ambient pressure, allowing volatile components with boiling points ranging from 150°C to 300°C to be evaporated at temperatures close to those of water. Furthermore, depending on the complexity of EOs extraction, this process can be performed under pressure (Aziz et al., 2018). Gavahian (Gavahian et al., 2012) created a unique SD extraction methodology to boost isolated essential oil yields while, minimizing the reduction of wastewater during the extraction process. The technique employs a densely packed bed of plant samples placed over the steam source. Only steam is permitted to flow through the plants, and boiling water is not to combine with the botanical elements. Therefore, the process needs less amount of water and steam in the distillate can be reduced. SD is one of several techniques for extracting EOs from ginger. In a reported study, the optimal operating condition was discovered to be 0.35 mL/S as the steam flow rate, which yielded 2.4% of GEO. The optimal time for the procedure was anticipated to be 7.5 h. The oil’s composition changed depending on the steam flow rate, and each steam flow rate had its primary component in the oil (Fitriady et al., 2017). In another study, SD techniques were used to extract EOs of ginger from Guinean and Chines variety with 90 components identified, where zingiberene was a primary compound with 19.89% and 31.1%, respectively. The results show that the effect of SD process increases the monoterpenes alcohols and terpenes hydrocarbons (Toure and Xiaoming, 2007). In a reported study, EOs yield extracted with this technique found 5.10%, with carvone being the major compound (18.70%) (Hussein, 2018). SD is an eco-friendly and green technique, and it can be modified with other advanced techniques to increase GEO yield. However, this technique consumes a lot of raw materials and is a time-consuming as well as costly method for the extraction of GEO. 13.4.1.3 Solvent extraction/liquid–liquid extraction Solvent extraction or liquid–liquid extraction technique used for separation of a compound from its constituents based on the solubility. In this technique, the plant samples are combined with solvents to be extracted, and the combination is slightly heated before the solvents are filtered and evaporated. The filtrate contains a wax or a resin (resinoid), fragrance, and EOs combination. After combining alcohol with the filtered mixture to dissolve the EOs, it is filtered at a low temperature. Throughout the distillation process, the alcohol absorbs the aroma and evaporates, leaving the fragrant absolute oil in the pot residue (Ren et al., 2011). In a previously proposed study, the liquid–liquid extraction results in an ethyl acetate fraction containing 6-gingerol. Given its 6-gingerol concentration, which prevents lipid

13.4 Extraction methods of GEO

355

peroxidation and other inflammatory illnesses, the ethyl acetate fraction recovered from distillation leftovers has the potential to be developed as an antihyperlipidemic medication based on antioxidant capacity and anti-inflammatory characteristics. The suggested approach also allows for the continued use of red ginger distillation leftovers in the food industry. Because of its antioxidant activity, the ethyl acetate fraction produced from this residue might be used as a preservation agent in the future. However, this process for extracting EOs is more complex than other techniques, making it time-consuming and costly (Suciyati et al., 2021). A study reported that GEO extraction by liquid–liquid extraction in combination with EDTA improved the quality of EOs due to its chelating effects. The level of zingiberene has been increased using EDTA (Sari, 2017). Another report suggests using pressurized liquid extraction (PLE) to extract bioactive compounds from ginger. The extract of PLE revealed a well-defined chemical composition of ginger extract using 70% ethanol as a PLE solvent. The maximum yield of gingerols compounds was achieved at 1500 psi for 20 min at 100°C (Hu et al., 2011). 13.4.1.4 Soxhlet extraction Soxhlet extraction technique was developed in 1879 by Franz Von Soxhlet. Initially, it was created to extract lipids from solid materials. This extraction method uses solid–liquid contact to remove one or more chemicals from a solid by fractionalization into a refluxing liquid phase (Lo´pez-Basco´n-Bascon and Luque de Castro, 2020). The sample is continuously mixed and extracted with fresh parts of the solvent is one of the advantages of this technique. Moreover, this process halts the possibility of the solvent getting saturated with the material’s extractable components. Furthermore, the system’s temperature is close to the boiling point of the solvent and surplus energy in the form of heat aids in improving the extraction kinetics of the system. SE technique has few drawbacks, including the fact that the process takes lot of time (hours or days) to complete; the material is diluted by greater amount of solvent, and losses occur due to volatilization and thermal degradation (Bryda and Stadnytska, 2021). A study on GEO extraction by Soxhlet extraction method utilizing various solvents such as acetone, ethanol, water, and n-hexane was published, and it was discovered that n-hexane offers a higher yield (19.4%) than other solvents (Lemma and Egza, 2019). The best circumstances for the soaring oil production yield (3.10%) and the greater concentration of 6-gingerol in GEO (20.69%) were obtained using supercritical fluid extraction at 15 MPa, 35°C, and 15 g/min (Salea et al., 2017).

13.4.2 Advanced methods of extraction of GEO The modification of existing extraction procedures is due to the numerous drawbacks of conventional procedures that promote EOs to endure chemical changes such as hydrolysis, isomerization, and oxidation. The conventional techniques use high temperatures, which reduce the quality of EOs while also lengthening the extraction time. Innovative techniques are designed to keep the oil’s chemical components and natural proportions in their original condition to overcome these problems. New extraction procedures must consider characteristics

356

13. Ginger essential oil

such as energy consumption, solvent utilization, extraction time, and carbon dioxide emissions (Aziz et al., 2018). 13.4.2.1 Supercritical CO2 extraction The method for extracting one component (Extractant) from the fluid matrix using supercritical fluids is known as supercritical-CO2 extraction (Sc-CO2). Sc-CO2 extraction is based on the critical fluid temperature (Tc) and critical fluid pressure (Pc). Fluids with these essential characteristics exhibit intriguing features such as high diffusivity, low viscosity, and density closer to liquids. The solvent used for the extraction of EOs in supercritical fluid extraction is CO2 due to its low Pc (72.9 atm) and Tc (31.2°C) (Yousefi et al., 2019). Recently, Sc-CO2 technique combined with online fractionation of dry ginger carried out in a multiple separator setup yielded 5.95% oleoresin of 96.15% pure and contained 51.2 wt% of main actives compounds in separator 1, operating at 175 bar/40°C. At the same time, 2.71% of volatile oil (95.94% pure) was collected in separator 2 (40 bar/40°C). In addition, the optimum conditions on a laboratory scale (40°C, 276 bar, and ginger particle size 253 μm) give a mixture extract with 37.97 wt% main actives compounds and 28.3 wt% volatile oil yielded 8.6%. These parameters were scaled up 50 times on a commercial level machine later in the process. The recovered mixed extract enhanced its yield by 0.1% while boosting its major active ingredients and volatile oil by 0.34 and 1.2 wt%, respectively (Shukla et al., 2019). Sc-CO2 extraction is a low-carbon, long-term method of extracting high-purity oil with a high aromatic component concentration. This method has a beneficial impact on GEO yield. α-zingiberene, α-farnesene β-sesquiphellandrene, β-bisabolene, and α-curcumene are the major volatiles constituents of GEO extracted by Sc-CO2. The same research team also compared extract obtained from Sc-CO2 and propane as a solvent revealed that total antioxidant activity increase from the extracts obtained with Sc-CO2. Apart from this, due to the reduction of extraction time and solvent-free residues, Sc-CO2 is considered the best extraction method compared to the conventional methods (Mesomo et al., 2013). 13.4.2.2 Subcritical water extraction The subcritical water extraction (SWE) process is regarded the finest alternate approach as it allows faster isolation of EOs from the plant material, performed at a low temperature. SWE is an easy, inexpensive, and ecological friendly technique. A broader range of extracted compounds and a higher yield of selective components make it a popular method of choice for ginger to extract oil. In SWE, the extraction time is about 15 min compared to the 3 h of other conventional methods. The essential oil extracted by this method has more significant characteristics, like a great quantity of oxygenated components without the presence of terpenes. Furthermore, this method allows for significant cost savings in energy and plant materials (Sˇvarc-Gajic et al., 2017). Different SWE extraction was applied to maximize the content of 6-shogaol and 6-gingerol from pulp and peels of ginger. The highest yield was obtained from the ginger pulp with 0.68 and 0.39 mg/g. An elevated amount of 6-shogaol were observed as temperature and extraction time increase, due to thermal cracking of 6-gingerol into 6-shogaol (Ko et al., 2019). The ginger rhizome extract obtained from SWE was evaluated compared to extract obtained by boiling water at ambient pressure. The extract obtained from both methods

13.4 Extraction methods of GEO

357

was evaluated for antimicrobial and cytotoxicity activity. The study concludes that SWE extract exhibited better results in both in vitro assays (Sˇvarc-Gajic et al., 2017). 13.4.2.3 Solvent-free microwave extraction Solvent-free microwave extraction (SFME) is based on a combination of two different methods: heating plant components with microwave, afterward, dry distillation under the atmospheric pressure of the plant in the absence of any solvent (Yingngam and Brantner, 2018). In this method, the sample is irradiated at 700 W for 70 min to provide the best SFME process conditions. The greatest significant influence on oil recovery was exerted by microwave power (P < 0.001), followed by the irradiation duration (P < 0.01). The most abundant volatile components in the oil obtained under ideal conditions were sabinene, terpinen-4ol, and terpinen-4-ol in greater quantity than HD. SFME is considered a green technique used for the extraction of EOs from aromatic and medicinal plants. Isolation of GEO by using SFME technique results in complete extraction with higher plant cell is rapid compared to HD (Yingngam and Brantner, 2018). In another detailed investigation based on factorial design to determine the optimized SFME extraction condition. The results show major factor that influenced the oil yield was extraction time, followed by the sample type and microwave power level. This study (Shah and Garg, 2014) concludes the optimized condition using SFME were; extraction time 30 min, 640 W microwave power, and crushed sample to be used, which is different from another published study (Yingngam and Brantner, 2018). 13.4.2.4 Microwave-assisted hydro-distillation Microwave-assisted hydro-distillation (MAHD) utilizes a microwave oven to extract active components of the ginger plant. It is considered as one of the advanced techniques based on the dielectric constant of the water as a solvent and the sample. MAHD is regarded as an important and alternative method of extraction of GEO due to its advantages, such as the reduced time, less solvent, controllable heating process, selectivity, and volumetric heating (Argo et al., 2020). In this technique, the heating principle is depending on the polar materials directly and command over two phenomena that is dipole rotation and ionic reduction, which occurs instantaneously in most of the cases. In situ, the solvent-free MAHD technique for extraction of GEO from ginger rhizomes was carried out in a TE10n single-mode microwave cavity with a changeable power 2 kW generator running at 2.45 GHz. The best processing parameters for the entire ginger root were determined to be 1000 W (0.40 kWh/kg) for 5 min, yielding 0.35 g oil/100 g plant. This was compared to a standard HD method yield of 0.2 g/100 g plant in 150 min and a multi-mode microwave cavity-based hydro-distillation yield of 0.3 g/100 g plant in 90 min (Racoti et al., 2017). 13.4.2.5 Microwave hydro-diffusion and gravity Microwave hydro-diffusion and gravity (MHG) is a newly developed green approach to extract EOs from ginger plant. This environmentally friendly extraction process is a one-ofa-kind microwave combination of microwave heating and earth attraction at atmospheric pressure. MHG was created for both experimental and production scale applications for extracting EOs from ginger (Asofiei et al., 2017).

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As reported in a previous study, the yield of GEO isolated by MHG is low as compared to HD method. Still, this technique has been proven to be more efficient in terms of time, and it generates a minimum amount of waste. Furthermore, because its high concentration of monoterpene and oxygenated components, the EOs produced via MHG extraction were shown to be more active in anti-bacterial activity. Secondly, this redesigned rotatable equipment, which was readily constructed from a low-cost household microwave oven to assure evenly dried product, might be deemed scientifically thrifting practical for small-scale deployment (Nguyen et al., 2019). MHG has emerged as not only economical and efficient but also environmentally friendly, as it does not require solvent or water and uses less energy. The performance and benefits of this approach include a reduction in extraction time (HD takes 90 min or more, whereas this process takes only 20 min), a reduction in environmental impact, and electricity savings (Piarasd et al., 2019).

13.5 Analytical method for characterization of GEO Chemical composition of GEO comprises mainly terpenes, sesquiterpenes, and their oxidative product, along with ester, aldehyde, and ketone. These compounds have complex and diverse structures; therefore, the choice of the analytical method to characterize the GEO has become crucial. These analytical are divided into a classical method and advanced method of analysis. The earliest techniques focus mainly on the quality aspect (physicochemical properties), identity and purification of GEO (H€ usn€ u Can Bașer and Buchbauer, 2015; Jankowski, Jens-Achim Protzen, 2020). The common physiochemical properties monitored for quality control of GEO are specific gravity, relative density [ρ]T(ºC), optical rotation [α]20 D , refractive index [ɳ ]20 , solubility or immiscibility and physical appearance of the ginger oil (Nandi D et al., 2021). Table 13.5 summarized some standard physicochemical properties of Chinese, Indian and West African essential oil extracted from ginger using official methods of international standards organization (ISO) Geneva, Switzerland (ISO Standardization., 2014). The majority of EOs analysis methods depends on chromatographic processes that allow component separation and identification. However, further confirmatory data is necessary for accurate identification to prevent ambiguous characterizations. In this section, we briefly discussed the two most used analytical techniques for the identification and characterization of GEO.

13.5.1 GC–MS analysis of GEO The chemicals to be studied in gas chromatography (GC) are vaporized and eluted through the column by the pressure of mobile (carrier gas) phase. Analytes are sorted depending on their vapor pressures and affinity for the fixed bed. Generally, compounds with high vapor pressure and has low solubility in the stationary phase are strongly influence by the moving carrier gas, hence will emerge first from the column first (short retention time), while compounds those have lower vapor pressure and has high solubility in the stationary phase expected to influence less likely by the moving carrier gas, hence will have a longer retention

359

13.5 Analytical method for characterization of GEO

TABLE 13.5

The pharmacological activities of oil extracted form ginger.

Bioactivities

Active components (%)

Antimicrobial

Antioxidant

Study Model

Method

γ-Eudesmol

In vivo

Resazurin >250 μg/mL >250 μg/mL microtiter assay Plate broth microdilution

Citral (geranial 10.5 and neral 9.1), α-zingiberene (17.4), camphene (7.8), α-farnesene (6.8) and β-sesquiphellandrene (6.7)

In vitro

Antiinflammatory Zingiberene (31) ar-curcumene (15.4) sesquiphellandrene (14.0) Anticancer

In vivo In vivo

α-Zingiberene (52.35), In β-pinene (14.20) and vitro β-sesquiphellandrene (12.11)

MTB NTM

ABTS•+ DPPH• BHT Saccharomyces cerevisiae

Dose

3.94 μg/mL 675 μg/mL 4.41 μg/mL

Baldin et al. (2019)

H€ oferl et al. (2015)

___________ ________

Carrageenan-induced Carrageenan 0.02 mL paw edema (Balb/c Dextran 0.02 mL mice) Human ovarian cancer cell lines HO-8910 and human hepatocellular liver carcinoma cell line Bel-7402

References

MTT assay HO-8910 (GEO)

Jeena et al. (2013)

Wang et al. 0.00547 mg/mL (2012) 0.00218 mg/mL

Bel-7402 (GEO)

Anti-viral

Zingiribene (32.1), In CpHV-1 α-curcumene (15.2), vitro β-sesquiphellandrene (10.91), α-farnesene (7.23), camphene (4.74) and α-phellandrene (4.35)

Virucidal 55.84 μg/mL activity assay

Camero et al. (2019b)

Antineoplastic

Citral (17.25), δ-citral In (10.25), camphene vivo (9.55), α-zingiberene (7.57), nerol (6.37) and phellandrene (6.83)

Fauldfluor 33 μL/100 g (LIBBS) 5-Florouracil (5-FU)

De Lima et al. (2020)

Antifungal

α-Zingiberene (23.85) and geranial (14.16)

150 μg/mL

(Nerilo et al., 2016)

Colorectal region of Wistar rats

In Aspergillus flavus vitro

Aflatoxin extraction (AFB1 and AFB2

time. Furthermore, coupled gas chromatography–mass spectrometry (GC–MS) is widely known for its capacity to detect volatile compounds in very complex taste and fragrance samples. The information value of the large quantities of data generated by GC–MS equipment was extensively exploited following the development of sophisticated data collecting and

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processing systems, including automatic library search algorithms. The most common and easy technique in GC–MS identification is to compare the acquired unknown mass spectra to those in a reference MS library (H€ usn€ u Can Bașer and Buchbauer, 2015). The various investigations were carried out utilizing the GC, GC–MS, and chromatographic processes. GEO contains the active chemicals zingiberene, citral, ar-curcumene, β-bisabolene, camphene and geranial. The GC–MS oil study revealed a high concentration of oxygenated chemicals (Munda et al., 2018). Another study revealed that geraniol (25.52%) was found to be the most abundant element of GEO, followed by (Z)-citral, eucalyptol and camphene with yield of (13.3%), (9.19%), and (6.17%), respectively. The other with minor with compounds including α-pinene, β-myrcene, linalool, (E)-citral, neryl acetate, α-zingiberene, curcumene, β-sesquiphellandrene, α-amorphene, and farnesene. GEO can be utilized in a variety of ways rely on the activities of its synthetic components (Begum et al., 2018b). An investigation was conducted to extract EOs from dried ginger from the region of Ankara, Turkey. GC–MS analysis revealed that zingiberene was found in abundance (16.32%), followed by curcumene (12.42%) and sesquiphellandrene (11.40%), while acoradiene (3.00%), camphene (2.92%), and eucalyptol (2.48%) were present in the lowest quantities (Şener et al., 2017).

13.5.2

13

C NMR analysis of GEO

In some specific cases, the information obtained from GC–MS is not sufficient to characterize GEO. Therefore, an additional analytical technique is required to elucidate the structure of the isolated components from GEO. In this regard, Nuclear magnetic resonance (NMR) spectroscopy gives very important and detailed information about the structure, dynamics, chemical environment, and reaction states of the molecules. 13C NMR, unlike 1H NMR is not sensitive, but provides crucial information of the adjacent carbon in a molecule with similar small functional groups along with different neighboring substituents (Speight, 2017). 13C NMR offers a great deal of advantage for characterizing the EOs by solving a certain problem more easily as compared to other physical or physiochemical method. The ability to identify and characterized the components without separation into individual components, certainly is the most important trait of 13C NMR. Moreover, information about molecular structure and surrounding functional group can be directly extracted from chemical shift values. Z. officinale roscoe is well known for its medicinal properties. Its active constituents such as polysaccharide, 6-shogaol, 8-shogaol, 10-shogaol and 1-dehydro-4-hydroxy-6-gingerdione possess anti-aging, anti-tumor, anti-microbial, and anti-pyretic activities. A study on albinos’ rats for the investigation of antipyretic activity revealed that the 13C NMR spectra showed 84 carbon peaks, indicating the presence of mixture of similar four compounds. The rhizome of Z. officinale Roscoe was studied to discover four distinct components using current spectroscopic methods (2D-NMR) and to determine the powerful antipyretic and anti-bacterial properties. These compounds’ structures were determined to be 6-shogaol, 8-shogaol, 10-shogaol, and 1-dehydro-4-hydroxy6-gingerdione (Myint and Khine, 2007). Lee and his co-workers identified that 6-shagol isolated from GEO by comparison of its NMR data with reported values for its anti-aging activity in Caenorhabditis elegans, a commonly utilized model organism for human aging research, the lifespan-extension effect of 6-shogaol was demonstrated in a dose-dependent manner (Lee et al., 2018).

361

13.6 Pharmacological activities of GEO

Another study reported 13C NMR characterization (molecular weight and chemical composition) of ginger polysaccharides in the form of glycosidic linkage, affects the anti-tumor activity of five types of purified polysaccharides (HGP, EGP1, EGP2, UGP1, and UGP2) and three types of crude polysaccharides (HCGP, ECGP, and UCGP) on five types of tumor cells (H1975, Hela, HCT116, B16, and MCF-7). It has been found that the polysaccharide HGP, UGP2 (high molecular weight), and EGP1 (low molecular weight) have no significant antitumor activity as compared to EGP2, UGP1 (middle molecular weight) (Liao et al., 2020).

13.6 Pharmacological activities of GEO GEO extracted from the ginger rhizome contain several biologically active compounds with many health benefits. Although, the chemical compositions of GEO are influenced by a variety of variables, such extraction method, cultivars, time of harvesting and location of cultivation which in turn also impact the various pharmacological and biological activities of GEO as shown in Fig. 13.2. Different pharmacological activities of GEO in the literature are summarized in Table 13.5.

Anoxidant

Anmicrobial

Anulcer

Anoxidant

Immunomodulatory

Neuroprotecve

Bronchodilator

Ancancer

Andiabec

Anobesity

FIG. 13.2 Pharmacological activities of GEO.

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13. Ginger essential oil

13.6.1 Antioxidant activity The phenolic compounds such as gingerols, zingerone, and shogaols are the main constituents that elicit the antioxidant activity of ginger rhizome extract (Li et al., 2016). Several reports showed that GEO has high antioxidant activity (Adaramola and Onigbinde, 2017; Jeena et al., 2013). The antioxidant activity of GEO is tested by both in vitro and in vivo methods. In vitro, it has been tested using ferric-reducing antioxidant power (FRAP), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and 2,20-azinobis-(3-ethylbenzothiazoline-6-sulfonicacid) (ABTS) assay. While in vivo, Fe (III) chelation by GEO is established using Saccharomyces cerevisiae. Excessive superoxide (O2 ) can decrease Fe (III) via the Haber-Weiss reaction, and the Fe2+ can then participate in the Fenton reaction with H2O2, resulting in the production of OH° (H€ oferl et al., 2015). Another in vitro study found that Chinese GEO demonstrated antioxidant activity with an IC50 of 110.14 mg/mL. The comparable EC50 values for ascorbic acid were 0.025, 0.005, and 0.478 mg/mL, respectively, while for quercetin, it is 0.017, 0.002, and 0.078 mg/mL. In the ABST test, GEO also shown antioxidant activity. The radical scavenging activity was found 0.87–869.2 mg/mL of GEO for positive control of ascorbic acid (Bellik et al., 2013). Furthermore, GEO has a DPPH• scavenging action produced by SD extraction, which is demonstrated with molecular distillation. Another in vitro study, the EC50 was 10 mg/mL (Gan et al., 2016). An intra-peritoneal infusion of GEO scavenged superoxide and hydroxide radicals while also inhibiting tissue lipid peroxidation. In macrophages, about 250 mg/kg GEO inhibited 18.25% phorbol 12-myristate 13-acetate (PMA), thus induced superoxide radicals. Contrast to the control group, oral treatment of 100 or 200 mg/kg of GEO for 30 days enhanced antioxidant enzymes such as superoxide dismutase, catalase, glutathione, and glutathione reductase in blood. The levels of glutathione peroxidase, superoxide dismutase, and glutathione-s-transferase in the liver were raised by GEO ( Jeena et al., 2013). The findings of the research revealed that GEO has a function in shielding cells from extracellular detrimental radicals by boosting liver and serum antioxidant enzymes.

13.6.2 Anti-inflammatory and analgesic effects In a streptococcal cell wall-induced rheumatoid arthritis model in female Lewis’ arthritis, EOs from ginger were evaluated for anti-inflammatory effects. A daily intraperitoneal injection of 28 mg/kg GEO decreased chronic joint inflammation while having no effect on acute joint inflammation or the formation of granulomas at the site of streptococcal cell wall deposition in the liver. GEO serves as a phytoestrogen with little effects on estrogen target organs in vivo (Funk et al., 2016). GEO inhibited Herpes Simplex Virus-2 (HSV-2) replication in vitro, stopping plaque formation by 90%, and GEO’s anti-infective efficacy against CpHV-1 (Caprine herpesvirus 1) was tested in MDBK (Madin-Darby bovine kidney) cells. Results showed that GEO did not affect CpHV-1 replication or adsorption. Furthermore, ginger oil completely inactivate cell-free CpHV-1 (Camero et al., 2019a). Another study reported that on chemically induced cutaneous inflammation, GEO exerts an anti-inflammatory and protective action. In vivo research study revealed that GEO substantially reduced the gene expression of inflammatory cytokines in auricular tissues such as Toll-like receptors (TLR-2 & 4), Tumor necrosis factor

13.6 Pharmacological activities of GEO

363

(TNF), interleukin-1 and 8 (IL-1 and 8) while increasing the gene expression of cytokine interleukin-4 (IL-4) (Xu et al., 2019). The analgesic properties of GEO were conducted in mice using the hot plate and writhing assays. In the hot plate and writhing tests, GEO’s 0.25–1 g/kg exhibited significant analgesic effects. The writhes were decreased by (64.3%) with 1 g/kg of GEO compared to (81.3%) with indomethacin (0.01 g/kg). In the hot plate test, 1 g/kg of GEO induced a prolonged latency time of (243.1%) compared to (274.5%) for indomethacin ( Jeena et al., 2013). The impact of GEO on leukocyte chemotaxis in vitro revealed that GEO administration reduced leukocyte movement toward casein stimuli. Dexamethasone pretreatment inhibited casein-induced leukocyte migration. A decrease in the number of rolling, adhering cells, and migrating leukocytes was seen after oral pretreatment of carrageenan-injected mice with 200 or 500 mg/kg of GEO. These effects were equivalent to 5 mg/kg indomethacin (Nogueira De Melo et al., 2011).

13.6.3 Antimicrobial activity Antimicrobial resistance has posed a significant threat to the spread of bacterial, contagious, and viral infections. A few herbs and flavors have been created as common effective antimicrobial effects against numerous pathogenic microorganisms. For a long time, GEO has been reported to be antibacterial, antifungal, and anti-viral (Moon et al., 2018; Nerilo et al., 2016). In the anti-bacterial assessment of GEO against Gram-negative bacteria, inhibition area widths of 11.5, 6.6, and 10 mm were found against Escherichia coli (ATCC 25922), Acinetobacter baumannii (ATCC 19606), Pseudomonas aeruginosa (ATCC 27853), and 30 multidrug-resistant (MDR)-A. baumannii. GEO exhibits MIC50 and MIC90 values of 2 and 4 mg/mL, respectively, against MDR-A. baumannii. The matching MBC concentration was 4 mg/mL. In this investigation, tea tree essential oil was utilized as a positive control, with MIC and MBC values 2 and 4 mg/mL, separately (Intorasoot et al., 2017). Thus, GEO appears to have more anti-bacterial action against Gram-positive bacterium than Gram-negative bacterium. Furthermore, the antimicrobial properties of GEO revealed that the chemical makeup of GEO influences these activities. GEO was found to have anti-dermatophyte properties against Trichophyton rubrum and Microsporum gypseum. In addition, the interactive benefits of Curcuma longa and GEO opposed to T. rubrum and M. gypseum were verified (Sharma and Sharma, 2011). The GEO from fresh rhizome of ginger containing citral (21.7%) and zingiberene (23.9%) inhibited Fusarium verticillioides with a MIC value of 2.5 mg/mL. Ergosterol production oscillated after being exposed to 0.5–3 mg/mL of GEO, and ergosterol synthesis was reduced at higher doses of GEO (57%–100%). GEOs reduced the synthesis of fumonisins B1 and B2. The suppression of ergosterol biosynthesis and fumonisin production is linked with a decrease in fungal biomass. GEO also reduced fungus cytoplasmic levels and disrupted membrane integrity (Yamamoto-Ribeiro et al., 2013). The occurrence of 48 bioactive constituents in the extract of ginger rhizome shown bactericidal properties against 6 microorganisms. Bactericidal action was attributed to naphthalenamine decanal and copaene, according to the findings (Shareef et al., 2016). In vitro study revealed that GEO efficiently inhibits Fusarium verticillium growth by decreasing ergosterol production and altering membrane integrity and eliminating the making of fumonisin B1 and fumonisin B2 (Yamamoto-Ribeiro et al., 2013). Furthermore,

364

13. Ginger essential oil

GEO has the effect of inhibiting the growth of Aspergillus flavus and the production of aflatoxin and ergosterol (Nerilo et al., 2020). Another study concludes, citral and γ-terpinene and in GEO showed effective antifungal properties against A. flavus and reduces gene expression were found related to aflatoxin biosynthesis (Guirguis, 2020).

13.6.4 Anticancer activity One of the dominant death causes is reported so far is cancer. The global cancer statistic confirmed that about 19.3 million new cases have been reported in 2020 across the globe (Sung et al., 2021). Many studies show that natural products of plant origin possess anticancer properties. Lately, it is dig up that the ginger and its essential oil plays a crucial role against the different kind of cancer (cervical, breast, and prostate) (El-Ashmawy et al., 2018). GEO has cytotoxic effect against cancers, including breast cancer (Salihah et al., 2016a), cervical cancer (Zhang et al., 2017), liver cancer (Lai et al., 2016), and pancreatic cancer (Akimoto et al., 2015). In vitro study showed that the growth of HeLa human cervical adenocarcinoma cells could be inhibited by 6-gingerol and induce cell cycle arrest in G0/G1 phase by reducing cyclin A and cyclin D1 protein levels (Zhang et al., 2017). In ginger extract, the anti-proliferation activity of three bioactive components (6-gingerol, zingerone, and sesquiterpenes) was investigated on a number of cancer cell lines. Cytotoxicity was found for all three drugs in the tests, with 6-gingerol exhibiting the highest antiproliferation activity in the A549, HepG2, and MDAMB-231 cell lines (Wang et al., 2020). The anticancer properties of GEO were also investigated for HeLa, SiHa, MCF-7, and HL-60 cell lines, the IC50 values for 46.2–172 g/mL of α-zingiberene, one of the major components of GEO, were 60.6, 46.2, 172, and 80.3 g/mL, respectively. In SiHa cells, zingiberene induced nucleosomal DNA breakage, a rise in the proportion of sub-diploid cells, death, and activation of caspases. The IC50 values of GEO containing α-zingiberene (35.0%), ar-curcumene (15.3%), and β-sesquiphellandrene (12.3%) against cell lines were 38.6–82 g/mL. The GEO with the lowest IC50 was SiHa (38.6 g/mL) (Lee, 2016). These studies showed that overall, GEO exhibited strong protection against cancerous cells.

13.6.5 Neuroprotection In older individuals, the primary risk factors are neurodegenerative illnesses like Parkinson’s and Alzheimer’s. Up to date, studies show that ginger and its constituents is one of the potential candidates for the management and treatment of neurodegenerative diseases. According to studies, oxidative stress and inflammation are variables that contribute to a variety of diseases because oxidative stress can change proinflammatory cytokines and reduce cellular antioxidant capability. Cell development, differentiation, and death may be hampered as a result of increased oxidative stress, potentially leading to disease etiology (Mohd Sahardi and Makpol, 2019). The two active components of ginger (6-gingerol and 6-shogaol) helped prevent oxidative stress and inflammation (Choi et al., 2018, 2017). Farnesene is one the component in GEO showed in vitro neuroprotective effect on Alzheimer’s disease (AD) model. Briefly, β-amyloid protein was used to induce AD cytotoxicity in SHSY-5Y (human neuroblastoma cell line). Farnesene is an active component of GEO

13.6 Pharmacological activities of GEO

365

and was applied on cell culture lines in different doses (1.625–100 μg/mL) for 24 and 48 h to investigate the neuroprotective effect. The use of farnesene in cell cultures resulted in a substantial reduction in necrotic deaths, by the Hoechst 33258 fluorescence staining technique. Furthermore, study concludes that farnesene might reduce necrotic cell death up to threefold caused by β-amyloid exposure (Arslan et al., 2021).

13.6.6 Anti-obesity activity Obesity is connected to a number of chronic illnesses, including hypertension, diabetes, and cardiovascular disease (Leggio et al., 2017). Recent studies show that ginger may affect gastric motility, appetite and therefore, several studies were subjected to zingiber officinale Roscoe role in treating and preventing obesity (Ebrahimzadeh Attari et al., 2018; Wang et al., 2017). It is reported that, gingerenone A, a polyphenol in ginger extract inhibited adipogenesis and lipid accumulation more effectively than gingerols or 6-shogaol in 3T3L1 preadipocyte cells. In vivo, gingerenone A showed to regulate fatty acid metabolism by activating AMPK, and reducing diet-induced obesity (Suk et al., 2017). Further studies revealed that the biologically active ingredients of the ginger, including gingerenone A, 6-gingerol, and 6-shogaol have anti-obesity activity, and their mechanism is primarily related to inhibiting the production of fats and enhancing the catabolism of fatty acids (Ebrahimzadeh Attari et al., 2018). Another investigation showed the synergetic antihyperlipidemic effect of GEO with nanoemulsion of lovastatin in the high-fat diet (HFD) Wistar rats (Faran et al., 2019). The ginger extract containing 5.2% gingerols supplemented orally (400 mg/Kg/day) for 35 days showed a decrease in serum triglycerides and improved the insulin sensitivity in HFD without changes in body weight, which indicate GEO can act as an adjuvant in obesity treatment (Luciano et al., 2020). GEO and its major components citral were supplemented at the dose of 12.5, 62.5, 125, and 2.5, 25 mg/kg, respectively. The results show antihyperlipidemic effects by reducing the total cholesterol level, triglyceride and serum-free fatty acids, accompanied by lowered HFD induced obesity in mice (Lai et al., 2016).

13.6.7 Antidiabetic activity Diabetes is a serious metabolic disease caused by a lack of insulin., leading to abnormally high blood sugar levels. Various studies have evaluated the antidiabetic effects of ginger oil (Otunola and Afolayan, 2019; Srinivasan, 2017). An in vitro study showed both 6-shogaol and 6-gingerol can prevent diabetic complications and inhibit advanced glycation end (AGE) production by capturing the methylglyoxal, a precursor of AGE (Zhu et al., 2015). Additionally, 6-gingerol lowered plasma glucose and insulin levels in obese mice induced by a high-fat diet. Nε-carboxymethylisine (CML) is a marker for AGE, which is reduced by 6-gingerol through the activation of Nrf2 (a basic leucine zipper (bZIP) protein) (Sampath et al., 2017). The GEO and its components can provide protection against diabetes, probably by increasing the sensitivity of insulin.

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13. Ginger essential oil

13.6.8 Bronchodilatory effects The bronchodilation effect of GEO in contemporary medicine supports its ancient applications for cough treatment. Numerous studies revealed the bronchodilatory effects of GEO on the airway system. GEO, in conjunction with eucalyptol, citral, and camphor, calmed the airways of rats and inhibited carbachol-induced rat tracheal spasm. GEO has bronchodilator properties that are linked to citral and eucalyptol. Propranolol reversed the bronchodilator effects of GEO, but L-NG-nitroarginine methyl ester (L-N.A.M.E) and indomethacin had no impact on the bronchodilator effects of GEO and citral (Mangprayool et al., 2013). According to conventional applications, syrup of ginger is used for respiratory issues because of its bronchodilatory effects.

13.6.9 Anti-ulcer effects GEO can be used to treat stomach ulcers. Oral administration of GEO zingiberene (28.1%), bisabolene (13.2%), ar-curcumene (14.1%), and sesquiphellandrene (12.9%) exhibited ulcerative colitis-protective effects against acetic acid-induced ulcerative colitis. After 5 days of therapy with varied doses of GEO (100, 200, and 400 mg/kg), the colon weight/length ratio decreased. The 200 and 400 mg/kg of GEO treatment decreased ulcer severity, ulcer index, and ulcer area. The use of 400 mg/kg of GEO reduced the amount and severity of the inflammation. The ulcer zone, lesion score, and lesion index for 400 mg/kg of GEO were equivalent to 4 mg/kg prednisolone in the rat model (Rashidian et al., 2014).

13.6.10 Immunomodulatory effects GEO is considered an immunomodulatory agent. The activity of GEO on the cellular immune response is based on different investigations. 10 4, 10 3, or 10 2 μL/mL dose of GEO have notably inhibitory effects on reducing leukocyte chemotaxis to casein stimuli. After 2 h of carrageenan injection (100 g) into the scrotal chamber, GEO oral treatment (200–500 mg/kg) reduced rolling and leukocyte adherence. The number of leukocytes moving to the perivascular region 4 h after irritating stimulation was also decreased (Nogueira De Melo et al., 2011). The findings suggest that GEO has systemic and direct effects on leukocyte migration, which is a primary mechanism of ginger’s antiinflammatory action.

13.6.11 Other pharmacological activities Clinical studies found the use of GEO as an adjuvant treatment for postoperative vomiting and nausea is beneficial. A nasocutaneous application of GEO (grape seed oil mixed 5%) was used to treat nausea in patients under general anesthesia who were at high risk of postoperative nausea and vomiting. The effectiveness of GEO in aromatherapy is also described in a study, where inhalation of GEO in abdominal surgery patients was found effective in postoperative nausea and vomiting when compared with saline inhalation (placebo control) patients in the first 6 h (Rashidian et al., 2014). In another study of the efficacy of GEO inhalation in breast cancer chemotherapy was found inconvincible. Nausea score significantly lower at

13.7 Applications of GEO

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first but could sustain throughout the treatment, while aromatherapy on vomiting shows no significant effect (Lua et al., 2015). In vitro study also showed that 6-shogaol, zingerone, and 6-gingerol inhibited emetic signals in the afferent nerve of the 10 cranial nerves by inhibiting 5HT receptors, and 6-shogaol has the strongest inhibitory effect (Khodaveisi et al., 2019). The insecticide action of GEO on adults and larvae of Dermestes maculatus De Geer was verified (adult and larva). Adult pesticide exposure to 1.33 μL/mL of GEO for 6 h resulted in 36.2% death. The larva’s sensitivity was greater than that of adults. The increased proportion of death was observed when the pest was exposed to essential oil for a longer period. After 6, 12, and 18 h of D. maculatus larva exposure, the LD90 of GEO were 12.92, 5.14, and 3.06, respectively. On adults of D. maculatus, the corresponding LD90 were 6.52, 4.64, and 4.64 (Babarinde et al., 2018).

13.7 Applications of GEO GEO exhibits many applications in food packaging industries, as the incorporation of GEO with chitosan, and methylcyclopentadienyl manganese tricarbonyl (MMT) were utilized to create a variety of edible bio-composite films. The film exhibited excellent barrier and mechanical properties, as well as slower down the migration of active components and exhibits good slow-release properties. These composite films have the potential to be environment friendly films for active packaging materials. These film successfully restrict the increment in pH value, moisture value of chilled beef, and hue angle value with time and delay fat oxidation and the formation of surface microorganisms on chilled beef (Zhang et al., 2021). Apart from that, the effect of volatiles on GEO encapsulated in ultrafine fibers shown antibacterial efficacy against Listeria monocytogenes. Antimicrobial activity (in situ) of fibers containing 12% GEO on fresh Minas cheese dramatically decreased L. monocytogenes growth during refrigerated storage for 12 days, showing GEO potential application in active food packaging (da Silva et al., 2018). For a millennium, ginger rhizome has been used in traditional medicine to treat inflammation, fevers, colds, respiratory discomforts, nausea, menstrual difficulties, upset stomachs, arthritis, and rheumatism. It has also been used as a spice for taste and digestion, as well as an anti-microbial food preservative that stops the formation of dangerous bacteria. In addition, an animal study shows that GEO has long been used in Ayurvedic medicine to treat emotional issues such as anxiety, sorrow, poor self-confidence, and a lack of passion (Fadaki et al., 2017). The health advantages of GEO are the same as those of the herb from which it is derived, and the oil is even thought to be more helpful due to its greater gingerol concentration, a component known for its antioxidant and anti-inflammatory qualities. GEO is stimulating and warming; hence, it is used in aromatherapy (Salihah et al., 2016b). It can improve focus and alleviate stress, sorrow, anxiety, lethargy, agitation, dizziness, and tiredness (Benedicto, 2017). When used topically, GEO reduces redness, removes germs, prevents skin damage and aging, and restores color and brightness to a dull face. Essential oil of ginger, when used in hair, improves the health and cleanliness of the scalp, relieves dryness and irritation,

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and promotes better hair development by stimulating and increasing circulation to the scalp (Feng et al., 2018b). GEO, when used medicinally, aids in the removal of toxins, improves digestion, relieves stomach and intestinal pain (Lee and Shin, 2017), increases appetite, clears the respiratory tract, soothes aches, and lowers inflammation (Mangprayool et al., 2013). A report published in 2013 suggested the effect of 6-gingerol, an active ingredient in GEO, on hair growth in cultured cells and in mice. Instead of finding that 6-gingerol promoted hair growth, researchers found it suppressed hair growth, both in cultured hair follicles and in a mouse model (Miao et al., 2013). A study undertaken in 2015 shows the suitability of several EOs, including GEO, for use in anti-wrinkle cream. GEO, along with other EOs, was found to have high antioxidant activity. When these EOs were blended in a cream, a reduction in skin roughness was seen in a small group of volunteers (Leelapornpisid et al., 2015).

13.8 Safety, toxicity, and regulation The maximum level of GEO consumption determines its safety. According to fragrance raw material monographs, the typical acceptable concentrations of GEO in detergent, soap, fragrances, and creams-lotion are 0.001, 0.001, 0.08, and 0.005, respectively (Mahboubi, 2019). The safety regulations as additive users, GEO has notified the ECHA (European Chemical Agency) to be classified and labeled as an aspiratory toxin (H304), skin irritant (H315), allergic skin (H317), eye irritant (H319), and respiratory irritant (H319) (PRODUCT:GINGER CHINA OIL, 2018). As far as environmental safety, the H304 might be fatal if it is entering in the airways and absorbed. H401 (acute toxicity to aquatic life) as well as H412 (harmful to aquatic life) is lethal to the aquatic fauna and flora with long-lasting effects. The European Food Safety Authority (EFSA) assessed CG 31 for use in animal feed (Bampidis et al., 2020), concluding that they were “extensively metabolized by the target species and eliminated as benign metabolites or carbon dioxide.” The average feed levels of components of GEO in animal feed are significantly lower than the CG 31 chemicals authorized usage values. As a result, no danger to environmental safety is anticipated. In addition, for toxicological studies, five dosage levels up to 3 mg/plate, GEO was also evaluated for the generation of reverse mutations in Salmonella Typhimurium tester strains TA1535, TA98, TA100, and TA102 with or without metabolic activation. There was no evidence of mutagenic activity in any of the experimental settings (Bampidis et al., 2020).

13.9 Trade, storage stability and transport EOs are combustible fluids. They are delegated to hazardous goods, put away in uncommon spots shielded from direct daylight and warmth at temperatures of 5–25°C. They are transported as per the requirements of ADR (risky products by land), IMDG (hazardous goods by sea), RID (rail transport of perilous goods), ICAO (air transport), and ADN (inland stream transport) (H€ usn€ u Can Bașer and Buchbauer, 2015).

13.10 Conclusion

369

GEO requirements for storage, export, and transportation are naturally included in packages of varying shape and capacity. Vials or potentially tinned copper vessels, covered by steel, aluminum, and glass, carry the GEO. Covers must be as tight as feasible, and their materials must be inert to EOs, and compatibility verified. Cork is not advised for usage due to its porosity and the presence of waxes and tannins that can dissolve in GEO (“HOW TO STORE ESSENTIAL OILS TO MAXIMIZE OIL LIFE,” 2019). The package must provide inviolability and must so be secured by sealing. It is important to ensure that they do not allow liquid or vapor loss. Furthermore, the packages should not be entirely packed; a free space of 5% to 10% is necessary for the upper section, the volume of which is decided by the predicted changes in temperature conditions during transit. When stored in a close-tight container (in a cool, dry place protected from light), GEO is claimed to have a shelf life of at least 2 years under normal conditions. Under typical temperature circumstances, it is stable and approved for usage. GEO has a strong odor; it should not be stored in the same compartment as food. If the items are transported in appropriate and adequately strong containers, there is no reason to be concerned about loss or damage.

13.10 Conclusion Ginger is a medicinally important plant, cultivates in tropical and subtropical countries. The essential oil of ginger extracted using conventional and advance methods. Literature survey in this chapter revealed that despite the limitation in HD extraction methods, still it is widely used techniques to extract GEO from ginger rhizome with variable oil yield and chemical composition. Furthermore, yield and chemical composition of the GEO greatly depend on the geographical location, climate, cultivars, time of maturity and harvest, drying methods and extraction methods. Zingiberene was abundant component of the GEO in most studies included in this chapter. Other major components of GEO were ar-curcumene, β-sesquiphellandrene, farnesene, β-bisabolene, α-copaene, camphene, citral and geranial. GEO gained popularity due to their several biological activities, among them antioxidant, anticancer, anti-inflammatory, and antimicrobial is well documented. The pharmacological activities of the GEO are related to its chemical composition, therefore, standardizing the GEO needs utmost attentions, because the different parameters influenced the yield and chemical composition of GEO. However, scarcity of data is available pertaining to the role and mechanism of these major components of GEO in their biological activities. GEO is considered safe for use and its safety parameter are well documented. Therefore, herbal formulation should be considered in adjuvant therapy. Increase demand and medicinal usage of GEO make it an important commercial oil, therefore adulteration of GEO is another important concern to be addressed. The antimicrobial activity of GEO has been confirmed in different experimental and clinical studies, therefore its application in food packaging industry to increase shelf-life is a growing area of interest, however, its application in other industries such as pharmaceutical, cosmetics, agriculture, dental and other still remain undiscovered.

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C H A P T E R

14 Cinnamon essential oil Atif Liaqata, Samreen Ahsana, Muhammad Shoaib Fayyaza, Ayesha Alia, Syeda Aiman Ashfaqa, Sonia Khana,g, Mujib Arjumund Khanb, Tariq Mehmooda, Adnan Khaliqa, Muhammad Farhan Jahangir Chughtaia, Saeme Asgaric, Masoumeh Parzadehd, Amir Sasan Mozaffari Nejade, and Gulzar Ahmad Nayikf a

Institute of Food Science and Technology, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, Pakistan bDepartment of Nutritional Sciences, La-Mak Foods, Ltd. Shakir Kot Tehsil Sadiqabad, Rahim Yar Khan, Pakistan cDepartment of Biochemistry and Biophysics, Islamic Azad University, Tehran Medical Sciences Branch, Tehran, Iran d Department of Microbiology, Islamic Azad University, Science and Research Branch, Tehran, Iran eSchool of Medicine, Jiroft University of Medical Sciences, Jiroft, Iran fDepartment of Food Science & Technology, Government Degree College Shopian, Srinagar, Jammu & Kashmir, India g Government College Women University, Faisalabad, Pakistan

14.1 Introduction Plant extracts are widely used to enhance the flavor of foods due to their excellent sensory attributes and preservation effects. Essential oils (EO), extracted from aromatic plants are particularly being used by the food processors to enhance shelf life of food due to their antimicrobial characteristics (Isman, 2020). Essential oils extracted from spices are used as natural preservatives to produce nutritious, shelf stable and wholesome food products. Various studies have reported the antibacterial properties of essential oils. For instance, carvacrol combined EO have been found to prevent growth of Bacillus cereus in milk and essential oils extracted from clove exhibit antibacterial properties against Salmonella in cheese (Cui et al., 2016). Food safety is a global and major concern in present time. About one-tenth of total world’s population gets ill by consuming contaminated foods contributing to almost 40,000 deaths each

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00007-4

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year. Microbes are among the major causes of food spoilage worldwide. Bacterial species, among other microbes, play significant role in this part (Cardoso-Ugarte et al., 2016). Historically, various spices and herbs have been used for food preservation due to their bacteriostatic and bactericidal effects ( Jalali et al., 2009; Bahmani et al., 2016; Mozaffari Nejad et al., 2018). They help prevent growth of pathogenic microbes and increase the shelf life of foods. Natural food additives such as essential oils serve as a better alternative to other preservatives due to their economic, less toxic and medicinal concerns. Cinnamon extracted essential oil is mainly used in the food industries due to its distinctive aroma (Nwanade et al., 2021). Cinnamon, from family Lauraceae and genus Cinnamomum has about 250 species including economically significant C. cassia and C. zeylanicum. The plants exhibits varied growth patterns and grows throughout China, Australia and Sri Lanka. It is among the traditional herbal medicines having wide applications in food, seasonings, and medical industries due to its antimicrobial and anticarcinogenic properties (Hamidpour et al., 2015; Hajimonfarednejad et al., 2019). The industrial importance of cinnamon EO lies in the fact that it has a dried inner bark and the oil extracted from its leaves and bark is used by food processors in the manufacturing of value added products. The oil extracted from cinnamon’s leaf is cheaper than bark’s and is therefore used for flavoring purposes. Cinnamon oleoresins are widely used in bakery and beverage industries for flavoring cakes and various soft drinks (Ali et al., 2021; Nabavi et al., 2015). Commercially significant cinnamon essential oils are extracted from Cinnamomum zeylanicum and Cinnamomum camphora. The composition of oil depends largely on geographical conditions and processing conditions. It has been observed that the essential oils extracted from buds possess higher concentration of mono and sesquiterpenes, whereas cinnamaldehyde are found to be concentrated in flowers than buds (Hajimonfarednejad et al., 2019). Cinnamon EO comprises monoterpene hydrocarbons, oxygenated monoterpenes, and diterpenes. Generally, main components of cinnamon EO include trans-cinnamaldehyde, caryophyllene, geraniol, and camphor. Cinnamon essential oil, being an aphrodisiac and tonic is widely used as an ingredient in various medicinal preparations. The oil is helpful in the treatment of biliousness, diarrhea, colon cancer, cholesterol management, and cardiovascular diseases. The oil relieves cramps, stimulates sweating and is also effective against diabetes. Cinnamon leaf extracted essential oil finds application against termites, mildew, and mosquitoes. Essential oil from Cinnamomum cassia has been found to be effective against diabetes due to its insulin enhancing activity (Sharma and Rao, 2014; Da Silva et al., 2021). Cinnamon essential oil is commonly extracted by hydrodistillation via steam or solvent, supercritical fluid extraction, and solvent extraction techniques. The chemical composition and yield of extracted oil depends largely on the extraction method (Akthar et al., 2014).

14.2 Production and composition of cinnamon EO The composition and extraction of cinnamon EO from cinnamon plant is affected by various factors including type of specie, origin of plant, and portion of the plant from where the oil is being extracted. Plant species differ greatly in flavonoid content and antioxidant

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potential whereas no significant role is played by the growing method of plant. Cinnamon leaves and age of bark contribute greatly toward the composition of oleoresins and EOs (Kim et al., 2015). Major components of cinnamon bark oil include cinnamaldehyde and diethyl malonate with concentration of 85.78% and 7.30%, respectively. However, some studies report major constituents of cinnamon essential oil to be cinnamaldehyde, eugenol, linalool, and limonene with concentration of 64.49%, 16.57%, 4.82%, and 2.53%, respectively. These differences might be due to the variation in variety types, environmental factors or method of oil extraction. Among others, cinnamaldehyde has been observed to possess strong antimicrobial properties (Huang et al., 2019; Singh et al., 2007). Essential oil from Cinnamon can be extracted from leaves, bark, wood, or fruit of cinnamon. Extraction can be done via distillation method or by using solvent techniques. Oleoresins are the concentrated compounds derived from aromatic herbs by treating them with a solvent followed by the removal of solvent. In an experiment by Lin et al. (2008), essential oil from the fruit of cinnamon was extracted using distillation technique. The main constituents of the oil were found to be pinene (24.64%), limonene (9.45%), citronellal (1.76%), and citral (35.89%), respectively.

14.2.1 Extraction techniques A number of conventional (steam distillation, solvent extraction, hydrodistillation, hydrodiffusion) and advanced (subcritical extraction, supercritical fluid extraction, microwave-assisted extraction) techniques are adopted for essential oil extraction. Advanced extraction methods are efficient methods due to reduces extraction time, lessen CO2 emission, low energy utilization, and limited usage of solvent (Aziz et al., 2018). Zhang et al. (2017) obtained the cinnamon essential oil by solvent extraction using 95% ethanol. It was extracted at 40°C for 3 h using a magnetic stirrer. This research proposed that the blend of solvent extracted cinnamon/cloves essential oil nanoemulsions exhibit the great antimicrobial potential (Zhang et al., 2017). Similarly, El-Baroty et al. (2010) extracted cinnamon essential oil by using Clevenger apparatus. The obtained yield for cinnamon was 0.96%. The hydrodistilled essential oil possess many antimicrobial and antioxidant compounds displaying antioxidant and antimicrobial potential (El-Baroty et al., 2010). Kasim et al. (2014) extracted cinnamon oil by using Soxhlet extraction and hydrodistillation and compared the yield obtained from both the methods. The solvents used for solvent extraction were hexane, petroleum ether, and dichloromethane. The results revealed that the maximum yield was obtained from dichloromethane (9.11%) trailed by n-hexane (3.84%) and petroleum ether (3.71%). However, the yield via hydrodistillation method was about 1.82%. The results from these extraction techniques have made this evident that Soxhlet extraction gives a higher percentage yield for cinnamon essential oil than the hydrodistillation method. Solvent extraction has shown to be an effectual technique for the extraction of cinnamon oil exhibiting the substantial insecticidal activity (Kasim et al., 2014). Extraction methods that are widely utilized for essential oil extraction from spices and herbs are steam distillation or hydrodistillation, cold pressing, and solvent. Lately, numerous novel extraction techniques have been introduced. These techniques include ultrasoundassisted extraction, ohmic heating-assisted hydrodistillation, microwave-assisted extraction,

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and supercritical fluid extraction (Tunc¸ and Koca, 2021). Steam distillation or hydrodistillation is a physical method extensively utilized for the extraction of essential oils as about 93% of essential oils were extracted by this method. However, this method is not accepted research laboratories due to the lack of suitable distillation vessels and steam generators. However, in research laboratories essential oils are mostly extracted by hydrodistillation. Hydrodistilled oil contains higher percentage of terpene hydrocarbons in comparison to the oil extracted by supercritical fluid extraction that contains a higher percentage of oxygenated compounds (Adinew, 2014). Supercritical fluid extraction (SFE) is a novel, environment friendly and clean technology with specific attention toward extraction of essential oils. Supercritical CO2 is used as solvent that is nontoxic and exhibit moderate extraction times. Moreover, supercritical extracts are known for superior quality in comparison to that produced by hydrodistillation and solvent extraction (Fornari et al., 2012). A long extraction time is required for conventional hydrodistillation of cinnamon oil. UAHDE (ultrasound-assisted hydrodistillation extraction) is utilized to increase the extraction efficiency of essential oil obtained from bark. The factors that influence the efficiency of extraction include ultrasound power, ultra-sonication time and extraction time. In terms of the extraction yield, time, and properties of produced oils, the suggested UAHDE method results are comparable and very close to the conventional hydrodistillation. A higher extraction yield and a shorter extraction time were found as result of UAHDE compared to HD extraction (Chen et al., 2021). Ultrasound power of 300 W was applied on the sample for 35 min and is considered as optimum conditions for extraction. Under optimal conditions, extraction experiments were repeated thrice and the average yield of 2.14% was obtained. The UAHDE made available more precious essential oil with a higher concentration of the crucial trans-cinnamaldehyde substances than the hydrodistillation. The effectiveness of ultrasonication for cinnamon oil production was affirmed by scanning electron micrograph. Furthermore, an examination of usage of electricity and emissions of carbon dioxide reveals that the UAHDE procedure is a much more cost-effective and ecofriendly technique. Thus, it is an effectual and ecofriendly method for extracting cinnamon essential oil, which has the potential to increase the amount and quality of cinnamon oils (Chen et al., 2021). Conventional means for extracting essential oils from organic materials include hydrodistillation (HD), steam distillation, and organic solvent extraction (Khalil et al., 2017). Conventional methods get some innate drawbacks, such as the lesser removal efficiency and the noxious eluent impurities in extraction liquid retrieved essential oils. Due to its low cost and ease of use, HD is presently the most frequently employed innovation for extracting essential oils from pharmacological herbs/plants. Nevertheless, it also has some downsides due to the sufficiently long extraction time, which led to the loss of high volatility and heat delicate constituents of essential oils during in the extraction procedure, which has a significant effect on the amount and quality of essential oils (Xie et al., 2013; Solanki et al., 2018). A few innovative methods for extracting essential oils are supercritical fluid extraction, microwave-assisted extraction (MAE), and ultrasound-assisted extraction (UAE) (Chen et al., 2021). Between many of them, UAE has the significant benefits of preserving effort and time, increasing extraction efficiency, and improving essential oil quality compared to

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sonication, mechanical, and thermal effects that accelerate the extraction process. As a result, ultrasonic hydrodistillation extraction, a comparable method that combines the benefits of UAE as well as HD, has become widespread for obtaining essential oils (Chemat et al., 2017). Ohmic heating can be defined as “the procedure in which the resistance value of the food on its own produces energy when an electricity passes through it.” Therefore, electric current is passed through the content, generating heat energy. Researchers are also interested in ohmic heat-assisted hydrodistillation (OAHD) that involve heat generation by ohmic heating followed by hydrodistillation (Hashemi et al., 2019). Tunc¸ and Koca (2021) determined the optimal ohmic heating-assisted hydrodistillation (OAHD) circumstances for the separation of cinnamon (CEO) essential oil by using response surface methodology in just this study (RSM). Cinnamon essential oil optimized OAHD circumstances were 8.83 V/cm, 119.90 min, and 40 g. Cinnamon essential oil formed zones of inhibition against microbial strains examined. The traditional hydrodistillation technique for extracting oils seems to be time intensive, requires energy, and emits so much carbon dioxide. Once compared to the traditional hydrodistillation, OAHD has great potential to extract oils from various plant materials with shorter process times and lower energy consumption. The ohmic heating-assisted hydrodistillation technique can be scaled up as just a renewable technology for vital oil production (Tunc¸ and Koca, 2021). Reflux extraction (RE) is a common means of extracting bioactive constituents from plant matrix. Thermal decomposition of the constituents at extreme temperature, on either hand, can happen over a lengthy extraction yield. Furthermore, relatively long removal efficiency necessitates so much power and extraction liquid. Microwave-assisted extraction (MAE) has appeared recently as a contemporary traditional extraction technique that includes simultaneously heat up the sample size via dipolar spinning and charge transport. The primary benefits of green extraction methods are including increased oil recovery due to shorter extraction occasions and substantially lower liquid criteria when compared to traditional extraction techniques (Ameer et al., 2017b). The RE technique has been used for years to obtain active molecules from cinnamon powder. Response surface methodology (RSM) is an advanced computational technique used for operations and product enhancement used for the optimization of extraction yield. RSM along with process or product enhancement reduce cost, provide better product quality and reduction in the total number of simultaneous simulation trials (Ameer et al., 2017a; Maeng et al., 2017). Various other techniques employed for the extraction of cinnamon essential oils are summarized in Table 14.1. Cinnamon, cinnamic acid, and cinnamaldehyde are the major compounds extracted by different extraction techniques such as reflux extraction (RE), ultrasound-assisted extraction (UAE), and microwave-assisted extraction (MAE). Lee et al. (2018) optimized the extraction time, extraction yield, and energy consumption of these techniques by response surface methodology. Results concluded that the highest extraction yield was obtained by using microwave-assisted extraction at optimum extraction conditions (ethanol 59%, microwave power of 147.5 W, and extraction time of 3.4). Whereas, reflux extraction utilized maximum energy solvent and time with lowest carbohydrate emission. Hence, the study revealed that, as compared to other two techniques microwave-assisted extraction proved most effective and economic for extraction of active ingredients (cinnamaldehyde and cinnamic acid) from cinnamon powder (Lee et al., 2018).

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TABLE 14.1 Various techniques employed for the extraction of cinnamon essential oils. Extraction techniques

S. no.

Product

Parameters

1

Blended cloves/ cinnamon essential oil

Solvent extraction

95% ethanol Time: 3 h Temperature: 40°C

2

Cinnamon essential oils

Hydro-distillation by using clevenger apparatus

Extraction time: 3 h

3

Cinnamon essential oil

Soxhlet extraction

Yield

Application Antimicrobial potential

Zhang et al. (2017)

0.96%

Antimicrobial antioxidant

El-Baroty et al. (2010)

Dichloromethane at 40°C for 6 h Hexane: 65°C for 6 h Petroleum ether at 60°C for 6 h

9.11% 3.84% 3.71%

Repellency and insecticidal activity

Kasim et al. (2014)

Hydrodistillation

Temperature: 80°C Extraction time: 6 h

1.82%

4

Cinnamon essential oil

Hydrodistillation

Temperature: 70–80°C Time: 3 h

5

Cinnamon essential oil

Ultrasoundassisted hydrodistillation extraction

Ultrasound power level: 300 W Ultrasonication time: 10–60 min Extraction time: 2 h

2.14%

Chen et al. (2021)

6

Cinnamon essential oil

Ohmic heating assisted hydrodistillation

Time: 30–120 min Voltage gradient: 7.5–12.5 V/cm, C

2.14%

Tunc¸ and Koca (2021)

7

Cinnamon essential oil

Microwaveassisted extraction (highest yield)

59% ethanol microwave power: 147.5 W Extraction time: 3.4 min

0.90%

Lee et al. (2018)

Ultrasoundassisted extraction

Ethanol concentration: 55.34% Extraction time: 33.12 min

0.76

Reflux extraction

Ethanol concentration: 63.56% Extraction temperature: 77.62°C Extraction time: 2.25 h

0.94

Supercritical fluid extraction

Supercritical CO2 Temperature: 60°C

8

Cinnamon oil

Adinew (2014)

Oyekanmi et al. (2021)

14.4 Health benefits of cinnamon essential oil

383

14.3 Characterization of cinnamon essential oil Essential oil is obtained from the various parts of cinnamon including bark, leaves, seed, twigs, buds, etc. All parts showed the variable concentration of active compounds. Bark contains about 65%–80% of cinnamaldehyde and 5%–10% Eugenol. While cinnamon leaves constitute of eugenol as major ingredient with the concentration varying from 70% to 95% and cinnamaldehyde about 1%–5% (Rao and Gan, 2014). As trans-cinnamaldehyde is a main bioactive compound in cinnamon oils, so cinnamon bark is considered as superlative raw material for extraction of essential with enhanced essential oil yield. A wide range of compounds were reported in the in the cinnamon essential oil such as trans-cinnamaldehyde, eugenol, b-caryophyllene, L-borneol, cinnamyl acetate, L-bornyl acetate, α-terpineol, α-thujene, caryophyllene oxide, terpinolene, and E-nerolidol (Chen et al., 2021). Generally, cinnamaldehyde, eugenol, methyl-eugenol cinnamyl alcohol, and ethyl-cinnamate are the most predominant constituent reported in cinnamon essential oil (Wang et al., 2009). The qualitative and quantitative analysis or characterization of volatile constituents in cinnamon essential oil is done by GC-MS. Kasim et al. (2014) extracted the cinnamon oil from the cinnamon bark by hydrodistillation and nine ingredients were detected in appreciable amount were alcohols, alkenes, aldehydes, ester, carboxylic acid, ether, and ketone. As trans-cinnamaldehyde (84.97%) was detected as major ingredients in hydrodistilled essential oil along with 9.03% of 1,2-naphthalenedione, 1.11% of ethanone, and 1.03% of borneol (Kasim et al., 2014). Moreover, El-Baroty et al. (2010) also characterize the hydrodistilled essential oil from cinnamon bark. Cinnamon essential oil is a distinctive aromatic monoterpene rich oil contain about 69.65% of monoterpene of total oil. Out of the total 69.65% of monoterpene, essential oil constitute of 45% of cinnamyl aldehyde, 7.74% of eugenol, 5.23% of methyl-eugenol, 5.13% cinnamyl alcohol, 3.86% of ethyl-cinnamate, and 3.31% of dihydroeugenol. Moreover, some other monoterpene such as nerol, geranial, and 1,8-cineol were reported in minor concentration. Many factors are responsible for the variation in actual yields and the composition of phytochemicals in essential oils. This variation is mainly due to cultivation methods, geographical location, harvesting time, and extraction method. These ingredients are widely used in food, pharmaceutical industries (El-Baroty et al., 2010).

14.4 Health benefits of cinnamon essential oil 14.4.1 Antiinflammatory Inflammation is a process of protecting damaged tissues or removing dead cells. The liberation of cytokines including tumor necrosis factor-α and interleukin-1β is an inflammatory response leading to the induction of inflammatory disorders. Interleukins are produced in monocytes and fibroblasts whereas the production of tumor necrosis factor-α is carried out in monocyte/macrophage lineage (Miguel, 2010). Lipopolysaccharides, endotoxins in bacterial species, have been reported to promote cytokines production by facilitating the production and release of interleukin-1β and necrosis factor-α. These cytokines are particularly

384

14. Cinnamon essential oil

involved in cancer development. Besides cytokines, prostaglandins, and nitric oxide have also been reported to initiate inflammatory responses (Hong et al., 2012; Yu et al., 2012). Cinnamon possesses antiinflammatory properties. The extract of Cinnamomum cassia decreased the secretion of necrosis factor-α when administered orally to mice. The antiinflammatory effect relates to the presence of polyphenols. Ethanolic extraction of Cinnamomum cassia decreases nitric oxide production and prostaglandins concentration thereby serving as a potential antiinflammatory source (Han and Parker, 2017). Cinnamon essential oil has been confirmed to reduce nitric oxide production in macrophages and this reduction is mainly due to its cinnamaldehyde component however the antiinflammatory potential was found to be lower than curcumin at same concentration level (Hong et al., 2012). Other components of cinnamon essential oil including linalool and citral have also been reported to possess antiinflammatory properties by inhibiting leukotriene synthesis and cytokines production. This property is attributed largely to cinnamaldehyde content present in the oil. However, the antiinflammatory potential was found to be lower than that of curcumin when tested at similar concentration. Linalool and citral at 50 mg/kg and 50 μg/kg body weight has been found to possess significant antiinflammatory properties. In a study conducted by Ping et al. (2010), it was observed that type-A procyanidin polyphenol (TAPP) extracted from the bark of Cinnamomum zeylanicum plays an important role as an antiinflammatory source when used at 8 mg per kg of body weight. Cinnamon essential oil has the capacity to enhance inflammatory stages by inhibiting cyclooxygenase activity (Yan et al., 2015).

14.4.2 Antitumor and anticancer The production of tumor necrosis factors such as IL-1β during inflammation initiates development of cancer. The capability of cinnamon to hinder IL-1β production and other tumor necrosis factors is among the important modes of action to prevent growth of cancerous cells. Essential oil extracted from cinnamon fruit and water extracted Cinnamomum cassia essential oil exhibited anticancer potential by limiting tumor necrosis NF-κB activation (Sadeghi et al., 2019). The extract was helpful in reducing the activity of COX-2 and tumor necrosis factors in tumor tissues. It was reported that 8 mg/mL extract of Cinnamomum cassia can prevent tumor cell growth by hIAPP fragmentation when administered to humans. Linalool has also been found to prevent tumor cell growth and development (Li et al., 2013b). Anticarcinogenic potential of Cinnamon zeylanicum has been studied. The essential oil extracted from C. zeylanicum interferes with ras signaling and serves an important role in controlling cell growth and differentiation processes. After morphological examinations, significant changes were observed in the morphology of cells including changes in adhesion, cells elongation, and becoming round in shape due to initiation of apoptosis by the essential oils. Similar effects were observed using human leukemia K562 cells where cinnamon extracted essential oils exhibited potential anticancer properties (Muhammad and Dewettinck, 2017). The capability of cinnamon to prevent growth of H. pylori is another phenomena to prevent cancer development in humans. This antibacterial activity is useful as H. pylori is reported to increase the chances of chronic gastritis, coronary heart disease, and gastric cancer. Cinnamon extracted essential oil (100 μg) has the potential to inhibit growth of Helicobacter pylori in a

14.4 Health benefits of cinnamon essential oil

385

better way as compared to ampicillin (10 μg) and erythromycin (15 μg). Also, cinnamon EO has been reported to lessen the spread of cancerous cells in cervix (Azadi et al., 2019).

14.4.3 Antidiabetic Diabetes is a class of metabolic disorders causing elevated blood glucose levels. These disorders cause various complications such as eye diseases, renal diseases, neural impairment, depression, strokes, and reproductive dysfunctions. Various studies have reported the potential of cinnamon to reduce these risks. Essential oil extracted from Cinnamomum cassia plays a regulatory role in lowering glucose levels particularly in type-II diabetes. The decrease relies on the concentration of extract used (Forbes and Cooper, 2013). The application of 100 mg cinnamon essential oil per kg body weight containing 80% cinnamaldehyde exhibited a similar effect. In a study conducted for renal disease, it was found that bark extract of cinnamon (50 μM) had antidiabetic activity. Essential oil extracted from C. burmanii revealed similar results against type-II diabetes mellitus when administered in mouse adipocytes (Yan et al., 2015; Akilen et al., 2013). The combined effect of cumin, oregano, and myrtle essential oil with cinnamon extracted essential oil has been observed to play a significant role in lowering glucose levels in blood and increasing insulin sensitivity in type-II diabetes (Li et al., 2013a). In an experiment, it was observed that cinnamon extracted essential oil enriched with defatted soy flour had a significant impact on enhancing glucose metabolism. The potential of cinnamon extracted essential oils to lower the chances of diabetes corresponds to its inherent characteristic of elevating insulin release and facilitating the formation of glycogen. The polyphenols in cinnamon have been reported to regulate glucose metabolism by repairing damaged or impaired pancreatic beta cells. Cinnamaldehyde improves the islet function of pancreas thereby reducing its workload (Cheng et al., 2012; Li et al., 2013a).

14.4.4 Antioxidant activity Antioxidants play an important role by acting as health protecting compounds. They are among the main constituents to be added in fats and oils. Food processors use antioxidants to prevent or slow down food spoilage mechanisms. Various spices and plants are an important source of antioxidants. They are regarded as the most important agents responsible for the wellbeing of humans as they scavenge free radicals and respond to age related syndromes (Xu et al., 2019). The antioxidant activities of cinnamon and its ether and aqueous extracted essential oils have been reported in various studies. Bark powder extracted from Cinnamomum verum (10%) exhibited antioxidant activity when administered to rats for 90 days. The powder, as showed by the cardiac enzymes, lipid dienes, and glutathione exhibited antioxidant activities. A study reported that cinnamon extracted essential oil possesses superoxide dismutase like activity as revealed by the inhibition capacity of pyrogallol autoxidation (Hassan, 2017; Bellassoued et al., 2019). The aqueous and alcoholic cinnamon extract has been significantly reported to prevent fatty acid and lipid oxidation. Various flavonoids present naturally in cinnamon exhibited

386

14. Cinnamon essential oil

free radical scavenging and antioxidant properties. Various components present in cinnamon essential oil were studied for their antioxidant potential with reference to lipid peroxidation. It was found that eugenol and cinnamaldehyde showed the maximum antioxidant activity as compared to other components. In a study the effectiveness of various spices against antioxidant potential was studied. Results revealed that 1 g/100 g cinnamon bark had a maximum potential for antioxidant activity ( Jayaprakasha and Rao, 2011; Brahmachari et al., 2009). The chemical composition and properties of cinnamon essential oil vary with plant’s growth conditions and segment from where the oil is extracted. The yield and composition of cinnamon essential oil extracted from bark 1 to 3 years old was compared with oil extracted from 5 to 12 years old stem bark of C. cassia plant. Results showed more yield from bark as compared to the entire stem branch indicating the efficiency of essential oil extraction can vary depending on the plant’s growth stage (Geng et al., 2011).

14.5 Application of cinnamon essential oil in food and nonfood industries Food and cosmetic products are among the most important carriers of pathogenic microbes. Foodborne pathogens cause infectious diseases and affect more than 2 million people every year particularly in developing countries. Various studies have been conducted to test the antimicrobial activity of cinnamon EO against food poisoning bacteria. The protective effects of cinnamon in food matrices and packaging material and their potential to prevent microbial growth without need of adding chemical preservatives have also been studied (Nabavi et al., 2015). Essential oil extracted from Cinnamomum cassia has the potential to inhibit growth of spoilage Listeria monocytogenes in meat and meat products without affecting its sensory attributes. Bacterial growth rate was found to be reduced when compared with a sample in which no cinnamon EO was used (Dussault et al., 2014). The antibacterial activity of cinnamon essential oil was also studied against Salmonella typhimurium, Escherichia coli, and A. skirrowii in meat (Tayel et al., 2012; Chen et al., 2013). Cinnamon stick extract showed significant reduction in the growth of Listeria monocytogenes, Staph aureus, S. enterica in cheese by acting as a strong food preservative (Shan et al., 2013). In another study, the antibacterial property of cinnamon essential oil and its components, particularly cinnamaldehyde, against Cronobacter spp. was studied. These pathogens, present in various foods, are reported to cause diseases in adults and children therefore the reduction in their count is desirable. Results showed minimum inhibitory concentration values (MIC values) of cinnamaldehyde to be in the range of 0.25–0.5 mg per mL. Eugenol, an important constituent of cinnamon essential oil showed a little higher range, i.e., 0.51–1.0 mg/mL, revealing a lower antimicrobial activity than cinnamaldehyde. Based on the findings, cinnamon EO was recommended to be used as an active packaging food material or used to create modified atmospheric packaging material. This could significantly prevent against contamination of Cronobacter spp. in various foods (Franˇkova´ et al., 2014). The antimicrobial activities of cinnamon essential oils extracted from leaf-branch and bark were tested against Listeria monocytogenes and Salmonella typhimurium isolated from pork and pig meat respectively. The oils revealed high antimicrobial activity against the said bacterial

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387

species with less than 1 μL per mL MIC values (Mith et al., 2014). In an experiment, cloves and cinnamon essential oils were used to control L. monocytogenes in grounded beef. Results showed that 5% commercial cinnamon essential oils could prevent growth of Listeria monocytogenes by causing 3.5–4 log CFU/g reduction (Khaleque et al., 2016). Cinnamon essential oil, when used in a cosmetic product, has been reported to exhibit antibacterial property when used at 2.5% concentration. The oil was found to effectively inhibit the growth of Pseudomonas aeruginosa, Escherichia coli, and Staph aureus. The inhibition zones were observed to be in the range of 24–44 mm as compared to methylparaben whose inhibition zones lie in 9–8-mm range (Herman et al., 2013). In another experiment, the antibacterial potential of cinnamon bark extract prepared with poly DL-lactide-co-glycolide (PLGA) was tested against Listeria monocytogenes and Staph aureus. Results showed that the oil significantly prevented the growth of said bacteria (Nabavi et al., 2015).

14.6 Conclusion Over, this chapter summarized the composition, sources, potential benefits, extraction techniques, and characterization of cinnamon essential oil. The oil has a distinctive sweet yet spicy flavor which makes it suitable for use in food industries. Cinnamon essential oil can be extracted from various parts of cinnamon plant including bark, twigs, leaves, and stem. However, the concentration of oil varies; bark contains about 65%–80% of cinnamaldehyde and 5%–10% Eugenol, whereas leaves contain eugenol as major ingredient with the concentration varying from 70%–95% and cinnamaldehyde about 1%–5%. It can be extracted through solvent extraction techniques, distillation via hydrodistillation and steam distillation and novel techniques such as supercritical fluid extraction and solvent-free microwave extraction techniques are also being employed. Major compounds present in cinnamon essential oil include cinnamaldehyde, cinnamic acid, linalool, and eugenol. It possesses potential health benefits as it is an antioxidant, has antiinflammatory properties, combats cancer and also plays an active role in treating diabetes. The concentration of cinnamon essential oil used for food and nonfood application must properly be monitored according to regulatory bodies as higher concentrations may lead to severe consequences.

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Ping, H., Zhang, G., Ren, G., 2010. Antidiabetic effects of cinnamon oil in diabetic KK-Ay mice. Food Chem. Toxicol. 48, 2344–2349. Rao, P.V., Gan, S.H., 2014. Cinnamon: a multifaceted medicinal plant. Evid. Based Complement. Alternat. Med., 642942. https://doi.org/10.1155/2014/642942. Sadeghi, S., Davoodvandi, A., Pourhanifeh, M.H., Sharifi, N., Arefnezhad, R., Sahebnasagh, R., Moghadam, S.A., Sahebkar, A., Mirzaei, H., 2019. Anti-cancer effects of cinnamon: insights into its apoptosis effects. Eur. J. Med. Chem. 178, 131–140. Shan, B., Cai, Y.-Z., Brooks, J., Corke, H., 2013. Spice and herb extracts as natural preservatives in cheese. In: Handbook of Cheese in Health: Production, Nutrition and Medical Sciences. Wageningen Academic Publishers. Sharma, V., Rao, L.J.M., 2014. An overview on chemical composition, bioactivity and processing of leaves of Cinnamomum tamala. Crit. Rev. Food Sci. Nutr. 54, 433–448. Singh, G., Maurya, S., Delampasona, M.P., Catalan, C.A.N., 2007. A comparison of chemical, antioxidant and antimicrobial studies of cinnamon leaf and bark volatile oils, oleoresins and their constituents. Food Chem. Toxicol. 45, 1650–1661. Solanki, K.P., Desai, M.A., Parikh, J.K., 2018. Sono hydrodistillation for isolation of citronella oil: a symbiotic effect of sonication and hydrodistillation towards energy efficiency and environment friendliness. Ultrason. Sonochem. 49, 145–153. Tayel, A.A., El-Tras, W.F., Moussa, S.H., El-Sabbagh, S.M., 2012. Surface decontamination and quality enhancement in meat steaks using plant extracts as natural biopreservatives. Foodborne Pathog. Dis. 9, 755–761. _ 2021. Optimization of ohmic heating assisted hydrodistillation of cinnamon and bay leaf essential Tunc¸, M.T., Koca, I., oil. J. Food Process Eng. 44, e13635. Wang, R., Wang, R., Yang, B., 2009. Extraction of essential oils from five cinnamon leaves and identification of their volatile compound compositions. Innov. Food Sci. Emerg. Technol. 10, 289–292. Xie, Z.-S., Xu, X.-J., Xie, C.-Y., Huang, J.-Y., Yang, M., Yang, D.-P., 2013. Volatile components of Rhizoma Alpiniae officinarum using three different extraction methods combined with gas chromatography–mass spectrometry. J. Pharm. Anal. 3, 215–220. Xu, T., Gao, C., Feng, X., Yang, Y., Shen, X., Tang, X., 2019. Structure, physical and antioxidant properties of chitosangum Arabic edible films incorporated with cinnamon essential oil. Int. J. Biol. Macromol. 134, 230–236. Yan, Y.-M., Fang, P., Yang, M.-T., Li, N., Lu, Q., Cheng, Y.-X., 2015. Anti-diabetic nephropathy compounds from Cinnamomum cassia. J. Ethnopharmacol. 165, 141–147. Yu, T., Lee, S., Yang, W.S., Jang, H.-J., Lee, Y.J., Kim, T.W., Kim, S.Y., Lee, J., Cho, J.Y., 2012. The ability of an ethanol extract of Cinnamomum cassia to inhibit Src and spleen tyrosine kinase activity contributes to its antiinflammatory action. J. Ethnopharmacol. 139, 566–573. Zhang, S., Zhang, M., Fang, Z., Liu, Y., 2017. Preparation and characterization of blended cloves/cinnamon essential oil nanoemulsions. LWT Food Sci. Technol. 75, 316–322.

C H A P T E R

15 Nutmeg essential oil Mahpara Khanama, Aamir Hussain Darb, Fiza Begb, Shafat Ahmad Khanb, Gulzar Ahmad Nayikc, and Ioannis Konstantinos Karabagiasd a

Department of Food Engineering and Technology, Institute of Chemical Technology, Jalna, Maharashtra, India bDepartment of Food Technology, Islamic University of Science and Technology, Awantipora, Kashmir, India cDepartment of Food Science & Technology, Government Degree College Shopian, Srinagar, Jammu & Kashmir, India dDepartment of Food Science and Technology, School of Agricultural Sciences, University of Patras, Agrinio, Greece

15.1 Introduction When fully grown, the nutmeg tree, Myristica fragrans Houttyn, is an evergreen leafy tree reaching a height of 12 m (Choo et al., 1999). The pericarp, aril, and seed make up the spherical, yellowish-green nutmeg fruit, which has a diameter of 4 cm (Choo et al., 1999). The seeds and arils, known as nutmeg and mace, are popular spices that are occasionally employed in the Chinese and other traditional remedies for their anticarcinogenic and medicinal qualities. These are also renowned for having psychedelic components and being poisonous. The 12-cm-thick pericarp is generally chopped into thick slices or finely diced strips, then treated and glazed with thick sugar syrup or honey before being consumed as a tasty candy tidbit. It’s also cooked with syrup and treated with salt water to produce a nutmeg concentrate for a pleasant drink. Since the previous century, nutmeg and mace oils have been widely researched for their content and organoleptic properties. These oils are mostly composed of greater than 80% monoterpenes, greater than 5% monoterpene alcohols, greater than 5% aromatics, and some minor components. Nutmeg gives a volatile oil, a fixed oil, proteins, lipids, carbohydrates, and mucilage, according to phytochemical analysis research. Myristin and myristic acid are found in the fixed oil which gives it a characteristic flavor. Pine, camphene, myristin,

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00012-8

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Copyright # 2023 Elsevier Inc. All rights reserved.

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isoelemicin, eugenol, elemicin, isoeugenol, safrole, sabincene, diametric phenylpropanoids, lignas, methoxyeugenol, and neolignas are among the volatile oils found in nutmeg. Aphrodisiac, stomachic, carminative, tonic, nerve stimulant, aromatic, narcotic, astringent, hypolipidemic, antithrombotic, antifungal, antidysentery, and antiinflammatory properties have been described for nutmeg (Tajuddin et al., 2005). It is also said to help with paralysis and improve blood circulation (Olaleye et al., 2006). The chapter focuses on the production, composition, extraction, applications, safety aspects, and storage of nutmeg essential oil.

15.2 Botanical aspects Myristica officinalis, Thunberg, Myristica aromatica, Lamarck, and M. officinalis, Houttuyn, and Fragrans are few botanical names of nutmeg tree. This now has been widely used by botanists. Nutmeg tree is native to Molucca Islands, although it is also grown in Sumatra, Mauritius, French Guiana, and other West Indian islands. This nutmeg is widely farmed in Grenada and Trinidad in the Caribbean, and in Central and East Java. Nutmeg tree has a height of 20–25 ft., with a gray brown color. The leaves are alternating on petioles that are 0.5–0.75 in. in length, elliptical below, subbifarious, glabrous, obtuse at base, acuminate, very whole, fragrant, darker green, lustrous, paler underneath, and 3–6 in. in length. These flowers are tiny, dioecious, appearing in axillary, subumbellate racemes that are occasionally forked or complex. The peduncles and pedicels are free from hair, latter possessing a rapidly deciduous, oval at top, which is frequently pushed against the flower of 3–5 male flowers, or more, are arranged on a peduncle. Except for the pedicel, which is extremely frosty, the female blooms are nearly identical to the male flowers. The fruit is a fleshy pericarp around the size and shape of a small pear, with a roughly spherical appearance. The flesh is bitter, yellowish on the interior, nearly white, 4 or 5 lines thick, and separates into two valves of roughly similar size. The nut is oval shape, hard, rough, darker brown, glossy shell pale and finished inside and is thick. Younger seed, or nutmeg, round, paled brown, and finished, but shrivels and developed uneven, lines on surface.

15.3 Essential oil production Different techniques are utilized for extracting essential oils from the plants, the most common which is hydrodistillation; nevertheless, additional processes such as supercritical fluid and solvent extraction, enfleurage, and mechanical pressings were used for particular goods (Surburg and Panten, 2006). Based on the operating techniques and geographic location of the plant, yields of extract from the nutmeg have been observed in a range of 1.46%–16.5% (Table 15.1). Nutmeg essential oil, a steam distillation that is yellow (palled), virtually colorless, is responsible for the distinctive odor of spices (Marzuki et al., 2014).

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15.5 Extraction of nutmeg essential oil

TABLE 15.1

Extraction of essential oil from different parts of nutmeg (Myristica fragrans).

Origin/Parts (%)

Technique

Apparatus

Yield (%)

Indonesia/seeds

Hydrodistillation

–

6.85

Muchtaridi et al. (2010)

Sri Lanka/seeds

Steam distillation

Clevenger

10–15

Sarath-Kumara et al. (1985)

Nigeria/seeds

Hydrodistillation

Clevenger

1.46

Ogunwandea et al. (2003)

Italy/seeds

Super critical fluid extraction (SEF)/hydrodistillation

Extraction vessel and separator vessels/clevenger

India/seeds/ fruit

Hydrodistillation

Clevenger

3.9–16.5

Maya et al. (2004)

Malaysia/ pericarp/fruit/ seed

Hydrodistillation

Clevenger

2–3

Choo et al. (1999)

References

Piras et al. (2012)

15.4 Composition of nutmeg The seeds are the most common source of nutmeg essential oil, which it comes from the mace, leaves, and pericarp (Choo et al., 1999). The volatile compounds in essential oils range from 5% to 15% and are made up of greater than 80% monoterpenes, greater than 5% monoterpene alcohols, and greater than 5% aromatic and other miscellaneous chemicals. Alphapinene, sabinene, 1,8-p-methadiene, beta-pinene, 1,4-p-menthadiene, and camphene are the main components of monoterpenes. The aromatic fraction comprises myristicin, elemicin, and safrole, while some elements include methyleugenol, eugenol, isoeugenol, and toluene (Piras et al., 2012; Piaru et al., 2012a, 2012b). Based on the results of gas chromatography (GC), the retention index (RI), and mass spectrometry (MS) of varying quantities of the myristicin, sabinene, limonene, eugenol, safrole, and pinene derivatives, the composition of nutmeg oil had broad fluctuations as shown in Table 15.2.

15.5 Extraction of nutmeg essential oil The most popular method for extracting the essential oils (EOs) is hydrodistillation (HD). In theory, it’s the same as a heterogeneous distillation. The plant is immersed in a water portion, and this heat is utilized above the boiling point at atmospheric pressure. In this case, the odor particles in plant cells are released in an azeotropic mixture, when it is heated. Even though most of the components have boiling temperatures exceeding 100°C, these are mechanically propelled by water vapor. The combination of water and EOs are separated due to the decantation after cooling by condensation. The European Pharmacopeia’s “Clevenger” technology permits the aqueous phase of distillate to be recycled in boiler using

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TABLE 15.2 Chemical composition of nutmeg (Myristica fragrans) essential oil. Origin

Major components

Yield (%)

References

Italy (seeds)

Myristicin Sabinene α-Pinene β-Pinene β-phellandrene Safrole Terpinen-4-ol

32.8 16.1 9.8 9.4 4.9 4.1 3.6

Piras et al. (2012)

India (seed)

Myristicin Sabinene Elemicin Safrole

1.1–45.6 6.3–45.5 1.0–29.7 0.1–22.1

Maya et al. (2004)

Malaysia/pericarp

Terpinen-4-ol α-Pinene Myrcene Limonene ɣ-Terpinene β-Pinene

19.1 15.2 9.1 9.1 9.1 9

Choo et al. (1999)

Sri Lanka (seeds)

Sabinene α-Pinene β-Pinene Limonene Myristicin Elemicin

43.42 17.48 12.13 3.22 3.06 1.54

Sarath-Kumara et al. (1985)

Nigeria (seeds)

Sabinen α-Pinene α-Phellandrene Terpinen-4-o1 p-Cymene Myrcene β-Pinene

49.09 13.19 6.72 6.43 3.30 3.09 2.42

cohobate equipment. As a result, the density differences between water and volatile molecules (EOs) separate them. Depending on the plant material, the HD lasts between 3 and 6 h. This variable has an impact on EO production and chemical composition.

15.6 Uses and applications Nutmeg (Melissa fragrans) is historically utilized to make desserts. Nutmeg fruit’s seed has been widely used, notably in culinary, medicinal, and cosmetic sectors. Nutmeg is utilized as a flavor agent in a variety of baked products, confectionary, meats, sausages, puddings, vegetables, and beverages. It is utilized as a component of curry powder, tea, and soft drinks, and it is added to milk and alcohol (Olaleye et al., 2006).

15.6 Uses and applications

395

Nutmeg is a popular spice of many nations. Nutmeg is utilized in sweet recipes in Middle East and India. It is used as a flavor agent in potatoes, meats, eggs and even spinach in most European meals, as well as soups and sauces in the traditional medication used in Arabia, Israel, and Jewish community. It is utilized to regulate vomiting, bowel motions, as well as to treat TB, colds, and fevers, and to treat respiratory disorders in general. It has antihelminthic properties and used for the treatment of skin conditions including eczema and scabies (Bamidele et al., 2011). This utilized alternative medication in Unani medicine is to treat the sexual problems in males (Tajuddin et al., 2005). Nutmeg is also primarily utilized to treat inflammatory disorders, joint, muscular discomfort, and liver illness. Nutmeg oil aids in the dissolution of kidney stone and the relief of kidney infections, and treatment of diarrhea, rheumatism, and cholera (Al-Jumaily and Al-Amiry, 2012). Nutmeg and nutmeg oil is used to treat the nervous, dizzy disorders, according to the relevant literature (Al-Jumaily and Al-Amiry, 2012; Saxena and Patil, 2012).

15.6.1 Applications of nutmeg and nutmeg oil in food industry Nutmeg is a valuable product. It is the world’s oldest trade commodity and is frequently utilized in the culinary and medicinal industries. It’s widely used in cuisine, medicine, and cosmetics as an essential oil, powder, crush, and in the whole. Nutmeg has a strong and pleasant aroma, as well as a somewhat toasty and sweet flavor. Many baked foods, breads, confectionary, puddings, dairy, meat, sausage, dishes, veggies, and drinks include it. It’s also used in candy, chewing gum, syrups, curry powder, teas, and soft drinks, and it’s a blend with milk and the alcohol (Olaleye et al., 2006). Nutmeg had many food applications as shown in Table 15.3. Nutmeg is a famous spice, utilized for fragrant, aphrodisiac, and therapeutic purposes since the ancient times. It is a high-energy, high-carbohydrate, high-protein, and high-fiber food. Vitamins A, C, and E are the most abundant, including electrolytes (Na and K), minerals (Mg, Ca, Cu, iron, Zn, Mn, and P), and phytonutrients, such as crypto-xanthin B and caroteneB (Agbogidi and Azagbaekwe, 2013). Nutmeg essential oil has been utilized in the cosmetic industry, in natural flavoring extracts and perfume due to its fragrance. The oil has been used as a flavoring agent, substituting the ground nutmeg to prevent solid particles in meals and beverages. Nutmeg essential oil is potentially used as a bio-preservative, due to its TABLE 15.3

Nutmeg products and its food application.

Nutmeg product

Uses

Dried whole, ground nutmeg

Flavoring agent in both domestic and industrial use: meat and dairy products (sausages, baked products, eggnog, ice cream, etc.)

Nutmeg oil

Product flavor (processed foods and beverages)

Mace: dried, whole, ground

Nutmeg domestic and industrial culinary used as flavor for sweet food, bakery, and dairy products

Mace oil

Flavoring agents (processed foods and baked products) extract is utilized for perfumes, scented soaps, creams, and chewing gum

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antibacterial and antioxidant characteristics. Given that, (1) it decreases the possible risk of health and growing unfavorable image of synthetic preservatives, increased interests have been focused in essential oils (EOs) and the applications in food preservation and (2) foodborne diseases is growing in public health concern around the world, necessitating the preservative methods (Hyldgaard et al., 2012; Djenane et al., 2013). In addition, the essential oils are used as preservatives based on their antibacterial and antioxidant properties. Many of these processes are efficient in inhibiting the growth of microbes, oxidation of food, and rancidity, and open new frontiers in the attractive natural preservatives for their usage in the food industry. To prevent the adverse effects, connected with the utilization of the synthetic preservatives, it is utilized as a natural preservative with antioxidant and antibacterial characteristics (Saatchi et al., 2014). As a result, the antibacterial and antioxidant capabilities of nutmeg essential oil and its different oleoresin extracts were discovered, making a viable natural food preservative for replacing the synthetic ones (Kapoor et al., 2013). Exploiting the antibacterial characteristics of natural plant extracts is one of the contemporary approach to improve the sanitary safety of produced food items, allowing thus, the reduction in the usage of antimicrobial agents, that pose a possible human danger. In context, the EOs have long been known for their antibacterial characteristics, and these are still the focus of numerous studies evaluating their microbiological potential as alternatives to chemical agents in the food industry. Nutmeg EOs and other oleoresin extracts, showed strong antioxidant activity as well. The oils and oleoresins exhibited scavenging activity by the 2,2-diphenyl-1-picryl-hydrazyl (DPPH) and 2,20 -azinobis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS+) assays, in preventing the oxidation of oils, along with the strong reducing power and chelating properties. The antioxidant activity demonstrated was comparable to and in some cases, superior to recognized antioxidants. Nutmeg oil has been shown to have some potential antioxidant components. Malabaricone C is one of these substances, which has more antioxidant activity than the frequently used synthetic antioxidants (Kapoor et al., 2013). The functionality of antioxidants as food preservatives is shown in both the natural (ascorbic acid and tocopherols) and artificial (propylgallate, tertiary, butylated hydroxyanisole, butylated hydroxytoluene) forms. However, there are some concerns regarding the safety and potential side effects of the artificial antioxidants as dietary additives. In recent years, research had focused on the extraction of natural antioxidants from spicy and medicinal plants, which play a significant role in the food sector, in combating the food degradation. As a result, the antioxidant and antibacterial capabilities of nutmeg essential oils and oleoresin extracts are highly important in protecting microbial and oxidation-induce food degradation. The potential benefits made nutmeg a natural food preservative (Kapoor et al., 2013). Furthermore, nutmeg generates a significant amount of essential oil. Plants’ total essential oil concentration is typically relatively low, seldom exceeding 1%; but, in exceptional situations, such as clove (Syzygium aromaticum) and nutmeg (M. fragrans), it can reach 10% (Djilani and Dicko, 2012). The European Commission has approved a number of essential oil components for their intended usage as flavorings in food products. Linalool, eugenol, carvone, thymol cinnamaldehyde, vanillin, citral, and limonene are among the registered flavorings, all of which are deemed to pose no danger to the consumer’s health. These drugs are likewise classified as generally regard as safe by US (FDA) (GRAS). Clove, oregano, thyme, nutmeg, basil, mustard, and cinnamon are among the crude essential oils designated as GRAS by the FDA. Despite the fact that essential oils and their components have antimicrobial action in vitro, their applications as preservatives in food

15.8 Conclusion

397

has been limited since a large concentration is required to produce the adequate antibacterial activity. Interactions with matrices of food such as fat, carbohydrates, and proteins, degrade the hydrophobic essential oil molecules in many food products. The antibacterial efficacy of essential oil components is also affected by pH, temperature, and microbial contamination levels. Extrapolating results from the tests of food samples is difficult, and a reduction in the antimicrobial compound performance is to be expected. Before essential oils or their constituents are added in food products, as this is important to observe how will these react with food particles in vitro. In this light, it is essential to evaluate the problem for their safe use and applications in food. One of the most significant barriers, in utilizing the essential oil as preservatives in foods, is that these are frequently insufficiently strong as single components, and when added in sufficient levels to give an antibacterial impact, these create some poor organoleptic effects. Even at low quantities, the strong fragrance of essential oils can induce plenty unpleasant organoleptic effects that surpass the acceptable threshold for consumers. Even though, the FDA has categorized nutmeg crude essential oil as GRAS, some claimed that for long time usage and high dosage of nutmeg, could had a risk in health (Periasamy et al., 2016).

15.7 Safety, toxicity, and regulation of nutmeg essential oil Nutmeg has many advantages: These are antidiarrhea activity, antidiabetic, stimulant, antifungal, carminative, and antiinflammatory properties (Asgarpanah and Kazemivash., 2012). In Asia, ancient remedies such as nutmeg and mace are used to alleviate stomach pains, diarrhea, and rheumatism. It includes volatile oily compounds, and myristicin which is an alkyl benzene derivative. Myristicin acid is a mild monoamine oxidase inhibitor, and few structures are comparable to those of a serotonin agonist. Myristicin can be converted into amphetamine-like molecules having hallucinogenic properties comparable to lysergic acid diethylamide (Forrester, 2005). Myristicin is a flavoring plant component that has shown substantial psychopharmacological and insecticidal effects (Lee et al., 1998). Myristicin has a metabolic path like safrole. Myristicin may also be synthesized, and it has been regarded as a low-cost drug due to its hallucinogenic properties, leading thus, to its classification as a hallucinogen agent. Hallucinogens (psychedelics) are psychoactive drugs that change perception, mood, and a variety of other factors (Nichols, 2004). Because myristicin is a hallucinogen, it is used as a cheap hallucinogenic intoxicant. Nevertheless, the repeated use can result in fatalities due to organ damage and cardiovascular effects. More cases of nutmeg poisonous effects, have been recorded recently, and include some numerous fatal case regarding the myristicin poisoning (Nichols, 2004). Such poisonings are caused not only by the poisonous effects of myristicin alone, but also in combination with other drugs.

15.8 Conclusion Nutmeg (M. fragrans Houtt.) spice seeds belongs to Myristicaceae family. It has a pungent and good aroma, with a sweet taste. In many baked products, such as bread, confectionary, puddings, dairy, meats products, sausages, sauces, vegetables, and beverages it is used as

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flavor agent. Due to its aroma, nutmeg oil is utilized as a natural flavor agent which is mainly extracted, and a perfume in the cosmetic industry. Nutmeg is a valuable spice, known since ancient times because of its aroma, aphrodisiac, and curable properties. Due to its antimicrobial and antioxidant properties, this oil is a bio-preservative. Nutmeg has a highly nutritional value (carbohydrates, proteins, dietary fiber, vitamins A, C, E, and minerals, e.g., Ca, Cu, Fe, Mg, Mn, Zn, and P). Nutmeg has numerous medicinal properties, that include cure for gastrointestinal causes like ulcers in stomach, indigestion, liver problems, emmenagogue, nervine, digestive, diuretic, diaphoretic, and food flavoring properties. Nutmeg essential oils from different areas vary in their composition, usually in phytochemicals like limonene, sabinene, α-pinene, β-pinene, myristicin, sabinene, and safrole.

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Piaru, S.P., Mahmud, R., Perumal, S., 2012a. Determination of antibacterial activity of essential oils of Myristica fragrans Houtt. using tetrazolium microplate assay and its cytotoxic activity against vero cell lines. Int. J. Pharmacol. 8 (6), 572–576. Piaru, S.P., Mahmud, R., Majid, A.M.S.A., Ismail, S., Man, C.N., 2012b. Chemical composition, antioxidant and cytotoxicity activities of the essential oils of Myristica fragrans and Morinda citrifolia. J. Sci. Food Agric. 92, 593–597. Piras, A., Rosa, A., Marongiu, B., Atzeri, A., Dessi, M.A., Falconieri, D., Porcedda, S., 2012. Extraction and separation of volatile and fixed oils from seeds of Myristica fragrans by supercritical CO2: chemical composition and cytotoxic activity on Caco-2 cancer cells. J. Food Sci. 77, 448–453. Saatchi, A., Kadivar, M., Soleimanian Zad, S., Abaee, M.S., 2014. Application of some antifungal and antioxidant compounds extracted from some herbs to be used in cakes as biopreservatives. J. Agric. Sci. Technol. 16, 561–568. Sarath-Kumara, S.J., Jansz, E.R., Dharmadasa, H.M., 1985. Some physical and chemical characteristics of Sri Lankan nutmeg oil. J. Sci. Food Agric. 36, 93–100. Saxena, R., Patil, P., 2012. Phytochemical studies on Myristica fragrance essential oil. Biol. Forum Int. J. 4 (2), 62–64. Surburg, H., Panten, J., 2006. Common Fragrance and Flavor Materials. Preparation, Properties and Uses, fifth ed. Wiley-VCH, Weinheim, ISBN: 978-3-527-31315-0. Tajuddin, Ahmad, S., Latif, A., Qasmi, I.A., Amin, K.M.Y., 2005. An experimental study of sexual function improving effect of Myristica fragrans Houtt. (nutmeg). BMC Complement. Altern. Med. 5 (16), 1–7.

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C H A P T E R

16 Rosewood essential oil Muhammad Haseeb Ahmad, Muhammad Faizan Afzal, Muhammad Imran, Muhammad Kamran Khan, Muhammad Sajid Arshad, Muhammad Bilal Hussain, and Marwa Waheed Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan

16.1 Introduction Red rosewood oil is important oil extracted from forest tree named Aniba rosaeodora DuckeLauraceae. It is generally called a tropical rosewood plant. It belongs to Amazonia. Its oil is used in French Guiana. It is the main element of good-quality scents and other beauty products (Chantaine et al., 2009). Besides its use in the cosmetics industry, its essential oils are also famous for their antifungal agent, antioxidant, cytotoxic, antibacterial, and antimutagenic characteristics (Giordani and Kaloustian, 2006; de Almeida et al., 2009; Soeur et al., 2011). This plant exists in Guyana, Brazil, Suriname, Peru, Venezuela, and Colombia. It stretches along both sides of the Amazon River, from Amapa to northwestern Peru. It also performed in the towing basin of the Purus River in the state of Para. It occurs in upland humid forest areas, near the source of small rivers, where it mainly grows (Sampaio et al., 2003). It is a large tree with a height of 30 m and a diameter of 2 m, the trunk is straight, cylindrical and the bark is yellowish-brown. Its top cover is in the shape of a crown. Its flowering takes place between October and March of each year, and the fruiting season is from February to June. Rosewood plants change their leaf-like parts during the fruiting season. When ripe, its fruits will fall to the ground, but they will still be the prey of beetles at the treetops or after spreading, which leads to the availability of seeds, which is a crucial point for the reproduction of the species (Maia and Mourao, 2016).

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16.2 Production of rosewood essential oil From 1875 to 1975, French Guiana extracted mahogany oil on a large scale and felled mahogany trees, significantly reducing these arboreal plants’ natural population (Nair, 2007). Since 2001, the export of rosewood oil has experienced a decline as Guiana’s legislation restricts the logging of this species in the planting area. Overall, Brazil is considered the largest producer of this oil (Amusant et al., 2015). The risk of rosewood being eliminated in its place of origin and the substantial monetary benefits highlight the importance of these trees because of their optimal growth and essential oil quality. Against this background, Guiana’s farmers are considering establishing viable rosewood oil production by planting trees instead of demolishing large trees in their original areas. Since 1940, different planting systems have been tested by replanting natural tree seedlings. The effects of soil quality and light on tree growth and planting density are also estimated (Amusant et al., 2015). Trees are best grown under the following soil conditions: low soil density, high clay content, high soil porosity, and high nutrient content (Krainovic et al., 2020). In contrast, good results were obtained under fallow and later secondary forest soil conditions. Among the primary environmental factors, light availability has been the most significant parameter on the growth, reproduction, and survival of Rosewood (Useche et al., 2011). Rosewood plant is resistant to shade, but it also needs light to increase its diameter and height. It can also grow best in areas with a limited shade of forests, where the light is about 30% on the yellow clay oxidized soil. In the seventh year of planting, the spacing was 10  5 m, and a plant height increase of 0.75 m/year was observed (Amusant et al., 2015). Few scientists have observed that the percentage of oil in seedlings less than 10 cm in diameter is higher than that of older plants. The more excellent oil production from young plants suggests that commercial dilution and short rotations provide an exciting source of essential oils. In French Guiana’s view, forest land with an area of 0.5 to 2 ha has traditionally been cleared to produce food crops for 3 years (Tsayem Demaze, 2008). The production of rosewood in the area may be a substitute. Remember where the trees are in the plot, and nearby forests can provide shade during the initial growth of the trees. Therefore, it is suggested that the neighboring forests and the origin of the seeds impact the growth of trees and the production of oil, leading to the production of young rosewood plants.

16.3 Composition of rosewood oil The highest concentration of rosewood oil is linalool (84.8%). The composition of α-pinene, caryophyllene oxide, and alloaryldiene is 0.1%. Oxidized terpineol and sesquiterpenes constitute approximately (2.9%) and (3.4%), respectively. Some traces of paranoid are also present, terpinen-4-ol, (£)-13-ocimene, spathulenol, ep-a-cadinol, 1-ep-cubenol epi-a-muurolol, (£)-caryophyllene, and a-humulene in rosewood essential oil (Sampaio et al., 2012). By sampling, it was observed that the chemical composition of rosewood essential oil in the two regions was different, and the amount of essential oil from the Nova Aripuana region was relatively large (Krainovic et al., 2018). Scientific research shows that there are very few compounds in samples taken from a single area. For example, eucalyptus oil is not found in the

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leaves and branches of Novo Aripuana but is present in Maues plants. In contrast, p-cymene was only found in the stems of Novo Aripuana, although it was not found in plants of Maues and younger (Krainovic et al., 2018). The production of rosewood essential oil (REO) needs a thorough understanding of plant management, from the proper processing of trees to the production of high-quality REOs for the global market. The degree of change in the composition of the REO from its source and the influencing factors in this regard play a key role. REO includes monoterpenes (low molecular weight) and sesquiterpenes, and its main component is linalool, which is 78%–93% (Fidelis et al., 2012). Therefore, environmental factors that play an essential role in the growth of Rosewood plants must promote the redirection of metabolic pathways to ensure the synthesis of various compounds (de Morais, 2009). It is assumed that the research objective is (a) the planting area affects the chemical composition and yield of REO; (b) the removal of REO from different parts of the plant result in the manufacture of end products with different chemical compositions (c) the use of recycled biomass produce different characteristics of REO, rather than the REO system which utilizes the biomass from the first harvest under management (Cespedes-Payret et al., 2012).

16.4 Extraction of rosewood oil The extraction method is one of the essential aspects that determine the quality of essential oils. Improper extraction conditions can damage or change its chemical properties. These points should be checked depending on the application of essential oils (Reyes-Jurado et al., 2015). Therefore, proper extraction methods and techniques are necessary for producing essential oils with desired characteristics (Tongnuanchan and Benjakul, 2014). A summary of all extraction methods that can be used for the extraction of rosewood essential oils has been demonstrated in Fig. 16.1.

16.4.1 Conventional extraction methods 16.4.1.1 Steam distillation According to Masango’s (2005) research, steam distillation extracts roughly 93% of essential oils, while other approaches extract the remaining 7%. The water is boiled in this procedure, and the plant matter (Rosewood) reacts with the steam generated by the boiling process. The disruption of plant cell structure is primarily due to the application of heat. As a result, aromatic and volatile compounds from the plant material are released and transferred into the tube, where the steam cools to form a mixture of distilled water and essential oils. The oil fraction then separates from its liquid state due to a change in density. The most significant elements in this process are steam pressure, extraction time, and temperature. Furthermore, this is a time-consuming procedure that necessitates the re-distillation of oil (Babu and Kaul, 2005; Stratakos and Koidis, 2016). A downside of this old approach is that few volatile chemicals are destroyed due to the high operating temperatures and long extraction times (Gavahian et al., 2013).

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Extraction Techniques

Conventional Techniques

Steam Distillation

Hydro Distillation

Supercritical Fluid Extraction

FIG. 16.1

Innovative Techniques

Solvent Extraction

Microwave-Assisted Extraction

Ultrasound-Assisted Extraction

Extraction techniques for the rosewood oil.

16.4.1.2 Hydro-distillation Hydro-distillation is one of the oldest and most famous procedures for extracting essential oils (Hashemi et al., 2017). Oil is removed from the plant’s delicate portions using a solid– liquid extraction method involving plant matter and hot water. A Clevenger apparatus is also installed in the distillation vessel. To obtain a vapor phase, the water and plant sample combination is heated in a condenser, and the segregated oil is collected in a collecting bottle. However, this method has several disadvantages, particularly the long extraction time, which might cause heat-labile components to degrade and create compounds (Hashemi et al., 2018, 2017; Asl et al., 2018). Furthermore, these elements are engaged in the implementation. Temperature and processing duration are difficult to control, resulting in partial or prolonged extraction. As a result, scientists and researchers are exploring ways to replace this inefficient practice (Hashemi et al., 2018; Gavahian et al., 2016a, b). 16.4.1.3 Hydro-diffusion It’s a type of steam distillation where the steam approaches the distiller in a variety of methods. This method is appropriate when the plant material has been dehydrated that is not sensitive to high temperature boiling (Vian et al., 2008). During this procedure, heat (in the form of vapor) is injected from the top of the specimen, while in the case of the steam distillation process, heat is introduced from the bottom. This software can also operate at low

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pressures, lowering steam temperatures down below 100°C. This technique is superior to steam distillation in processing time and oil production as it uses less steam which ultimately reduces the operating cost (Tongnuanchan and Benjakul, 2014). 16.4.1.4 Solvent extraction Solvent extraction method is normally used for heat sensitive samples. The primary goal of this method is to extract odorous lipophilic components from plant sources using a variety of solvents, including methanol, ethanol, acetone, as well as hexane (Toma et al., 2001). It is critical to select an appropriate extraction solvent in this operation. These solvents, which might easily disrupt the process are not used by researchers. After washing the sample with an organic solvent, the plant material is first broken down into tiny pieces using a centrifugal process. This step aids in the release of the essential components. A filtration technique is used to remove the solvent, and vacuum distillation removes the plant material. Fat-soluble and volatile compounds are among the components, which are extracted. After then, a different solvent (often alcohol) was used to extract the non-aromatic components. Eventually, second vacuum distillation is performed to remove the leftover solvent to obtain a pure mixture. The finished product is an herbal extract of essential oils of various compositions (Pateiro et al., 2018).

16.4.2 Innovative extraction technology Essential oils are inherently heat-labile because they are quickly inactivated by heat. Therefore, high temperature can change their structure (oxidation, isomerization ion, hydrolysis) and significantly disrupt their anti-microbial and antioxidant characteristics during conventional extraction techniques. Many alternative procedures have been established and proposed recently to solve these problems (Stratakos and Koidis, 2016). Also, the grouping of innovative techniques can increase the performance of the extraction process and improve its yield (Chemat et al., 2012a, b). 16.4.2.1 Supercritical fluid extraction To isolate volatile components from plant sources, this method employs supercritical fluids such as carbon dioxide. CO2 gas enters a supercritical state and becomes a liquid at low pressure and low temperature, diffusing through plants to eliminate aromatic chemicals. The following extract is clean, pure, and of excellent quality, with a scent comparable to that of the original plant before extraction (Koubaa et al., 2015). In this procedure, the material is heated to roughly 35°C due to which heat-sensitive chemicals that retain viability of final product which is important for maintaining the quality of the final product (Sharif et al., 2014). Due to its high infusibility and low viscosity, this technique is exceptionally efficient, despite its high cost. This technology has a faster extraction time and more flexibility than traditional approaches. By varying the temperature, pressure, and extraction time, the qualities of the produced essential oil can be selected. Furthermore, eliminating physiologically active chemicals is environmentally friendly (Gupta et al., 2012).

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16.4.2.2 Microwave-assisted extraction Traditional extraction methods (solvent extraction), microwave heating, and hydraulic distillation are combined in this extraction process (Stratakos and Koidis, 2016; Chemat et al., 2012a, b; Koubaa et al., 2016). A new microwave-assisted solvent-free extraction technique has also been devised, based on the principles of green extraction procedures (Li et al., 2013a, b). The sample is extracted without the use of water or organic solvents in this method. This procedure is regarded as superior to traditional methods since it can lower the amount of energy consumed in the extraction process and the extraction time (Flamini et al., 2007; Cardoso-Ugarte et al., 2013). Furthermore, because of its more significant quantity of aromatic chemicals, the essential oil prepared by this method is rarely considered more valuable (Lucchesi et al., 2007). 16.4.2.3 Ultrasonic assisted extraction This method uses a cavitation procedure to remove essential oils from rosewood plants, allowing solvents to penetrate deeper into the plants (Hashemi et al., 2016; Rosello´-Soto et al., 2015). Cavitation is the process of small areas expanding, forming, and growing without the presence of liquid. These areas will decompose to provide mechanical force as ambient pressure and temperature rise, permitting intracellular compounds such as essential oils (Li et al., 2014). By decreasing the thermal deterioration of essential oils at low temperatures, this technique can increase the quality of the extract (Vilkhu et al., 2008).

16.5 Chemical characterization Since the 1920s, people have extracted mahogany essential oil by steam distillation of the wood of the Amazon tree Aniba rosaeodora Ducke. The international perfume industry mainly uses the fragrance of rosewood. Therefore, this species has been included in the CITES (Convention on International Trade in Endangered Species of Wild Fauna and Flora) database as an extinct plant. The most crucial volatile compound in rosewood essential oil is a linalool with content between 78% and 93% (Maia et al., 2007; Lupe et al., 2008). Gas chromatography (GC) has limited separation capabilities for complex media (Pirok et al., 2018). Comprehensive two-dimensional gas chromatography (GC  GC) has become the preferred separation technique for composite matrices. The basic principle of chromatography is like conventional GC but has different requirements and characteristics (Mondello et al., 2008). There is literature on the application of GC  GC to analyze aromas, essential oils, and fragrances (Tranchida et al., 2010); however, there is currently no provision for the separation of Rosewood essential oils by GC  GC. Quadrupole mass spectrometer (qMS) is used as a detection method in GC  GC analysis (GC  GC-qMS). It is considered an exciting alternative to time-of-flight mass spectrometry (ToFMS) (Purcaro et al., 2010). QMS price In-expensive, fast scanning instruments are relatively suitable for GC  GC analysis (de Godoy et al., 2008; Silva et al., 2012). For compound identification, the temperatureprogrammed linear retention index (LTPRI) is used as a supporting tool. The procedure for calculating LTPRI is to use the “equivalent” value of the retention time (1tR) of the first dimension, which can be obtained from the total retention time (Bieri and Marriott, 2006).

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Therefore, the purpose of this work is to use GC  GC-qMS to chemically characterize rosewood essential oil from a 4-year-old plant pool to study its potential use as a source.

16.6 Characteristics of rosewood The botanical name of rosewood is Aniba rosaeodora, which is a tree belonging to the Laurel family, native to the Amazon and Guyana. Its wood is hard, fine-grained, pink in color, rigid and compact. It is used in carpentry and perfume. Brazil’s native Rosewood is ebony, while another legume family contains a wood species commonly called Rosewood, the most famous being Pterocarpus indicus, which belongs to Burmese Rosewood (Barbosa et al., 2021). Spesia populnea is also known as Malvaceae rosewood. Rosewood oil has a unique fragrance and is utilized in scents, and soaps. Linalool is 80% to 90% of its main ingredient and can be converted into many valuable derivatives in the perfume and fragrance industry (Maia and Moura˜o, 2016).

16.7 Applications of rosewood essential oil 16.7.1 Pharmacological applications Rosewood essential oil plays a vital role in the field of food and cosmetics. It is used as a fragrance fixer and is also used in the pharmaceutical industry (Bakkali et al., 2008). Rosewood essential oil is used as a medicinal ingredient in the pharmaceutical industry. The medicinal uses of rosewood oil are antibacterial, analgesic, preservative, antidepressant, anticonvulsant, aphrodisiac, cell stimulant, depressive insomnia, heartache, tissue regeneration, nourishment and brain, stimulation (Lawless, 2002). According to the manufacturer’s instructions, linalool is the main component of rosewood essential oil. Although the mechanism of linalool is not fully understood, the synergistic interaction of linalool and carvacrol plays a central role in the interaction of rosewood essential oil and thyme against E. coli. In glutamate-related seizures, linalool provides anticonvulsant, and sedative properties help inhibit adenylate cyclase in the retina of newborns and inhibit the effects of compounds in rodents (de Sousa et al., 2010; Sampaio et al., 2012). In the stomach, so-called mucosal lesions are gastric ulcers that form due to the imbalance of defensive and aggressive factors in the digestive tract (Li et al., 2013a, b). Taking antiinflammatory drugs and non-steroidal drugs and other factors such as drinking, smoking, Helicobacter pylori infection, and stress can also increase the risk of stomach ulcers. Linalool is effective against mucosal damage (Sowndhararajan and Kang 2013). The anti-cancer effect of mahogany essential oil on precancerous lesions and cancerous skin cells is enhanced (S
ur et al., 2011). It is reported in the literature that mahogany essential oil can be used as an antibacterial agent against Candida albicans, Escherichia coli, Listeria monocytogenes, Pseudomonas aeruginosa, Pseudomonas Vulgaris, Enterococcus faecalis, and Salmonella subspecies, Staphylococcus aureus, Serratia marcescens, and Enterobacter aerogenes. Rosewood essential oils inhibited these organisms at 0.12% and 2.0% (Chuesiang et al., 2019).

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16.7.2 Food applications Rosewood oil provides a distinct fragrance and long-lasting flavor, aroma, and foodstuff components. Rosewood oil is particularly essential in the food and cosmetic industries since it is added for aroma and designated by the Food and Drug Administration (FDA) as a generally recognized as safe (GRAS) component for use as a food additive. Rosewood essential oil is one of the most common aromatic oils that could be useful in the production and processing of poultry (Nair and Kollanoor Johny, 2017). Rosewood oil is golden yellow oil with distinct qualities in the woody fragrance family, such as a sweet, woody, balancing blend of floral and citrus smells (Curtis and Williams, 2001). Zellner et al. (2006) used olfactory analysis to depict Amazonian rosewood leaf oil and wood utilizing pleasant, fragrant, flowery, linalool, and green recordings. Citric, green, and woody tones distinguished the wood as well as leaf oils. Linalool is the primary component (80%–97%), which may be converted into various valuable derivatives for the cosmetics and taste industries (Lawless, 2002). Amazon reduced the market yield of rosewood oil sold on the global market by 0.7%–1.2%. Field distilleries’ poor yield (50%) justifies half of the natural oil production contained in the plants. According to the specimen literature, the leaf oil of A rosaeodora grew from 1.6% in September and October to 2.2% in March (Maia et al., 2007). The plants shed their old leaves between November and May, resulting in a higher concentration of rosewood oil. The highest amount of oil is produced in March, which coincides with the rainy season, resulting in higher Amazon participation. Many species of rosewood can be distinguished by wood collectors and oil producers based on their oil yield and look. They frequently identified tree affiliations based on physical characteristics such as leaf sizing, wood mass, and leaf, bark, wood odor, as well as types such as rosewood-Preciosa, “rosewood-itauba,” and “rosewood-tachi.”RosewoodPreciosa, rosewood-Tachi, rosewood-imbauba, and rosewood-itauba wood chips weigh 12–13 tons, 15–16 tons, and 18–20 tons, respectively, when distilled in a 180 L barrel of rosewood oil (Maia et al., 2007). Rosewood quality is affected by the age of the rosewood leaves as well as precipitation. Plants’ oxidative processes reveal that older leaves have more significant levels of substances such as terpinen-4-ol, linalool oxides, and terpineol. Water circulation in oil-containing cells is more significant in March (68.0%) and April (74.8%), resulting in a minor amount of linalool in the plant. Terpineol is an oxidized form of linalool that can be found in high concentrations in elder trunks. However, the oil producer cut the wood from the trunk near the ground to get maximum scaling, but this practice lowers the quality of the oil due to the more significant level of terpineol. As a result, cutting the trunk at chest height is the best technique to accomplish the desired result. Linalool concentrations of more than 20 g/L are accountable for the fruity-flowery taste seen in beers (Kaltner et al., 2003). Linalool is the major component in European-type sweet basil (Ocimum basilicum L.) oil, commonly utilized in the culinary business. Because of its aromatic leaves and pleasant odor, this oil is primarily used as seasoning for confectionery, meals, and drinks (Radulovic et al., 2013). Linalool has antibacterial properties that can be increased by mixing it with the optimum number of terpenes like—pinene and citral. In the presence of a local strain of Saccharomyces cerevisiae, linalool and -pinene (40–60 L/L) reduces the spoiling of soft orange drinks (Belletti et al., 2010).

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Due to the tasty and fragrant properties recognized by the US Food and Drug Administration, specific natural and artificial tastes high in linalool and its esters are encouraged in sweets, ice creams, beverages, and baked goods (Caputi and Aprea, 2011). The efficacy impacts of micro-capsules and various types of matrices, such as monitored release methods for their delayed volatilization, which are used as a pesticide against stored food pests, determine the stability of linalool (Lopez et al., 2012). (Chocolate beans, or Theobroma chocolate tree L, are high in linalool, primarily in the (S)-enantiomer form.) The examination of industrial products have revealed that the technological processes utilized in producing cocoabased manufactured goods do not result in substantial modifications in linalool’s original enantiomeric distribution. Rosewood oil is utilized as an effective antibacterial or as a food supplement in chicken processing plants. Immunostimulatory, antiviral, antibiotic, and antioxidant functions are valuable roles of essential oils (Nair et al., 2020).

16.8 Safety and toxicity of rosewood essential oils In people’s opinion, essential oils are harmless, natural, and long-lasting. The mahogany essential oil has much therapeutic potential. Still, care should ensure that an appropriate and sufficient carrier is used before applying it to sensitive areas (such as facial oil). Non-allergic people can experience the non-irritating and non-toxic effects of mahogany essential oil. Compounds of plant origin have larvicidal properties, which may help to change environmentally friendly larvicides (Pavela, 2015; Govindarajan et al., 2016). Linalool is the essential ingredient of rosewood essential oil and exhibits the weakest larvicidal properties. In a few cases, essential oils can be harmful as their use can cause rashes and toxicity if swallowed or absorbed through the skin. If someone swallows essential oils and a small amount enters the lungs, it is called aspiration pneumonia. When essential oils are mixed with other products and medicines, people will have multiple reactions. For example, someone is allergic to something, or it can cause an allergic reaction in other people. Children may be more susceptible to the harmful effects than adults because their livers are immature, and the skin layer is thinner. The essential oil preparation method describes its toxicity and interaction with other drugs due to other oils or alcohol. Ingesting essential oils can cause a rare poison called lavender poisoning. Lavender poisoning is believed to cause central nervous system depression, and toxicological analysis has confirmed its toxicity. Other conditions, such as anesthesia, decreased spontaneous motor activity, ataxia, and respiratory illnesses are caused due to acute linalool poisoning. Coma is also a fatal illness caused by the heavy consumption of acetone. Under toxic conditions, the acetone concentration varies from 100 to 2.5 g/L (Landelle et al., 2008).

16.9 Storage stability The solubility and bioavailability of essential oils are low, which is linked to the use of many other biological activities of EO (such as antifungals, antioxidants, and antibacterial). In the presence of these characteristics, the stability and effectiveness of essential oils were

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improved by combining EOs and CDs. Solubility and bioavailability have been improved using molecular inclusion techniques that prevent the destruction of essential oils (de Oliveira-Filho et al., 2018). Biological activities of the essential oil are affected by physical factors such as oxygen, light, and temperature. Compared to bulk oils, the readily available encapsulation of more stable essential oils can be used to minimize this complication (Levic et al., 2015). Due to the sensitivity of these compounds to temperature, oxygen, and light, the effectiveness of the main compounds in essential oils is affected (Rao et al., 2019). Polymer films used in packaging applications are directly combined with these compounds, and they can pass through the film and contaminate food (Kokina et al., 2019). Linalool is a reactive molecule in the short term. The model solution contains an aqueous solution of 0.025 M citric acid, which degrades 56% of linalool in 20 days at 24°C to produce certain compounds, such as 17% 3,7-dimethylact-1-ene-3,7-diol and 31% R-terpene Pinol (Bazemore et al., 2003).

16.10 Trade of rosewood oil Synthetic linalool has alleviated the rosewood oil in the low-scoring perfume market, where the rosewood trade volume has been declining since the 1960s. The rosewood trade volume on the international market has also declined due to Chinese home and leaf oil (Cinnamon camphor). It has replaced mahogany oil in mid-range cosmetics, household products, and perfumes. Nowadays, rosewood essential oil and its derivatives are mainly used in top perfumes and various perfumes as “bouquets.” They are 21 kg respectively. Due to reduced competition and supply, the export of rosewood oil has declined. At the peak of the industry, the output of rosewood oil usually accounts for an average of 75% of the total output. From 1945 to 1974, from 1997 to 1999, and from 2000 to 2003, the export volume of rosewood oil was 360 tons, 36 tons, and 26 tons, respectively, and therefore declined many times. Currently, the export market of rosewood oil is less than US$700,000 per year. Merchants from the United States are the leading importers of rosewood oil, accounting for an average of 63% of total sales from 1985 to 1987. Among them, Switzerland (13%) and France (16%) were buyers. They were subordinate to rosewood oil during this period. Although American traders maintained a leading position with 75% of the rosewood oil purchases, Switzerland was not a direct importer of the products, France contributed 10%, and the United Kingdom (11%) became the leading European buyer during 1997–1999. The United States is still the leading buyer recently, but Belgium also reiterated that it is the leading trader.

16.11 Conclusion In short, rosewood essential oil is considered to be an important due to its wide range of therapeutic as well as its utilization in the various food applications. As for as the extraction of rosewood essential oil is concerned, conventional as well as the innovative technologies are being used to get maximum yield without deteriorating the quality of the extracted essential

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oil that retains the viability of the bioactivity components, which are used for pharmacological applications. Furthermore, the scientists and researchers should focus for the improvement of the extraction yield by devising the novel technologies that ultimately enhanced its utilization in various applications. However, rosewood plant is grown on limited areas due to which the extracted essential oil is a bit expensive which results in minimizing its utilization in various food applications.

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de Godoy, L.A.F., Ferreira, E.C., Pedroso, M.P., Fidelis, C.H.D.V., Augusto, F., Poppi, R.J., 2008. Quantification of kerosene in gasoline by comprehensive two-dimensional gas chromatography and N-way multivariate analysis. Anal. Lett. 41 (9), 1603–1614. de Morais, L.A.S., 2009. Influ^encia dos fatores abio´ticos na composic¸a˜o quı´mica dos o´leos essenciais. In: Embrapa ´ guas de Lindo´ia, Meio Ambiente-Artigo em anais de congresso (ALICE). Congresso Brasileiro de Olericultura, A SP. Horticultura Brasileira, Brası´lia, DF, v. 27, n. 2, p. S3299-S3302, ago. 2009. CD-ROM. Suplemento. Trabalho apresentado no 49. de Oliveira-Filho, R.D., de Azevedo Moreira, R., Nogueira, N.A.P., 2018. Biological activities and pharmacological applications of Cyclodextrins complexed with essential oils and their volatile components: a systematic review. Curr. Pharm. Des. 24 (33), 3951–3963. de Sousa, D.P., No´brega, F.F., Santos, C.C., de Almeida, R.N., 2010. Anticonvulsant activity of the linalool enantiomers and racemate: investigation of chiral influence. Nat. Prod. Commun. 5 (12), 1934578X1000501201. Fidelis, C.H., Augusto, F., Sampaio, P.T., Krainovic, P.M., Barata, L.E., 2012. Chemical characterization of rosewood (Aniba rosaeodora Ducke) leaf essential oil by comprehensive two-dimensional gas chromatography coupled with quadrupole mass spectrometry. J. Essent. Oil Res. 24 (3), 245–251. Flamini, G., Tebano, M., Cioni, P.L., Ceccarini, L., Ricci, A.S., Longo, I., 2007. Comparison between the conventional method of extraction of essential oil of Laurus nobilis L. and a novel method which uses microwaves applied in situ, without resorting to an oven. J. Chromatogr. A 1143 (1–2), 36–40. Gavahian, M., Hashemi, S.M.B., Khaneghah, A.M., Tehrani, M.M., 2013. Ohmically extracted Zenyan essential oils as natural antioxidant in mayonnaise. Int. Food Res. J. 20 (6), 3189. Gavahian, M., Farahnaky, A., Sastry, S., 2016a. Ohmic-assisted hydrodistillation: a novel method for ethanol distillation. Food Bioprod. Process. 98, 44–49. Gavahian, M., Farahnaky, A., Shavezipur, M., Sastry, S., 2016b. Ethanol concentration of fermented broth by ohmicassisted hydrodistillation. Innovative Food Sci. Emerg. Technol. 35, 45–51. Giordani, R., Kaloustian, J., 2006. Action anticandidosique des huiles essentielles: leur utilisation concomitante avec des medicaments antifongiques. Phytotherapie 4 (3), 121–124. Govindarajan, M., Rajeswary, M., Benelli, G., 2016. Chemical composition, toxicity and non-target effects of Pinus kesiya essential oil: an eco-friendly and novel larvicide against malaria, dengue and lymphatic filariasis mosquito vectors. Ecotoxicol. Environ. Saf. 129, 85–90. Gupta, A., Naraniwal, M., Kothari, V., 2012. Modern extraction methods for preparation of bioactive plant extracts. Int. J. Appl. Nat. Sci. 1 (1), 8–26. Hashemi, S.M.B., Khaneghah, A.M., Akbarirad, H., 2016. The effects of amplitudes ultrasound-assisted solvent extraction and pretreatment time on the yield and quality of Pistacia khinjuk hull oil. J. Oleo Sci. 65 (9), 733–738. Hashemi, S.M.B., Nikmaram, N., Esteghlal, S., Khaneghah, A.M., Niakousari, M., Barba, F.J., Roohinejad, S., Koubaa, M., 2017. Efficiency of Ohmic assisted hydrodistillation for the extraction of essential oil from oregano (Origanum vulgare subsp. viride) spices. Innovative Food Sci. Emerg. Technol. 41, 172–178. Hashemi, S.M.B., Khaneghah, A.M., Koubaa, M., Barba, F.J., Abedi, E., Niakousari, M., Tavakoli, J., 2018. Extraction of essential oil from Aloysia citriodora Palau leaves using continuous and pulsed ultrasound: kinetics, antioxidant activity and antimicrobial properties. Process Biochem. 65, 197–204. Kaltner, D., Steinhaus, M., Mitter, W., Biendl, M., Schieberle, P., 2003. (R)-Linalool als Schl€ usselaromastoff f€ ur das Hopfenaroma in Bier und sein Verhalten w€ahrend der Bieralterung. Monatsschr. Brauwiss. 56 (11 12), 192–196. Kokina, M., Salevic, A., Kalusˇevic, A., Levic, S., Pantic, M., Pljevljakusˇic, D., Sˇavikin, K., Shamtsyan, M., Niksˇic, M., Nedovic, V., 2019. Characterization, antioxidant and antibacterial activity of essential oils and their encapsulation into biodegradable material followed by freeze drying. Food Technol. Biotechnol. 57 (2), 282–289. Koubaa, M., Barba, F.J., Mhemdi, H., Grimi, N., Koubaa, W., Vorobiev, E., 2015. Gas assisted mechanical expression (GAME) as a promising technology for oil and phenolic compound recovery from tiger nuts. Innovative Food Sci. Emerg. Technol. 32, 172–180. Koubaa, M., Mhemdi, H., Barba, F.J., Roohinejad, S., Greiner, R., Vorobiev, E., 2016. Oilseed treatment by ultrasounds and microwaves to improve oil yield and quality: an overview. Food Res. Int. 85, 59–66. Krainovic, P.M., de Almeida, D.R.A., da Veiga Junior, V.F., Sampaio, P.D.T.B., 2018. Changes in rosewood (Aniba rosaeodora Ducke) essential oil in response to management of commercial plantations in Central Amazonia. For. Ecol. Manag. 429, 143–157.

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Krainovic, P.M., Bastos, R.P., de Almeida, D.R., Junior, A.F.N., Sampaio, P.D.T.B., de Souza, L.A.G., de Souza Falca˜o, N.P., 2020. Effect of rosewood plantation chronosequence on soil attributes in Central Amazonia. Geoderma 357, 113952. Landelle, C., Francony, G., Sam-Laı¨, N.F., Gaillard, Y., Vincent, F., Wrobleski, I., Danel, V., 2008. Poisoning by lavandin extract in a 18-month-old boy. Clin. Toxicol. 46 (4), 279–281. Lawless, J., 2002. The Encyclopedia of Essential Oils. Thorsons, London. Levic, S., Lijakovic, I.P., Đorđevic, V., Rac, V., Rakic, V., Knudsen, T.Sˇ., Pavlovic, V., Bugarski, B., Nedovic, V., 2015. Characterization of sodium alginate/d-limonene emulsions and respective calcium alginate/d-limonene beads produced by electrostatic extrusion. Food Hydrocoll. 45, 111–123. Li, Y., Fabiano-Tixier, A.S., Vian, M.A., Chemat, F., 2013a. Solvent-free microwave extraction of bioactive compounds provides a tool for green analytical chemistry. TrAC Trends Anal. Chem. 47, 1–11. Li, W., Huang, H., Niu, X., Fan, T., Mu, Q., Li, H., 2013b. Protective effect of tetrahydrocoptisine against ethanolinduced gastric ulcer in mice. Toxicol. Appl. Pharmacol. 272 (1), 21–29. Li, Y., Fabiano-Tixier, A.S., Chemat, F., 2014. Essential Oils as Reagents in Green Chemistry. vol. 1 Springer International Publishing, Cham, Switzerland, pp. 71–78. Lopez, M.D., Maudhuit, A., Pascual-Villalobos, M.J., Poncelet, D., 2012. Development of formulations to improve the controlled-release of linalool to be applied as an insecticide. J. Agric. Food Chem. 60 (5), 1187–1192. Lucchesi, M.E., Smadja, J., Bradshaw, S., Louw, W., Chemat, F., 2007. Solvent free microwave extraction of Elletaria cardamomum L.: a multivariate study of a new technique for the extraction of essential oil. J. Food Eng. 79 (3), 1079–1086. Lupe, F., Souza, R., Barata, L., 2008. Seeking a sustainable alternative to Brazilian rosewood: linalool enantiomers in the essential oils of aromatic plants from Brazil: Aniba rosaeodora (rosewood), Lippia alba (erva Cidreira) and Ocimum basilicum (basil). Perfumer Flavorist 33 (7). Maia, J.G.S., Moura˜o, R.H.V., 2016. Amazon rosewood (Aniba rosaeodora Ducke) oils. In: Essential Oils in Food Preservation, Flavor and Safety. Academic Press, pp. 193–201. Maia, J.G.S., Andrade, E.H.A., Couto, H.A.R., Silva, A.C.M.D., Marx, F., Henke, C., 2007. Plant sources of Amazon rosewood oil. Quı´mica Nova 30, 1906–1910. Masango, P., 2005. Cleaner production of essential oils by steam distillation. J. Clean. Prod. 13 (8), 833–839. Mondello, L., Tranchida, P.Q., Dugo, P., Dugo, G., 2008. Comprehensive two-dimensional gas chromatography-mass spectrometry: a review. Mass Spectrom. Rev. 27 (2), 101–124. Nair, K.S., 2007. Tropical Forest Insect Pests: Ecology, Impact, and Management. Cambridge University Press. Nair, D.V., Kollanoor Johny, A., 2017. Food grade pimenta leaf essential oil reduces the attachment of Salmonella enterica Heidelberg (2011 ground Turkey outbreak isolate) on to Turkey skin. Front. Microbiol. 8, 2328. Nair, D.V.T., Dewi, G., Kollanoor-Johny, A., 2020. Chapter 18: The role of essential oils and other botanicals in optimizing gut function in poultry. In: Improving Gut Health in Poultry. Burleigh Dodd Publishing, Cambridge, pp. 463–492. Pateiro, M., Barba, F.J., Domı´nguez, R., Sant’Ana, A.S., Khaneghah, A.M., Gavahian, M., Go´mez, B., Lorenzo, J.M., 2018. Essential oils as natural additives to prevent oxidation reactions in meat and meat products: a review. Food Res. Int. 113, 156–166. Pavela, R., 2015. Essential oils for the development of eco-friendly mosquito larvicides: a review. Ind. Crop. Prod. 76, 174–187. Pirok, B.W., Stoll, D.R., Schoenmakers, P.J., 2018. Recent developments in two-dimensional liquid chromatography: fundamental improvements for practical applications. Anal. Chem. 91 (1), 240–263. Purcaro, G., Tranchida, P.Q., Ragonese, C., Conte, L., Dugo, P., Dugo, G., Mondello, L., 2010. Evaluation of a rapidscanning quadrupole mass spectrometer in an apolar ionic-liquid comprehensive two-dimensional gas chromatography system. Anal. Chem. 82 (20), 8583–8590. Radulovic, N.S., Blagojevic, P.D., Miltojevic, A.B., 2013. α-Linalool–a marker compound of forged/synthetic sweet basil (Ocimum basilicum L.) essential oils. J. Sci. Food Agric. 93 (13), 3292–3303. Rao, J., Chen, B., McClements, D.J., 2019. Improving the efficacy of essential oils as antimicrobials in foods: mechanisms of action. Annu. Rev. Food Sci. Technol. 10, 365–387. Reyes-Jurado, F., Franco-Vega, A., Ramı´rez-Corona, N., Palou, E., Lo´pez-Malo, A., 2015. Essential oils: antimicrobial activities, extraction methods, and their modeling. Food Eng. Rev. 7 (3), 275–297.

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Rosello´-Soto, E., Galanakis, C.M., Brncic, M., Orlien, V., Trujillo, F.J., Mawson, R., Knoerzer, K., Tiwari, B.K., Barba, F.J., 2015. Clean recovery of antioxidant compounds from plant foods, by-products and algae assisted by ultrasounds processing. Modeling approaches to optimize processing conditions. Trends Food Sci. Technol. 42 (2), 134–149. Sampaio, P.D.T.B., Barbosa, A.P., Vieira, G., Spironello, W.R., Ferraz, I.D.K., Camargo, J.L., Quisen, R.C., 2003. Silvicultura do pau rosa (Aniba rosaeodora Ducke). In: Higuchi, N., dos Santos, J., Sampaio, P.D.T.B., Marenco, R.A., Ferraz, J., de Sales, P.C., Saito, M., Matsumoto, S. (Eds.), Embrapa Amaz^ onia Ocidental-Resumo em anais de congresso (ALICE). Manaus, Inpa. (Org.). Projeto Jacaranda fase II: pesquisas florestais na Amaz^ onia Central. Sampaio, L.D.F.S., Maia, J.G.S., de Parijo´s, A.M., de Souza, R.Z., Barata, L.E.S., 2012. Linalool from rosewood (Aniba rosaeodora Ducke) oil inhibits adenylate cyclase in the retina, contributing to understanding its biological activity. Phytother. Res. 26 (1), 73–77. Sharif, K.M., Rahman, M.M., Azmir, J., Mohamed, A., Jahurul, M.H.A., Sahena, F., Zaidul, I.S.M., 2014. Experimental design of supercritical fluid extraction–a review. J. Food Eng. 124, 105–116. Silva, B.J.G., Tranchida, P.Q., Purcaro, G., Queiroz, M.E.C., Mondello, L., Lanc¸as, F.M., 2012. Evaluation of comprehensive two-dimensional gas chromatography coupled to rapid scanning quadrupole mass spectrometry for quantitative analysis. J. Chromatogr. A 1255, 177–183. S
ur, J., Marrot, L., Perez, P., Iraqui, I., Kienda, G., Dardalhon, M., Meunier, J.R., Averbeck, D., Huang, M.E., 2011. Selective cytotoxicity of Aniba rosaeodora essential oil towards epidermoid cancer cells through induction of apoptosis. Mutat. Res. Genet. Toxicol. Environ. Mutagen. 718 (1–2), 24–32. Sowndhararajan, K., Kang, S.C., 2013. Protective effect of ethyl acetate fraction of Acacia ferruginea DC. Against ethanol-induced gastric ulcer in rats. J. Ethnopharmacol. 148 (1), 175–181. Stratakos, A.C., Koidis, A., 2016. Methods for extracting essential oils. In: Essential Oils in Food Preservation, Flavor and Safety. Academic Press, pp. 31–38. Toma, M., Vinatoru, M., Paniwnyk, L., Mason, T.J., 2001. Investigation of the effects of ultrasound on vegetal tissues during solvent extraction. Ultrason. Sonochem. 8 (2), 137–142. Tongnuanchan, P., Benjakul, S., 2014. Essential oils: extraction, bioactivities, and their uses for food preservation. J. Food Sci. 79 (7), R1231–R1249. Tranchida, P.Q., Shellie, R.A., Purcaro, G., Conte, L.S., Dugo, P., Dugo, G., Mondello, L., 2010. Analysis of fresh and aged tea tree essential oils by using GC GC-qMS. J. Chromatogr. Sci. 48 (4), 262–266. Tsayem Demaze, M., 2008. Croissance demographique, pression foncie`re et insertion territoriale par les abattis en Guyane franc¸aise. Norois. Environnement, Amenagement, Societe 206, 111–127. Useche, F.L., Valencia, W.H., Viera, G., 2011. Desarrollo inicial de Aniba rosaeodora Ducke en claros artificiales de bosque primario, Amazonia Central Brasilera. Ingenierı´as Amazonia 4 (1). Vian, M.A., Fernandez, X., Visinoni, F., Chemat, F., 2008. Microwave hydrodiffusion and gravity, a new technique for extraction of essential oils. J. Chromatogr. A 1190 (1–2), 14–17. Vilkhu, K., Mawson, R., Simons, L., Bates, D., 2008. Applications and opportunities for ultrasound assisted extraction in the food industry—a review. Innovative Food Sci. Emerg. Technol. 9 (2), 161–169.

C H A P T E R

17 Juniper essential oil: An overview of bioactive compounds and functional aspects Tabussam Tufaila, Huma Bader Ul Aina, Arooj Saeeda, Muhammad Imrana,b, Shahnai Basharata, and Gulzar Ahmad Nayikc a

University Institute of Diet and Nutritional Sciences, The University of Lahore, Lahore, Pakistan b Department of Food Science, Institute of Home and Food Sciences, Faculty of Life Sciences, Government College University Faisalabad, Faisalabad, Pakistan cDepartment of Food Science & Technology, Government Degree College Shopian, Srinagar, Jammu & Kashmir, India

17.1 Introduction Apart from being the essential foundations of food on Earth, the plant world has provided humans with a range of cures for various ailments. “Ebers Papyrus, ancient Egyptian medicinal repository” has a record and proof of plants being used as remedies dating back to 1500 BCE. Nonetheless, the Egyptians were not the only people who used herbal therapy at the time. Around 1000 plant-derived compounds have been discovered in Mesopotamia, going back to 2600 BCE. Because plants occur in every habitable habitat and are sedentary, they are exposed to a variety of pressures and difficulties. As a result, plants have evolved complex secondary molecules to protect themselves from animal assaults and to withstand environmental insults. These compounds have extra activities that allow plants to produce specific perfumes, hues, and even toxicity. Early human nations must have found therapeutic plants by trial and error, as illness symptoms would have demanded. Medicinal plants have therefore become the most abundant bioresource of traditional medicine pharmaceuticals, nutraceuticals, contemporary medicine intermediates, and chemical scaffolds for synthetic drugs. Plant-based medications account for over a fourth of all FDA

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00020-7

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Copyright # 2023 Elsevier Inc. All rights reserved.

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17. Juniper essential oil

and/or European Medical Agency (EMA)-approved medications, with a long list of really well drugs. Medications for various disorders are ingested in the form of crude preparations (extracts, tinctures, and essential oils), which include a wide range of chemicals with powerful and specialized biological effects. Juniperus is a genus of evergreen gymnosperms from the Cupressaceae family that has a huge spatial distribution in Pakistan, India, China, South Asia, Central America, Africa, and the Arctic regions (Tavankar, 2015). After pines, juniper species are the second most prevalent conifer on the planet. Juniper varieties, particularly Juniper communis L., Juniper excelsa, and Juniper communisvar saxatilispallas, are common in Himalayan highland vegetation and may be found at elevations ranging from 1500 to 4000 m. Juniper leaves may last for many years and can even be left on the stalk after drying for an infinite amount of time (Kunwar et al., 2009). Juniper flowers are typically unisexual, and their breeding system contains distinct phases (Gruwez et al., 2013). Only a few species, however, bloom of both sexes on the same trees. The trees may be grown from seeds, which can last for many years if stored correctly in a cold, dry location. Juniperus communis, Juniperus recurve, Juniperus indica, and Juniperus squamata are all common Juniper species in the Himalayan zone (Mao et al., 2010). Table 17.1 shows that Juniper crude has long been prized in medicine for its therapeutic and aesthetic properties. Pine tree oil has been used in soap, room spray, disinfection, fragrance, and other related technologies for millennia. In fact, juniper is prized in paper production for its tensile strength and longevity. With 67 species, dwarf varieties are the second most enduring group of flowering greenery on the planet, behind cedar. Themes that emerged can be found in temperate areas of Eastern North America, as well as in tropical mountains. Juniper Phoenicia, for instance, maybe distributed throughout the Humid tropics, the Isles of Scilly, and regions of Africa. The Greece juniper, J. excelsus, is the world’s second-biggest forest and thus the world’s oldest living species (Loureiro et al., 2007). The spiny Portugal cedar Juniperus excelsa, on the other hand, is the world’s second-largest forest and the world’s most experienced fruiting species (Loureiro et al., 2007). Consequently, J. navicularis, or Spanish thorny hawthorn, is an isolated dioecious TABLE 17.1 Distribution of different Juniperus species in different countries. Species

Nativity

Altitude

References

Juniperus bermudiana

Bermuda

1700–3400

Tavankar (2015), Kunwar et al. (2009)

Juniperus chinensis

China

1700–3400

Juniperus communis

Northern Hemisphere

2500–4500

Juniperus deppeana

Mexico

1700–3400

Juniperus oxycedrus

Syria

1700–3400

Juniperus phoenica

Algeria

1700–3400

Juniperus procera

Kenya

1700–3400

Juniperus recurva

Himalayas

1700–3400

Juniperus scopulorum

USA

1700–3400

17.1 Introduction

417

shrub first from Making comments advance sands of the west Portuguese coast. Juniperus species, on the whole, are resistant to drought and adapt well to changing circumstances. Juniperus phoenicea is just a little tree that fills inefficiently in areas with a long dry period and high-temperature variations (Zaidi et al., 2012). Junipers have a significant biological role by protecting the dirt from decomposition. Eastern cottonwood J. polycarpic, which grows at high elevations, above 1000 m on sandy rock soil, reduces soil erosion, wind erosion, and barren green building in the arid parts of Iran’s undeveloped land (Castro et al., 2011). Juniper wood has a low cost of production in many nations, and it is used to make lead pencils, build structures, and a variety of exterior systems, among other things. Global warming may have harmed colonies of certain juniper species in recent years. Some types of juniper are rare or imperiled. J. Navicularis (a virulent illness and endangered animals in Portugal), Spanish juniper J. Consists of three main (an extraordinary, extinct animal in North Africa), Balearic juniper J. Cedrus (an endemic native to the Canary Islands in Spain), J. Robusta, and prevalent juniper J. Camellia are some of the species (Ahani et al., 2013). Despite its widespread distribution in East Africa, south and central Asia, and south eastern Europe, J. Excelsa is in danger of death. On the other hand, insufficient regeneration capability has put a few J. Curcuma communities in certain insular locations or Turkey (Al-Ramamneh et al., 2012). As a result, attempts have been devoted to recovering juniper forests using unique sexual or asexual diffusion mechanisms. Due to restricted seed yield, lower health charge, technical efficiency dormancy, and seed quality fetal activity, juniper breeding is commonly hampered (Momeni et al., 2018). Under present climate change and growing human fear, this prospect can be highly concerning, specifically if the cedar stock is declining (Cantos et al., 1998). Juniper stems and cones, which are often used as seasonings, might be utilized to develop new food carriers with superior nutritional properties. As a result, because phenolic acids and terpenes are ingested on a regular basis as a result of such an early plant diet, they are appealing as a dietary ingredient with significant antioxidative. The major component, phoenicea, had already been used (Negussie, 1997). Juniper blooms are often extensively used as a culinary spice, especially in the pickling of game birds and meat. Traditional cuisines include vegetable meals with “bigos” and “sauerkraut,” Polish sausage “kiebasajaowcowa,” and turkey jam prepared from common juniper (J. communis) seed cones (Kocer et al., 2011). Crucial aspects of their products include the Italian wine “Jeanparino,” the Serbian brand “Kolikova,” and the Polish beer “PivoKozhiko.” In particular, cedar variations, notably needle or leaf distillation and lavender oil, seed cones, and wood are recognized for their numerous pharmacological qualities in ancient Eurasian pharmacists (Al-Ramamneh et al., 2017). The small seed of the crown formed by certain types of deciduous trees is known as wood raspberries. It’s conical with fleshy, multicolored sections that give it the impression of fruit, denying the reality that it isn’t. A few kinds’ cones, especially juniper communities, are used as a pepper, especially in Traditional dishes, but for those with a distinct flavor. Hessian bags are commonly used for delivery. Various ingredients are frequently used in the preparation of these meals. The fruit has a low water content, which means they cost a lot to smash. For storing, single-layer bag tires are perfect (Negussie, 1997). They’re usually offered whole or smashed dry, but they’re also available glistening. Bear in mind that there are many different varieties of junipers, and not all of species are healthy. Juniperus communis fruits are commonly used in cooking. The cedar berry

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is a tasty spice which may be used in a wide range of recipes. Juniper-based wine is made by boiling juniper berry in freshwater and condensing the resulting “wine.” In Eastern Europe, it is known as juniper brandy (Daneshvar et al., 2016). In hard liquor such as wines and gin, juniper goods are utilized as a major flavor. Fruit sauce is a traditional and delicious alternative for rabbit, deer fowl, pheasant, calf, antlers, and other wild meats. The essential oil derived from steamed berries might be colorless, yellow, or pale green in hue. Chemical components include terpenoids and aromatic compounds like sesquiterpene and carotene. Juniper charcoal has traditionally been a significant element for Navajo people (Hazubska-Przybyl, 2019). Critical oils and extracts from various components of the juniper species have been utilized for medical and cosmetic purposes for ages. In fact, juniper hardwood is noted for its resilience in the woodworking business. Dried juniper berries are used as a seasoning in Northern European cuisine to give the meat a distinct flavor, and ripe fruit is also an important element in a few wines, such as gin, citrus fruits, and ginepro (Marbet et al., 2008). Despite the fact that some juniper species are poisonous, throughout the world in many nations they are commonly utilized in folk medicine. On the other hand, timber oil is still being used nowadays to smell cleaners, preparations, home perfumes, sanitizers, and other similar goods (Sokovic et al., 2004). It accomplishes delicious soups and stews, broths, and chowders in crushed or whole form, as well as hog, hare, venison, bull, and pigeons. They’re also delicious in desserts such as fruit loops (Lesjak et al., 2014). In uncommon juniper’s berries, cones have a strong spicy fragrance and a bittersweet flavor. When using venison, they eliminate the gamey flavor. They’re also generally implemented to flavor sour, as well as spice recipes and cooking procedures (Miceli et al., 2011). Juniper oil is derived from certain pieces of trees and is used in fragrances as well as medications such as antagonists. Many aromatic wood species are used to make closets, wooden poles, and devices (Cantrell et al., 2014). The berries’ external layers are flavorless; therefore, they’re almost always slightly overpowered and used as a spice. They’re utilized fresh and dried, although their flavor and odor are strongest just after harvesting and fade with time (Orhan, 2019). Although acid violet seedlings are too bitter to eat raw, they must be dried before they may be utilized as a food ingredient in numerous sectors. Before being used in cooking, berries are shot or mashed to enhance flavor. Within the past, juniper Phoenicia, cedar nuts, and compounds were discovered as Oxycedrus that’s not developed in Egypt in Tutankhamun’s grave (Bais et al., 2014a, b). These are fruits of ancient Greece. Until they were listed as a meal, the Persians utilized the fruits as a medicine. Fruits were used in numerous Athletic competitions because the Grecian felt thought they improved the performers’ vitality and capability. The Greeks substituted cedar berries instead of pricey lengthy peppercorns brought via Indian as reduced home usage. Herbs sprout on bushes that “glance like our deciduous trees,” as Ptolemy incorrectly said (Tavares and Seca, 2018). Juniper woods reduce soil limitation by raw resources and timber, pasture, and CO2 and other inorganic compounds, while also improving soil quality. It refreshes aquifers, increases the groundwater level in the winter, decreases drought via photosynthesis, filters the atmosphere via oxidation, and controls the area (Sarangzai et al., 2012). Additionally, not only do these trees give modest financial, aesthetically, and atmospheric advantages to indigenous peoples, but they also supply modest financial, visual style, holiday, and meteorological advantages to U.S. citizens and across the planet. They support a diverse spectrum of living

17.3 Extraction techniques (distillation)

419

organisms from various groups, genera, and kinds, and ultimately regulate a variety of natural occurrences. The inhabitants obtained non-woody commodities such as disease and aromatic hardwoods, trying to cover barks, tonic necessary berries, and medicinal plants for conventional treatments. These forests have an important impact in carbon capture in plants as part of the new forestry cycle (Raina et al., 2019).

17.2 Production and composition The crude extract is a complex combination of dangerous chemicals, mostly aromatic compounds, with pleasant aroma properties and a unique odor. Natural oils safeguard crops from predators as well as germs and parasites. Fragrance oils, hygiene, contribute to making; personal care products, agriculture, and in meditation. Regarding the customer concerns about sodium benzoate, EOs are displacing manufactured antimicrobials and inorganic food ingredients’ bacteriostatic characteristics. A variety of pharmacological actions have indeed been attributed to them, including reactive, anticancer, generally pro, and antibacterial. The primary chemicals described in natural ingredients include aromatics, terpenoids, polyphenolic compounds, alcohols, -myrcene, -thujone, glycoside acetateethers, citronellol, curcumin, geraniol, terpineol, and ketones. Terpene hydrocarbons are the major ingredients of juniper lavender oil, regardless of their nature. According to Angioni et al. (2003), alpha-pinene, β-, delta-3-carene, terpinene, terpenes, early access, luteolin, and D-germacrene are the primary chemicals found in juniper natural ingredients. It is not usually a good provider of the most important nutrients, but it does contain lots of oil, which Awareness dissemination on the surface of leaves. Berries are a fruit that contains lavender oil (0.5% in shining fruits and 2% in dried fruits), sugar (15%– 30%), resin (10%), catechins (3% to 5%), natural acidity, Terpenic acid, gums, anthocyanins, waxes, leucoanthocyanidin and polyphenols, and other phenolic components. Bioflavonoids, flavone, flavonols, flavones, flavonoids (quercetin, isoquercetin), and minerals may all be found in cedar fruits (diet C) (McCabe et al., 2005).

17.3 Extraction techniques (distillation) Crude extract may be extracted via juniper fruits or branches using a variety of procedures. The production of essential oils from juniper fruits and branches is affected by the soil’s geographic area, maturity, wind patterns (heat, duration of sunshine, flowering time time), as well as other variables. Oil yields ranged between 0.5% and 2.5% (fruits) and 0.2%–1.0% (seeds) (needles). Volatile oils ingredients may be obtained from plant sources using a variety of ways. The mixture of lubricants extracted from juniper fruits or tips by solvent distillery (SDE) and vapor phase removals (SFE), as well as the analytical technique (HS-SPME), have been investigated. Microwave exploitation (MW) is becoming more popular for recovering lavender oil (EOs). The method of microwave-aided but instead (MWHD) is a relatively modern technology for recovering water vapor. The sample quickly approaches heat capacity, resulting in a quick evacuation.

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17.4 Applications Juniperus communis is now the most current addition to the list of Juniperus species with therapeutic use. Its fruits and apical portions are frequently employed by United States indigenous peoples for a variety of therapeutic uses, ranging from respiratory diseases to gynecology issues. It might be used as a tonic or anesthetic. Juniperus communis is used by Indians, such as the Navajo, to cure illness, asthma, and diabetes. The berries of Juniperus communis are used to cure acutely and chronically cystitis, albuminuria, and leucorrhoea in Hinduism. It’s also a laxative, demulcent, antibacterial, gastrointestinal, previously appeared, and generally pro. Juniperus communis dried ripening fruits are also included in the Monograph, implying that they have therapeutic use. Juniperus virginiana and Juniperus procera are less well-known varieties. Juniperus virginiana seeds are usually applied in Europe and were claimed to have antipyretic and purgative capabilities. Furthermore, the tree’s leaves have diuretic properties. Juniperus oxycedrus plants and strawberries are used in Turkey as a traditional treatment for blood glucose control. J. excelsa is also used to treat colds and bronchitis in Turkey, while Juniperus foetidissima shoots are used to treat coughs and are highly contagious. Juniperus foetidissima fruits have been used to treat the hardening of tendons. Juniperus sabina is used to treat gastrointestinal problems, psoriasis, and ulcers. It’s used as a stimulant and in the treatment of diseases. In Iranian, the leaves and seeds are used as antifertility, antioxidants, and antimutagenic drugs. In Tunisian, an infusion of J. phoenicea leaves and stems is used to treat skin problems, inflammation, arthritis, alcoholism, and gastroenteritis. Juniperus indica nuts are being used to cure renal issues in Nepal, while its leaves are used to remedy coughs, colds, immobility, and even to enhance the immune system. The genus Juniper is very well chief constituent oil, which is widely utilized in conventional healers.

17.5 Health claims The perennial fragrant shrub Juniperus vulgaris L. has a significant medicinal promise in the cure of people’s ailments. Fragrant oils, carbohydrates, varnishes, catechin, oxalic compound, leucoanthocyanidin terpenic acids, alkaloids, polyphenols, tannins, gums, glucans, beeswax, and other compounds are abundant in the plant. They are used as antidiabetes, antibiotics, and for the cure of different and immunological illnesses for centuries. Juniper crude oil and extracts have been shown to have oxidative, antibiotic, and other activities in studies. In laboratory animals, strawberries have also been discovered to have generally pro, apoptotic, hypoglycemia, and antihyperlipidemic properties. Furthermore, due to its high antioxidant impact, essential oil inclusion in cured meat slowed antioxidant activity, which somewhat enhanced meat productivity but also increased shelf life. As a result, catechins like juniper could be utilized instead of synthetic antioxidants to extend the shelf life of processed meat. New well-designed plant and livestock clinical trials employing

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well-characterized J. vulgaris extract or oil are needed to develop more data that really can justify the use of this food substance as nutrition (Raina et al., 2019).

17.5.1 Antioxidant activity According to recent research, the preparation of bark of mango stem is more efficient in lowering the excessive production of combative oxygen varieties (ROS) and related reactive tissue damage in vivo than carotene, vitamin E, and vitamin C. As a result, the antioxidant potential of mangiferin was investigated both in vitro and in vivo. As a result, the antioxidant properties of mangiferin were investigated in vitro and in vivo. It has been demonstrated to have antioxidant properties against DPPH. Membrane lipid peroxidation was increased by Fe3+ reductive activity and hydroxyl radicals, t-butyl hydroperoxide, and antimycin A-induced H2O2 production. Thiobarbituric acid reactive substances (TBARS) determined. The activity of antioxidants in the water emulsion system/linoleic acid indicated that it has more advanced activity than quercetin. Various fundamental researches have approved which evaluated that mangiferin have different mechanism from the standard hydroxyl radical scavengers, By complexing Fe3+ or boosting Fe2+ autoxidation, iron is kept in its ferric state. Mangiferin’s antioxidant action in vitro is linked to its iron-binding characteristics and not alone to its free radical scavenging ability. Amount of mitochondria-generated reactive oxygen species enhanced by Ca2+, for the production of quinoid derivatives it combines with mangiferin, which combines to the most vulnerable mitochondrial thiol groups, therefore generating mitochondrial absorptivity evolution. It possibly appears that mangiferin has their free radical scavenging activity which modifies protection of antioxidant to the thiol arylation.

17.5.2 Hepatoprotective activity In rats, the antioxidative function of J. vulgaris was tested by administering CCl4 for 9 days. Especially compared with the control group, transaminase acetoacetic assurance ensures (SGOT), glutathione-s pyruvic transaminase (SGPT), total bilirubin (TB), and alkaline phosphatase (ALP) levels increased significantly in the CCl4 therapy group. The levels of SGPT, SGOT, TB, and ALP in the silymarin-treated group were significantly lower. Neurotoxic effects caused by CCl4 resulted in abnormally high levels of SGOT, SGPT, ALP, and bilirubin.

17.5.3 Antiinflammatory activity Isolated cells and enzymatic tests were used to investigate the antiinflammatory efficacy of J. communis fruit. At 0.2 mg/mL in the prostaglandin test and 0.25 mg/mL in the thrombo promoting factor (PAF) test, the plant demonstrated varying degrees of action (aqueous extract). Prostacyclin reduction was 55% and PAF-exocytosis inhibition was 78% in J. communis. The

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PAF activity was evaluated by generating fibrinolytic efflux. Paper chromatography was used to examine all plant extracts, which were rinsed with diethyl ether (Tunon et al., 1995). Many in vitro and in vivo investigations released in recent decades have given scientific justification of Juniperus taxa’s generally pro function. In terms of improvement, the very first varieties are certified (Tunon et al., 1995) used in vitro research to assess the generally pro efficacy of 59 alcoholic extracts. The juniper isolate was demonstrated to just be effective for both tests utilized yet again. Akkol et al. (2009) investigated the generally pro effects of five Ottoman Juniperus genera ethyl acetate extract and leaf extract in a licorice extract and PGE2-induced hind paw edema paradigm, providing empirical proof for their original role. Kalinkevich et al. (2014) also included methanolic derived from Pinus communis L. in their in vitro investigation evaluating the generally pro effects of 133 trees, veggies, berries, and fungi endemic to Moscow. According to their findings, juniper extracts have an acceptable antiinflammatory ability (Table 17.2).

17.5.4 Antidiabetic activity Diabetes is becoming a major public health issue, with type 2 diabetes responsible for more than 80% of diabetes. The capacity to boost glucose absorption into big target tissues, such as skeletal muscle and adipose tissue, is impaired in this kind of diabetes. Heart disease (hypertension, retinal damage, and atherosclerosis), fatty liver disease, dyslipidemia, and renal disease have all been associated with elevated blood glucose and insulin levels. While drugs with many pharmacological processes are the most effective type 2 diabetic therapy, they cannot completely prevent disease onset. As a result, advanced and efficient medications are desperately needed. Mangiferin medication was recently found to be effective in diabetic mice produced by streptozotocin (STZ). Following a 30-day oral therapy with 40 mg/kg mangiferin, biochemical, toxicological, and hematological parameters were assessed. Manganese treatment reduced glycosylated hemoglobin, transferases (AST), acid phosphatase (ALP), and aspartate blood glucose (ALT) levels in diabetic mice. Furthermore, in super high nutrition and STZ-induced insulin-dependent incretin rat model, mangiferin has been shown to. Along with reducing insulin resistance to manganese, improving cell functions, lowering serum levels of triglycerides (TG), lowering

TABLE 17.2

Origin of Juniper.

Kingdom

Plantae

Division

Spermatophyta

class

Pinopsida

Order

Pinales

Family

Cupressaceae

Genus

Juniper

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levels of lipid (TC), and lipoprotein cholesterol (LDL-C). Along with the atherogenic index, it has shown to reduce liver TG and hepatic TC content. Glycogen levels in the liver also increased. These findings support the idea that megaphones may successfully increase insulin sensitivity in the treatment of type 2 diabetes with metabolic abnormalities. Similarly, various studies showed that models of manganese in diabetic rats generally have pro-, antihyperlipidemic, and antiatherogenic benefits. As a result of the increase in islet function produced by mangiferin, our first task was to conduct 70% partial pancreatectomy (PPx) in mice to understand the antidiabetic action of mangiferin. Mangiferin is helpful in the treatment of diabetes. It can be used alone or in combination with other therapeutic phytochemicals, such as manganese calcium salts, norepinephrine, and manganese halogenated hydrocarbons. It has been reported that mangiferin A and neomycin are involved in the prevention of diabetes and treatment medications. Mangiferin potassium salt was used to lower glucose, plasma insulin, and fat levels, and it was suggested as an insulin sensitizer. Moreover, this salt has the potential to improve mangiferin accessibility and solubility. Norathyriol, an aglycon of manganese, is effective in lowering blood sugar levels. Mangiferin aglycon propionate compounds proved to be more hypoglycemic than mangiferin aglycon and mangiferin. These chemicals did not cause any toxic or harmful side effects in rat models. Foliamangiferosides were discovered in an invention, and their use in a pharmaceutical composition to reduce the activity of alpha-glucosides was described. These chemicals have the potential to work in the treatment of diabetes. Another active manganese molecule was identified, and it significantly inhibited the protein tyrosine phosphatase 1B (PTP1B). This chemical can be used to develop drugs to treat type 2 diabetes and other PTP 1 B-related disorders. Army Medical College, No. 2 (2007–2008). Mangiferin has been shown in two patents to inhibit glycogenesis in the liver, which also inhibits the increase in blood hemoglobin HbA1c. Mangiferin, a carbonic acid of the tetrahydroxy pyridine found in many plants, was reported in an investigation. According to the study, mangiferin was used to regulate the expression of the encapsulating protein-2 (UCP2) gene to control nephridia tissue and to prevent and treat type 2 diabetes mellitus. This gene has long been associated with hyperinsulinemia and obesity (Nanjing Univ., 2007). Another patented detailed compound for the manufacture of type 2 diabetes drugs containing manganese and barberry in a weight ratio of 1:0.1 to 1:20. This formula was developed to treat and prevent the long-term consequences of type 2 diabetes.

17.5.5 Antihyperlipidemic activity The antihypercholesterolemic activity of J. vulgaris fruits oil has indeed been studied. The impact of physicochemical markers and histopathologic changes on renal tissue were studied. For this investigation, normal Albino rats weighing 200–250 g were employed. The animals were separated into five groups: the first one was the controlled study, which was given regular pellet food. The group b was fed a granular meal having 2 percentage fat, and the third was the J. group of people who share (JCL) group, which was further separated into three categories: Fifty JCL, Hundred JCL, as well as Two hundred JCL subgroups, which were supplied 50, 100, and 200 mg/kg J. vulgaris, respectively. Within a week of 30 days, plasma and hepatic and renal samples were collected, and histopathology analyses were performed.

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Blood ammonium nitrate (BUN) and creatine are 200 mg/kg JCL sample. Ox-LDL concentrations increased in the saturated fat treatment. There was no massive rise in Ox-LDL levels when saturated fat was provided together with 200 mg/kg J. vulgaris. As a result, the investigation revealed that it has antihypercholesterolemic properties (Akdogan et al., 2012).

17.5.6 Analgesic activity Banerjee and colleagues used methanolic extract to study the analgesic efficacy of J. communis. The analgesic efficacy of the methanolic was tested at doses of 100 mg/kg and 200 mg/kg. The standard was acetylsalicylic acid (100 mg/kg). Alternative methods, including as the present experiment, acetic acid induced screaming, and head flicks tests, were used to analyses the extract in vivo. When opposed to ibuprofen (P 0.01), J. communis demonstrated a substantial (P 0.01). The antiinflammatory and analgesic efficacy is confirmed by the inhibiting effect of naltrexone (2 mg/kg i.p.). The species has demonstrated strong antinociceptive efficacy, and it has been proved that J. vulgaris leaf extracts act laterally and regionally (Banerjee et al., 2012). With a diverse set of pharmacological effects, A glycol chemical agent is mangiferin. It will have the capacity to decrease irritation in several tissues by blocking pattern recognition receptors, modifying cell wave channels, activating decomposition, lowering immune cell production, and preserving gut barrier function, all of which help to treat cancer.

17.5.7 Antibacterial activity Using the dilution method, the isolated leaves of J. communis (butanol, alcoholic, formaldehyde, and hexane aqueous) were tested against five deadly resistant strains (Alternaria chrysanthemi, Vibrio cholera, Bacillus cereus, Agrobacterium tumefaciens, and Xanthomonas segment). Except for aqueous extract, all extracts of J. communis plants were shown to be efficient against pathogenic organisms. In comparison to another extracts, the aqueous extracts demonstrated greater activity (hexane > ethanol > alcohol > chloroform extract). When contrasted to common antibiotics (piperacillin 10 μg and Flagyl 15 μg), the methanol extracts of J. vulgaris were shown to be highly helpful (Sati and Joshi, 2010).

17.5.8 Antimicrobial activity J. vulgaris fruits and vegetables exhibit antibacterial action, and their crude oil was studied using GC-FID, GC–MS. Its petroleum was evaluated for antibacterial action against E. coli, Bacterial infections, morphologically similar alvei, and Pseudomonas fluorescens, among other bacteria. The width of the negative control surrounding the disc was measured using a DMF mixture with three distinct doses of essential oil (1, 3, and 5 mg/mL) applied to the disc. The column chromatography examination of J. set of social lavender oil revealed 41 compounds, accounting for 96% of the oil’s overall makeup-cardinal (1.6%), -pinene (36.2%), -myrcene (21.1%), -humulene (1.5%), epi-bisabolol (1.3%), biochanin D (2.2%), spathulenol (1.4%), and biochanin B (1.4%) were the primary chemical elements in J. communis (1.1%). The elemental composition of J. communis from Kosova’s east region is proposed in this research.

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Except for Pseudomonas aeruginosa, which is sensitive to J. communis, J. humilis was active toward E. coli, bacterial infections, and morphologically similar alvei (Pepeljnjak et al., 2005).

17.5.9 Antifungal activity Manufacture of pharmaceuticals was used to extract the essential oil from the aerial portions of J. communis, yielding 0.1% and 0.3% yield. The oils were then evaluated in vitro for antifungal efficacy against Rhizoctonia solani and Rhizopus stolonifer, two fungi. J. communis essential oils had antimicrobial activities against several fungi: J. communicare (EC50: 0.554 mg/mL) and J. communis (EC50: 0.704 mg/mL). A high amount of oxygenation monoterpenes in J. vulgaris is primarily responsible for its antimicrobial effect (Modnicki and Łabędzka, 2009).

17.5.10 Antimalarial activity The active compounds of 8 trees communicate (Calendula Vulgaris, Tagetes camellia, Angustifolia olia, Hyacinth profit or gain, Rosmarinus officinalis, esculent, and Salvia officinalis) were recovered using the tube dilution process and evaluated using Gas chromatographic and Gas chromatography-mass. The antihypertensive activity of the vital oil produced by such plants was then evaluated on Plasmodium. Plasmodium simplex was found in 2 strains: FcBl Colombia and an African sulfa drugs infection. The mosquito’s development was 50 percentage points inhibited (in vitro) at 2 doses ranging from 150 g/mL to 1 mg/mL, and the impact was observed after twenty-four and seventy-two hours (Milhau et al., 1997).

17.5.11 Anticataleptic activity The benefits of leaf extracts of J. communis (MEJC) leaf on reserpine-induced paresthesias in rats were investigated in this anticataleptic study. Filing (2.5 mg/kg, i.p.) was administered intraperitoneally (i.p.) to cause catalepsy. The effectiveness of the leaf extracts toward reserpine-induced paresthesias in rats was tested at 100 and 200 mg/kg (i.p.). When compared to tacrine rats, the MEJC extracted was shown to drastically reduce hallucinations and delusions (P ¼ 0.001); the largest decrease was seen at a dosage of 200 mg/kg (Bais et al., 2014a, b).

17.5.12 Neuroprotective activity The neuroprotective efficacy of J. vulgaris (MEJC) was tested in a mouse Brain cancer model generated by antipsychotics (CPZ). The two dosages (100 and 200 mg/kg, i.p.) were chosen based on the single-dose for mice (LD50). The herb was tested for paresthesias (bar test), muscular stiffness (rot rod test), and physiological responses (actophotometer) in rats’ brains, as well as its influence on biomarkers (TBARS, GSH, ammonia, and serum total). MEJC was found to have a substantial (P 0.001) cognitive impact against CPZ-induced Parkinson’s-like symptoms or antiactivity Parkinson’s in J. vulgaris (Rana and Bais, 2014).

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17.6 Conclusion The perennial fragrant shrub Juniperus Vulgaris L. has a significant medicinal promise in the cure of people’s ailments. Fragrant oils, carbohydrates, varnishes, catechin, oxalic compound, leucoanthocyanidin terpenic acids, alkaloids, polyphenols, tannins, gums, glucans, beeswax, and other compounds are abundant in the plant. They are used as antidiabetes, antibiotics, and for the cure of different and immunological illnesses for centuries. Juniper crude oil and extracts have been shown to have oxidative, antibiotic, and other activities in studies. In laboratory animals, strawberries have also been discovered to have generally pro, apoptotic, hypoglycemia, and antihyperlipidemic properties.

References Ahani, H., Jalilvand, H., Hosseini Nasr, S.M., Soltani Kouhbanani, H., Ghazi, M.R., Mohammadzadeh, H., 2013. Reproduction of juniper (Juniperus polycarpos) in Khorasan Razavi, Iran. For. Sci. Pract. 15, 231–237. Akdogan, M., Koyu, A., Ciris, M., Yildiz, K., 2012. Anti-hypercholesterolemic activity of J. communis oil in rats: a biochemical and histopathological investigation. Biomed. Res. 23 (3), 321–328. Akkol, E.K., Guvenc, A., Yesilada, E., 2009. A comparative study on the antinociceptive and anti-inflammatory activities of five Juniperus taxa. J. Ethnopharmacol. 125, 330–336. Al-Ramamneh, E.A., Dura, S., Daradkeh, N., 2012. Propagation physiology of Juniperusphoenica L. from Jordan using seeds and in vitro culture techniques: baseline information for a conservation perspective. Afr. J. Biotechnol. 11, 7684–7692. Al-Ramamneh, E.A., Daradkeh, N., Rababah, T., Pacurar, D., Al-Qudah, M., 2017. Effects of explant, media and growth regulators on in vitro regeneration and antioxidant activity of Juniperus phoenicea. Aust. J. Crop. Sci. 11, 828–837. Angioni, A., Barra, A., Russo, M.T., Coroneo, V., Dessi, S., Cabras, P., 2003. Chemical composition of the essential oils of Juniperus from ripe and unripe berries and leaves and their antimicrobial activity. J. Agric. Food Chem. 51 (10), 3073–3078. Bais, S., Gill, S., Rana, N., 2014a. Effect of J. communis extract on reserpine induced catalepsy. Inventi Rapid: Ethnopharmacol. 4, 1–4. Bais, S., Gill, N.S., Rana, N., Shandil, S., 2014b. A phytopharmacological review on a medicinal plant: Juniperus communis. Int. Scholarly Res. Not. 2014. Banerjee, S., Mukherjee, A., Chatterjee, T.K., 2012. Evaluation of analgesic activities of methanolic extract of medicinal plant Juniperus communis Linn. Int. J. Pharm. Pharm. Sci. 4 (5), 547–550. Cantos, M., Cuerva, J., Za´rate, R., Troncoso, A., 1998. Embryo rescue and development of Juniperus oxycedrussubsp. Oxycedrus and macrocarpa. Seed Sci. Technol. 26, 193–198. Cantrell, C.L., Zheljazkov, V.D., Carvalho, C.R., Astatkie, T., Jeliazkova, E.A., Rosa, L.H., 2014. Dual extraction of essential oil and podophyllotoxin from creeping juniper (Juniperus horizontalis). PLOS ONE 9 (9), e106057. Chang, Ing-Feng (ed.). Castro, M.R., Belo, A.F., Afonso, A., Zavattieri, M.A., 2011. Micropropagation of Juniperus navicularis, and endemic and rare species from Portugal SW coast. Plant Growth Regul. 65, 223–230. Daneshvar, A., Tigabu, M., Karimidoost, A., Od
en, P.C., 2016. Stimulation of germination in dormant seeds of Juniperus polycarpos by stratification and hormone treatments. New For. 47, 751–761. Gruwez, R., Leroux, O., De Frenne, P., Tack, W., Viane, R., Verheyen, K., 2013. Critical phases in the seed development of common juniper (Juniperuscommunis). Plant Biol. 15 (1), 210–219. Hazubska-Przybył, T., 2019. Propagation of Juniper species by plant tissue culture: a mini-review. Forests 10 (11), 1028. Kalinkevich, K., Karandashov, V.E., Ptitsyn, L.R., 2014. In vitro study of the anti-inflammatory activity of some medicinal and edible plants growing in Russia. Russ. J. Bioorg. Chem. 40, 752–761. Kocer, Z.A., Gozen, A.G., Onde, S., Kaya, Z., 2011. Indirect organogenesis from bud explants of Juniperus communis L.: effect of genotype, gender, sampling time and growth regulator combinations. Dendrobiology 66, 33–40.

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c, N.M., 2014. Phytochemical composition and antioxidant, anti–inflammatory and antimicrobial activities of Juniperus macrocarpa Sibth. et Sm. J. Funct. Foods 7, 257–268. Loureiro, J., Capelo, A., Brito, G., Rodriguez, E., Silva, S., Pinto, G., Santos, C., 2007. Micropropagation of Juniperus phoenica from adult plant explants and analysis of ploidy stability using flow cytometry. Biol. Plant. 51, 7–14. Mao, K., Hao, G., Liu, J., Adams, R.P., Milne, R.I., 2010. Diversification and biogeography of Juniperus (Cupressaceae): variable diversification rates and multiple intercontinental dispersals. New Phytol. 188 (1), 254–272. McCabe, M., Gohdes, D., Morgan, F., Eakin, J., Sanders, M., Schmitt, C., 2005. Herbal therapies and diabetes among Navajo Indians. Diabetes Care 28 (6), 1534–1535. Miceli, N., Trovato, A., Marino, A., Bellinghieri, V., Melchini, A., Dugo, P., Cacciola, F., Donato, P., Mondello, L., G€ uvenc¸, A., De Pasquale, R., 2011. Phenolic composition and biological activities of Juniperus drupacea Labill. Berries from Turkey. Food Chem. Toxicol. 49 (10), 2600–2608. Milhau, G., Valentin, A., Benoit, F., et al., 1997. In vitro antimalarial activity of eight essential oils. J. Essent. Oil Res. 9 (3), 329–333. Modnicki, D., Łabędzka, J., 2009. Estimation of the total phenolic compounds in juniper sprouts (Juniperus communis, Cupressaceae) from different places at the Kujawsko-Pomorskie province. Herba Polonica 55 (3). Momeni, M., Ganji-Moghadam, E., Kazemzadeh-Beneh, H., Asgharzadeh, A., 2018. Direct organogenesis from shoot tip explants of Juniperus polycarpos L.: optimizing basal media and plant growth regulators on proliferation and root formation. PCBMB 19, 40–50. Mrabet, A., Rejili, M., Lachiheb, B., Toivonen, P., Chaira, N., Ferchichi, A., 2008. Microbiological and chemical Characterisations of organic and conventional date pastes (Phoenix dactylifera L.) from Tunisia. Ann. Microbiol. 58, 453–459. Negussie, A., 1997. In vitro induction of multiple buds in tissue culture of Juniperus excelsa. For. Ecol. Manag. 98, 115–123. Orhan, N., 2019. Juniperus species: Features, profile and applications to diabetes. In: InBioactive Food as Dietary Interventions for Diabetes. Academic Press, pp. 447–459. Pepeljnjak, S., Kosalec, I., Kalodera, Z., Blazˇevi
c, N., 2005. Antimicrobial activity of juniper berry essential oil (Juniperus communis L., Cupressaceae). Acta Pharma. 55 (4), 417–422. Raina, R., Verma, P.K., Peshin, R., Kour, H., 2019. Potential of Juniperus communis L as a nutraceutical in human and veterinary medicine. Heliyon 5 (8), e02376. Rana, N., Bais, S., 2014. Neuroprotective Effect of J. communis in Parkinson Disease Induced Animal Models (M.S. thesis in Pharmacy). Pharmacology Department, Punjab Technical University, Punjab, India. Sarangzai, A.M., Ahmed, M., Ahmed, A., Leghar, S.K., Syed Umer, J.A., 2012. Juniper forests of Baluchistan: a brief review. FUUAST J. Biol. 2 (1), 71–79. Sati, S.C., Joshi, S., 2010. Antibacterial potential of leaf extracts of Juniperus communis L. from Kumaun Himalaya. Afr. J. Microbiol. Res. 4 (12), 1291–1294. Sokovi
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C H A P T E R

18 Patchouli essential oil Syeda Saniya Zahraa, Gulzar Ahmad Nayikb, and Tooba Khalidaa a

Department of Pharmacognosy, Shifa College of Pharmaceutical Sciences, Shifa Tameer-e-Millat University, Islamabad, Pakistan bDepartment of Food Science & Technology, Government Degree College Shopian, Srinagar, Jammu & Kashmir, India

18.1 Introduction Plants are a major source of raw materials for the cosmetic, perfumery, pharmaceutical, and soap industries (Harvey, 2008; Meena et al., 2009) by applying modern techniques for processing and manufacturing (Sucher and Carles, 2008). Likewise, the Pogostemon cablin Benth., commonly known as patchouli (Family, Lamiaceae), is famous for its role in cosmetic and pharmaceutical industry. A Philippine botanist Pellitier-Sautellet in 1845 first time discovered Patchouli named it Pogostemon patchouli (Ramya et al., 2013). Although patchouli is a fragrant, naturally grown herb of Philippines, it grows wildly in the Asian countries as well. It is cultivated for commercial purpose in Malaysia, India, China, Indonesia, Singapore, Vietnam, and West Africa (Swamy et al., 2010). The species name of patchouli is “cablin” which has been derived from the word “cabalam” (local name of patchouli in Philippines) (Bhaskar and Vasantha Kumar, 2000). There are different vernacular names of patchouli plant in various regions of the world. It is known as phimsen (Thailand), tamala patra (Sanskrit), guang hou xiang (Indonesia and China), nilam (Malaysia), patche tene (Kannada), patchouli (Hindi), patchapan or patcha (Marathi), patchilla (Malayalam), and pacchilai (Tamil). Patchouli is a sturdy perennial herb which bears small and light pink to white flowers (Chakrapani et al., 2013). It is grown well in hot and humid climatic conditions. It can grow to as much as 1.2 m high. The leaves are broad with lobed margins (Angadi and Vasanthakumar, 1995). The essential oil is present in glandular trichomes (Guo et al., 2013). Patchouli oil is important ingredient of perfumes and soap because of its aromatic and fixative properties and is composed of sesquiterpenes (Farooqi and Sreeramu, 2001). Patchouli oil is used in very low concentration (2
106 kg kg1) for flavoring food, soft drinks, candy, and baked products (Bauer et al., 1997).

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18. Patchouli essential oil

The traditional Chinese medicine (TCM) includes patchouli in the Baoji and Houdan pills for the treatment of inflammatory diseases (Xian et al., 2007; Zhang et al., 1998). In the Ayurveda, patchouli is used in the treatments including Guna, Rasa, and Virya. It is also used to cure colds, nausea, diarrhea, vomiting, headaches, and insect bites in Japan, China, and Malaysia (Chinese Pharmacopoeia Commission, 2010). The patchouli oil acquired via steam distillation of its leaves, has a great commercial significance. It imparts a strong aromatic, sweet, spicy fragrance (Vijayakumar, 2004). It is blended with other oils to impart a powerful base, and long lasting character. Therefore, the oil is utilized in the manufacturing of scents, soaps, and detergents (Kumaraswamy and Anuradha, 2010). Patchouli oil finds it’s utility in aromatherapy as well where it is used to relieve stress, anxiety and depression, manage hunger and increase libido (Chakrapani et al., 2013; Kalra et al., 2006; Kumara and Anuradha, 2011). It possesses significant biological effects including antimutagenic, antimicrobial, analgesic, antioxidant, antiplatelet, antiinflammatory, aphrodisiac, antiemetic, antidepressant, and fibrinolytic (Chakrapani et al., 2013; Liu et al., 2009; Priya et al., 2014).

18.2 Production and composition Patchouli usually grows wild in different parts of the world especially in Malaysia, Singapore, and Indonesia. Asia is known in the world as the land of aromatic plants, spices, and traditional perfumes because of its suitable weather conditions which is good for the growth and development of such plants. During 1941 Patchouli was introduced in India in Madhya Pradesh, Kerala, Tamil Nadu, and Karnataka. In India, it is grown in, West Bengal, Karnataka, Assam, Madhya Pradesh, coastal regions of South India and Gujarat (Ramya et al., 2013). Tata Oil Mills in 1942 first time cultivated this crop commercially. Its revealed from experiments that weather conditions of Bangalore is suitable for production of good quality patchouli oil (Sarwar et al., 1983). Patchouli is a usually a tropical crop but it can be grown in subtropical areas. It prefers to grow in hot and humid environment and perfectly grows at an altitude of 800–1000 m above sea level. In coastal areas to grow well it requires 80%–90% of relative humidity, temperature of 20–35°C and well-drained soil with a pH value of 6.0–6.8. Main purpose of patchouli plant cultivation is to get essential oils which are mostly present in their leaves and very less quantity of essential oil is also found in parts of the stem which are tender. By using steam distillation technique on the dry leaves of patchouli we can get essential oils of patchouli (Ramya et al., 2013). Patchouli depending upon the site of collection has variable composition of essential oil in it. An analysis of almost 100 samples from different research articles (around 75) was done and a table representing the constituents as average percentages and ranges is formulated (Table 18.1). The ranges in Table 18.1 shows large variations in the patchouli oil constituents. The variation in ranges can be due to the presence of oxygenated compounds in greater amounts and relatively lower amounts of hydrocarbons. Apart from the difference in the relative concentrations of different constituents of patchouli oil, the chemical variation could also occur due to the change in the drying and distillation processes. The amount of pogostone is affected due to this phenomenon. It could also happen that there could exist different chemotypes of P. cablin producing variable concentrations of pogostone and patchoulol (Luo et al.,

431

18.2 Production and composition

TABLE 18.1

Average concentration and ranges of major constituents present in patchouli oil.

S. no.

Constituent

Average %

Ranges %

1

α-Pinene

0.09

0.01–0.3

2

β-Pinene

0.20

0.02–1

3

Limonene

0.03

0.01–0.3

4

δ-Elemene

0.52

0.01–1.9

5

β-Patchoulene

3.0

0.03–12

6

β-Elemene

0.89

0.18–1.9

7

Cycloseychellene

0.46

0.02–0.8

8

(E)-β-Caryophyllene

3.1

0.75–6.8

9

α-Guaiene

11

2.9–23

10

Seychellene

6.6

2.3–13

11

α-Humulene

0.69

0.05–2

12

α-Patchoulene

4.5

1.2–13

13

Germacrene D

0.12

0.0–0.2

14

Aciphyllene

2.4

0.7–4.2

15

α-Bulnesene

14

2.9–23

16

Norpatchoulenol

0.86

0.11–4.0

17

Caryophyllene oxide

0.73

0.0–4.6

18

Pogostol

2.4

0.2–6.2

19

Patchoulol

39

11–72

20

Pogostone

8.9

0.1–27.7

Adopted from van Beek, T.A., Joulain, D., 2018. The essential oil of patchouli, P. cablin: a review. Flavor Fragr. J. 33 (1), 6–51.

2003). Moreover, the presence of a constituent in one part of the plant can be greater than the other part for example, patchouli oil of stem has 20 time more the amount as present in the leaf part (Luo et al., 2002). The γ and δ-patchoulene are not included in the table due to the absence of the sufficiently reliable data in literature. The patchouli essential oil is composed of more than 24 different sesquiterpenes rather than a mixture of various mono-, di-, and sesquiterpene compounds (Bure and Sellier, 2004). Major component is the sesquiterpene patchouli alcohol which is the basic constituent responsible for the specific patchouli note (N€ af et al., 1981).

18.2.1 Adulteration and contamination The introduction of modern analytical techniques (i.e., GC-MS, and NMR) physical methods (such as solubility, refractive index, and density) and chemical evaluation technique (i.e., color tests, and saponification number) made it easier to identify the adulteration

432

18. Patchouli essential oil

(Parry, 1921). The contamination of the PEO with the cheap gurjun balsams was detected through GC and this technique was found to be highly useful in the detection of adulteration. The PEO is usually adulterated with copaiba and gurjun balsams and the presence of either α-gurjunene or alloaromadendrene confirms the presence of gurjun balsam (van Beek and Joulain, 2018). The quality testing has further reached another level due to the GC fingerprinting based on GC-TIC or GC-FID (GC-Total Ion Chromatogram or GC-Flame Ionization Detector). The detection ability is even strengthened due to the 13C NMR (Kubeczka and Forma´cek, 2002) and HPTLC (high performance TLC) methods (Kaloustian, 2012). The authentic oil of patchouli is also adulterated with the cheap (i.e., 25% cheaper), commercially available substitute that is Clearwood. The contamination with Clearwood is detected due to the presence of patchoulol ethyl ether as confirmed on GC-MS analysis (van Beek and Joulain, 2018).

18.2.2 Odor of patchouli essential oil The PEO can be described as a dark orange to brown, viscid liquid with a rich, sweet, aromatic, and woody odor. The freshly distilled PEO can lack the floral sweetness initially but on aging it would develop the pleasant, characteristic odor (Arctander, 1960). It involves a very strong, sweet balsamic, and woody/earthy notes (Haarmann and Reimer, 1985). The scores expressing the GC-olfactometric analysis consisted of the following scale: 0 (odorless), 1 (weak), 2 (well detectable), and 3 (intense). The afore-mentioned scale was used to assign the scores to approximately 15 GC-eluted constituents out of which only patchoulol was marked the scale of “3” (Nikiforov et al., 1986). The researchers established the patchoulol as the main odor imparting component of PEO. The main odor imparting components, the three structurally related alcohols comprise of (+)-norpatchoulenol, ()-patchoulol, and (+)-nortetracyclopatchoulol (Ohloff et al., 2012) with the concentrations of 0.5%, 30%, and 0.001%, respectively. Several studies have reported that aged PEO smells better than the fresh oil (Milchard et al., 2004; Ramya et al., 2013). An old sample of PEO exhibits a fuller and finer odor than the freshly distilled one. The best grades of patchouli oil would be characterized by rich fruity note which are produced over prolonged periods (Guenther, 1949). The freshly distilled PEO possesses a harsh note due to the presence of ammonia, hydrogen sulfide and acetaldehyde (Gildemeister and Hoffmann, 1899) these compounds, however, evaporate within a few days of distillation.

18.3 Extraction techniques Patchouli plant is one of the most important essential oil-producing plants which help in more than 50% of total essential oils exports of Indonesia. In Indonesia patchouli oil is generally carried out using old methods (steam distillation, hydrodistillation), although such methods require more energy, time and solvents in large amounts. But now a days, patchouli oil extraction was done using a different techniques like microwave hydrodistillation and microwave air-hydrodistillation method.

18.3 Extraction techniques

433

18.3.1 Steam distillation Steam distillation is an old technique used for extraction of essential oil from patchouli. Steam distillation method usually uses a greater amount of heat in the extraction process which leads to thermal degradation of most of compounds residing inside the patchouli leaf. Steam distillation method is not suitable for delicate plants (Shukor, 2008).

18.3.2 Hydrodistillation Hydrodistillation is an old technique used for extraction of essential oil from patchouli. In this technique we usually use a hot plate (Magnetic Stirrer SH-3). Time consumption for extraction of essential oil is almost 13 h. The CO2 emissions and electricity required to obtain 1 g patchouli essential oil using hydrodistillation method is almost 6.5526 kg and 6.5526 kW, respectively (Kusuma and Mahfud, 2017).

18.3.3 Microwave hydrodistillation Time consumption for extraction of essential oil from patchouli by using the microwave hydrodistillation is almost 2 h. The CO2 emissions and electricity required to obtain 1 g patchouli oil using microwave hydrodistillation method is 1.6206 kg and 1.6206 kW h, respectively (Kusuma and Mahfud, 2017). The recovery value for patchouli oil extraction using microwave hydrodistillation was 70.1456% using a microwave power of 600 W and a ratio of patchouli leaves to distilled water of 0.10 g mL1. Almost 21 compounds with three heavy fractions were identified from patchouli by using microwave hydrodistillation.

18.3.4 Microwave air-hydrodistillation Microwave air-hydrodistillation method is a new technique with faster extraction rate and large amount of product yield. Time consumption for extraction of oil from patchouli by using the microwave air-hydrodistillation is almost 2 h. The CO2 emissions and electricity required to obtain 1 g patchouli oil using microwave air-hydrodistillation method is 1.4210 kg and 1.4210 kW h, respectively (Kusuma and Mahfud, 2017). The recovery value for the microwave air-hydrodistillation method was 99.8863% using a microwave power of 600 W, a ratio of patchouli leaves to distilled water of 0.10 g mL1 and an air flow rate of 5.0 L min1 (Kusuma and Mahfud, 2017). Almost 26 compounds were identified with seven heavy fractions from patchouli by using microwave air-hydrodistillation. In microwave air-hydrodistillation method flow of air help in extracting of heavy fraction components which are usually present inside the cell membrane or tissue of plant and do not diffuse out easily. Patchouli oil’s heavy fractions are important oil components as mostly they are oxygenated terpenes which play more important role in the aroma of essential oil as compare to any other components (Kusuma and Mahfud, 2017).

434

18. Patchouli essential oil

18.3.5 Solvent-free microwave extraction Solvent-free microwave extraction method is a new green technique for Patchouli oil extraction. The CO2 emissions and electricity required to obtain 1 g of patchouli oil by using solvent-free microwave extraction method is 0.4 kg and 0.5 kWh, respectively (Putri et al., 2017). Time consumption for extraction of essential oil from patchouli by using solvent-free microwave extraction is almost 2 h. We can use solvent-free microwave extraction method as a new green technique for patchouli oil extraction.

18.3.6 Ultrasonic assisted solvent extraction Ultrasonication is the new technique used in extraction of essential oil. The wave used in ultrasonication will penetrate the cell walls and increase the transfer of essential components from the cell into the solvent. Therefore, the extraction of essential oil becomes easier (Shukor, 2008).

18.4 Characterization Patchouli essential oil has been characterized by GC-MS analyses and has major components like α-guaiene, δ-guaiene, patchouli alcohol, α-patchoulene, seychellene, 3-patchoulene, and transcaryophylene (Karimi, 2014). 130 chemical components of patchouli essential oil have been found. Sesquiterpene patchoulol is the most important component. The characterization of patchouli oil can be done by 2D-GC and chiral GC. The methods are discussed as follows.

18.4.1 Two-dimensional gas chromatography (2D-GC) The identification of various components of patchouli oil such as α-guaiene, seychellene, α-bulnesene, α- and β-patchoulene, and patchoulol, resulted till the 1970s. The newly introduced techniques included gas chromatography and 1H NMR. Capillary GC was used for better separation from PEO hydrocarbons in 1967 (Tsubaki et al., 1967). The GC-IR became very famous in the 1980s; however, with the passage of time, it was largely replaced by GC-MS. Over the next one and a half decades, GC/MS became available and 13C NMR was also introduced which even enhanced the analytical capabilities further. Till now, GC/MS is the gold standard in determination of volatile oil constituents. Although the GC technique gave a fair level of resolution but the throughput of new compounds did not rise according to expectations (Zhu et al., 2017). Another technique was utilized for the differentiation among enantiomers by using vibrational circular dichroism (VCD). The 2D NMR has been largely exploited instead of total synthesis. The chromatographic technique remarkably increased the resolution of essential oils by the provision of 2D-GC with time-of-flight mass spectrometry (2D-GC-TOF-MS) (Zaizen et al., 2014).

18.4 Characterization

435

2D-GC is far more powerful than 1D for the separation of complex essential oils. It provides a clean mass spectra and resolve the minor components as well which was missing from 1D-GC. This was illustrated by using 20 m BPX5 column in the 1st dim. and a 2 m DB1701 column in the 2nd dim (Edwards et al., 2016). Detection was carried out by EI-TOF-MS (electron impact-time of flight-mass spectrometry) at both 70 and 12 eV. It showed an added advantage over a 1D-GC with a 60 m column. However, it was suggested that using a DB5 and Wax columns would have given improved resolution than the above-mentioned columns.

18.4.2 Chiral GC The chiral GC is employed both for identification of enantiomers and separation of components with its unique selectivity as a stationary phase (Sonwa, 2000). The chiral GC (e.g., Chiralsil-Val phase) has been employed for separation purposes to provide a better and faster resolution. But, nowadays, due to innovation in standard stationary phase, DB5, the resolution is improved (Betts, 1994). It is speculated on the basis of already reported data on optical rotations of PEO compounds and their biosynthetic pathways, the enantiomers may be nonexistent. But it needs to be widely tested. A study was performed using a 60 m Wax column in the 1st dim. and a 3 m chiral (Cyclodex-B) column in the 2nd dim. With the modulation time of 5 s and a temperature gradient of 70–200°C at the rate of 3°C min1, a better resolved spectra was obtained with a lot of monoterpenes and a few sesquiterpenes not reported previously. The authors claimed to identify 394 compounds but the relative concentrations are not given (Wu et al., 2004).

18.4.3 Chromatographic fingerprint of patchouli oil Chromatographic fingerprinting provides a great benefit for the commercial as well as research purposes as it helps in regulating the quality of oil. It also informs about the adulterants or impurities. The PEO fingerprint is characterized by combination of the compounds in the fixed relative ratios (as shown in Fig. 18.1A–C). The chromatograms in Fig. 18.1A–C, the sesquiterpene regions of three different PEOs are shown. On comparing these oil components with the ISO norms (as given in Table 18.2), interesting results are obtained. The oil A virtually meets the ISO norms but it lacks pogostone. The oil B does however, contain pogostone, a very high norpatchoulenol content and minor content of α and β-pinene. The oil C contains some pogostone. All the oils had higher levels of patchouli along with several oxygenated sesquiterpenes and a low hydrocarbon content (van Beek and Joulain, 2018). As evident by comparison, the ISO norms are limiting. For instance, a lot of blending is done on manufacturers’ part in order to meet the standard based on patchoulol content. This is usually accomplished by mixing Indonesian PEO containing high patchoulol content with cheaper low quality Chinese PEO (Milchard et al., 2004). According to the ISO Norms, the copaene is present in trace amounts but it usually present in PEO instead cycloseychellene would be a better choice. The compounds like seychellene, nortetracyclopatchoulol, and pogostone are quite likely to exist in PEO but are not mentioned in the ISO Norm. The compound, α-gurjunene is an adulterant and therefore should not be allowed even at 0.2% in oils.

FIG. 18.1 (A) Partial gas chromatogram (sesquiterpene region) of patchouli oil A on a DB5 stationary phase. Abbreviations: δE, δ-Elemene; βE, β-Elemene; βPa, β-Patchoulene; βCa, (E)-β-Caryophyllene; CyS, Cycloseychellene; αGu, α-Guiaene; Sey, Seychellene; αHu, α-Humulene; αPa, α-Patchoulene; δPa, δ-Patchoulene; U, Unidentified constituents; GD, Germacrene D; δSe, δ-Selinene, Selina-4;6-diene; 15, Pentadecane; Aci, Aciphyllene; αBu, α-Bulnesene, δ-Guiaene; 7eS, 7-epi-α-Selinene; ZNe, (Z)-Nerolidol; (Continued)

437

18.5 Chemistry and properties

FIG. 18.1, CONT’D eBu, 1;10-epoxy-α-Bulnesene; nPa, Norpatchoulenol; Cao, Caryophyllene oxide; ntP, Nortetracyclopatchoulol; Pgl, Pogostol; Pat, Patchoulol. GC conditions: 60 m
0.25 mm
0.25 μm DB5 column; He 18 psi; 60°C (0 min hold) to 260°C at 3°C min1; MS detection. (B) Partial gas chromatogram (sesquiterpene region plus pogostone) of PEO B prepared from stems on a DB5 stationary phase. For peak assignments and conditions (see panel A). 2mP, 4-Hydroxy-6-methyl-3-(2-methyl-1-oxobutyl)-2H-pyran-2-one; 6mP, 4-Hydroxy-6-methyl-3-(3methyl-1-oxobutyl)-2H-pyran-2-one; Pgn, Pogostone. (C) Partial gas chromatogram (sesquiterpene region) of a significantly oxidized PEO C on a DB5 stationary phase. For peak assignments and conditions (see panel A). Rtd, rotundone; 234, unidentified constituent with MW ¼ 234, possibly identical with (Arpana et al., 2008, 2014; Costa et al., 2013; Schrader et al., 2012). Adopted from van Beek, T.A., Joulain, D., 2018. The essential oil of patchouli, Pogostemon cablin: a review. Flavor Fragr. J. 33 (1), 6–51.

TABLE 18.2

Allowed ranges of several constituents of patchouli oil according to 2003 ISO norms.

S. no.

Constituent

Minimum %

Maximum %

1

β-Patchoulene

1.8

3.5

2

Copaene

Traces

1

3

α-Gurjunene

0.0

0.2a

4

α-Guaiene

11

16

5

β-Caryophyllene

2

5

6

Bulnesene

13

21

7

Norpatchoulenol

0.35

1

8

Patchoulol

27

35

9

Pogostol

1

2.5

10

Total

56.15

85.2

a

Only for oils prepared in an artisanal way. Adopted from van Beek, T.A., Joulain, D., 2018. The essential oil of patchouli, P. cablin: a review. Flavor Fragr. J. 33 (1), 6–51.

18.5 Chemistry and properties The patchouli essential oil obtained from P. cablin is known to possess a dozen of biological activities. The chemical composition of PEO along with its volatile components is presented in Table 18.3. The chemical composition and oil yield is largely affected by the variation in the site and period of collection and processing methods (Li et al., 2004). Sesquiterpenes such as patchoulol is present in PEO and is widely used in cosmetic, perfumery and soap industries (Bauer et al., 1997). The aroma of PEO is characterized by the presence of guaiene, patchoulenes, and seychellene. The quality of patchouli oil is due to mainly two major constituents, patchoulol, and α-patchoulene (Ramya et al., 2013). The minor sesquiterpenes in PEO include, pogostol, bulnesene, seychellene, cycloseychellene, caryophyllene, norpatchoulenol, patchoulene, and guaiene (Akhila et al., 1988). Pogostone, α- and β-patchoulene, and patchoulol impart aromatic odor as well as the beneficial pharmacological effects (Yi et al., 2013).

TABLE 18.3 The chemical composition of patchouli essential oil. Common chemical name

S. no.

1

α-Pinene

37

Pogostol

2

β-Pinene

38

Guaia-10(15),11-dien-1α-ol

3

Limonene

39

β-Patchoulenone

4

Pentadecane

40

Rotundone

5

α-Humulene

41

14-Nor-β-patchoul-1(5)-ene-4-one

6

Germacrene D

42

14-Nor-β-patchoul-1(5),2-diene-4-one

7

β-Elemene

43

2β-Methoxy-14-nor-β-patchoul-1(5)-ene-4-one

S. no.

Chemical structure

Chemical structure

Common chemical name

8

δ-Elemene

44

14-Nor-β-patchoul-1(5)-ene-2,4-dione

9

selina-4,11-diene

45

Pocahemiketal A

10

α-Selinene

46

Pocahemiketal B

11

δ-Selinene ¼ selina-4,6diene

47

4-Hydroxy-6-methyl-3-(1-oxobutyl)-2Hpyran-2-one

12

β-Selinene

48

4-Hydroxy-6-methyl-3-(2-methyl-1-oxopropyl)2H-pyran-2-one

13

7-epi-α-Selinene

49

4-Hydroxy-6-methyl-3-(3-methyl-1-oxobutyl)2H-pyran-2-one

14

Selina-4(15),7(11)-diene

50

4-Hydroxy-6-methyl-3-(2-methyl-1-oxobutyl)2H-pyran-2-one

15

α-Bulnesene (¼ δ-guaiene)

51

Pogostone; dhelwangin

Continued

TABLE 18.3 The chemical composition of patchouli essential oil—cont’d Common chemical name

S. no.

16

α-Guaiene

52

4-Hydroxy-6-methyl-3-(1-oxohexyl)-2Hpyran-2-one

17

Aciphyllene

53

4-Hydroxy-6-methyl-3-(5-methyl-1-oxohexyl)2H-pyran-2-one

18

(E)-β-Caryophyllene

54

Nonyl acetate

19

(E)-7-epi-βCaryophyllene

55

2-Methylbutyric acid

20

(Z)-β-Caryophyllene

56

Pentanoic acid

21

β-Patchoulene

57

4-Methylpentanoic acid

22

δ-Patchoulene

58

2-Methylpentanoic acid

S. no.

Chemical structure

Chemical structure

Common chemical name

23

γ-Patchoulene

59

Heptanoic acid

24

α-Patchoulene

60

Nonanoic acid

25

α-Copaene

61

cis-2-Pentylcyclopropanecarboxylic acid

26

Seychellene

62

trans-2-Pentylcyclopropanecarboxylic acid

27

Cycloseychellene

63

Phenol

28

1β,5β-Epoxy-guai-11ene

64

o-Cresol

29

1α,5α-Epoxyguai-11-ene

65

Dimethylphenol

30

Caryophyllene oxide

66

4-Vinylphenol

Continued

TABLE 18.3 The chemical composition of patchouli essential oil—cont’d Common chemical name

S. no.

31

1,10-Epoxy-guai-11-ene

67

Guaiacol

32

(Z)-Nerolidol

68

Eugenol

33

Patchoulol

69

Patchoulipyridine

34

Norpatchoulenol

70

Guaipyridine

35

Nortetracyclopatchoulol

71

(E)-3-(but-1-enyl)pyridine

36

6-Hydroxypatchoulol

72

(Z)-3-(but-1-enyl)-4-propylpyridine

S. no.

Chemical structure

Chemical structure

Common chemical name

Adopted from van Beek, T.A., Joulain, D., 2018. The essential oil of patchouli, P. cablin: a review. Flavor Fragr. J. 33 (1), 6–51.

18.5 Chemistry and properties

443

Patchouli oil from Vietnam was analyzed through GC, GC/MS, and NMR and the major components were detected as α- and δ-guaiene, β-caryophyllene, δ-cardinene, β-elemene, α-, β- and δ-patchoulene, seychellene, pogostol, α-bulnesene, and patchouli alcohol. The patchouli alcohol content was found to be 32%–37% which imparts a distinct odor to the essential oil (Dung et al., 1989). However, the patchouli obtained from Philippines produced germacrene-B as a major component of its oil and therefore exhibited an intensive odor (Hasegawa et al., 1992). The Patchouli essential oil obtained from China (Gaoyao County, Guangdong Province) and analyzed by GC/MS included pogostone, patchouli alcohol, α-guaiene, trans-caryophyllene, and seychellene (Luo et al., 1999). Contrary to this, GC/ MS analysis of Patchouli herb harvested from Leizhou County of China revealed a slightly different phytochemistry such as α- and δ-guaiene, patchouli alcohol, trans-caryophyllene, α-patchoulene, aciphyllene, and seychellene (Feng et al., 1999). The compounds detected in the Indonesian patchouli oil were α-pinene, δ-guaiene, δ-patchoulene, aciphyllene, β-pinene, α-patchoulene, 7-epi-α-selinene, limonene, α-copaene, δ-elemene, 1,10-epoxy-11-bulnesene, norpatchoulenol, β-elemene, cycloseychellene, β-caryophyllene, caryophyllene oxide, patchouli alcohol, nortetrapatchoulol, seychellene, patchoulenone, α-guaiene, 9-oxopatchoulol, pogostol, α-humulene, α-patchoulene, γ-gurjunene, germacrene D, and isopatchoulenone (Bure and Sellier, 2004). Zhao et al. (2005) successfully determined the patchoulol content by GC/MS method. The patchouli oil yield is also affected by variation in the time of collection. The variation in the volatile oil composition obtained from Hainan, China harvested in the months of June, July, and August were 0.8%, 0.7%, and 0.6%, respectively, with the highest patchouli alcohol content in the month of June (Luo et al., 2002). Fractional or steam distillation has been used for obtaining patchouli oil but this may result in the degradation of a few phytoconstituents of the oil. Hence, a supercritical extraction method was developed to obtain the maximum yield of patchouli oil with better quality (Donelian et al., 2009). Molecular distillation was also documented for good quality yield of patchouli oil (Hu et al., 2004; Chen et al., 2009). There is a cheaper alternative than the above methods, the microwave assisted extraction gives an improved oil yield with good quality oil (Kamal, 2010). Patchouli essential oil has sweet-herbaceous woody odor which is unique in nature. Patchouli essential oil is dark orange/brown in color. It is usually viscous liquid. It also has higher refractive index, absolute specific gravity, and optical rotation values (van Beek and Joulain, 2018). The good quality patchouli oil exhibits higher values of specific gravity, optical rotation, refractive index, and good solubility (Guenther, 1949). This is because of patchoulol content which is higher and provides a fairly pleasant aroma. This was particularly observed in “Singapore oils” which was in high demand due to higher specific gravity and solubility properties than “Java patchouli oil” (van Beek and Joulain, 2018). In the Chinese Pharmacopeia, the specifications for patchouli essential oil and its leaves is present as monographs (Chinese Pharmacopoeia Commission, 2015). Identification of patchouli leaves is done by microscopy. The contained essential oils are detected through TLC by using patchoulol as reference standard (0.1% in dry leaves) (Chinese Pharmacopoeia Commission, 2015). However, the patchouli essential oil is confirmed by its color, odor, specific gravity, specific rotation, and refractive index (as shown in Table 18.4). The TLC is also performed for confirmation by using patchoulol and pogostone as reference substances.

444

18. Patchouli essential oil

TABLE 18.4 Physicochemical properties of patchouli essential oil. S. no.

Source

Values 1

1

Specific gravity (g mL )

0.950–0.975

2

Refractive index

1.507–1.515

3

Optical rotation

48° to 65°

4

Miscibility with 90% ethanol

Mixture of 10:1 90% ethanol:oil gives a diaphanous solution or light opalescence

5

Color

Light yellow to reddish brown

Adopted from van Beek, T.A., Joulain, D., 2018. The essential oil of patchouli, P. cablin: a review. Flavor Fragr. J. 33 (1), 6–51.

18.6 Applications Patchouli essential oil has wide applications in cosmetic, pharmaceutical, food, beverage, cigarette, perfumery, and insecticidal industry. Its unique and extensive applications play an importance role in the world market (Swamy and Sinniah, 2015). Patchoulol is the major ingredient of patchouli essential oil and plays a great role in cosmetic, tobacco, shampoos, perfumes, toilet soaps, cleaning solutions, and washing powders. Patchouli is used in wide range of popular perfumes such as Arpege, Picasso, Dior, Tabu, Miss Opium, Paloma, Angel, and Ysatis because of its sensual and woody odor (Singh et al., 2002). Patchouli is used in vast range of air fresheners, detergents used for washing of laundry and towels made up of paper. Patchouli essential oil is used as antiseptic and used to prevent infection in cuts, wounds, and sores. It has astringent property as it stimulates muscle contraction of skin and nerve tissues. It also prevents sagging of skin, skin lesion, skin abrasion, pressure sores, loss of hair, and muscles and also strengthens gums on teeth. Patchouli essential oil has anti mark or anti scar ability. It decreases wound healing time and remove marks caused by boil, acne, pox, and measles (Kerr, 2002).

18.6.1 Aromatherapy Patchouli essential oil is used in aromatherapy because of its antidepressant property. In normal adult its fragrance decreases sympathetic activity (Haze et al., 2002). It also helps in treating symptoms related to menopause like sweating and hot flashes. It improves cerebral activities like soothing and tranquilizing (Perry and Perry, 2006). Patchouli essential oil also helps in reducing physiological responses like stress index, pulse rate and blood pressure by inhaling their odor. Aromatherapy which includes inhalation of patchouli essential oil odor, baths and massages by patchouli essential oil help in managing stress and decreases perceptions of long-term pain (Buckle, 2002).

18.6.2 Pharmacological activities In the past years, patchouli has been extensively studied for multiple pharmacological activities, including antipeptic ulcer, antioxidative, antimicrobial, antiinflammatory, analgesic,

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FIG. 18.2

The pharmacological effects of patchouli ( Junren et al., 2021). Adopted from Junren, C., Xiaofang, X., Mengting, L., Qiuyun, X., Gangmin, L., Huiqiong, Z., Guanru, C., Xin, X., Yanpeng, Y., Fu, P., Cheng, P., 2021. Pharmacological activities and mechanisms of action of Pogostemon cablin Benth: a review. Chin. Med. 16 (1), 1–20.

I/R injury protection, antitumor, antihypertensive, antidiarrheal, antidiabetic, intestinal microecology protection, immune-regulatory, and others ( Junren et al., 2021). The protective effects of patchouli have been demonstrated on various organs including liver, intestines, stomach, and brain (as shown in Fig. 18.2). 18.6.2.1 Gastrointestinal protective effect Pogostone was shown to protect the gastrointestinal mucosa in the indomethacin-induced gastric ulcer rat model by the activation of catalase (CAT), superoxide dismutase (SOD), and reduction of melandialdehyde (MDA). It was also demonstrated that pogostone increased the levels of Bcl-2 protein and heat shock protein 70 and reduced the expression of Bax protein at the site of gastric ulcer (Chen et al., 2016). Pogostone through its gastroprotective function suppressed the cellular apoptosis. Likewise, patchoulene epoxide (PAO), also showed the protective effect in rat model of the ethanol-induced gastric ulcer by increasing the GSH, SOD, and CAT levels and decreasing the MDA levels. It was also found to block the caspase-3 expression, FasL, and Fas in the gastric region (Liang et al., 2018). The β-patchoulene reduces the size of gastric ulcers by the inhibition of MDA, IL-6, IL-1β, and TNF-α synthesis and Fas, FasL, and caspase-3 expression. It was also shown to increase the SOD, and CAT activities (Liu et al., 2017).

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18.6.2.2 Effect on intestinal microecology The gut microbiota (GM) has a great role in protection against cancer (Vetizou et al., 2015), enteropathogens (Fukuda et al., 2011), and brain function and behavior (Cryan and Dinan, 2012). The abnormalities in the gut microbiota (dysbiosis), may be a risk factor of IBD (inflammatory bowel disease) (Marchesi et al., 2016), and obesity (Boulange et al., 2016). The pogostone, patchouli alcohol have been shown to maintain the gut epithelial barrier, aid in the polarization of M1 to M2 macrophage phenotypes which in turn promote the diversity the gut microbiota and inhibit the pro-inflammatory cytokines in mouse models (Leong et al., 2019). 18.6.2.3 Antidiarrheal effect Diarrhea predominant irritable bowel syndrome (IBS-D) is an agonizing gastrointestinal disorder (Lovell and Ford, 2012). The patchouli alcohol has been found to decrease the colonic smooth muscle contractions with an EC50 of 41.9 μM (Zhou et al., 2018). It acts through nitrergic, cholinergic, and K+ channel pathways. 18.6.2.4 Antiemetic effect Patchouli leaves’ hexane extracts exhibited the antiemetic activity in young chicken because of its pogostol, pachypodol, and patchoulol components (Yang et al., 1999). 18.6.2.5 Antidiabetic effect The patchouli alcohol (PA) suppressed the adipogenesis in the high fat diet-induced obesity in mice by upregulating the expression of β-catenin (Lee et al., 2019). Also, PA mediated its role in inhibiting hepatic steatosis by blocking ER (endoplasmic reticulum) stress signals. PA also regulates the expression of VLDL (very low-density lipoprotein) receptors, apolipoprotein B100, and microsomal triglyceride-transfer protein. 18.6.2.6 Antihypertensive effect As a Ca2+ antagonist, patchouli alcohol causes the vasorelaxation which in turn reduces the blood pressure. The mechanism includes the inhibition of extracellular calcium ions while releasing the intracellular calcium ions RYR- and IP3R-mediated Ca2+ channels in the sarcolemma (Hu et al., 2018). 18.6.2.7 Effect on ischemia/reperfusion (I/R) injury The effectiveness of patchouli alcohol was tested in mice with I/R injury, it was found to decrease the infarct volume and blocked the progressing BBB (blood brain barrier) dysfunction. Moreover, the TNF-α and IL-1β proteins and mRNA levels were also decreased along with reduced JNK and p38 phosphorylation processes (Wei et al., 2017). Similarly, β-PAE pretreatment suppressed the apoptosis in I/R injury in rats, mainly by lessening the Bax/ Bcl-2 ratio and inhibiting the activation of caspase-3. In addition to this, glutathione peroxidase (GSH-PX) and superoxide dismutase (SOD) were elevated simultaneously reducing the MDA levels (Zhang et al., 2019).

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18.6.2.8 Antioxidant effect Patchouli oil has free radical scavenging activity and it inhibits the oxidation of hexanal to hexanoic acid which result in brain cell injury by forming reactive oxygen specie (Wei and Shibamoto, 2007; Kim et al., 2010). Patchouli oil maintains structural integrity of skin and prevents photoaging because of its antioxidative property (Lin et al., 2014). Pogostone also plays its role in inhibition of lipid oxidation by neutralizing hydroxyl and superoxide free radicals (Zhang and Tao, 2016). Moreover, it increases the concentration of GSH (glutathione), GSH/GSSG ratio (glutathione/glutathione disulfide) as well as activates the GR (glutathione reductase) and SOD (superoxide dismutase). As a consequence, the accumulation of ROS (reactive oxygen species) is suppressed. It also speeds up the fats metabolism thus preventing fatty degeneration (Huang et al., 2018). The patchouli alcohol was found to mitigate the cellular damage and inhibit the oxidative stress responses in IEC-6 cells via Nrf2-Keap1 pathway (Liu et al., 2016a, b). 18.6.2.9 Antiinflammatory effect A significant antiinflammatory effect was produced by β-patchoulene (β-PAO) on LPSstimulated RAW 264.7 macrophages (Yang et al., 2017). The underlying mechanism was associated with the inhibition of TNF-α, IL-1β, and IL-6 biosynthesis followed by upregulation of IL-10 expression. Moreover, NO and PGE2 levels were remarkably reduced due to the suppression of iNOS (inducible nitric-oxide synthase), NF-κB, and COX-2 signaling pathways (Zhang et al., 2016). Patchoulene epoxide was found to be superior to β-patchoulene in limiting inflammation. After oxidation β-PAE changes to PAO and downregulates the production of IL-1β, IL-12, TNF-α, and monocyte chemotactic protein-1 (MCP-1) (Wu et al., 2018). 18.6.2.10 Antitumor effect The patchouli aqueous extract was shown to overcome the resistance of endometrial cancer against paclitaxel (Sun et al., 2018). Patchouli alcohol (PA) also inhibited the A549 human lung cancer cell line by activation of caspase-9 and -3 and modulation of mitochondriamediated apoptosis. The underlying mode of action involved the inhibition of phosphorylation processes of EGFR (epidermal growth factor receptor) and the mediators of the JNK (c-Jun N-terminal kinase) signaling pathway (Lu et al., 2016). The PA also inhibited MV4–11 human leukemia cell line by inducing the apoptosis. The underlying mechanism may be linked with the decrease in phospho-pyruvate kinase M2 (p-PKM2), and NF-κB and, upregulation of caspase-3 expression (Yang et al., 2016). Pogostone produced an antiproliferative effect on the SGC-996 gall bladder carcinoma cell line. The underlying mechanism involved the upregulation of caspase-9 and -3 and poly-ADP-ribose polymerase-1 (PARP-1) expression, enhance the Bax/Bcl-2 ratio and downregulation of cyclin D1, A and B expression (Wu et al., 2017). Overall, pogostone produced the antitumor effect by regulating apoptosis- and cell cycle-regulated proteins. 18.6.2.11 Analgesic effect The patchouli relieved the pain in acetic acid-induced writhing model in mice by reducing its intensity (Guo et al., 2016). The patchouli alcohol is associated with the simultaneous upregulation of MOR (mu-opioid receptor) and decline in intracellular calcium levels. The

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role of PA with respect to modulating MOR should be further studied as a potential analgesic (Thirkettle-Watts, 2016). 18.6.2.12 Immunoregulatory effect The patchouli alcohol and pogostone enhance the synthesis and production of secretory immunoglobulin A (SIgA). The function of SIgA is to promote the mucosal immunity against bacteria, viruses, food antigens, and toxins (Sheng et al., 2017). The pogostone is also linked with the repair of intestinal epithelium and protection of integrity of the intestinal mucosal barrier (Liu et al., 2016b). 18.6.2.13 Antimicrobial effect The patchouli aqueous extract inhibited the multidrug resistant Vibrio harveyi with an MIC of 31.25 mg mL1. The underlying mechanism includes the inhibition of biofilm formation via induction of luxR and flab and inhibition of hfq, luxS, and ompW genes expression ( Ji et al., 2018). Pogotone, a constituent of patchouli oil, exhibited antimicrobial activity against Streptococcus mutans with an MIC of 25 mg mL1 and Staphylococcus aureus and Shigella flexneri with an MIC of 12.5 mg mL1 (Adhavan et al., 2017). The underlying mechanism may involve the interaction with cell membrane proteins and alteration of cell membrane permeability (Wang et al., 2018). Overall, patchouli essential oil has effect on different bacterial strains like Aeromonas veronii, Candida albicans, Klebsiella pneumonia, Escherichia coli, Acenitobacter baumanii, Staphyllococcus aureus, Enterococcus faecalis, Salmonella enteric, and Pseudomonas aeruginosa (Hammer et al., 1999). Patchouli alcohol (as shown in Fig. 18.3) selectively inhibits the Helicobacter pylori without producing any negative impact on the normal gut microbiota (Xu et al., 2017). In addition, it inhibits the urease protein by inhibiting the protein maturation and increasing the susceptibility of the bacterial strain to the acid (Lian et al., 2017, 2019a). The underlying mechanism in reduction of urease activity associated with H. pylori also involves the downregulation of ureB, nixA, ureI, and ureE genes and increase in the antimicrobial activity mediated by macrophage (Lian et al., 2019b). It also produced the cytoprotective effect by limiting the H. pylori induced injury to the epithelial cells. It also protects against the urease associated cytotoxicity of GES-1 (gastric epithelial cells) (Xie et al., 2016). In addition, patchouli alcohol was also associated with the increase in the SOD and CAT activities and reducing ROS and MDA levels. It inhibits the synthesis of bacterial virulence factors and regulates the NLRP3 and NF-κB signaling pathways (Lian et al., 2018). PA also inhibits the production of pro-inflammatory cytokines activated by H. pylori (Ren et al., 2019). Patchouli essential oil inhibit fungal growth. It has fungal activity against a population of Aspergillus species (Kocevski et al., 2013). The pogostone in the patchouli oil was found to be helpful in treatment of Candida infections (Li et al., 2012a). Moreover, molecular docking studies suggested the promising antifungal agents by suitable structural modifications of pogostone analogues (Yi et al., 2013). Patchouli essential oil inhibit influenza virus by decreasing the virulence of pathogenic organism and also by increasing the recognition and response of innate immunity (Li et al., 2012b).

18.7 Safety, toxicity, and regulation

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FIG. 18.3

The mode of action of patchouli alcohol on Helicobacter pylori induced ulcer ( Junren et al., 2021). Adopted from Junren, C., Xiaofang, X., Mengting, L., Qiuyun, X., Gangmin, L., Huiqiong, Z., Guanru, C., Xin, X., Yanpeng, Y., Fu, P., Cheng, P., 2021. Pharmacological activities and mechanisms of action of Pogostemon cablin Benth: a review. Chin. Medi. 16 (1), 1–20.

18.6.2.14 Insecticidal effect Insects and termites are responsible for destruction of crops and insecticides which we are using for crop protection result in environmental hazards. Botanical insecticides are in use now a days because of less response against the organism which are not our target audience (Nerio et al., 2010). Patchouli essential oil has many biologically active ingredients which are responsible for not only its botanical insecticidal activity and also have effect on the development, replication, and activity of insects (Zhu et al., 2003; Machial et al., 2010; Park and Park, 2012).

18.7 Safety, toxicity, and regulation The PEO has the GRAS (“generally recognized as safe”) status under no. 2838 (Hall and Oser, 1965). The European Chemical Agency (ECHA) also enlists it under EC list no. 616944-7 (Patchouli Oil, 2021). Last, but not the least, the Chinese positive list of ingredients also includes it in cosmetics under no. 02634 (Inventory of Existing Cosmetic Ingredients in China, 2021).

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The essential oil including PEO (patchouli essential oil) may cause contact allergy (de Groot and Schmidt, 2016). The risk for allergenic and toxicological tendency of patchoulol containing products was assessed and the patchouli was found to have lower order of acute toxicity 50 mg kg1 body weight/day with no genotoxicity and mutagenicity (Belsito et al., 2008). Moreover, patchoulol has very sensitization potential at currently used concentrations (Bhatia et al., 2008). Additionally, PEO was administered orally as much as 100 times the maximum daily intake in humans for 90 days. After the study, no adverse effects incurred on the food intake, growth and development, hematological, renal, and liver profiles. This was also confirmed by normal gross and microscopic appearance of major organs at autopsy (Oser et al., 1965). Overall, PEO has been tested for the skin allergy causing ability. In an investigation using patch test in 183 patients, 3 patients gave “strongly positive” and 8 patients gave “weakly positive” reactions (Mitchell, 1975). Similarly, the clinical data obtained in 1606 patients showed 0.8% positive reactions to PEO (10% in petrolatum) (Frosch et al., 2002). In an another study, PEO 10% in petrolatum was patch tested in 5539 patients out of which 1% gave a positive reaction (Geier and Uter, 2015). The allergic reaction may be due to six constituents present in the PEO, such as linalool, limonene, farnesol (Cornwell, 2010), citronellol (de Rijke et al., 1997), isophorone, and eugenol (van Beek and Joulain, 2018). Out of these, isophorone is officially recognized as a CMR (carcinogen, mutagen, reprotoxic) and therefore is strictly prohibited as a fragrance ingredient (International Fragrance Association (IFRA), 2009). Similarly, the eugenol occurs in very low concentrations (ppm) (van Beek and Joulain, 2018) in PEO. However, a validated GC-MS protocol can detect and quantify these trace compounds (European Committee for Standardization, 2012).

18.8 Trade, storage stability, and transport The PEO comprises one of the most important fragrant material available for manufacture of scents and perfumes (Haarmann and Reimer, 1985). Indonesia has the 90% share (which is around 1200–1300 metric tons per annum) in global production of PEO (Howarth, 2015). It is the tenth most important essential oil in terms of providing bulk (Lawrence, 2009). A good quality oil is purchased at US$ 61–63 kg1 (van Beek and Joulain, 2018) but it could be as high as $ 150 kg1 (Frister and Beutel, 2015). The turnover of PEO falls under the 15 most important essential oils (Verlet, 1995). The estimated annual sales of PEO are approximately $75 million. Patchouli essential oils usually have longer shelf life. They must be stored away from direct sun exposure, humidity, and air. Patchouli essential oils are usually stored in air tight aluminum container in cool dry place (van Beek and Joulain, 2018). In Indonesia patchouli essential oil is produced and traded by producers and exporter. Some producers of Indonesia have facilities of exporting patchouli essential oil while large number of exporters does not have distillation facilities therefore local trading intermediaries are responsible for cleaning and trading of oil. In China production of patchouli essential oil is done by central surveillance and only officially approved bodies are responsible for their export. While in Taiwan, Malaysia, and Brazil for export of patchouli essential oil private

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enterprise conditions are usually applied and their essential oil production is very less. A large amount of internationally-traded patchouli essential oil has been done by Singapore. Singapore trading is famous because of their good cleaning services, grading, bulking, and fast delivery of patchouli oil (Robbins, 1982).

18.9 Conclusion The PEO comprises sesquiterpenes which represent greater than 95% of its composition. It attains the required fragrance in the aged samples rather than freshly distilled ones. Although patchoulol, norpatchoulenol, and nortetracyclopatchoulol impart earthy moldy note, but there are more of odor imparting components which account for the richness and quality of PEO. A rise in odor quality over the period of time still demands chemical and olfactory research to explain the observed phenomenon. Improved separation and identification techniques like GC-MS has enabled the quick recognition of complex mixtures of PEO and significantly reduce the risk of adulteration. It has a great significance in perfumery, medicinal, and soap industries since olden times and is increasing day by day. Therefore, there is an open venue for producing even better varieties of the patchouli plant which would give better yield of the oil to be utilized in various above-mentioned applications.

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C H A P T E R

19 Clary sage essential oil Monika Hansa, Deekshab, Gulzar Ahmad Nayikc, and Ameeta Salariaa a

Department of Food Science and Technology, Padma Shri Padma Sachdev, Government PG College for Women Gandhi Nagar, Jammu, Jammu & Kashmir, India bDepartment of Pharmacology, Delhi Institute of Pharmaceutical Sciences and Research (DIPSAR), New Delhi, India cDepartment of Food Science & Technology, Government Degree College Shopian, Srinagar, Jammu & Kashmir, India

19.1 Introduction Clary sage (Salvia sclarea Linn.), a xerophytic biennial/perennial herb, is native of Mediterranean area, viz., Western Asia, North Africa, and Southern Europe, which belongs to the Lamiaceae family. Clary sage cultivation has grown substantially on a commercial scale around the world, mostly for its essential oils (Peana and Moretti, 2002). To represent these beneficial plants, Pliny, a Roman writer, coined the Latin term Salvia, which means “to heal.” The entire plant of clary sage or juices helped in clearing away the mucus from eyes or related eye ailments. Salvia sclarea has traditionally been recognized among the most valuable medicinal plants native to Mediterranean nations, with applications in medicine, cosmetics, and perfumery (Durling et al., 2007; Kong et al., 2010). Antidiarrheal and tranquilizer drugs are made from various components of the plant in traditional medical system (Baytop, 1999). It has been used in treatment and management of neural polyarthritis and acute rheumatism. Clary sage plant is distinct from common sage or Salvia officinalis. It differs from common sage morphologically in its large leaf size and bluish white hue (Ali et al., 2015). Essential oils which are extracted from aromatic herbs or shrubs contain a mixture of secondary metabolites, viz., benzenoids, phenylpropanoids, monoterpenoids, and sesquiterpenoids, each has its own distinct aroma. Majority of essential oils contains between 100 and 250 components, while others, such as lavender, geranium, and rosemary, have up to 500 (Lizarraga-Valderrama, 2021). Plants synthesize them to protect them against arthropod or other predators. Clary sage oil, isolated from its leaves and flowers, finds use in aromatherapy,

Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00001-3

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flavoring, and medicine. Linalyl acetate and linalool are two important components of essential oil of clary sage. Another key component viz. sclareol, is utilized as a raw material in the production of Ambrox, a fragrance ingredient. A range of ecological, geographical, and environmental factors influence the composition of clary sage oil. The essential oil of clary sage is beneficial for relieving stress and depression during primary dysmenorrhea. Women can benefit from clary sage oil-based aromatherapy during their menstrual cycle, childbirth, and menopause. It was reported that when women used clary sage essential oil during early labor, about 86% of them thought it was efficient, and over 70% of them did not take intravenous oxytocin thereafter (Burns et al., 2000). S. sclarea essential oil is used to improve labor contractions in Russia since it is safe, nonsensitizing and nonirritant. Clary sage oil helps with muscle discomfort and suffering during labor, and it is also recognized to be a good therapy for postpartum depression. It has antibacterial, antifungal, antiviral, antiinflammatory, antioxidant, anxiolytic, antidiabetic, and cytotoxic properties (Mahboubi, 2020). Besides medical applications, the essential oil of clary sage is also used in culinary and cosmetics industries, winemaking, and as a tobacco flavoring ingredient (Dzumayev et al., 1995). Vital or Essential oils are becoming increasingly popular as natural food preservatives to help perishable foods last longer due to the hazards linked with chemical preservatives. Salvia sclarea essential oil has antimicrobial abilities and can therefore be used as a preservative to prevent food deterioration (Kozics et al., 2013). Furthermore, bioinsecticides based on plant essential oils is gaining recognition since they include volatile compounds which may function as insect repellents or attractants, as well as deterrents to feeding or oviposition. They are regarded as a safer option since they are eco-friendly, nontoxic toward nontarget organisms and have a low impact on human heath (Kim et al., 2012).

19.2 Clary sage oil production and chemical composition Salvia sclarea is a popular aromatic herb used in cosmetics and perfumes all over the world (Tibaldi et al., 2010; Angelova et al., 2016). Clary sage oil has high demand, and a plentiful flowering that produces large yield of essential oil is desired (Zutic et al., 2016). Steam distillation of fresh plant material is commonly used to extract essential oil. The oil content is at its highest when the flowers are fully mature. This is due to the fact that the calyces have more essential oil glands per unit area. Fully mature flower spikes should be collected to obtain the highest oil production (Peana and Moretti, 2002). The essential oil of clary sage has key components such as geranyl acetate, linalyl acetate, linalool, terpineol, and α-terpinyl acetate (Pitarokili et al., 2002; Fraternale et al., 2005; Farka et al., 2005). According to Souleles and Argyriadou (1997), compositions of wild oil of clary sage isolated from leaves and flowers, were linalool (17.2%), after that linalyl acetate (14.3%), geraniol (6.5%), geranyl acetate (7.5%), terpineol (15.1%), nerol (5.5%), neryl acetate (5.2%) and sclareol (5.2%). Taarit et al. (2014) discovered that primary components of essential oil of seed isolated from Salvia sclarea were monoterpenes (47.9%) and sesquiterpenes (29.4%). 13-epi-manool, a diterpene compound, was found at 0.59%, and phenols (such as thymol and carvacrol) 2.0%. Linalool (24.2%), geraniol (2.8%), linalyl acetate (6.9%) and geranyl acetate (1.9%) were found among the oxygenated monoterpenes. Sesquiterpenes such as Germacrene-D (5.8%), bicyclogermacrene (4.2%), and α-copaene (4.1%) were found in the oil.

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Diterpenoid components isolated from the hairy roots of clary sage, using a dichloromethane solvent, were aethiopinone, 1-oxoaethiopinone, ferruginol, and salvipisone (Kuzma et al., 2007). The diterpene chemicals isolated from acetone extract of clary sage included Sclareol, ferruginol, microstegiol, candidissiol, manool, salvipisone, 7-oxoroyleanone, 2,3-dehydrosalvipisone, and 7-oxoferruginol-18-al (Ulubelen et al., 1994). Nitrogen has an impact on clary sage’s growth, biomass, and oil content. Application of nitrogen fertilizer promoted the growth and development of clary sage in comparison to control (Sharma and Kumar, 2012). In comparison to the control, 1.5 g N/plant resulted in a significantly greater spread of plant canopy and number of flowering stalks/plant. Application of nitrogen fertilizer has a positive impact on plant vegetative growth as it activates the photosynthesis and other metabolic processes in plants. Oil composition is impacted by several factors such as crop varieties, environmental factors, growing techniques, fertilizer use, frequency and extent of irrigation etc. (Baser, 2002; Mishra and Negi, 2009). Nitrogen fertilizer led to significant difference in oil composition as reported by Sharma and Kumar (2012). Treatment of 3.0 g N/plant increased the percentage of key components, for example, linalool (19.10%), α-terpineol (7.15%), and linalyl acetate (32.11%) in comparison to other treatments. Nitrogen is linked to the de novo synthesis of metabolic components in the building of dry matter, as well as the synthesis of essential oils, which explains the increase in oil content in response to nitrogen fertilization. For growth, biomass, and desired chemicals in oil content, 3.0 g N/plant was determined to be optimal (Sharma and Kumar, 2012). Kumar et al. (2017) investigated the effects of high [CO2] and temperatures on growth and essential oil content in Salvia sclarea. Experiments were conducted at ambient CO2 levels, 390 μmol mol 1 CO2 as well as elevated CO2 levels, 550  30 μmol mol 1 CO2 (referred as Free Air [CO2] Enrichment, FACE). Similarly, temperature parameter was maintained at ambient and elevated temperature (referred as Free Air Temperature Increment, FATI, which was nearly 2.5–3.0°C above ambient temperature). When comparing control and enhanced temperature and CO2, total biomass was found to be 16.2% and 21.4% higher, respectively. The number of leaves per plant and the area of leaves per plant improved in elevated temperature conditions, whereas these parameters declined under elevated CO2. Under FACE conditions, the amount of glutathione rose by 18.3%. Antioxidative enzyme induction was also detected. Under FATI conditions, concentration of violaxanthin lowered by 23% and neoxanthin lowered by 18%, whereas the state of de-epoxidation increased by 16% in comparison to control. In both FATI and FACE settings, the components of essential oils, linalyl acetate, and linalool, rose dramatically. Mahboubi (2020) compared the constituents present in essential oil extracted out of different plant parts of clary sage from across different countries. The oil composition derived from various plant parts of clary sage from Greece was compared. Linalool (17.2%) was the most abundant chemical in clary sage flower and leaf oil, followed by terpineol (15.1%), linalyl acetate (14.3%), geraniol (6.5%), nerol (5.5%), neryl acetate (5.2%), and sclareol (5.2%), respectively while oil from aerial parts comprised of linalyl acetate (19.8 to 31.1%), followed by linalool (18.5%–30.4%), geranyl acetate (4.4%–12.1%), α-terpineol (5.1%–7.6%) (Pitarokili et al., 2002). Essential oil extracted from leaves of Slovak Republic and flowers of S. sclarea was also analyzed (Farka et al., 2005). Linalool (18.9%), linalyl acetate (13.7%), sclareol (15.7%), α-terpineol (6.5%), germacrene D (5.0%) and geranyl acetate (4.3%) were significant components in essential oil from flowers whereas germacrene D (28.8%), bicyclogermacrene (12.5%), spathulenol (10.1%), caryophyllene oxide (6.2%) and α-copaene (6.0%) were the main

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components from leaf oil. Linalyl acetate (41.7%–51.4%), linalool (19.3%–31.4%) and geranyl acetate (1.9%–3.5%) were among the chief components in essential oil derived from accessions of clary sage from India (Yaseen et al., 2015). The major components of S. sclarea oil from Hungary were linalyl acetate (57.94%), followed by linalool (24.1%), α-terpineol (5.39%) and geranyl acetate (3.04%) (Blasko et al., 2017). The biological properties of Salvia sclarea are significantly influenced by its chemical makeup. The main compounds present in clary sage oil, along with their chemical structures, are summarized in Table 19.1.

TABLE 19.1 Major chemical compounds in Salvia sclarea essential oil. Compounds Monoterpene alcohols

Monoterpene esters

Structure

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TABLE 19.1 Major chemical compounds in Salvia sclarea essential oil—cont’d Compounds

Structure

Sesquiterpene hydrocarbons

Oxygenated sesquiterpenes

Diterpenes

19.3 Extraction techniques (distillation) Various methods are employed for extraction of essential oils from plants (Fig. 19.1). The extraction procedure determines the quality as well as quantity of essential oil (Park and Tak, 2016). Improper extraction methods might result in loss of biological activity and inherent characteristics. Extreme conditions can result in discoloration, odor/flavor, and physical changes such as increased viscosity. These alterations in the extracted essential oil need to be avoided (Tongnuanchan and Benjakul, 2014).

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Distillation Steam distillation Hydrodistillation Hydrodiffusion

FIG. 19.1

Solvent extraction Solvent Supercritical carbondioxide Subcritical water

Solvent free

combination-

microwave

solvent +steam

Various extraction methods used to produce essential oils.

19.3.1 Distillation 19.3.1.1 Steam distillation Steam distillation is a basic process for extraction of essential oils. In most cases, the plant sample is immersed in boiling water or steam heated. Application of heat leads to the breakage and disruption of structure of cell the plant material. Aroma compounds or essential oils are released as a result of this process (Babu and Kaul, 2005). Masango (2005) designed and operated a new steam distillation process for extracting essential oils with the aim to enhance the oil production while reducing the polar component loss in wastewater. The system is comprised of a densely packed bed of plant materials that rests on top source of hot steam. Only steam is allowed to pass through it, and it is kept isolated from plant tissues by boiling water. As a result, the process uses the least amount of steam possible, resulting in a little amount of water in the distillate. Water soluble compounds dissolve minimal in the aqueous component of the condensate. 19.3.1.2 Hydrodistillation The hydrodistillation method is employed to obtain essential oil from plant materials including wood and flowers. It is commonly employed to separate water insoluble compounds with a high boiling point. The procedure entails thorough immersion of plant tissue in water followed by boiling. The surrounding water acts as a barrier, protecting the essential oils that have been extracted to some extent. This approach has the advantage of being able to distil plant material at temperatures below 100 degrees Celsius (Tongnuanchan and Benjakul, 2014). Farka et al. (2005) employed hydrodistillation method to extract essential oils from clary sage dried flowers and foliage. Before drying over anhydrous sodium sulfate, the oils were separated and dissolved in hexane. 19.3.1.3 Hydrodiffusion The sole difference between hydrodiffusion and steam distillation is how steam is injected. Steam is introduced in hydrodiffusion process from top of the plant material, whereas steam is introduced from the bottom in case of steam distillation. Hydrodiffusion is advantageous over steam distillation as it has short processing time and high oil production (Tongnuanchan and Benjakul, 2014). This approach is employed in case of dried plant material to prevent any damage from boiling water (Vian et al., 2008).

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19.3.2 Solvent extraction For delicate or fragile flower materials that cannot withstand the heat of steam distillation, traditional solvent extraction has been used. Extraction can be done with a variety of solvents, for example, acetone, methanol or ethanol, hexane, petroleum ether (Kosar et al., 2005). Essential oil is derived by heating solvent along with the plant material and then filtering it. After that, the filtrate is concentrated by evaporating the solvent. Essential oil is obtained by mixing the concentrate with pure alcohol and distilling it at low temperatures. The absolute oil is recovered after the alcohol has evaporated. Since this procedure is relatively time taking, the oils produced by this approach are more expensive (Li et al., 2009). 19.3.2.1 Supercritical carbon dioxide Traditional methods like solvent extraction and steam distillation have certain drawbacks, such as long preparation time and the usage of large amounts of organic solvents (Deng et al., 2005). Furthermore, poor extraction efficiency, unsaturated chemical degradation, loss of few volatile compounds, and hazardous solvent residue in the extract are additional factors that need to be considered ( Jimenez-Carmona et al., 1999; Glisic et al., 2007; Gironi and Maschietti, 2008). Supercritical fluids, like as CO2, offer an excellent extraction medium for essential oils. CO2 becomes a liquid at high pressure, making it an extremely inert and harmless medium for extracting aromatic compounds from raw materials. At normal atmospheric pressure and temperature, the liquid CO2 simply converts to a gas, which then evaporates leaving no solvent behind in the final product. Due to the mild critical conditions, widely used supercritical fluid is carbon dioxide (Sen˜ora´ns et al., 2000). The components of clary sage essential oil extracted by hydrodistillation and supercritical fluid extraction were compared (Ronyai et al., 1999). The percentage of linalool, neryl acetate, α-terpineol, myrcene, p-cymene, and geranyl acetate were greater in the distilled oil than that which is obtained by supercritical fluid extraction. In the distilled oil and supercritical fluid extraction, the ratio of linalyl acetate to linalool was 0.7 and 9.6, respectively, showing a significant difference. Oil recovered by supercritical fluid extraction only contained sclareol. 19.3.2.2 Subcritical water Subcritical water or pressurized hot water is utilized as and extractant at high temperatures (range 100–374°C) and high pressure. This method was found to be 5.1 times efficient than the hydrodistillation method ( Jimenez-Carmona et al., 1999). This is advantageous in terms of cost, time and recovery of essential oils from plant material. Kubatova et al. (2001) extracted lactones from the roots of Piper methysticum, and discovered that shorter times were required for extraction with subcritical water at 175°C. On the contrary, extraction with Soxhlet method gave lower yield by 40%–60% compared to subcritical water.

19.3.3 Solvent-free microwave extraction (SFME) Considering disadvantages associated with solvent based methods, this method (SFME) is a rapid method which involves heating in microwave and dry distillation method, and is carried out at atmospheric pressure without using solvent or water. The microwave method has advantageous over the traditional methods in terms of shorter extraction times, greater yields,

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cost effective, and cleaner method as described by Ferhat et al. (2007). This procedure leaves no residue because there is no solvent involved. The quantity and chemical makeup of an essential oil produced from caraway seeds without the use of solvents, such as microwave dry-diffusion and gravity, were comparable to those produced by hydrodistillation. In terms of processing time, the former method was superior to the later (45 min v/s 300 min), energy savings and also waste reduction (Farhat et al., 2010).

19.3.4 Combination methods Li et al. (2009) used a combination method, which included an organic solvent and steam distillation, to extract essential oil from the seeds of Cuminum cyminum. Temperature had the greatest impact on oleoresin yield, after that following extraction time and particle size. Ideal temperature, extraction time and particle size were found at 20°C, 8 h and 80 mesh, respectively. Three extraction methods viz. supercritical fluid extraction, hydrodistillation, and a combination method (steam distillation and an organic solvent with a low boiling point) were compared. Essential oil of C. cyminum included a total of 45 compounds, demonstrating that the composition of different extraction procedures was largely consistent, despite significant differences in relative concentration of the compounds. Combination method (low boiling point of organic solvent and steam distillation) was determined to be best approach for generating high grade essential oil at a reasonable cost among the three methods evaluated. A combination method, viz. solvent extraction and steam distillation (SE-SD), was found to be the most effective method for extracting high grade essential oil from waste tobacco leaves (Zhang et al., 2012). Essential oil obtained by the combination method had a higher quality and thus a greater value based on its general characteristics.

19.4 Characterization of essential oil components A variety of factors impact the chemical content of clary sage oil, including method of isolation, source of the plant, and plant tissue used for isolation (Kuzma et al., 2009; Sharopov and Setzer, 2012). Wild clary sage was used to extract essential oil from Tajikistan using the process of hydrodistillation. There were 59 compounds found in total accounting 94.2% of oil content. Among key compounds, linalyl acetate (39.2%) followed by linalool (12.5%), germacrene D (11.4%), α-terpineol (5.5%), geranyl acetate (3.5%), and (E)-caryophyllene (2.4%) were found. Tajik S. sclarea oil has a chemical composition equivalent to that of commercial grade S. sclarea oils, with the exception of high concentrations of linalyl acetate and linalool (Sharopov and Setzer, 2012). The cultivation conditions for clary sage have a big impact on its essential oil components (Peana et al., 1999). For instance, salt stress has a great impact on essential oil synthesis in clary sage as reported by Taarit et al. (2011). A moderate salt concentration of 25 mM enhanced essential oil yield substantially, whereas further increase in salinity lowered the oil yield, notably at 75 mM. In control experiment, the primary compounds of leaf oil were sesquiterpene hydrocarbons (44.71%) and diterpenes (26.62%). Germacrene-D was the most abundant compound (28.00%) in sesquiterpene hydrocarbons while diterpenes had manoyle oxide and

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phytol (12.77% each). On contrary, sesquiterpene hydrocarbons were reduced by 60% mainly germacrene-D, after the treatment with 25 mM salt. On the contrary, monoterpene ketones, particularly α-thujone (13.74%), increased by 85.88%. Despite the decrease in diterpenes at 25 mM NaCl, manool (15.23%) remained the most abundant component of essential oil, after that α-thujone (13.74%). At 50 mM salt concentration, maximum increase in biosynthesis of monoterpene hydrocarbons was observed (42.23%), α-thujene being the most abundant compound (36.73%). Substantial variations in the percentage of essential oil components were observed at 75 mM salt concentration, with considerable proportion of oxygenated sesquiterpenes (25.93%) and monoterpene hydrocarbons (21.89%). The primary constituents being α-thujene (14.87%), followed by viridiflorol (11.89%), phytol (9.28%), camphor (8.49%), caryophyllene oxide (8.44%), and α-pinene (6.54%). Using GC–MS method, Raafat and Habib (2018) investigated the phytochemical content of essential oils from two distinct areas of Lebanon, viz., Beirut and Taanayel. 67 main compounds were discovered, representing 86.80% of Beirut and 85.36% of Taanayel. 21 oxygenated monoterpenes (66.28% and 66.04% for Beirut and Taanayel, respectively), 13 monoterpene hydrocarbons (7.92% and 7.68% for Beirut and Taanayel, respectively), 19 sesquiterpenehydrocarbons (5.94% and 5.70% for Beirut and Taanayel, respectively), as well as 18 oxygenated sesquiterpenes (5.22% and 5.70% for Beirut and Taanayel, respectively) were ascertained.

19.5 Chemistry and properties Clary sage oil is a light yellow or pale olive liquid with distinctive odor. It has a relative density of 0.890–0.908, a refractive index in the range of 1.456–1.466, optical rotation between 26° and 10° and a maximum acid value of 1.0 (European Pharmacopoeia, 2010). The oil comprises of oxygenated monoterpenes, linalyl acetate, linalool and other terpene alcohols, and their acetates. Antibacterial, antifungal, antiviral, antioxidant, antiinflammatory, and insecticidal activities have been reported in clary sage oil. It is exclusively used in perfumery and other cosmetic products (Tasheva et al., 2020).

19.6 Applications 19.6.1 Pharmacological 19.6.1.1 Antianxiolytic Essential oils have grown in popularity as a complementary medicine to treat depression and anxiety for two reasons: first, they possess pharmacological properties and second, they eliminate the adverse effects associated with long-term use of synthetic anxiolytic and antidepressant pharmaceuticals (Lizarraga-Valderrama, 2021). Examples of essential oils popularly used to treat depression and stress are lavender (Lavandula angustifolia), bergamot (Citrus aurantium), lemon (Citrus limon), sandalwood (Santalum album), clary sage (Salvia sclarea), orange (Citrus sinensis), roman chamomile (Anthemis nobilis), rose (Rosa damascena), and rose geranium (Pelargonium spp.). Fear, anxiety, and delusions can all be alleviated with clary sage oil (Dweck, 2000). Clary sage essential oil has a depressant effect on CNS in mice

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(Peana and Moretti, 2002). The presence of certain oxygenated molecules, for instance, linalool, linalyl acetate, α-terpineol and α-terpinyl acetate, seems to be responsible for the pharmacological effects. 19.6.1.2 Significance in women health Clary sage oil is beneficial in women, since it helps to regulate menstruation, childbirth and menopause. Because of its analgesic and soothing characteristics, clary sage oil is beneficial during childbirth (Burns and Blamey, 1994). Aromatherapy may be beneficial in women who suffer from menstrual cramps or dysmenorrhea. Han et al. (2006) suggested that aromatherapy employing lavender, rose oil, or clary sage helps to relieve menstruation cramps. Sclareol, a diterpene compound derived from Salvia sclarea, is often used in food and cosmetic sector as a supplement. In addition, it has the ability to alleviate the symptoms of dysmenorrhea. It has been successful in reducing the severity of dysmenorrhea when used as an abdominal massage oil (Mahboubi, 2020). Wong et al. (2020) demonstrated the potential effect of sclareol on dysmenorrhea as well as possible mechanism of action. It was discovered that sclareol reduced dysmenorrhea by decreasing the protein expression of oxytocin receptor, myosin light-chain kinase, cyclooxygenase-2, phosphorylated extracellular signal-regulated kinase, p-p38, and p-MLC20 (phosphorylated myosin light chain) and also modulated the intracellular calcium concentration. As a result, sclareol might help with primary dysmenorrhea and inflammation. Ou et al. (2012) analyzed impact of blended essential oil on menstrual cramps in subjects suffering from primary dysmenorrhea. In order to study the impact, lavender, clary sage, and marjoram oils were combined in a 2:1:1 proportion. Linalool, linalyl acetate, eucalyptol and β-caryophyllene were four main analgesic compounds found in blended essential oil, accounting for up to 79.29% of the total. Patients with primary dysmenorrhea were found to benefit from aromatic blended oil because it reduced the length of menstrual pain. Aromatherapy is an alternative or complementary therapy that has been used to stimulate and strengthen labor contractions (such as, inhalation of aroma of essential oil several times). Uterine contractions are triggered by the hormone oxytocin during labor. Clary sage essential oil contains sclareol, which has a structure identical to estrogen and is anticipated to produce estrogen-like effects. As estrogen promotes the release of oxytocin, a higher absorption of sclareol into the bloodstream should result in a higher oxytocin level. Tadokoro et al. (2017) assessed the level of salivary oxytocin in term-pregnant women after inhaling aroma of clary sage oil. Inhalation of clary sage oil increased oxytocin levels but showed no effect on uterine contractions. During the intervention, there was no adverse effect observed on the fetal heart rate. 19.6.1.3 Antibacterial Antibacterial activity is found in clary sage extract and essential oil. Cui et al. (2015) showed that Salvia sclarea oil had a broad antibacterial range and worked as an efficient bacterial inhibitor and bactericide. Clary sage oil exhibited comparable bacteriostatic and bactericidal efficacy against gram-positive (examples, Bacillus subtilis, Staphylococcus aureus) as well as gram-negative bacteria (examples, Escherichia coli, Bacillus pumilus, Salmonella typhimurium, Klebsiella pneumoniae, Pseudomonas aeruginosa). Minimum inhibitory concentrations (MIC) and minimum bacteriocidal concentrations (MBC) of various pathogens were calculated to be 0.05% and 0.1%, respectively. It was discovered that the essential oil of Salvia sclarea disrupted

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the cell membrane and altered its permeability, allowing material from inside the cell to escape, including macromolecular compounds, ATP, and DNA (Cui et al., 2015). Similarly, Kuzma et al. (2009) found the most vulnerable bacterium to clary sage oil was Escherichia coli. MIC values were calculated to be 10.0 and 5.0 mg mL 1 for S. aureus and S. epidermidis respectively.

19.6.1.4 Antifungal Essential oils possess appreciable antifungal activity as demonstrated in several studies. Dzamic et al. (2008) evaluated antifungal property of clary sage oil. Fungicidal activity was detected against several fungal species such as Aspergillus, Penicillium, Fusarium species, and Trichoderma viride, at 25 μL/mL concentration. The Minimal fungicidal concentration (MFC) was obtained as 15 μL/mL for Mucor mucedo and Aspergillus viride, and 10μL/mL for Candida albicans. The oil exhibited both fungistatic and fungicidal activity against Cladosporium cladosporioides and Trichophyton menthagrophytes at doses of 2.5 μL/mL and 5.0 μL/mL, respectively. Cladosporium fulvum, Alternaria alternata, Phomopsis helianthi, and Phoma macdonaldii were the most susceptible fungi exhibiting MIC and MFC values of 2.5 μL/mL. Clary sage oil had appreciable antibacterial activity against bacteria, but it had limited antifungal efficacy against Candida albicans and Saccharomyces cerevisiae (Yousefzadi et al., 2007). In soil-borne pathogens and phytopathogenic fungi, such as Alernaria solani, Botritys cinerea, Fusarium oxysporum, and Rhizoctonia solani, clary sage oil completely suppressed mycelial growth (Pitarokili et al., 2002; Fraternale et al., 2005). Clary sage essential oil as well as linalool and linalyl acetate, led to disruption of plasma membrane and increased membrane fluidity in Candida albicans leading to cell death (Blasko et al., 2017). Linalool, linalyl acetate, and sclareol are principal components which are thought to be associated with antifungal potential of S. sclarea essential oil (Dzamic et al., 2008). It was discovered that Candida species was susceptible to linalyl acetate in comparison to linalool, whereas rust fungus was sensitive to linalool present in clary sage essential oil (Mahboubi, 2020). Linalyl acetate inhibited mycelial development to some extent. Thus, the presence of significant concentrations of linalool and linalyl acetate in S. sclarea oil could be related to its moderate antifungal activity (Dzamic et al., 2008). Tadtong et al. (2012) demonstrated antimicrobial effect of various blended essential oil preparations. Preparation 1 (lavender, clary sage and ylang mixed in a volume ratio of 3:4:3) and preparation 2 (petitgrain, clary sage and jasmine oil mixed in a volume ratio of 3:4:3) possessed antibacterial effect against Escherichia coli, Staphylococcus aureus and S. epidermidis, except Pseudomonas aeruginosa. Antifungal effect was also reported against Candida albicans. It was determined that preparation 1 had more antibacterial activity than preparation 2 against the microorganisms examined. Furthermore, Preparation 3 (lavender, clary sage, ylang ylang in a volume ratio of 4:4:2) possessed a greater antifungal effect than preparation 1 and 4 (lavender, clary sage, ylang ylang in a volume ratio of 2:4:4). It was found that the key compounds in blended essential oil preparations were linalool and linalyl acetate. Antibacterial effect of blended oil was suggested to be linked to the linalool and linalyl acetate levels. Blended oil compositions exhibited a synergistic antibacterial effect by accumulating and mixing the bioactive components (linalool and linalyl acetate) from various oils.

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19.6.1.5 Antiviral Essential oils possess antiviral activity in addition to antiinflammatory, antifungal, and other properties. Several investigations have shown that essential oils have antiviral action (Koch et al., 2008; Schnitzler et al., 2008). On basis of cytopathic impact reduction technique, 62 essential oils were checked for their antiviral efficacy (Choi, 2018). Eleven out of 62 essential oils (100 g/mL) possessed antiviral effect showing 30% reduction in cytopathic effects of influenza A/WS/33 virus. Furthermore, marjoram, clary sage and anise oils demonstrated greater than 52.8% antiviral activity. The content composition of the three oils differed significantly according to GC–MS analysis except linalool, which was a common compound among them. The most prevalent component in marjoram oil was 1, 8-cineole (64.61%), linalool (15.28%) and α-pinene (5.81%). Concentration of linalyl acetate (61.16%) was maximum in clary sage oil, followed by linalool (22.06%). trans-Anethole (82.78%) was the most abundant compound in anise oil, followed by estragole (8.21%) and linalool (2.74%). Based on the chemical constituents of above three oils, linalool appeared to be related to antiviral activity. Similarly, antiviral activity was observed in apigenin, linalool, and ursolic acid extracted from crude ethanolic extracts of Ocimum basilicum, tested against DNA/RNA viruses (Chiang et al., 2005). 19.6.1.6 Antidepressant and stress-relieving properties In rats, the antidepressant effect of clary sage oil at 5% (v/v) was examined (Seol et al., 2010). Clary oil’s antidepressant-like effect is strongly linked with regulation of the DAnergic pathway regulation. In another pilot study, the antidepressant effect of clary sage essential oil was examined among menopausal women. The changes in plasma neurotransmitter levels between two subject groups, normal and depression predisposition, were analyzed. Cortisol levels were substantially lower after inhaling clary sage oil, but levels of 5-hydroxytryptamine (5-HT) were higher in normal as well as depressed menopausal women (Lee et al., 2014). Endothelial dysfunction caused by prolonged immobilization stress was successfully treated with clary sage oil in rats. In comparison to the chronic immobilization stress group, therapy with 5%, 10%, and 20% clary sage oil considerably lowered the systolic blood pressure while 20% clary sage oil further reduced heart rate considerably. Corticosterone serum levels and malondialdehyde, indicators for chronic stress and oxidative stress, were both reduced by clary sage. Clary sage oil enhanced endothelial function in rats by increasing nitric oxide formation and eNOS levels while also lowering oxidative stress. Endothelial dysfunction can be reversed with the right concentration of clary sage oil. Clary sage oil might help prevent and cure stress-related cardiovascular disorders (Yang et al., 2014). 19.6.1.7 Cytotoxic S. sclarea oil has been shown to possess cytotoxic effect in different studies. Durgha et al. (2016) determined the cytotoxic effect of S. sclarea essential oil in HeLa cells. Growth of HeLa cells was suppressed in a dose dependent fashion with IC50 value determined at 80.69 μg/mL. In another study, clary sage essential oil showed great cytotoxic impact against the cell lines, NALM-6 and HL-60. Oil from in vitro regenerated S. sclarea plants demonstrated a higher cytotoxic effect against NALM-6 cell lines than in vivo plants (Kuzma et al., 2009). Increased cytotoxic activity could be due to higher levels of germacrene-D in essential oil derived from

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in vitro regenerated plants. Setzer et al. (2006) demonstrated the cytotoxic potential of Germacrene D which came out to be seven-fold stronger than α- pinene and limonene when tested against Hs 578T cell line. Furthermore, it was found to be six-fold stronger against Hs-578T and Hep-G2 than 1,8-cineole, linalool, 4-terpineol and α-terpineol. 19.6.1.8 Antioxidant Clary sage oil’s antioxidant efficacy has been studied in various antioxidant systems. Clary sage oil’s antidepressant and antistress properties are attributed to the herb’s antioxidant properties (Mahboubi, 2020). Acetone and chloroform extracts were assessed for antioxidant activities and both the extracts inhibited lipid peroxidation to a significant degree (Gulcin et al., 2004). Antioxidant effect of chloroform extract had a greater impact than acetone extract. Furthermore, α-tocopherol has lesser antioxidant activity than that of these extracts. Chloroform extract of Salvia sclarea > acetone extract of Salvia sclarea > α-tocopherol (standard) was the order in which peroxidation was inhibited. The reducing ability of chloroform and acetone extracts was found to be the same as in Fe3+–Fe2+ system. Chloroform and acetone extracts were evaluated in terms of reducing power to the standard antioxidants (α-Tocopherol, quercetin and butylated hydroxyanisole, BHA) and follows the order: BHA > α-tocopherol > quercetin > chloroform extract of Salvia sclarea > acetone extract of Salvia sclarea. Efficiency of ethanolic extract of S. sclarea was determined against lipopolysaccharide (LPS)-induced periodontitis in rats (Kostic et al., 2017). It was discovered that the inflammation was decreased, with considerably lower levels of IL-1β, IL-6, and TNF-α. Antioxidant effect of clary sage ethanol extract is due to the active component rosmarinic acid. 19.6.1.9 Antiinflammatory Linalyl acetate and Linalool are important components of essential oils’ antiinflammatory properties (Peana et al., 2002). Hepatoprotective properties of clary sage leaf oil were found in LPS-induced severe hepatic cell injury. Following treatment with various quantities of essential oil, there was a reduction in inflammation. At 100 μg of oil, necrosis and hepatocyte infiltration were faintly visible. Down regulation of iNOS (inducible nitric oxide synthase) was observed. Inhibition of HeLa cells was demonstrated using oil and IC50 was obtained as 80.69 μg/mL. Staining with propidium iodide (PI) showed the occurrence of programmed cell death in oil treated cells. Essential oil from clary sage could be added to herbal medicine preparations (Durgha et al., 2016). Ethanol extract of clary sage oil decreased inflammatory cytokines, such as IL-6, IL-1β, and TNF-α in rat gingival tissue, thereby inhibiting LPS-induced inflammation (Kostic et al., 2017). 19.6.1.10 Antidiabetic Several studies have suggested that Salvia sclarea essential oil has antidiabetic properties, suggesting it could be used as a supplementary medication in disease control. Essential oil derived from wild Salvia sclarea from two districts in Lebanon viz. Beirut (Bt) and Taanayel (Tl) was discovered to have antidiabetic properties (Raafat and Habib, 2018). There were five chemotypes detected in total, essential oils from Tl and Bt, belonged to chemotypes 5 and 1, respectively. Taanayel essential oil (chemotype 5) had a greater linalyl acetate concentration, but Beirut essential oil (chemotype 1) had a higher linalool content and was more antidiabetic.

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19.6.2 Agro-food The secondary metabolism of plants produces essential oils which provide protection to plants against pests and pathogens. Some of the essential oils may function as deterrent to herbivores while others may aid in communication with other plants or animals (Park and Tak, 2016). The role of essential oils as semiochemicals that benefit plants, insects, or both is demonstrated in several situations. Plant essential oil based bioinsecticides could serve as a potential alternative to routine chemical pesticides due to their lower environmental and human health risks (Isman, 2006). They can target multiple or novel sites in the insect body. Depending on their mode of action, some may act as repellants, or attractants, feeding or oviposition deterrents, or stimulants (Isman, 2006). Various plant essential oils were assessed for their fumigant toxicity against third instars of cecidomyiid gall midge, Camptomyia corticalis (Kim et al., 2012). The LC50 values determined for several plant oils such as caraway seed, clary sage, armoise, cassia, oregano, lemongrass, niaouli, spearmint, dalmatian sage, red thyme, bay, garlic, and pennyroyal ranged from 0.55 to 0.60 mg/cm3. Examples of few essential oil-based products which have been commercialized include cinnamon, eucalyptus and garlic. Preliminary studies, such as establishing stability, mode of action, optimal formulation and delivery methods, and so on, are required before developing essential oil-based products. These essential oils could be explored for creating innovative and effective C. corticalis control agents (Kim et al., 2012). Yoon and Tak (2018) investigated the repellant and miticidal properties of various plant essential oils against the adults of two-spotted spider mites (Tetranychus urticae). Clary sage oil has the strongest repelling activity of all the essential oil tested. Monoterpenes were found to be the primary component of clary sage oil. Linalyl acetate was the most abundant component amounting to 44.29% of the oil, followed by linalool (31.63%), geranyl acetate (4.70%), α-terpinyl acetate (4.24%), and α-terpineol (4.19%). To identify the active ingredient responsible for repellent activity, a compound elimination test was conducted. Upon exclusion of linalyl acetate, significant decrease in the repellent activity was observed. It was proved that linalyl acetate was the most prevalent and repellent component of clary sage oil, out of all the other components against T. urticae. An essential oil’s biological function varies greatly depending on its chemical composition (Isman et al., 2008). Salvia sclarea oil also limit the growth of some phytopathogenic fungi, making them a suitable alternative to chemical substances used in agronomic field, with the objective of minimizing pollution (Peana and Moretti, 2002).

19.6.3 Nonfood 19.6.3.1 Perfumery Sclareol is obtained extensively from cultivated clary sage. Sclareol is a diterpene compound and highly valued natural product in the perfume industry. The labdane Carbon structure of Sclareol, combined with its two hydroxyl groups has made it an ideal beginning source for the semi synthesis of a variety of commercial goods such as Ambrox and ambergris equivalents which are used in the manufacturing of exceptional fragrances (Caniard et al., 2012). Ambrox, regarded as one of the most valuable animal-derived fragrances, was formerly obtained from Ambra, a waxy material extracted from the whale’s digestive system.

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19.6.3.2 Cosmetics Essential oils are becoming more popular in skin care products because of their biological characteristics, including antimicrobial, antiinflammatory, antioxidant, antiseptic, antiseborrheic, and antikeratolytic capabilities. They assist in the treatment of skin-related issues as well as shield the skin from environmental harm. The active ingredients present in essential oils impart significant properties to skin care products which nourish the skin with essential minerals (Happy et al., 2021). Clary sage essential oil is effective in protecting DNA and protein damage caused by free radicals (Gulcin et al., 2004; Pop et al., 2016). The molecular species having an unpaired electron in an atomic orbital is known as a free radical and possess the ability to exist on their own. Due to their reactive nature, they can damage the skin. In addition, clary sage essential oil possesses astringent properties and hence imparts antiaging benefits to the skin. Proportion of Clary sage found in soaps is 0.01%–1%, detergents (0.001%–0.01%), creams and lotions (0.003%–0.03%), and perfumes (0.12%–0.8%). 19.6.3.3 Wound dressings and smart packaging Essential oils are widely utilized in various applications, for instance, food preservation, agriculture, pharmaceuticals owing to plethora of biological activities vested in them. Currently, encapsulation of essential oils within electrospun polymeric nanofibers has gotten a lot of publicity and could lead to a prolonged and more controlled release of these bioactive compounds (Zhang et al., 2017a). Electrospun mats infused with essential oils, such as, tea tree, thyme, cinnamon and lavender, have been shown to be effective as better wound dressings and smart food packaging (Wang and Mele, 2018). Poly lactic acid (PLA) fibers are biocompatible, biodegradable and mechanically strong, hence they are routinely used in food packaging, biomedical and textile (Gupta et al., 2007). Acetone solutions containing a polymer concentration in the range of 12.5% to 15.0% (w/v) are recommended for electrospinning PLA mats (Casasola et al., 2014; Zhang et al., 2017b). Wang and Mele (2018) used a 14% (w/v) polymer concentrate to make PLA fibers with a mean diameter of 1.1 μm without any defects. Densely connected fibers with a wrinkled surface developed after 10% (v/v) clary sage essential oil was added to the PLA/acetone solution. The antibacterial tests of electrospun fibers were conducted on E. coli and S. epidermidis. Only a small number of colony forming units (CFU) were observed in PLA/CS-EO mats, compared to a considerable number of colony forming units (CFU) detected in PLA fibrous mats without any essential oil. It was calculated that the PLA/CSEO mats had a 76.0% and 100% inactivation activity in both microorganism, i.e., E. coli and S. epidermidis, respectively. Clary sage essential oil influences the structure and surface characteristics of electrospun fibers as well as imparting bioactivity. The antibacterial characteristics of the fibers suggest that they can be used in biomedical applications as wound dressings to inhibit bacteria colonization and enhance skin regeneration.

19.7 Safety, toxicity and regulation Often, essential oils are harmless with no potential negative effects provided they are used appropriately. The dosage of essential oil is the crucial safety factor. Furthermore, essential oils are classified as cosmetics rather than medications. Essential oils extracted from three

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common plants in Lebanese traditional medicine, viz., Salvia aurea L., Salvia judaica Boiss., and Salvia viscosa Jacq., were examined for their possible anticancer efficacy. In vitro and in vivo studies revealed that all three oils have antitumor efficacy with minimal toxicity (Russo et al., 2016). Although higher concentrations of essential oils have been linked to detrimental alterations in the body (Maistro et al., 2010). Salvia sclarea essential oil is considered to be safe and there are no adverse effects reported so far (Mahboubi, 2020). Pusˇka´rova´ et al. (2017) investigated cytotoxic impact of various essential oils, including clary sage, on HEL 12469 human embryonic lung cells and found that it had not caused DNA damage after 24 h in vitro.

19.8 Trade, storage, stability, and transport Salvia sclarea holds significant position in world trade. It has a substantial commercial value in the perfume and cosmetics industries.

19.9 Conclusion Clary sage oil is an aromatic herb with wider applications across pharmaceutical, food, cosmetics, and agriculture sectors. It is a well know herb in traditional folk medicine. Recently it has gained popularity in aromatherapy, food packaging, wound dressings and as semiochemicals in agriculture. Essential oil composition depends on a variety of factors viz. plant variety, environmental conditions, fertilizer use, geographical or ecological conditions, method of extraction, harvesting time, and so on. Clary sage essential oil possesses several biological properties, for example, antimicrobial, antianxiolytic, antioxidant, cytotoxic, antiinflammatory, antidiabetic, antistressor role in women menstrual health. Recently, essential oils have gained importance in being used as bioinsecticide. Several reports have demonstrated the insecticidal effect of clary sage essential oil against plant pests. There is increasing trend in incorporation of essential oils in herbal cosmetics due to its nontoxic and nonirritant nature. Due to the presence of antimicrobial, antiinflammatory, antioxidant activities, clary sage oil can be incorporated in herbal medicine preparations. Another exciting use of essential oil is seen in wound dressings and food packaging due to its biodegradable nature. Essential oils in general are considered safe to use, only the appropriate concentration should be kept in mind.

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Yaseen, M., Kumar, B., Ram, D., Singh, M., Anand, S., Yadav, H.K., Samad, A., 2015. Agro morphological, chemical and genetic variability studies for yield assessment in clary sage (Salvia sclarea L.). Ind. Crop Prod. 77, 640–647. Yoon, J., Tak, J., 2018. Toxicity and repellent activity of plant essential oils and their blending effects against two spotted spider mites, Tetranychus urticae Koch. Korean J. Appl. Entomol. 57, 199–207. Yousefzadi, M., Sonboli, A., Karimic, F., Ebrahimi, S.N., Asghari, B., Zeinalia, A., 2007. Antimicrobial activity of some Salvia species essential oils from Iran. Z. Naturforsch. C J. Biosci. 62, 514–518. Zhang, X., Gao, H., Zhang, L., Liu, D., Ye, X., 2012. Extraction of essential oil from discarded tobacco leaves by solvent extraction and steam distillation, and identification of its chemical composition. Ind. Crop Prod. 39, 162–169. Zhang, W., Ronca, S., Mele, E., 2017a. Electrospun nanofibres containing antimicrobial plant extracts. Nanomaterials (Basel, Switzerland) 7, 42. Zhang, W., Huang, C., Kusmartseva, O., Thomas, N.L., Mele, E., 2017b. Electrospinning of polylactic acid fibres containing tea tree and manuka oil. React. Funct. Polym. 117, 106–111. Zutic, I., Nitzan, N., Chaimovitsh, D., Schechter, A., Dudai, N., 2016. Geographical location is a key component to effective breeding of clary sage (Salvia sclarea) for essential oil composition. Israel J. Plant Sci. 63, 134–141.

C H A P T E R

20 Tea tree essential oil Iahtisham-Ul-Haqa, Sipper Khanb, Muhammad Sohailc, Muhammad Jawad Iqbald, Kanza Aziz Awane, and Gulzar Ahmad Nayikf a

Kauser Abdulla Malik School of Life Sciences, Forman Christian College (A Chartered University), Lahore, Pakistan bUniversity of Hohenheim, Institute of Agricultural Engineering, Tropics and Subtropics Group, Stuttgart, Germany cResearch and Development Section, Punjab Food Authority, Government of the Punjab, Lahore, Pakistan dDepartment of Food Science and Technology, Minhaj University, Lahore, Pakistan eDepartment of Food Science and Technology, University of Central Punjab, Lahore, Pakistan fDepartment of Food Science & Technology, Government Degree College Shopian, Srinagar, Jammu & Kashmir, India

20.1 Introduction The recent era has witnessed a huge drift toward natural products for their pharmacological, cosmetic, agrofood, and other applications. Nowadays, the consumers are more concerned about the safety of the product ingredients, so this transition is being attributed to safer nature of natural additives compared to their synthetic counterparts. The demand for natural products has encouraged the research and development, to find natural solutions for numerous applications. In this context, the essential oils (EOs) have grabbed major attention due to their wide spectrum of application in pharmaceutics, cosmetics, food, biomedical, veterinary and agricultural products (Yadav et al., 2017). Alongside, these oils also have great potential to treat various diseases as well (Nazzaro et al., 2013). Tea tree is a plant scientifically known as Melaleuca alternifolia belonging to the Myrtaceae family. One of the key products obtained from tea tree is the EO, more commonly known as TTO. This oil is primarily extracted from the leaves of the tea tree. Physically, the oil could be colorless to pale yellow in color, possessing numerous properties for medicinal, cosmetic, and agrochemical applications. The first reports on antiseptic properties of the TTO were published in the 1920s by Penfold and Grant where it was found to be 11 times more effective than phenol (Larson and Jacob, 2012). It has been reported that TTO contains more than 100 Essential Oils https://doi.org/10.1016/B978-0-323-91740-7.00017-7

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bioactive compounds capable of delivering various effects such as antioxidant, antiviral, antibiotic and antiseptic agent (Yadav et al., 2017). The major compounds present in TTO are monoterpenes, sesquiterpenes and their related alcohols (Nogueira et al., 2014). The detailed discussion on the phytochemical compounds is included in the subsequent sections. The EOs are produced by plants to prevent themselves from the invasion by herbivorous animals and to attract the insects for pollination. Although, TTO has various benefits and has find its place in wide applications in different products, the major safety concern related to it is the allergic reactions upon topical application. Furthermore, it is found toxic when consumed orally (Crawford et al., 2004; Larson and Jacob, 2012). The detailed commentary on its safety aspects can be found in related section in this chapter. Hence, its use in the products should be made keeping in mind the intended use and targeted population. In this context, this chapter describes the phytochemistry, extraction methods, characterization, applications as agrofood, cosmetic and pharmaceutical agent, and safety of the TTO.

20.2 Phytochemistry of tea tree EO Native to Australia and Oceania, tea tree plants belong to Myrtaceae family. These plants are utilized in the preparation of various traditional medicines used by the Aborigine people owing to their wide spectrum of antimicrobial properties. Other medicinal plants of the same family include M. linariifolia, M. dissitiflora, etc. TTO, extracted from M. alternifolia exhibits the longest history of medicinal usage. TTO constitutes mainly 80%–90% of monoterpenes including 1,8-cineol (traces-10%), limonene (0.5%–1.5%), sabinene (traces-3.5%), p-cymene (0.5%–8%), α-pinene (1%–4%), terpinolene (1.5%–5%), terpinene-4-ol (35%–48%), α-terpinene (6%–12%), γ-terpinene (14%–28%), aromadendrene (0.25%–3%), ledene (0.1%–3%), globulol (traces-1%), and viridiflorol (traces-1%) (Nazzaro et al., 2013). Some of the chemical constituents from tea tree are shown in Fig. 20.1.

FIG. 20.1

Phytochemical constituents in TTO.

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Recent research identified three new compounds, named as melaleucins A-C (1–3), and seven other compounds namely methyl eugenol, 3,4,5-trimethoxy-benzoic acid methyl ester, 30 methoxymiliumollin, vomifoliol, betulinic acid, β-sitistenone, and β-sitosterol from both M. alternifolia and M. linariifolia species (Kong et al., 2019). Other phytochemical properties include the functionally active role of terpinene-4-ol on Na+/glucose cotransporters, in the ileum to transport glucose into the blood, but this action can be inhibited by (+)-catechin and other tea derivatives. Similarly, 1,8-cineole is used for antiinflammatory activities owing to its role in the reduction of neural excitability. It also acts as an antinociceptive agent and exhibits myorelaxant in guinea pigs with a higher probability of inducing similar results among humans when are accompanied by other terpenoids (Nazzaro et al., 2013). A detailed description of the TTO constituents is given in Table 20.1. TABLE 20.1

Chemical constituents in TTO. Concentration (%)

Chemical formula

p-Cymene

0.5–8

C10H14

D-Limonene

0.5–1.5

C10H16

Sabinene

Trace-3.5

Terpinolene

1.5–5

Components

Chemical structure

Continued

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TABLE 20.1 Chemical constituents in TTO—cont’d Components

Chemical structure

Concentration (%)

α-Terpinene

5–13

α-Pinene

1–6

γ-Terpinene

10–28

1,8-Cineole (eucalyptol)

Trace-15

Terpinen-4-ol

30–48

Chemical formula

C10H18O

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TABLE 20.1

Chemical constituents in TTO—cont’d

Components

Chemical structure

Concentration (%)

α-Terpineol

1.5–8

Aromadendrene

Trace-3

Ledene (syn. Viridiflorene)

Trace-3

Globulol

Trace-1

Viridiflorol

Trace-1

Chemical formula

C15H24

C15H26O

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M. alternifolia is voluminously researched for the bioactive potential of its constituents. Some studies were seen against Gram-positive Bacterium Staphylococcus aureus with minimal inhibitory concentration (MIC) to be 0.12–1 mg/mL, Gram-negative bacterium E. coli has MIC of 0.12–1.5 mg/mL, A. fumigatus 1.78 mg/mL, and C. albicans 0.05–0.5 mg/mL but more research is needed for clearer evidence confirming its antimicrobial potential. Pharmacokinetic studies reveal about its absorption that TTO when applied to the human skin impacts its rectitude along with the benzoic acid perforation in percutaneous layer with dose dependency. TTO components inside a small concentration of 1.5% and 3% after 20% concentrated application of TTO penetrate the human epidermis layer. Similarly, research also highlights that approximately 98% of the oil evaporates after the first few hours of application (Nielsen, 2006; Nielsen and Nielsen, 2006). Furthermore, the distribution mechanism was explained where terpinene-4-ol, methyl eugenol, 30 methoxymiliumollin, vomifoliol, betulinic acid, β-sitostenone, and β-sitosterol are distributed to the human liver for metabolism after the application in the first couple of hours (Kasujja, 2021). The metabolism-based studies indicate that the microsomes contain CYP2A6, which is a principal enzyme employed in the oxidation of ()- terpinene-4-ol in the liver of humans (Fig. 20.2). This oxidation is inhibited by (+)-menthofuran. There are currently no reports on the biotransformation of ()- terpinene-4-ol by the human liver microsomes. Several monoterpenes (1,4-cineole, 1,8-cineole, menthols, limonenes) are metabolized by the cytochrome P450 enzymes in the microsomes of the liver in humans’ liver as shown in Fig. 20.3. Finally, like most phytochemicals of the plant source, terpinene-4-ol, methyl eugenol, 30 methoxymiliumollin, vomifoliol, betulinic acid, β-sitostenone, and β-sitosterol are excreted via urine assimilated by the microbes or the host tissues (Fardet et al., 2008; Kasujja, 2021).

FIG. 20.2

Oxidation and hydrolysis of α-terpinene.

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FIG. 20.3 Metabolic interconversion of limonene, a-terpineol and 1,8 cineole.

20.3 Extraction of tea tree EO Initially, TTO on extrication from Melaleuca alternifolia is then followed by commercial extraction. The commercial TTO extraction and its industrial use originated mainly when the Australian chemist Arthur Penfold, a chemist in the 1920s first scrutinized the therapeutic and business potential of various EOs (Mackenzie, 2006). He observed that TTO possesses promising antiseptic effect. As per the Allied Market Research, “the global TTO market size was valued at $38.8 million in 2017 and is projected to reach $59.5 million by 2025.” There are many conventional and modern extraction techniques being commercially utilized fractionation of oil from the plants. These techniques entail hydro-distillation, solvent extraction, and supercritical fluid extraction however most of the EOs are produced commercially using steam distillation process. The extracted oil by steam distillation was reported to be 93% whereas the remaining 7% was contributed the other methods (Masango, 2001). Therefore, we will mainly focus on steam distillation process in this chapter.

20.3.1 Steam distillation extraction Steam distillation is one of the oldest and the most extensively applied method for commercial extraction of EO from different plant matrices including tea tree. The method is greatly accepted by all the stockholders due to simplicity in its operations, readily available extraction medium (steam) at cheap price and its reusability throughout the process, good extraction yields and low operational cost. Further, the oil obtained through steam extraction also exhibits minimum changes in the oil composition. All these factors make this technique popular for commercial application (Huynh et al., 2012). 20.3.1.1 Pretreatment of raw material for steam distillation During steam distillation it is difficult for dry steam to penetrate the dry cell membrane and thus extraction yield of EO is decreased. However, the penetration and dissolving power of dry heat can be improved by using different pretreatments. For instance, the target plant material can be milled prior to steam distillation. This process will breakdown the cell walls and will liberate the EO making its recovery easy. Soaking in hot water is another method for

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improving the efficiency of steam distillation. Naturally, plant cell membranes are impermeable to EOs. However, soaking in water turns the plant cell membrane into permeable. Also, hot water causes liquefaction of EO in the water inside the glands. During this process, hot water forms a solution with EO inside the membrane. This solution permeates plants cell membranes though osmosis and go out of the membrane. This oil is then readily available for steam distillation. In addition to improving extraction yields, these pretreatments also decrease the extraction time (Ranjitha and Vijiyalakshmi, 2014).

20.3.2 Steam distillation process The apparatus used for steam distillation of plant material consists of following key components (Fig. 20.4) 1. 2. 3. 4.

Steam source (boiler) Distillation vessel Condenser Separator or decanter

TTO is produced both from the terminal branches and leaves of tea tree. The raw material is first cleaned to remove any extraneous matter. To improve the extraction yield, pretreatment of the raw material is done. The final raw material is packed inside a distillation vessel. Steam is produced by an external boiler and this steam is supplied to the distillation vessel where it interacts with the plant material. The major operational parameters include steam flow rate, temperature and pressure of the distillation vessel and selection of optimum conditions is necessary to produce good quality EO. At higher temperatures, hydrolysis process occurs in which the esters (components of EOs) react with water to produce alcohols and acids. Increased amount of water will increase this process and will lead to the formation of more acids and alcohols. Therefore, it is necessary to choose steam flow rate and distillation vessel temperature very carefully to avoid hydrolysis of EO components. Next, in the distillation vessel, the steam penetrates in the cells of plan material and dissolve the EOs in it. This steam is then passed

FIG. 20.4

Steam distillation process.

20.3 Extraction of tea tree EO

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through a condenser where it is converted into the liquid form. This liquid from condenser includes water and EO. It is then collected in a separator where this mixture will form two liquid phases due to difference in the specific gravity of oil and water. The EO will form upper layer and will be collected for further processing (Masango, 2001). Studies have reported that current yield of TTO using stream distillation process is about 1%–2% as a basis of wet material weight (Carson et al., 2006). According to Swami et al. (2008), the steam distillation process provides different advantages some of which are enlisted below: • • • •

This method is very cheap and easy to perform This method uses water as extraction medium which is readily available The operation requires simple equipment and less operational steps Steam penetrates cell metrics and ensure even heat transfer

There are certain pitfalls associated to the steam distillation process as well that may include one or more of the following: • Complete extraction of EO is not possible • Some components of EO (esters) are sensitive to water and high temperature. They hydrolyze to form acids and alcohols. Whereas other components like monoterpene hydrocarbons and aldehydes are prone to polymerization • Steam distillation process requires longer period for extraction • Fuel consumption is high during this process • This process produces low quality oil which need further processing (e.g., vacuum distillation) for making it suitable for commercial applications

20.3.3 Modifications in steam distillation process As discussed above, simple steam distillation exhibits many disadvantages. Many studies have focused on the modification of steam distillation process to increase the process efficiency, cut down the operational cost, and improved the extraction time and the quality of extracted oil. Microwave steam distillation (MSD) is an excellent example of such modification. All the apparatus required in this technique is same as conventional steam distillation except a microwave cavity which encloses the distillation vessel or cartridge. The process diagram is shown (Fig. 20.5). The microwave cavity has a source of microwave which is used to heat the cartridge containing plant material for extraction purpose. As soon as the steam start passing through the extraction vessel or cartridge, it is subjected to microwave heating. Microwaves rupture the cell membrane, glands, and cell receptacles, liberating the EO from plant cells. Steam also has similar effect on the plant matrices therefore the extraction process is accelerated. Steam pass through the raw material (stems, leaves etc.) and carry the EO with it toward the condenser. Like conventional steam distillation, the water and oil infused solvent in the combined form of separator where EO is siphoned from the solvent later for further processing. Studies have reported that steam distillation using microwaves is a rapid process comparatively to the other methods. In a study, same EO yield was obtained within 6 min using microwaves compared to the conventional method where it took 30 min to extract same

488

FIG. 20.5

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Microwave assisted steam distillation of TTO.

quantity of EO. This time reduction cut down the overall energy requirement of the process and thus provide same yield of EO at low cost. Moreover, the quality of oil obtained through this process is also improved (Sahraoui et al., 2008).

20.3.4 Other extraction methods Conventional steam distillation offers many benefits in terms of ease and cost of operation; however, few components went through deterioration owing to high heat-based thermal effect exposed during direct contact with the plant material. This thermal degradation significantly degrades certain percentage of EO. Moreover, the recovered oil is not superior in quality. Therefore, many techniques are employed for the segregation of thermo-labile components by employing low temperature conditions. Solvent extraction is an extraction technique for EOs which use ether, ethanol, n-hexane etc. with better recovery rate and optimum quality. Initially the raw material is placed inside an extraction vessel and desired solvent is added. The temperature and time are two main variables which play important role in the extraction. Additionally, the contents of extraction vessel can be shaken to increase the contact area of solvent and plant material, thereby improving the recovery rate of desired component. Overall dynamics also plays a significant role. Solvent helps dissolves the EO and the mixture of solvent and EO is separated from the plant material. This volatile solvent evaporates later by low heat treatment, leaving the pure EO behind (Benedict, 2009). These solvents utilized in this method are costly, flammable and often toxic resulting in environmentally toxic when disposed. Moreover, the residues of solvent are sometimes present in the yielded EOs and are difficult to remove. To address these issues, other modern techniques have been developed. Supercritical fluid extraction (SFE) is one such technique which is environment friendly and the EOs produced by using this technique are highly pure.

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SFE utilize supercritical fluid as extraction medium (mostly CO2). When any gas is above its critical temperature and pressure, it is converted into supercritical fluid. CO2 in its supercritical phase possess properties of both liquid and gas. The extraction efficiency is greatly enhanced due to low viscosity and high density of supercritical CO2. Lower viscosity enables the easy flow penetrating the raw material while the higher densities result in enhanced power of dissolution. In this extraction technique, the plant material is packed inside an extraction vessel and supercritical CO2 is injected in the vessel where temperature and pressure are adjusted according to the component to be extracted. Stay time is given for maximum extraction of desired component (EO in this case) and the extract is obtained through a valve. CO2 is converted into gas at room temperature and pressure, leaving pure extract in the collection tube. This CO2 gas can be recovered and used again which reduces the operational cost significantly (Sohail et al., 2017).

20.4 Applications of tea tree essential oils TTO has proven to have considerable potential as an antimicrobial, antioxidant agent along with enhancing food safety increasing the overall quality of the shelf life. Among the other attributes, TTO also exhibited antiparasitic and free radical scavenging properties with a major concentration of terpinene-4-ol, γ-terpinene, p-cymene, α-terpinene, 1,8-cineole, α-terpineol, and α-pinene resulting in strong antifungal, cytotoxic and immunomodulatory properties (Bhavaniramya et al., 2019; Ramage et al., 2012). Other therapeutic properties of TTO include antiinflammatory properties, antimicrobial (against Staphylococcus aureus), oral bacteria, herpes, and influenza viruses, against fungi, and some azole-resistant yeasts (Ramage et al., 2012). Some main pharmacological applications of TTO are summarized below.

20.4.1 Pharmacological applications 20.4.1.1 Antimicrobial applications The immense potential of TTO has been observed in the treatment of different dermatological disorders owing to the antimicrobial contributions against many microorganisms. It contains an array of monoterpenes, sesquiterpenes, and their alcoholic derivatives therefore with a minimal tendency of developing microbial resistance, its application has been reported as an analgesic, antiviral, antibacterial, antifungal, and antiprotozoal agent. Its effective contribution in overcoming the conventional drug-based resistance development by different bacteria was also reported. However, for effective delivery with exact formulations, volatility, temperature, air, and having light sensitivity, along with hydrophobicity specifications are needed to be precisely controlled. The antimicrobial action is observed with a resulting loss of membrane integrity resulting in preventing the respiratory function in microbes. TTO is also known to inhibit specific respiratory enzymes along with altering the membrane structure, therefore, increasing the uptake of the nucleic acid and leaking the potassium ions results in causing the disruption in E. coli and S. aureus. Further research is also supporting the role of TTO in preventing antibiotic resistance and susceptibility (Puva
ca et al., 2018). Melissococcus plutonius and Paenibacillus larvae are considered the primary bacterial pathogens

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accountable for both the European and American foulbrood diseases, respectively. Owing to the ineffective and less efficacy of the antibiotics employed, nanotechnological research is being used to develop new therapeutic strategies for their slow, gradual, controlled release, enhanced bioavailability, and fewer side effects as compared to their counterparts. In vitro antimicrobial activity of TTO nanoparticles was evaluated against Paenibacillus species including P. larvae and M. plutinus strains, with MIC 0.18%–6.25% for regular while nanoparticle MIC included 0.01%–0.93%, without any toxicity even after 7 observation days (Santos et al., 2014). Remarkable antimicrobial activity was also reported against pathogenic bacteria including S. aureus, S. pyogenes, P. aeruginosa, P. vulgaris, A. hydrophila, E. coli, S. pneumoniae, B. subtilis, K. pneumonia, and S. agalactiae. After 24 h of incubation, 96.94% inhibition against E. coli while 100% rate of inhibition was found during research study against seven of the bacteria (Mumu and Hossain, 2018). Similarly, in fungus species also the modifications in fungal membranes result in triggering the antifungal mechanisms (Bilal et al., 2020). Some antimicrobial functions are summarized in Table 20.2. TABLE 20.2 Summary of antimicrobial functions of TTO. Functional role of TTO

Microbial name

Mechanism of action

References

Antibacterial

Streptococcus aureus

Prevention of respiration along with potassium ion leakage resulting in increased sensitization to NaCl and modifications in the morphology

Cox et al. (2000), Hada et al. (2003), Carson et al. (2002), Reichling et al. (2002), Yadav et al. (2017), Yadav et al. (2017)

Escherichia coli

Disturbance of K+ homeostasis, structural disruption, and glucosedependent respiration. Bacterial membranes changes in both the structure and functions along with lysin interference

Cox et al. (1998), Gustafson et al. (1998), Yadav et al. (2017)

Pseudomonas aeruginosa

High tolerance to the TTO concentration was observed in the outer membrane integrity of bacteria also

Longbottom et al. (2004), Mann et al. (2000)

Candida albicans

The fluidity of the membrane and the permeation gets altered. Reversible inhibition is also observed in the microbe’s morphogenesis

Hammer et al. (2000), Hammer et al. (2004), Yadav et al. (2017)

Candida glabrata

Changed membrane’s permeability

Hammer et al. (2000), Yadav et al. (2017)

Saccharomyces cerevisiae

Prevented the glucose-induced medium acidification owing to the mitochondrial membrane, plasmabased modifications

Cotmore et al. (1979), Yadav et al. (2017)

Influenza A/PR/8 virus subtype H1N1

Viral uncoating was prevented owing to intralysosomal acidification

Garozzo et al. (2011), Yadav et al. (2017)

Antifungal

Antiviral

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Antifungal properties of TTO are associated with modifying the fungal membranes mainly while the antiviral activity reported in Tobacco mosaic virus for the first time indicated both TTO’s potency against enveloped and nonenveloped viruses. Antifungal properties were also evident against Botrytis cinerea by disrupting mitochondrial morphology and likewise prohibiting its normal functioning (Li et al., 2017; Yue et al., 2020). 20.4.1.2 Antiinflammatory properties The combined impact of antiinflammatory and antimicrobial property of TTO is utilized against the inflamed acne lesions (Bassett et al., 1990; Esmael et al., 2020), gingival index (Soukoulis and Hirsch, 2004), papillary bleeding index score where it is applied topically and is responsible for improving the lesions re-epithelialization in Herpes liabilis patients (Carson et al., 2001). Terpinen-4-ol is considered accountable for preventing this inflammation by vasodilation and plasma extravasation. TTO suppressed the inflammatory mediator production, that is a lipopolysaccharide stimulating human macrophages by interfering with the nuclear factor NF-kB, p38, or the mitogen-activated protein kinase pathways (Nogueira et al., 2014). In research conducted, Chin and colleagues researched the wound healing property of TTO where it exhibited the cooling property on the patient’s skin (Chin and Cordell, 2013). Another study reported a reduction in wound area where the administration of hydrogel-TTO nanocapsules caused a decrease in inflammation (Flores et al., 2015). Based on hydrocarbon structure and lipophilic nature, this hydrocarbon partition is embedded into the biological membrane resulting in disturbing the main functions (Sikkema et al., 1995). Similarly, the liposomal systems permeabilize TTO as per the evidence of previously conducted research (Cox et al., 2000). 20.4.1.3 Antioxidant Bioactive constituents extracted from EOs are gaining immense importance owing to their functional spectrum as antimicrobial, anticancer, antiinflammatory, and antioxidants. With their increased use in different therapies, pharmacological usage, and medicinal applications enhanced research is being carried out to exhibit the dietary phenolic content and antioxidant potential of TTO. This antioxidant potential is visible in the reduction of diseases involving DNA damage, mutagenesis, carcinogenesis, prevention of pathogenic bacteria’s growth, and the prevention of free radical propagation (Puva
ca et al., 2018; Imane et al., 2020). In vitro analysis previously indicated strong individual component’s antioxidant activity identified by C18-HPLC and GC–MS (Kim et al., 2004). These EOs are now isolated to exploit the antioxidant and antiinflammatory properties effectively for improving the overall food and feed quality in the recent researches (Dzˇinic et al., 2015; Spasevski et al., 2018; Miguel, 2010). 20.4.1.4 Anticancer The anticancer potential of TTO has been researched in different cases (Bozzuto et al., 2011; Pazyar et al., 2013; Angelini et al., 2018; Greay and Hammer, 2015). In vitro cytotoxicity studies conducted on 14 cancers and many types of nonmalignant cell lines were carried out. These non -malignant cell lines included cervical cancer (HeLa), acute lymphoblastic leukemia (MOLT-4), erythromyeloblastoid leukemia (K562), and B cell taken from acute myeloid leukemia (CTVR1) patient’s bone marrow (epithelial cells, fibroblast). Results indicated that TTO exhibited IC50 on these cell growth ranging from 0.002%–0.27% (v/v) (Angelini et al., 2018). Similarly, another

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study revealed its role in the impairment of human melanoma M14 wild-type cells, which was far more effective on their resistant variants (M14 adriamycin-resistant cells) exhibiting resistance to apoptosis phenomena dependent on caspase, exercised by P-glycoprotein-positive tumor cells. These resistance cells and TTO reactions were linked to the plasma membrane composed of mainly lipid-based integrities (Angelini et al., 2018). Another study observed the cytotoxic role of TTO in murine mesothelioma (AE17) and melanoma (B16) cell lines where terpinene-4-ol induced the primary necrotic cell death with the low level of apoptosis and cell cycle arrest. This bioactive constituent interrupts the migration process and the onslaught of both the drug-sensitive and drug-resistant melanoma cells (Ireland et al., 2012). Further research indicates that this bioactive constituent is effectively utilized for apoptosis induction through the intrinsic mitochondrial pathway in the nonsmall cells of lung cancer lines (NSCLC), A549, and CL1–0. Furthermore, terpinene-4ol reduced the concentration of apoptosis inhibitor proteins (AIPs), activated caspase 3 and 9, and cleaved poly (ADP-ribose) polymerase (PARP) (Angelini et al., 2018). The research was conducted on both mouse and human breast cancer cell line MCF-7 and 4T1 respectively for understanding the mechanism of TTO in vitro antitumor activity. High TTO concentration resulted in lowering the cell endurance and augmentation of cells in MCF-7 and 4T1 cell lines ( 600 μg/mL). At 300 μg/mL concentration level, it also increased the MCF-7 cell number in the early apoptosis stage, but then decreased the cell growth at the S phase of the cell cycle and increased the BAX/BCL-2 genes ratio, indicating topical treatments availability against locally advanced breast cancer (LABC) (Assmann et al., 2018). Similarly, statistically significant results were obtained when the research was conducted to check the anticancer potential of TTO against the leukemia cancer K562 cell line after 48 h of incubation period at an IC50 value of 3.125 μg/mL (Byahatti et al., 2018a). Likewise, on cell line of colon cancer (HT29), laryngeal cancer cell line (Hep2), and breast cancer cell line (MDA MB) also exhibited similar findings highlighting the further need for clinical trials to authenticate the research findings (Byahatti et al., 2019, 2018c,b). Moreover, on the necrosis and cell cycle arrest initiation in murine cancer cell lines, statistically significant results were obtained in previous research, with both dose and timedependent conditions. The efficacy of TTO was however observed to be less in the nontumor fibroblast cells. The inhibitory effect was elicited at G1 cell-cycle arrest by both TTO and terpinene-4-ol highlighting its impact against proliferation against the cancer cells (Greay et al., 2010). 20.4.1.5 Acaridical properties Acaridical properties of TTO are proven in different research studies. Ticks, specifically lxodes ricinus are considered the most effective vector of pathogenic agents for the transmission of Lyme disease, human granulocytic ehrlichiosis, and some pathologically similar Mediterranean spotted fever. Research studies indicate the detrimental usage of synthetic acaridical agents employed on both the animals and the environment. Therefore, alternate usage of materials effective for controlling the tick population is needed. EOs of Neem and Ocimum suave have supported this role against the larvae of Amblyomma variegatum and Hyalomma anatolicum excavatum (all stages) and Rhipicephalus appendiculatus (AbdelShafy and Zayed, 2002). The impact of TTO was also tested against nymphs of I. ricinus. An 8 mL dosage of TTO was considered effective in inhibiting 70% of ticks while >80% results

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were obtained on using 10 mL of the dosage. This effect is also impacted by the time given for nymph’s exposure to the TTO. This can significantly impact the large-scale economic loss in cattle reported due to ticks, however, more research is needed to establish the appropriate designed controlled release of formulations to extend the repellence against the ticks responsible for different diseases reported (Puva
ca et al., 2018). 20.4.1.6 Topical, herbal and therapeutic applications TTO is added in different products with varying concentrations as per the topical formulations prepared after thorough research. In moisturizers, it is added approximately 1.25%. Similarly, 1.25% in the body lotions, 0.1% in the face cleaning washes, 0.7% in the hand washes, 2% in soaps, 2% in the foot sprays, 2% in the shaving powders, and 2% in the post waxing treatments have been used in different topical products. A yeast-like fungus, Malassezia is responsible for dandruff that leads to extreme dermal cell growth which upon dying result in becoming dandruff on the scalp. With the antifungal properties of TTO, it can be combated with 5% TTO’s presence in shampoo (Yadav et al., 2017). Generally, caries in teeth is caused by Streptococcus mutans and Lactobacillus rhamnosus. TTO in the gel is reported to be effective against these dental caries (Pithon, 2014). However, swelling of gums/gingival infections employs both antiinflammatory and antiseptic properties of TTO and Neem-based toothpaste (Yadav et al., 2017). Acne vulgaris is a multifactorial disorder of the pilosebaceous glands resulting in unbalancing the hormones, in the hyper pigmenting follicles, causing bacterial infections and making the immune system hypersensitive along with genetic influence from 11 to 30 years of age (Goulden et al., 1999; Burkhart and Burkhart, 2007). It is also associated with inflamed red papules and pastules (Toyoda et al., 1995), caused mainly by gram-positive bacteria Propionibacterium acnes (Tanghetti and Popp, 2009). Acne is also reported to further trigger psychosomatic influence in patients causing depression, frustration, and distress among the patients. Therefore, TTO is considered effective after benzoyl peroxide with evident antiinflammatory and antibacterial effects, especially with its fewer chances of developing any antibiotic resistance (Bassett et al., 1990; Esmael et al., 2020; Kallis et al., 2018). Seborrheic dermatitis is also a fungal skin infection caused by Malassezia furfur. Approximately 5% TTO is considered useful in treatment of fungal infections of skin against seborrheic dermatitis (Pazyar et al., 2013). Similarly, onychomycosis is a fungal infection of the nail resulting in discoloration, thickening, and finally detachment of nails. It is mainly caused by dermatophytes, genus Trichophyton. The onychomycosis is classified into three types depending on the invasion route, distal subungual (common), white superficial, and proximal subungual onychomycosis (mainly caused by T. rubrum), against which TTO had been effective in nanostructural delivery systems (Elewski, 1998; Summerbell, 1997; Flores et al., 2013). Current research indicates that Trichophyton lack of growth was observed at an increased concentration >0.04% of the TTO, with complete prevention of its growth observed at 0.07%. This treatment is considered not only effective in the in vitro growth of the fungus but also less harmful as compared to the existing onychomycosis treatments (Marcos-Tejedor et al., 2021). The Tinea pedis/athlete’s foot, mainly caused by T. rubrum fungus. The clinical treatment of this infection compared administration of 1% tolnaftate cream with TTO cream. Another research highlighted that 50% TTO solution was efficacious against the treating 64% trial patients suffering from athlete’s foot (Thosar et al., 2013).

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Vaginal flora is known to be altered by numerous factors including consumption of antibiotics and oral contraceptives, adopting dietary changes, and developing infectious diseases. Overgrowth of candida spp. Is primarily responsible for the propagation of vaginal candiasis. TTO is considered effective against both gram positive (+ve) and negative (ve) bacteria. Investigative trials were therefore conducted on 130 participants with various vaginal conditions and others with 20 participants with conclusive no irritability recorded in both the trials on the usage of intravaginal TTO usage (Pena, 1962). In vitro studies indicated the effectivity of TTO products with low concentrations (0.5% v/v). On a commercial scale, douches, gels, and pessaries of TTO are also being sold (Hammer et al., 1998). The effectivity of TTO was also reported recently to be effective among pregnant women, having high vulnerability to vaginal candidiasis especially during the third trimester (Dahham et al., 2019).

20.4.2 Agrofood applications Traditional usage of TTO is observed in cosmetic, aromatherapies, and herbal medicine production. The application spectrum further expanded to treating inflammation, colds, headaches, coughs, acne treatment to antitumor properties observed on breast cancer cells without any cytotoxicity. Antifungal properties were also exploited against different infections. However, antimycotic modes of utility in the food industry are still widely underresearched. TTO components (terpene-4-ol, 3-Carene, α-terpineol) have been considered significantly efficacious against the Aspergillus niger species, therefore holding potential for synthetic preservatives. Terpene-4-ol and α-terpineol exhibited effectiveness against mycelium and spore growth and germination process. These components destroyed the cytomembrane permeability and interfered with the hyphae and spore’s morphology, while 3-Carene showed a less inhibitory effect. The above two constituents also combated against black mold disease in post-harvest grapes that generally leads to immense economical reduction in the grape and wine industry (An et al., 2019). The antimicrobial potential of TTO is observed against E. coli and L. monocytogenes. This mechanism of altering the permeability and integrity of the bacterial cell membrane is effective in disrupting the microbial cell with specifically lower minimum inhibitory concentration value and larger inhibition zones. A trial conducted in cucumber juice was evaluated by the time-kill assay at both the room and refrigeration temperature, demonstrated the preservative potential of the TTO against food-borne pathogens (Shi et al., 2018).

20.4.3 Nonfood applications Nonfood applications of TTO include primarily aromatherapy. EOs with their unique aroma and complex chemical properties can be inhaled, digested, topically applied, and eliminated from the body through respiration and urination (Winkelman, 2018; C ¸ alis¸ kan and € _ 2018). This wide spectrum of TTO resulted in enhancing its usage in both food Ozfenerc I, and nonfood industries. Escalating certification in herbal and medicinal usage has further en€ hanced the growth in their application in the nursing industry (Ayse Ozkaraman et al., 2018). In research conducted on patients getting chemotherapy, TTO indicated no effect on the state € and anxiety levels but significantly enhanced the sleep quality (Ozkaraman et al., 2018).

20.5 Safety concerns

495

Additionally, another study revealed the combined effectiveness of TTO and eucalyptus oil aromatherapy in accelerating the healing time among toddlers suffering from the common cold (Maftuchah et al., 2020). Similarly, other nonfood applications of TTO are observed in the preparation of biopolymer grafted with antimicrobial properties, TTO accompanied with rice bran was employed for sustained release in polyethylene films. These packaging materials exhibit immense potential for both food packaging and biomedical purposes (El-Wakil et al., 2020). Other nonfood applications include the potential of TTO as a nanoemulsion paired with calcium chloride (CaCl2) and chitosan (low molecular weight), where it synergistically improved the overall quality and shelf life of the fresh-cut red bell peppers for up to 18 days (Sathiyaseelan et al., 2021). The antimicrobial especially the antiviral potential of TTO is effective in its role as a spray-on surface disinfectant with masks and personal protective equipment (PPE) during the COVID situation (Celina et al., 2020). Previous studies have also explained its potential as a sanitizer for food-based contact surfaces (Falco´ et al., 2019). Another nonfood application included the usage of TTO shampoo eyelid scrubs for elderly patients suffering from Meibomian gland dysfunction or evaporative dry eye (HernandezMartinez et al., 2018). These applications of TTO provide a summarized overview of its existing applications along with mentioning the areas needing further research to enhance its commercial usage. Effectivity of TTO has also been observed as a safe mosquito repellent. Previous ethnobotanical survey-based research indicates its usage for repelling insects especially mosquitos and other biting insects (Callander and James, 2012; Maia and Moore, 2011; Rehman et al., 2014). TTO has also shown strong toxic and repelling effect against the parasites of arthropods. The active principle is terpinene-4-ol (30%–48%) with the main factors including dosage, species assayed, toxicity methods and the targeted characteristics (Fonseca-Santos et al., 2019).

20.5 Safety concerns For application of nutraceutical or herbal supplements to human use is always subjected to their safety and toxicity profiles (Wei et al., 2021). In this respect, the TTO is no exception to the phenomena that it may cause toxicity or allergic reactions. It has been reported that TTO acquires toxic or allergic effects on humans via ingestion or dermal exposures to higher concentrations of the oil. It is further seen that the adverse reactions of TTO are subjected to concentration and exposed dosage of the compound. Since, the toxicity of TTO is dose-dependent hence, its negative impacts may be avoided by using lower concentrations of the oil in the products or therapeutic regimes. However, the allergic reactions may arise even at lower concentrations so the individuals sensitive to TTO or its products must avoid their contact to the suspected products. Majorly, oxidation products of TTO are responsible for causing allergic reactions in people sensitive to such compounds (Hammer et al., 2006). In a study, the irritation potential of undiluted TTO was more pronounced as compared to diluted versions in the form of gels, lotions, creams and ointment etc. Additionally, the aged oil has shown more allergic reactions primarily due to presence of oxidized compounds and

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peroxides in the aged oil. The aged oil was also found to contain higher amounts of degradation products like ascaridole. Generally, this oil resulted in skin inflammation and rashes (Rirdc, 2007). It was also observed that the components in TTO may penetrate the skin alongside increasing the penetration of other compounds in the skin that may subsequently increase the chances of toxicity due to higher exposure/dose of particular compound. Furthermore, ingestion of even small volumes (10–25 mL) of TTO can cause poisoning. The dermal allergic problems are quite common in contact sensitization. Furthermore, a case study also reported that a subject bear to remain in coma for 12 h upon ingestion of half cup of TTO. The subject further remained semiconscious for 36 h after reverting from coma (Carson et al., 1998). The allergic reactions and contact sensitization have been reported upon exposure with 5%–10% TTO (Larson and Jacob, 2012). Other adverse dermatological reactions, idiopathic male prepubertal gynecomastia, systemic contact dermatitis, erythema multiforme-like reactions, and linear immunoglobulin disease (Pazyar et al., 2013). The toxicity of TTO decreases when it is emulsified in the form of nanoemulsions increasing the survival time of experimental subjects (Wei et al., 2021). Furthermore, it has been noted that there are over 100 compounds found in TTO to which data in detail are readily available. Nevertheless, toxicological data for individual compound may be available in different studies but that cannot be used establishing the overall toxicity profile of the TTO as a whole (Hammer et al., 2006). Similarly, the toxicological data for TTO cannot overrule the individual toxicity of the component contained in as a slight amount of a component may induce allergic effects to a sensitive person. Moreover, there is a lack of data in complete bio-absorption and metabolism of individual compounds contained in the TTO that further narrows the projection of establishing a firm toxic or allergic dose of the oil. In this respect, comprehensive research studies are required to better understand the toxicological impact of the oil and to find accurately the compounds causing allergic reactions and their synergistic or antagonistic effects in TTO and the products containing TTO as ingredient. The deep dive in toxicological insights of TTO compounds will not only open the new horizons of research in toxicity but also help in identifying the major bioactive compounds capable of playing part in health maintenance and disease prevention.

20.6 Conclusions Above discussion summarized that TTO is an important natural product that can be utilized for numerous agrofood, pharmaceutical, and cosmetic applications. Due to diversity of its phytochemical compounds and numerous beneficial effects, the use of TTO is increasing day by day. However, the safety concerns related to TTO usage including allergic reactions need to be addressed in commercial products. It is; therefore, alternative and safer delivery systems should be designed to lower the relative toxicity of the compounds present in the TTO. Furthermore, comprehensive research is needed to better understand the toxicological role of the oil and to find accurately the compounds causing allergic reactions and their synergistic or antagonistic potency in TTO and the products containing TTO as formulation ingredient.

References

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Index Note: Page numbers followed by f indicate figures and t indicate tables.

A Agrofood uses food preservatives, 60–62 green pesticides, 58–59 packaging materials, 62–63 Apiaceae family dill antimicrobial activity, 278–288, 279–283t antioxidant activity, 277 chemical compound, 275f chemical profile, 269–274t, 276 cytotoxic and beneficial effects, 296–297t essential oil production, 254–259 extraction techniques, 261–264t, 265–266 food applications, 291–292 non-food applications, 292–294 pharmacological properties, 284–286t, 290–291 safety and toxicity, 294–298 trade and regulation of, 298–300 essential oils extracted, 243 herb processing, 242 lovage antimicrobial activity, 278–288, 279–283t antioxidant activity, 278 chemical compound, 277f chemical profile, 268–275, 269–274t cytotoxic and beneficial effects, 296–297t essential oil production, 259–260 extraction techniques, 261–264t, 266–268 food applications, 291–292 non-food applications, 292–294 pharmacological properties, 284–286t, 291 safety and toxicity, 294–298 trade and regulation of, 298–300 parsley antimicrobial activity, 278–288, 279–283t antioxidant activity, 276–277 chemical profile, 268, 269–274t cytotoxic and beneficial effects, 296–297t essential oil production, 243–254, 244–250t extraction techniques, 260–265, 261–264t food applications, 291–292

non-food applications, 292–294 pharmacological properties, 284–286t, 288–290 safety and toxicity, 294–298 trade and regulation of, 298–300 pharmacological activities, 242–243 solvent extraction, 242 toxicity of, 243 Aromatherapy aroma and therapy, 55 essentials oils in, 55f eucalyptus plant, 56 lavender, 56–57 lemon, 57 plants species, 58t rosemary, 57 tea tree, 57–58

C Cinnamon essential oil characterization of, 383 extraction techniques, 382t conventional extraction, 380 hydrodistillation, 379 ohmic heating-assisted hydrodistillation (OAHD), 381 reflux extraction (RE), 381 Soxhlet extraction, 379 supercritical fluid extraction (SFE), 380 ultrasound-assisted extraction (UAE), 380–381 in food and nonfood industries, 386–387 food safety, 377–378 health benefits antidiabetic, 385 antiinflammatory, 383–384 antioxidant activity, 385–386 antitumor and anticancer, 384–385 overview, 377–378 production and composition, 378–382 Citrus essential oil applications of antiinflammatory activity, 202 antimicrobial and antifungal activity, 203–205, 204t

501

502

Index

Citrus essential oil (Continued) antioxidant activity, 200–202, 200f antiprotozoal activity, 203 antitumor assay, 202–203 insecticidal activity, 205–206 phytoconstituents, 198–199t coaxial microwave assisted technology, 200f composition of, 195–197 extraction and characterization cold pressing (CP) method, 182–183 conventional extraction process, 180–182 enzyme assisted extraction (EAE), 194–195 hybrid techniques, 180–182 hydrodistillation (HD) method, 184–185 ionic liquid-based microwave-assisted extraction (MAE-IL) method, 190–191 microwave accelerated distillation (MAD) method, 192–193 microwave-assisted extraction (MAE) method, 187–188 microwave-assisted hydrodistillation (MAHD) method, 188–190, 189t microwave hydrodiffusion and gravity (MHG) method, 191–192 solar hydrodistillation (SSD) method, 180–182 solvent extraction (SE) method, 183 steam distillation (SD) method, 183–184 supercritical fluid extraction, 193–194 ultrasound-assisted extraction (UAE), 185–187 future aspects, 206–207 GC-MS analysis of composition, 196t medicinal and pharmacological properties, 179–180 overview, 179–180 structures of, 197t Clary sage essential oil agro-food applications, 472 characterization of, 466–467 chemistry and properties, 467 combination methods, 466 distillation hydrodiffusion, 464 hydrodistillation, 464 steam distillation, 464 nonfood applications cosmetics, 473 perfumery, 472 wound dressings and smart packaging, 473 overview, 459–460 pharmacological applications antianxiolytic, 467–468 antibacterial activity, 468–469 antidepressant and stress-relieving properties, 470

antidiabetic properties, 471 antifungal activity, 469 antiinflammatory properties, 471 antioxidant efficacy, 471 antiviral activity, 470 cytotoxic effect, 470–471 significance in women health, 468 production and chemical composition, 460–462 safety, toxicity and regulation, 473–474 Salvia sclarea, 460, 462–463t solvent extraction subcritical water, 465 supercritical carbon dioxide, 465 solvent-free microwave extraction (SFME), 465–466 trade, storage, stability, and transport, 474 Clevenger method, 88–89 Clove oil bakery and table margarine, 333–336 botanical description benefits of, 328f linolenic acid in body, 326f production of food grade, 327f Syzygium aromaticum, 326 traditional method, 327f winterization of, 328f chemical characteristics, 335t dairy whitener tea/coffee whitener, 337 DHAand EPA on stress, 339–340 extraction by enzymes, 329–330 fatty acid profiles, 336t fortification of foods, 331–333 impurities and their removal free fatty acids, 329 phospholipids, 329 induction period, 337t lipid oxidation, 331 mayonnaise, 338–339 nondairy versions, 337 overview, 325–326 polyunsaturated fatty acids, 334t, 339–340 stearin and olein fractions, 338 sterols, 335t super critical fluid extraction (SCF), 330, 330t whipped cream dairy, 337 Cold pressing (CP) method, 182–183

D Dill antimicrobial activity, 278–288, 279–283t antioxidant activity, 277 chemical compound, 275f chemical profile, 269–274t, 276 cytotoxic and beneficial effects, 296–297t

Index

essential oil production, 254–259 extraction techniques, 261–264t, 265–266 food applications, 291–292 non-food applications, 292–294 pharmacological properties, 284–286t, 290–291 safety and toxicity, 294–298 trade and regulation of, 298–300

E Enfleurage, 37–38 Essential oils biocontrol agents, 77t chemical transformation enzyme-assisted extraction (EAE), 45 microwave-assisted extraction (MAE), 45 simulated moving bed chromatography (SMBC), 44 supercritical fluid chromatography (SFC), 44 ultrasound-assisted extraction (UAE), 44–45 elaborated industry wise utilization, 38f enfleurage pomade, 37–38 extraction methods solvent extraction, 43 steam distillation, 41–43, 42f water distillation (hydrodistillation), 41, 42t future aspects, 76–77 innovatory extraction methods, 39–40 isolation and purification techniques column chromatography, 43 high-performance liquid chromatography, 44 HPTLC plates, 40 OPLC, 41 thin layer chromatography (TLC), 43 medicinal uses, 70–71t orange and grapefruit, 179–180 overview, 37–38 pulsed electric field (PEF) extraction, 40 solvent-free microwave extraction (SFME), 39–40 subcritical liquid extraction (SLE), 39 supercritical fluid extraction (ScFE), 39 Essential oils (EOs) applications anticancer, 24–25 antidiabetic agents, 22–23 antihyperpigmentation, 22 antiinflammatory, 22 antimicrobial, 23–24 antioxidant, 21 antiviral role, 24 cardioprotective, 25 hepatoprotective, 26 neuroprotective, 25–26

503 aromatherapy, 55–58 aromatic molecules, 54 autotoxicity, 2 characterization, 20–21 conventional extraction methods hydrodiffusion, 18 hydrodistillation (HD), 17 solvent extraction, 18 steam distillation (SD), 17–18 crop protection, 60t definition, 1–2 economic importance, 69–75 aniseed oil, 72 coriander seed oil, 73 cornmint oil, 74–75 cumin seed oil, 72 fennel seed oil, 73 geranium oil, 73–74 laurel oil, 72 myrtle oil, 73 oregano oil, 72 patchouli oil, 74 rosemary oil, 72 rose sector, 72 sage oil, 72 sandalwood oil, 74 ylang oil, 73 extrinsic factors, 2 innovative extraction methods solvent-free microwave extraction, 20 subcritical extraction liquid (SEL) technique, 20 supercritical fluid extraction (SFE) technique, 19 intrinsic factors, 2 natural variation, 8–16 chemical classes, structural representation, and therapeutic properties, 12–15t extraction methodologies, 9–11t LD50 values, 16t packaging materials, 62–63 phytochemistry alkaloids, 6 alpha-pinene, 3 coumarins, 6–7 flavonoids, 5 glycosides, 5–6 phenols, 6 plant-based essential oils, 7–8t saponins, 7 steroids, 3–4 tannins, 4–5 terpenes, 3 safety concerns, 26–27 the soul of plants, 53–54

504 Essential oils (EOs) (Continued) steam distillation, 54 Worldwide production, 2 Eucalyptus citridora (lemon eucalyptus), 220 Eucalyptus essential oils in active food packaging, 230–231 in agro-industry herbicides, 230 insect repellent, 230 nonfood products, 230 antibacterial, 218, 229 anticancer, 229 antidiabetic, 229 characterization and identification, 224–225 chemistry and properties, 225 E. oleosa essential oils, 221 fruits, 221 leaves essential oil, 221 stems essential oil, 221 extraction strategies, 223 in fragrance industry air fresheners, 231 humidifier, 231 skin benefits, 231 functional applications antifungal activity, 227–228 antimicrobial properties, 226–227 antioxidant activity, 228 aromatherapy, 226 insecticidal activity, 228 history, 219 hydro-distillation, 223 medical and commercial applications, 218 microwave-assisted essential oil extraction (MAEOE), 224 oil yield, 225 overview, 217–218 in pharmaceuticals, 228–229 production, 220–221 safety cosmetics ingredients, 232 drug ingredients, 233 food ingredients, 232–233 steam distillation, 223 storage stability, 235 subcritical-water extraction (SWE), 224 supercritical fluid extraction (SFE), 223 toxicity and regulation inhalation, 234 oral ingestion, 233–234 transport of, 235

Index

types of Eucalyptus citridora (lemon eucalyptus), 220 Eucalyptus globulus (blue gum), 219 Eucalyptus polybractea (blue mallee), 219–220 Eucalyptus radiata (Eucalyptus radiata), 220 vacuum distillation, 223 World-wide trade, 234–235 Eucalyptus globulus (blue gum), 219 Eucalyptus polybractea (blue mallee), 219–220 Eucalyptus radiata (Eucalyptus radiata), 220

F Flavor and Extract Manufacturers Association (FEMA), 135–136 Food preservation, 75

G Gastroesophageal reflux disease (GERD), 116 Ginger essential oil (GEO) advanced methods of extraction microwave-assisted hydro-distillation (MAHD), 357 microwave hydro-diffusion and gravity (MHG), 357–358 solvent-free microwave extraction (SFME), 357 subcritical water extraction (SWE) process, 356–357 supercritical CO2 extraction, 356 analytical method for characterization 13 C NMR analysis, 360–361 GC–MS analysis, 358–360 applications of, 367–368 chemical composition and yield drying methods on chemical components, 351 extraction method on chemical components, 351–352 geographical location on chemical components, 349, 350–351t maturity and variety on chemical components, 349–351 conventional methods of extraction hydro-distillation (HD), 353–354 solvent extraction/liquid–liquid extraction, 354–355 Soxhlet extraction technique, 355 steam distillation (SD), 354 overview, 345–346 pharmacological activities, 359t, 361–367 anticancer activity, 364 antidiabetic activity, 365 anti-inflammatory and analgesic effects, 362–363 antimicrobial activity, 363–364 anti-obesity activity, 365 antioxidant activity, 362 anti-ulcer effects, 366

Index

aromatherapy, 366–367 bronchodilation effects, 366 immunomodulatory effects, 366 insecticide action, 367 neuroprotection, 364–365 physiochemical characteristics, 352t productions of, 346–348 safety, toxicity, and regulation, 368 trade, storage stability and transport, 368–369

H High-performance thin layer chromatography (HPTLC) plates, 40

I Ionic liquid-based microwave-assisted extraction (MAE-IL) method, 190–191

J Jasmine essential oil analysis of, 160 applications of acaricidal potential, 168–169 antimicrobial activity, 166 antioxidant and anticancer potential, 167–168 Chinese and Ayurvedic medicine, 165 food preservation potential, 169 xanthine oxidase, 169 chemistry and properties Benzyl alcohol, 163–164 indoles, 164–165 Linalool, 162–163 Methyl linoleate, 164 CLP (classification, labeling, packaging) regulation, 170–171 composition and physicochemical properties, 153–155 extraction techniques steam distillation, 156–158 super critical fluid extraction (SFE), 158–160 growth and development, 151 harvesting and handling, 152–153 husbandry, 152 Jasmine (Jasminum spp.), 148 methods of extraction, 154–155t planting and propagation, 151 production and market trends, 149–151 safety, toxicity, and regulations, 170–171 species, 148–149 trade, storage stability, and transport, 171–172 using NMR spectroscopy, 160–161 volatile and semi-volatile organic compounds, 147

Juniper essential oil analgesic activity, 424 antibacterial activity, 424 anticataleptic activity, 425 antidiabetic activity, 422–423 antifungal activity, 425 antihyperlipidemic activity, 423–424 antiinflammatory activity, 421–422 antimalarial activity, 425 antimicrobial activity, 424–425 antioxidant activity, 421 applications, 420 distribution of, 416t extraction techniques, 419 hepatoprotective activity, 421 neuroprotective activity, 425 overview, 415–419 phoenicea, 417 production and composition, 419 soil limitation, 418–419

L Lamiaceae family rosemary, thyme, mint, basil) agro-food, 318–319 chemical composition, 309–310 components of, 312–313t essential oil of, 310 extraction techniques, 313–314 non-food applications, 320 Ocimum basilicum L., 311 overview, 310 pharmacological applications, 317–318 potential applications, 317f Rosmarinus officinalis L., 310 safety, toxicity, and regulation, 314–316 storage stability, 316 Lavender oil agrofood application, 96 biochemical profile, 87 chemical profile, 88t chemistry and their properties bioactive compounds, 88t carvacrol, 92 eucalyptol, 91–92 linalool, 90 linalyl acetate, 91 α-Terpineol, 92 cosmetic products, 86 current status, 86–87 extraction techniques, 87–89 food quality and safety, 97 legislations, 98 nonfood applications, 96

505

506 Lavender oil (Continued) structural and nutritional characterization, 89–90 therapeutic potential anticancer, 95 antidepressant, 93–94 antihair fall, 95 antiinflammatory, 95 antimicrobial, 94 antioxidant, 94 aromatherapy, 92–93 bioactive compounds, 91t cardioprotective, 95 digestive problems, 95 toxicity, 97–98 trade, storage stability, and transportation, 98 Lovage antimicrobial activity, 278–288, 279–283t antioxidant activity, 278 chemical compound, 277f chemical profile, 268–275, 269–274t cytotoxic and beneficial effects, 296–297t essential oil production, 259–260 extraction techniques, 261–264t, 266–268 food applications, 291–292 non-food applications, 292–294 pharmacological properties, 284–286t, 291 safety and toxicity, 294–298 trade and regulation of, 298–300

M Medicinal uses antibacterial, 64, 65f, 76 anticancer, 66 anticholinesterase potential, 69 antidiabetic, 67, 68f antifungal, 65–66, 66f, 76 antiinflammatory, 66–67 antioxidant, 64 antiprotozoal, 68 antiviral, 67 anxiolytic potential, 69 essential oils, 70–71t Melaleuca alternifolia, 485 Microwave accelerated distillation (MAD) method, 192–193 Microwave-assisted extraction (MAE) method, 187–188 Microwave-assisted hydro-distillation (MAHD) method, 188–190, 189t, 357 Microwave hydro-diffusion and gravity (MHG), 191–192, 357–358

Index

N Nutmeg essential oil antioxidants, 396–397 botanical aspects, 392 composition of, 393, 394t essential oil production, 392, 393t extraction of, 393–394 in food industry, 395–397 overview, 391–392 safety, toxicity, and regulation, 397 uses and applications, 394–397

O Ocimum basilicum L., 311 Ohmic heating, 381 Optimum performance laminar chromatography (OPLC), 41

P Parsley antimicrobial activity, 278–288, 279–283t antioxidant activity, 276–277 chemical profile, 268, 269–274t cytotoxic and beneficial effects, 296–297t essential oil production, 243–254, 244–250t developmental stage, 253 fertilization, 252 water and soil salinity stress, 252–253 yield and quality, 253 extraction techniques, 260–265, 261–264t food applications, 291–292 non-food applications, 292–294 pharmacological properties, 284–286t, 288–290 safety and toxicity, 294–298 trade and regulation of, 298–300 Patchouli essential oil adulteration and contamination, 431–432 analgesic effect, 447–448 antidiabetic effect, 446 antidiarrheal effect, 446 antiemetic effect, 446 antihypertensive effect, 446 antiinflammatory effect, 447 antimicrobial effect, 448 antioxidant effect, 447 antitumor effect, 447 aromatherapy, 444 chemical composition of, 438–442t chemistry and properties, 437–443 chiral GC, 435 chromatographic fingerprint, 435–436 constituents of, 431t, 437t effect on ischemia/reperfusion (I/R) injury, 446

Index

gastrointestinal protective effect, 445 hydrodistillation, 433 immunoregulatory effect, 448 insecticidal effect, 449 intestinal microecology effect, 446 microwave air-hydrodistillation, 433 microwave hydrodistillation, 433 odor of, 432 overview, 429–430 pharmacological activities, 444–449 physicochemical properties, 444t production and composition, 430–432 safety, toxicity, and regulation, 449–450 solvent-free microwave extraction, 434 steam distillation, 433 trade, storage stability, and transport, 450–451 two-dimensional gas chromatography (2D-GC), 434–435 ultrasonic assisted solvent extraction, 434 Peppermint essential oil antimicrobial properties, 111–112 characterization of, 110–111 comparative assessment, 108t composition of, 106t efficacy of, 112–114t fatty acid composition, 107 hydrodistillation, 108–109 irritable bowel syndrome (IBS), 115 Lamiaceae family, 103–104 lifestyle changes and GERD, 116 medicinal applications and chemical compounds, 104t microwave assisted extraction (MAE), 109–110 natural hybrid, 105f overview, 103–104 pharmaceutical industries, 104–105 relieves pain, 115 solvent extraction, 109 steam distillation, 107–108 supercritical fluid extraction (SFE), 110 toxicity, 115–116 Phototoxicity, 27 Phytochemistry alkaloids, 6 alpha-pinene, 3 coumarins, 6–7 flavonoids, 5 glycosides, 5–6 phenols, 6 plant-based essential oils, 7–8t saponins, 7 steroids, 3–4

tannins, 4–5 terpenes, 3 Pulsed electric field (PEF) extraction, 40

R Rosewood essential oil characterization of, 407 chemical characterization, 406–407 composition of, 402–403 conventional extraction methods hydro-diffusion, 404–405 hydro-distillation, 404 solvent extraction, 405 steam distillation, 403 extraction techniques, 404f food applications, 408–409 innovative extraction technology microwave-assisted extraction, 406 supercritical fluid extraction, 405 ultrasonic assisted extraction, 406 overview, 401 pharmacological applications, 407 production of, 402 safety and toxicity, 409 storage stability, 409–410 trade of, 410 Rosmarinus officinalis L., 46–48t, 310

S Salvia sclarea, 460, 462–463t Sandalwood essential oil α–santalol, 129–131 Ayurvedic therapeutic representative, 140 medicinal properties, 136 methods of extraction, 128–129 overview, 121–123 production and composition of, 131–135 safety of, 136 Santalum album (Indian sandalwood), 121–123, 131–132 Santalum austrocaledonicum, 127, 132 Santalum lanceolatum, 127–128 Santalum macgregorii, 128 Santalum paniculatum (Hawaiian sandalwood), 126 Santalum spicatum (Western Australian sandalwood), 125–126 Santalum yasi, 126–127 sapwood, 121–122 species wise santalol content, 133t steam distillation, 137 suspected fragrance allergy, 136–137 therapeutic benefits of, 129–131

507

508

Index

Sandalwood essential oil (Continued) trade and storage stability, 137–139 treatment of, 122–123 Santalum album (Indian sandalwood), 121–123, 131–132 Santalum austrocaledonicum, 127, 132 Santalum ellipticum, 132 Santalum lanceolatum, 127–128 Santalum macgregorii, 128 Santalum paniculatum (Hawaiian sandalwood), 126 Santalum spicatum (Western Australian sandalwood), 125–126, 132 Santalum yasi, 126–127 Solar hydrodistillation (SSD) method, 180–182 Solvent-free microwave extraction (SFME), 39–40, 357 Soxhlet extraction technique, 355 Subcritical water extraction (SWE) process, 356–357

overview, 479–480 oxidation and hydrolysis of α-terpinene, 484f pharmacological applications acaridical properties, 492–493 anticancer, 491–492 antiinflammatory properties, 491 antimicrobial applications, 489–491, 490t antioxidant, 491 topical, herbal and therapeutic applications, 493–494 phytochemical constituents, 480f safety concerns, 495–496 solvent extraction, 488 steam distillation extraction, 485–486 steam distillation process, 486–487, 486f advantages, 487 components, 486 modifications in, 487–488

T Tea tree essential oil agrofood applications, 494 chemical constituents, 481–483t conventional steam distillation, 488 Melaleuca alternifolia, 485 nonfood applications, 494–495

W Wound healing time reduction, 27

X Xanthine oxidase inhibitory activity, 169