Scientific collaboration between Pakistan and Kazakhstan. 9786010438460

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AL-FARABI KAZAKH NATIONAL UNIVERSITY

SCIENTIFIC COLLABORATION BETWEEN PAKISTAN AND KAZAKHSTAN 20 years working together Compilers Prof. Dr. Zh.A. Abilov and Prof.Dr. M.Iqbal Choudhary Monograph Stereotypical pyblication

Almaty «Kazakh University» 2020

UDC 547:001.83(574+549.1)

S 92 Scientific collaboration between Pakistan and Kazakhstan. 20 years working together: monograph / compilers Prof. Dr. Zh.A. Abilov and Prof.Dr. M. Iqbal Choudhary. – Ster. pub. – Almaty: Kazakh University, 2020. – 156 p. ISBN 978-601-04-3846-0 This book is dedicated to collaborative work between the scientists of International Center for Chemical and Biological Sciences (H.E.J. Research Institute of Chemistry, Dr. Panjwani Center for Molecular Medicine and Drug Research) and Al-Farabi Kazakh National University under the Scientific Collaboration Protocol funded by the Ministry of Science and Technology, Government of Pakistan and Ministry of Education and Science, Republic of Kazakhstan. This book includes results of the collaborative work conducted in the field of organic chemistry, pharmacology and chemistry of natural compounds and polymers. Intended for undergraduate, graduate and PhD student’s speacializing in field of organic chemistry, pharmacology and chemistry of natural compounds and polymers.

UDC 547:001.83(574+549.1)

ISBN 978-601-04-3846-0

 compilers Abilov Zh.A. and M.Iqbal Choudhary, 2020  Al-Farabi KazNU, 2020

CONTENT Foreword....................................................................................................................... 5 Предисловие ................................................................................................................ 7 Abstract – English ........................................................................................................ 8 Introduction .................................................................................................................. 9 Scientific Visits (PAKISTAN) ..................................................................................... 10 Scientific Visits (KAZAKHSTAN) .............................................................................. 14 Joint Scientific Publications ......................................................................................... 25 A.F. Miftakhova, G.Sh. Burasheva, Zh.A.Abilov, V.U. Ahmad, M.Zahid Coumarins from the aerial part of Halocnemum strobilaceum //Fitoterapia, 2001. ........................ 27 Sultanova N., Makhmoor T., Abilov Zh.A., Omurkamzinova V.B., Atta-ur-Rahman, M.I.Choudhary. Antioxidant and antimicrobial activities of Tamarix ramosissima // Journal of Ethnopharmocology, 2001 ........................................................................... 30 N. A. Sultanova, Zh. A. Abilov, V. B. Omurkamzinova, I. M. Chaudri, Flavonoids of The Aerial Part of Tamarix hispida //Chemistry of Natural Compounds, 2002 ....... 35 A.K. Umbetova, Sh. Zh. Esirkegenova, I. M. Chaudri, V.B. Omurkamzinova, Zh. A. Abilov Flavonoids of plants from the genus tamarix //Chemistry of Natural Compounds, 2004 ........................................................................................ 37  Eskalieva B.K., A. Akhmed., Burasheva G.Sh., Ahmad V.U., Abilov Zh.A. Biological active compounds from Climacoptera // Chemistry of natural compounds – 2004 ........................................................................................................ 39  Sultanova N., Makhmoor T., Yasin A., Abilov Zh.A., Omurkamzinova V.B., Atta-ur-Rahman, Choudhary M.I. Isotamarixen- A New Antioxidant and Propyl Endopeptidase-Inhibiting Triterpenoid from Tamarix hispida // Planta Medica, 2004 .............................................................................................................................. 41  A. K. Umbetova, M. I. Choudhary, G. Sh. Burasheva, N. A. Sultanova, Zh. A. Abilov, Biologically Active Substances from Camphorosma monspeliacum // Chemistry of Natural Compounds, 2005 ...................................................................... 44  A. K. Umbetova, M. I. Choudhary, N. A. Sultanova, G. Sh. Burasheva, Zh. A. Abilov, Flavonoids of Plants From The Genus Tamarix //Chemistry of Natural Compounds, 2005 ......................................................................................................... 46  Yeskaliyeva Balakyz., Ahmed M. Mesaik., Ahmed Abbaskhan., Aisha Kulsoom., Burasheva G.Sh., Abilov Zh.A., Iqbal M. Choudhary., Atta-ur-Rahman. Bioactive flavonoids and saponins from Climacoptera obtusifolia // Phytochemistry. – 2006 .... 48  A. K. Umbetova, M. I. Choudhary, N. A. Sultanova, G. Sh. Burasheva, Zh. A. Abilov, Triterpenoids from Plants of The Genus Tamarix //Chemistry of Natural Compounds, 2006 .............................................................................................................................. 54  Siddiqui B.S., Karzhaubekova Zh.Zh., Burasheva G.Sh., Sultanova N.A. Triterpenoids from the Aerial Parts of Kalidium foliatum //Helvetica Chimica Actа. – 2006 ............ 58  B.M. Kudaibergenova, Sh.N. Zhumagalieva, M.K. Beisebekov, Zh.A. Abilov, M.I. Chaudkhari, Composite Supports Based on Bentonite Clay and Polysaccharides // Russian Journal of Applied Chemistry, 2008 ............................................................... 67 B. Sh. Siddiqui, Zh.Zh Karzhaubekova, G.Sh. Burasheva, N.A. Sultanova, Chemical Constituents of the Aerial Parts of Kalidium foliatum //Chem. Pharm. Bull. 2007 ...... 71 Korulkina L.M., Zhusupova G.E., Shulc E.E., Abilov Zh.A., Erzhanov R.B., Choudhary M.I. Bioactive compounds of Limmonium Gmelini and Limonium Popovi (Plumbaginaceae) //Chemistry of natural compounds, 2004 ....................................... 76  B.Sh. Siddiqui, K. Zh. Butabayeva, G .Sh. Burasheva, S. Perwaiz, S.K. Ali a, H.A. Bhatti, A new lignin and a new sesquiterpene from Eurotia ceratoides (L.) // Tetrahedron, 2010 ......................................................................................................... 80

Сейтимова Г.А., Ескалиева Б.К., Бурашева Г.Ш., Чаудри И.М. Свехкритическая флюидная СО2-экстракция растения рода Climacoptera (Климакоптера) //  Материалы второй Междунар.науч.-практ. интернет-конф. Лекарственное растениеводство: от опыта прошлого к современным технологиям. –   Полтава, 2013 .............................................................................................................. 85  Сейтимова Г.А., Ескалиева Б.К., Бурашева Г.Ш., Чаудри И.М. Сравнительный компонентный анализ некоторых видов растений рода Climacoptera //  Лекарственные растения: фундаментальные и прикладные проблемы:   материалы I Междунар. науч. конф. Новосиб. гос. аграр. ун-т. –   Новосибирск: Изд-во НГАУ, 2013 ............................................................................ 89  Сейтимова Г.А., Ескалиева Б.К., Бауыржанов К.Б., Чаудри И.М., Бурашева Г.Ш., Амино-, Жирно-, Фенолокислотный состав некоторых видов растений рода Climacoptera (Климакоптера) //Известия Научно-Технического Общества «Кахак», 2013 .............................................................................................................. 92 G. A. Seitimova, B. K. Eskalieva, G. Sh. Burasheva, M. Iqbal Choudhary, Biologically Active Compounds from Climacoptera Obtusifolia // Chemistry of Natural Compounds, 2014 ...................................................................... 98 A. K. Kipchakbaeva, B. K. Eskalieva, G. Sh. Burasheva, Achyut Adikari, H. A. Aisa, M. Iqbal Choudhary Saponins from Climacoptera subcrassa //Chemistry of Natural Compounds, 2016 ......................................................................................................... 100 Seitimova G.A., Alzhanbayeva A.M., Burasheva G.Sh., Yeskaliyeva B.K., Choudhary M.I. Phytochemical study of Kochia prostrata //International Journal of Biology and Chemistry 9, 2016 .................................................................................... 102 A. K. Kipchakbaeva, R. A.-A. Khamid, B. K. Eskalieva, G. Sh. Burasheva, Zh. A. Abilov, S. R. Numonov, H. A. Aisa, Method For Obtaining Total Flavonoids From Climacoptera Subcrassa And Their Biological Activity //Chemistry of Natural Compounds, 2016 ......................................................................................................... 106 G.A.Seitimova, A.K. Kipchakbayeva G.Sh Burasheva, H.A.Aisa, M.Iqbal Choudhary Comparative analysis of the chemical composition and biological activities of some species of Climacoptera // Scientific journal of the modern education and research institute the kingdom Belgium “Innovation methods of teaching and learning” 12-19 June 2016 ...................................................................................................................... 108 M. M. Nykmukanova, B. K. Eskalieva, G. Sh. Burasheva, M. Iqbal Choudhary, Achyut Adhikari, D. Amadou, Iridoids from Verbascum marschallianum // Chemistry of Natural Compounds, 2017 ........................................................................................ 116 G. A. Seitimova, B. K. Eskalieva, G. Sh. Burasheva, M. Iqbal Choudhary, Achyut Adhikari, Polyphenols From Several Psammopelitohalophytes // Chemistry of Natural Compounds, 2017 ......................................................................................................... 118 G. A. Seitimova, B. K. Eskalieva, G. Sh. Burasheva, M. Iqbal Choudhary, Phenanthrenes From Kochia Prostrata // Chemistry of Natural Compounds, 2018 ..... 120 Y.S. Ikhsanov, Z.A. Abilov, N.A. Sultanova, M.I. Choudhary, Investigation of Components of Hexane Extract from Tamarix Hispida by Method of Gas Chromatography //Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2018.............. 122 Research publications................................................................................................. 127 20 Years Together… .................................................................................................... 133

FOREWORD

The international cooperation is one of the priorities of the Al-Farabi Kazakh National University as an indispensable part of integration into the global educational and scientific community as an important tool in ensuring a high quality education and scientific research conducted in accordance with international requirements. One of the important tasks of the Al-Farabi Kazakh National University in the field of international relations is the development and consolidation of cooperation with leading foreign universities and research centers. Currently, Kazakhstan has created all necessary conditions for such cooperation through international agreements. Diverse in form and content of scientific communications of the AlFarabi Kazakh National University in the framework of these agreements are carried out with a number of foreign research institutions and universities in the USA, UK, Germany, Austria, France, Finland, China, India, Pakistan, Poland, the Czech Republic, Slovakia, etc. Through these relationships, joint research projects and research programs, symposiums and conferences, workshops and consultations, exchange of scientists, undergraduate program students, using the most modern scientific equipment, will be implemented. A striking example of long-term and effective international cooperation is the collaboration of Al-Farabi Kazakh National University with the Н.Е.J. Research Institute of Chemistry Dr. Panjwani Center for Molecular Medicine and Drug Research, University of Karachi (Pakistan), which is implemented within the framework of scientific and technological cooperation between the Ministry of Education and Science of the Republic of Kazakhstan and the Ministry of Science and Technology of Pakistan. The program provides solving a wide range of scientific, technological and technical problems in the field of synthetic organic substances, natural compounds and pharmacology. Results of this scientific cooperation were published in 70 manuscripts of per-reviewed international journals such as Fitoterapia, Phytochemistry, PlantaMedica, Journal of Ethnopharmocology, Chemistry of natural compounds, Helvetica Acta, Chem. Pharm. Bulleten, Journal of Applied Chemistry, and were delivered on international scientific conferences and symposia. The results of pharmacological studies are patented in 15 patents of the Republic of Kazakhstan. Joint International Workshop and Conference on phytochemistry have been held in the frame of collaboration. Academic stuff of both organizations and young scientists from the al-Farabi KazNU participated in internship programs for visiting Kazakhstan and Pakistan. The most important results of these studies are related to the problem of expanding the range of novel domestic herbal remedies with a wide spectrum of therapeutic action, as a wild plant flora of Kazakhstan is available for self-renewable raw material source of high performance, not cumulative and don't cause allergic reactions, drugs not only for medicine, but also for the veterinary and agriculture. As a part of Kazakhstan-Pakistani cooperation these research have gained impetus, their potentials are significantly increased and reached the international level. The most significant publications in the area of natural compounds, organic 5

chemistry and polymers are collected in the present book as a result of productive cooperation of Al-Farabi Kazakh National University and H.E.J. Research Institute of Chemistry Dr. Panjwani Center for Molecular Medicine and Drug Research, University of Karachi. We wish to express a confidence that such a fruitful international cooperation will be effectively continued and the results will make an outstanding contribution to the development of not only the chemistry of synthetic organic substances, natural compounds and pharmacology, but also Kazakhstan science in general. Academic NAS RK G.M. Mutanov Rector of Al-Farabi Kazakh National University

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ПРЕДИСЛОВИЕ

Данная книга посвящена 20 летию научного сотрудничества научноисследовательского института химии университета г. Карачи, международного центра химических и биологических наук и Казахским национальным университетом им. аль-Фараби в рамках соглашения между Министерством образования и науки Республики Казахстан и Министерством науки и технологий Пакистана. В рамках данного проекта Пакистан посетили 3 профессора, 1 доцент, 14 молодых ученых КазНУ им. аль-Фараби. В книге приведены основные результаты совместной научной деятельности в области органической, высокомолекулярной химии, фармакологии и химии природных соединений. Из казахстанских растительных объектов выделены и установлены структуры 300 биологически активных соединений, некоторые из которых являются новыми природными продуктами. Установлена антибактериальная, фунгицидная, антиоксидантная, антиамнезийная, антидиабетическая, иммуномоделирующая, противоопухолевая, гипертензивная, противоспалительная, фитотоксическая, цитотоксическая активность индивидуальных компонентов и экстрактов. Кроме того проведена работа в области иммобилизации лекарственных препаратов на композиционных полимерных носителях и изучена их биологическая активность. Новизна полученных результатов изложена в 70 публикациях опубликованных в специализированных ведущих международных журналах Fitoterapia, Phytochemistry, Planta Medica, Journal of Ethnopharmocology, Chemistry of natural compounds, Helvetica Acta, Chem. Pharm. Bulleten, Journal Applied Chemistry, а также апробирована на различных международных научно-практических конференциях и симпозиумах. Результаты фармакологических исследований оформлены в 15 патентах Республики Казахстан.

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ABSTRACT This book dedicate to 20 year’s of collaborative work between scientist of International center for Chemical and Biological sciences H.E.J Research Institute of Chemistry, Dr. Panjwani Center for Molecular Medicine and Drug Research and AlFarabi Kazakh National University under Scientific Collaboration Protocol funded by the Ministry of Science and Technology, Government of Pakistan and Ministry of Education and Science, Republic of Kazakhstan. Under this project Pakistan visited 3 professors, 1 associate professor, 14 young scientists from al-Farabi Kazakh National University. In this book include results of collaborative work in field of organic chemistry, pharmacology, chemistry of natural compounds and polymers. From Kazakh original plants isolated 300 biological active compounds, some of these are new. For some extracts and individual compounds established antibacterial, antifungal, antioxidant, antiamnezia, antidiabetic, growth-regulating, immunemodulatory, cytotoxic, toxicity (Brine Shrimp activity) e.t.c. activity. Immobilization of phytoremedies and drugs on composition polymer carriers has been given. Results of collaborative scientific work were published (70 research publications) in an International Journals such as Fitoterapia, Phytochemistry, Planta Medica, Journal of Ethnopharmocology, Chemistry of natural compounds, Helvetica Acta, Chem. Pharm. Bulleten, Journal Applied Chemistry e.t.c., book of Abstracts of some International Conferences and Symposium and in 15 patents of Republic of Kazakhstan.

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INTRODUCTION

One of the main objectives of the pharmaceutical program is provide for population safety and effective medicine for treatment of different diseases. Kazakhstan is rich in medicinally important flora which can use for preparations of medicine Nowadays the development preparations from medicinal plants which contain biological active compounds are very actual. It means that development of the new pharmaceutical products from plants one of the important objectives of field chemistry of natural products. In 1998 year was sign up Pak- Kazakh project Scientific Collaboration Protocol between Academy of Sciences of the Republic Kazakhstan and Ministry of Science and Technology Government of Pakistan in the field of organic chemistry and chemistry of natural compounds. During this project were studied biological active compounds and bioaasay of some original spices of genus Shueda, Tamarix, Climacoptera, Kalidium, Camforosma, Limonium, Kochia, Verbascum etc. Immobilization of phytoremedies and drugs on composition polymer carriers has been given as well. This collaborative work bring together both of scientists to open up possibilities of engaging in meaningful collaborations between two country at international levels and will encourage the entire generation of young natural product chemist. Results of collaborative scientific work were published in some an International Journals and defend 13 PhD and 3 doctoral thesis.

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SCIENTIFIC VISITS (PAKISTAN) PROF. DR. ATTA-UR –RAHMAN, FRS Nishan-e-Imtiaz, Hilal-e-Imtiaz, Sitara-eImtiaz, Tamgha-e-Imtiaz, Chief-Patron, ICCBS, HEC Distinguished National Professor, Sc.D. (Cantab), Hon. D.E.d. (Coventry), D.Sc. (AIT), D.Sc. (Karachi), D.Sc. (Gomal), D.Sc. (UiTM, Malysia), Ph.D. (Organic Chemistry, Cambridge, UK), UNESCO Science Laureate, Khwarizmi Laureate, Austrian Award, Vice President (TWAS), Federal Minister of Science and Technology, and Information Technology, Chairman Higher Education Commission, Coordinator General COMSTECH, President Pakistan Academy of Sciences. He is a fellow of various prestigious societies, The World academy of Sciences (TWAS), Islamic Academy of Sciences, (IAC), Fellow of Chinese Academy of Sciences, Fellow of the Royal Society (FRS), Pakistan Academy of Sciences, etc. He has 1090 publications in several fields of organic chemistry including 900 research publications, 60 patents, 250 books and 110 chapters in books published largely by major U.S. and European presses. PROF. DR. M. IQBAL CHOUDHARY Hilal-e-Imtiaz, Sitara-e-Imtiaz, Tamghae-Imtiaz, Director (ICCBS), Author / Editor of 38 books, 32 of which have been published in USA and Europe. Author of over 1100 research publications, all published in USA, Europe, and Japan (Total Impact Factor 2000), Highest number of international research papers in the country in last ten years (3% of total research publications in all disciplines), He is most cited scientist of Pakistan (23,000, h-index-62) since last 10 years, COMSTECH Award inChemistry (2010) by the Prime Minister of Pakistan (2010), Khwarizmi International Award and Prize from the President of Islamic Republic 10

of Iran (2006), Economic Cooperation Organization (ECO) Award in Education 2006 by the President of Azerbaijan, Doctor of Science (D.Sc.) University of Karachi (2005), Distinguished National Professor of the Higher Education Commission (2004), Prof. Abdus Salam (Nobel Laureate) Prize in Chemistry (1989), Prof. Raziuddin Siddiqui Gold Medal of Pakistan Academy of Sciences (1992), Third World Academy of Science Young (Trieste Italy) Scientists Award (1994), National Book Foundation Prize (1995), Visiting Professor at the University of Rhode Island, USA,Visiting Professor at the King Saud University (KSU), Riyadh, Saudi Arabia, Visiting Professor at the UniversitiTeknologi MARA (UiTM), Malaysia, Visiting Professor at the UniversitiKebangsaan Malaysia (UKM), Visiting Professor at the Al-Farabi Kazakh National University, Kazakhstan. PROF. DR. VIQAR UDDIN AHMAD Hilal-i-Imtiaz, Sitara-i-Imtiaz, Distinguished National Professor (HEC), Lifetime Achievement Award (HEC), Ph.D. (Organic Chemistry), University of Karachi (1966), Dr. rer.nat. (Synthetic Chemistry) Bonn University, Germany (1968), present Full Professor, H.E.J. Research Institute of Chemistry, University of Karachi (1976), Alexander von Humboldt Fellow, Erlangen, Germany (1988-1989), Doctor of Science (D.Sc.) University of Karachi (1992), Senior Fulbright Fellow, Ithaca, New York, USA (1993),Dean, Faculty of Science, University of Karachi (1994-2000), Research publications – 454, books –90, patents –50, Visited USA, UK, France, Brazil, Mexico, South Africa, Italy, Egypt, Malaysia, Thailand, South Korea, Sri Lanka, India and Saudi Arabia.

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PROF. DR. BINA S. SIDDIQUI Sitara-e-Imtiaz,Tamgha-e-Imtiaz, Senior Professor, ICCBS, Khwarizmi Laureate, Distinguished National Professor of HEC, D.Sc. (University of Karachi, Pakistan, Life Time Academic Achievement Award, HEC, Pakistan, First Dr. Abdus Salam Prize in Chemistry, Fellow of The World Academy of Sciences for the Developing World (TWAS), Fellow, Third World Organization for Women in Science (TWOWS), Fellow, Pakistan Academy of Science (PAS), Fellow, Chemical Society of Pakistan (CSP). 426 publications including 331 research publications, 18 patents and 77 chapters in books. (Citations 7183; h-index-43). PROF. DR. AHSANA DAR FAROOQ Currently, Adjunct Professor, Faculty of Eastern Medicine, Hamdard University, Karachi Pakistan. Dean (2016 to 2017), Area of interest includes evidence-based Unani medicine. Advisor R&D-Herbion Naturals (Pvt) Ltd, (2014-2015). Professor Pharmacology International Center for Chemical and Biological Sciences University of Karachi (uptil 2014). International Research Coordinator, ICCBS. Trained many foreign students in natural product pharmacology including nine students from Kazakhstan. Received M.Phil and PhD from Cambridge, U.K. (1992). Research publications (81), Books (20), Patents (3), Research grants (9). Visiting Professor National Cancer Institute (NCI), Frederick Maryland, U.S.A. (1994). Visiting Professor, Institute of Medicinal Plant Development (IMPLAD), Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing China (2005). Member of many academic boards and organizations

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DR. FARZANA SHAHEEN UNESCO L’OREAL Fellow (2004), Fulbright Fellow (2008), Dr. M. Raziuddin Siddiqi prize (2006), OWSD Young Women Scientist Award (2011), Ph.D. (H. E. J. Research Institute of Chemistry, 1995-2000), Research Officer (H.E.J. Research Institute of Chemistry, 20002001), Assistant Professor (H.E.J. Research Institute of Chemistry, 2001-2011), Area of research: Natural Product chemistry and combinatorial synthesis of cyclic peptides and peptidomimetics, Research publications- 50, patents 2, Visited University of Southampton under UNESCO L’OREAL Fellowship Program, 2005, Fulbright Fellow and Visiting Assistant Professor at UC-Davis during 2008-2009 DR. SHABANA USMAIN SIMJEE Associate Professor, Pharmacology, H.E.J. Research Institute of Chemistry, British Council Visitor, Under Higher Education Link Programme Scheme between HEC (Pakistan) and British Council (2009), Visiting Professor, Transfusion Medicine Unit, St. Michael’s Hospital, Toronto, Canada (2004-2005), Visiting Scholar, Programme in Integrative Biology, The Hospital for Sick Children Research Institute, Toronto, Canada (2005),Visiting Faculty, FAST Institute of Computer Science, National University of Emerging Sciences, Karachi, Pakistan (2003), Assistant Professor, Department of Biochemistry, Baqai Medical University, Karachi, Pakistan (2002-2003), Area of research: Neuropharmacology of epilepsy and chronic pain, Research Publications (52), Patent (2), Reviewer; International Immunopharmacology, Pharmaceutical Biology, Epilepsy Research, Pakistan Journal of Pharmaceutical Sciences, Journal of Basic and Applied Sciences (Pakistan), Member Editorial Board of Mediterranean Journal of Biosciences, SM Journal of Arthritis Research, American Journal of Life Sciences, Journal of Biochemistry & Molecular Medicine.

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SCIENTIFIC VISITS (KAZAKHSTAN) PROF. DR. Sc. ZHARYLKASSYN ABILOV Member of academia of Science high school RK, Honoured worker education of RK, Laureate prize “Best Scientific Scientist RK” 

1966-1971- high education of chemistry S. Kirov Kazakh State University  1971-1982 - Research fellow S.Kirov Kazakh State University  1982- Ph.D. (Colloidial chemistry) Kazakh National University  1982-1994 - Associated Professor KazNU  1993 - Doctor of Science (D.Sc.) (chemistry of high-molecular compounds) KazNU  1996 – present Full Professor KazNU  1996-2000- head of department of organic chemistry and chemistry of natural compounds  2000-2009 Dean of chemistry faculty of Al-Farabi KazNU  2009-2011 head of department of organic chemistry and chemistry of natural compounds  2011-2014 head of department of chemistry and technology of organic substances, natural compounds and polymers  Research publications - 700, 7books, 3-text book, 21-teaching quides, 82 patents of RK, temporary pharmacopeia articles - 16 of RK  Inventor of original preparations “Alhidin”, “Gauhar”, “Zhantak”, “Biosed-K”, “Sanzhar”, “Limonidine”  Visited in 1998 year as member of National Akademy of sciences RK (Islamabad, Faisalabad) 14

PROF. DR.Sc. GAUHAR BURASHEVA Laureate prize “Best Scientific Scientist RK”       

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1967-1972- high education of chemistry S. Kirov Kazakh State University 1973-1981 Research fellow Kazakh National University 1981 - Ph.D. (Chemistry of natural compounds) KazNU 1994- Associated Professor KazNU 2004 - Doctor of Science (D.Sc.) (Bioorganic Chemistry) KazNU 2008 /present Full Professor KazNU Research publications - 300, books - 5, patents – 35 RK, pharmacopeia article – 1, temporary pharmacopeia articles - 4 of RK. Inventor of original preparations “Alhidin”, “Gauhar”, “Zhantak”. Visited in 2000 year PROF. DR.Sc. MIRGUL TURMUKHANOVA

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1970-1975- high education of chemistry S.M. Kirov Kazakh State University 1976-1978 Research fellow KazNU 1978-1981 post-graduate student KazNU 1998 - Ph.D. (Organic Chemistry) KazNU 1995-2010 - Associate Professor KazNU 2010/ present – Full Professor, KazNU Research publications - 210, books -4, patents – 9 Republic of Kazakhstan and 4 Russia Visited in 2007 year

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PROF. DR. Sc. GALIYA ZHUSUPOVA Winner of the IIIrd Republican contest on achievements in the field of inventions by the Ministry of Education and Science of the Republic of Kazakhstan for 2006 in the nomination “Woman-inventor” 

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1963-1969 – studied at Moscow State University of Fine Chemical Technologies named after M.V. Lomonosov 1970-1975 – Research fellow at S. Kirov Kazakh State University 1975 – Candidate of Sciences (equivalent to PhD, Organic Chemistry, KazNU) 1975-1982 – Assistant Professor, KazNU 1983-2008 – Associate Professor, KazNU 2007 – Doctor of Sciences (D.Sc.) (Bioorganic Chemistry, KazNU) 2009 / present – Full Professor, KazNU Research publications – 350 papers and conference proceedings, 5 books, 32 patents (KZ), 2 pharmacopoeial monographs, 11 temporary pharmacopeia articles (KZ). Inventor of four original “Limonidin” preparations: substance, ointment, syrup, tincture. Visited in 2016 year

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PROF. DR.SC. GRIGORIY MUN 1977-1980 B. Sci. Mordov State University, Russia 1980-1984 Junior Scientific Fellow, Moscow State University, Moscow, Russia. 1984 - Ph.D. Moscow State University, Moscow, Russia 1984-1987 Head of technological department, Saransk, Russia 1988-1991 Senior Researcher, Department of Macromolecular Chemistry, Kazakh National State University Almaty, Kazakhstan 1991-2000 Assoc. Professor Department of Macromolecular Chemistry, Kazakh National State University, Almaty, Kazakhstan 2000-2001 Vice-Dean in charge of science Kazakh National State University, Almaty, Kazakhstan 2000-2002 Professor Dept. of Macromolecular Chemistry, Kazakh National State University, Almaty, Kazakhstan 2002-2003 Visiting Professor, Purdue University, West Lafayette, USA 2003-2004 Professor, Dept. of Chemical Physics & Macromolecular Chemistry, KazNU, Almaty, Kazakhstan 2005-2010 Head of Department, Dept. of Colloid Chemistry & Macromolecular Chemistry, KazNU Almaty, Kazakhstan 2010-2011 Head of Department, Dept. of Colloid Chemistry & Macromolecular Chemistry, KazNU Almaty, Kazakhstan 2011-2013 Member of Higher Scientific and Technical Commission on Republic of Kazakhstan Government, Ministry of Education and Science of Republic of Kazakhstan, Astana, Kazakhstan 2011-2013 Professor, Dept. of Chemistry and Technology of organic materials, polymers & Natural compounds, KazNU Almaty, Kazakhstan 2014/at present Dept. of Chemistry and Technology of organic materials, polymers & Natural compounds, KazNU Almaty, Kazakhstan 17

DR. ALFIRA MIFTAKHOVA      

1992-1996 - B.Sc. (chemistry) Al-Farabi Kazakh National University 1996-1998- (M.Sc) KazNU 1998-2000 - post-graduate student KazNU 2002- Ph. D. (bioorganic chemistry) Research publications 15, patents of Republic of Kazakhstan -1 Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. Viqar Uddin Ahmad (2000-2001).

ASSOC. PROF. DR. NURGUL SULTANOVA        

1993-1998- B.Sc. (chemistry) Kazakh National Al-Farabi University 1998-2000- (M.Sc) KazNU 2004- Ph. D. (bioorganic chemistry) 2004-2008 Senior-lecturer KazNU 2008/ present - Associate professor 2010 - Doctor of Sciences (D.Sc.) Research publications 150, 14 patents, 1 - book, 4-teaching guides, 1- introduction to medicine. Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. M. Iqbal Choudhary (2000-2001).

18

DR. LIRA KORULKINA      

1986-1990- high education of chemistry S. Kirov Kazakh State University 2001-2003 research fellow KazNU 2003-2005 - post-graduate student KazNU 2006- Ph. D. (bioorganic chemistry) Research publications 15, previously patents 5 of Republic of Kazakhstan Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. M. Iqbal Choudhary (2003).

DR. ALMAGUL UMBETOVA      

1996-2000 - B.Sc. (chemistry) Al-Farabi Kazakh National University 2000-2002- (M.Sc) KazNU 2007- Ph. D. (bioorganic chemistry) 2007/presentSenior-lecturer, KazNU Research publications 40, 7 patents of Republic of Kazakhstan, 3-text books Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. M. Iqbal Choudhary, (2003, 2005).

19

ASSOC. PROF. DR. BALAKYZ YESKALIYEVA        

1995-1999- B.Sc. (chemistry) Kazakh National Al-Farabi University 1999-2001(M.Sc) Al-Farabi KazNU 2007- Ph. D. (bioorganic chemistry) 2005-2015 - Senior-lecturer KazNU 2010-2017 – vice dean of Faculty of chemistry and chemical technology, Al-Farabi KazNU 2015/present – Associate professor Research publications 100, 4 – books, 8 patents of Republic of Kazakhstan. Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor - Prof., Dr.Viqar Uddin Ahmed and Prof., Dr. M. Iqbal Choudhary, (2003-2005).

DR. ZHANNAT KARZHAUBEKOVA     

1997-2001- B.Sc. (chemistry) Al-Farabi Kazakh National University 2001-2003- (M.Sc) KazNU 2007- Ph. D. (bioorganic chemistry) Research publications 15, innovation patents – 2 of Republic of Kazakhstan. Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor - Prof., Dr. Bina Siddiqui S, (2004-2005).

20

DR. BATES KUDAIBERGENOVA      

1998-2002- B.Sc. (chemistry) Al-Farabi Kazakh National University 2002-2004- (M.Sc) KazNU 2008Ph.D. (organometalic chemistry, catalises and natural product chemistry) 2008/ presentSenior-lecturer KazNU Research publications 30, innovation patents of Republic of Kazakhstan-3. Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. M. Iqbal Choudhary, (2006-2008). M.Sc. post-graduate student ZHANAR MYNBAEVA

   

2000-2004B.Sc. (chemistry) Eurasian national university named after L.N.Gumilev, Astana 2004-2007 - post-graduate student – Eurasian national university named after L.N.Gumilev, Astana Research publications 21 patents of Republic of Kazakhstan-3 Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. M. Iqbal Choudhary, (2007).

21

DR. RIZVANGUL IMINOVA      

2001-2004- B.Sc. (chemistry) Al-Farabi Kazakh National University 2004-2006- (M.Sc) KazNU 2009 - Ph. D. (chemistry of highmolecular compounds) 2010/present Senior-lecturer KazNU Research publications 18 Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor - Prof., Dr. Ahsana Dar, (2007)

DR. KALAMKAS BUTABAEVA    

2000-2005- high education of chemistry Al-Farabi Kazakh National University 2009 - Ph. D. (bioorganic chemistry) Research publications 10 Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. Bina Siddiqui S., (2007, 2009)

22

DR. SEITIMOVA GULNAZ  2006-2010 – (B.Sc.) Al-Farabi Kazakh National University, Faculty of Chemistry and Chemical Technology  2010-2012 – (M.Sc.) Al-Farabi Kazakh National University  2017 – Ph.D. (Chemical technology of Organic substances), Al-Farabi Kazakh National University  2014-Present – Senior Lecturer, AlFarabi Kazakh National University  Research publications – 35 papers and conference proceedings, 1 book, 2 patents (KZ).  Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. M. Iqbal Choudhary (2015, 2016) DR. ALIYA KIPCHAKBAYEVA  2001-2005– B.Sc. (chemistry) AlFarabi Kazakh National University  2005-2007– M.Sc. Al-Farabi Kazakh National University  2015 – Ph.D. (Chemical technology of Organic substances), Al-Farabi Kazakh National University  2015 – Senior lecturer, KazNU  Research publications – 25 papers and conference proceedings, 2 books, 3 patents (KZ).  Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. M. Iqbal Choudhary (2015)

23

DR. MANSHUK NYKMUKANOVA  2008-2012 – (B.Sc.) Al-Farabi Kazakh National University, Faculty of Chemistry and Chemical Technology.  2012-2014 – (M.Sc.) Al-Farabi Kazakh National University, Faculty of Chemistry and Chemical Technology.  2018 – Ph.D. (Chemistry), Al-Farabi Kazakh National University  2014-2016 – Senior Lecturer, Kazakh National University  2017-present – Senior Lecturer, S.Amanzholov East Kazakhstan State University  Research publications – 27 papers and conference proceedings, 1 patent (KZ).  Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. M. Iqbal Choudhary (2016) MR. YERBOL IKHSANOV 2010-2013 – (B.Sc.) Al-Farabi Kazakh National University 2013-2015 – M.Sc. Al-Farabi Kazakh National University 2019 – Ph.D. (Chemical technology of Organic substances), KazNU.  Research publications – 45 papers and conference proceedings, 1 patent (KZ).  Research fellow HEJ Research Institute of Chemistry University of Karachi. International Center of Sciences, Pakistan. Supervisor- Prof., Dr. M. Iqbal Choudhary (2016, 2017)

24

JOINT SCIENTIFIC PUBLICATIONS

Fitoterapia 72 Ž2001. 319᎐321

Phytochemical communication

Coumarins from the aerial part of Halocnemum strobilaceum A.F. Miftakhovaa , G.Sh. Burashevaa , Zh.A. Abilov a , V.U. Ahmadb,U , M. Zahid b b

a Department of Chemistry, Al-Farabi Kazakh State National Uni¨ ersity, Almaty, Kazakhstan H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, Uni¨ ersity of Karachi, Karachi-75270, Pakistan

Received 9 August 2000; accepted in revised form 2 November 2000

Abstract Four known coumarins, coumarin (1), 7-hydroxy-3-methylcoumarin (2), oreoselone (3) and heraclenin (4), were isolated from aerial part of Halocnemum strobilaceum. Their structures were determined by 1 and 2-D NMR techniques. 䊚 2001 Elsevier Science B.V. All rights reserved. Keywords: Halocnemum strobilaceum; Coumarins

Plant. Halocnemum strobilaceum ŽPall.. M. Bieb. ŽChenopodiaceae. aerial part was collected from the Almaty region ŽKazakhstan., in September 1999 and identified by Dr M.S. Kuznetsova ŽDepartment of Biology, Al-Farabi University, Almaty, Kazakhstan.. Uses in traditional medicine. No reports. Previously isolated constituents. Flavonoids w1x, caffeic acid esters w2x. U

Corresponding author. Tel.: q92-21-4985884; fax: q92-21-4963124. E-mail address: [email protected] ŽV.U. Ahmad.. 0367-326Xr01r$ - see front matter 䊚 2001 Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 0 0 . 0 0 3 0 1 - 4

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A.F. Miftakho¨ a et al. r Fitoterapia 72 (2001) 319᎐321

New-isolated constituents. Coumarin (1) w3x Žyield: 0.00013% on dried wt.., 7-hydroxy-3-methoxycoumarin (2) w4x Ž0.00084., oreoselone (3) w5,6x Ž0.0007., heraclenin (4) w7x Ž0.0008..

7-Hydroxy-3-methoxycoumarin (2). White powder; C 10 H 8 O 3 ; 1 H-NMR Ž400 MHz, CD3 OD.: ␦ 2.40 Ž3H, d, J 1.2 Hz, CH 3 ., 6.08 Ž1H, dd, J 1.2, 2.3 Hz, H-4., 6.68 Ž1H, d, J 2.3 Hz, H-8., 6.80 Ž1H, dd, J 2.3, 8.7 Hz, H-6., 7.58 Ž1H, d, J 2.3 Hz, H-5.; EI MS mrz: 176 ŽMq 71%., 148 Ž100.; 13 C-NMR ŽCDCl 3 q CD3 OD, 100 MHz.: 19.2 ŽCH 3 ., 162.8 ŽC-2., 113.9 ŽC-3., 111.4 ŽC-4., 127.3 ŽC-5., 114.5 ŽC-6., 164.1 ŽC-7., 103.7 ŽC-8., 156.4 ŽC-9., 155.8 ŽC-10.. Oreoselone (3). White needles; C 14 H 12 O4 ; 1 H-NMR Ž400 MHz, CD3 OD.: ␦ 0.88 Ž3H, d, J 6.8 Hz , CH 3 ., 1.16 Ž3H, d, J 6.9 Hz , CH 3 ., 2.34 Ž1H, m, CH., 4.67 Ž1H, d, J 3.9, CH., 6.35 Ž1H, d, J 9.6 Hz, H-3., 7.97 Ž1H, d, J 9.6 Hz, H-4., 7.90 Ž1H, s, H-5., 7.18 Ž1H, s, H-8.; EI MS mrz: 244 ŽMq 28%., 202 Ž100., 188 Ž24., 187 Ž25., 160 Ž23.; 13 C-NMR ŽCDCl 3 q CD3 OD, 100 MHz.: 161.5 ŽC-2., 115.1 ŽC-3., 145.6 ŽC-4., 125.7 ŽC-5., 120.2 ŽC-6., 175.4 ŽC-7., 101.5 ŽC-8., 162.0 ŽC-9., 116.2 ŽC-10., 201.4 ŽCO., 92.2 ŽCH., 32.3 ŽCH., 16.0 ŽCH 3 ., 18.8 ŽCH 3 .. Heraclenin (4). Colorless crystals ŽMeOH.; C 16 H 14 O5 ; 1 H-NMR Ž400 MHz, CD3 OD.: ␦ 1.31 Ž3H, s, CH 3 ., 1.36 Ž3H, s, CH 3 ., 3.29 Ž1H, d, J 3.8 Hz, OCH 2-C H ., 4.44 Ž2H, dd, J 3.8, 11.0 Hz, OC H2 ., 4.77 Ž2H, dd, J 7.0, 11.0 Hz, OC H2 ., 6.31 Ž1H, d, J 9.7, H-3., 7.18 Ž1H, dd, J 1.0, 2.4 Hz, H-5., 7.20 Ž1H, d, J 2.4 Hz, ␣-H of furan., 7.81 Ž1H, d, J 2.4 Hz, ␤-H of furan., 8.35 Ž1H, dd, J 0.5, 9.1 Hz, H-4.; EI MS mrz: 286 ŽMq 22%., 202 Ž15., 85 Ž87., 59 Ž100.; 13 C-NMR ŽCDCl 3 q CD3 OD, 100 MHz.: 163.3 ŽC-2., 113.7 ŽC-3., 141.2 ŽC-4., 105.8 ŽC-5.,

28

A.F. Miftakho¨ a et al. r Fitoterapia 72 (2001) 319᎐321

115.0 ŽC-6., 154.2 ŽC-7., 108.7 ŽC-8., 155.3 ŽC-9., 149.0 ŽC-10., 105.8 Ž␤-C of furan., 95.1 Ž ␣-C of furan., 73.2 ŽCH 2 ., 62.8 ŽC-1 of lactone., 60.0 ŽC-2 of lactone.. Acknowledgements We thank the Ministry of Science and Technology, Pakistan for the financial support through the Pak-Kazakh Joint Research Project entitled ‘Studies on the biologically active metabolites from plants of central Asia’.

References w1x w2x w3x w4x

Miftakhova AF, Burasheva GSh, Abilov ZhA. Khim Prirod Soedin 1999;35:100. Gibbons S, Mathew KT, Gray AI. Phytochemistry 1999;51:465. Chan KK, Giannini DD, Cain AH, Rooberts JD, Porter W, Trager WF. Tetrahedron 1977;33:899. Carmen T, Lourders S, Eugenio U, Yagamore F, Lena U, Boragnar T. Bio Organic Med Chem Lett 1998;8:3567. w5x Gaind KN, Gupta IS, Ray JN, Sareen KN. J Indian Chem Soc 1946;23:370. w6x Krivut BA, Perelson ME. Khim Prirod Soedin 1970;6:183. w7x Adityachaudhury N, Ghosh D, Choudhuri A. Phytochemistry 1974;13:235.

29

Journal of Ethnopharmacology 78 (2001) 201–205 www.elsevier.com/locate/jethpharm

Antioxidant and antimicrobial activities of Tamarix ramosissima N. Sultanova b, T. Makhmoor a, Z.A. Abilov b, Z. Parween a, V.B. Omurkamzinova b, Atta-ur-Rahman a, M. Iqbal Choudhary a,1* a

HEJ Research Institute of Chemistry, International Centre for Chemical Sciences, Uni6ersity of Karachi, Karachi 75270, Pakistan b Department of Chemistry, Al-Farabi, Kazakh State National Uni6ersity, Karasay Batir-95.A, Almaty, Kazakhstan Received 12 January 2001; received in revised form 3 September 2001; accepted 20 September 2001

Abstract The ethylacetate and water–acetone extracts of Tamarix ramosissima were screened for their antioxidant, antibacterial, antifungal and DNA damaging activities through in vitro experiments. All fractions as well as precipitates showed significant antioxidant activity. A known compound tamarixetin (1) was isolated which showed significant DNA damaging activity in mutant yeast bioassay. Results revealed that antioxidant and antibacterial activities were associated with the presence of polyphenolic substances. © 2001 Elsevier Science Ireland Ltd. All rights reserved. Keywords: Tamarix ramosissima; Tamaricaceae; Antioxidant; Antimicrobial; DNA damage; Tamarixetin

(3%,3,5,7-tetrahydroxy-4%-methoxyflavone) was isolated from the butanolic fraction of the plant, showed significant DNA damaging activity. However, this compound had not shown any antioxidant and antimicrobial activities. The plant, T. ramosissima has not been investigated earlier, although there are many reports of phytochemical work on other Tamarix species.

1. Introduction Tamarix ramosissima commonly known as tamarisk or salt cedar belongs to the family Tamaricaceae. The Tamarix species prefer alluvial soil but grow well on saline and alkaline soil. They are cultivated as ornamental plants in gardens for their pleasing pendulous panicles or racemes of small pink or whitish flowers and graceful scaly leaves. Various species of Tamarix have been used as medicament and tonic. They are useful in leucoderma, spleen troubles, and eye diseases (Sharma and Parmar, 1998). About 125 species have been reported from different regions of Europe, USA, Asia and Africa. Only 11 species and two hybrid species are found in Kazakhstan, while 16 species are reported from Pakistan. Leaves of T. ramosissima are one of the oldest herbal medicines, which have been used for the treatment of rheumatism and jaundice. The bark of this plant is used as astringent and galls possess medicinally important tannins (Komaroz, 1949; Pavlov, 1963). This plant is found to be rich in polyphenolic compounds such as flavonoids, sulphur-containing flavonoids, phenolic acids, hydrolyzable tannins and coumarins (Sokolov, 1986). The pure compound tamarixetin (1)

2. Materials and methods

2.1. Plant material Leaves of T. ramosissima Ledeb. (1 kg) were collected from the southern Kazakhstan in September 1999. Voucher specimen was deposited at the Department of Biological Sciences, Kazakh State National University (Almaty). The leaves were air-dried and powdered before extraction.

2.2. Extraction of plant material The powdered air-dried leaves (1 kg) of T. ramosissima were soaked in water:acetone (1:1) (5 l) at room temperature for 24 h. The resulting extract was concentrated at 40 °C, and precipitates thus obtained were filtered off (30 g, I). The remaining layer was further

* Corresponding authors. Fax: + 92-21-9243190/191. E-mail address: [email protected] (M.I. Choudhary). 1 E-mail: [email protected].

0378-8741/01/$ - see front matter © 2001 Elsevier Science Ireland Ltd. All rights reserved. PII: S 0 3 7 8 - 8 7 4 1 ( 0 1 ) 0 0 3 5 4 - 3

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N. Sultano6a et al. / Journal of Ethnopharmacology 78 (2001) 201–205

2.5. Antioxidant assay for DPPH free radical sca6enging acti6ity

extracted with benzene (10 g), chloroform (15 g), ethylacetate (20 g, II) and butanol (30 g, III), respectively. Butanolic extract contained precipitates, which were filtered off (2.7 g). The remaining water extract was found to be 25 g (IV). The ethylacetate fraction (20 g) was loaded on the Sephadex LH 20 column using water as eluent. The polarity of column was gradiently increased with ethanol and acetone. The mixture of tannins and other plant phenols (4 g, V) were obtained at 70% ethanol and acetone. The presence of tannins in fraction V was inferred by spraying its TLC with a saturated solution of potassium iodinate (galloyl esters as red to pink spots and gallic acid as orange–red) and freshly prepared 10% solution of sodium nitrate and acetic acid (hexahydrodiphenoyl esters as rose–red spots turning rapidly green, brown, purple and finally, indigoblue; Porter, 1989). The butanolic extract (20 g) of the plant was subjected to column chromatography over silica gel, using eluents CH2Cl2:MeOH (100 –0%) gradiently to afford compound 1 which was identified as 3%,3,5,7-tetrahydroxy-4%-methoxyflavone (tamarixetin). The yield of the compound was 8 mg (percent yield was 8×10 − 4%).

The reaction mixture contains 5 ml of test samples (various extracts and compound 1 dissolved in DMSO) and 95 ml of DPPH in ethanol. Different concentrations of test samples were prepared while the concentration of DPPH was 300 mM in the reaction mixture. These reaction mixtures were taken in 96-well plate microtitre plates (Molecular Devices, USA) and incubated at 37 °C for 30 min, the absorbance was measured at 515 nm. Percent radical scavenging activity by sample treatment was determined by comparison with a DMSO treated control group. IC50 values denote the concentration of sample which is required to scavenge 50% DPPH free radicals (Smith et al., 1987; Fujita et al., 1998). Emblica officinalis (methanolic extract) and propyl gallate were used as positive controls.

2.6. Bactericidal bioassay Bactericidal activity was determined by Broth dilution method (Finegold and Martin, 1982). In this method, decreasing concentrations of samples (extracts I–V and compound 1) were prepared in serial two-fold dilutions in DMSO and placed in screw-capped tubes of a broth medium. One drop of the test organism culture (each drop contained 105 –106 colony-forming units ‘CFU’ of overnight broth culture) was inoculated in each tube. Tubes containing DMSO and reference antibacterial drug (Tetracycline) served as negative and positive controls, respectively. All tubes (sample and controls) were incubated at 37 °C for 24 h, and growth of bacteria was visually monitored. Concentration at which no growth of bacteria was observed was taken as the minimum inhibitory concentrations (MIC) expressed in mg/ml.

2.3. Chemicals All the chemicals and nutrients were of analytical grades and were obtained from various sources. 1, 1-Diphenyl-2-picrylhydrazyl radical (DPPH, Sigma), Dimethylsulfoxide (Sigma), Methanol (Sigma), Propyl gallate (Sigma), Nutrient Agar Media (Merck), PYD Agar Media (Merck).

2.4. Microorganisms Bacterial strains (clinical isolates) including Bacillus cereus, Corynebacterium diphtheriae, Escherichia coli, Klebsiella pneumoniae, Salmonella typhi, Pseudomonas aeroginosa, Staphylococcus aureus, Shigella boydii, Streptococcus pyogenes and Proteus mirabilis were used in the antibacterial assay. Tetracycline was used as standard antibiotic in these assays. Eight different fungal pathogens, including human and plant pathogens, were used in the study. The human fungi studied were Trichophyton schoenleinii, Trichophyton simii, Trichophyton mentagrophytes, Pseuallescheria boydii, Candida albicans, Aspergillus niger and Microsporum canis. Plant fungi, Macrophomina phaseolina. Miconazole and ketoconazole were used as standard drugs in antifungal assay. The microorganisms were identified by a trained microbiologist. They are mainly of wild types. Wild type RAD + and mutant RAD52 Saccharomyces cere6isiae strains (Sigma) were used in DNA damaging yeast bioassay.

2.7. Antifungal bioassay Antifungal activity was determined by agar tube dilution method. Test samples (400 mg/ml, DMSO) were diluted in Sabouraud dextrose agar, and allowed to solidify in slanting positions. Test fungal cultures were inoculated on the slanting position of the media in the test tubes and tubes were incubated at 29 °C for 7–10 days. After completion of the incubation period, the test tubes were observed for linear growth inhibition of fungi in mm. Percentage inhibition was calculated with reference to negative and positive controls (Paxton, 1991).

2.8. Mechanism-based yeast bioassay for DNA damaging acti6ity The assay was carried out by introducing the test

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N. Sultano6a et al. / Journal of Ethnopharmacology 78 (2001) 201–205

sample dissolved in a MeOH:DMSO (1:1) to 100 ml well in agar plates, separately impregnated with normal wild type RAD+ yeast cells and with mutant yeast cells RAD52 and incubated for 48 h at 30 °C. A clear zone of inhibition was observed around the active sample with significant activity. The result is expressed as IC12 values, which represents the concentration of the test sample in mg/ml required to produce a zone of 12 mm diameter (Gunatilaka and Kingston, 1998).

cals. These extracts were also screened against a number of pathogens to identify their antibacterial and antifungal activities. DNA damaging activities were also screened by employing mutant yeast bioassay. The structure of known compound, tamarixetin (1) was identified with the help of spectroscopic studies (EI, 1H-NMR).

3.1. Free radicals sca6enging acti6ity of T. ramosissima DPPH is a stable free radical that can accept an electron or hydrogen radical to become a stable diamagnetic molecule. Due to its odd electron, the ethanolic solution of DPPH shows a strong absorption band at 515 nm. DPPH radicals react with suitable reducing agents and then electrons become paired off and the solution loses colour stiochiometrically with the number of electrons taken up (Blois, 1958). Such reactivity has been widely used to test either the ability of compounds to act as free radical scavengers or the antioxidant activity of plant extracts (Dinis et al., 1994; Ursini et al., 1994; Lamaison et al., 1990; Navarro et al., 1993). Reduction of DPPH radicals can be observed by the decrease in absorbance at 515 nm. Different extracts of T. ramosissima reduced DPPH radicals significantly. IC50 (mg/ml) are shown in Table 1. The tannins (V) and ethylacetate (II) fractions of the plant showed low IC50 (7.4 mg/ml and 8.6 mg/ml, respectively), suggesting a high free radical scavenging activity, whereas the other fractions also showed moderate activities. The antioxidant potentials of test samples were also compared with the propyl gallate and methanolic extract of E. officinalis.

3. Results and discussions The extracts showed positive colour test with 1% aqueous FeCl3, diazotised p-nitroaniline with 20% Na2CO3 and ammonia vapour which indicated the presence of polyphenolic substances. The present study on different extracts of T. ramosissima unravelled their ability to scavenge stable DPPH free radi-

Table 1 Free radical scavenging activities of extracts by DPPH reduction Extracts

IC50 (mg/ml)a

I II III IV V E. officinalis (seeds). Standard MeOH extract having antioxidant activity Propyl gallate. Standard antioxidant

9.9 9 0.07 8.6 9 0.07 14.2 90.19 12.0 9 0.09 7.4 9 0.07 6.8 90.06 6.4 90.0003

a

IC50 is the concentration of sample which is required to scavenge 50% DPPH free radicals. IC50 are the S.E.M. of three assays.

3.2. Antibacterial acti6ity of T. ramosissima

Table 2 In vitro antibacterial activities of extracts of T. ramosissima Name of bacteria

Table 2 shows MIC of different extracts of T. ramossisima against human pathogens. Ethylacetate (II) and tannins fraction (V) exhibited antibacterial activity against C. diphtheriae (25 mg/ml) and P. mirabilis (100 mg/ml). Butanolic fraction (III) also showed activity against S. typhi (100 mg/ml) and C. diphtheriae (100 mg/ml). Tetracycline was used as a reference drug to compare the extent of activity.

MIC (mg/ml)a Extracts of T. ramosissima

C. diphtheriae B. cereus E. coli K. pneumoniae P. aeroginosa S. typhi S. boydii S. aureus S. pyogenes P. mirabilis

I

II

III

IV

V

Tetra

– – – – – – – – – –

25 – – – – – – – – 100

100 – – – – 100 – – – –

– – – – – – – – –

25 – – – – – – – – 100

12.5 – – – – 12.5 – – – 25

3.3. Antifungal acti6ity of T. ramosissima Table 3 shows that the plant extracts have some antifungal activity against a number of pathogens. Precipitates (I) and butanol (III) and ethylacetate (II) fractions showed antifungal activity at a concentration of 400 mg/ml against human pathogen, A. niger. The extent of activity was compared with standard drugs, miconazole and ketoconazole.

a Tetra, standard antibiotic tetracycline; MIC, minimum inhibitory concentration; –, inactive.

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N. Sultano6a et al. / Journal of Ethnopharmacology 78 (2001) 201–205 Table 3 In vitro antifungal activities of extracts of T. ramosissima Fungal pathogens

Linear growth (mm) inhibition% (at 400 mg/ml) Extracts of T. ramosissima

T. schoenleinii T. simii A. niger P. boydii M. phaseolina

Standard drugs

I

II

III

IV

V

Ketoconazole

Micronazole

50 25 62.5 57 –

50 66 62.5 60 –

46 47 75 60 50

25 32 33 17 –

28.5 50 25 14 –

100 100 100 100 100

100 100 100 100 100

Ketoconazole, standard drug; Miconozole, standard drug; –, inactive. Table 4 DNA damaging activities of extracts of T. ramosissima Test samples

Tamarixetin (1) I II III IV V Streptonigrin

Concentration (mg/ml)

100 100 100 100 100 100 100

IC12 (mg/ml)

Zone of inhibition (mm) S. cere6isiae RAD52

S. cere6isiae RAD+

14 9 1 – – 891 – 10 9 1 28 9 1

– – – – – 7 10

50 – – – – – 1.0

Streptonigin, standard anticancer drug; IC12, the concentration (mg/ml) is required to produce a zone of inhibition of 12 mm; –, inactive.

Its IC12 value was found to be 50 mg/ml while no significant zone of inhibition was observed for wild type yeast strain at the same concentration. This indicates specific cytotoxic activity through DNA damage. Streptonigrin, one of the potent DNA damaging anticancer drug, was used as a reference drug to compare the extent of activity (Patil et al., 1997).

Acknowledgements This work and the visit of Nurgul Sultanova to Pakistan were supported by the Ministry of Science and Technology (Government of Pakistan), under the Pak– Kazakh scientific cooperation protocol. The antibacterial bioassay was performed by Kaukub Farhana at the plant screening section of the institute.

Fig. 1.

3.4. Yeast bioassay This assay utilises DNA repair or recombinationdeficient mutants of the yeast S. cere6isiae for the screening of compounds, which induce DNA damage. This mechanism-based yeast assay depends on the different responses of DNA repair-deficient and repairproficient yeast (S. cere6isiae) strains to the sample. The major DNA repair pathway is RAD52 pathway associated with the repair of double strand break and meiotic recombination. The results are shown in Table 4. Tamarixetin (1) (Fig. 1) exhibited some toxicity towards DNA-repair deficient mutants of S. cere6isiae.

References Blois, M.S., 1958. Antioxidant determinations by the use of a stable free radical. Nature 181, 1199 –1200. Dinis, T.C.P., Madeira, M.C., Almeida, L.M., 1994. Action of phenolic derivatives (acet-aminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Archives of Biochemistry and Biophysics 315, 161–169.

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N. Sultano6a et al. / Journal of Ethnopharmacology 78 (2001) 201–205 Finegold, S.M., Martin, W.J., 1982. Antimicrobial susceptibility tests and assays. In: Bailey and Scott’s Diagnostic Microbiology, sixth ed. The CV Mosby Company, St. Louis, MO. Fujita, Y., Uehara, I., Morimoto, Y., Nakashima, M., Hatano, T., 1998. Studies on inhibition mechanism of autooxidation by tannins and flavonoids. II. Inhibition mechanism of caffee tannins isolated from leaves of Artemisia species on lipoxygenase dependent lipid peroxidation. Yakugaku Zasshi 108, 129 –135. Gunatilaka, A.A.L., Kingston, D.G.I., 1998. DNA-damaging natural products with potential anticancer activity. In: Atta-ur-Rahman (Ed.), Studies In Natural Product Chemistry 20. Elsevier, Amsterdam. Komaroz, M., 1949. Flora USSR. L. Academ. Nauk, USSR, pp. 290–321. Lamaison, J.L., Petitjean-Freytet, C., Duband, F., Carnat, A.P., 1990. Rosmarinic acid content and antioxidant activity in French Lamiaceae. Fitoterapia 62, 166 –171. Navarro, M.C., Montilla, M.P., Jimenez, J., Utrilla, M.P., 1993. Free radical scavenger and antihepatotoxic activity of Rosmarinus tomentosus. Planta Medica 59, 312 –314. Patil, A.D., Freyer, A.J., Web, R.L., Zuber, G., Reichwein, R., Bean, M.F., Faucette, L., Johnson, R.K., 1997. Pulcherrimins A –D, novel diterpene dibenzoates from Caesalpinia pulcherrima with

selective activity against DNA repair-deficient yeast mutants. Tetrahedron 53, 1583 –1592. Pavlov, N.V., 1963. Flora Kazakhastan, vol. 6. Academ. Nauk. Kaz, USSR, pp. 178–188. Paxton, J.D., 1991. Assay for antifungal activity In: Hostemann, K. (Ed.), Dey, P.M., Harborne, J.B. (series Eds.), Methods in Plant Biochemistry 6, Academic Press, Harcourt Brace Jovanovich Publishers, London. Porter, L.J., 1989. Tannins. In Harborne, J.B. (Ed.), Dey, P.M., Harborne, J.B. (series Eds.), Methods in Plant Biochemistry 1, Academic Press, Harcourt Brace Jovanovich Publishers London. Sharma, S.K., Parmar, V.S., 1998. Novel constitutes of Tamarix species. Journal of Scientific and Industrial Research 57, 873 –890. Smith, R.C., Reeves, J.C., Dage, R.C., Schnettler, R.A., 1987. Antioxidant properties of 2-imidazolones and 2-imidazolthiones. Biochemical Pharmacology 36, 1457 –1460. Sokolov, L.D., 1986. Rastitelnye USSR. L. Academ. Nauk, USSR, pp. 100 –105. Ursini, F., Maiorino, M., Morazzoni, P., Roveri, A., Pifferi, G., 1994. A novel antioxidant flavonoid (IdB 1031) affecting molecular mechanisms of cellular activation. Free Radical in Biology and Medicine 16, 547 –553.

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Chemistry of Natural Compounds, Vol. 38, No. 1, 2002

)/$9212,'62)7+($(5,$/3$572)Tamarix hispida       1$6XOWDQRYD=K$$ELORY 9%2PXUNDP]LQRYD  DQG,0&KDXGUL

UDC 547.972

Plants of the Tamarix genus (Tamaricaceae) are interesting not only for the variety of chemical compounds in them but also for their biological activity [1]. In continuation of research on Kazakh species of Tamarix [2], we isolated six pure phenolic compounds from the aerial part of T. hispida Willd. (bristle-haired tamarisk) by extraction and adsorption-distribution chromatography (silica gel, polyamide). The compounds were identified by physicochemical constants, spectra (UV, PMR, mass), and comparison with literature data. Compounds - have been previously described in certain Tamarix species [3-6] and are isolated from T. hispida for the first time. Compounds - are isolated for the first time from plants of the Tamarix genus. Furthermore, T. hispida contains the 4-sulfate of coniferylic alcohol, which we isolated previously from T. ramosissima. Various fractions of polyphenols with antioxidant, antimicrobial, and fungicidal activity were obtained. ′7HWUDK\GUR[\PHWKR[\IODYRQHLVRUKDPQHWLQ  , mp 304-306°C; PMR (500 MHz, C5D5N, δ, ppm, J/Hz): 8.53 (1H, d, J = 2, H-2′), 8.13 (1H, dd, J1 = 2, J2 = 8, H-6′), 7.12 (1H, d, J = 8, H-5′), 6.78 (1H, d, J = 2, H-8), 6.73 (1H, d, J = 2, H-6), 3.90 (3H, s, OCH3). Mass spectrum (EI, 70 eV), m/z: 316 [M]+, C16H12O7 [3]. 'LK\GUR[\′GLPHWKR[\IODYRQH , mp 180-182°C, PMR (500 MHz, C5D5N, δ, ppm, J/Hz): 8.52 (2H, d, J = 9, H-2′, H-6′), 7.16 (2H, d, J = 9.0, H-3′, H-5′), 6.70 (1H, d, J = 2, H-8), 6.58 (1H, d, J = 2, H-6), 3.76, 3.74 (6H, s, OCH3). Mass spectrum (EI, 70 eV), m/z: 314 [M]+, C17H14O6 [4]. ′7ULK\GUR[\PHWKR[\IODYRQHUKDPQRFLWULQ  , mp 223-225°C, UV spectrum (MeOH, λmax, nm): 267, 364; +NaOMe: dec.; +AlCl3: 270, 423; +AlCl3/HCl: 270, 423; +CH3COONa: 267, 364; +CH3COONa+H3BO3: 268, 363. PMR (500 MHz, C5D5N, δ, ppm, J/Hz): 8.05 (2H, d, J = 10, H-2′, H-6′), 6.92 (2H, d, J = 10, H-3′, H-5′), 6.31 (1H, d, J = 2, H-8), 6.15 (1H, d, J = 2, H-6), 3.76 (3H, s, OCH3). Mass spectrum (EI, 70 eV), m/z: 300 [M]+, C16H12O6 [5]. ′7ULK\GUR[\IODYRQH2α/UKDPQRS\UDQRVLGHDI]HOLQ  , mp 168-170°C, UV spectrum (MeOH, λmax, nm): 265, 340; +NaOMe: 272, 390; +AlCl3: 273, 347 sh, 389; +AlCl3/HCl: 274, 347 sh, 389; +CH3COONa: 265, 344; +CH3COONa+H3BO3: 265, 340. PMR (500 MHZ, CD3OD, δ, ppm, J/Hz): 7.79 (2H, d, J = 8.8, H-2′, H-6′), 6.95 (2H, d, J = 8.8, H-3′, H-5′), 6.38 (1H, d, J = 2, H-8), 6.21 (1H, d, J = 2, H-6), 5.37 (1H, d, J = 2.0, H-1″), 0.92 (3H, d, J = 6, CH3). Mass spectrum (EI, 70 eV), m/z: 431 [M - H]+, C21H20O10 [7]. ′'LK\GUR[\′GLPHWKR[\IODYRQH2β'JOXFRS\UDQRVLGH , mp 160-162°C, UV spectrum (MeOH, λmax, nm): 269, 348; +NaOMe: 269, 343; +AlCl3: 295, 307, 360; +AlCl3/HCl: 360, 302, 292; +CH3COONa: 271, 348; +CH3COONa+H3BO3: 268, 344. PMR (400 MHz, CD3OD, δ, ppm, J/Hz): 7.97 (1H, d, J = 2, H-2′), 7.76 (1H, dd, J1 = 2, J2 = 8, H-6′), 7.05 (1H, d, J = 8, H-5′), 6.35 (1H, d, J = 2, H-8), 6.20 (1H, d, J = 2, H-6), 5.40 (1H, d, J = 7, H-1″), 3.90, 3.95 (6H, s, OCH3), C23H24O12 [8]. +\GUR[\2GLPHWK\OEHQ]RLFDFLGV\ULQJLFDFLG  , mp 208-210°C, PMR (500 MHz, CD3OD, /, ppm, J/Hz): 7.01 (2H, s, H-2, H-6), 3.84, 3.82 (6H, s, OCH3). Mass spectrum (EI, 70 eV), m/z: 198 [M]+, C9H10O5 [9].

5()(5(1&(6 1.

S. K. Sharma and V. S. Parmar, J. Sci. Ind. Res., , 873 (1998).

1) Al′-Farabi Kazakh National University, Almaty, ul. Karasai Batyra, 95a, fax (007) 3272 74 26 09, [email protected]; 2) Scientific Research Institute of Chemistry (H. E. J.), Karachi University, Pakistan. Translated from Khimiya Prirodnykh Soedinenii, No. 1, p. 80, January-February, 2002. Original article submitted December 3, 2001. 0009-3130/02/3801-0098$27.00 © 2002 Plenum Publishing Corporation

35

2. 3. 4. 5. 6. 7. 8. 9.

N. A. Sultanova, E. A. Krizhevskaya, V. B. Omurkamzinova, and Zh. A. Abilov, Vestn. Kaz. Gos. Univ., , No. 4, 5 (1999). A. K. Noor, M. Kamil, and M. Ilyas, Indian J. Chem., Sect. B, , 390 (1979). H. J. E. Sissi, M. A. M. Nawwar, and N. A. M. Saleh, Experientia, , No. 9, 1064 (1973). M. A. M. Nawwar, A. E. A. Sherbeiny, and M. A. E. Ansari, Experientia, , 1118 (1975). Plant Resources of the USSR. Flowering Plants, Their Chemical Composition and Use. Paeoniaceae—Thymelaeaceae Families [in Russian], Nauka, Leningrad (1986). V. Manju, R. S. Varma, and M. R. Parthasarathy, Z. Naturforsch. C: Biosci., , No. 3-4, 344 (1980). Chem. Abstr., , 251207j (1994). S. S. N. Murthy, N. S. P. Rao, and A. S. R. Anjaneyulu, Curr. Sci., , 341 (1974).

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Chemistry of Natural Compounds, Vol. 40, No. 3, 2004

)/$9212,'62)3/$176)5207+(*(186Tamarix $.8PEHWRYD6K=K(VLUNHJHQRYD,0&KDXGUL 9%2PXUNDP]LQRYDDQG=K$$ELORY

UDC 547.972

In continuation of studies of plants of the genus Tamarix [1], we investigated the aerial part of T. elongata Ledeb, a species endemic to Central Asia, and T. laxa Willd. The plants were gathered in Aralsk (dried bottom of the Aral Sea, INTAS program) and Almaty districts during the growth phase. Phytochemical analytical methods for T. elongata and T. laxa determined oxidized forms of flavonoids (1.42 and 0.92%, respectively), hydrolyzed tanning agents (8.10 and 8.40), phenolic (1.76 and 3.36) and amino acids (0.54 and 1.98), and carbohydrates (0.15 and 0.14). Fractional extraction, adsorption-distribution, and gel chromatography isolated pure -, where - were from both species whereas - were from T. elongata. Chemical (acid hydrolysis, alkaline destruction, anthocyanidine sample) and spectral methods (UV, mass, PMR spectroscopies) and comparison with the literature and authentic samples isolated from T. hispida and T. ramosissima [1] identified - as quercetin (), isorhamnetin (), tamarixetin (), and potassium tamarixetin 3-O-sulfate (). Chrysoeriol (), rhamnazin (), and tamarixetin 3-O-α-L-arabinoside () were isolated from plants of the genus Tamarix for the first time. Furthermore, T. elongata afforded tamarixetin 3-O-β-D-glucoside (), which was previously observed in T. nilotica [2]. The glycosidic nature of  and  was determined from acid hydrolysis, as a result of which the aglycon tamarixetin () was isolated. L-Arabinose and D-glucose were identified in the hydrolysates. The attachment site of the carbohydrates was established using UV spectroscopy with complexants and ionizing reagents. &KU\VRHULRO  (5,7,4′-trihydroxy-3′-methoxyflavone), mp 330-332°C (70% ethanol); UV spectrum (MeOH, λmax, nm): 254, 354; +CH3COONa: 260, 380; +CH3COONa + H3BO3: 260, 353; +NaOMe: 275, 405; +AlCl3: 280, 402; +AlCl3/HCl: 270, 385. PMR spectrum (200 MHz, DMSO-d6, δ, ppm, J/Hz): 3.70 (3H, s, OCH3), 6.20 (1H, d, J = 2.0, H-6), 6.40 (1H, d, J = 2.0, H-8), 6.70 (1H, s, H-3), 6.90 (1H, d, J = 8.0, H-5′), 7.47 (2H, dd, J = 8.0 and J = 2.0, H-2′, H-6′). Mass spectrum (EI, 70 eV, m/z): 300, C16H12O6 [3]. 5KDPQD]LQ (3,5,4′-trihydroxy-7,3′-dimethoxyflavone), mp 222-224°C (70% ethanol); UV spectrum (MeOH, λmax, nm): 254, 368; +CH3COONa: 255, 369; +CH3COONa + H3BO3: 255, 367; +NaOMe: 266, 388; +AlCl3: 267, 426; +AlCl3/HCl: 267, 426. PMR spectrum (400 MHz, CD3OD, δ, ppm, J/Hz): 3.92 (6H, s, OCH3), 6.17 (1H, d, J = 2.0, H-6), 6.38 (1H, d, J = 2.0, H-8), 7.05 (1H, d, J = 8.5, H-5′), 7.72 (1H, dd, J = 8.4 and J = 2.0, H-6′), 7.74 (1H, d, J = 2.0, H-2′). Mass spectrum (EI, 70 eV, m/z): 330; C17H14O7 [4]. 7DPDUL[HWLQ2α/DUDELQRVLGH , C21H20O11, mp 200-202°C (70% ethanol); UV spectrum (MeOH, λmax, nm): 254, 348; +CH3COONa: 270, 356; +CH3COONa + H3BO3: 255, 353; +NaOMe: 273, 379; +AlCl3: 274, 397; +AlCl3/HCl: 276, 396. PMR spectrum (500 MHz, CD3OD, δ, ppm, J/Hz): 3.92 (3H, s, OCH3), 3.67-4.21 (arabinose protons), 4.56 (1H, d, J = 2.0, H-1″), 6.19 (1H, d, J = 2.0, H-6), 6.40 (1H, d, J = 2.0, H-8), 7.02 (1H, d, J = 8.6, H-5′), 7.63 (1H, d, J = 2.0, H-2′), 7.77 (1H, dd, J = 8.0 and J = 2.0, H-6′). Mass spectrum of aglycon (EI, 70 eV, m/z): 316; C16H17O7 [5].

1) Al-Farabi Kazakh National University, Almaty, ul. Karasai batyra, 95a, fax (3272) 92 37 31, e-mail: [email protected]; 2) Scientific-Research Institute of Chemistry, (H. E. J.) University, Karachi, Pakistan. Translated from Khimiya Prirodnykh Soedinenii, No. 3, p. 250, May-June, 2004. Original article submitted April 12, 2004. 0009-3130/04/4003-0297 ©2004 Plenum Publishing Corporation

37

7DPDUL[HWLQ2β'JOXFRVLGH , C22H22O12, mp 218-220°C (70% ethanol); UV spectrum (MeOH, λmax, nm): 267, 348; +CH3COONa: 269, 354; +CH3COONa + H3BO3: 267, 351; +NaOMe: 272, 388; +AlCl3: 269, 397; +AlCl3/HCl: 275, 396. PMR spectrum (400 MHz, C5D5N, δ, ppm, J/Hz): 3.59 (3H, s, OCH3), 3.49-3.85 (glucose protons), 4.07 (1H, d, J = 6.70, H-1″), 6.54 (1H, d, J = 2.0, H-6), 6.60 (1H, d, J = 2.0, H-8), 6.99 (1H, d, J = 8.6, H-5′), 8.39 (1H, d, J = 2.0, H-2′), 8.48 (1H, dd, J = 8.0 and J = 2.0, H-6′). Mass spectrum of aglycon (EI, 70 eV, m/z): 316; C16H12O7.

5()(5(1&(6 1. 2. 3. 4. 5.

N. A. Sultanova, Zh. A. Abilov, V. B. Omurkamzinova, and I. M. Chaudri, Khim. Prir. Soedin., 80 (2002). M. S. Ishak, H. I. El Sissi, A. E. A. El Sherbieny, and M. A. M. Nawwar, Planta Med., , 374 (1972). A. Malik and M. P. Yuldashev, Khim. Prir. Soedin., 83 (2002). T. K. Chumbalov, T. N. Bikbulatova, M. I. Ilyasova, and R. M. Mukhamedieva, Khim. Prir. Soedin., 282 (1975). L. E. Urbatsch and T. J. Mabry, Phytochemistry, , 278 (1974).

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Chemistry of Natural Compounds, Vol. 40, No. 1, 2004

%,2/2*,&$//