The Chemistry and Biological Activity of Some Derivatives of Alpha-Tocopherol

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The Chemistry and Biological Activity of Some Derivatives of Alpha-Tocopherol

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TO m m m m m

m m m $ & m n n n of $ m w m w t m or'a^eM m m M

lay AUee feaMeridea

A dissertation submitted la p a rtia l fulfillm ent of the requirements fo r the degree of Doctor of Philosophy, in the Department of Biochemistry in the Graduate College of the State University of lovra June, 19$0

ProQuest Number: 10666173

All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is d e p e n d e n t upon the quality o f the c o p y submitted. In th e unlikely ev en t that the author did not send a co m p lete manuscript and there are missing p a g es, th ese will b e noted. Also, if material had to b e rem oved, a n ote will indicate the deletion.

uest, ProQuest 10666173 Published by ProQuest LLC (2017). Copyright o f th e Dissertation is held by th e Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States C o d e Microform Edition © ProQuest LLC. ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 48106 - 1346

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ACKHOttftEBGMEIIf fho author wishes to express her sincere appreciation to Br* H» A* M attiil fh rh io in te re st an# help* I t has bean a pleasure working with him* She also wishes to thank Dr. R. I*. Sbriner fo r Mo ooioahio suggestions and for the use of substances and apparatus of the Organic BOpartment*

to t s i f t and Bospany she is greatly

indebted for the fellowship under which th is work was dono«

TABUS OP 0Q8TBBTS P«8*

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..................... . . .. ...................

ism

oh f t- T o o a m B m s m B

* — ■*«■■*» « •

x

................

?

••■...

a

OUSATIOS OP *-TOOOPHEaOl WIffl KKnOj^............................

12

H£OLOQICAl> ACTIVITI OP *»TOCOPBESTLHlDROQOIHOKE . . . . . .

XU

BxnmoarrAX.

U

sw m a rt APPSNDIX

............................... ..................................

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21 22

BIBLIOGBAPHT......................................

111

26

TABLE W MWM. fatel#'

page

I

Bioaaaay* * ♦ ♦ ♦ * * * * * * . • * * # * * * * # # #

31

XX

Bioa»«asni * ■* * * * * « * « « * * + * * * * » « * #

It

III

If? Absorption Spectra ♦ . « • * « .* * * » « * * * *

II

iv

I

INTRODUCTION Vitamin 1 was f i r s t known as a naturally securing a n tl©xidant inhibiting the formation of f a t peroxides in v itro and as the fat-soluble vitamin which prevents fo ctal resorption in female rats and dogsneration of germinal epithelium in male rats*

I ts absence

from the d ie t has also boon related to muscular dystrophy in rabbits, encephalo&alaeia In chicks and a groat variety of abnormalities in 1 various species of animals as described in many reviews* there are several forms of vitamin $ which are named tocopherols.

They are chroman derivatives differing in the number

and positions of without

groups In the bsnsenoid nucleus. The compound

groups is named taeol* and i t has three asymmetric G

atoms*

S'

H

The different ferns securing in nature a m J^0>o


"Vitamin B„« W. (1,38),

th® m

« w » 'i

fniversiiar #£ 0aM£s$tti«* ?ol*I*% $%!»

io < m « if» iiin ip ( ii Hint ■iim nma n * . * m m m .

*

B. B laisei, aad W. i* t« , 8atu*wisa*

ttW larger* P.* /and^eigerj .A** ffel»*.0hW lata** 23* "WS* (19h0). ~" tf^ Io£lar* %»i Hely. Ohim. Acta** 30* 100* (111*7)30* Sanson* W. S.* Bireotiona for the ttea of the ia d ified Menaies**

Wright su w. .

.

iii83L^oar'~

31*. Swletoslavakl, W** Bbullioacopic Measurements* Beinhold Publishing 0®rp?, 19b5*

31

f mm

%

m om m Compound* Indicated l ir a Given Orally

Compound

w #

Dbmmia Poe# Big# in mg a F W E F

10

0 0 2 6 3 1

3

0

3 It

1

♦ $

•a *

U Ls ?

T

1 2

5 3 2 0 0 1 i i

Adj. Total fe ta l lit t e r , X lit t e r E fficiency Foe* Beg. B ffic.0

O

0 30 100 100 0 0 7$

m

0 0 3 8

n

12 0 t

U

6 3 1 1 1

9 6

0 0

h0*0 89.0 91#S 92.0 0 5M 66* S T7.0

3

10

8 10

Uo

60 80

0 0 0 0 2

1 2 1 1 0

0 0 0 0 300

0 0 0 0 2

2 1 0

0 0 0 0 100

Tocophoiylquincne 20

0

3

0

0

3

0

Bed o-quinoae

atfQPt

12 20

ii

3 5 b

Product isolated a fte r the action of Hj POjl on a methanol solution of toeopherylquinone•

6 . Adjusted l i t t e r e fficien cy #

38

tm s ir BX0ASSAI3 CoopoondB Indicated were Given Intravenously

Compound

a^tocopherylhydroquinono

Dose Fob. Nag. in mg

o .w

o

a

0

0

17

0

0 3.00 0 3.ao 0 15.00 o 20.00 0

h

0

0

15

0

5

0

0

11

0

%

0

0

6

0

%

0

h

0

%

0

0 0

Z

0

0 .5 0

Z

Q

100

Z

0

100

0.T0

z

0

100

k

0

100

1.00

7

0

100

xi

0

100

1.50

Z

0

100

13

0

100

&*k0

a-dl-etocopherol

Adj. t M tter fe ta l fe ta l l i t t e r Efficiency Fas. Keg. I f f ie .

II ta b s m m absorption sksctsa

i