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
T ^O ^ T.%lo JL /
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*
tsmmmaa a stx o s o r
..................... . . .. ...................
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
............................... ..................................
..................
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