Tocopherol (Vitamin E)

in Health and disease

Tocopherol (Vitamin E) in Health and disease

Vitamin E is an essential fat-soluble vitamin.
Recently, the National Academy of Sciences defined vitamin E
as the 2R stereoisomers of alpha-tocopherol.
However, past classifications of vitamin E included a group of
eight compounds alpha-, beta-, gamma- and deltatocopherols and tocotrienols.
The naturally occurring d-alpha-tocopherol has the highest
biological activity.

Chemical Structure
Classification
Number
And
Position
Methyl groups
On
Chroman Ring

Chemical Structure

- tocopherols
- tocopherols
- tocopherols
tocopherols
- tocotrienols
- tocotrienols
- tocotrienols
tocotrienols
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Chemical Structure
tocopherols

Most Active
Most Potent
The Highest
Bioavaibility
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Sources, Intakes and Requirements

Vegetable oils, sunflower seeds and nuts are the
richest dietary sources
Average daily intake is 15 I.U. in men and 11.4 I.U in
women (NHANES III)
DRI and RDA is 15 mg alpha-tocopherol (22.5 I.U.)
Optimal vitamin E intakes may be 100-400 I.U. per
day

Absorption and Transport

Dependent on ability to absorb fat

Absorbed into lymphatic system
Component of chylomicrons
Alpha-tocopherol is major tocopherol in plasma
Positive association between serum lipid and
tocopherol levels
Normal range is 0.5-1.6 mg/dl

Functions of Vitamin E

Chain-breaking antioxidant
Protects cell membranes
Enhances immune response
Regulates platelet aggregation decrease PG
production
Regulates protein kinase C activation

Functions
Vitamin E in the form of d-alpha-tocopherol is an important fatsoluble antioxidant, scavenging radical before these radicals can
do further harm to cells.
Free radicals are very reactive atoms or molecules that typically
possess a single unpaired electron :
oxygen free radicals,
lipid peroxy radicals and
singlet oxygen molecules.
New studies have revealed that the tocotrienol forms of vitamin
E are even more potent antioxidants than the tocopherol
isomers.

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Functions
Vitamin E helps maintain the structural integrity of cell
membranes throughout the body.

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Antioxidant

The antioxidant
neutralizes a free radical
by donating an electron.

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An antioxidant is a chemical so easily

oxidized itself that it protects others from oxidation.

OH
and / or

Double Bond
eg. Vitamin A

Phenol
eg. Vitamin E or C
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Free Radicals - the Metabolic Oxidizers

Free radical = unpaired electron very reactive

OH

OH

OH

OH

Oxygen radicals: Hydroxy (HO) / Peroxy (HOO)

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Vitamin E as an antioxidant
R + TOH RH + TO

R1
HO
R2

Phythyl Tail

.O

CH 3
CH 3

CH 3

(CH 2 )3 CH(CH 2 )3 CH(CH 2 )3 CH(CH 3 )2

R3
CH 3

Chromane Head

CH 3

CH 3

R1
CH 3

R2
CH 3

R3
CH 3

CH 3

CH 3

CH 3

CH 3

CH 3

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Efficacy of Natural-Source vs Synthetic

Vitamin E
Natural-source is a single isomer
(d-alpha-tocopherol)
Synthetic is a mixture of eight isomers
Natural-source has twice the bioavailability of
synthetic

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Protective Role in Disease Prevention

There is extensive evidence implicating oxidative
damage in the development of degenerative
diseases and conditions. A number of studies
have evaluated the role of vitamin E, alone or in
combination with other antioxidants, in
preventing or minimizing oxidative damage
associated with development of cancer, coronary
heart disease, cataracts and Alzheimers disease.

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Coronary Heart Disease

Increased vitamin E intakes associated with
decreased risk of coronary heart disease in
epidemiologic studies
Dose-dependent resistance of LDL to oxidation with
vitamin E supplementation
In 2 of 3 secondary prevention trials, vitamin E
showed protective effects
d-alpha-tocopherol has been shown to inhibit the
"clumping" of blood platelets (thus helping to avoid
blood clots) and enhancing vasodilation (the
opening of blood vessels).
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 vitamin E improved the activity of

endothelium-derived nitric oxide,
vitamin E improved endothelial function in
part due to the inhibition of protein kinase C
(PKC) stimulation.
vitamin E inhibited platelet aggregation in part
through a mechanism that involves PKC.

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Cataracts
Vitamin E delayed or minimized cataract
development in animal models
Epidemiologic data suggest a relationship between
blood vitamin E levels and cataract risk
Decreased cataract risk associated with vitamin E
supplementation

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Cancer
Majority of epidemiologic studies showed an inverse
association between vitamin E status and subsequent risk
of certain cancers
Intervention trials have shown mixed results
Reduced cancer incidence and decreased mortality rate from
stomach and esophageal cancers in China
No decrease in recurring colorectal tumors in U.S.
Improvement in precancerous oral lesions in U.S.
Decreased incidence and mortality of prostate cancer but not lung
cancer in Finland

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Safety
Few side effects in double-blind, controlled
human studies
Could affect blood clotting in patients on blood
thinners
No other specific side effects
UL set at 1,000 mg per day for adults
Vitamin E is safe and well tolerated over wide
range of intakes and time periods

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The symptoms of Vitamin E deficiency

Muscle weakness
lethargy
apathy
a lack of vitality
indigestion
muscle cramps
inability to concentrate
irritability
disinterest in physical
activity
red blood cell breakage
anemia
neurological problems

An increasing body of
evidence is emerging to
implicate free radical
activity in the
pathogenesis of
periodontal breakdown.
Inadequate antioxidant
availability could either
predispose the host to the
disease, or modify the
progression of a preexisting disease.
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Terima Kasih

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