Vitamin E natural compounds

Alpha-Tocopherol a.k.a. Vitamin E

 Vitamin E
• Vitamin E is a famil of a-, b-, g-, d- tocopherols and
corresponding tocotrienols izomers.
• They are formed from chroman ring and hydrofobic
fytyl side chain.
• The highest biological activity has a-tokoferol.
 Vitamin E as an antioxidant
R1 R + TOH  RH + TO
HO
CH 3
Phythyl Tail .O CH 3 CH 3
R2 O
R3 (CH 2 )3 CH (CH 2 )3 CH (CH 2 )3 CH (CH 3 )2
CH 3 O CH 3
Chromane Head
CH 3

R1 R2 R3
a CH 3 CH 3 CH 3
b CH 3 H CH 3
g H CH 3 CH 3
d H H CH 3
 Vitamin E as antioxidant
• Stops free radical reactions (peroxyl radicals ROO , oxygen radicals
HO, lipoperoxid radicals LOO). Chroman ring with OH group →
uptake radicals.
Vitamin E Function

Free
radicals Quenched
Oxidative radical
damage
 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
 E-Facts
• Plays a role in immune function, DNA repair, other
metabolic processes, and in protecting other
antioxidants

• U.S. RDA : 15 mg (22.5 IU) per day

• Typical Western diet provides 14 mg (21 IU) of Vit E

• Upper allowable intake (prior to Meta-Analysis):

1000mg (1500 IU)
 2005 Annals of Int Med: “Meta-Analysis:
High-Dosage Vitamin E Supplementation
May Increase All-Cause Mortality”
• Three previous meta-analyses that did
not consider the dose-dependent effect
of vitamin E concluded that vitamin E
was neither beneficial nor harmful.

• New Conclusion based on 19

randomized controlled trials: High-
dosage (>=400 IU/d) vitamin E
supplements may increase all-cause
mortality and should be avoided.
 Health Hopes of Vitamin E
• Heart Disease: Mixed results

• Cancer: Promising but not conclusive

– Breast cancer: two opposing studies
– Colon and G.I. cancer: probably no benefit
– Prostate and bladder cancer: possible benefit

• Alzheimer’s: theoretical but not well studied

 Vitamin E & Cataracts
• 1998: “Antioxidant vitamins and nuclear opacities:
the longitudinal study of cataract”
– Cataract risk reduced by ½ in Vit E supplement users
– 764 participant observational study (low significance)

However,

• 1997: “Long-term supplementation with alpha-

tocopherol and beta-carotene and age-related
cataract”
– No benefit to Middle-aged male smokers taking vitamin
E supplements on the incidence of cataract formation