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Review
. 2008 Oct-Dec;1(4):376-82.

So many options but one choice: the human body prefers alpha-tocopherol. A matter of stereochemistry

B Manolescu  1 , V Atanasiu, C Cercasov, I Stoian, E Oprea, C Buşu
Affiliations
Review

So many options but one choice: the human body prefers alpha-tocopherol. A matter of stereochemistry

B Manolescu et al. J Med Life. 2008 Oct-Dec.

Abstract

alpha-Tocopherol belongs to the group of vitamin E vitamers. Recent years findings indicate that alpha-tocopherol is more than just a simple fat-soluble anti-oxidant as it was found that it can also regulate gene expression. From all vitamin E vitamers human body preferentially retains alpha-tocopherol, but the reasons for this preference are still elusive. Different studies indicated that human body, through the action of two hepatic proteins, alpha-tocopherol transfer protein (alpha-TTP) and cytochrome P450 4F2 (CYP4F2), is able to make subtle structural differences between different vitamin E forms. This is an example of stereochemistry used as a discrimination factor between molecules with different biological activities.

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Figures

Fig. 1
Fig. 1
Chemical structures of tocopherols and tocotrienols. The circles mark the three chiral centers in tocopherols (2, 4’, 8’).
Fig. 2
Fig. 2
α-Tocopherol acting as a chain-breaking anti-oxidant.
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See this image and copyright information in PMC

References

    1. Cercasov C, Manolescu B. Biochemical and therapeutical aspects of vitamin E. Rev. Roum. Chim. 2005;50(6):419–432.
    1. Weiser H, Vecchi H. Stereoisomers of alpha-tocopheryl acetate. II. Biopotencies of all eight stereoisomers, individually or in mixtures, as determined by rat resorption-gestation tests. Int. J. Vitam. Nutr. Res. 1982;52(3):351–370. - PubMed
    1. Weiser H, Riss G, Kormann AW. Biodiscrimination of the eight α-tocopherol stereoisomers results in preferential accumulation of the four 2R forms in tissues and plasma of rats. J. Nutr. 1996;126:2539–2549. - PubMed
    1. Brigelius-Flohe R, Traber MG. Vitamin E: function and metabolism. FASEB J. 1999;13:1145–1155. - PubMed
    1. Azzi A, Zingg J-M. Vitamin E: textbooks require updating. Biochem. Mol. Biol. Educat. 2005;33(3):184–187. - PubMed

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