Journal of animal physiology and animal nutrition

Utilization of stereoisomers from alpha-tocopherol in livestock animals.

PMID 19663978


Alpha-tocopherol derived from natural source is a single stereoisomer (i.e. RRR-alpha-tocopherol), whereas synthetic alpha-tocopherol consists of a mixture of eight stereoisomers, including RRR-, RRS-, RSR-, RSS-alpha-tocopherol (the 2R isomers, R configuration at positions 2' of the phytyl tail) and SRR-, SSR-, SRS- and SSS-alpha-tocopherol (the 2S isomers, S configuration at positions 2' of the phytyl tail). R and S are assigned by the sequence-rule procedure, i.e. the priorities of the substituents decrease in clockwise direction or anti-clockwise direction at each chiral centre. Not all these stereoisomers are equally bio-available, which can be explained by the differences in the rate of degradation, transportation and retention. Humans and livestock animals can only utilize the 2R forms, while the 2S forms have very low bio-availability or basically are not bio-available. The utilization of 2R forms differs between different animal species. For humans and livestock animals, RRR-alpha-tocopherol has the highest bio-availability compared with other stereoisomers, while other 2R forms have lower bio-availability compared with RRR-alpha-tocopherol. The relative bio-availability of RRR- and all-rac-alpha-tocopherol is related to animal species, ages of animals and assessment criteria. In general, recent literature studies have demonstrated that the relative bioavailability of RRR- and all-rac-alpha-tocopherol is 2:1, differing from the commonly used conversion factor of 1.36:1. The latter was based on rat-resorption-gestation test. Most recent studies have shown that this conversion factor of 1.36:1 is not applicable to livestock animals and based on other metabolic functions. When IU is required to express vitamin E activity, new conversion factors need to be defined for livestock animals. Quantitative determination of bio-availability of the individual alpha-tocopherol stereoisomers will give a more detailed picture of the bioavailability of natural and synthetic vitamin E forms.