Biodiscrimination of alpha-tocopherol stereoisomers during intestinal absorption.

Synthetic alpha-tocopherol (alpha-Toc) contains equal amounts of eight different stereoisomers, and the four stereoisomers with the 2R configuration are generally more active than their corresponding 2S-isomers. We investigated the biodiscrimination of alpha-Toc stereoisomers during intestinal absorption in situ and in vitro. Intestinal absorption of alpha-Toc stereoisomers was examined in situ in vitamin E-deficient rats with cannulated thoracic ducts. We found that the ratios of alpha-Toc stereoisomers in lymph of the all-rac-alpha-Toc group were the same as the administered alpha-Toc stereoisomers, and 2R-isomers occupied approximately 50% of absorbed alpha-Toc. The uptake of alpha-Toc stereoisomers also was measured using Caco-2 cells cultured on filter membranes. The concentration of RRR-alpha-Toc in Caco-2 cells was not significantly different from that of SRR-alpha-Toc. Therefore, the discrimination of alpha-Toc stereoisomers does not occur during absorption in small intestine, suggesting the liver as source for the biodiscrimination.