Synthesis of a novel phosphate ester of a vitamin E derivative and its antioxidative activity

A novel phosphate ester containing a chromanol structure was synthesized from 1,2-diacyl-sn-glycero-3-phospho-2'-hydroxyethyl-2',5',7',8'-tetramethyl- 6' -hydroxychroman (PCh) by hydrolysis catalyzed by phospholipase C from Bacillus cereus. The structure of the product was found by spectral analyses to be 2-(2',5',7',8'-tetramethyl-6'-hydroxychromanyl)ethylphosphate++ + (Ch-P). Ch-P was highly soluble in the aqueous phase at neutral pH values and exerted higher antioxidative activity than alpha-tocopherol and PCh in the Fe(III)/ascorbic acid-catalyzed peroxidation of a fish oil emulsion and the autoxidation of a rat brain homogenate.