Synthesis of a Novel Phosphate Ester of a Vitamin E Derivative and Its Antioxidative Activity

Abstract

  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′-hydro-xychroman (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 α-tocopherol and PCh in the Fe(III)/ascorbic acid-catalyzed peroxidation of a fish oil emulsion and the autoxidation of a rat brain homogenate.