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

Biosci Biotechnol Biochem. 1998 Dec;62(12):2463-6. doi: 10.1271/bbb.62.2463.

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' -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.

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis*
  • Bacillus cereus / enzymology
  • Brain / metabolism
  • Chromans / chemistry*
  • Chromatography, Gas
  • Chromatography, High Pressure Liquid
  • Fish Oils / chemistry
  • Free Radical Scavengers / chemical synthesis
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Male
  • Organophosphates / chemical synthesis*
  • Rats
  • Spectrophotometry, Ultraviolet
  • Type C Phospholipases / chemistry
  • Vitamin E / analogs & derivatives*

Substances

  • Antioxidants
  • Chromans
  • Fish Oils
  • Free Radical Scavengers
  • Organophosphates
  • Vitamin E
  • Type C Phospholipases