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.
Miyamoto
S
S
National Food Research Institute, Ministry of Agriculture, Forestry and Fisheries, Ibaraki, Japan.
Koga
T
T
Terao
J
J
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis*; D001409:Bacillus cereus / Q000201:enzymology; D001921:Brain / Q000378:metabolism; D002839:Chromans / Q000737:chemistry*; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D005395:Fish Oils / Q000737:chemistry; D016166:Free Radical Scavengers / Q000138:chemical synthesis; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D010755:Organophosphates / Q000138:chemical synthesis*; D051381:Rats; D013056:Spectrophotometry, Ultraviolet; D010738:Type C Phospholipases / Q000737:chemistry; D014810:Vitamin E / Q000031:analogs & derivatives*