ALPHA-TOCOPHEROL OXIDATION MEDIATED BY SUPEROXIDE ANION (O-2-) .2. IDENTIFICATION OF THE STABLE ALPHA-TOCOPHEROL OXIDATION-PRODUCTS

被引:16
作者
HA, YL [1 ]
CSALLANY, AS [1 ]
机构
[1] UNIV MINNESOTA,DEPT FOOD SCI & NUTR,ST PAUL,MN 55108
关键词
D O I
10.1007/BF02536179
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The present paper describes the identification of two stable end products of alpha-tocopherol oxidation that were previously detected among the products of the reaction of alpha-tocopherol with superoxide anion (O2-) under aprotic conditions. One compound, previously designated compound A, was identified as trans-7-hydroxy-trans-8,8a-epoxy-alpha-tocopherone, and the other, designated compound B, was identified as cis-7-hydroxy-cis-8,8a-epoxy-alpha-tocopherone. It was also observed that under protic conditions (10% water in acetonitrile) the reaction of alpha-tocopherol with O2- did not produce compounds A and B, but rather alpha-tocopheryl quinone, alpha-tocopherol dimer, alpha-tocopherol dihydroxy dimer, and the previously designated compound C. Compound C was identified in the present study as alpha-tocopheryl-quinone-2,3-epoxide.
引用
收藏
页码:201 / 205
页数:5
相关论文
共 25 条
[1]   CHEMISTRY OF SINGLET OXYGEN .30. UNSTABLE PRIMARY PRODUCT OF TOCOPHEROL PHOTO-OXIDATION [J].
CLOUGH, RL ;
YEE, BG ;
FOOTE, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (03) :683-686
[2]  
CSALLANY A S, 1970, Lipids, V5, P63, DOI 10.1007/BF02531096
[3]   ALPHA-TOCOPHEROL OXIDATION MEDIATED BY SUPEROXIDE ANION (O-2-) .1. REACTIONS IN APROTIC AND PROTIC CONDITIONS [J].
CSALLANY, AS ;
HA, YL .
LIPIDS, 1992, 27 (03) :195-200
[4]  
Fee J. A., 1980, BIOL CLIN ASPECTS SU, P41
[5]   SUPEROXIDE DISMUTASES [J].
FRIDOVICH, I .
ANNUAL REVIEW OF BIOCHEMISTRY, 1975, 44 :147-159
[6]   OXIDATION OF ALPHA-TOCOPHEROL IN MICELLES AND LIPOSOMES BY THE HYDROXYL, PERHYDROXYL, AND SUPEROXIDE FREE-RADICALS [J].
FUKUZAWA, K ;
GEBICKI, JM .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1983, 226 (01) :242-251
[7]  
GIBIAN M, 1979, J AM CHEM SOC, V101, P1292
[8]   SENSITIZED PHOTOOXIDATION OF ALPHA-TOCOPHEROL AND OF 2,2,5,7,8-PENTAMETHYL-6-CHROMANOL IN ETHYL ACETATE [J].
GRAMS, GW ;
INGLETT, GE .
LIPIDS, 1972, 7 (07) :442-&
[9]   DYE-SENSITIZED PHOTOOXIDATION OF ALPHA-TOCOPHEROL [J].
GRAMS, GW ;
INGLETT, GE ;
ESKINS, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (03) :866-&
[10]   DYE-SENSITIZED PHOTOOXIDATION OF TOCOPHEROLS - CORRELATION BETWEEN SINGLET OXYGEN REACTIVITY AND VITAMIN-E ACTIVITY [J].
GRAMS, GW ;
ESKINS, K .
BIOCHEMISTRY, 1972, 11 (04) :606-&