Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants

被引:56
作者
Boots, AW [1 ]
Haenen, GRMM [1 ]
den Hartog, GJM [1 ]
Bast, A [1 ]
机构
[1] Maastricht Univ, Fac Med, Dept Pharmacol & Toxicol, NL-6200 MD Maastricht, Netherlands
来源
BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS | 2002年 / 1583卷 / 03期
关键词
catechol; antioxidant; lipid peroxidation; semiquinone radical; quinone; toxicity;
D O I
10.1016/S1388-1981(02)00247-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
Catechol-containing antioxidants are able to protect against lipid peroxidation by nonenzymatic scavenging of free radicals with their catechol moiety. During their antioxidant activity, catechol oxidation products such as semiquinone radicals and quinones are formed. These oxidation products of 4-methylcatechol inactivate the GSH-dependent protection against lipid peroxidation and the calcium sequestration in liver microsomes. This effect is probably due to arylation by oxidation products of 4-methylcatechol of free thiol groups of the enzymes responsible for the GSH-dependent protection and calcium sequestration, i.e. the free radical reductase and calcium ATPase. It is concluded that a catechol-containing antioxidant might shift radical damage from lipid peroxidation to sulfhydryl arylation. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:279 / 284
页数:6
相关论文
共 26 条
[1]
Structure-activity study on the quinone/quinone methide chemistry of flavonoids [J].
Awad, HM ;
Boersma, MG ;
Boeren, S ;
van Bladeren, PJ ;
Vervoort, J ;
Rietjens, IMCM .
CHEMICAL RESEARCH IN TOXICOLOGY, 2001, 14 (04) :398-408
[2]
OXIDANTS AND ANTIOXIDANTS - STATE-OF-THE-ART [J].
BAST, A ;
HAENEN, GRMM ;
DOELMAN, CJA .
AMERICAN JOURNAL OF MEDICINE, 1991, 91 :S2-S13
[3]
BAST A, 2002, IN PRESS ENV TOXICOL
[4]
BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
[6]
Functional food science and defence against reactive oxidative species [J].
Diplock, AT ;
Charleux, JL ;
Crozier-Willi, G ;
Kok, FJ ;
Rice-Evans, C ;
Roberfroid, M ;
Stahl, W ;
Viña-Ribes, J .
BRITISH JOURNAL OF NUTRITION, 1998, 80 :S77-S112
[7]
DYBING E, 1976, MOL PHARMACOL, V12, P911
[8]
ACTIVATION OF THE MICROSOMAL GLUTATHIONE-S-TRANSFERASE BY METABOLITES OF ALPHA-METHYLDOPA [J].
HAENEN, GRMM ;
JANSEN, FP ;
VERMEULEN, NPE ;
BAST, A .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1991, 287 (01) :48-52
[9]
PROTECTION AGAINST LIPID-PEROXIDATION BY A MICROSOMAL GLUTATHIONE-DEPENDENT LABILE FACTOR [J].
HAENEN, GRMM ;
BAST, A .
FEBS LETTERS, 1983, 159 (1-2) :24-28
[10]
Flavonoids as peroxynitrite scavengers: the role of the hydroxyl groups [J].
Heijnen, CGM ;
Haenen, GRMM ;
van Acker, FAA ;
van der Vijgh, WJF ;
Bast, A .
TOXICOLOGY IN VITRO, 2001, 15 (01) :3-6