Peroxynitrite scavenging of flavonoids: structure activity relationship

被引:153
作者
Heijnen, CGM
Haenen, GRMM
Vekemans, JAJM
Bast, A
机构
[1] Univ Maastricht, Fac Med, Dept Pharmacol & Toxicol, NL-6200 MD Maastricht, Netherlands
[2] Eindhoven Univ Technol, Lab Macromol & Organ Chem, NL-5600 MB Eindhoven, Netherlands
关键词
flavonoid; phenolic compounds; structure activity relationships; peroxynitrite scavenging; antioxidant; Hammett sigma;
D O I
10.1016/S1382-6689(01)00083-7
中图分类号
X [环境科学、安全科学];
学科分类号
08 ; 0830 ;
摘要
Peroxynitrite can oxidise and nitrosylate biomolecules and is associated with several diseases. The peroxynitrite scavenging of substituted phenols and several flavonoids was studied. The activity of phenol (poor scavenger) is positively influenced by electron donating substituents. A good correlation was found between the peroxynitrite scavenging activity of the substituted phenols and the Hammett sigma or the E-HOMO. Flavonols containing a catechol group (3'- and 4'-OH) in ring B (rutin and monohydroxyethyl rutoside) or an AC-ring with three OH groups (3-, 5- and 7-OH) were potent scavengers. Evidence has been produced that in the AC-ring the 3-OH group was the reactive centre and that the reactivity of this group was positively influenced by electron donating groups at the 5 and/or 7 position (galangin, kaempferol, trihydroxyethyl quercetin). (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:199 / 206
页数:8
相关论文
共 26 条
[21]   Nitric oxide regulation of tissue free radical injury [J].
Rubbo, H ;
DarleyUsmar, V ;
Freeman, BA .
CHEMICAL RESEARCH IN TOXICOLOGY, 1996, 9 (05) :809-820
[22]  
Sadeghi-Hashjin G, 1998, CLIN EXP ALLERGY, V28, P1464
[23]   Influence of iron chelation on the antioxidant activity of flavonoids [J].
van Acker, SABE ;
van Balen, GP ;
van den Berg, DJ ;
Bast, A ;
van der Vijgh, WJF .
BIOCHEMICAL PHARMACOLOGY, 1998, 56 (08) :935-943
[24]   A quantum chemical explanation of the antioxidant activity of flavonoids [J].
vanAcker, SABE ;
deGroot, MJ ;
vandenBerg, DJ ;
Tromp, MNJL ;
DonneOpdenKelder, G ;
vanderVijgh, WJF ;
Bast, A .
CHEMICAL RESEARCH IN TOXICOLOGY, 1996, 9 (08) :1305-1312
[25]   Structural aspects of antioxidant activity of flavonoids [J].
vanAcker, SABE ;
vandenBerg, DJ ;
Tromp, MNJL ;
Griffioen, DH ;
VanBennekom, WP ;
VanderVijgh, WJF ;
Bast, A .
FREE RADICAL BIOLOGY AND MEDICINE, 1996, 20 (03) :331-342
[26]   Endothelial dysfunction and peroxynitrite formation are early events in angiotensin-induced cardiovascular disorders [J].
Wattanapitayakul, SK ;
Weinstein, DM ;
Holycross, BJ ;
Bauer, JA .
FASEB JOURNAL, 2000, 14 (02) :271-278