Iron and copper chelation by flavonoids:: an electrospray mass spectrometry study

被引:278
作者
Fernandez, MT
Mira, ML
Florêncio, MH
Jennings, KR
机构
[1] Univ Lisbon, Fac Ciencias, Dept Quim & Bioquim, P-1749016 Lisbon, Portugal
[2] Fac Med Lisbon, Ctr Metab & Endocrinol, Genet Lab, P-1600 Lisbon, Portugal
[3] Univ Warwick, Dept Biol Sci, Coventry CV4 7AL, W Midlands, England
关键词
flavonoids; metal chelation; electrospray mass spectrometry; antioxidants;
D O I
10.1016/S0162-0134(02)00511-1
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
Flavonoids are well known as effective free radical scavengers exhibiting therefore an antioxidant behaviour. Another antioxidant mechanism however may result from the ability they have to chelate metal ions, rendering them inactive to participate in free radical generating reactions. Electrospray. Mass spectrometry has been used to study metal ion interactions with a set of flavonoids from different classes. Complexes with a range of stoichiometries, of metal: flavonoid, 1:1, 1:2 -2:2, 2:3 have been observed. The stoichfometry 1:2 is in general the preferred one. It is established for flavones and for the flavanone naringenin that the binding metal sites Are preferentially at the 5-hydroxyl and 4-oxo, groups. Redox reactions are also observed through the change of the oxidation state of the metal, jointly with the oxidation of the flavonoid by loss of hydrogen. Structures of the oxidized species of some flavonoids are proposed. (C) 2002 Elsevier Science Inc. All rights reserved.
引用
收藏
页码:105 / 111
页数:7
相关论文
共 33 条
[1]   CHELATING AND FREE-RADICAL SCAVENGING MECHANISMS OF INHIBITORY-ACTION OF RUTIN AND QUERCETIN IN LIPID-PEROXIDATION [J].
AFANASEV, IB ;
DOROZHKO, AI ;
BRODSKII, AV ;
KOSTYUK, VA ;
POTAPOVITCH, AI .
BIOCHEMICAL PHARMACOLOGY, 1989, 38 (11) :1763-1769
[2]   Characterization of drugs as antioxidant prophylactics [J].
Aruoma, OI .
FREE RADICAL BIOLOGY AND MEDICINE, 1996, 20 (05) :675-705
[3]   Free radicals, oxidative stress, and antioxidants in human health and disease [J].
Aruoma, OI .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1998, 75 (02) :199-212
[4]   Phagocytes and oxidative stress [J].
Babior, BM .
AMERICAN JOURNAL OF MEDICINE, 2000, 109 (01) :33-44
[5]   THE EFFECT OF PH ON YIELDS OF HYDROXYL RADICALS PRODUCED FROM SUPEROXIDE BY POTENTIAL BIOLOGICAL IRON CHELATORS [J].
BAKER, MS ;
GEBICKI, JM .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1986, 246 (02) :581-588
[6]   The free radical theory of aging matures [J].
Beckman, KB ;
Ames, BN .
PHYSIOLOGICAL REVIEWS, 1998, 78 (02) :547-581
[7]  
Bors W, 1987, Free Radic Res Commun, V2, P289, DOI 10.3109/10715768709065294
[8]  
Brown JE, 1998, BIOCHEM J, V330, P1173
[9]   The lag phase [J].
Cadenas, E ;
Sies, H .
FREE RADICAL RESEARCH, 1998, 28 (06) :601-609
[10]   Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships [J].
Cao, GH ;
Sofic, E ;
Prior, RL .
FREE RADICAL BIOLOGY AND MEDICINE, 1997, 22 (05) :749-760