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The reaction of flavonoid metabolites with peroxynitrite

Pollard, S.E., Kuhnle, G.G.C., Vauzour, D., Vafeiadou, K., Tzounis, X., Whiteman, M., Rice-Evans, C. and Spencer, J.P.E. (2006) The reaction of flavonoid metabolites with peroxynitrite. Biochemical and Biophysical Research Communications, 350 (4). pp. 960-968. ISSN 0006-291X

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To link to this article DOI: 10.1016/j.bbrc.2006.09.131

Abstract/Summary

There is much interest in the bioactivity of in vivo flavonoid metabolites. We report for the first time the hierarchy of reactivity of flavonoid metabolites with peroxynitrite and characterise novel reaction products. O-Methylation of the B-ring catechol containing flavonoids epicatechin and quercetin, and O-glucuronidation of all flavonoids reduced their reactivity with peroxynitrite. The reaction of the flavanones hesperetin and naringenin and their glucuronides resulted in the formation of multiple mono-nitrated and nitrosated products. In contrast, the catechol-containing flavonoids epicatechin and quercetin yielded oxidation products which when trapped with glutathione led to the production of glutathionyl-conjugates. However, the O-methylated metabolites of epicatechin yielded both mono-and di-nitrated products and nitrosated metabolites. The 3'-O-methyl metabolite of quercetin also yielded a nitrosated species, although its counterpart 4'-O-methyl quercetin yielded only oxidation products. Such products may represent novel metabolic products in vivo and may also express cellular activity. (c) 2006 Elsevier Inc. All rights reserved.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Food and Nutritional Sciences
Interdisciplinary centres and themes > Institute for Cardiovascular and Metabolic Research (ICMR)
ID Code:13071
Uncontrolled Keywords:flavonoid, peroxynitrite, metabolite, glucuronide, O-methylated, 3-nitrotyrosine, NEURONAL SIGNAL-TRANSDUCTION, IN-VIVO METABOLITES, INDUCED CELL-DEATH, SMALL-INTESTINE, HUMAN PLASMA, RED WINE, ANTIOXIDANT ACTIVITY, BEHAVIORAL DEFICITS, TYROSINE NITRATION, OXIDATIVE-STRESS

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