Reactions of peroxynitrite with cocoa procyanidin oligomers.
Peroxynitrite is a mediator molecule in inflammation, and its biological properties are being studied extensively. Flavonoids, which are natural plant constituents, protect against peroxynitrite and thereby could play an anti-inflammatory role. Procyanidin oligomers of different sizes (monomer through nonamer), isolated from the seeds of Theobroma cacao, were recently examined for their ability to protect against peroxynitrite-dependent oxidation of dihydrorhodamine 123 and nitration of tyrosine and were found to be effective in attenuating these reactions. The tetramer was particularly efficient at protecting against oxidation and nitration reactions. Epicatechin oligomers found in cocoa powder and chocolate may be a potent dietary source for defense against peroxynitrite.
Arteel
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Institut für Physiologische Chemie I, Heinrich-Heine-Universität Düsseldorf, D-40001 Düsseldorf, Germany.
Schroeder
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Sies
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D044946:Biflavonoids; D002099:Cacao; D002392:Catechin / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D004347:Drug Interactions; D009566:Nitrates / Q000037:antagonists & inhibitors*; D016877:Oxidants / Q000037:antagonists & inhibitors*; D010084:Oxidation-Reduction / Q000187:drug effects; D044945:Proanthocyanidins; D012235:Rhodamines / Q000737:chemistry; D013329:Structure-Activity Relationship; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry
D044946:Biflavonoids; D009566:Nitrates; D016877:Oxidants; D044945:Proanthocyanidins; D012235:Rhodamines; C058319:dihydrorhodamine 123; C039642:peroxynitric acid; C002744:3-nitrotyrosine; D014443:Tyrosine; C017674:procyanidin; D002392:Catechin