Flavonoid oxidation by the radical generator AIBN: A unified mechanism for quercetin radical scavenging

Venkat Krishnamachari, Lanfang H. Levine, Paul W. Paré

Research output: Contribution to journalArticle

118 Scopus citations

Abstract

Four oxidized flavonoid derivatives generated from reacting quercetin (a pentahydroxylated flavone) with the peroxyl radical generator 2,2′-azobis-isobutyronitrile (AIBN) were isolated by chromatographic methods and identified by NMR and MS analyses. Compounds included 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (2); 1,3,11a-trihydroxy-9-(3,5,7-trihydroxy-4H-1-benzopyran-4-on-2-yl)-5a-(3, 4-dihydroxyphenyl)-5,6,11-hexahydro-5,6,11-trioxanaphthacene-12-one (3); 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid (4); and methyl 3,4-dihydroxyphenylglyoxylate (5). Product ratios under different hydrogen ion concentrations and external nucleophiles revealed that two of the products, namely the substituted benzofuranone (2) and the depside (4), are generated from a common carbocation intermediate. Indirect evidence for the operation of a cyclic concerted mechanism in the formation of the dimeric product (3) is provided. The identification of these products supports the model that the principal site of scavenging reactive oxygen species (ROS) in quercetin is the ̂-dihydroxyl substituent in the B-ring, as well as the C-ring olefinic linkage.

Original languageEnglish
Pages (from-to)4357-4363
Number of pages7
JournalJournal of Agricultural and Food Chemistry
Volume50
Issue number15
DOIs
StatePublished - Jul 17 2002

Keywords

  • AIBN
  • Antioxidant
  • Flavonols
  • Oxidizing agents
  • Peroxyl radicals
  • Quercetin

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