Evaluation of the Total Peroxyl Radical-Scavenging Capacity of Flavonoids: Structure−Activity Relationships

Abstract

The antioxidant activity of a series of flavonoids against peroxyl radicals generated from thermal homolysis of 2,2‘-azobis-amidinopropane was determined by the Total Oxyradical Scavenging Capacity (TOSC) assay. Seven flavonoids with hydroxy and/or methoxy substitution were analyzed and compared to the water-soluble vitamin E analogue Trolox. The most active compound was the flavonol quercetin, followed by its 3-glycoside derivative rutin; these were 7 and 5 times, respectively, better scavengers of peroxyl radical than Trolox. Among the flavones with both hydroxy and methoxy substitution, the most active against peroxyl radicals was the 5,6,4‘-trihydroxy-7,8,3‘-trimethoxyflavone (thymonin), with a TOSC value 1.5 times greater than that of Trolox. The activity of the remaining flavones was in the following relative order: 5,4‘-dihydroxy-6,7,8,3‘-tetramethoxyflavone > 5-hydroxy-3,6,7,3‘,4‘-pentamethoxyflavone (artemetin) > 5,4‘-dihydroxy-3,6,7-trimethoxyflavone > 5,6,7,8,2‘,3‘,4‘,5‘-octamethoxyflavone (agehoustin A). The data suggest a potential role for dietary intake of flavonoid-containing foods in lowering the risk of certain pathophysiologies that have been associated with free-radical-mediated events.