Flavonoids quercetin, myricetin, kaemferol and (+)-catechin as antioxidants in methyl linoleate

Abstract

The antioxidant effect of the flavonoids quercetin, myricetin, kaemferol, (+)-catechin and rutin on methyl linoleate oxidation was investigated. In addition, the synergistic effects of flavonoids and α-tocopherol were studied. Oxidation was monitored by conjugated diene measurement and by determining the formation of hydroperoxide isomers by HPLC. The antioxidant activity of flavonoids in non-polar methyl linoleate differ from that previously reported in water-containing systems, such as LDL and liposome systems. The activity of antioxidants (10–1000 μM) measured by hydroperoxide formation decreased in the order: myricetin>quercetin>α-tocopherol>(+)-catechin >kaemferol=rutin. The antioxidant activity of flavonoids increased as the number of phenolic hydroxyl groups increased. In addition to the number of hydroxyl groups, other structural features such as the 2,3 double bond in the C-ring and a glycoside moiety in the molecule had an effect on the antioxidant activity. Myricetin and rutin, especially had a synergistic effect with α-tocopherol. Myricetin, quercetin and rutin protected α-tocopherol from decomposition, myricetin being the most protective. The relative hydrogen-donating activity measured by the ratio of cis,trans- to trans,transhydroperoxide isomers formed during oxidation decreased in the order: α-tocopherol >myricetin>quercetin. Hydroperoxide isomeric distribution of the samples containing kaemferol or rutin did not differ from the control. Thus, although α-tocopherol was the most effective hydrogendonor, myricetin and quercetin were more effective antioxidants in inhibiting the hydroperoxide formation in methyl linoleate. © 1999 Society of Chemical Industry