Antioxidant evaluation of O-methylated metabolites of catechin, epicatechin and quercetin

Catechins and quercetin are major polyphenols in many plant foods that have been related to health promotion. In the human organism they are largely metabolized to different metabolites, which are further found in plasma and should contribute to the biological effects associated to the intake of the parent compounds. An important step in quercetin and catechins metabolism is the O-methylation of the catechol group, which can be expected to have an effect on their antioxidant and scavenging properties. In the present work, the 3'- and 4'-methylethers of catechin and epicatechin have been prepared and characterised and their antioxidant activity evaluated and compared to that of the corresponding quercetin derivatives. The antioxidant activity was assessed using the ferric reducing power (FRAP) assay and two methods based on the ability to scavenge the ABTS(center dot+) radical cation at different pH values. In these assays the three flavonoids behave as better radical scavengers and reducing compounds than usually recognised antioxidants like alpha-tocopherol. The O-methylation of the hydroxyls of the catechol B-ring resulted in a decrease of the antioxidant activity with regard to the parent compounds. However, the methylated metabolites still retain significant radical scavenging activity at pH 7.4, suggesting that they could act as potential antioxidants ill physiological conditions. Quercetin and its methylated metabolites showed, in general, greater activity than (epi)catechin and their O-methyl derivatives, although a relatively high antioxidant activity was found in the case of 3'-O-methyl catechin at pH 7.4, comparable to those of its parent compound and the quercetin metabolites. It was confirmed that the antioxidant activity of the flavonoids assayed was strongly dependent on the pH of the medium, showing higher activity at greater pH values. The results obtained are expected to contribute to the understanding of the mechanisms involved in the biological effects attributed to the intake of flavonoid-rich diets. (C) 2009 Elsevier B.V. All rights reserved.