Redox properties of individual quercetin moieties

Free Radical Biology & Medicine
Eva HeřmánkováJan Vacek

Abstract

Quercetin is one of the most prominent and widely studied flavonoids. Its oxidation has been previously investigated only indirectly by comparative analyses of structurally analogous compounds, e.g. dihydroquercetin (taxifolin). To provide direct evidence about the mechanism of quercetin oxidation, we employed selective alkylation procedures for the step-by-step blocking of individual redox active sites, i.e. the catechol, resorcinol and enol C-3 hydroxyls, as represented by newly prepared quercetin derivatives 1-3. Based on the structure-activity relationship (SAR), electrochemical, and computational (density functional theory) studies, we can clearly confirm that quercetin is oxidized in the following steps: the catechol moiety is oxidized first, forming the benzofuranone derivative via intramolecular rearrangement mechanism; therefore the quercetin C-3 hydroxy group cannot be involved in further oxidation reactions or other biochemical processes. The benzofuranone is oxidized subsequently, followed by oxidation of the resorcinol motif to complete the electrochemical cascade of reactions. Derivatization of individual quercetin hydroxyls has a significant effect on its redox behavior, and, importantly, on its antiradical and s...Continue Reading

Citations

Feb 28, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Cristina ZaragozáMelchor Álvarez-Mon
Mar 20, 2020·International Journal of Molecular Sciences·Zhengwen LiGuido R M M Haenen
Oct 6, 2020·Frontiers in Cell and Developmental Biology·Huanhuan XuJun Sheng
Aug 22, 2020·Free Radical Biology & Medicine·Antonis D TsiailanisAndreas G Tzakos

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