Consequences of quercetin methylation for its covalent glutathione and DNA adduct formation

Chemico-biological Interactions
Hester van der WoudeIvonne M C M Rietjens

Abstract

This study investigates the pro-oxidant activity of 3'- and 4'-O-methylquercetin, two relevant phase II metabolites of quercetin without a functional catechol moiety, which is generally thought to be important for the pro-oxidant activity of quercetin. Oxidation of 3'- and 4'-O-methylquercetin with horseradish peroxidase in the presence of glutathione yielded two major metabolites for each compound, identified as the 6- and 8-glutathionyl conjugates of 3'- and 4'-O-methylquercetin. Thus, catechol-O-methylation of quercetin does not eliminate its pro-oxidant chemistry. Furthermore, the formation of these A-ring glutathione conjugates of 3'- and 4'-O-methylquercetin indicates that quercetin o-quinone may not be an intermediate in the formation of covalent quercetin adducts with glutathione, protein and/or DNA. In additional studies, it was demonstrated that covalent DNA adduct formation by a mixture of [4-(14)C]-3'- and 4'-O-methylquercetin in HepG2 cells amounted to only 42% of the level of covalent adducts formed by a similar amount of [4-(14)C]-quercetin. Altogether, these results reveal the effect of methylation of the catechol moiety of quercetin on its pro-oxidant behavior. Methylation of quercetin does not eliminate but co...Continue Reading

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Dec 20, 2005·Chemical Research in Toxicology·Hester van der WoudeIvonne M C M Rietjens

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Citations

Jul 31, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Renato B PereiraPatrícia Valentão
Jan 19, 2010·Phytochemistry·David P DixonRobert Edwards
Aug 19, 2007·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·M HarwoodT C Lines
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Aug 7, 2020·Antioxidants·Igor IlyasovIrina Selivanova
Dec 31, 2008·Journal of Agricultural and Food Chemistry·Iva FernandesNuno Mateus
Jul 1, 2020·Biomedicine & Pharmacotherapy = Biomédecine & Pharmacothérapie·Veerta SharmaThakur Gurjeet Singh
Nov 6, 2007·Molecular Pharmaceutics·Li ZhangGe Lin
Nov 23, 2006·Chemical Research in Toxicology·Yee Y Lee-HilzIvonne M C M Rietjens

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