Identification of o-quinone/quinone methide metabolites of quercetin in a cellular in vitro system

• Published in: FEBS letters Vol. 520; no. 1; pp. 30 - 34
• Main Authors: Awad, Hanem M., Boersma, Marelle G., Boeren, Sjef, van der Woude, Hester, van Zanden, Jelmer, van Bladeren, Peter J., Vervoort, Jacques, Rietjens, Ivonne M.C.M.
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 05.06.2002
• Subjects: Animals; Benzoquinones - chemistry; Benzoquinones - metabolism; Chromatography, High Pressure Liquid; Glutathione - chemistry; Glutathione - metabolism; Glutathionyl adduct; Indolequinones; Indoles - chemistry; Indoles - metabolism; Mass Spectrometry - methods; Melanoma cells; Molecular Structure; Monophenol Monooxygenase - chemistry; Monophenol Monooxygenase - metabolism; Pro-oxidant; Quercetin; Quercetin - chemistry; Quercetin - metabolism; Quercetin - pharmacology; Quinone/quinone methide; Quinones - chemistry; Quinones - metabolism; Tumor Cells, Cultured - drug effects; Tumor Cells, Cultured - metabolism; Quinone/quinone methide; Glutathionyl adduct; Melanoma cells; Pro-oxidant; Quercetin
• ISSN: 0014-5793; 1873-3468
• DOI: 10.1016/S0014-5793(02)02754-0

Formation of quercetin quinone/quinone methide metabolites, reflected by formation of the glutathionyl quercetin adducts as authentic metabolites, was investigated in an in vitro cell model (B16F-10 melanoma cells). Results of the present study clearly indicate the formation of glutathionyl quercetin adducts in a tyrosinase-containing melanoma cell line, expected to be representative also for peroxidase-containing mammalian cells and tissues. The data obtained also support that the adducts are formed intracellular and subsequently excreted into the incubation medium and reveal for the first time evidence for the pro-oxidative metabolism of quercetin in a cellular in vitro model.