Identification of o-quinone/quinone methide metabolites of quercetin in a cellular in vitro system.
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.
Awad
Hanem M
HM
Laboratory of Biochemistry, Wageningen University, Dreijenlaan 3, 6703 HA Wageningen, The Netherlands.
Boersma
Marelle G
MG
Boeren
Sjef
S
van der Woude
Hester
H
van Zanden
Jelmer
J
van Bladeren
Peter J
PJ
Vervoort
Jacques
J
Rietjens
Ivonne M C M
IM
D000818:Animals; D016227:Benzoquinones / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D005978:Glutathione / Q000737:chemistry / Q000378:metabolism; D045563:Indolequinones; D007211:Indoles / Q000737:chemistry / Q000378:metabolism*; D013058:Mass Spectrometry / Q000379:methods; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000737:chemistry / Q000378:metabolism; D011794:Quercetin / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D011809:Quinones / Q000737:chemistry / Q000378:metabolism*; D014407:Tumor Cells, Cultured / Q000187:drug effects / Q000378:metabolism
D016227:Benzoquinones; D045563:Indolequinones; D007211:Indoles; D011809:Quinones; C068040:quinone methide; C004532:quinone; D011794:Quercetin; D014442:Monophenol Monooxygenase; D005978:Glutathione