Identification of Glutathione-Related Quercetin Metabolites in Humans

The glutathionylation of quercetin was investigated in murine hepatic suspensions, in the absence of chemically or enzymatically induced oxidative stress, and in human urine after the consumption of 200 g of cooked onions (∼74 mg of quercetin). In murine hepatic suspensions, 22 metabolites, includin...

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Bibliographic Details
Published in:Chemical research in toxicology 2006-11, Vol.19 (11), p.1525-1532
Main Authors: Hong, Yun-Jeong, Mitchell, Alyson E
Format: Article
Language:English
Subjects:
Acetylcysteine - urine
Adult
Allium cepa
Animals
Cells, Cultured
Female
Gas Chromatography-Mass Spectrometry
Glutathione - metabolism
Humans
Liver - cytology
Liver - metabolism
Male
Mice
Molecular Structure
Quercetin - analogs & derivatives
Quercetin - metabolism
Quercetin - urine
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Summary:The glutathionylation of quercetin was investigated in murine hepatic suspensions, in the absence of chemically or enzymatically induced oxidative stress, and in human urine after the consumption of 200 g of cooked onions (∼74 mg of quercetin). In murine hepatic suspensions, 22 metabolites, including glucuronide, sulfate, and glutathione conjugates of quercetin, were identified by LC/ESI-MS/MS. In total, eight glutathione conjugates were identified in these suspension, including three isomeric forms of monoglutathionyl quercetin, two isomers of monoglutathionyl quercetin glucuronide, and three isomers of glutathionyl methyl quercetin. Quinone forms of glutathionyl quercetin and glutathionyl methyl quercetin were also apparent in mass spectra. In humans, several glutathione-related metabolites of quercetin were identified in urine as mercapturic acids of common hydroxyphenylacetic acids generated by the microbial degredation of quercetin in the gut. These include mercaptic acids of dihydroxytoluene, dihydroxybenzaldehyde, dihydroxyphenylacetic acid, dihydroxycinnamic acid, and dihydroxyphenylpropionic acid. Our results suggest that glutathionylation of quercetin occurs in both murine hepatic suspensions and humans and indicate that under certain conditions, quercetin intermediates require inactivation through conjugation with glutathione.
ISSN:0893-228X
1520-5010
DOI:10.1021/tx0601758