title: Metabolism of xanthohumol and isoxanthohumol, prenylated flavonoids from hops (Humulus lupulus L.), by human liver microsomes.
abstract: The female flowers of hops (Humulus lupulus L.) used to flavor beer contain the prenylated flavonoids xanthohumol (XN) and isoxanthohumol (IX). IX is moderately estrogenic in vitro and XN has pharmacological properties that might make it useful as a cancer chemopreventive agent. The metabolism of these dietary flavonoids was investigated in vitro using human liver microsomes. Hydroxylation of a prenyl methyl group was the primary route of oxidative metabolism forming either cis or trans hydroxylated metabolites of IX but only the trans isomer of XN. The double bond on the prenyl group of both compounds formed an epoxide which was opened by an intramolecular reaction with the neighboring hydroxyl group. The potent phytoestrogen 8-prenylnaringenin (8-PN) was detected as a demethylation product of IX. However, the analogous demethylation reaction was not observed for XN. Since XN can be converted to IX through acid-catalyzed cyclization in the stomach, XN might contribute to the in vivo levels of estrogenic 8-PN following consumption of hops extracts.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois 60612-7231, USA.
authors.forename: Dejan
authors.initials: D
authors.lastname: Nikolic
authors.forename: Yongmei
authors.initials: Y
authors.lastname: Li
authors.forename: Lucas R
authors.initials: LR
authors.lastname: Chadwick
authors.forename: Guido F
authors.initials: GF
authors.lastname: Pauli
authors.forename: Richard B
authors.initials: RB
authors.lastname: van Breemen
mesh_terms: D002853:Chromatography, Liquid; D003500:Cyclization; D005419:Flavonoids / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D027582:Humulus / Q000737:chemistry*; D013058:Mass Spectrometry; D008862:Microsomes, Liver / Q000378:metabolism*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000378:metabolism; D011427:Propiophenones / Q000737:chemistry / Q000378:metabolism*
chemical_list: D005419:Flavonoids; D010936:Plant Extracts; D011427:Propiophenones; C104536:xanthohumol