In vitro glucuronidation of xanthohumol, a flavonoid in hop and beer, by rat and human liver microsomes.
Xanthohumol (XN) is the major prenylated flavonoid of hop plants and has been detected in beer. Previous studies suggest a variety of potential cancer chemopreventive effects for XN, but there is no information on its metabolism. The aim of this study was to investigate in vitro glucuronidation of XN by rat and human liver microsomes. Using high-performance liquid chromatography, two major glucuronides of XN were found with either rat or human liver microsomes. Release of the aglycone by enzymatic hydrolysis with beta-glucuronidase followed by liquid chromatography/mass spectrometry and nuclear magnetic resonance analysis revealed that these were C-4' and C-4 monoglucuronides of XN.
Yilmazer
M
M
Department of Environmental and Molecular Toxicology, Oregon State University, Corvallis 97331, USA.
Stevens
J F
JF
Buhler
D R
DR
D000818:Animals; D001515:Beer; D002851:Chromatography, High Pressure Liquid; D005419:Flavonoids / Q000378:metabolism*; D020723:Glucuronic Acid / Q000378:metabolism*; D005966:Glucuronidase / Q000378:metabolism; D020719:Glucuronides / Q000032:analysis* / Q000096:biosynthesis; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D008862:Microsomes, Liver / Q000737:chemistry / Q000378:metabolism*; D011427:Propiophenones / Q000378:metabolism*; D051381:Rats; D017207:Rats, Sprague-Dawley
D005419:Flavonoids; D020719:Glucuronides; D011427:Propiophenones; D020723:Glucuronic Acid; D005966:Glucuronidase; C104536:xanthohumol