FEBS Letters
Volume 491, Issue 3 , Pages 252-256, 2 March 2001

In vitro glucuronidation of xanthohumol, a flavonoid in hop and beer, by rat and human liver microsomes

Edited by Pierre Jolles

  • M. Yilmazer

      Affiliations

    • Department of Environmental and Molecular Toxicology, ALS Building 1007, Oregon State University, Corvallis, OR 97331, USA
    • ,
  • J.F. Stevens

      Affiliations

    • Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA
    • Present address: Department of Bioorganic Chemistry, FEW/OAC, Free University, De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands.
    • ,
  • D.R. Buhler

      Affiliations

    • Department of Environmental and Molecular Toxicology, ALS Building 1007, Oregon State University, Corvallis, OR 97331, USA
    • Corresponding Author InformationCorresponding author. Fax: (1)-541-737 0497

Received 8 January 2001; received in revised form 5 February 2001; accepted 6 February 2001.

Abstract 

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 β-glucuronidase followed by liquid chromatography/mass spectrometry and nuclear magnetic resonance analysis revealed that these were C-4′ and C-4 monoglucuronides of XN.

Keywords:  Xanthohumol, Flavonoid, Hop, Glucuronidation, Rat, Human

Abbreviations:  XN, xanthohumol, IX, isoxanthohumol, PB, phenobarbital, ISF, isosafrole, BNF, β-naphthoflavone, G1, glucuronide 1, G2, glucuronide 2, G3, glucuronide 3, G4, glucuronide 4, HPLC, high-performance liquid chromatography, LC/MS, liquid chromatography/mass spectrometry, 1H-NMR, proton nuclear magnetic resonance, UDPGA, uridine 5′-diphosphoglucuronic acid

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PII: S0014-5793(01)02210-4

FEBS Letters
Volume 491, Issue 3 , Pages 252-256, 2 March 2001

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