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Research ArticleArticle

In Vitro Biotransformation of Xanthohumol, a Flavonoid from Hops (Humulus lupulus), by Rat Liver Microsomes

Meltem Yilmazer, Jan F. Stevens, Max L. Deinzer and Donald R. Buhler
Drug Metabolism and Disposition March 2001, 29 (3) 223-231;
Meltem Yilmazer
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Jan F. Stevens
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Max L. Deinzer
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Donald R. Buhler
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Abstract

Xanthohumol (XN) is the major prenylated flavonoid of the female inflorescences (cones) of the hop plant (Humulus lupulus). It is also a constituent of beer, the major dietary source of prenylated flavonoids. Recent studies have suggested that XN may have potential cancer-chemopreventive activity, but little is known about its metabolism. We investigated the biotransformation of XN by rat liver microsomes. Three major polar metabolites were produced by liver microsomes from either untreated rats or phenobarbital-pretreated rats as detected by reverse-phase high-performance liquid chromatography analysis. Liver microsomes from isosafrole- and β-naphthoflavone-pretreated rats formed another major nonpolar metabolite in addition to the three polar metabolites. As determined by liquid chromatography/mass spectrometry and 1H NMR analyses, the three major polar microsomal metabolites of XN were tentatively identified as 1) 5′′-isopropyl-5′′-hydroxydihydrofurano[2′′,3′′:3′,4′]-2′,4-dihydroxy-6′-methoxychalcone; 2) 5′′-(2′′′-hydroxyisopropyl)-dihydrofurano[2′′,3′′:3′,4′]-2′,4-dihydroxy-6′-methoxychalcone; and 3) a derivative of XN with an additional hydroxyl function at the B ring. The nonpolar XN metabolite was identified as dehydrocycloxanthohumol.

Footnotes

  • Send reprint requests to: Dr. Donald R. Buhler, Dept. of Environmental and Molecular Toxicology, Oregon State University, ALS 1007 Corvallis, OR 97331. E-mail: Donald.Buhler{at}orst.edu

  • Supported by the Hop Research Council, National Institute of Environmental Health Sciences Grant ES00210, and the Turkish Council of Higher Education.

  • Abbreviations used are::
    CYP
    cytochrome P450
    XN
    xanthohumol
    DH
    dehydrocycloxanthohumol hydrate (xanthohumol B)
    DX
    dehydrocycloxanthohumol (xanthohumol C)
    HPLC
    high-performance liquid chromatography
    LC/MS
    liquid chromatography/mass spectrometry
    MS-MS
    tandem mass spectrometry
    metabolite 1 (M1)
    5′′-isopropyl-5′′-hydroxydihydrofurano[2′′,3′′:3′,4′]-2′,4-dihydroxy-6′-methoxychalcone
    metabolite 2 (M2)
    5′′-(2-hydroxyisopropyl)-dihydrofurano[2′′,3′′:3′,4′]-2′,4-dihydroxy-6′-methoxychalcone
    M3 and M4
    metabolites 3 and 4
    TAO
    troleandomycin
    PB
    phenobarbital
    ISF
    isosafrole
    BNF
    β-naphthoflavone
    ANF
    α-naphthoflavone
    SKF-525
    proadifen
    TCPO
    1,2-epoxy-3,3,3-trichloropropane
    RDA
    retro Diels-Alder
    APCI
    atmospheric pressure chemical ionization
    1H NMR
    proton nuclear magnetic resonance
    • Received August 14, 2000.
    • Accepted November 8, 2000.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 29 (3)
Drug Metabolism and Disposition
Vol. 29, Issue 3
1 Mar 2001
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Research ArticleArticle

In Vitro Biotransformation of Xanthohumol, a Flavonoid from Hops (Humulus lupulus), by Rat Liver Microsomes

Meltem Yilmazer, Jan F. Stevens, Max L. Deinzer and Donald R. Buhler
Drug Metabolism and Disposition March 1, 2001, 29 (3) 223-231;

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Research ArticleArticle

In Vitro Biotransformation of Xanthohumol, a Flavonoid from Hops (Humulus lupulus), by Rat Liver Microsomes

Meltem Yilmazer, Jan F. Stevens, Max L. Deinzer and Donald R. Buhler
Drug Metabolism and Disposition March 1, 2001, 29 (3) 223-231;
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