Abstract
As hops (Humulus lupulus L.) are used in the brewing of beer and by menopausal women as estrogenic dietary supplements, the potential for hop extracts and hop constituents to cause drug-botanical interactions by inhibiting human cytochrome P450 enzymes was investigated. Inhibition of major human cytochrome P450 enzymes by a standardized hop extract and isolated hop prenylated phenols was evaluated using a fast and efficient assay based on ultrahigh pressure liquid chromatography-tandem mass spectrometry. The hop extract at 5 μg/mL inhibited CYP2C8 (93%), CYP2C9 (88%), CYP2C19 (70%), and CYP1A2 (27%) with IC50 values of 0.8, 0.9, 3.3, and 9.4 μg/mL, respectively, but time-dependent inactivation was observed only for CYP1A2. Isoxanthohumol from hops was the most potent inhibitor of CYP2C8 with an IC50 of 0.2 μM, whereas 8-prenylnaringenin was the most potent inhibitor of CYP1A2, CYP2C9 and CYP2C19 with IC50 values of 1.1 μM, 1.1 μM and 0.4 μM, respectively. Extracts of hops contain prenylated compounds such as the flavanones isoxanthohumol and 8-prenylnaringenin and the chalcone xanthohumol that can inhibit CYP450s, especially the CYP2C family, which may affect the efficacy and safety of some CYP2C substrate drugs when co-adminis...Continue Reading
References
Dec 1, 1994·Pharmacogenetics·J A Goldstein, S M de Morais
Nov 1, 1996·The Journal of Biological Chemistry·H YamazakiF P Guengerich
May 1, 1996·Fundamental and Applied Toxicology : Official Journal of the Society of Toxicology·Z JayyosiM Kelley
Mar 1, 1997·Critical Reviews in Toxicology·A PugaA G Menon
Mar 10, 1999·Journal of Chromatography. a·J F StevensM L Deinzer
Jul 27, 1999·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·C L MirandaD R Buhler
Apr 7, 2000·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·M C HendersonD R Buhler
Jul 17, 2001·British Journal of Clinical Pharmacology·G T TuckerS M Huang
Apr 25, 2003·The Journal of Steroid Biochemistry and Molecular Biology·Olaf SchaeferWolf-Dieter Schleuning
Jul 3, 2004·Phytochemistry·Jan F Stevens, Jonathan E Page
Dec 29, 2004·Journal of Natural Products·Lucas R ChadwickGuido F Pauli
Feb 16, 2005·Journal of Mass Spectrometry : JMS·Dejan NikolicRichard B van Breemen
Aug 4, 2005·Journal of Agricultural and Food Chemistry·Cassia R OverkJudy L Bolton
Aug 4, 2005·Journal of Agricultural and Food Chemistry·Sam PossemiersWilly Verstraete
Aug 16, 2005·Chemical Research in Toxicology·Birgit M DietzJudy L Bolton
Oct 15, 2005·Nature Reviews. Drug Discovery·Larry C Wienkers, Timothy G Heath
Mar 28, 2006·Cancer Letters·Emily C ColgateEmily Ho
Apr 14, 2006·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Jian GuoRichard B van Breemen
May 23, 2006·Pharmaceutical Research·Dejan NikolicRichard B van Breemen
Jun 15, 2007·Journal of Mass Spectrometry : JMS·Ari TolonenOlavi Pelkonen
Mar 1, 2008·Journal of Ethnopharmacology·Paola Zanoli, Manuela Zavatti
Jul 16, 2008·Chemico-biological Interactions·Cassia R OverkJudy L Bolton
Apr 11, 2009·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Scott W GrimmR Scott Obach
Apr 3, 2010·Current Drug Metabolism·D Rokitta, U Fuhr
May 21, 2010·Molecular Nutrition & Food Research·Selin BolcaHerman Depypere
Nov 9, 2010·Journal of Biopharmaceutical Statistics·Werner BrannathGernot Wassmer
Apr 12, 2011·Journal of Agricultural and Food Chemistry·Brian C FosterSuzanne Desjardins
Sep 17, 2013·Molecular Nutrition & Food Research·LeeCole LegetteJan F Stevens
Citations
Jan 20, 2016·Pharmacological Research : the Official Journal of the Italian Pharmacological Society·Tamara KrajnovićDanijela Maksimović-Ivanić
Oct 7, 2015·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Alyssa A Sprouse, Richard B van Breemen
Jan 2, 2016·Pharmacological Reviews·Janne T BackmanPertti J Neuvonen
Jul 1, 2015·Journal of Medicinal Chemistry·Richard B van Breemen
Jun 24, 2015·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Wei HeWei Xu
Jul 16, 2015·Journal of Agricultural and Food Chemistry·Monika StomporMirosław Anioł
Jun 5, 2015·Chemical Research in Toxicology·Ekaterina A Korobkova
Mar 17, 2015·Fitoterapia·Anna Katarzyna ŻołnierczykMirosław Anioł
Jun 9, 2016·Chemical Research in Toxicology·Shuai WangJudy L Bolton
Jul 1, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Monika StomporRafał Podgórski
Mar 16, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kateřina ŠtulíkováPavel Dostálek
Nov 7, 2016·The Journal of Pharmacology and Experimental Therapeutics·Juan Jose Arnaiz-CotMartin Morad
May 15, 2020·Drug Metabolism Reviews·Kai WangFeng Qiu
Jun 1, 2015·Molecular Informatics·Teresa KasererDaniela Schuster
Oct 12, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Darija Šarić MustapićMirza Bojić
Apr 20, 2019·Evidence-based Complementary and Alternative Medicine : ECAM·Daeun YimDong Hyun Kim
Nov 30, 2019·Critical Reviews in Food Science and Nutrition·Ixchel Osorio-PazSilvestre Alavez
Sep 22, 2019·Nutrients·Natalia Soldevila-DomenechRafael de la Torre
Jul 28, 2020·Nutrients·Kateřina LněničkováIva Boušová
Apr 15, 2020·Journal of Agricultural and Food Chemistry·Richard B van BreemenJudy L Bolton
Dec 2, 2014·Journal of Natural Products·René F Ramos AlvarengaShao-Nong Chen
Jan 5, 2019·Chemical Research in Toxicology·Judy L BoltonBirgit M Dietz