Inhibition of human cytochrome P450 enzymes by hops (Humulus lupulus) and hop prenylphenols

European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences
Yang YuanRichard B van Breemen

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
May 1, 1996·Fundamental and Applied Toxicology : Official Journal of the Society of Toxicology·Z JayyosiM Kelley
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
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
Oct 15, 2005·Nature Reviews. Drug Discovery·Larry C Wienkers, Timothy G Heath
Apr 14, 2006·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Jian GuoRichard B van Breemen
Mar 1, 2008·Journal of Ethnopharmacology·Paola Zanoli, Manuela Zavatti
May 21, 2010·Molecular Nutrition & Food Research·Selin BolcaHerman Depypere
Apr 12, 2011·Journal of Agricultural and Food Chemistry·Brian C FosterSuzanne Desjardins
Sep 17, 2013·Molecular Nutrition & Food Research·LeeCole LegetteJan F Stevens

❮ Previous
Next ❯

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
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
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
Apr 15, 2020·Journal of Agricultural and Food Chemistry·Richard B van BreemenJudy L Bolton
Jan 5, 2019·Chemical Research in Toxicology·Judy L BoltonBirgit M Dietz

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.