Humulus lupulus (Hops) | Botanical Profile

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Review & More General Articles on Humulus lupulus (Hops) by the UIC Botanical Center

With direct DOI links to the original articles.

Chadwick, L.; Pauli, G. F.; Farnsworth, N. R. The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on their estrogenic properties. Phytomedicine 2006, 13, 119-131.

Krause, E.; Yuan, Y.; Hajirahimkhan, A.; Dong, H.; Dietz, B. M.; Nikolic, D.; Pauli, G. F.; Bolton, J. L.; van Breemen, R. B. Biological and chemical standardization of a hop (Humulus lupulus) botanical dietary supplement. Biomed. Chromatogr. 2014, 28, 729-734.

Dietz, B. M.; Hajirahimkhan, A.; Dunlap, T. L.; Bolton, J. L. Botanicals and Their Bioactive Phytochemicals for Women’s Health. Pharmacological Reviews 2016, 68, 1026-1073.

Bolton, J. L.; Dunlap, T. L.; Hajirahimkhan, A.; Mbachu, O.; Chen, S.-N.; Chadwick, L.; Nikolic, D.; van Breemen, R. B.; Pauli, G. F.; Dietz, B. M. The Multiple Biological Targets of Hops and Bioactive Compounds. Chem. Res. Toxicol. 2019, 32, 222-233.

Peer-reviewed Publications on Humulus lupulus (Hops) by the UIC Botanical Center

Total number of publications on this botanical: 49

With direct DOI links to the original articles.

Liu, J.; Burdette, J. E.; Xu, H.; Gu, C.; van Breemen, R. B.; Bhat, K. P.; Booth, N.; Constantinou, A. I.; Pezzuto, J. M.; Fong, H. H.; Farnsworth, N. R.; Bolton, J. L. Evaluation of estrogenic activity of plant extracts for the potential treatment of menopausal symptoms. J. Agric. Food Chem. 2001, 49, 2472-2479.

Piersen, C. E. Phytoestrogens in botanical dietary supplements: implications for cancer. Integr. Cancer Ther. 2003, 2, 120-138.

Chadwick, L.; Fröhlich, R.; Bolton, J.; van Breemen, R.; Overk, C.; Burdette, J.; Nikolic, D.; Fong, H. H. S.; Farnsworth, N.; Pauli, G. F. Estrogens and congeners from spent hops (Humulus lupulus L.). J. Nat. Prod. 2004, 67, 2024-2032.

Nikolic, D.; Li, Y.; Chadwick, L. R.; Grubjesic, S.; Schwab, P.; Metz, P.; van Breemen, R. B. Metabolism of 8-Prenylnaringenin, a potent phytoetsrogen from hops (Humulus lupulus) by human liver microsomes. Drug Metabol. Dispos. 2004, 32, 272.

Chadwick, L. R.; Fong, H. H. S.; Farnsworth , N. R.; Pauli, G. F. CCC sample cutting for isolation of prenylated phenolics from hops. J. Liq. Chromatogr. Relat. Technol. 2005, 28, 1959-1969.

Dietz, B.; Fey, S.; Pauli, G. F.; Farnsworth, N. R.; Mahady, G. Valerian extract and valerenic acid are partial agonists of the 5HT5A-receptor in vitro. Mol. Brain Res. 2005, 138, 191-197.

Dietz, B.; Kang, Y.-W.; Liu, G.; Eggler, A.; Yao, P.; Chadwick, L.; Pauli, G. F.; Farnsworth, N. R.; Mesecar, A.; van Breemen, R. B.; Bolton, J. Xanthohumol isolated from Humulus lupulus inhibits menadione-induced NDA damage through induction of quinone reductase. Chem. Res. Toxicol. 2005, 18, 1296-1305.

Liu, G.; Eggler, A. L.; Dietz, B. M.; Mesecar, A. D.; Bolton, J. L.; Pezzuto, J. M.; van Breemen, R. B. Screening method for the discovery of potential cancer chemoprevention agents based on mass spectrometric detection of alkylated Keap1. Anal. Chem. 2005, 77, 6407-6414.

Nikolic, D.; Li, Y.; Chadwick, L.; Pauli, G. F. F.; van Breemen, R. B. Metabolism of xanthohumol and isoxanthohumol, prenylated flavonoids from hops (Humulus lupulus L.), by human liver microsomes. J. Mass Spectrom. 2005, 40, 289-299.

Overk, C. R.; Yao, P.; Chadwick, L. R.; Cuendet, M.; Fong, H. H. S.; Pauli, G. F.; Farnsworth , N. R.; Bolton, J. Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense). J. Agric. Food Chem. 2005, 53, 6246-6253.

Chadwick, L.; Pauli, G. F.; Farnsworth, N. R. The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on their estrogenic properties. Phytomedicine 2006, 13, 119-131.

Guo, J.; Nikolic, D.; Chadwick, L. R.; Pauli, G. F.; van Breemen, R. B. Identification of Human Hepatic Cytochrome P450 Enzymes Involved in the Metabolism of 8-Prenylnaringenin and isoxanthohumol from Hops (Humulus lupulus L.). Drug Metabol. Dispos. 2006, 34, 1152.

Nikolic, D.; Li, Y.; Chadwick, L. R.; van Breemen, R. B. In vitro studies of intestinal permeability and hepatic and intestinal metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus L.). Pharm. Res. 2006, 23, 864-872.

Pang, Y.; Nikolic, D.; Zhu, D.; Chadwick, L. R.; Pauli, G. F. F.; Farnsworth, N. R.; van Breemen, R. B. Binding of the hop (Humulus lupulus L.) chalcone xanthohumol to cytosolic proteins in Caco-2 intestinal epithelial cells. Mol. Nutr. Food Res. 2007, 51, 872-879.

Choi, Y.; van Breemen, R. B. Development of a screening assay for ligands to the estrogen receptor based on magnetic microparticles and LC-MS. Comb. Chem. High Throughput Screening 2008, 11, 1-6.

Overk, C. R.; Gao, J.; Lantvit, D. D.; Minassi, A.; Appendino, G.; Pauli, G. F. F.; van Breemen, R. B.; Farnsworth, N. R.; Bolton, J. L. In vivo estrogenic comparisons of Trifolium pratense (red clover), Humulus lupulus (hops), and the pure compounds isoxanthohumol and 8-prenylnarigenin. Chemico-Biological Interactions 2008, 176, 30-39.

Bolca, S.; Li, J.; Nikolic, D.; Roche, N.; Blondeel, P.; Possemiers, S.; De Keukeleire, D.; Bracke, M.; Heyerick, A.; van Breemen, R. B.; Depypere, H. Disposition of hop prenylflavonoids in human breast tissue. Mol. Nutr. Food Res. 2010, 54 Suppl 2, S284-294.

Choi, Y.; Jermihov, K.; Nam, S. J.; Sturdy, M.; Maloney, K.; Qiu, X.; Chadwick, L. R.; Main, M.; Chen, S. N.; Mesecar, A. D.; Farnsworth, N. R.; Pauli, G. F.; Fenical, W.; Pezzuto, J. M.; van Breemen, R. B. Screening natural products for inhibitors of quinone reductase-2 using ultrafiltration LC-MS. Anal. Chem. 2011, 83, 1048-1052.

Madhubhani, P.; Hemachandra, L. P.; Chandrasena, R.; Esala, P.; Chen, S. N.; Main, M.; Lankin, D. C.; Scism, R. A.; Dietz, B. M.; Pauli, G. F.; Thatcher, G. R.; Bolton, J. L. Hops (Humulus lupulus) inhibits oxidative estrogen metabolism and estrogen-induced malignant transformation in human mammary epithelial cells (MCF-10A). Cancer Prevention Research 2012, 5, 73-81.

Yuan, Y.; Qiu, X.; Nikolic, D.; Dahl, J. H.; van Breemen, R. B. Method development and validation for ultra-high-pressure LC/MS/MS determination of hop prenylflavonoids in human serum. J. AOAC Int. 2012, 95, 1744-1749.

Dietz, B.; Hagos, G. K.; Eskra, J. N.; Wijewickrama, G. T.; Anderson, J. R.; Nikolic, D.; Guo, J.; Chen, S.; Pauli, G. F.; van Breemen, R. B.; Bolton, J. L. Differential regulation of detoxification enzymes in hepatic and mammary tissue by hops (Humulus lupulus) in vitro and in vivo. Mol. Nutr. Food Res. 2013, 57, 1055–1066.

Hajirahimkhan, A.; Simmler, C.; Yuan, Y.; Anderson, J. R.; Chen, S.-N.; Nikolić, D.; Dietz, B. M.; Pauli, G. F.; van Breemen, R. B.; Bolton, J. L. Evaluation of estrogenic activity of licorice species in comparison with hops used in botanicals for menopausal symptoms. PLoS ONE 2013, 8, e67947.

Nikolić, D.; van Breemen, R. B. Analytical methods for quantitation of prenylated flavonoids from hops. Curr. Anal. Chem. 2013, 9, 71-85.

Krause, E.; Yuan, Y.; Hajirahimkhan, A.; Dong, H.; Dietz, B. M.; Nikolic, D.; Pauli, G. F.; Bolton, J. L.; van Breemen, R. B. Biological and chemical standardization of a hop (Humulus lupulus) botanical dietary supplement. Biomed. Chromatogr. 2014, 28, 729-734.

Ramos Alvarenga, R. F.; Friesen, J. B.; Nikolić, D.; Simmler, C.; Napolitano, J. G.; van Breemen, R.; Lankin, D. C.; McAlpine, J. B.; Pauli, G. F.; Chen, S.-N. K-Targeted metabolomic profiling extends chemical subtraction to DESIGNER extracts. J. Nat. Prod. 2014, 77, 2595-2604.

van Breemen, R. B.; Yuan, Y.; Banuvar, S.; Shulman, L. P.; Qiu, X.; Chen, S.-N.; Bolton, J. L.; Pauli, G. F.; Krause, E. C.; Viana, M.; Nikolic, D. Pharmacokinetics of prenylated hop phenols from hops in women following oral administration of a standardized extract of hops. Mol. Nutr. Food Res. 2014, 58, 1962-1969.

Yuan, Y.; Qiu, X.; Nikolić, D.; Chen, S.-N.; Huang, K.; Li, G.; Pauli, G. F.; van Breemen, R. B. Inhibition of human cytochrome P450 enzymes by hops (Humulus lupulus) and hop prenylphenols. Eur. J. Pharm. Sci. 2014, 53, 55-61.

Dunlap, T. L.; Wang, S.; Simmler, C.; Chen, S.-N.; Pauli, G. F.; Dietz, B. M.; Bolton, J. L. Differential Effects of Glycyrrhiza Species on Genotoxic Estrogen Metabolism: Licochalcone A Downregulates P450 1B1, whereas Isoliquiritigenin Stimulates It. Chem. Res. Toxicol. 2015, 28, 1584-1594.

Hajirahimkhan, A.; Simmler, C.; Dong, H.; Lantvit, D. D.; Li, G.; Chen, S.-N.; Nikolić, D.; Pauli, G. F.; van Breemen, R. B.; Dietz, B. M.; Bolton, J. L. Induction of NAD(P)H:Quinone Oxidoreductase 1 (NQO1) by Glycyrrhiza Species Used for Women’s Health: Differential Effects of the Michael Acceptors Isoliquiritigenin and Licochalcone A. Chem. Res. Toxicol. 2015, 28, 2130-2141.

Simmler, C.; Chen, S.-N.; Jeff, A.; Lankin, D. C.; Phansalkar, R.; Krause, E.; Dietz, B.; L., B. J.; Nikolic, D.; van Breemen, R. B.; Pauli, G. F. Botanical Integrity: The Importance of the Integration of Chemical, Biological, and Botanical Analyses, and the Role of DNA Barcoding. Herbal Gram 2015, 106, 56-58.

Dietz, B. M.; Hajirahimkhan, A.; Dunlap, T. L.; Bolton, J. L. Botanicals and Their Bioactive Phytochemicals for Women’s Health. Pharmacological Reviews 2016, 68, 1026-1073.

Simmler, C.; Chen, S.-N.; Phansalkar, R.; Soejarto, D. D.; Lankin, D. C.; Krause, E.; Nikolic, D.; van Breemen, R. B.; Dietz, B.; Bolton, J. L.; Pauli, G. F. Botanical Integrity: Part 2. Traditional and Holistic Modern Analytical Approaches. Herbal Gram 2016, 109, 60-64.

Wang, S.; Dunlap, T. L.; Howell, C. E.; Mbachu, O. C.; Rue, E. A.; Phansalkar, R.; Chen, S.-N.; Pauli, G. F.; Dietz, B. M.; Bolton, J. L. Hop (Humulus lupulus L.) Extract and 6-Prenylnaringenin Induce P450 1A1 Catalyzed Estrogen 2-Hydroxylation. Chem. Res. Toxicol. 2016, 29, 1142-1150.

Dietz, B. M.; Chen, S.-N.; Alvarenga, R. F. R.; Dong, H.; Nikolić, D.; Biendl, M.; van Breemen, R. B.; Bolton, J. L.; Pauli, G. F. DESIGNER Extracts as Tools to Balance Estrogenic and Chemopreventive Activities of Botanicals for Women’s Health. J. Nat. Prod. 2017, 80, 2284-2294.

Dunlap, T. L.; Howell, C. E.; Mukand, N.; Chen, S.-N.; Pauli, G. F.; Dietz, B. M.; Bolton, J. L. Red Clover Aryl Hydrocarbon Receptor (AhR) and Estrogen Receptor (ER) Agonists Enhance Genotoxic Estrogen Metabolism. Chem. Res. Toxicol. 2017, 30, 2084-2092.

Keiler, A. M.; Helle, J.; Bader, M. I.; Ehrhardt, T.; Nestler, K.; Kretzschmar, G.; Bernhardt, R.; Vollmer, G.; Nikolić, D.; Bolton, J. L.; Pauli, G. F.; Chen, S.-N.; Dietz, B. M.; van Breemen, R. B.; Zierau, O. A standardized Humulus lupulus (L.) ethanol extract partially prevents ovariectomy-induced bone loss in the rat without induction of adverse effects in the uterus. Phytomedicine 2017, 34, 50-58.

Keiler, A. M.; Macejova, D.; Dietz, B. M.; Bolton, J. L.; Pauli, G. F.; Chen, S. N.; van Breemen, R. B.; Nikolic, D.; Goerl, F.; Muders, M. H.; Zierau, O.; Vollmer, G. Evaluation of estrogenic potency of a standardized hops extract on mammary gland biology and on MNU-induced mammary tumor growth in rats. J. Steroid Biochem. Mol. Biol. 2017, 174, 234-241.

Liu, Y.; Friesen, J. B.; Grzelak, E. M.; Fan, Q.; Tang, T.; Durić, K.; Jaki, B. U.; McAlpine, J. B.; Franzblau, S. G.; Chen, S.-N.; Pauli, G. F. Sweet spot matching: A thin-layer chromatography-based countercurrent solvent system selection strategy. J. Chromatogr. A 2017, 1504, 46-54.

Hajirahimkhan, A.; Mbachu, O.; Simmler, C.; Ellis, S. G.; Dong, H.; Nikolic, D.; Lankin, D. C.; van Breemen, R. B.; Chen, S.-N.; Pauli, G. F.; Dietz, B. M.; Bolton, J. L. Estrogen Receptor (ER) Subtype Selectivity Identifies 8-Prenylapigenin as an ERβ Agonist from Glycyrrhiza inflata and Highlights the Importance of Chemical and Biological Authentication. J. Nat. Prod. 2018, 81, 966-975.

Wang, S.; Dunlap, T. L.; Huang, L.; Liu, Y.; Simmler, C.; Lantvit, D. D.; Crosby, J.; Howell, C. E.; Dong, H.; Chen, S.-N.; Pauli, G. F.; van Breemen, R. B.; Dietz, B. M.; Bolton, J. L. Evidence for Chemopreventive and resilience activity of licorice: Glycyrrhiza glabra and G. inflata extracts modulate estrogen metabolism in ACI rats. Cancer Prevention Research 2018, 11, 819-830.

Bolton, J. L.; Dunlap, T. L.; Hajirahimkhan, A.; Mbachu, O.; Chen, S.-N.; Chadwick, L.; Nikolic, D.; van Breemen, R. B.; Pauli, G. F.; Dietz, B. M. The Multiple Biological Targets of Hops and Bioactive Compounds. Chem. Res. Toxicol. 2019, 32, 222-233.

Fang, J.-B.; Nikolić, D.; Lankin, D. C.; Simmler, C.; Chen, S.-N.; Ramos Alvarenga, R. F.; Liu, Y.; Pauli, G. F.; van Breemen, R. B. Formation of (2R)- and (2S)-8-Prenylnaringenin Glucuronides by Human UDP-Glucuronosyltransferases. J. Agric. Food Chem. 2019, 67, 11650-11656.

Malca Garcia, G. R.; Friesen, J. B.; Liu, Y.; Nikolić, D.; Lankin, D. C.; McAlpine, J. B.; Chen, S.-N.; Pauli, G. F. Preparation of DESIGNER extracts of red clover (Trifolium pratense L.) by centrifugal partition chromatography. J. Chromatogr. A 2019, 1605, 360277.

Chen, L.; Choi, J.; Leonard, S. W.; Banuvar, S.; Barengolts, E.; Viana, M.; Chen, S.-N.; Pauli, G. F.; Bolton, J. L.; van Breemen, R. B. No Clinically Relevant Pharmacokinetic Interactions of a Red Clover Dietary Supplement with Cytochrome P450 Enzymes in Women. J. Agric. Food Chem. 2020, 68, 13929-13939.

Hitzman, R. T.; Dunlap, T. L.; Howell, C. E.; Chen, S.-N.; Vollmer, G.; Pauli, G. F.; Bolton, J. L.; Dietz, B. M. 6-Prenylnaringenin from Hops Disrupts ERα-Mediated Downregulation of CYP1A1 to Facilitate Estrogen Detoxification. Chem. Res. Toxicol. 2020, 33, 2793-2803.

Mbachu, O. C.; Howell, C.; Simmler, C.; Malca Garcia, G. R.; Skowron, K. J.; Dong, H.; Ellis, S. G.; Hitzman, R. T.; Hajirahimkhan, A.; Chen, S.-N.; Nikolic, D.; Moore, T. W.; Vollmer, G.; Pauli, G. F.; Bolton, J. L.; Dietz, B. M. SAR Study on Estrogen Receptor α/β Activity of (Iso)flavonoids: Importance of Prenylation, C-Ring (Un)Saturation, and Hydroxyl Substituents. J. Agric. Food Chem. 2020, 68, 10651-10663.

van Breemen, R. B.; Chen, L.; Tonsing-Carter, A.; Banuvar, S.; Barengolts, E.; Viana, M.; Chen, S.-N.; Pauli, G. F.; Bolton, J. L. Pharmacokinetic Interactions of a Hop Dietary Supplement with Drug Metabolism in Perimenopausal and Postmenopausal Women. J. Agric. Food Chem. 2020, 68, 5212-5220.

Malca-Garcia, G. R.; Liu, Y.; Dong, H.; Nikolić, D.; Friesen, J. B.; Lankin, D. C.; McAlpine, J.; Chen, S.-N.; Dietz, B. M.; Pauli, G. F. Auto-hydrolysis of red clover as “green” approach to (iso)flavonoid enriched products. Fitoterapia 2021, 152, 104878.