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Chemical Compound Review

Xanthohumol     (E)-1-[2,4-dihydroxy-6- methoxy-3-(3...

Synonyms: AC1LCYZZ, CHEMBL253896, CHEBI:66331, X0379_SIGMA, MEGxp0_000104, ...
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Disease relevance of Xanthohumol

  • 8. Xanthohumol also inhibited HIV-1 replication in PBMC with EC50 value of 20.74 microg/ml [1].
  • Distinct modulation of alkaline phosphatase isoenzymes by 17beta-estradiol and xanthohumol in breast cancer MCF-7 cells [2].
  • The purpose of this study was to investigate the anti-tumorigenic effects of xanthohumol (XN), the major prenylflavonoid in hops, on prostate cancer and benign prostate hyperplasia [3].
  • A xanthohumol-enriched hop extract displayed a weak to moderate antiviral activity against BVDV (therapeutic index (TI)=6.0), HSV-2 (TI=>5.3), Rhino (TI=4.0) and HSV-1 (TI=>1.9) with IC(50) values in the low microg/ml range [4].
  • Ultra-pure preparations (>99% pure) were used to show that xanthohumol accounted for the antiviral activity observed in the xanthohumol-enriched hop extract against BVDV, HSV-1 and HSV-2 [4].

High impact information on Xanthohumol


Chemical compound and disease context of Xanthohumol


Biological context of Xanthohumol


Anatomical context of Xanthohumol


Associations of Xanthohumol with other chemical compounds


Gene context of Xanthohumol

  • 3. At 10 microM, XN completely eliminated CYP1B1 EROD activity, whereas the other hop flavonoids showed varying degrees of inhibitory action ranging from 99.3 to 1.8% [17].
  • We have examined the modulating action of xanthohumol (XN) on the farnesoid X receptor (FXR) in vitro and in vivo [20].
  • The chalcones, including xanthohumol, significantly inhibited the production of NO by suppressing the expression of iNOS [21].
  • Xanthohumol, a novel anti-HIV-1 agent purified from Hops Humulus lupulus [1].
  • Lager beer, alcohol-free beer, stout beer, and xanthohumol-rich stout beer (200 microL/mL) significantly decreased aromatase activity [22].

Analytical, diagnostic and therapeutic context of Xanthohumol

  • In this work, we analyzed the influence of xanthohumol (XN), a prenylated chalcone from hops (Humulus lupulus L.), on the I(-) uptake in a cell culture model of normal, nontransformed rat thyrocytes (FRTL-5) [23].


  1. Xanthohumol, a novel anti-HIV-1 agent purified from Hops Humulus lupulus. Wang, Q., Ding, Z.H., Liu, J.K., Zheng, Y.T. Antiviral Res. (2004) [Pubmed]
  2. Distinct modulation of alkaline phosphatase isoenzymes by 17beta-estradiol and xanthohumol in breast cancer MCF-7 cells. Guerreiro, S., Monteiro, R., Martins, M.J., Calhau, C., Azevedo, I., Soares, R. Clin. Biochem. (2007) [Pubmed]
  3. Xanthohumol, a prenylflavonoid derived from hops induces apoptosis and inhibits NF-kappaB activation in prostate epithelial cells. Colgate, E.C., Miranda, C.L., Stevens, J.F., Bray, T.M., Ho, E. Cancer Lett. (2007) [Pubmed]
  4. Antiviral activity of hop constituents against a series of DNA and RNA viruses. Buckwold, V.E., Wilson, R.J., Nalca, A., Beer, B.B., Voss, T.G., Turpin, J.A., Buckheit, R.W., Wei, J., Wenzel-Mathers, M., Walton, E.M., Smith, R.J., Pallansch, M., Ward, P., Wells, J., Chuvala, L., Sloane, S., Paulman, R., Russell, J., Hartman, T., Ptak, R. Antiviral Res. (2004) [Pubmed]
  5. Screening method for the discovery of potential cancer chemoprevention agents based on mass spectrometric detection of alkylated Keap1. Liu, G., Eggler, A.L., Dietz, B.M., Mesecar, A.D., Bolton, J.L., Pezzuto, J.M., van Breemen, R.B. Anal. Chem. (2005) [Pubmed]
  6. Antiinvasive effect of xanthohumol, a prenylated chalcone present in hops (Humulus lupulus L.) and beer. Vanhoecke, B., Derycke, L., Van Marck, V., Depypere, H., De Keukeleire, D., Bracke, M. Int. J. Cancer (2005) [Pubmed]
  7. Inhibition of peroxynitrite-mediated LDL oxidation by prenylated flavonoids: the alpha,beta-unsaturated keto functionality of 2'-hydroxychalcones as a novel antioxidant pharmacophore. Stevens, J.F., Miranda, C.L., Frei, B., Buhler, D.R. Chem. Res. Toxicol. (2003) [Pubmed]
  8. In vitro glucuronidation of xanthohumol, a flavonoid in hop and beer, by rat and human liver microsomes. Yilmazer, M., Stevens, J.F., Buhler, D.R. FEBS Lett. (2001) [Pubmed]
  9. Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines. Delmulle, L., Bellahc??ne, A., Dhooge, W., Comhaire, F., Roelens, F., Huvaere, K., Heyerick, A., Castronovo, V., De Keukeleire, D. Phytomedicine (2006) [Pubmed]
  10. Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines. Miranda, C.L., Stevens, J.F., Helmrich, A., Henderson, M.C., Rodriguez, R.J., Yang, Y.H., Deinzer, M.L., Barnes, D.W., Buhler, D.R. Food Chem. Toxicol. (1999) [Pubmed]
  11. Comparative chemical attributes of native North American hop, Humulus lupulus var. lupuloides E. Small. Hampton, R., Nickerson, G., Whitney, P., Haunold, A. Phytochemistry (2002) [Pubmed]
  12. Xanthohumol kills B-chronic lymphocytic leukemia cells by an apoptotic mechanism. Lust, S., Vanhoecke, B., Janssens, A., Philippe, J., Bracke, M., Offner, F. Molecular nutrition & food research. (2005) [Pubmed]
  13. Plant polyphenols and multidrug resistance: effects of dietary flavonoids on drug transporters in Caco-2 and MDCKII-MDR1 cell transport models. Rodriguez-Proteau, R., Mata, J.E., Miranda, C.L., Fan, Y., Brown, J.J., Buhler, D.R. Xenobiotica (2006) [Pubmed]
  14. Prenylated chalcones and flavanones as inducers of quinone reductase in mouse Hepa 1c1c7 cells. Miranda, C.L., Aponso, G.L., Stevens, J.F., Deinzer, M.L., Buhler, D.R. Cancer Lett. (2000) [Pubmed]
  15. Metabolism of xanthohumol and isoxanthohumol, prenylated flavonoids from hops (Humulus lupulus L.), by human liver microsomes. Nikolic, D., Li, Y., Chadwick, L.R., Pauli, G.F., van Breemen, R.B. Journal of mass spectrometry : JMS. (2005) [Pubmed]
  16. Formation and accumulation of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol during flowering of hops (Humulus lupulus L.). De Keukeleire, J., Ooms, G., Heyerick, A., Roldan-Ruiz, I., Van Bockstaele, E., De Keukeleire, D. J. Agric. Food Chem. (2003) [Pubmed]
  17. In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus. Henderson, M.C., Miranda, C.L., Stevens, J.F., Deinzer, M.L., Buhler, D.R. Xenobiotica (2000) [Pubmed]
  18. Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense). Overk, C.R., Yao, P., Chadwick, L.R., Nikolic, D., Sun, Y., Cuendet, M.A., Deng, Y., Hedayat, A.S., Pauli, G.F., Farnsworth, N.R., van Breemen, R.B., Bolton, J.L. J. Agric. Food Chem. (2005) [Pubmed]
  19. EST analysis of hop glandular trichomes identifies an O-methyltransferase that catalyzes the biosynthesis of xanthohumol. Nagel, J., Culley, L.K., Lu, Y., Liu, E., Matthews, P.D., Stevens, J.F., Page, J.E. Plant. Cell (2008) [Pubmed]
  20. Xanthohumol, the chalcone from beer hops (Humulus lupulus L.), is the ligand for farnesoid X receptor and ameliorates lipid and glucose metabolism in KK-A(y) mice. Nozawa, H. Biochem. Biophys. Res. Commun. (2005) [Pubmed]
  21. Inhibitors of nitric oxide production from hops (Humulus lupulus L.). Zhao, F., Nozawa, H., Daikonnya, A., Kondo, K., Kitanaka, S. Biol. Pharm. Bull. (2003) [Pubmed]
  22. Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity. Monteiro, R., Becker, H., Azevedo, I., Calhau, C. J. Agric. Food Chem. (2006) [Pubmed]
  23. Xanthohumol stimulates iodide uptake in rat thyroid-derived FRTL-5 cells. Radović, B., Schmutzler, C., Köhrle, J. Molecular nutrition & food research. (2005) [Pubmed]
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