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Chemical Compound Review:

Isoxanthohumol 7-hydroxy-2-(4- hydroxyphenyl)-5-methoxy-8...

Synonyms: CHEMBL492828, SureCN904557, AG-L-65853, CHEBI:568668, AC1LAG2U, ...

Delmulle, L. et al., Bertl, E. et al., Coldham, N.G. et al., Miranda, C.L. et al., Henderson, M.C. et al., et al.

Coldham, Horton, Byford, Sauer, Monteiro, Becker, Azevedo, Calhau,

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Disease relevance of AIDS-188437

Chalcones xanthohumol (X) and desmethylxanthohumol (DMX), present in hops (Humulus lupulus L.), and the corresponding flavanones isoxanthohumol (IX, from X), 8-prenylnaringenin (8-PN, from DMX), and 6-prenylnaringenin (6-PN, from DMX), have been examined in vitro for their anti-proliferative activity on human prostate cancer cells PC-3 and DU145 [1].

High impact information on AIDS-188437

The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine [2].
Except for the formation of minor nitrated products, IsoXN remained largely unmodified upon treatment with SIN-1/peroxynitrite [3].
Identification of human hepatic cytochrome P450 enzymes involved in the metabolism of 8-prenylnaringenin and isoxanthohumol from hops (Humulus lupulus L.) [4].
Metabolism of xanthohumol and isoxanthohumol, prenylated flavonoids from hops (Humulus lupulus L.), by human liver microsomes [5].
These include the monoacylphloroglucinol isoaspidinol B, 1,2,5,7-tetrahydroxy-anthraquinone, peracetylated carnosic acid (PCA), isoxanthohumol, 2,2',4'-trimethoxychalcone, 3'-bromo-2,4-dimethoxychalcone as well as four synthetic derivatives of lunularic acid, a bibenzyl found in mosses [Int. J. Cancer Prev. 1 (2004) 47] [6].

Biological context of AIDS-188437

Thus, xanthohumol, isoxanthohumol, and prenylflavanones 8-prenylnaringenin are potent inhibitors of the metabolic activation of IQ and may have the potential to act as chemopreventive agents against cancer induced by heterocyclic amines activated by CYP1A2 [7].

Associations of AIDS-188437 with other chemical compounds

The oestrogenic potency values for reference standards determined with the RCBA (17beta-oestradiol = 100%) were: methoxychlor 0.0025%, mestranol 1.3%, isoxanthohumol 0.001%, and for their potential respective metabolites were: bishydroxymethoxychlor 0.015%, 17alpha-ethynyl oestradiol 69% and 8-prenylnaringenin 0.4% [8].

Gene context of AIDS-188437

4. In contrast, the most effective inhibitors of CYP1A2 acetanilide 4-hydroxylase activity were the two prenylated flavonoids, 8-prenylnaringenin (8PN) and isoxanthohumol (IX), which produced > 90% inhibition when added at concentrations of 10 microM [9].
The aim of this work was to study the effect of the prenylflavonoids xanthohumol, isoxanthohumol, and 8-prenylnaringenin on the activity and expression of the enzyme aromatase (estrogen synthase) [10].

References

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]
The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine. Possemiers, S., Bolca, S., Grootaert, C., Heyerick, A., Decroos, K., Dhooge, W., De Keukeleire, D., Rabot, S., Verstraete, W., Van de Wiele, T. J. Nutr. (2006) [Pubmed]
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]
Identification of human hepatic cytochrome P450 enzymes involved in the metabolism of 8-prenylnaringenin and isoxanthohumol from hops (Humulus lupulus L.). Guo, J., Nikolic, D., Chadwick, L.R., Pauli, G.F., van Breemen, R.B. Drug Metab. Dispos. (2006) [Pubmed]
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]
Inhibition of endothelial cell functions by novel potential cancer chemopreventive agents. Bertl, E., Becker, H., Eicher, T., Herhaus, C., Kapadia, G., Bartsch, H., Gerhäuser, C. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
Prenylflavonoids from hops inhibit the metabolic activation of the carcinogenic heterocyclic amine 2-amino-3-methylimidazo[4, 5-f]quinoline, mediated by cDNA-expressed human CYP1A2. Miranda, C.L., Yang, Y.H., Henderson, M.C., Stevens, J.F., Santana-Rios, G., Deinzer, M.L., Buhler, D.R. Drug Metab. Dispos. (2000) [Pubmed]
A binary screening assay for pro-oestrogens in food: metabolic activation using hepatic microsomes and detection with oestrogen sensitive recombinant yeast cells. Coldham, N.G., Horton, R., Byford, M.F., Sauer, M.J. Food additives and contaminants. (2002) [Pubmed]
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]
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]

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