Isoxanthohumol
| Isoxanthohumol | ||
|---|---|---|
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| IUPAC name 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one | ||
| Identifiers | ||
| PubChem | 513197 | |
| Jmol-3D images | Image 1 | |
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| Properties | ||
| Molecular formula | C21H22O5 | |
| Molar mass | 354.39 g/mol | |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Isoxanthohumol is a prenylflavonoid, and it is a phytoestrogen. It is abbreviated as IX or IXN.
8-Prenylnaringenin can be produced from isoxanthohumol by flora in the human intestine,[1] and by fungi in cell cultures.[2]
This prenylflavonoid is found in hops and beer. It has limited estogenic activity. At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.[3]
Derivatives of isoxanthohumol are: 7,4′-Di-O-methylisoxanthohumol; 7-O-methylisoxanthohumol; 7-O-n-pentylisoxanthohumol; 7,4′-di-O-n-pentyl-8-isoxanthohumol; 7,4′-Di-O-allylisoxanthohumol; 7,4′-Di-O-acetylisoxanthohumol; and 7,4′-Di-O-palmitoylisoxanthohumol.[4]
See also
- Xanthohumol, the corresponding prenylated chalcone
References
- ↑ Possemiers et al (July 2006). "The Prenylflavonoid Isoxanthohumol from Hops (Humulus lupulus L.) Is Activated into the Potent Phytoestrogen 8-Prenylnaringenin In Vitro and in the Human Intestine". Journal of Nutrition (American Society for Nutrition) 136 (7): 1862–1867. PMID 16772450.
- ↑ Fu, Ming-Liang; Wang, Wei; Chen, Feng; Dong, Ya-Chen; Liu, Xiao-jie; Ni, Hui; Chen, Qi-he (2011). "Production of 8-Prenylnaringenin from Isoxanthohumol through Biotransformation by Fungi Cells". Journal of Agricultural and Food Chemistry 59 (13): 7419–26. doi:10.1021/jf2011722. PMID 21634799.
- ↑ Bolca, Selin; Li, Jinghu; Nikolic, Dejan; Roche, Nathalie; Blondeel, Phillip; Possemiers, Sam; De Keukeleire, Denis; Bracke, Marc; Heyerick, Arne; Van Breemen, Richard B.; Depypere, Herman (2010). "Disposition of hop prenylflavonoids in human breast tissue". Molecular Nutrition & Food Research 54: S284–94. doi:10.1002/mnfr.200900519. PMID 20486208.
- ↑ Anioł, Mirosław (January 7, 2012). "Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4′-O-substituted isoxanthohumols". Medicinal Chemistry Research (Med Chem Res) 21 (12): 4230–4238. doi:10.1007/s00044-011-9967-8. PMC 3474914. PMID 23087590.
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