Isoxanthohumol
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| Names | |
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| IUPAC name
7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C21H22O5 | |
| Molar mass | 354.39 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. (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. 136 (7). American Society for Nutrition: 1862–1867.
{{cite journal}}: Explicit use of et al. in:|author=(help); Unknown parameter|month=ignored (help) - ^ Production of 8-Prenylnaringenin from Isoxanthohumol through Biotransformation by Fungi Cells. Ming-liang Fu, Wei Wang, Feng Chen, Ya-chen Dong, Xiao-jie Liu, Hui Ni and Qi-he Chen, J. Agric. Food Chem., 2011, volume 59, issue 13, pages 7419–7426, doi:10.1021/jf2011722
- ^ Disposition of hop prenylflavonoids in human breast tissue. Bolca S, Li J, Nikolic D, Roche N, Blondeel P, Possemiers S, De Keukeleire D, Bracke M, Heyerick A, van Breemen RB and Depypere H, Mol Nutr Food Res., July 2010, volume 54, Supplement 2, pages 284-294, 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". Med Chem Res. doi:10.1007/s00044-011-9967-8. Retrieved 2013-04-07.