Isoxanthohumol Explained

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 estrogenic 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

Notes and References

1. Possemiers S, Bolca S, Grootaert C, Heyerick A, Decroos K, Dhooge W, De Keukeleire D, Rabot S, Verstraete W, Van de Wiele T. etal . 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 . 1862–7 . 2006 . 16772450 . 10.1093/jn/136.7.1862. free .
2. 10.1021/jf2011722. Production of 8-Prenylnaringenin from Isoxanthohumol through Biotransformation by Fungi Cells. 2011. Fu. Ming-Liang. Wang. Wei. Chen. Feng. Dong. Ya-Chen. Liu. Xiao-jie. Ni. Hui. Chen. Qi-he. Journal of Agricultural and Food Chemistry. 59. 13. 7419–26. 21634799.
3. 10.1002/mnfr.200900519. 20486208. Disposition of hop prenylflavonoids in human breast tissue. 2010. 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. Molecular Nutrition & Food Research. 54. S284–94. 3856213.
4. Anioł M, Swiderska A, Stompor M, Zołnierczyk AK . Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4'-O-substituted isoxanthohumols . Med Chem Res . 21 . 12 . 4230–4238 . 2012 . 23087590 . 3474914 . 10.1007/s00044-011-9967-8.