Isoxanthohumol

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Isoxanthohumol
Isoxanthohumol.svg
Names
IUPAC name
7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3/t18-/m0/s1
    Key: YKGCBLWILMDSAV-SFHVURJKSA-N
  • InChI=1/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3/t18-/m0/s1
    Key: YKGCBLWILMDSAV-SFHVURJKBQ
  • O=C2c3c(O[C@H](c1ccc(O)cc1)C2)c(c(O)cc3OC)C\C=C(/C)C
Properties
C21H22O5
Molar mass 354.402 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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, 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): 1862–7. doi: 10.1093/jn/136.7.1862 . PMID   16772450.
  2. ↑ 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.
  3. ↑ 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 (2): S284–94. doi:10.1002/mnfr.200900519. PMC   3856213 . PMID   20486208.
  4. ↑ Anioł M, Swiderska A, Stompor M, Zołnierczyk AK (2012). "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. doi:10.1007/s00044-011-9967-8. PMC   3474914 . PMID   23087590.
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