Isoxanthohumol: Difference between revisions

Isoxanthohumol
Names
	IUPAC name 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Identifiers
3D model (JSmol)	Interactive image;
PubChem CID	513197;
	InChI 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 Key: YKGCBLWILMDSAV-UHFFFAOYSA-N;
	SMILES CC(=CCC1=C(C=C(C2=C1OC(CC2=O)C3=CC=C(C=C3)O)OC)O)C;
Properties
Chemical formula	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). Infobox references

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Revision as of 08:51, 12 January 2013

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 fungus in cell cultures.^[2]

Prenylflavonoids are phytoestogens. This prenylflavonoid is found in hops and beer. At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.^[3]

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

Template:Natural-phenol-stub

[ix8pren-1] 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)

[2] 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

[3] 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

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 {{Xenoestrogens}}
+{{Flavanone}}
 [[Category:Prenylflavonoids]]
+[[Category:Flavanones]]
 {{natural-phenol-stub}}

v t e Flavanones and their glycosides
Flavanones	Butin Eriodictyol Naringenin Pinocembrin
O-methylated flavanones	Alpinetin Hesperetin Homoeriodictyol Isosakuranetin Pinostrobin (Pinocembrin-7-methylether) Sakuranetin Sterubin
C-methylated flavanones	Poriol
Glycosides	Eriocitrin Neoeriocitrin Hesperidin Liquiritin Naringin (Narigenin 7-O-neohesperidoside) Narirutin (Naringenin 7-O-rutinoside) Poncirin Prunin (Naringenin-7-O-glucoside) Sakuranin
Acetylated	8-Prenylnaringenin Isoxanthohumol Sophoraflavanone G
Acetylated glycosides	Nirurin