Isoxanthohumol: Difference between revisions

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'''Isoxanthohumol''' is a [[prenylflavonoid]], and it is a phytoestrogen. It is abbreviated as '''IX''' or '''IXN'''.
'''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,<ref name="ix8pren">{{cite journal|title=The Prenylflavonoid Isoxanthohumol from Hops (Humulus lupulus L.) Is Activated into the Potent Phytoestrogen 8-Prenylnaringenin In Vitro and in the Human Intestine|url=http://jn.nutrition.org/content/136/7/1862.long |journal=Journal of Nutrition|author=Possemiers et al|year=2006|month=July |volume=136| issue= 7| pages=1862-1867|publisher=American Society for Nutrition }}</ref> and by fungus in cell cultures.<ref>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}}</ref>
[[8-prenylnaringenin]] can be produced from isoxanthohumol by flora in the human intestine,<ref name="ix8pren">{{cite journal|title=The Prenylflavonoid Isoxanthohumol from Hops (Humulus lupulus L.) Is Activated into the Potent Phytoestrogen 8-Prenylnaringenin In Vitro and in the Human Intestine|url=http://jn.nutrition.org/content/136/7/1862.long |journal=Journal of Nutrition|author=Possemiers et al|year=2006|month=July |volume=136| issue= 7| pages=1862-1867|publisher=American Society for Nutrition }}</ref> and by fungi in cell cultures.<ref>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}}</ref>


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.<ref>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}}</ref>
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.<ref>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}}</ref>

Revision as of 10:17, 12 January 2013

Isoxanthohumol
Chemical structure of 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)
  • 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
  • CC(=CCC1=C(C=C(C2=C1OC(CC2=O)C3=CC=C(C=C3)O)OC)O)C
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).

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. At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.[3]

See also

References

  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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