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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 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>
[[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|pmid=16772450|first2=S|first3=C|first4=A|first5=K|first6=W|first7=D|first8=S|first9=W|first10=T }}</ref> and by fungi in cell cultures.<ref>{{Cite journal|doi=10.1021/jf2011722|title=Production of 8-Prenylnaringenin from Isoxanthohumol through Biotransformation by Fungi Cells|year=2011|last1=Fu|first1=Ming-Liang|last2=Wang|first2=Wei|last3=Chen|first3=Feng|last4=Dong|first4=Ya-Chen|last5=Liu|first5=Xiao-jie|last6=Ni|first6=Hui|last7=Chen|first7=Qi-he|journal=Journal of Agricultural and Food Chemistry|volume=59|issue=13|pages=7419–26|pmid=21634799}}</ref>


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.<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]]. It has limited estogenic activity. At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.<ref>{{Cite journal|doi=10.1002/mnfr.200900519|pmid=20486208|title=Disposition of hop prenylflavonoids in human breast tissue|year=2010|last1=Bolca|first1=Selin|last2=Li|first2=Jinghu|last3=Nikolic|first3=Dejan|last4=Roche|first4=Nathalie|last5=Blondeel|first5=Phillip|last6=Possemiers|first6=Sam|last7=De Keukeleire|first7=Denis|last8=Bracke|first8=Marc|last9=Heyerick|first9=Arne|last10=Van Breemen|first10=Richard B.|last11=Depypere|first11=Herman|journal=Molecular Nutrition & Food Research|volume=54|pages=S284–94}}</ref>


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.<ref>{{cite web | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3474914/ | title=Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4′-O-substituted isoxanthohumols | publisher=Med Chem Res | date=January 7, 2012 | accessdate=2013-04-07 | author=Anioł, Mirosław | doi=10.1007/s00044-011-9967-8}}</ref>
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.<ref>{{cite journal | pmc=3474914 | title=Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4′-O-substituted isoxanthohumols | publisher=Med Chem Res | date=January 7, 2012 | author=Anioł, Mirosław | doi=10.1007/s00044-011-9967-8 | first2=Anna | first3=Monika | first4=Anna Katarzyna | journal=Medicinal Chemistry Research | volume=21 | issue=12 | pages=4230–4238 | pmid=23087590}}</ref>


== See also ==
== See also ==
Line 40: Line 40:


== References ==
== References ==
{{reflist}}
<references/>


{{Xenoestrogens}}
{{Xenoestrogens}}

Revision as of 16:54, 23 November 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. 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

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. PMID 16772450. {{cite journal}}: |first10= missing |last10= (help); |first2= missing |last2= (help); |first3= missing |last3= (help); |first4= missing |last4= (help); |first5= missing |last5= (help); |first6= missing |last6= (help); |first7= missing |last7= (help); |first8= missing |last8= (help); |first9= missing |last9= (help); Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)
  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: S284–94. doi:10.1002/mnfr.200900519. PMID 20486208.
  4. ^ Anioł, Mirosław (January 7, 2012). "Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4′-O-substituted isoxanthohumols". Medicinal Chemistry Research. 21 (12). Med Chem Res: 4230–4238. doi:10.1007/s00044-011-9967-8. PMC 3474914. PMID 23087590. {{cite journal}}: |first2= missing |last2= (help); |first3= missing |last3= (help); |first4= missing |last4= (help)

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