Isoxanthohumol: Difference between revisions
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[[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|date=July 2006 |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> |
[[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|date=July 2006 |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> |
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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.<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> |
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.<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|pmc=3856213}}</ref> |
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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> |
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> |
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Revision as of 15:13, 22 November 2014
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| Names | |
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| IUPAC name
7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| 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).
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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
References
- ^ Possemiers; et al. (July 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) - ^ 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.
- ^ 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. PMC 3856213. PMID 20486208.
- ^ 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.
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