Isoxanthohumol: Difference between revisions

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{{Chembox
{{Chembox
| ImageFile = Isoxanthohumol.svg
| ImageFile = Isoxanthohumol.svg
| ImageSize = 250px
| ImageSize = 250px
| ImageAlt = Chemical structure of isoxanthohumol.
| ImageAlt = Chemical structure of isoxanthohumol.
| IUPACName = 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
| IUPACName = 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo =
| CASNo = 70872-29-6
| CASNo_Ref = {{Cascite|changed|CAS}}
⚫
| 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
| ChEMBL = 492828
⚫
| InChIKey = YKGCBLWILMDSAV-UHFFFAOYSA-N
| PubChem = 513197
| KEGG = C22606
| PubChem = 513197
| SMILES = CC(=CCC1=C(C=C(C2=C1OC(CC2=O)C3=CC=C(C=C3)O)OC)O)C
| ChemSpiderID = 8104156
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}}
| SMILES = O=C2c3c(O[C@H](c1ccc(O)cc1)C2)c(c(O)cc3OC)C\C=C(/C)C
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| Section2 = {{Chembox Properties
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| 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
| Formula = C<sub>21</sub>H<sub>22</sub>O<sub>5</sub>
⚫
| InChIKey = YKGCBLWILMDSAV-SFHVURJKBQ
| MolarMass = 354.39 g/mol
| StdInChI = 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
| ExactMass = 354.146724 u
| StdInChIKey = YKGCBLWILMDSAV-SFHVURJKSA-N
| Appearance =
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}}
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| Density =
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|Section2={{Chembox Properties
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| MeltingPt =
| C=21 | H=22 | O=5
| BoilingPt =
| Solubility =
| Appearance =
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| Density =
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}}
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| MeltingPt =
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| Section3 = {{Chembox Hazards
| MainHazards =
| BoilingPt =
| FlashPt =
| Solubility =
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}}
| Autoignition =
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|Section3={{Chembox Hazards
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}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
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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|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 |vauthors=Possemiers S, Bolca S, Grootaert C, Heyerick A, Decroos K, Dhooge W, De Keukeleire D, Rabot S, Verstraete W, Van de Wiele T|display-authors=etal |title=The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine |journal=Journal of Nutrition |volume=136 |issue=7 |pages=1862–7 |year=2006 |pmid=16772450 |doi= 10.1093/jn/136.7.1862|url=http://jn.nutrition.org/content/136/7/1862.long|doi-access=free }}</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 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>


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 |vauthors=Anioł M, Swiderska A, Stompor M, Zołnierczyk AK |title=Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4'-O-substituted isoxanthohumols |journal=Med Chem Res |volume=21 |issue=12 |pages=4230–4238 |year=2012 |pmid=23087590 |pmc=3474914 |doi=10.1007/s00044-011-9967-8}}</ref>


== See also ==
== See also ==
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[[Category:Flavanones]]
[[Category:Flavanones]]
[[Category:O-Methylated phenols]]
[[Category:O-methylated natural phenols]]
[[Category:Prenylflavonoids]]
[[Category:Prenylflavonoids]]
[[Category:Humulus]]


{{natural-phenol-stub}}
{{aromatic-stub}}

Latest revision as of 06:35, 16 January 2023

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)
ChEMBL
ChemSpider
KEGG
  • 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[edit]

References[edit]

  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: 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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