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
CAS Number	70872-29-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL492828;
ChemSpider	8104156;
KEGG	C22606;
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/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;
	SMILES O=C2c3c(O[C@H](c1ccc(O)cc1)C2)c(c(O)cc3OC)C\C=C(/C)C;
Properties
Chemical formula	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). Infobox references

Browse history interactively

← Previous edit

Content deleted Content added

VisualWikitext

Inline

Latest revision as of 06:35, 16 January 2023

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]

References[edit]

^ 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.
^ 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 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.

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

[ix8pren-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.

[1]

[2]

[3]

[4]

@@ Line 6: / Line 6: @@
 | OtherNames =
 |Section1={{Chembox Identifiers
-| CASNo =
+| CASNo = 70872-29-6
+| CASNo_Ref = {{Cascite|changed|CAS}}
+| ChEMBL = 492828
+| KEGG = C22606
 | PubChem = 513197
 | ChemSpiderID = 8104156
 | SMILES = O=C2c3c(O[C@H](c1ccc(O)cc1)C2)c(c(O)cc3OC)C\C=C(/C)C
@@ Line 15: / Line 17: @@
 | 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
 | StdInChIKey = YKGCBLWILMDSAV-SFHVURJKSA-N
+}}
-  }}
 |Section2={{Chembox Properties
+| C=21 | H=22 | O=5
-| Formula = C<sub>21</sub>H<sub>22</sub>O<sub>5</sub>
-| MolarMass = 354.39 g/mol
 | Appearance =
 | Density =
@@ Line 25: / Line 25: @@
 | BoilingPt =
 | Solubility =
-  }}
+}}
 |Section3={{Chembox Hazards
 | MainHazards =
 | FlashPt =
 | AutoignitionPt =
-  }}
+}}
 }}
 '''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 |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}}</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|pmc=3856213}}</ref>
@@ Line 50: / Line 50: @@
 [[Category:Flavanones]]
-[[Category:O-Methylated natural phenols]]
+[[Category:O-methylated natural phenols]]
 [[Category:Prenylflavonoids]]
+[[Category:Humulus]]
-{{natural-phenol-stub}}
+{{aromatic-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

Latest revision as of 06:35, 16 January 2023

See also[edit]

References[edit]