Biochanin Aのソースを表示

{{chembox
| Watchedfields = changed
| verifiedrevid = 443423335
| Name = Biochanin A
| ImageFile = Biochanin A.svg
| ImageSize = 220px
| ImageFile1 = Biochanin-A-3D-balls.png
| ImageSize1 = 220
| ImageAlt1 = Biochanin A molecule
| IUPACName = 5,7-Dihydroxy-4′-methoxyisoflavone
| SystematicName = 5,7-Dihydroxy-3-(4-methoxyphenyl)-4''H''-1-benzopyran-4-one
| OtherNames = Biochanin<br />4′-Methylgenistein<br />olmelin<br />Biochanine A<br />Biochanin-A<br />Genistein 4-methyl ether
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 2829
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444068
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00814
| InChI = 1/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3
| InChIKey = WUADCCWRTIWANL-UHFFFAOYAM
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 131921
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WUADCCWRTIWANL-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 491-80-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = U13J6U390T
| PubChem = 5280373
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17574
| SMILES = O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O
}}
|Section2={{Chembox Properties
| C=16 | H=12 | O=5
| Appearance =
| Density =
| MeltingPt = 
| BoilingPt=
| Solubility=
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt=
  }}
}}

'''Biochanin A''' is an [[O-methylated isoflavone|''O''-methylated isoflavone]]. It is a natural organic compound in the class of [[phytochemical]]s known as flavonoids. Biochanin A can be found in [[red clover]]<ref>{{ cite journal |author1=Medjakovic, S. |author2=Jungbauer, A. | title = Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor | journal = The Journal of Steroid Biochemistry and Molecular Biology | year = 2008 | volume = 108 | issue = 1–2 | pages = 171–177 | pmid = 18060767 | doi = 10.1016/j.jsbmb.2007.10.001 |s2cid=206495959 }}</ref> in [[soy]], in [[alfalfa]] sprouts, in [[peanut]]s, in [[chickpea]] (''Cicer arietinum'') and in other legumes.

Biochanin A is classified as a [[phytoestrogen]] and has putative benefits in dietary [[List of oncology-related terms|cancer prophylaxis]].{{medcn|date=November 2015}} It has also been found to be a weak [[enzyme inhibitor|inhibitor]] of [[fatty acid amide hydrolase]] ''[[in vitro]]''.<ref>{{cite journal | vauthors=Thors L, Burston JJ, Alter BJ, McKinney MK, Cravatt BF, Ross RA, Pertwee RG, Gereau RW, Wiley JL, Fowler CJ | title = Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase | journal = British Journal of Pharmacology | year = 2010 | volume = 160 | issue = 3 | pages = 549–560 | doi = 10.1111/j.1476-5381.2010.00716.x | pmid = 20590565 | pmc = 2931556 }}</ref>

==Metabolism==
The enzyme [[biochanin-A reductase]] uses dihydrobiochanin A and NADP<sup>+</sup> to produce biochanin A, NADPH, and H<sup>+</sup>.  The enzyme [[isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase]] uses malonyl-CoA and biochanin A 7-O-β-<small>D</small>-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-<small>D</small>-glucoside).

==See also==
* [[List of phytochemicals in food]]
* [[Prunetin]]

==References==
{{Reflist}}

{{Isoflavones}}
{{Cannabinoid receptor modulators}}
{{Estrogen receptor modulators}}
{{Estrogen-related receptor modulators}}

[[Category:Aromatase inhibitors]]
[[Category:O-methylated isoflavones]]
[[Category:Phytoestrogens]]
[[Category:Selective ERβ agonists]]
[[Category:4-Methoxyphenyl compounds]]