Biochanin A

Biochanin A

Names
IUPAC name 5,7-Dihydroxy-4′-methoxyisoflavone
Systematic IUPAC name 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Other names Biochanin 4′-Methylgenistein olmelin Biochanine A Biochanin-A Genistein 4-methyl ether
Identifiers
CAS Number	491-80-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17574^Y
ChEMBL	ChEMBL131921^Y
ChemSpider	4444068^Y
ECHA InfoCard	100.007.041
IUPHAR/BPS	2829
KEGG	C00814^Y
PubChem CID	5280373
UNII	U13J6U390T^Y
CompTox Dashboard (EPA)	DTXSID1022394
InChI InChI=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^Y Key: WUADCCWRTIWANL-UHFFFAOYSA-N^Y 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 Key: WUADCCWRTIWANL-UHFFFAOYAM
SMILES O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O
Properties
Chemical formula	C16H12O5
Molar mass	284.267 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Biochanin A is an O-methylated isoflavone. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A can be found in red clover^[1] in soy, in alfalfa sprouts, in peanuts, in chickpea (Cicer arietinum) and in other legumes.

Biochanin A is classified as a phytoestrogen. It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro.^[2]

Metabolism

The enzyme biochanin-A reductase converts biochanin A to 2,3-dihydrobiochanin A using nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.^[3]

biochanin A

+ NADPH

 

 

H⁺

 

H⁺

 

 

2,3-dihydrobiochanin A

+ NADP⁺

 

The enzyme isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase uses malonyl-CoA and biochanin A 7-O-β-D-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-D-glucoside).

See also

• List of phytochemicals in food
• Prunetin

References

1. Medjakovic, S.; Jungbauer, A. (2008). "Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor". The Journal of Steroid Biochemistry and Molecular Biology. 108 (1–2): 171–177. doi:10.1016/j.jsbmb.2007.10.001. PMID 18060767. S2CID 206495959.
2. Thors L, Burston JJ, Alter BJ, McKinney MK, Cravatt BF, Ross RA, Pertwee RG, Gereau RW, Wiley JL, Fowler CJ (2010). "Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase". British Journal of Pharmacology. 160 (3): 549–560. doi:10.1111/j.1476-5381.2010.00716.x. PMC 2931556. PMID 20590565.
3. Tiemann K, Hinderer W, Barz W (1987). "Isolation of NADPH:isoflavone oxidoreductase, a new enzyme of pterocarpan biosynthesis in cell suspensions of Cicer arietinum". FEBS Lett. 213 (2): 324–328. doi:10.1016/0014-5793(87)81515-6.