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Biochanin A

From Wikipedia, the free encyclopedia
(Redirected from Biochanin)
Biochanin A
Biochanin A molecule
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.041 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: WUADCCWRTIWANL-UHFFFAOYSA-N checkY
  • 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
  • O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O
Properties
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).
checkY verify (what is checkYX markN ?)

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

[edit]

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

2D representation of the chemical structure of biochanin A .
biochanin A
+ NADPH
 
 
H+
 
Reversible left-right reaction arrow with minor forward substrate(s) from top left and minor reverse product(s) to bottom left
H+
 
 
2D representation of the chemical structure of Q27098201.
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

[edit]

References

[edit]
  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.
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