Biochanin A

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Biochanin A
Biochanin A.svg
Biochanin A molecule
Names
IUPAC name
5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
Other names
Biochanin
4'-Methylgenistein
olmelin
Biochanine A
Biochanin-A
Genistein 4-methyl ether
5,7-Dihydroxy-4'-methoxyisoflavone
Identifiers
491-80-5 YesY
ChEBI CHEBI:17574 YesY
ChEMBL ChEMBL131921 YesY
ChemSpider 4444068 YesY
2829
Jmol-3D images Image
KEGG C00814 YesY
PubChem 5280373
Properties
C16H12O5
Molar mass 284.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what isYesY/N?)
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 and has putative benefits in dietary cancer prophylaxis. It has also been found to inhibit fatty acid amide hydrolase[2] and to act as agonist of PPARgamma, nuclear receptor that is current pharmacological target for the treatment of diabetes type 2.[3]

Metabolism[edit]

The enzyme biochanin-A reductase uses dihydrobiochanin A and NADP+ to produce biochanin A, NADPH, and H+.

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).

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. 
  2. ^ Thors, L.; Burston, J. J.; Alter, B. J.; McKinney, M. K.; Cravatt, B. F.; Ross, R. A.; Pertwee, R. G.; Gereau, R. W. 4th; Wiley, J. L.; Fowler, C. J. (2010). "Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase" (pdf). British Journal of Pharmacology 160 (3): 549–560. doi:10.1111/j.1476-5381.2010.00716.x. PMC 2931556. PMID 20590565. 
  3. ^ Wang L, Waltenberger B, Pferschy-Wenzig EM, Blunder M, Liu X, Malainer C, Blazevic T, Schwaiger S, Rollinger JM, Heiss EH, Schuster D, Kopp B, Bauer R, Stuppner H, Dirsch VM, Atanasov AG. Natural product agonists of peroxisome proliferator-activated receptor gamma (PPARγ): a review. Biochem Pharmacol. 2014 Jul 29. pii: S0006-2952(14)00424-9. doi: 10.1016/j.bcp.2014.07.018. PubMed PMID 25083916.

See also[edit]