Biochanin A

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Biochanin A
Biochanin A.svg
Biochanin A molecule
Identifiers
CAS number 491-80-5 YesY
PubChem 5280373
ChemSpider 4444068 YesY
KEGG C00814 YesY
ChEBI CHEBI:17574 YesY
ChEMBL CHEMBL131921 YesY
Jmol-3D images Image 1
Properties
Molecular formula C16H12O5
Molar mass 284.26 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/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]

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. 

See also[edit]