Chemistry:Biochanin A
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| IUPAC name
5,7-Dihydroxy-4′-methoxyisoflavone
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| 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 | |
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3D model (JSmol)
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PubChem CID
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| 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). | |
 verify (what is   ?)
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| 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 be a weak inhibitor of fatty acid amide hydrolase in vitro.[2]
Biochanin A can block the vasoconstriction in a dose-dependent manner due to the inhibition of L-type calcium channels. Such vasodilatory effect, in micromolar concentrations, is of potential clinical interest for the management of cardiovascular pathologies.[3]
Metabolism
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).
See also
References
- ↑ 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.
- ↑ "Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase". British Journal of Pharmacology 160 (3): 549–560. 2010. doi:10.1111/j.1476-5381.2010.00716.x. PMID 20590565.
- ↑ Migkos, T., Pourová, J., Vopršalová, M., Auger, C., Schini-Kerth, V., & Mladěnka, P. (2020). "Biochanin A, the Most Potent of 16 Isoflavones, Induces Relaxation of the Coronary Artery Through the Calcium Channel and cGMP-dependent Pathway". Planta medica, 86(10), 708-716. PMID 32408360 doi:10.1055/a-1158-9422
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