Biochanin A: Difference between revisions

| Watchedfields = changed

| verifiedrevid = 443423335

| Name = Biochanin A

| ImageFile = Biochanin A.svg

| ImageSize = 220px

| ImageFile1 = Biochanin-A-3D-balls.png

| ImageSize1 = 220

| ImageAlt1 = Biochanin A molecule

| IUPACName = 5,7-Dihydroxy-4′-methoxyisoflavone

| SystematicName = 5,7-Dihydroxy-3-(4-methoxyphenyl)-4''H''-1-benzopyran-4-one

| OtherNames = Biochanin<br />4′-Methylgenistein<br />olmelin<br />Biochanine A<br />Biochanin-A<br />Genistein 4-methyl ether

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 2829

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = U13J6U390T

| PubChem = 5280373

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 17574

|Section2={{Chembox Properties

| C=16 | H=12 | O=5

| Appearance =

| Density =

| MeltingPt =

| BoilingPt=

| Solubility=

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt=

'''Biochanin A''' is an [[O-methylated isoflavone|''O''-methylated isoflavone]]. It is a natural organic compound in the class of [[phytochemical]]s known as flavonoids. Biochanin A can be found in [[red clover]]<ref>{{ cite journal |author1=Medjakovic, S. |author2=Jungbauer, A. | title = Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor | journal = The Journal of Steroid Biochemistry and Molecular Biology | year = 2008 | volume = 108 | issue = 1–2 | pages = 171–177 | pmid = 18060767 | doi = 10.1016/j.jsbmb.2007.10.001 |s2cid=206495959 }}</ref> in [[soy]], in [[alfalfa]] sprouts, in [[peanut]]s, in [[chickpea]] (''Cicer arietinum'') and in other legumes.

Biochanin A is classified as a [[phytoestrogen]] and has putative benefits in dietary [[List of oncology-related terms|cancer prophylaxis]].{{medcn|date=November 2015}} It has also been found to be a weak [[enzyme inhibitor|inhibitor]] of [[fatty acid amide hydrolase]] ''[[in vitro]]''.<ref>{{cite journal | vauthors=Thors L, Burston JJ, Alter BJ, McKinney MK, Cravatt BF, Ross RA, Pertwee RG, Gereau RW, Wiley JL, Fowler CJ | title = Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase | journal = British Journal of Pharmacology | year = 2010 | volume = 160 | issue = 3 | pages = 549–560 | doi = 10.1111/j.1476-5381.2010.00716.x | pmid = 20590565 | pmc = 2931556 }}</ref>

Biochanin A can block the [[vasoconstriction]] in a dose-dependent manner due to the inhibition of [[L-type calcium channel]]s. Such [[Vasodilation|vasodilatory]] effect, in micromolar concentrations, is of potential clinical interest for the management of [[Cardiovascular disease|cardiovascular pathologies]].<ref>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}}</ref>

==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-<small>D</small>-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-<small>D</small>-glucoside).

* [[Prunetin]]

==References==

{{Reflist}}

{{Isoflavones}}

{{Cannabinoid receptor modulators}}

{{Estrogen receptor modulators}}

{{Estrogen-related receptor modulators}}

[[Category:Aromatase inhibitors]]

[[Category:O-methylated isoflavones]]

[[Category:Phytoestrogens]]

[[Category:Selective ERβ agonists]]