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Biochanin A

From Wikipedia, the free encyclopedia
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 InfoCard100.007.041Edit 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 mass284.267 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Biochanin A is anO-methylated isoflavone. It is a natural organic compound in the class ofphytochemicals known as flavonoids. Biochanin A can be found inred clover[1] insoy, inalfalfa sprouts, inpeanuts, inchickpea (Cicer arietinum) and in other legumes.

Biochanin A is classified as aphytoestrogen and has putative benefits in dietarycancer prophylaxis.[medical citation needed] It has also been found to be a weakinhibitor offatty acid amide hydrolasein vitro.[2]

Metabolism

[edit]

The enzymebiochanin-A reductase uses dihydrobiochanin A and NADP+ to produce biochanin A, NADPH, and H+. The enzymeisoflavone-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.
Isoflavones and theirglycosides
Isoflavones
O-methylated isoflavones
Glycosides
Prenylated isoflavones
Pyranoisoflavones
Derivatives
Synthetic
Receptor
(ligands)
CB1Tooltip Cannabinoid receptor type 1
Agonists
(abridged,
full list)
Inverse agonists
Antagonists
CB2Tooltip Cannabinoid receptor type 2
Agonists
Antagonists
NAGly
(
GPR18)
Agonists
Antagonists
GPR55
Agonists
Antagonists
GPR119
Agonists
Transporter
(modulators)
eCBTsTooltip Endocannabinoid transporter
Enzyme
(modulators)
FAAHTooltip Fatty acid amide hydrolase
MAGL
ABHD6
ABHD12
Others
  • Others:2-PG(directly potentiates activity of 2-AG at CB1 receptor)
  • ARN-272(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
ERRαTooltip Estrogen-related receptor alpha
ERRβTooltip Estrogen-related receptor beta
ERRγTooltip Estrogen-related receptor gamma
Retrieved from "https://en.wikipedia.org/w/index.php?title=Biochanin_A&oldid=1247279846"
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