Formononetin

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Formononetin
Formononetin.svg
Formononetin molecule
Names
IUPAC name
7-hydroxy-3-(4-methoxyphenyl)chromen-4-one
Other names
Biochanin B
Formononetol
7-Hydroxy-4'-methoxyisoflavone
4'-O-methyldaidzein
Identifiers
3D model (Jmol)
237979
ChEBI
ChemSpider
ECHA InfoCard 100.006.931
KEGG
Properties
C16H12O4
Molar mass 268.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Formononetin is an O-methylated isoflavone.

Natural occurrences[edit]

Formononetin is found in a number of plants and herbs like the red clover.[1] Along with other phytoestrogens, it predominantly occurs in leguminous plants and Fabaceae, particularly in beans, such as green beans, lima beans, soy and many others, as the free aglycone or in form of its glucoside ononin.[2]

It can also be found in Maackia amurensis cell cultures.[3]

Metabolism[edit]

The enzyme 4'-methoxyisoflavone 2'-hydroxylase uses formononetin, NADPH, H+, and O2 to produce 2'-hydroxyformononetin, NADP+ and H2O.

The enzyme Isoflavone 3'-hydroxylase uses formononetin, NADPH, H+, and O2 to produce calycosin (3'-hydroxyformononetin), NADP+ and H2O.

Glycosides[edit]

Ononin is the 7-O-glucoside of formononetin.

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. ^ "Iowa State University Database on the Isoflavone Content of Foods, Release 1.3". USDA. 2002. 
  3. ^ Isoflavonoid production by callus cultures of Maackia amurensis. S.A Fedoreyev, T.V Pokushalov, M.V Veselova, L.I Glebko, N.I Kulesh, T.I Muzarok, L.D Seletskaya, V.P Bulgakov and Yu.N Zhuravlev, Fitoterapia, 1 August 2000, Volume 71, Issue 4, Pages 365–372, doi:10.1016/S0367-326X(00)00129-5