From Wikipedia, the free encyclopedia
Formononetin
Names
IUPAC name
7-Hydroxy-4′-methoxyisoflavone
Systematic IUPAC name
7-Hydroxy-3-(4-methoxyphenyl)-4H -1-benzopyran-4-one
Other names
Biochanin B Formononetol 4'-O-methyldaidzein
Identifiers
237979
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.006.931
KEGG
UNII
InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
Y Key: HKQYGTCOTHHOMP-UHFFFAOYSA-N
Y InChI=1/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
Key: HKQYGTCOTHHOMP-UHFFFAOYAJ
O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3
Properties
C16 H12 O4
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).
Chemical compound
Formononetin is an
O-methylated isoflavone .
Natural occurrences
Formononetin is found in a number of plants and herbs such as
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]
Pharmacodynamics
Formononetin promotes
angiogenesis .
[4] It is also involved in expressing the gene and proteins that are needed to make
IgE .
[5]
Derivatives
Ononin is the 7-O -β-D -glucopyranoside of formononetin.
[6]
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 .
S2CID
206495959 .
^
"Iowa State University Database on the Isoflavone Content of Foods, Release 1.3" . USDA. 2002. Archived from
the original on 2012-11-02. Retrieved 2011-02-13 .
^ Fedoreyev, S.A; Pokushalova, T.V; Veselova, M.V; Glebko, L.I; Kulesh, N.I; Muzarok, T.I; Seletskaya, L.D; Bulgakov, V.P; Zhuravlev, Yu.N (2000). "Isoflavonoid production by callus cultures of Maackia amurensis". Fitoterapia . 71 (4): 365–72.
doi :
10.1016/S0367-326X(00)00129-5 .
PMID
10925005 .
^ Li, Shang; Dang, Yuanye; Zhou, Xuelin; Huang, Bin; Huang, Xiaohui; Zhang, Zherui; Kwan, Yiu Wa; Chan, Shun Wan; Leung, George Pak Heng; Lee, Simon Ming Yuen; Hoi, Maggie Pui Man (2015).
"Formononetin promotes angiogenesis through the estrogen receptor alpha-enhanced ROCK pathway" . Scientific Reports . 5 : 16815.
Bibcode :
2015NatSR...516815L .
doi :
10.1038/srep16815 .
PMC
4645220 .
PMID
26568398 .
^
"This plant-based compound could finally cure food allergies" . ZME Science . 2022-04-01. Retrieved 2022-04-04 .
^ You-Ping Zhu (1998-05-28).
Chinese Materia Medica: Chemistry, Pharmacology and Applications . CRC Press. p.
622 .
ISBN
9057022850 .