 | This articleneeds morereliable medical references forverification or relies too heavily onprimary sources. Please review the contents of the article andadd the appropriate references if you can. Unsourced or poorly sourced material may be challenged andremoved.Find sources: "Genistein" – news ·newspapers ·books ·scholar ·JSTOR(June 2012) |
 | |
 | |
| Names | |
|---|---|
| IUPAC name 4′,5,7-Trihydroxyisoflavone | |
| Systematic IUPAC name 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | |
| Identifiers | |
| |
3D model (JSmol) | |
| 263823 | |
| ChEBI | |
| ChEMBL |
|
| ChemSpider |
|
| DrugBank |
|
| ECHA InfoCard | 100.006.524 |
| EC Number |
|
| KEGG | |
| UNII | |
| |
| |
| Properties | |
| C15H10O5 | |
| Molar mass | 270.240 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Genistein (C15H10O5) is a plant-derived,aglyconeisoflavone.[1] Genistein has the highest content of all isoflavones insoybeans and soy products, such astempeh. As a type ofphytoestrogen, genistein hasestrogenic activity in vitro; consequently, its long-term intake by consuming soy products may affect reproductive organs, such as theuterus andbreast.[1]
It was first isolated in 1899 from thedyer's broom,Genista tinctoria; hence, the chemical name. The compound structure was established in 1926, when it was found to be identical with that ofprunetol. It was chemically synthesized in 1928.[2] Genistein is a primary secondary metabolite of theTrifolium species andGlycine max (soy).
Isoflavones, such as genistein anddaidzein, occur in soybeans and various other plants, includinglupin,fava beans,kudzu,psoralea,[3][4]Flemingia vestita,[5] andcoffee.[6] It is present inred clover.[7]
Isoflavone intake from consuming soy products may be as high as 50 mg per day in Asian cuisines, although it is considerably lower in Western diets.[1] Genistein has the highest percentage among isoflavones in various soy foods, such as protein concentrate, mature soybeans, and tempeh.[1]
Dietary supplements andinfant formulas containing isoflavoneextracts are marketed in some countries.[1]
Pharmacokinetics studies indicate that genistein blood concentrations peak about 6 hours after a meal containing isoflavones, which arehydrolized in thesmall intestine andcolon.[1]
The colonicmicrobiota duringdigestion influences themetabolism of genistein and other isoflavones, converting them to metabolites having potential biological effects, such as the extent of estrogenic activity.[1]
Although soy products aregenerally recognized as safe (GRAS),[8] a GRAS determination specifically for genistein has not been reported.
Because soy isoflavones have similar chemical structure to17-β-estradiol, the potential for genistein as an estrogenic (hormone-like)signaling molecule that binds to estrogen receptors within cells, mimicking the action ofestrogen, has been the subject of research. Estrogenic effects by genistein may affect the risk of hormone-associated cancers in reproductive tissues, such as the breast,uterus orprostate gland, while it may also influencebone density and levels ofblood lipids.[1]
Although the potential for genistein to have diverse biological activity in humans has been extensively studied, there is only limited evidence of its specific effects.[8]
In a 2011-12 analysis, a scientific panel for theEuropean Food Safety Authority found that there was no evidence for acause-and-effect relationship between the consumption of genistein with other soy isoflavones and 1) protection ofDNA,proteins and lipids fromoxidative damage, 2) maintenance of normal bloodLDL-cholesterol concentrations, 3) changes in vascular function associated with menopause, 4) normal hair growth or 5) bone mineral density.[9][10] The panel further concluded that there was insufficient evidence that soy isoflavones could affect normal skin tone, respiratory functions, cardiovascular health, or prostate cancer.[9]
There is preliminary evidence that consuming soy foods rich in genistein and isoflavones may improvecardiovascular function inpostmenopausal women[1] and lower the risk ofbreast cancer in premenopausal and postmenopausal women.[11] Some studies indicate that supplementation with genistein and soy isoflavones may reducehot flashes andnight sweats during menopause, while there is insufficient evidence for an effect onosteoporosis andcognitive function.[1]
In vitro, genistein is anagonist of theG protein-coupled estrogen receptor,[12][13] and binds to and activates all threeperoxisome proliferator-activated receptor isoforms, α, δ, and γ.[14][15] Genistein is atyrosine kinase inhibitor, mostly ofepidermal growth factor receptors.[1]
The root-tuber peel extract ofFlemingia vestita is atraditional medicineanthelmintic of theKhasi tribes of India. In research, genistein was found to be the major isoflavone responsible for adeworming property.[5][16] Genistein was subsequently demonstrated to be effective againstintestinal parasites, such as thepoultrycestodeRaillietina echinobothrida,[16] theporktrematodeFasciolopsis buski,[17] and thesheep liver flukeFasciola hepatica.[18] It exerts its anthelmintic activity by inhibitingenzymes ofglycolysis andglycogenolysis in the parasites.[19][20]
Isoflavones and theirglycosides | |
|---|---|
| Isoflavones | |
| O-methylated isoflavones | |
| Glycosides | |
| Prenylated isoflavones | |
| Pyranoisoflavones | |
| Derivatives | |
| Synthetic | |
