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| Names | |
|---|---|
| IUPAC name 7-(β-D-Glucopyranosyloxy)-4′,5-dihydroxyisoflavone | |
| Systematic IUPAC name 5-Hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one | |
| Other names Genistoside Genistine Genistein 7-glucoside Genistein glucoside Genistein-7-glucoside Genisteol 7-monoglucoside Glucosyl-7-genistein Genistein 7-O-beta-D-glucoside | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.120.406 |
| KEGG |
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| UNII | |
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| Properties | |
| C21H20O10 | |
| Molar mass | 432.37 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Genistin is anisoflavone found in a number of dietary plants likesoy andkudzu. It was first isolated in 1931 from the 90%methanol extract of asoybean meal, when it was found thathydrolysis withhydrochloric acid produced 1mole each ofgenistein andglucose.[1] Chemically it is the 7-O-beta-D-glucoside form ofgenistein and is the predominant form of theisoflavone naturally occurring in plants. In fact, studies in the 1970s revealed that 99% of the isoflavonoid compounds insoy are present as theirglucosides. Theglucosides are converted bydigestive enzymes in thedigestive system to exert their biological effects. Genistin is also converted to a more familiar genistein, thus, the biological activities including antiatherosclerotic,estrogenic andanticancer effects are analogous.
When ingested along the diet, genistin is readily converted to itsaglycone form,genistein. It ishydrolyzed by removing thecovalently boundglucose to formgenistein and thatgenistein is the form of the compound that is absorbed in theintestine and is the form responsible for the biological activities of theisoflavone. The digestive metabolism was first demonstrated in 2002 that the gut microflora played a large role in the conversion of genistin togenistein.[2] It was later found thatenzymes present in the humansmall intestine andliver also have the ability to convert theisoflavone.Hydrolysis actually starts very quickly in thedigestive system once genistin is ingested, conversion begins in the mouth and then continues in thesmall intestine. Moreover, both humansaliva and the intestinal cell-free extract frommice can cause the complete conversion.[2]
Genistin, like genistein, is aphytoestrogen as it was shown to stimulateestrogen-dependentbreast cancer cell growth in vivo. At a concentration of 1200ppm, genistin caused significant increase of growth ofbreast tumors (MCF-7),cellular proliferation and estrogen-responsive pS2 gene expression inmice. Removal of genistin orgenistein from the diet causedtumors to regress.[3]
Genistin and otherisoflavones are demonstrated to be bioactive within the neonatal intestine and may reduce the severity ofrotavirus infections; genistin alone shows inhibition of the viral infectivity by 40-60%.[4]
In vitro study have shown that both genistin andgenistein are capable of enhancingbonemetabolism in the femoral-metaphyseal tissues of elderlyrats.[5] The presence of genistein or genistin in thetissue culture caused a significant increase inalkaline phosphatase activity,deoxyribonucleic acid (DNA) andcalcium contents. The effect of genistein was greater than that of genistin. It is also revealed that genistin has a strong bone loss preventive activity on experimental rats, and is especially enhanced by combination withfructooligosaccharides.[6] The amount of new bone produced by grafting genistin incollagen matrix was compared to the bone produced by collagen matrix alone inNew Zealand white rabbits, and was observed that genistin caused significant increase in bone formation.[7]
