Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H20O10 |
| Molecular Weight | 432.3775 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@@H](OC2=CC3=C(C(=O)C(=CO3)C4=CC=C(O)C=C4)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI
InChIKey=ZCOLJUOHXJRHDI-CMWLGVBASA-N
InChI=1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20-,21-/m1/s1
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20036920 | https://www.ncbi.nlm.nih.gov/pubmed/20132047 | https://www.ncbi.nlm.nih.gov/pubmed/9546622 |
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20036920 | https://www.ncbi.nlm.nih.gov/pubmed/20132047 | https://www.ncbi.nlm.nih.gov/pubmed/9546622 |
Genistin is an 7-O-beta-D-glucosideform of genistein and is the predominant form of the isoflavone naturally occurring in a number of dietary plants like soy and kudzu. In vitro study have shown that both genistin and genistein are capable of enhancing bone metabolism in the femoral-metaphyseal tissues of elderly rats. The presence of genistein or genistin in the tissue culture caused a significant increase in alkaline phosphatase activity, deoxyribonucleic acid (DNA) and calcium 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 with fructooligosaccharides. The amount of new bone produced by grafting genistin in collagenmatrix was compared to the bone produced by collagen matrix alone in New Zealand White rabbits, and was observed that genistin caused significant increase in bone formation.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Genistin inhibits UV light-induced plasmid DNA damage and cell growth in human melanoma cells. | 2006-02 |
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| Flavonoids as a novel class of human organic anion-transporting polypeptide OATP1B1 (OATP-C) modulators. | 2005-11 |
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| Selective inhibitors of terminal deoxyribonucleotidyltransferase (TdT): baicalin and genistin. | 2005-10-10 |
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| Effect of daidzin, genistin, and glycitin on osteogenic and adipogenic differentiation of bone marrow stromal cells and adipocytic transdifferentiation of osteoblasts. | 2005-09 |
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| Dexamethasone and cardiac potassium currents in the diabetic rat. | 2005-09 |
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| Determination of isoflavones in soy bits by fast column high-performance liquid chromatography coupled with UV-visible diode-array detection. | 2005-08-19 |
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| Glycosylation of genistin into soluble inclusion complex form of cyclic glucans by enzymatic modification. | 2005-08-10 |
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| Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones. | 2005-08 |
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| Evaluation of isoflavone aglycon and glycoside distribution in soy plants and soybeans by fast column high-performance liquid chromatography coupled with a diode-array detector. | 2005-07-27 |
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| Antipyretic, analgesic and muscle relaxant activities of pueraria isoflavonoids and their metabolites from Pueraria lobata Ohwi-a traditional Chinese drug. | 2005-07 |
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| Antioxidant enzymes and isoflavonoids in chilled soybean (Glycine max (L.) Merr.) seedlings. | 2005-04 |
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| Pharmacokinetics of a slow-release formulation of soybean isoflavones in healthy postmenopausal women. | 2005-03-23 |
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| Pharmacokinetics of isoflavones, daidzein and genistein, after ingestion of soy beverage compared with soy extract capsules in postmenopausal Thai women. | 2005-03-03 |
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| Flavonoids differentially modulate nitric oxide production pathways in lipopolysaccharide-activated RAW264.7 cells. | 2005-03 |
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| Simultaneous determination of phytoestrogens in different medicinal parts of Sophora japonica L. by capillary electrophoresis with electrochemical detection. | 2005-03 |
|
| Effect of temperature, elevated carbon dioxide, and drought during seed development on the isoflavone content of dwarf soybean [Glycine max (L.) Merrill] grown in controlled environments. | 2005-02-23 |
|
| Assessment of estrogenic activity of flavonoids from Mediterranean plants using an in vitro short-term test. | 2005-01 |
|
| Cumulative dietary energy intake determines the onset of puberty in female rats. | 2004-11 |
|
| The protein tyrosine kinase inhibitor, genistein, decreases excitability of nociceptive neurons. | 2004-11 |
|
| Soy isoflavones suppress invasiveness of breast cancer cells by the inhibition of NF-kappaB/AP-1-dependent and -independent pathways. | 2004-11 |
|
| Isoflavonoids in the Rutaceae family: 1. Fortunella obovata, Murraya paniculata and four Citrus species. | 2004-10-29 |
|
| Phloridzin improves absorption of genistin in isolated rat small intestine. | 2004-10 |
|
| Soy processing influences growth of estrogen-dependent breast cancer tumors. | 2004-09 |
|
| [Azoic color reaction of flavonoids and their analytical application]. | 2004-08 |
|
| Flavonoids of an extract of Pterospartum tridentatum showing endothelial protection against oxidative injury. | 2004-08 |
|
| Enhancement of tofu isoflavone recovery by pretreatment of soy milk with koji enzyme extract. | 2004-07-28 |
|
| Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. | 2004-07 |
|
| Effects of dose and glycosylation on the transfer of genistein into the eggs of the Japanese quail (Coturnix japonica). | 2004-04-21 |
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| Effect of water-to-bean ratio on the contents and compositions of isoflavones in tofu. | 2004-04-21 |
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| Purification and characterization of an isoflavone-conjugates-hydrolyzing beta-glucosidase from endophytic bacterium. | 2004-04-07 |
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| Cytotoxic effects of some animal and vegetable extracts and some chemicals on liver and colon carcinoma and myosarcoma. | 2004-02 |
|
| Use of reporter cell lines for detection of endocrine-disrupter activity. | 2004-02 |
|
| Cytostatic and cytotoxic activity of synthetic genistein glycosides against human cancer cell lines. | 2004-01-08 |
|
| Simultaneous determination of isoflavones and bisphenol A in rat serum by high-performance liquid chromatography coupled with coulometric array detection. | 2004-01 |
|
| Novel physiological function of fructooligosaccharides. | 2004 |
|
| Kudzu root extract suppresses voluntary alcohol intake and alcohol withdrawal symptoms in P rats receiving free access to water and alcohol. | 2004 |
|
| Soybean isoflavones inhibit estrogen-stimulated gene expression in mouse uteri. | 2004 |
|
| [Study of the methods of determining the isoflavones in herbs of Trifolium pratense extractive]. | 2003-11 |
|
| Antitumor-promoting constituents from Chaenomeles sinensis KOEHNE and their activities in JB6 mouse epidermal cells. | 2003-11 |
|
| High isoflavone content and estrogenic activity of 25 year-old Glycine max tissue cultures. | 2003-10 |
|
| Ultrasound-assisted extraction of soy isoflavones. | 2003-09-19 |
|
| Block by phytoestrogens of recombinant human neuronal nicotinic receptors. | 2003-09 |
|
| Metabolism of the soybean isoflavone glycoside genistin in vitro by human gut bacteria and the effect of prebiotics. | 2003-09 |
|
| Mass spectrometric methods for the analysis of chlorinated and nitrated isoflavonoids: a novel class of biological metabolites. | 2003-07 |
|
| The effect of oestrogen and dietary phyto-oestrogens on transepithelial calcium transport in human intestinal-like Caco-2 cells. | 2003-06 |
|
| Upregulation of isoflavonoids and soluble proteins in edible legumes by light and fungal elicitor treatments. | 2003-06 |
|
| Flavone C-glycosides from Lupinus hartwegii. | 2003-06 |
|
| Flavonoid increase in soybean as a response to Nezara viridula injury and its effect on insect-feeding preference. | 2003-05 |
|
| Stability of isoflavones in soy milk stored at elevated and ambient temperatures. | 2003-04-09 |
|
| Pharmacological activities of stromata of Cordyceps scarabaecola. | 2003-03 |
Patents
Sample Use Guides
Ovx rats were treated with genistin-rich isoflavones (5 mkg/kg of body weight) for 50 days.
Route of Administration:
Oral
SK-OV-3 cells were used for activity evaluation. Cells were routinely maintained in RPMI 1640 (Gibco), supplemented with 10%FBS and antibiotics (50 U/ml of penicillin and 50 μg/ml streptomycin,Gibco) at 37 °C in a humidified atmosphere containing 5% CO2. In cell proliferation and cell cycle analysis experiments, cells were treatedwith either genistein or genistin alone, or vehicle alone for 24 h and 48 h. Cell proliferation was determined using the MTT assay.
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529-59-9
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DTXSID3022324
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27514
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m5696
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5281377
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1POG3SCN5T
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C040641
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1288805
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GENISTIN
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SUBSTANCE RECORD
