genistin
4',5,7-trihydroxyisoflavone 7-D-glucoside
 
Notes:
glycoside of soy bean isoflavone, gentistein. Present in soy foods. Potential nutriceutical. Isol. from Prunus avium (wild cherry) Genistin is one of several known isoflavones. Genistin is found in a number of plants and herbs like soy.
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5-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one (Click)
CAS Number: 529-59-9Picture of molecule
FDA UNII: 1POG3SCN5T
Nikkaji Web: J40.719D
Beilstein Number: 0064479
MDL: MFCD00016883
XlogP3-AA: 0.90 (est)
Molecular Weight: 432.38240000
Formula: C21 H20 O10
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidants
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 788.90 °C. @ 760.00 mm Hg (est)
Flash Point: 537.00 °F. TCC ( 280.70 °C. ) (est)
logP (o/w): 0.790 (est)
Soluble in:
 water, 1417 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
skin conditioning
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Suppliers:
Coompo
For experimental / research use only.
Genistin from Plants ≥98.5%
Odor: characteristic
Use: An isoflavone glycoside found in soy-based food products. This is an inactive analog of the PTK inhibitor Genistein and can be used as a negative control for Genistein. Genistin, like genistein, is a phytoestrogen as it was shown to stimulate estrogen- dependent breast cancer cell growth in vivo. Genistin and other isoflavones are demonstrated to be bioactive within the neonatal intestine and may reduce the severity of rotavirus infections; genistin alone shows inhibition of the viral infectivity by 40-60%. In vitro study have shown that both genistin and genistein are capable of enhancing bone metabolism in the femoral-metaphyseal tissues of elderly rats. Reported to reduce bone loss in ovarectomized rats.
EMD Millipore
For experimental / research use only.
Genistin
ExtraSynthese
For experimental / research use only.
Genistin (HPLC) ≥99%
Nacalai USA
For experimental / research use only.
Genistin
Santa Cruz Biotechnology
For experimental / research use only.
Genistin ≥99%
Sigma-Aldrich
For experimental / research use only.
Genistin
analytical standard
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50  > 2000 mg/kg
Pharmaceutical Chemistry Journal Vol. 13, Pg. 51, 1979.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antioxidants
Recommendation for genistin usage levels up to:
 not for fragrance use.
 
Recommendation for genistin flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Preparatory work to support the risk assessment for peri- and postmenopausal women taking food supplements containing isolated isoflavones
View page or View pdf
Risk assessment for peri- and post-menopausal women taking food supplements containing isolated isoflavones
View page or View pdf
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5281377
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 5-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Chemidplus: 0000529599
RTECS: DJ3093000 for cas# 529-59-9
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References:
 5-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5281377
Pubchem (sid): 135050235
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C09126
HMDB (The Human Metabolome Database): HMDB33988
FooDB: FDB012221
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cherry sour cherry fruit
Search Trop  Picture
 cherry sweet cherry
Search Trop  Picture
 lupine white lupine
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 soybean cotyledon
Search Trop  Picture
 soybean hypocotyl
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 soybean seed
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 soybean seed coat
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 soybean shoot
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 soybean testa
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Synonyms:
4H-1-benzopyran-4-one, 7- (β-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-
4H-1-benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-
isoflavone, 4',5,7-trihydroxy-, 7-D-glucoside
 genistein 7-glucoside
 genistein 7-O-b-D-glucoside
 genistein glucoside
 genisteol 7-monoglucoside
 genistin (8CI)
 genistoside
7-(b-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
5-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-one
5-hydroxy-3-(4-hydroxyphényl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}-4H-chromén-4-one
4',5,7-trihydroxyisoflavone 7-D-glucoside
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Articles:
PubMed: Isoflavones of the Soybean Components and the Effect of Germination Time in the Cotyledons and Embryonic Axis.
PubMed: Genistein isoflavone glycoconjugates in sour cherry (Prunus cerasus L.) cultivars.
PubMed: Profile of the contents of different forms of soybean isoflavones and the effect of germination time on these compounds and the physical parameters in soybean sprouts.
PubMed: Glycation is regulated by isoflavones.
PubMed: β-Glucosidase activity and bioconversion of isoflavones during fermentation of soymilk.
PubMed: Identification and quantification of the main isoflavones and other phytochemicals in soy based nutraceutical products by liquid chromatography-orbitrap high resolution mass spectrometry.
PubMed: Malonylglucoside conjugates of isoflavones are much less bioavailable compared with unconjugated β-glucosidic forms in rats.
PubMed: Isoflavones profiling of soybean [Glycine max (L.) Merrill] germplasms and their correlations with metabolic pathways.
PubMed: Isoflavone intake inhibits the development of 7,12-dimethylbenz(a)anthracene(DMBA)-induced mammary tumors in normal and ovariectomized rats.
PubMed: Chemical compounds related to nutraceutical and industrial qualities of non-transgenic soybean genotypes.
PubMed: Inhibitory effects of a major soy isoflavone, genistein, on human DNA topoisomerase II activity and cancer cell proliferation.
PubMed: Rapid magnetic solid-phase extraction for the selective determination of isoflavones in soymilk using baicalin-functionalized magnetic nanoparticles.
PubMed: Enrichment of two isoflavone aglycones in black soymilk by using spent coffee grounds as an immobiliser for β-glucosidase.
PubMed: Determination of the variations in levels of phenolic compounds in soybean (Glycine max Merr.) sprouts infected by anthracnose (Colletotrichum gloeosporioides).
PubMed: A comparative analysis of the photo-protective effects of soy isoflavones in their aglycone and glucoside forms.
PubMed: Enrichment of two isoflavone aglycones in black soymilk by immobilized β-glucosidase on solid carriers.
PubMed: A modified QuEChERS method as sample treatment before the determination of isoflavones in foods by ultra-performance liquid chromatography-triple quadrupole mass spectrometry.
PubMed: Genistein and dicarboximide fungicides in infant formulae from the EU market.
PubMed: Antioxidant and Antityrosinase Activity of Flemingia macrophylla and Glycine tomentella Roots.
PubMed: Fast simultaneous determination of free and conjugated isoflavones in soy milk by UHPLC-UV.
PubMed: Apoptotic effects of cooked and in vitro digested soy on human prostate cancer cells.
PubMed: Distribution of isoflavones and coumestrol in neglected tropical and subtropical legumes.
PubMed: Comparative evaluation of the teratogenicity of genistein and genistin using rat whole embryo culture and limbud micromass culture methods.
PubMed: Bactericidal activity of soymilk fermentation broth by in vitro and animal models.
PubMed: Flavonoids, a ubiquitous dietary phenolic subclass, exert extensive in vitro anti-invasive and in vivo anti-metastatic activities.
PubMed: Absorption and plasma disposition of genistin differ from those of genistein in healthy women.
PubMed: Hydrolysis of isoflavone glycosides by a thermostable β-glucosidase from Pyrococcus furiosus.
PubMed: Effect of Lactobacillus sporogenes on oral isoflavones bioavailability: single dose pharmacokinetic study in menopausal women.
PubMed: Modification of isoflavone profiles in a fermented soy food with almond powder.
PubMed: NTP-CERHR expert panel report on the developmental toxicity of soy infant formula.
PubMed: Soy isoflavones and other isoflavonoids activate the human bitter taste receptors hTAS2R14 and hTAS2R39.
PubMed: Characterization of a GH3 family β-glucosidase from Dictyoglomus turgidum and its application to the hydrolysis of isoflavone glycosides in spent coffee grounds.
PubMed: Phenolic tyrosinase inhibitors from the stems of Cudrania cochinchinensis.
PubMed: Enhanced growth of lactobacilli and bioconversion of isoflavones in biotin-supplemented soymilk upon ultrasound-treatment.
PubMed: Bioassay based screening of steroid derivatives in animal feed and supplements.
PubMed: Comparison of three thermostable β-glucosidases for application in the hydrolysis of soybean isoflavone glycosides.
PubMed: Optimizing time and temperature of enzymatic conversion of isoflavone glucosides to aglycones in soy germ flour.
PubMed: Yeast α-glucosidase inhibition by isoflavones from plants of Leguminosae as an in vitro alternative to acarbose.
PubMed: Influence of natural coagulants on isoflavones and antioxidant activity of tofu.
PubMed: Evaluation of quality of Radix Puerariae herbal medicine by isoflavonoids.
PubMed: Formation of succinyl genistin and succinyl daidzin by Bacillus species.
PubMed: Differential effects of whole soy extract and soy isoflavones on apoptosis in prostate cancer cells.
PubMed: Characterization of fermented black soybean natto inoculated with Bacillus natto during fermentation.
PubMed: Comprehensive profiling of isoflavones, phytosterols, tocopherols, minerals, crude protein, lipid, and sugar during soybean (Glycine max) germination.
PubMed: Semipurified fractions from the submerged-culture broth of Agaricus blazei Murill reduce blood glucose levels in streptozotocin-induced diabetic rats.
PubMed: 1H NMR fingerprinting of soybean extracts, with emphasis on identification and quantification of isoflavones.
PubMed: Combination of genistin and fructooligosaccharides prevents bone loss in ovarian hormone deficiency.
PubMed: Comparison of Puerariae Radix and its hydrolysate on stimulation of hyaluronic acid production in NHEK cells.
PubMed: Angiotensin I-converting enzyme inhibitory activity and bioconversion of isoflavones by probiotics in soymilk supplemented with prebiotics.
PubMed: Soy formula and isoflavones and the developing intestine.
PubMed: Chromatographic quantification of isoflavone content from soy derivates using HPLC technique.
PubMed: Glycosylation of dietary flavonoids decreases the affinities for plasma protein.
PubMed: Hypolipidemic effects of Monascus-fermented soybean extracts in rats fed a high-fat and -cholesterol diet.
PubMed: Effect of glycosidation of isoflavones on their bioavailability and pharmacokinetics in aged male rats.
PubMed: Comparison of hormonal activity of isoflavone-containing supplements used to treat menopausal complaints.
PubMed: Nanonized black soybean enhances immune response in senescence-accelerated mice.
PubMed: Stability of isoflavone isomers in steamed black soybeans and black soybean koji stored under different conditions.
PubMed: Enhanced in vitro and in vivo antioxidant activity and mobilization of free phenolic compounds of soybean flour fermented with different beta-glucosidase-producing fungi.
PubMed: Comparative metabolic profiling reveals secondary metabolites correlated with soybean salt tolerance.
PubMed: Phytoestrogens and breast cancer: a complex story.
PubMed: Effects of riboflavin photosensitization on the changes of isoflavones in soymilk.
PubMed: Characterization of phenolic substances and antioxidant properties of food soybeans grown in the North Dakota-Minnesota region.
PubMed: Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr. et Maxim.
PubMed: Biomolecules and nutritional quality of soymilk fermented with probiotic yeast and bacteria.
PubMed: The combination of genistin and ipriflavone prevents mammary tumorigenesis and modulates lipid profile.
PubMed: Skim milk powder supplementation affects lactose utilization, microbial survival and biotransformation of isoflavone glycosides to isoflavone aglycones in soymilk by Lactobacillus.
PubMed: Accumulation of isoflavone genistin in transgenic tomato plants overexpressing a soybean isoflavone synthase gene.
PubMed: Hydrolysis of isoflavone glucosides in soymilk fermented with single or mixed cultures of Lactobacillus paraplantarum KM, Weissella sp. 33, and Enterococcus faecium 35 isolated from humans.
PubMed: Effect of lactulose on biotransformation of isoflavone glycosides to aglycones in soymilk by lactobacilli.
PubMed: Puma is a novel target of soy isoflavone genistein but is dispensable for genistein-induced cell fate determination.
PubMed: WITHDRAWN: The combination of genistin and ipriflavone prevents mammary tumorigenesis and modulates lipid profile.
PubMed: Characterization of a thermostable extracellular beta-glucosidase with activities of exoglucanase and transglycosylation from Paecilomyces thermophila.
PubMed: Cloning, expression, and characterization of two beta-glucosidases from isoflavone glycoside-hydrolyzing Bacillus subtilis natto.
PubMed: Conversion of isoflavone glucosides to aglycones in soymilk by fermentation with lactic acid bacteria.
PubMed: Comparison of isoflavone concentrations in soybean (Glycine max (L.) Merrill) sprouts grown under two different light conditions.
PubMed: Isoflavones at concentrations present in soy infant formula inhibit rotavirus infection in vitro.
PubMed: Solvent effects on extraction and HPLC analysis of soybean isoflavones and variations of isoflavone compositions as affected by crop season.
PubMed: Dietary phytoestrogens and photoperiodic response in a male songbird, the Dark-eyed Junco (Junco hyemalis).
PubMed: Anti-obesity activities of fermented soygerm isoflavones by Bifidobacterium breve.
PubMed: Disruption of the developing female reproductive system by phytoestrogens: genistein as an example.
PubMed: Bioavailability of soy isoflavones in rats Part I: application of accurate methodology for studying the effects of gender and source of isoflavones.
PubMed: Review of the factors affecting bioavailability of soy isoflavones in humans.
PubMed: Phytoestrogens levels determination in the cord blood from Malaysia rural and urban populations.
PubMed: Biotransformation of common bean (Phaseolus vulgaris L.) flavonoid glycosides by bifidobacterium species from human intestinal origin.
PubMed: Enhanced estrogenic responses and sensitivity to azoxymethane following dietary soy isoflavone supplementation in older female rats.
PubMed: Bioavailability of genistein and its glycoside genistin as measured in the portal vein of freely moving unanesthetized rats.
PubMed: Heat and pH effects on the conjugated forms of genistin and daidzin isoflavones.
PubMed: An accurate and reproducible method for the quantitative analysis of isoflavones and their metabolites in rat plasma using liquid chromatography/mass spectrometry combined with photodiode array detection.
PubMed: Influence of the application of three different elicitors on soybean plants on the concentrations of several isoflavones in soybean seeds.
PubMed: Water-soluble genistin glycoside isoflavones up-regulate antioxidant metallothionein expression and scavenge free radicals.
PubMed: Isoflavonoids are present in Arabidopsis thaliana despite the absence of any homologue to known isoflavonoid synthases.
PubMed: Distribution profiles of isoflavone isomers in black bean kojis prepared with various filamentous fungi.
PubMed: Isoflavone levels in five soybean (Glycine max) genotypes are altered by phytochrome-mediated light treatments.
PubMed: Soy processing affects metabolism and disposition of dietary isoflavones in ovariectomized BALB/c mice.
PubMed: Are chemical compounds important for soybean resistance to Anticarsia gemmatalis?
PubMed: Supercritical fluid extraction of isoflavones from biological samples with ultra-fast high-performance liquid chromatography/mass spectrometry.
PubMed: Glycosylation of genistin into soluble inclusion complex form of cyclic glucans by enzymatic modification.
PubMed: 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.
PubMed: Pharmacokinetics of a slow-release formulation of soybean isoflavones in healthy postmenopausal women.
PubMed: 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.
PubMed: Anticancer therapeutic potential of soy isoflavone, genistein.
PubMed: Phloridzin improves absorption of genistin in isolated rat small intestine.
PubMed: Kudzu root extract suppresses voluntary alcohol intake and alcohol withdrawal symptoms in P rats receiving free access to water and alcohol.
PubMed: 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.
PubMed: Enhancement of tofu isoflavone recovery by pretreatment of soy milk with koji enzyme extract.
PubMed: Genistein at a concentration present in soy infant formula inhibits Caco-2BBe cell proliferation by causing G2/M cell cycle arrest.
PubMed: Intestinal uptake of genistein and its glycoside in the rat using various isolated perfused gut segments.
PubMed: Soy processing influences growth of estrogen-dependent breast cancer tumors.
PubMed: Effects of dose and glycosylation on the transfer of genistein into the eggs of the Japanese quail (Coturnix japonica).
PubMed: Effect of water-to-bean ratio on the contents and compositions of isoflavones in tofu.
PubMed: Purification and characterization of an isoflavone-conjugates-hydrolyzing beta-glucosidase from endophytic bacterium.
PubMed: Simultaneous determination of isoflavones and bisphenol A in rat serum by high-performance liquid chromatography coupled with coulometric array detection.
PubMed: Fermented grain products, production, properties and benefits to health.
PubMed: Metabolism of the soybean isoflavone glycoside genistin in vitro by human gut bacteria and the effect of prebiotics.
PubMed: The effect of oestrogen and dietary phyto-oestrogens on transepithelial calcium transport in human intestinal-like Caco-2 cells.
PubMed: Stability of isoflavones in soy milk stored at elevated and ambient temperatures.
PubMed: Evaluation of the estrogenic effects of legume extracts containing phytoestrogens.
PubMed: [Comparison of soyasaponin and isoflavone contents between genetically modified (GM) and non-GM soybeans].
PubMed: Antimutagenic effects of doenjang (Korean fermented soypaste) and its active compounds.
PubMed: Determination of isoflavones in ready-to-feed soy-based infant formula.
PubMed: Determination of daidzein and genistein in soybean foods by automated on-line in-tube solid-phase microextraction coupled to high-performance liquid chromatography.
PubMed: In vitro antioxidant activity of some selected Prunus species in Korea.
PubMed: Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds of glyphosate-treated, glyphosate-resistant soybean.
PubMed: Composition, red blood cell uptake, and serum protein binding of phytoestrogens extracted from commercial kudzu-root and soy preparations.
PubMed: Stabilities of daidzin, glycitin, genistin, and generation of derivatives during heating.
PubMed: Inhibitory effects of isoflavones on nitric oxide- or peroxynitrite-mediated DNA damage in RAW 264.7 cells and phiX174 DNA.
PubMed: Daidzein and genistein content of cereals.
PubMed: Phytoestrogen-low diet for endocrine disruptor studies.
PubMed: Isoflavone aglycon and glucoconjugate content of high- and low-soy U.K. foods used in nutritional studies.
PubMed: Inhibitory effect of isoflavones on peroxynitrite-mediated low-density lipoprotein oxidation.
PubMed: Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism.
PubMed: Determination of isoflavones in soy and selected foods containing soy by extraction, saponification, and liquid chromatography: collaborative study.
PubMed: Dietary genistin stimulates growth of estrogen-dependent breast cancer tumors similar to that observed with genistein.
PubMed: Isoflavone transformation during soybean koji preparation and subsequent miso fermentation supplemented with ethanol and NaCl.
PubMed: Preparative separation of isoflavone components in soybeans using high-speed counter-current chromatography.
PubMed: Changes in the profile of genistein, daidzein, and their conjugates during thermal processing of tofu.
PubMed: MALDI-TOF MS analysis of isoflavones in soy products.
PubMed: Factors affecting flavonoids absorption.
PubMed: Daidzein and genistein contents of vegetables.
PubMed: Retention and changes of soy isoflavones and carotenoids in immature soybean seeds (Edamame) during processing.
PubMed: Daidzein and genistein content of fruits and nuts.
PubMed: Determination of the levels of isoflavonoids in soybeans and soy-derived foods and estimation of isoflavonoids in the Japanese daily intake.
PubMed: Soybean meal fermented by Aspergillus awamori increases the cytochrome P-450 content of the liver microsomes of mice.
PubMed: LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense).
PubMed: Antioxidant polyphenols from tart cherries (Prunus cerasus).
PubMed: Antioxidant action and potential antidiabetic properties of an isoflavonoid-containing soyabean phytochemical extract (SPE).
PubMed: Antimutagenic activity of chemical fractions isolated from a commercial soybean processing by-product.
PubMed: Daidzein and genistein but not their glucosides are absorbed from the rat stomach.
PubMed: Isoflavone-mediated inhibition of tyrosine kinase: a novel antiinflammatory approach.
PubMed: Soy isoflavone analysis: quality control and a new internal standard.
PubMed: Extraction and quantification of daidzein and genistein in food.
PubMed: In vivo antioxidant activity of Okara Koji, a fermented okara, by Aspergillus oryzae.
PubMed: Quantification of genistein and genistin in soybeans and soybean products.
PubMed: Induction of micronucleus formation in mouse splenocytes by the soy isoflavone genistein in vitro but not in vivo.
PubMed: Oestrogenic potency of genistin and daidzin in mice.
PubMed: Oestrogenic response of the CD-1 mouse to the soya-bean isoflavones genistein, genistin and daidzin.
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