491-80-5,MFCD00006839
Catalog No.:AA00I8R7

491-80-5 | 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

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1g
98%
in stock  
$39.00   $27.00
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5g
98%
in stock  
$99.00   $69.00
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10g
98%
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$154.00   $108.00
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25g
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100g
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Technical Information
Catalog Number:
AA00I8R7
Chemical Name:
5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
CAS Number:
491-80-5
Molecular Formula:
C16H12O5
Molecular Weight:
284.2635
MDL Number:
MFCD00006839
SMILES:
COc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
NSC Number:
123538
Properties
Computed Properties
 
Complexity:
424  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
2  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
3  

Literature

Title: Red Clover Aryl Hydrocarbon Receptor (AhR) and Estrogen Receptor (ER) Agonists Enhance Genotoxic Estrogen Metabolism.

Journal: Chemical research in toxicology 20171120

Title: Comparative Developmental Toxicity of Flavonoids Using an Integrative Zebrafish System.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20161101

Title: In vivo prediction of CYP-mediated metabolic interaction potential of formononetin and biochanin A using in vitro human and rat CYP450 inhibition data.

Journal: Toxicology letters 20151119

Title: Isoflavones enhance interleukin-17 gene expression via retinoic acid receptor-related orphan receptors α and γ.

Journal: Toxicology 20150302

Title: Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor.

Journal: Scientific reports 20140101

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Phytotoxic effect, uptake, and transformation of biochanin A in selected weed species.

Journal: Journal of agricultural and food chemistry 20121031

Title: Germination dramatically increases isoflavonoid content and diversity in chickpea (Cicer arietinum L.) seeds.

Journal: Journal of agricultural and food chemistry 20120905

Title: Red clover extract ameliorates dyslipidemia in streptozotocin-induced diabetic C57BL/6 mice by activating hepatic PPARα.

Journal: Phytotherapy research : PTR 20120601

Title: Effects of sodium selenite and germination on the sprouting of chickpeas (Cicer arietinum L.) and its content of selenium, formononetin and biochanin A in the sprouts.

Journal: Biological trace element research 20120601

Title: Double-edged sword effect of biochanin to inhibit nuclear factor kappaB: suppression of serine/threonine and tyrosine kinases.

Journal: Biochemical pharmacology 20120515

Title: Biotransformation of sophoricoside in Fructus sophorae by the fungus Schizophyllum commune.

Journal: Bioresource technology 20120501

Title: Ester and carbamate ester derivatives of Biochanin A: synthesis and in vitro evaluation of estrogenic and antiproliferative activities.

Journal: Bioorganic & medicinal chemistry 20120501

Title: Development of a new class of aromatase inhibitors: design, synthesis and inhibitory activity of 3-phenylchroman-4-one (isoflavanone) derivatives.

Journal: Bioorganic & medicinal chemistry 20120415

Title: Effects of phytoestrogens derived from soy bean on expression of adhesion molecules on HUVEC.

Journal: Climacteric : the journal of the International Menopause Society 20120401

Title: Identification of Genistein and Biochanin A by THz (far-infrared) vibrational spectra.

Journal: Journal of pharmaceutical and biomedical analysis 20120325

Title: Effects of sodium metavanadate and germination on the sprouting of chickpeas and its content of vanadium, formononetin and biochanin A in the sprouts.

Journal: Journal of dietary supplements 20120301

Title: Antihyperglycemic effect of biochanin A, a soy isoflavone, on streptozotocin-diabetic rats.

Journal: European journal of pharmacology 20120215

Title: Reduced bioavailability of tamoxifen and its metabolite 4-hydroxytamoxifen after oral administration with biochanin A (an isoflavone) in rats.

Journal: Phytotherapy research : PTR 20120201

Title: Constituents of Dalbergia sissoo Roxb. leaves with osteogenic activity.

Journal: Bioorganic & medicinal chemistry letters 20120115

Title: Biochanin A ameliorates the cytokine secretion profile of lipopolysaccharide-stimulated macrophages by a PPARγ-dependent pathway.

Journal: Molecular medicine reports 20120101

Title: Red clover and soy isoflavones--an in vitro safety assessment.

Journal: Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20111201

Title: The sulfated conjugate of biochanin A is a substrate of breast cancer resistant protein (ABCG2).

Journal: Biopharmaceutics & drug disposition 20111101

Title: Apoptotic effects of genistein, biochanin-A and apigenin on LNCaP and PC-3 cells by p21 through transcriptional inhibition of polo-like kinase-1.

Journal: Journal of Korean medical science 20111101

Title: The cannabinoid receptor inverse agonist AM251 regulates the expression of the EGF receptor and its ligands via destabilization of oestrogen-related receptor α protein.

Journal: British journal of pharmacology 20111001

Title: Liquid chromatography-mass spectrometry method for the quantification of tamoxifen and its metabolite 4-hydroxytamoxifen in rat plasma: application to interaction study with biochanin A (an isoflavone).

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20111001

Title: Modulatory effects of curcumin on multi-drug resistance-associated protein 5 in pancreatic cancer cells.

Journal: Cancer chemotherapy and pharmacology 20110901

Title: Improved effectiveness of biochanin A as a P-gp inhibitor in solid dispersion.

Journal: Die Pharmazie 20110901

Title: [Establishment and application of co-transfection screening method for phytoestrogen active constituents].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110901

Title: Enhanced dissolution and bioavailability of biochanin A via the preparation of solid dispersion: in vitro and in vivo evaluation.

Journal: International journal of pharmaceutics 20110830

Title: Synergistic chemoprotective mechanisms of dietary phytoestrogens in a select combination against prostate cancer.

Journal: The Journal of nutritional biochemistry 20110801

Title: LC-ESI-MS characterisation of phytoalexins induced in chickpea and pea tissues in response to a biotic elicitor of Hypnea musciformis (red algae).

Journal: Natural product research 20110801

Title: Structural requirements of flavonoids for the adipogenesis of 3T3-L1 cells.

Journal: Bioorganic & medicinal chemistry 20110501

Title: Biochanin-A, an isoflavon, showed anti-proliferative and anti-inflammatory activities through the inhibition of iNOS expression, p38-MAPK and ATF-2 phosphorylation and blocking NFκB nuclear translocation.

Journal: European journal of pharmacology 20110225

Title: Quantification of five isoflavones and coumestrol in various solid agroenvironmental matrices using ¹³c₃-labeled internal standards.

Journal: Journal of agricultural and food chemistry 20110209

Title: The effects of native and synthetic estrogenic compounds as well as vitamin D less-calcemic analogs on adipocytes content in rat bone marrow.

Journal: Journal of endocrinological investigation 20110201

Title: The effects of estrogen receptors α- and β-specific agonists and antagonists on cell proliferation and energy metabolism in human bone cell line.

Journal: Journal of cellular biochemistry 20110201

Title: In vitro and in vivo melanogenesis inhibition by biochanin A from Trifolium pratense.

Journal: Bioscience, biotechnology, and biochemistry 20110101

Title: High-throughput quantification of isoflavones, biochanin A and genistein, and their conjugates in female rat plasma using LC-ESI-MS/MS: Application in pharmacokinetic study.

Journal: Journal of separation science 20101101

Title: The characterisation of structural and antioxidant properties of isoflavone metal chelates.

Journal: Journal of inorganic biochemistry 20101001

Title: Biochanin A reduces drug-induced p75NTR expression and enhances cell survival: a new in vitro assay for screening inhibitors of p75NTR expression.

Journal: Rejuvenation research 20101001

Title: Phenolic compounds from Pueraria lobata protect PC12 cells against Aβ-induced toxicity.

Journal: Archives of pharmacal research 20101001

Title: Antimicrobial effect of red clover (Trifolium pratense) phenolic extract on the ruminal hyper ammonia-producing bacterium, Clostridium sticklandii.

Journal: Current microbiology 20100801

Title: An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.

Journal: Journal of natural products 20100723

Title: LC-MSMS profiling of flavonoid conjugates in wild Mexican lupine, Lupinus reflexus.

Journal: Journal of natural products 20100723

Title: Effect of combination treatment of rapamycin and isoflavones on mTOR pathway in human glioblastoma (U87) cells.

Journal: Neurochemical research 20100701

Title: New flavonoids with 2BS cell proliferation promoting effect from the seeds of Trigonella foenum-graecum L.

Journal: Journal of natural medicines 20100701

Title: Effects of the isoflavonoid biochanin A on the transport of mitoxantrone in vitro and in vivo.

Journal: Biopharmaceutics & drug disposition 20100701

Title: Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase.

Journal: British journal of pharmacology 20100601

Title: Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19).

Journal: Bioorganic & medicinal chemistry letters 20100515

Title: Syntheses, characterization and antitumor activities of transition metal complexes with isoflavone.

Journal: Journal of inorganic biochemistry 20100401

Title: Selective growth inhibitory effect of biochanin A against intestinal tract colonizing bacteria.

Journal: Molecules (Basel, Switzerland) 20100303

Title: Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications.

Journal: Toxicology letters 20100215

Title: Interactions between the flavonoid biochanin A and P-glycoprotein substrates in rats: in vitro and in vivo.

Journal: Journal of pharmaceutical sciences 20100101

Title: Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.

Journal: Bioorganic & medicinal chemistry 20100101

Title: Biochanin A induction of sulfotransferases in rats.

Journal: Journal of biochemical and molecular toxicology 20100101

Title: Novel screening method for potential skin-whitening compounds by a luciferase reporter assay.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: Spatial distribution and quantification of endocrine-disrupting chemicals in Sado River estuary, Portugal.

Journal: Environmental monitoring and assessment 20091201

Title: Inhibition of angiogenesis and inflammation by an extract of red clover (Trifolium pratense L.).

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20091201

Title: Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells.

Journal: Journal of natural products 20091201

Title: Quantification of phytoestrogens in industrial waste streams.

Journal: Environmental toxicology and chemistry 20091101

Title: Cellular DNA breakage by soy isoflavone genistein and its methylated structural analogue biochanin A.

Journal: Molecular nutrition & food research 20091101

Title: Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay.

Journal: Bioorganic & medicinal chemistry letters 20090815

Title: Modulatory influence of prepubertal biochanin A exposure on mammary gland differentiation and expression of estrogen receptor-alpha and apoptotic proteins.

Journal: Phytotherapy research : PTR 20090701

Title: Pressurized liquid extraction versus other extraction techniques in micropreparative isolation of pharmacologically active isoflavones from Trifolium L. species.

Journal: Talanta 20090630

Title: Single amino acid mutations of Medicago glycosyltransferase UGT85H2 enhance activity and impart reversibility.

Journal: FEBS letters 20090618

Title: AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.

Journal: Chemico-biological interactions 20090316

Title: Determination and pharmacokinetic study of taxifolin in rabbit plasma by high-performance liquid chromatography.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20090301

Title: The isoflavones mixture from Trifolium pratense L. protects HCN 1-A neurons from oxidative stress.

Journal: Phytotherapy research : PTR 20090201

Title: Effect of frequency and duration of ultrasonication on the extraction efficiency of selected isoflavones and trans-resveratrol from peanuts (Arachis hypogaea).

Journal: Ultrasonics sonochemistry 20090201

Title: Discovery of a potent and selective inhibitor for human carbonyl reductase 1 from propionate scanning applied to the macrolide zearalenone.

Journal: Bioorganic & medicinal chemistry 20090115

Title: Antiparasitic activity of biochanin A, an isolated isoflavone from fruits of Cassia fistula (Leguminosae).

Journal: Parasitology research 20090101

Title: Effects of dietary phytoestrogens on plasma testosterone and triiodothyronine (T3) levels in male goat kids.

Journal: Acta veterinaria Scandinavica 20090101

Title: Establishment of a transgenic yeast screening system for estrogenicity and identification of the anti-estrogenic activity of malachite green.

Journal: Journal of cellular biochemistry 20081215

Title: Biochanin A inhibits breast cancer tumor growth in a murine xenograft model.

Journal: Pharmaceutical research 20080901

Title: Plant phenolic compounds as ethidium bromide efflux inhibitors in Mycobacterium smegmatis.

Journal: The Journal of antimicrobial chemotherapy 20080801

Title: Effect of mycorrhization on the isoflavone content and the phytoestrogen activity of red clover.

Journal: Journal of plant physiology 20080731

Title: Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.

Journal: Journal of medicinal chemistry 20080724

Title: Ultrahigh-pressure liquid chromatography of isoflavones and phenolic acids on different stationary phases.

Journal: Journal of chromatography. A 20080627

Title: Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).

Journal: Journal of medicinal chemistry 20080612

Title: Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.

Journal: Bioorganic & medicinal chemistry 20080515

Title: Chemoprevention of mammary tumorigenesis and chemomodulation of the antioxidative enzymes and peroxidative damage in prepubertal Sprague Dawley rats by Biochanin A.

Journal: Molecular and cellular biochemistry 20080501

Title: Daidzein but not other phytoestrogens preserves bone architecture in ovariectomized female rats in vivo.

Journal: Journal of cellular biochemistry 20080415

Title: Topical isoflavones provide effective photoprotection to skin.

Journal: Photodermatology, photoimmunology & photomedicine 20080401

Title: Variable isoflavone content of red clover products affects intestinal disposition of biochanin A, formononetin, genistein, and daidzein.

Journal: Journal of alternative and complementary medicine (New York, N.Y.) 20080401

Title: The red clover (Trifolium pratense) isoflavone biochanin A inhibits aromatase activity and expression.

Journal: The British journal of nutrition 20080201

Title: Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition.

Journal: Bioorganic & medicinal chemistry 20080101

Title: Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor.

Journal: The Journal of steroid biochemistry and molecular biology 20080101

Title: NMR spectral assignments of a new [C--O--C] isoflavone dimer from Andira surinamensis.

Journal: Magnetic resonance in chemistry : MRC 20080101

Title: Isoflavonoid glycosides and rotenoids from Pongamia pinnata leaves.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20080101

Title: Oestrogen receptor alpha is required for biochanin A-induced apolipoprotein A-1 mRNA expression in HepG2 cells.

Journal: The British journal of nutrition 20070901

Title: Optimization of a rapid microwave assisted extraction method for the liquid chromatography-electrospray-tandem mass spectrometry determination of isoflavonoid aglycones in soybeans.

Journal: Journal of chromatography. A 20070608

Title: Yeast-based screening to identify modulators of G-protein signaling using uncontrolled cell division cycle by overexpression of Stm1.

Journal: Journal of biotechnology 20070501

Title: Biochanin A protects dopaminergic neurons against lipopolysaccharide-induced damage through inhibition of microglia activation and proinflammatory factors generation.

Journal: Neuroscience letters 20070501

Title: Effects of the flavonoid biochanin A on gene expression in primary human hepatocytes and human intestinal cells.

Journal: Molecular nutrition & food research 20070301

Title: Evaluation of matrix effects in metabolite profiling based on capillary liquid chromatography electrospray ionization quadrupole time-of-flight mass spectrometry.

Journal: Analytical chemistry 20070215

Title: Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20070201

Title: [Chemical constituents of isoflavones from vine stems of Millettia nitita var. hirsutissima].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20070201

Title: Nicotine and biochanin A, but not cigarette smoke, induce anti-inflammatory effects on keratinocytes and endothelial cells in patients with Behçet's disease.

Journal: The Journal of investigative dermatology 20070101

Title: Effects of flavonoids genistein and biochanin a on gene expression and their metabolism in human mammary cells.

Journal: Nutrition and cancer 20070101

Title: 25 hydroxy-vitamin D(3)-1alpha hydroxylase expression and activity in cultured human osteoblasts and their modulation by parathyroid hormone, estrogenic compounds and dihydrotestosterone.

Journal: The Journal of steroid biochemistry and molecular biology 20070101

Title: Pharmacokinetics and bioavailability of the bioflavonoid biochanin A: effects of quercetin and EGCG on biochanin A disposition in rats.

Journal: Molecular pharmaceutics 20070101

Title: Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.

Journal: Journal of molecular graphics & modelling 20061101

Title: Phytoestrogens and their low dose combinations inhibit mRNA expression and activity of aromatase in human granulosa-luteal cells.

Journal: The Journal of steroid biochemistry and molecular biology 20061101

Title: Inhibition of matrix degrading enzymes and invasion in human glioblastoma (U87MG) cells by isoflavones.

Journal: Journal of neuro-oncology 20060901

Title: Altered oral bioavailability and pharmacokinetics of P-glycoprotein substrates by coadministration of biochanin A.

Journal: Journal of pharmaceutical sciences 20060901

Title: Mechanisms underlying biochanin A-induced relaxation of the aorta differ between normotensive and hypertensive rats.

Journal: Clinical and experimental pharmacology & physiology 20060901

Title: Pharmacokinetics and bioavailability of the isoflavone biochanin A in rats.

Journal: The AAPS journal 20060901

Title: Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages.

Journal: Journal of agricultural and food chemistry 20060809

Title: [Endothelium-independent vasorelaxation of plant-derived estrogen biochanin A and its mechanism in rat aortic rings].

Journal: Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology 20060801

Title: A comparative study on the protective effects of 17beta-estradiol, biochanin A and bisphenol A on mammary gland differentiation and tumorigenesis in rats.

Journal: Indian journal of experimental biology 20060701

Title: Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells.

Journal: Archives of pharmacal research 20060701

Title: Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.

Journal: Journal of medicinal chemistry 20060601

Title: Up-regulation of interleukin-4 production via NF-AT/AP-1 activation in T cells by biochanin A, a phytoestrogen and its metabolites.

Journal: Toxicology and applied pharmacology 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Responsiveness to estradiol-17beta and to phytoestrogens in primary human osteoblasts is modulated differentially by high glucose concentration.

Journal: The Journal of steroid biochemistry and molecular biology 20060501

Title: Attenuation of mitogen- and stress-activated protein kinase-1-driven nuclear factor-kappaB gene expression by soy isoflavones does not require estrogenic activity.

Journal: Cancer research 20060501

Title: Determination of isoflavones in red clover by capillary electrophoresis with electrochemical detection.

Journal: Fitoterapia 20060401

Title: Thermal degradation kinetics of isoflavone aglycones from soy and red clover.

Journal: Molecular nutrition & food research 20060401

Title: The chemical and biologic profile of a red clover (Trifolium pratense L.) phase II clinical extract.

Journal: Journal of alternative and complementary medicine (New York, N.Y.) 20060301

Title: Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities.

Journal: Journal of natural products 20060101

Title: Estrogen-related receptors as emerging targets in cancer and metabolic disorders.

Journal: Current topics in medicinal chemistry 20060101

Title: Clinical studies of red clover (Trifolium pratense) dietary supplements in menopause: a literature review.

Journal: Menopause (New York, N.Y.) 20060101

Title: The selective estrogen receptor-beta agonist biochanin A shows vasculoprotective effects without uterotrophic activity.

Journal: Menopause (New York, N.Y.) 20060101

Title: Estimated intakes of isoflavones and coumestrol in Korean population.

Journal: International journal of food sciences and nutrition 20060101

Title: Human cytomegalovirus-inhibitory flavonoids: studies on antiviral activity and mechanism of action.

Journal: Antiviral research 20051201

Title: Suppression of arachidonic acid metabolism and nitric oxide formation by kudzu isoflavones in murine macrophages.

Journal: Molecular nutrition & food research 20051201

Title: Structural basis of inhibitor specificity of the human protooncogene proviral insertion site in moloney murine leukemia virus (PIM-1) kinase.

Journal: Journal of medicinal chemistry 20051201

Title: Flavonoids as a novel class of human organic anion-transporting polypeptide OATP1B1 (OATP-C) modulators.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20051101

Title: Differential modulation of ochratoxin A absorption across Caco-2 cells by dietary polyphenols, used at realistic intestinal concentrations.

Journal: Toxicology letters 20051015

Title: Reversal of hypermethylation and reactivation of p16INK4a, RARbeta, and MGMT genes by genistein and other isoflavones from soy.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20051001

Title: Biochanin A stimulates osteoblastic differentiation and inhibits hydrogen peroxide-induced production of inflammatory mediators in MC3T3-E1 cells.

Journal: Biological & pharmaceutical bulletin 20051001

Title: The phytoestrogen biochaninA weakens acute cardiac allograft rejection without affecting the reproductive system.

Journal: Transplant immunology 20051001

Title: Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense).

Journal: Journal of agricultural and food chemistry 20050810

Title: Metabolic engineering of isoflavonoid biosynthesis in alfalfa.

Journal: Plant physiology 20050801

Title: Dose-response effects of phytoestrogens on the activity and expression of 3beta-hydroxysteroid dehydrogenase and aromatase in human granulosa-luteal cells.

Journal: The Journal of steroid biochemistry and molecular biology 20050801

Title: Inhibition of P-glycoprotein by natural products in human breast cancer cells.

Journal: Archives of pharmacal research 20050701

Title: Synthesis and characterization of azole isoflavone inhibitors of aromatase.

Journal: Bioorganic & medicinal chemistry 20050602

Title: Changed isoflavone levels in red clover (Trifolium pratense L.) leaves with disturbed root nodulation in response to waterlogging.

Journal: Journal of chemical ecology 20050601

Title: 25-hydroxyvitamin D3-1alpha-hydroxylase is expressed in human vascular smooth muscle cells and is upregulated by parathyroid hormone and estrogenic compounds.

Journal: Circulation 20050405

Title: Membranal effects of phytoestrogens and carboxy derivatives of phytoestrogens on human vascular and bone cells: new insights based on studies with carboxy-biochanin A.

Journal: The Journal of steroid biochemistry and molecular biology 20050201

Title: Metabolic O-demethylation does not alter the influence of isoflavones on the biophysical properties of membranes and MRP1-like protein transport activity.

Journal: Archives of biochemistry and biophysics 20050115

Title: Differential induction of quinone reductase by phytoestrogens and protection against oestrogen-induced DNA damage.

Journal: The Biochemical journal 20050101

Title: [Studying the mechanism of antioxidant effect of vitamins and flavonoids].

Journal: Voprosy pitaniia 20050101

Title: Identification of urinary metabolites of the red clover isoflavones formononetin and biochanin A in human subjects.

Journal: Journal of agricultural and food chemistry 20041103

Title: Immunoassay for biochanin A.

Journal: Journal of immunological methods 20041101

Title: Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover).

Journal: Journal of agricultural and food chemistry 20041020

Title: Disposition of flavonoids via enteric recycling: enzyme-transporter coupling affects metabolism of biochanin A and formononetin and excretion of their phase II conjugates.

Journal: The Journal of pharmacology and experimental therapeutics 20040901

Title: Synthesis and aromatase inhibitory activity of novel pyridine-containing isoflavones.

Journal: Journal of medicinal chemistry 20040729

Title: Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport.

Journal: Molecular pharmacology 20040501

Title: The isoflavonoids genistein and quercetin activate different stress signaling pathways as shown by analysis of site-specific phosphorylation of ATM, p53 and histone H2AX.

Journal: DNA repair 20040304

Title: A biochanin-enriched isoflavone from red clover lowers LDL cholesterol in men.

Journal: European journal of clinical nutrition 20040301

Title: The effects of dietary supplementation with isoflavones from red clover on cognitive function in postmenopausal women.

Journal: Climacteric : the journal of the International Menopause Society 20040301

Title: Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors.

Journal: Analytical and bioanalytical chemistry 20040201

Title: Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.

Journal: The Journal of biological chemistry 20040109

Title: Red-clover-derived isoflavones and mammographic breast density: a double-blind, randomized, placebo-controlled trial [ISRCTN42940165].

Journal: Breast cancer research : BCR 20040101

Title: Natural products for dental caries prevention.

Journal: Journal of medicinal food 20040101

Title: Effect of red clover isoflavones on cox-2 activity in murine and human monocyte/macrophage cells.

Journal: Nutrition and cancer 20040101

Title: Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors.

Journal: Molecular cancer research : MCR 20031101

Title: Solution and solid state 13C NMR and X-ray studies of genistein complexes with amines. Potential biological function of the C-7, C-5, and C4'-OH groups.

Journal: Organic & biomolecular chemistry 20031021

Title: Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites.

Journal: Biochemical and biophysical research communications 20031010

Title: Assessment of the estrogenicity of isoflavonoids, using MCF-7-ERE-Luc cells.

Journal: Archives of pharmacal research 20030901

Title: Effect of the flavonoids biochanin A and silymarin on the P-glycoprotein-mediated transport of digoxin and vinblastine in human intestinal Caco-2 cells.

Journal: Pharmaceutical research 20030801

Title: Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20030701

Title: The red clover (Trifolium pratense) isoflavone biochanin A modulates the biotransformation pathways of 7,12-dimethylbenz[a]anthracene.

Journal: The British journal of nutrition 20030701

Title: Mass spectrometric methods for the analysis of chlorinated and nitrated isoflavonoids: a novel class of biological metabolites.

Journal: Journal of mass spectrometry : JMS 20030701

Title: Cell-transforming activity and mutagenicity of 5 phytoestrogens in cultured mammalian cells.

Journal: International journal of cancer 20030620

Title: Isoflavones reduce arterial stiffness: a placebo-controlled study in men and postmenopausal women.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20030601

Title: Anti-oxidant effect of flavonoids on the susceptibility of LDL oxidation.

Journal: Molecular and cellular biochemistry 20030401

Title: Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals.

Journal: Water research 20030301

Title: Effects of the flavonoids biochanin A, morin, phloretin, and silymarin on P-glycoprotein-mediated transport.

Journal: The Journal of pharmacology and experimental therapeutics 20030301

Title: Phytoestrogens inhibit aromatase but not 17beta-hydroxysteroid dehydrogenase (HSD) type 1 in human granulosa-luteal cells: evidence for FSH induction of 17beta-HSD.

Journal: Human reproduction (Oxford, England) 20030301

Title: Effect of flavonoids on MRP1-mediated transport in Panc-1 cells.

Journal: Journal of pharmaceutical sciences 20030201

Title: Effects of soy isoflavones on apoptosis induction and G2-M arrest in human hepatoma cells involvement of caspase-3 activation, Bcl-2 and Bcl-XL downregulation, and Cdc2 kinase activity.

Journal: Nutrition and cancer 20030101

Title: Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.

Journal: Journal of natural products 20021201

Title: Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.

Journal: Environmental toxicology and chemistry 20021101

Title: Identification and determination of ecdysones and flavonoids in Serratula strangulata by micellar electrokinetic capillary chromatography.

Journal: Planta medica 20021101

Title: Effect of fusaric acid and phytoanticipins on growth of rhizobacteria and Fusarium oxysporum.

Journal: Canadian journal of microbiology 20021101

Title: ESR and cell culture studies on free radical-scavenging and antioxidant activities of isoflavonoids.

Journal: Toxicology 20020930

Title: Metabolism of biochanin A and formononetin by human liver microsomes in vitro.

Journal: Journal of agricultural and food chemistry 20020814

Title: Mechanisms of the growth inhibitory effects of the isoflavonoid biochanin A on LNCaP cells and xenografts.

Journal: The Prostate 20020801

Title: Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.

Journal: Bioscience, biotechnology, and biochemistry 20020701

Title: Long-term pharmacokinetics of an extract of isoflavones from red clover (Trifolium pratense).

Journal: Journal of alternative and complementary medicine (New York, N.Y.) 20020401

Title: Detection of phytoestrogens in samples of second trimester human amniotic fluid.

Journal: Toxicology letters 20020328

Title: Flavonoids can block PSA production by breast and prostate cancer cell lines.

Journal: Clinica chimica acta; international journal of clinical chemistry 20020301

Title: Anticarcinogenic effects of isoflavones may be mediated by genistein in mouse mammary tumor virus-induced breast cancer.

Journal: Oncology 20020101

Title: Biochanin A similarly influences the fluidity of liposomes formed from charged and zwitterionic lipids.

Journal: Cellular & molecular biology letters 20020101

Title: Growth and cell cycle regulation by isoflavones in human breast carcinoma cells.

Journal: Reproduction, nutrition, development 20020101

Title: Effects of phytoestrogens on DNA synthesis and creatine kinase activity in vascular cells.

Journal: American journal of hypertension 20011201

Title: Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea.

Journal: Journal of agricultural and food chemistry 20011001

Title: The presence of three isoflavonoid compounds in Psoralea corylifolia.

Journal: Journal of chromatographic science 20011001

Title: Soy isoflavonoids and cancer -- metabolism at the target site.

Journal: Mutation research 20010901

Title: Growth inhibition of human endothelial cells by the phyto-oestrogen biochanin A, a metabolite of genistein.

Journal: The British journal of nutrition 20010501

Title: Three new phenolic compounds from a manipulated plant cell culture, Mirabilis jalapa.

Journal: Journal of natural products 20010301

Title: Direct inhibition of the hexose transporter GLUT1 by tyrosine kinase inhibitors.

Journal: Biochemistry 20010123

Title: Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.

Journal: Molecular and cellular endocrinology 20010122

Title: Inhibitors of human and rat testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD) as potential agents for prostatic cancer.

Journal: Journal of enzyme inhibition 20010101

Title: Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.

Journal: Anticancer research 20000101

Title: Expression of antioxidant proteins in human intestinal Caco-2 cells treated with dietary flavonoids.

Journal: Cancer letters 19991115

Title: Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.

Journal: Endocrinology 19981001

Title: Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study.

Journal: Environmental health perspectives 19980201

Title: Inhibition of HIV activation in latently infected cells by flavonoid compounds.

Journal: AIDS research and human retroviruses 19960101

Title: Thors L, et al. Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase. Br J Pharmacol. 2010 Jun;160(3):549-60.

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SDS
Tags:491-80-5 Molecular Formula|491-80-5 MDL|491-80-5 SMILES|491-80-5 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Catalog No.: AA00I8R7
491-80-5,MFCD00006839
491-80-5 | 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Pack Size: 1g
Purity: 98%
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$39.00 $27.00
Pack Size: 5g
Purity: 98%
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$99.00 $69.00
Pack Size: 10g
Purity: 98%
in stock
$154.00 $108.00
Pack Size: 25g
Purity: 98%
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$297.00 $208.00
Pack Size: 100g
Purity: 98%
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$520.00 $364.00
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Technical Information
Catalog Number: AA00I8R7
Chemical Name: 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
CAS Number: 491-80-5
Molecular Formula: C16H12O5
Molecular Weight: 284.2635
MDL Number: MFCD00006839
SMILES: COc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
NSC Number: 123538
Properties
Complexity: 424  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 21  
Hydrogen Bond Acceptor Count: 5  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 2  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 3  
Literature fold

Title: Red Clover Aryl Hydrocarbon Receptor (AhR) and Estrogen Receptor (ER) Agonists Enhance Genotoxic Estrogen Metabolism.

Journal: Chemical research in toxicology20171120

Title: Comparative Developmental Toxicity of Flavonoids Using an Integrative Zebrafish System.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20161101

Title: In vivo prediction of CYP-mediated metabolic interaction potential of formononetin and biochanin A using in vitro human and rat CYP450 inhibition data.

Journal: Toxicology letters20151119

Title: Isoflavones enhance interleukin-17 gene expression via retinoic acid receptor-related orphan receptors α and γ.

Journal: Toxicology20150302

Title: Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor.

Journal: Scientific reports20140101

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry20121115

Title: Phytotoxic effect, uptake, and transformation of biochanin A in selected weed species.

Journal: Journal of agricultural and food chemistry20121031

Title: Germination dramatically increases isoflavonoid content and diversity in chickpea (Cicer arietinum L.) seeds.

Journal: Journal of agricultural and food chemistry20120905

Title: Red clover extract ameliorates dyslipidemia in streptozotocin-induced diabetic C57BL/6 mice by activating hepatic PPARα.

Journal: Phytotherapy research : PTR20120601

Title: Effects of sodium selenite and germination on the sprouting of chickpeas (Cicer arietinum L.) and its content of selenium, formononetin and biochanin A in the sprouts.

Journal: Biological trace element research20120601

Title: Double-edged sword effect of biochanin to inhibit nuclear factor kappaB: suppression of serine/threonine and tyrosine kinases.

Journal: Biochemical pharmacology20120515

Title: Biotransformation of sophoricoside in Fructus sophorae by the fungus Schizophyllum commune.

Journal: Bioresource technology20120501

Title: Ester and carbamate ester derivatives of Biochanin A: synthesis and in vitro evaluation of estrogenic and antiproliferative activities.

Journal: Bioorganic & medicinal chemistry20120501

Title: Development of a new class of aromatase inhibitors: design, synthesis and inhibitory activity of 3-phenylchroman-4-one (isoflavanone) derivatives.

Journal: Bioorganic & medicinal chemistry20120415

Title: Effects of phytoestrogens derived from soy bean on expression of adhesion molecules on HUVEC.

Journal: Climacteric : the journal of the International Menopause Society20120401

Title: Identification of Genistein and Biochanin A by THz (far-infrared) vibrational spectra.

Journal: Journal of pharmaceutical and biomedical analysis20120325

Title: Effects of sodium metavanadate and germination on the sprouting of chickpeas and its content of vanadium, formononetin and biochanin A in the sprouts.

Journal: Journal of dietary supplements20120301

Title: Antihyperglycemic effect of biochanin A, a soy isoflavone, on streptozotocin-diabetic rats.

Journal: European journal of pharmacology20120215

Title: Reduced bioavailability of tamoxifen and its metabolite 4-hydroxytamoxifen after oral administration with biochanin A (an isoflavone) in rats.

Journal: Phytotherapy research : PTR20120201

Title: Constituents of Dalbergia sissoo Roxb. leaves with osteogenic activity.

Journal: Bioorganic & medicinal chemistry letters20120115

Title: Biochanin A ameliorates the cytokine secretion profile of lipopolysaccharide-stimulated macrophages by a PPARγ-dependent pathway.

Journal: Molecular medicine reports20120101

Title: Red clover and soy isoflavones--an in vitro safety assessment.

Journal: Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology20111201

Title: The sulfated conjugate of biochanin A is a substrate of breast cancer resistant protein (ABCG2).

Journal: Biopharmaceutics & drug disposition20111101

Title: Apoptotic effects of genistein, biochanin-A and apigenin on LNCaP and PC-3 cells by p21 through transcriptional inhibition of polo-like kinase-1.

Journal: Journal of Korean medical science20111101

Title: The cannabinoid receptor inverse agonist AM251 regulates the expression of the EGF receptor and its ligands via destabilization of oestrogen-related receptor α protein.

Journal: British journal of pharmacology20111001

Title: Liquid chromatography-mass spectrometry method for the quantification of tamoxifen and its metabolite 4-hydroxytamoxifen in rat plasma: application to interaction study with biochanin A (an isoflavone).

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences20111001

Title: Modulatory effects of curcumin on multi-drug resistance-associated protein 5 in pancreatic cancer cells.

Journal: Cancer chemotherapy and pharmacology20110901

Title: Improved effectiveness of biochanin A as a P-gp inhibitor in solid dispersion.

Journal: Die Pharmazie20110901

Title: [Establishment and application of co-transfection screening method for phytoestrogen active constituents].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica20110901

Title: Enhanced dissolution and bioavailability of biochanin A via the preparation of solid dispersion: in vitro and in vivo evaluation.

Journal: International journal of pharmaceutics20110830

Title: Synergistic chemoprotective mechanisms of dietary phytoestrogens in a select combination against prostate cancer.

Journal: The Journal of nutritional biochemistry20110801

Title: LC-ESI-MS characterisation of phytoalexins induced in chickpea and pea tissues in response to a biotic elicitor of Hypnea musciformis (red algae).

Journal: Natural product research20110801

Title: Structural requirements of flavonoids for the adipogenesis of 3T3-L1 cells.

Journal: Bioorganic & medicinal chemistry20110501

Title: Biochanin-A, an isoflavon, showed anti-proliferative and anti-inflammatory activities through the inhibition of iNOS expression, p38-MAPK and ATF-2 phosphorylation and blocking NFκB nuclear translocation.

Journal: European journal of pharmacology20110225

Title: Quantification of five isoflavones and coumestrol in various solid agroenvironmental matrices using ¹³c₃-labeled internal standards.

Journal: Journal of agricultural and food chemistry20110209

Title: The effects of native and synthetic estrogenic compounds as well as vitamin D less-calcemic analogs on adipocytes content in rat bone marrow.

Journal: Journal of endocrinological investigation20110201

Title: The effects of estrogen receptors α- and β-specific agonists and antagonists on cell proliferation and energy metabolism in human bone cell line.

Journal: Journal of cellular biochemistry20110201

Title: In vitro and in vivo melanogenesis inhibition by biochanin A from Trifolium pratense.

Journal: Bioscience, biotechnology, and biochemistry20110101

Title: High-throughput quantification of isoflavones, biochanin A and genistein, and their conjugates in female rat plasma using LC-ESI-MS/MS: Application in pharmacokinetic study.

Journal: Journal of separation science20101101

Title: The characterisation of structural and antioxidant properties of isoflavone metal chelates.

Journal: Journal of inorganic biochemistry20101001

Title: Biochanin A reduces drug-induced p75NTR expression and enhances cell survival: a new in vitro assay for screening inhibitors of p75NTR expression.

Journal: Rejuvenation research20101001

Title: Phenolic compounds from Pueraria lobata protect PC12 cells against Aβ-induced toxicity.

Journal: Archives of pharmacal research20101001

Title: Antimicrobial effect of red clover (Trifolium pratense) phenolic extract on the ruminal hyper ammonia-producing bacterium, Clostridium sticklandii.

Journal: Current microbiology20100801

Title: An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.

Journal: Journal of natural products20100723

Title: LC-MSMS profiling of flavonoid conjugates in wild Mexican lupine, Lupinus reflexus.

Journal: Journal of natural products20100723

Title: Effect of combination treatment of rapamycin and isoflavones on mTOR pathway in human glioblastoma (U87) cells.

Journal: Neurochemical research20100701

Title: New flavonoids with 2BS cell proliferation promoting effect from the seeds of Trigonella foenum-graecum L.

Journal: Journal of natural medicines20100701

Title: Effects of the isoflavonoid biochanin A on the transport of mitoxantrone in vitro and in vivo.

Journal: Biopharmaceutics & drug disposition20100701

Title: Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase.

Journal: British journal of pharmacology20100601

Title: Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19).

Journal: Bioorganic & medicinal chemistry letters20100515

Title: Syntheses, characterization and antitumor activities of transition metal complexes with isoflavone.

Journal: Journal of inorganic biochemistry20100401

Title: Selective growth inhibitory effect of biochanin A against intestinal tract colonizing bacteria.

Journal: Molecules (Basel, Switzerland)20100303

Title: Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications.

Journal: Toxicology letters20100215

Title: Interactions between the flavonoid biochanin A and P-glycoprotein substrates in rats: in vitro and in vivo.

Journal: Journal of pharmaceutical sciences20100101

Title: Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.

Journal: Bioorganic & medicinal chemistry20100101

Title: Biochanin A induction of sulfotransferases in rats.

Journal: Journal of biochemical and molecular toxicology20100101

Title: Novel screening method for potential skin-whitening compounds by a luciferase reporter assay.

Journal: Bioscience, biotechnology, and biochemistry20100101

Title: Spatial distribution and quantification of endocrine-disrupting chemicals in Sado River estuary, Portugal.

Journal: Environmental monitoring and assessment20091201

Title: Inhibition of angiogenesis and inflammation by an extract of red clover (Trifolium pratense L.).

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology20091201

Title: Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells.

Journal: Journal of natural products20091201

Title: Quantification of phytoestrogens in industrial waste streams.

Journal: Environmental toxicology and chemistry20091101

Title: Cellular DNA breakage by soy isoflavone genistein and its methylated structural analogue biochanin A.

Journal: Molecular nutrition & food research20091101

Title: Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay.

Journal: Bioorganic & medicinal chemistry letters20090815

Title: Modulatory influence of prepubertal biochanin A exposure on mammary gland differentiation and expression of estrogen receptor-alpha and apoptotic proteins.

Journal: Phytotherapy research : PTR20090701

Title: Pressurized liquid extraction versus other extraction techniques in micropreparative isolation of pharmacologically active isoflavones from Trifolium L. species.

Journal: Talanta20090630

Title: Single amino acid mutations of Medicago glycosyltransferase UGT85H2 enhance activity and impart reversibility.

Journal: FEBS letters20090618

Title: AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.

Journal: Chemico-biological interactions20090316

Title: Determination and pharmacokinetic study of taxifolin in rabbit plasma by high-performance liquid chromatography.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology20090301

Title: The isoflavones mixture from Trifolium pratense L. protects HCN 1-A neurons from oxidative stress.

Journal: Phytotherapy research : PTR20090201

Title: Effect of frequency and duration of ultrasonication on the extraction efficiency of selected isoflavones and trans-resveratrol from peanuts (Arachis hypogaea).

Journal: Ultrasonics sonochemistry20090201

Title: Discovery of a potent and selective inhibitor for human carbonyl reductase 1 from propionate scanning applied to the macrolide zearalenone.

Journal: Bioorganic & medicinal chemistry20090115

Title: Antiparasitic activity of biochanin A, an isolated isoflavone from fruits of Cassia fistula (Leguminosae).

Journal: Parasitology research20090101

Title: Effects of dietary phytoestrogens on plasma testosterone and triiodothyronine (T3) levels in male goat kids.

Journal: Acta veterinaria Scandinavica20090101

Title: Establishment of a transgenic yeast screening system for estrogenicity and identification of the anti-estrogenic activity of malachite green.

Journal: Journal of cellular biochemistry20081215

Title: Biochanin A inhibits breast cancer tumor growth in a murine xenograft model.

Journal: Pharmaceutical research20080901

Title: Plant phenolic compounds as ethidium bromide efflux inhibitors in Mycobacterium smegmatis.

Journal: The Journal of antimicrobial chemotherapy20080801

Title: Effect of mycorrhization on the isoflavone content and the phytoestrogen activity of red clover.

Journal: Journal of plant physiology20080731

Title: Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.

Journal: Journal of medicinal chemistry20080724

Title: Ultrahigh-pressure liquid chromatography of isoflavones and phenolic acids on different stationary phases.

Journal: Journal of chromatography. A20080627

Title: Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).

Journal: Journal of medicinal chemistry20080612

Title: Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.

Journal: Bioorganic & medicinal chemistry20080515

Title: Chemoprevention of mammary tumorigenesis and chemomodulation of the antioxidative enzymes and peroxidative damage in prepubertal Sprague Dawley rats by Biochanin A.

Journal: Molecular and cellular biochemistry20080501

Title: Daidzein but not other phytoestrogens preserves bone architecture in ovariectomized female rats in vivo.

Journal: Journal of cellular biochemistry20080415

Title: Topical isoflavones provide effective photoprotection to skin.

Journal: Photodermatology, photoimmunology & photomedicine20080401

Title: Variable isoflavone content of red clover products affects intestinal disposition of biochanin A, formononetin, genistein, and daidzein.

Journal: Journal of alternative and complementary medicine (New York, N.Y.)20080401

Title: The red clover (Trifolium pratense) isoflavone biochanin A inhibits aromatase activity and expression.

Journal: The British journal of nutrition20080201

Title: Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition.

Journal: Bioorganic & medicinal chemistry20080101

Title: Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor.

Journal: The Journal of steroid biochemistry and molecular biology20080101

Title: NMR spectral assignments of a new [C--O--C] isoflavone dimer from Andira surinamensis.

Journal: Magnetic resonance in chemistry : MRC20080101

Title: Isoflavonoid glycosides and rotenoids from Pongamia pinnata leaves.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences20080101

Title: Oestrogen receptor alpha is required for biochanin A-induced apolipoprotein A-1 mRNA expression in HepG2 cells.

Journal: The British journal of nutrition20070901

Title: Optimization of a rapid microwave assisted extraction method for the liquid chromatography-electrospray-tandem mass spectrometry determination of isoflavonoid aglycones in soybeans.

Journal: Journal of chromatography. A20070608

Title: Yeast-based screening to identify modulators of G-protein signaling using uncontrolled cell division cycle by overexpression of Stm1.

Journal: Journal of biotechnology20070501

Title: Biochanin A protects dopaminergic neurons against lipopolysaccharide-induced damage through inhibition of microglia activation and proinflammatory factors generation.

Journal: Neuroscience letters20070501

Title: Effects of the flavonoid biochanin A on gene expression in primary human hepatocytes and human intestinal cells.

Journal: Molecular nutrition & food research20070301

Title: Evaluation of matrix effects in metabolite profiling based on capillary liquid chromatography electrospray ionization quadrupole time-of-flight mass spectrometry.

Journal: Analytical chemistry20070215

Title: Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.

Journal: Drug metabolism and disposition: the biological fate of chemicals20070201

Title: [Chemical constituents of isoflavones from vine stems of Millettia nitita var. hirsutissima].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica20070201

Title: Nicotine and biochanin A, but not cigarette smoke, induce anti-inflammatory effects on keratinocytes and endothelial cells in patients with Behçet's disease.

Journal: The Journal of investigative dermatology20070101

Title: Effects of flavonoids genistein and biochanin a on gene expression and their metabolism in human mammary cells.

Journal: Nutrition and cancer20070101

Title: 25 hydroxy-vitamin D(3)-1alpha hydroxylase expression and activity in cultured human osteoblasts and their modulation by parathyroid hormone, estrogenic compounds and dihydrotestosterone.

Journal: The Journal of steroid biochemistry and molecular biology20070101

Title: Pharmacokinetics and bioavailability of the bioflavonoid biochanin A: effects of quercetin and EGCG on biochanin A disposition in rats.

Journal: Molecular pharmaceutics20070101

Title: Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.

Journal: Journal of molecular graphics & modelling20061101

Title: Phytoestrogens and their low dose combinations inhibit mRNA expression and activity of aromatase in human granulosa-luteal cells.

Journal: The Journal of steroid biochemistry and molecular biology20061101

Title: Inhibition of matrix degrading enzymes and invasion in human glioblastoma (U87MG) cells by isoflavones.

Journal: Journal of neuro-oncology20060901

Title: Altered oral bioavailability and pharmacokinetics of P-glycoprotein substrates by coadministration of biochanin A.

Journal: Journal of pharmaceutical sciences20060901

Title: Mechanisms underlying biochanin A-induced relaxation of the aorta differ between normotensive and hypertensive rats.

Journal: Clinical and experimental pharmacology & physiology20060901

Title: Pharmacokinetics and bioavailability of the isoflavone biochanin A in rats.

Journal: The AAPS journal20060901

Title: Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages.

Journal: Journal of agricultural and food chemistry20060809

Title: [Endothelium-independent vasorelaxation of plant-derived estrogen biochanin A and its mechanism in rat aortic rings].

Journal: Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology20060801

Title: A comparative study on the protective effects of 17beta-estradiol, biochanin A and bisphenol A on mammary gland differentiation and tumorigenesis in rats.

Journal: Indian journal of experimental biology20060701

Title: Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells.

Journal: Archives of pharmacal research20060701

Title: Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.

Journal: Journal of medicinal chemistry20060601

Title: Up-regulation of interleukin-4 production via NF-AT/AP-1 activation in T cells by biochanin A, a phytoestrogen and its metabolites.

Journal: Toxicology and applied pharmacology20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology20060501

Title: Responsiveness to estradiol-17beta and to phytoestrogens in primary human osteoblasts is modulated differentially by high glucose concentration.

Journal: The Journal of steroid biochemistry and molecular biology20060501

Title: Attenuation of mitogen- and stress-activated protein kinase-1-driven nuclear factor-kappaB gene expression by soy isoflavones does not require estrogenic activity.

Journal: Cancer research20060501

Title: Determination of isoflavones in red clover by capillary electrophoresis with electrochemical detection.

Journal: Fitoterapia20060401

Title: Thermal degradation kinetics of isoflavone aglycones from soy and red clover.

Journal: Molecular nutrition & food research20060401

Title: The chemical and biologic profile of a red clover (Trifolium pratense L.) phase II clinical extract.

Journal: Journal of alternative and complementary medicine (New York, N.Y.)20060301

Title: Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities.

Journal: Journal of natural products20060101

Title: Estrogen-related receptors as emerging targets in cancer and metabolic disorders.

Journal: Current topics in medicinal chemistry20060101

Title: Clinical studies of red clover (Trifolium pratense) dietary supplements in menopause: a literature review.

Journal: Menopause (New York, N.Y.)20060101

Title: The selective estrogen receptor-beta agonist biochanin A shows vasculoprotective effects without uterotrophic activity.

Journal: Menopause (New York, N.Y.)20060101

Title: Estimated intakes of isoflavones and coumestrol in Korean population.

Journal: International journal of food sciences and nutrition20060101

Title: Human cytomegalovirus-inhibitory flavonoids: studies on antiviral activity and mechanism of action.

Journal: Antiviral research20051201

Title: Suppression of arachidonic acid metabolism and nitric oxide formation by kudzu isoflavones in murine macrophages.

Journal: Molecular nutrition & food research20051201

Title: Structural basis of inhibitor specificity of the human protooncogene proviral insertion site in moloney murine leukemia virus (PIM-1) kinase.

Journal: Journal of medicinal chemistry20051201

Title: Flavonoids as a novel class of human organic anion-transporting polypeptide OATP1B1 (OATP-C) modulators.

Journal: Drug metabolism and disposition: the biological fate of chemicals20051101

Title: Differential modulation of ochratoxin A absorption across Caco-2 cells by dietary polyphenols, used at realistic intestinal concentrations.

Journal: Toxicology letters20051015

Title: Reversal of hypermethylation and reactivation of p16INK4a, RARbeta, and MGMT genes by genistein and other isoflavones from soy.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20051001

Title: Biochanin A stimulates osteoblastic differentiation and inhibits hydrogen peroxide-induced production of inflammatory mediators in MC3T3-E1 cells.

Journal: Biological & pharmaceutical bulletin20051001

Title: The phytoestrogen biochaninA weakens acute cardiac allograft rejection without affecting the reproductive system.

Journal: Transplant immunology20051001

Title: Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense).

Journal: Journal of agricultural and food chemistry20050810

Title: Metabolic engineering of isoflavonoid biosynthesis in alfalfa.

Journal: Plant physiology20050801

Title: Dose-response effects of phytoestrogens on the activity and expression of 3beta-hydroxysteroid dehydrogenase and aromatase in human granulosa-luteal cells.

Journal: The Journal of steroid biochemistry and molecular biology20050801

Title: Inhibition of P-glycoprotein by natural products in human breast cancer cells.

Journal: Archives of pharmacal research20050701

Title: Synthesis and characterization of azole isoflavone inhibitors of aromatase.

Journal: Bioorganic & medicinal chemistry20050602

Title: Changed isoflavone levels in red clover (Trifolium pratense L.) leaves with disturbed root nodulation in response to waterlogging.

Journal: Journal of chemical ecology20050601

Title: 25-hydroxyvitamin D3-1alpha-hydroxylase is expressed in human vascular smooth muscle cells and is upregulated by parathyroid hormone and estrogenic compounds.

Journal: Circulation20050405

Title: Membranal effects of phytoestrogens and carboxy derivatives of phytoestrogens on human vascular and bone cells: new insights based on studies with carboxy-biochanin A.

Journal: The Journal of steroid biochemistry and molecular biology20050201

Title: Metabolic O-demethylation does not alter the influence of isoflavones on the biophysical properties of membranes and MRP1-like protein transport activity.

Journal: Archives of biochemistry and biophysics20050115

Title: Differential induction of quinone reductase by phytoestrogens and protection against oestrogen-induced DNA damage.

Journal: The Biochemical journal20050101

Title: [Studying the mechanism of antioxidant effect of vitamins and flavonoids].

Journal: Voprosy pitaniia20050101

Title: Identification of urinary metabolites of the red clover isoflavones formononetin and biochanin A in human subjects.

Journal: Journal of agricultural and food chemistry20041103

Title: Immunoassay for biochanin A.

Journal: Journal of immunological methods20041101

Title: Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover).

Journal: Journal of agricultural and food chemistry20041020

Title: Disposition of flavonoids via enteric recycling: enzyme-transporter coupling affects metabolism of biochanin A and formononetin and excretion of their phase II conjugates.

Journal: The Journal of pharmacology and experimental therapeutics20040901

Title: Synthesis and aromatase inhibitory activity of novel pyridine-containing isoflavones.

Journal: Journal of medicinal chemistry20040729

Title: Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport.

Journal: Molecular pharmacology20040501

Title: The isoflavonoids genistein and quercetin activate different stress signaling pathways as shown by analysis of site-specific phosphorylation of ATM, p53 and histone H2AX.

Journal: DNA repair20040304

Title: A biochanin-enriched isoflavone from red clover lowers LDL cholesterol in men.

Journal: European journal of clinical nutrition20040301

Title: The effects of dietary supplementation with isoflavones from red clover on cognitive function in postmenopausal women.

Journal: Climacteric : the journal of the International Menopause Society20040301

Title: Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors.

Journal: Analytical and bioanalytical chemistry20040201

Title: Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.

Journal: The Journal of biological chemistry20040109

Title: Red-clover-derived isoflavones and mammographic breast density: a double-blind, randomized, placebo-controlled trial [ISRCTN42940165].

Journal: Breast cancer research : BCR20040101

Title: Natural products for dental caries prevention.

Journal: Journal of medicinal food20040101

Title: Effect of red clover isoflavones on cox-2 activity in murine and human monocyte/macrophage cells.

Journal: Nutrition and cancer20040101

Title: Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors.

Journal: Molecular cancer research : MCR20031101

Title: Solution and solid state 13C NMR and X-ray studies of genistein complexes with amines. Potential biological function of the C-7, C-5, and C4'-OH groups.

Journal: Organic & biomolecular chemistry20031021

Title: Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites.

Journal: Biochemical and biophysical research communications20031010

Title: Assessment of the estrogenicity of isoflavonoids, using MCF-7-ERE-Luc cells.

Journal: Archives of pharmacal research20030901

Title: Effect of the flavonoids biochanin A and silymarin on the P-glycoprotein-mediated transport of digoxin and vinblastine in human intestinal Caco-2 cells.

Journal: Pharmaceutical research20030801

Title: Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones.

Journal: Drug metabolism and disposition: the biological fate of chemicals20030701

Title: The red clover (Trifolium pratense) isoflavone biochanin A modulates the biotransformation pathways of 7,12-dimethylbenz[a]anthracene.

Journal: The British journal of nutrition20030701

Title: Mass spectrometric methods for the analysis of chlorinated and nitrated isoflavonoids: a novel class of biological metabolites.

Journal: Journal of mass spectrometry : JMS20030701

Title: Cell-transforming activity and mutagenicity of 5 phytoestrogens in cultured mammalian cells.

Journal: International journal of cancer20030620

Title: Isoflavones reduce arterial stiffness: a placebo-controlled study in men and postmenopausal women.

Journal: Arteriosclerosis, thrombosis, and vascular biology20030601

Title: Anti-oxidant effect of flavonoids on the susceptibility of LDL oxidation.

Journal: Molecular and cellular biochemistry20030401

Title: Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals.

Journal: Water research20030301

Title: Effects of the flavonoids biochanin A, morin, phloretin, and silymarin on P-glycoprotein-mediated transport.

Journal: The Journal of pharmacology and experimental therapeutics20030301

Title: Phytoestrogens inhibit aromatase but not 17beta-hydroxysteroid dehydrogenase (HSD) type 1 in human granulosa-luteal cells: evidence for FSH induction of 17beta-HSD.

Journal: Human reproduction (Oxford, England)20030301

Title: Effect of flavonoids on MRP1-mediated transport in Panc-1 cells.

Journal: Journal of pharmaceutical sciences20030201

Title: Effects of soy isoflavones on apoptosis induction and G2-M arrest in human hepatoma cells involvement of caspase-3 activation, Bcl-2 and Bcl-XL downregulation, and Cdc2 kinase activity.

Journal: Nutrition and cancer20030101

Title: Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.

Journal: Journal of natural products20021201

Title: Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.

Journal: Environmental toxicology and chemistry20021101

Title: Identification and determination of ecdysones and flavonoids in Serratula strangulata by micellar electrokinetic capillary chromatography.

Journal: Planta medica20021101

Title: Effect of fusaric acid and phytoanticipins on growth of rhizobacteria and Fusarium oxysporum.

Journal: Canadian journal of microbiology20021101

Title: ESR and cell culture studies on free radical-scavenging and antioxidant activities of isoflavonoids.

Journal: Toxicology20020930

Title: Metabolism of biochanin A and formononetin by human liver microsomes in vitro.

Journal: Journal of agricultural and food chemistry20020814

Title: Mechanisms of the growth inhibitory effects of the isoflavonoid biochanin A on LNCaP cells and xenografts.

Journal: The Prostate20020801

Title: Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.

Journal: Bioscience, biotechnology, and biochemistry20020701

Title: Long-term pharmacokinetics of an extract of isoflavones from red clover (Trifolium pratense).

Journal: Journal of alternative and complementary medicine (New York, N.Y.)20020401

Title: Detection of phytoestrogens in samples of second trimester human amniotic fluid.

Journal: Toxicology letters20020328

Title: Flavonoids can block PSA production by breast and prostate cancer cell lines.

Journal: Clinica chimica acta; international journal of clinical chemistry20020301

Title: Anticarcinogenic effects of isoflavones may be mediated by genistein in mouse mammary tumor virus-induced breast cancer.

Journal: Oncology20020101

Title: Biochanin A similarly influences the fluidity of liposomes formed from charged and zwitterionic lipids.

Journal: Cellular & molecular biology letters20020101

Title: Growth and cell cycle regulation by isoflavones in human breast carcinoma cells.

Journal: Reproduction, nutrition, development20020101

Title: Effects of phytoestrogens on DNA synthesis and creatine kinase activity in vascular cells.

Journal: American journal of hypertension20011201

Title: Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea.

Journal: Journal of agricultural and food chemistry20011001

Title: The presence of three isoflavonoid compounds in Psoralea corylifolia.

Journal: Journal of chromatographic science20011001

Title: Soy isoflavonoids and cancer -- metabolism at the target site.

Journal: Mutation research20010901

Title: Growth inhibition of human endothelial cells by the phyto-oestrogen biochanin A, a metabolite of genistein.

Journal: The British journal of nutrition20010501

Title: Three new phenolic compounds from a manipulated plant cell culture, Mirabilis jalapa.

Journal: Journal of natural products20010301

Title: Direct inhibition of the hexose transporter GLUT1 by tyrosine kinase inhibitors.

Journal: Biochemistry20010123

Title: Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.

Journal: Molecular and cellular endocrinology20010122

Title: Inhibitors of human and rat testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD) as potential agents for prostatic cancer.

Journal: Journal of enzyme inhibition20010101

Title: Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.

Journal: Anticancer research20000101

Title: Expression of antioxidant proteins in human intestinal Caco-2 cells treated with dietary flavonoids.

Journal: Cancer letters19991115

Title: Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.

Journal: Endocrinology19981001

Title: Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study.

Journal: Environmental health perspectives19980201

Title: Inhibition of HIV activation in latently infected cells by flavonoid compounds.

Journal: AIDS research and human retroviruses19960101

Title: Thors L, et al. Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase. Br J Pharmacol. 2010 Jun;160(3):549-60.

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