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

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$37.00	$26.00
5g	98%	in stock	$98.00	$69.00
10g	98%	in stock	$155.00	$108.00
25g	98%	in stock	$299.00	$209.00
100g	98%	in stock	$511.00	$358.00

Description

• Catalog Number: AI51055
• 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

Computed Properties

• Complexity: 424
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 21
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 2
• XLogP3: 3

Literature

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

  Chemical research in toxicology 20171120

• Comparative Developmental Toxicity of Flavonoids Using an Integrative Zebrafish System.

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

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

  Toxicology letters 20151119

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

  Toxicology 20150302

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

  Scientific reports 20140101

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

  Bioorganic & medicinal chemistry 20121115

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

  Journal of agricultural and food chemistry 20121031

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

  Journal of agricultural and food chemistry 20120905

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

  Phytotherapy research : PTR 20120601

• 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.

  Biological trace element research 20120601

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

  Biochemical pharmacology 20120515

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

  Bioresource technology 20120501

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

  Bioorganic & medicinal chemistry 20120501

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

  Bioorganic & medicinal chemistry 20120415

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

  Climacteric : the journal of the International Menopause Society 20120401

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

  Journal of pharmaceutical and biomedical analysis 20120325

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

  Journal of dietary supplements 20120301

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

  European journal of pharmacology 20120215

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

  Phytotherapy research : PTR 20120201

• Constituents of Dalbergia sissoo Roxb. leaves with osteogenic activity.

  Bioorganic & medicinal chemistry letters 20120115

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

  Molecular medicine reports 20120101

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

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

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

  Biopharmaceutics & drug disposition 20111101

• 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 of Korean medical science 20111101

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

  British journal of pharmacology 20111001

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

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

  Cancer chemotherapy and pharmacology 20110901

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

  Die Pharmazie 20110901

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

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

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

  International journal of pharmaceutics 20110830

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

  The Journal of nutritional biochemistry 20110801

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

  Natural product research 20110801

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

  Bioorganic & medicinal chemistry 20110501

• 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.

  European journal of pharmacology 20110225

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

  Journal of agricultural and food chemistry 20110209

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

  Journal of endocrinological investigation 20110201

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

  Journal of cellular biochemistry 20110201

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

  Bioscience, biotechnology, and biochemistry 20110101

• 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 of separation science 20101101

• The characterisation of structural and antioxidant properties of isoflavone metal chelates.

  Journal of inorganic biochemistry 20101001

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

  Rejuvenation research 20101001

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

  Archives of pharmacal research 20101001

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

  Current microbiology 20100801

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

  Journal of natural products 20100723

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

  Journal of natural products 20100723

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

  Neurochemical research 20100701

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

  Journal of natural medicines 20100701

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

  Biopharmaceutics & drug disposition 20100701

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

  British journal of pharmacology 20100601

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

  Bioorganic & medicinal chemistry letters 20100515

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

  Journal of inorganic biochemistry 20100401

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

  Molecules (Basel, Switzerland) 20100303

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

  Toxicology letters 20100215

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

  Journal of pharmaceutical sciences 20100101

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

  Bioorganic & medicinal chemistry 20100101

• Biochanin A induction of sulfotransferases in rats.

  Journal of biochemical and molecular toxicology 20100101

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

  Bioscience, biotechnology, and biochemistry 20100101

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

  Environmental monitoring and assessment 20091201

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

  Phytomedicine : international journal of phytotherapy and phytopharmacology 20091201

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

  Journal of natural products 20091201

• Quantification of phytoestrogens in industrial waste streams.

  Environmental toxicology and chemistry 20091101

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

  Molecular nutrition & food research 20091101

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

  Bioorganic & medicinal chemistry letters 20090815

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

  Phytotherapy research : PTR 20090701

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

  Talanta 20090630

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

  FEBS letters 20090618

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

  Chemico-biological interactions 20090316

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

  Phytomedicine : international journal of phytotherapy and phytopharmacology 20090301

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

  Phytotherapy research : PTR 20090201

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

  Ultrasonics sonochemistry 20090201

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

  Bioorganic & medicinal chemistry 20090115

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

  Parasitology research 20090101

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

  Acta veterinaria Scandinavica 20090101

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

  Journal of cellular biochemistry 20081215

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

  Pharmaceutical research 20080901

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

  The Journal of antimicrobial chemotherapy 20080801

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

  Journal of plant physiology 20080731

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

  Journal of medicinal chemistry 20080724

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

  Journal of chromatography. A 20080627

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

  Journal of medicinal chemistry 20080612

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

  Bioorganic & medicinal chemistry 20080515

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

  Molecular and cellular biochemistry 20080501

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

  Journal of cellular biochemistry 20080415

• Topical isoflavones provide effective photoprotection to skin.

  Photodermatology, photoimmunology & photomedicine 20080401

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

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

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

  The British journal of nutrition 20080201

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

  Bioorganic & medicinal chemistry 20080101

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

  The Journal of steroid biochemistry and molecular biology 20080101

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

  Magnetic resonance in chemistry : MRC 20080101

• Isoflavonoid glycosides and rotenoids from Pongamia pinnata leaves.

  Zeitschrift fur Naturforschung. C, Journal of biosciences 20080101

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

  The British journal of nutrition 20070901

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

  Journal of chromatography. A 20070608

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

  Journal of biotechnology 20070501

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

  Neuroscience letters 20070501

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

  Molecular nutrition & food research 20070301

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

  Analytical chemistry 20070215

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

  Drug metabolism and disposition: the biological fate of chemicals 20070201

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

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

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

  The Journal of investigative dermatology 20070101

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

  Nutrition and cancer 20070101

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

  The Journal of steroid biochemistry and molecular biology 20070101

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

  Molecular pharmaceutics 20070101

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

  Journal of molecular graphics & modelling 20061101

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

  The Journal of steroid biochemistry and molecular biology 20061101

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

  Journal of neuro-oncology 20060901

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

  Journal of pharmaceutical sciences 20060901

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

  Clinical and experimental pharmacology & physiology 20060901

• Pharmacokinetics and bioavailability of the isoflavone biochanin A in rats.

  The AAPS journal 20060901

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

  Journal of agricultural and food chemistry 20060809

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

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

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

  Indian journal of experimental biology 20060701

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

  Archives of pharmacal research 20060701

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

  Journal of medicinal chemistry 20060601

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

  Toxicology and applied pharmacology 20060501

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

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

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

  The Journal of steroid biochemistry and molecular biology 20060501

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

  Cancer research 20060501

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

  Fitoterapia 20060401

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

  Molecular nutrition & food research 20060401

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

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

• Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities.

  Journal of natural products 20060101

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

  Current topics in medicinal chemistry 20060101

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

  Menopause (New York, N.Y.) 20060101

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

  Menopause (New York, N.Y.) 20060101

• Estimated intakes of isoflavones and coumestrol in Korean population.

  International journal of food sciences and nutrition 20060101

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

  Antiviral research 20051201

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

  Molecular nutrition & food research 20051201

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

  Journal of medicinal chemistry 20051201

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

  Drug metabolism and disposition: the biological fate of chemicals 20051101

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

  Toxicology letters 20051015

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

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

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

  Biological & pharmaceutical bulletin 20051001

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

  Transplant immunology 20051001

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

  Journal of agricultural and food chemistry 20050810

• Metabolic engineering of isoflavonoid biosynthesis in alfalfa.

  Plant physiology 20050801

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

  The Journal of steroid biochemistry and molecular biology 20050801

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

  Archives of pharmacal research 20050701

• Synthesis and characterization of azole isoflavone inhibitors of aromatase.

  Bioorganic & medicinal chemistry 20050602

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

  Journal of chemical ecology 20050601

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

  Circulation 20050405

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

  The Journal of steroid biochemistry and molecular biology 20050201

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

  Archives of biochemistry and biophysics 20050115

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

  The Biochemical journal 20050101

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

  Voprosy pitaniia 20050101

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

  Journal of agricultural and food chemistry 20041103

• Immunoassay for biochanin A.

  Journal of immunological methods 20041101

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

  Journal of agricultural and food chemistry 20041020

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

  The Journal of pharmacology and experimental therapeutics 20040901

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

  Journal of medicinal chemistry 20040729

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

  Molecular pharmacology 20040501

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

  DNA repair 20040304

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

  European journal of clinical nutrition 20040301

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

  Climacteric : the journal of the International Menopause Society 20040301

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

  Analytical and bioanalytical chemistry 20040201

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

  The Journal of biological chemistry 20040109

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

  Breast cancer research : BCR 20040101

• Natural products for dental caries prevention.

  Journal of medicinal food 20040101

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

  Nutrition and cancer 20040101

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

  Molecular cancer research : MCR 20031101

• 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.

  Organic & biomolecular chemistry 20031021

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

  Biochemical and biophysical research communications 20031010

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

  Archives of pharmacal research 20030901

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

  Pharmaceutical research 20030801

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

  Drug metabolism and disposition: the biological fate of chemicals 20030701

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

  The British journal of nutrition 20030701

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

  Journal of mass spectrometry : JMS 20030701

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

  International journal of cancer 20030620

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

  Arteriosclerosis, thrombosis, and vascular biology 20030601

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

  Molecular and cellular biochemistry 20030401

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

  Water research 20030301

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

  The Journal of pharmacology and experimental therapeutics 20030301

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

  Human reproduction (Oxford, England) 20030301

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

  Journal of pharmaceutical sciences 20030201

• 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.

  Nutrition and cancer 20030101

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

  Journal of natural products 20021201

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

  Environmental toxicology and chemistry 20021101

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

  Planta medica 20021101

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

  Canadian journal of microbiology 20021101

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

  Toxicology 20020930

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

  Journal of agricultural and food chemistry 20020814

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

  The Prostate 20020801

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

  Bioscience, biotechnology, and biochemistry 20020701

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

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

• Detection of phytoestrogens in samples of second trimester human amniotic fluid.

  Toxicology letters 20020328

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

  Clinica chimica acta; international journal of clinical chemistry 20020301

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

  Oncology 20020101

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

  Cellular & molecular biology letters 20020101

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

  Reproduction, nutrition, development 20020101

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

  American journal of hypertension 20011201

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

  Journal of agricultural and food chemistry 20011001

• The presence of three isoflavonoid compounds in Psoralea corylifolia.

  Journal of chromatographic science 20011001

• Soy isoflavonoids and cancer -- metabolism at the target site.

  Mutation research 20010901

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

  The British journal of nutrition 20010501

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

  Journal of natural products 20010301

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

  Biochemistry 20010123

• Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.

  Molecular and cellular endocrinology 20010122

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

  Journal of enzyme inhibition 20010101

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

  Anticancer research 20000101

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

  Cancer letters 19991115

• Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.

  Endocrinology 19981001

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

  Environmental health perspectives 19980201

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

  AIDS research and human retroviruses 19960101