531-95-3 | (S)-3-(4-Hydroxyphenyl)chroman-7-ol

Packsize	Purity	Availability	Price	Discounted Price
1mg	≥98%	in stock	$27.00	$19.00
5mg	98%	in stock	$42.00	$30.00
25mg	98%	in stock	$68.00	$48.00
250mg	97%	in stock	$88.00	$62.00
1g	97%	in stock	$248.00	$174.00

Description

• Catalog Number: AI51898
• Chemical Name: (S)-3-(4-Hydroxyphenyl)chroman-7-ol
• CAS Number: 531-95-3
• Molecular Formula: C15H14O3
• Molecular Weight: 242.2699
• MDL Number: MFCD00200962
• SMILES: Oc1ccc(cc1)[C@H]1COc2c(C1)ccc(c2)O

Computed Properties

• Complexity: 273
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Heavy Atom Count: 18
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 1
• XLogP3: 3

Literature

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

• Equol inhibits growth, induces atresia, and inhibits steroidogenesis of mouse antral follicles in vitro.

  Toxicology and applied pharmacology 20160315

• Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein.

  Toxicological sciences : an official journal of the Society of Toxicology 20150201

• The inhibitory effect of black soybean on hepatic cholesterol accumulation in high cholesterol and high fat diet-induced non-alcoholic fatty liver disease.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20131001

• Assessment of ABCG2-mediated transport of xenobiotics across the blood-milk barrier of dairy animals using a new MDCKII in vitro model.

  Archives of toxicology 20130901

• Estrogen receptor β (ERβ1) transactivation is differentially modulated by the transcriptional coregulator Tip60 in a cis-acting element-dependent manner.

  The Journal of biological chemistry 20130830

• Effects of the natural endocrine disruptor equol on the pituitary function in adult male rats.

  Toxicology 20130208

• Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities.

  Chemical research in toxicology 20121119

• Interaction effects between genes involved in the AKT signaling pathway and phytoestrogens in gastric carcinogenesis: a nested case-control study from the Korean Multi-Center Cancer Cohort.

  Molecular nutrition & food research 20121101

• Effect of 17β-estradiol and flavonoids on the regulation of expression of newly identified oestrogen responsive genes in a rat raphe nuclei-derived cell line.

  Journal of cellular physiology 20121001

• Epigenetic modulation of BRCA1 and BRCA2 gene expression by equol in breast cancer cell lines.

  The British journal of nutrition 20121001

• Endocrine disrupting chemicals in urine of Japanese male partners of subfertile couples: a pilot study on exposure and semen quality.

  International journal of hygiene and environmental health 20120901

• Analysis of regulatory mechanisms of an insulin-inducible SHARP-2 gene by (S)-Equol.

  Archives of biochemistry and biophysics 20120901

• Synergistic and Selective Cancer Cell Killing Mediated by the Oncolytic Adenoviral Mutant AdΔΔ and Dietary Phytochemicals in Prostate Cancer Models.

  Human gene therapy 20120901

• The effect of equol injection in ovo on lipid metabolism and hepatic lipogenic gene expression in broilers.

  Animal : an international journal of animal bioscience 20120901

• Dietary intakes and food sources of phytoestrogens in the European Prospective Investigation into Cancer and Nutrition (EPIC) 24-hour dietary recall cohort.

  European journal of clinical nutrition 20120801

• [Microbial conversion of daidzein affects fecal equol concentration and bacterial composition of rats with or without ovariectomy].

  Wei sheng wu xue bao = Acta microbiologica Sinica 20120704

• Photoimmune protective effect of the phytoestrogenic isoflavonoid equol is partially due to its antioxidant activities.

  Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20120701

• Foetal exposure to phthalate esters and anogenital distance in male newborns.

  International journal of andrology 20120601

• Equol production changes over time in postmenopausal women.

  The Journal of nutritional biochemistry 20120601

• Does equol production determine soy endocrine effects?

  European journal of nutrition 20120601

• Prostate cancer chemoprevention by soy isoflavones: role of intestinal bacteria as the 'second human genome'.

  Cancer science 20120601

• Elucidation of the metabolic pathway of S-equol in rat, monkey and man.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120601

• Editorial comment to involvement of estrogen receptors in prostatic diseases.

  International journal of urology : official journal of the Japanese Urological Association 20120601

• Toxicokinetics and lack of uterotropic effect of orally administered S-equol.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120501

• Equol production changes over time in pre-menopausal women.

  The British journal of nutrition 20120401

• 2-Morpholinoisoflav-3-enes as flexible intermediates in the synthesis of phenoxodiol, isophenoxodiol, equol and analogues: vasorelaxant properties, estrogen receptor binding and Rho/RhoA kinase pathway inhibition.

  Bioorganic & medicinal chemistry 20120401

• The effects of natural S-equol supplementation on skin aging in postmenopausal women: a pilot randomized placebo-controlled trial.

  Menopause (New York, N.Y.) 20120201

• Urinary estrogen metabolites during a randomized soy trial.

  Nutrition and cancer 20120201

• [Phytoestrogenes in menopause: working mechanisms and clinical results in 28 patients].

  Ceska gynekologie 20120201

• Prostate cancer chemoprevention study: an investigative randomized control study using purified isoflavones in men with rising prostate-specific antigen.

  Cancer science 20120101

• A natural S-equol supplement alleviates hot flushes and other menopausal symptoms in equol nonproducing postmenopausal Japanese women.

  Journal of women's health (2002) 20120101

• Biochemical investigation and gene analysis of equol: a plant and soy-derived isoflavonoid with antiaging and antioxidant properties with potential human skin applications.

  BioFactors (Oxford, England) 20120101

• The isoflavone metabolite 6-methoxyequol inhibits angiogenesis and suppresses tumor growth.

  Molecular cancer 20120101

• Comparative activities of the S-enantiomer and racemic forms of equol on bone fragility in ovariectomized mice.

  Bioscience, biotechnology, and biochemistry 20120101

• Experimentally induced mastitis and metritis modulate soy bean derived isoflavone biotransformation in diary cows.

  Theriogenology 20111201

• Suppression of dendritic cells' maturation and functions by daidzein, a phytoestrogen.

  Toxicology and applied pharmacology 20111201

• Antioxidant effect of a phytoestrogen equol on cultured muscle cells of embryonic broilers.

  In vitro cellular & developmental biology. Animal 20111201

• [Equol-producing phenotype and in relation to serum sex hormones among healthy adults in Beijing].

  Wei sheng yan jiu = Journal of hygiene research 20111101

• Resistant starch promotes equol production and inhibits tibial bone loss in ovariectomized mice treated with daidzein.

  Metabolism: clinical and experimental 20111001

• Apparent bioavailability of isoflavones in urinary excretions of postmenopausal Malay women consuming tempeh compared with milk.

  International journal of food sciences and nutrition 20110901

• Soy isoflavones augment the effect of TRAIL-mediated apoptotic death in prostate cancer cells.

  Oncology reports 20110901

• Anticancer mechanism of equol in 7,12-dimethylbenz(a)anthracene-treated animals.

  International journal of oncology 20110901

• Effects of S-equol and natural S-equol supplement (SE5-OH) on the growth of MCF-7 in vitro and as tumors implanted into ovariectomized athymic mice.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110901

• Emerging evidence of the health benefits of S-equol, an estrogen receptor β agonist.

  Nutrition reviews 20110801

• S-equol and the fermented soy product SE5-OH containing S-equol similarly decrease ovariectomy-induced increase in rat tail skin temperature in an animal model of hot flushes.

  Menopause (New York, N.Y.) 20110701

• Impact of perinatal exposure to equol enantiomers on reproductive development in rodents.

  Reproductive toxicology (Elmsford, N.Y.) 20110701

• The role of soy isoflavones in menopausal health: report of The North American Menopause Society/Wulf H. Utian Translational Science Symposium in Chicago, IL (October 2010).

  Menopause (New York, N.Y.) 20110701

• [Anti-invasion effects of R- and S-enantiomers of equol on prostate cancer PC3, DU145 cells].

  Wei sheng yan jiu = Journal of hygiene research 20110701

• O-desmethylangolensin: the importance of equol's lesser known cousin to human health.

  Advances in nutrition (Bethesda, Md.) 20110701

• [Effect of equol on breast tumors induced by 7, 12-dimethylbenz (α) anthracene in ovariectominzed rats].

  Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences 20110618

• Natural S-equol decreases bone resorption in postmenopausal, non-equol-producing Japanese women: a pilot randomized, placebo-controlled trial.

  Menopause (New York, N.Y.) 20110501

• Lactobacillus rhamnosus JCM 2771: impact on metabolism of isoflavonoids in the fecal flora from a male equol producer.

  Current microbiology 20110501

• Development of chiral liquid chromatography-tandem mass spectrometry isotope dilution methods for the determination of unconjugated and total S-equol in human plasma and urine.

  Journal of pharmaceutical and biomedical analysis 20110428

• Equol-stimulated mitochondrial reactive oxygen species activate endothelial nitric oxide synthase and redox signaling in endothelial cells: roles for F-actin and GPR30.

  Hypertension (Dallas, Tex. : 1979) 20110401

• Hippocampal responsiveness to 17β-estradiol and equol after long-term ovariectomy: implication for a therapeutic window of opportunity.

  Brain research 20110316

• Urinary isoflavone phytoestrogens in German children and adolescents--a longitudinal examination in the DONALD cohort.

  Molecular nutrition & food research 20110301

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

  Journal of agricultural and food chemistry 20110209

• Is equol production beneficial to health?

  The Proceedings of the Nutrition Society 20110201

• Single-dose and steady-state pharmacokinetic studies of S-equol, a potent nonhormonal, estrogen receptor β-agonist being developed for the treatment of menopausal symptoms.

  Menopause (New York, N.Y.) 20110201

• Transcriptional activity of estrogen-related receptor γ (ERRγ) is stimulated by the phytoestrogen equol.

  The Journal of steroid biochemistry and molecular biology 20110101

• Development of bioluminescent enzyme immunoassay for s-equol using firefly luciferase and its application to the assessment of equol-producer status.

  Chemical & pharmaceutical bulletin 20110101

• Equol an isoflavonoid: potential for improved prostate health, in vitro and in vivo evidence.

  Reproductive biology and endocrinology : RB&E 20110101

• Soy isoflavone equol perpetuates dextran sulfate sodium-induced acute colitis in mice.

  Bioscience, biotechnology, and biochemistry 20110101

• Neuromodulation by soy diets or equol: anti-depressive & anti-obesity-like influences, age- & hormone-dependent effects.

  BMC neuroscience 20110101

• [Equol induced apoptosis of human breast cancer MDA-MB-231 cell by inhibiting the expression of nuclear factor-kappaB].

  Wei sheng yan jiu = Journal of hygiene research 20110101

• Distribution of isoflavones in samples of serum, liver and mammary glands of rats or pigs fed dietary isoflavones.

  Annals of nutrition & metabolism 20110101

• Identification of two novel reductases involved in equol biosynthesis in Lactococcus strain 20-92.

  Journal of molecular microbiology and biotechnology 20110101

• Modulation of monoamine neurotransmitters in fighting fish Betta splendens exposed to waterborne phytoestrogens.

  Fish physiology and biochemistry 20101201

• Genotoxicity assessment of S-equol in bacterial mutation, chromosomal aberration, and rodent bone marrow micronucleus tests.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20101201

• Urinary phytoestrogens and risk of prostate cancer in Jamaican men.

  Cancer causes & control : CCC 20101201

• Rapid signaling actions of environmental estrogens in developing granule cell neurons are mediated by estrogen receptor ß.

  Endocrinology 20101201

• Mammary gland differentiation by early life exposure to enantiomers of the soy isoflavone metabolite equol.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20101101

• Effects of a high dose, aglycone-rich soy extract on prostate-specific antigen and serum isoflavone concentrations in men with localized prostate cancer.

  Nutrition and cancer 20101101

• [Research development on relation between equol and soy foods health effect].

  Wei sheng yan jiu = Journal of hygiene research 20101101

• [Advances on the study of equol metabolism in human].

  Wei sheng yan jiu = Journal of hygiene research 20101101

• Synthesis of isoflavone aglycones and equol in soy milks fermented by food-related lactic acid bacteria and their effect on human intestinal Caco-2 cells.

  Journal of agricultural and food chemistry 20101013

• Topical isoflavonoids reduce experimental cutaneous inflammation in mice.

  Immunology and cell biology 20101001

• Daidzein and the daidzein metabolite, equol, enhance adipocyte differentiation and PPARgamma transcriptional activity.

  The Journal of nutritional biochemistry 20100901

• Dietary genistein and equol (4', 7 isoflavandiol) reduce oxidative stress and protect rats against focal cerebral ischemia.

  American journal of physiology. Regulatory, integrative and comparative physiology 20100901

• Slackia equolifaciens sp. nov., a human intestinal bacterium capable of producing equol.

  International journal of systematic and evolutionary microbiology 20100801

• Assessment of a robust model protocol with accelerated throughput for a human recombinant full length estrogen receptor-alpha binding assay: protocol optimization and intralaboratory assay performance as initial steps towards validation.

  Reproductive toxicology (Elmsford, N.Y.) 20100801

• The assessment of estrogenic or anti-estrogenic activity of chemicals by the human stably transfected estrogen sensitive MELN cell line: results of test performance and transferability.

  Reproductive toxicology (Elmsford, N.Y.) 20100801

• Optimization and prevalidation of the in vitro ERalpha CALUX method to test estrogenic and antiestrogenic activity of compounds.

  Reproductive toxicology (Elmsford, N.Y.) 20100801

• Conversion of (3S,4R)-tetrahydrodaidzein to (3S)-equol by THD reductase: proposed mechanism involving a radical intermediate.

  Biochemistry 20100706

• Daidzein-metabolising phenotypes in relation to serum lipids and uric acid in adults in Guangzhou, China.

  The British journal of nutrition 20100701

• Effects of genistein and equol on human and rat testicular 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase 3 activities.

  Asian journal of andrology 20100701

• Effects of isoflavones equol and genistein on bone quality in a rat osteopenia model.

  Phytotherapy research : PTR 20100601

• Microbial equol production attenuates colonic methanogenesis and sulphidogenesis in vitro.

  Anaerobe 20100601

• Delayed activation of extracellular-signal-regulated kinase 1/2 is involved in genistein- and equol-induced cell proliferation and estrogen-receptor-alpha-mediated transcription in MCF-7 breast cancer cells.

  The Journal of nutritional biochemistry 20100501

• Evaluation of bone quality and quantity in osteoporotic mice--the effects of genistein and equol.

  Phytomedicine : international journal of phytotherapy and phytopharmacology 20100501

• The chemopreventive action of equol enantiomers in a chemically induced animal model of breast cancer.

  Carcinogenesis 20100501

• Isolation and characterization of the equol-producing bacterium Slackia sp. strain NATTS.

  Archives of microbiology 20100401

• Comparative effects of R- and S-equol and implication of transactivation functions (AF-1 and AF-2) in estrogen receptor-induced transcriptional activity.

  Nutrients 20100301

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

  Toxicology letters 20100215

• Changes in the histomorphometric and biomechanical properties of the proximal femur of ovariectomized rat after treatment with the phytoestrogens genistein and equol.

  Planta medica 20100201

• Comparison of urodynamic effects of phytoestrogens equol, puerarin and genistein with these of estradiol 17beta in ovariectomized rats.

  Experimental gerontology 20100201

• The soy isoflavone equol enhances antigen-specific IgE production in ovalbumin-immunized BALB/c mice.

  Journal of nutritional science and vitaminology 20100101

• [Prevalence of equol producer phenotype and its relations to lifestyle factors and dietary intakes among lifestyle factors and dietary intakes among healthy Chinese adults in Beijing].

  Wei sheng yan jiu = Journal of hygiene research 20100101

• Prevalence of the equol-producer phenotype and its relationship with dietary isoflavone and serum lipids in healthy Chinese adults.

  Journal of epidemiology 20100101

• GC-MS determined distribution of urinary equol producers as affected by age, gender, and repeated ingestions of soymilk.

  Journal of food science 20100101

• The role of diet in the metabolism of daidzein by human faecal microbiota sampled from Italian volunteers.

  The Journal of nutritional biochemistry 20091201

• Equol in milk of dairy cows is derived from forage legumes such as red clover.

  The British journal of nutrition 20091201

• Dietary cholesterol lowers plasma and cecal equol concentrations in mice.

  Nutrition research (New York, N.Y.) 20091201

• [Nutrition and bone health. Isoflavones in bone health].

  Clinical calcium 20091001

• Transport and metabolism of equol by Caco-2 human intestinal cells.

  Journal of agricultural and food chemistry 20090923

• Isoflavone supplements stimulated the production of serum equol and decreased the serum dihydrotestosterone levels in healthy male volunteers.

  Prostate cancer and prostatic diseases 20090901

• Daidzein-metabolizing phenotypes in relation to mammographic breast density among premenopausal women in the United States.

  Breast cancer research and treatment 20090801

• Chronic equol administration attenuates the antioxidant defense system and causes apoptosis in the mouse brain.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20090801

• Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay.

  Cancer epidemiology 20090701

• Association between estrogen receptor alpha polymorphisms and equol production, and its relation to bone mass.

  International journal of molecular medicine 20090601

• Biotransformation of daidzein to equol by crude enzyme from Asaccharobacter celatus AHU1763 required an anaerobic environment.

  Bioscience, biotechnology, and biochemistry 20090601

• Effects of equol on oxidized low-density lipoprotein-induced apoptosis in endothelial cells.

  Journal of atherosclerosis and thrombosis 20090601

• Prostatic soy isoflavone concentrations exceed serum levels after dietary supplementation.

  The Prostate 20090515

• Respective contribution exerted by AF-1 and AF-2 transactivation functions in estrogen receptor alpha induced transcriptional activity by isoflavones and equol: consequence on breast cancer cell proliferation.

  Molecular nutrition & food research 20090501

• Ileal and faecal digestibility of daidzein and genistein and plasma bioavailability of these isoflavones and their bioactive metabolites in the ovariectomised rat.

  Molecular nutrition & food research 20090501

• Hepatoprotective effects of daidzein against 7,12-dimetylbenz[a]anthracene-induced oxidative stress in mice.

  International journal of molecular medicine 20090501

• Effect of glycosidation of isoflavones on their bioavailability and pharmacokinetics in aged male rats.

  Molecular nutrition & food research 20090501

• Equol but not genistein improves early metaphyseal fracture healing in osteoporotic rats.

  Planta medica 20090401

• Equol is more active than soy isoflavone itself to compete for binding to thromboxane A(2) receptor in human platelets.

  Thrombosis research 20090301

• Systemic administration of diarylpropionitrile (DPN) or phytoestrogens does not affect anxiety-related behaviors in gonadally intact male rats.

  Hormones and behavior 20090201

• Equol induces apoptosis through cytochrome c-mediated caspases cascade in human breast cancer MDA-MB-453 cells.

  Chemico-biological interactions 20090115

• Modulation of neurotoxicant-induced increases in intracellular calcium by phytoestrogens differ for amyloid beta peptide (Abeta) and 1-methyl-4-phenyl-pyridine (MPP(+)).

  Journal of applied toxicology : JAT 20090101

• A preliminary study of the safety, feasibility and cognitive efficacy of soy isoflavone supplements in older men and women.

  Age and ageing 20090101

• New equol supplement for relieving menopausal symptoms: randomized, placebo-controlled trial of Japanese women.

  Menopause (New York, N.Y.) 20090101

• [Effect of equol of a isoflavone metabolite on menopausal symptoms].

  Wei sheng yan jiu = Journal of hygiene research 20090101

• Daidzein-metabolizing phenotypes in relation to serum hormones and sex hormone binding globulin, and urinary estrogen metabolites in premenopausal women in the United States.

  Cancer causes & control : CCC 20081201

• Effects of prior oral contraceptive use and soy isoflavonoids on estrogen-metabolizing cytochrome P450 enzymes.

  The Journal of steroid biochemistry and molecular biology 20081201

• Receptor binding and transactivation activities of red clover isoflavones and their metabolites.

  The Journal of steroid biochemistry and molecular biology 20081101

• Antioxidant effects of equol on bovine aortic endothelial cells.

  Biochemical and biophysical research communications 20081024

• Concentrations of isoflavones and their metabolites in the blood of pregnant and non-pregnant heifers fed soy bean.

  The Journal of reproduction and development 20081001

• Impact of soy supplementation on sex steroids and vascular inflammation markers in postmenopausal women using tibolone: role of equol production capability.

  Climacteric : the journal of the International Menopause Society 20081001

• Isolation and characterization of a novel equol-producing bacterium from human feces.

  Bioscience, biotechnology, and biochemistry 20081001

• Urinary isoflavonoid excretion is similar after consuming soya milk and miso soup in Japanese-American women.

  The British journal of nutrition 20080801

• Acute and subchronic toxicity and genotoxicity of SE5-OH, an equol-rich product produced by Lactococcus garvieae.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080801

• Comparative activities of daidzein metabolites, equol and O-desmethylangolensin, on bone mineral density and lipid metabolism in ovariectomized mice and in osteoclast cell cultures.

  European journal of nutrition 20080801

• Biotransformation of C-glucosylisoflavone puerarin to estrogenic (3S)-equol in co-culture of two human intestinal bacteria.

  Biological & pharmaceutical bulletin 20080801

• Effect of intestinal production of equol on menopausal symptoms in women treated with soy isoflavones.

  International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics 20080701

• Effect of sulphation on the oestrogen agonist activity of the phytoestrogens genistein and daidzein in MCF-7 human breast cancer cells.

  The Journal of endocrinology 20080601

• Equol production capability is associated with favorable vascular function in postmenopausal women using tibolone; no effect with soy supplementation.

  Atherosclerosis 20080501

• Isolation and identification of equol-producing bacterial strains from cultures of pig faeces.

  FEMS microbiology letters 20080501

• Adlercreutzia equolifaciens gen. nov., sp. nov., an equol-producing bacterium isolated from human faeces, and emended description of the genus Eggerthella.

  International journal of systematic and evolutionary microbiology 20080501

• Neonatal exposure to endocrine active compounds or an ERbeta agonist increases adult anxiety and aggression in gonadally intact male rats.

  Hormones and behavior 20080401

• Topical isoflavones provide effective photoprotection to skin.

  Photodermatology, photoimmunology & photomedicine 20080401

• Inhibition by soya isoflavones of human polymorphonuclear leukocyte function: possible relevance for the beneficial effects of soya intake.

  The British journal of nutrition 20080201

• Effects of dietary equol administration on the mammary gland in ovariectomized Sprague-Dawley rats.

  Menopause (New York, N.Y.) 20080101

• Age-stratified serum levels of isoflavones and proportion of equol producers in Japanese and Korean healthy men.

  Prostate cancer and prostatic diseases 20080101

• Equol status modifies the association of soy intake and mammographic density in a sample of postmenopausal women.

  Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080101

• Dietary and lifestyle correlates of urinary excretion status of equol in Japanese women.

  Nutrition and cancer 20080101

• Effects of a high daily dose of soy isoflavones on DNA damage, apoptosis, and estrogenic outcomes in healthy postmenopausal women: a phase I clinical trial.

  Menopause (New York, N.Y.) 20080101

• Phase II trial of isoflavone in prostate-specific antigen recurrent prostate cancer after previous local therapy.

  BMC cancer 20080101

• Individual differences in equol production capability modulate blood pressure in tibolone-treated postmenopausal women: lack of effect of soy supplementation.

  Climacteric : the journal of the International Menopause Society 20071201

• Effects of dietary equol administration on ovariectomy induced bone loss in Sprague-Dawley rats.

  Maturitas 20071120

• Equol, a metabolite of the soybean isoflavone daidzein, inhibits neoplastic cell transformation by targeting the MEK/ERK/p90RSK/activator protein-1 pathway.

  The Journal of biological chemistry 20071109

• Isoflavonoid-based bone-sparing treatments exert a low activity on reproductive organs and on hepatic metabolism of estradiol in ovariectomized rats.

  Toxicology and applied pharmacology 20071015

• Uterotropic effects of dietary equol administration in ovariectomized Sprague-Dawley rats.

  Climacteric : the journal of the International Menopause Society 20071001

• Role of tyrosine phosphorylation in U46619-induced vasoconstriction of pulmonary vasculature and its modulation by genistein, daidzein, and equol.

  Journal of cardiovascular pharmacology 20071001

• Soy and prostate cancer study results mixed.

  Journal of the National Cancer Institute 20070919

• Chemical composition and biological activity of a new type of Brazilian propolis: red propolis.

  Journal of ethnopharmacology 20070905

• Aza analogues of equol: novel ligands for estrogen receptor beta.

  Bioorganic & medicinal chemistry 20070901

• Phyto-oestrogens and risk of prostate cancer in Scottish men.

  The British journal of nutrition 20070801

• High levels of equol in organic skimmed Finnish cow milk.

  Molecular nutrition & food research 20070701

• Bioavailability of soy isoflavones in rats Part I: application of accurate methodology for studying the effects of gender and source of isoflavones.

  Molecular nutrition & food research 20070701

• Metabolism of dietary soy isoflavones to equol by human intestinal microflora--implications for health.

  Molecular nutrition & food research 20070701

• Simultaneous determination of daidzein, equol, genistein and bisphenol A in human urine by a fast and simple method using SPE and GC-MS.

  Molecular nutrition & food research 20070701

• Dietary isoflavones differentially induce gene expression changes in lymphocytes from postmenopausal women who form equol as compared with those who do not.

  The Journal of nutritional biochemistry 20070601

• Does the effect of soy phytoestrogens on bone in postmenopausal women depend on the equol-producing phenotype?

  Nutrition reviews 20070601

• Modulation of soy isoflavones bioavailability and subsequent effects on bone health in ovariectomized rats: the case for equol.

  Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20070501

• Vasorelaxant and antioxidant activity of the isoflavone metabolite equol in carotid and cerebral arteries.

  Brain research 20070413

• Monoclonal antibody-based time-resolved fluorescence immunoassays for daidzein, genistein, and equol in blood and urine: application to the Isoheart intervention study.

  Clinical chemistry 20070401

• Equol inhibits nitric oxide production and inducible nitric oxide synthase gene expression through down-regulating the activation of Akt.

  International immunopharmacology 20070401

• Effects of dietary equol on the pituitary of the ovariectomized rats.

  Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20070401

• Bioavailability and urinary excretion of isoflavones in humans: effects of soy-based supplements formulation and equol production.

  Journal of pharmaceutical and biomedical analysis 20070312

• Urinary excretion of equol by postmenopausal women consuming soymilk fermented by probiotic bifidobacteria.

  European journal of clinical nutrition 20070301

• Urinary isoflavonoid excretion and soy consumption in three generations of Japanese women in Hawaii.

  European journal of clinical nutrition 20070201

• Production of phytoestrogen S-equol from daidzein in mixed culture of two anaerobic bacteria.

  Archives of microbiology 20070201

• Rapid and convenient detection of urinary equol by thin-layer chromatography.

  Journal of nutritional science and vitaminology 20070201

• Equol producer status, salivary estradiol profile and urinary excretion of isoflavones in Irish Caucasian women, following ingestion of soymilk.

  Steroids 20070101

• Effects of dietary equol on body weight gain, intra-abdominal fat accumulation, plasma lipids, and glucose tolerance in ovariectomized Sprague-Dawley rats.

  Menopause (New York, N.Y.) 20070101

• Possible role of equol status in the effects of isoflavone on bone and fat mass in postmenopausal Japanese women: a double-blind, randomized, controlled trial.

  Menopause (New York, N.Y.) 20070101

• The effect of the phytoestrogens genistein, daidzein, and equol on the growth of tamoxifen-resistant T47D/PKC alpha.

  Nutrition and cancer 20070101

• Isoflavones, equol and cardiovascular disease: pharmacological and therapeutic insights.

  Current medicinal chemistry 20070101

• Behavioral changes in fish exposed to phytoestrogens.

  Environmental pollution (Barking, Essex : 1987) 20061201

• Molecular signatures of soy-derived phytochemicals in androgen-responsive prostate cancer cells: a comparison study using DNA microarray.

  Molecular carcinogenesis 20061201

• Phyto- and endogenous estrogens differently activate intracellular calcium ion mobilization in bovine endometrial cells.

  The Journal of reproduction and development 20061201

• Total synthesis of (S)-equol.

  Organic letters 20061123

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

  Journal of molecular graphics & modelling 20061101

• Isoflavone metabolites and their in vitro dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration.

  The Journal of steroid biochemistry and molecular biology 20061101

• Associations among maternal soy intake, isoflavone levels in urine and blood samples, and maternal and umbilical hormone concentrations (Japan).

  Cancer causes & control : CCC 20061101

• Phytoestrogens regulate transcription and translation of vitamin D receptor in colon cancer cells.

  The Journal of endocrinology 20061101

• Consumption of Lactobacillus acidophilus and Bifidobacterium longum does not alter phytoestrogen metabolism and plasma hormones in men: a pilot study.

  Journal of alternative and complementary medicine (New York, N.Y.) 20061101

• [Progress in research of equol: a metabolite of the isoflavone daidzein].

  Sheng li ke xue jin zhan [Progress in physiology] 20061001

• The isoflavone Equol mediates rapid vascular relaxation: Ca2+-independent activation of endothelial nitric-oxide synthase/Hsp90 involving ERK1/2 and Akt phosphorylation in human endothelial cells.

  The Journal of biological chemistry 20060915

• One-month exposure to soy isoflavones did not induce the ability to produce equol in postmenopausal women.

  European journal of clinical nutrition 20060901

• Effects of high-dose soy isoflavones and equol on reproductive tissues in female cynomolgus monkeys.

  Biology of reproduction 20060901

• Protective effect of the isoflavone equol against DNA damage induced by ultraviolet radiation to hairless mouse skin.

  Journal of veterinary science 20060901

• Reduced isoflavone metabolites formed by the human gut microflora suppress growth but do not affect DNA integrity of human prostate cancer cells.

  The British journal of nutrition 20060901

• Supplementation of difructose anhydride III enhanced elevation of plasma equol concentrations and lowered plasma total cholesterol in isoflavone-fed rats.

  The British journal of nutrition 20060901

• Production of equol from daidzein by gram-positive rod-shaped bacterium isolated from rat intestine.

  Journal of bioscience and bioengineering 20060901

• The prooxidant, rather than antioxidant, acts of daidzein in vivo and in vitro: daidzein suppresses glutathione metabolism.

  European journal of pharmacology 20060807

• Soya isoflavones suppress phorbol 12-myristate 13-acetate-induced COX-2 expression in MCF-7 cells.

  The British journal of nutrition 20060701

• Dietary modulation of p-nonylphenol-induced polycystic kidneys in male Sprague-Dawley rats.

  Toxicological sciences : an official journal of the Society of Toxicology 20060601

• Validation and application of a robust yeast estrogen bioassay for the screening of estrogenic activity in animal feed.

  Food additives and contaminants 20060601

• Identification of equol producers in a Japanese population by high-performance liquid chromatography with coulometric array for determining serum isoflavones.

  Phytomedicine : international journal of phytotherapy and phytopharmacology 20060501

• Equol and para-ethyl-phenol stimulate prostaglandin F(2alpha) secretion in bovine corpus luteum: intracellular mechanisms of action.

  Prostaglandins & other lipid mediators 20060501

• Antioxidant activity of isoflavones and their major metabolites using different in vitro assays.

  Journal of agricultural and food chemistry 20060419

• Absorption of isoflavones in humans: effects of food matrix and processing.

  The Journal of nutritional biochemistry 20060401

• Effects of dietary daidzein and its metabolite, equol, at physiological concentrations on the growth of estrogen-dependent human breast cancer (MCF-7) tumors implanted in ovariectomized athymic mice.

  Carcinogenesis 20060401

• Cooperative effects of isoflavones and exercise on bone and lipid metabolism in postmenopausal Japanese women: a randomized placebo-controlled trial.

  Metabolism: clinical and experimental 20060401

• Effects of phytoestrogens on testosterone secretion by Leydig cells from Biłgoraj ganders (Anser anser).

  British poultry science 20060401

• Short-term phytoestrogen supplementation alters insulin-like growth factor profile but not lipid or antioxidant status.

  The Journal of nutritional biochemistry 20060301

• Postmenopausal bone mineral density in relation to soy isoflavone-metabolizing phenotypes.

  Maturitas 20060220

• Phytoestrogens and their metabolites inhibit the sensitivity of the bovine corpus luteum to luteotropic factors.

  The Journal of reproduction and development 20060201

• Does genotype and equol-production status affect response to isoflavones? Data from a pan-European study on the effects of isoflavones on cardiovascular risk markers in post-menopausal women.

  The Proceedings of the Nutrition Society 20060201

• Structural elucidation of hydroxylated metabolites of the isoflavan equol by gas chromatography-mass spectrometry and high-performance liquid chromatography-mass spectrometry.

  Drug metabolism and disposition: the biological fate of chemicals 20060101

• Phyto-oestrogen intake in Scottish men: use of serum to validate a self-administered food-frequency questionnaire in older men.

  European journal of clinical nutrition 20060101

• Isoflavonoid photoprotection in mouse and human skin is dependent on metallothionein.

  The Journal of investigative dermatology 20060101

• Serum cholesterol efflux potential in postmenopausal women treated with isolated isoflavones.

  Menopause (New York, N.Y.) 20060101

• Genistein and 17beta-estradiol, but not equol, regulate vitamin D synthesis in human colon and breast cancer cells.

  Anticancer research 20060101

• Equol: a comparison of the effects of the racemic compound with that of the purified S-enantiomer on the growth, invasion, and DNA integrity of breast and prostate cells in vitro.

  Nutrition and cancer 20060101

• Detection of isoflavones in mouse tibia after feeding daidzein.

  Journal of medicinal food 20060101

• Phytoestrogen action in Leydig cells of Biłgoraj ganders (Anser anser).

  Reproductive biology 20060101

• Estrogen receptor-independent inhibition of tumor necrosis factor-alpha gene expression by phytoestrogen equol is mediated by blocking nuclear factor-kappaB activation in mouse macrophages.

  Biochemical pharmacology 20051219

• Serum equol, bone mineral density and biomechanical bone strength differ among four mouse strains.

  The Journal of nutritional biochemistry 20051201

• Soy-isoflavone-enriched foods and inflammatory biomarkers of cardiovascular disease risk in postmenopausal women: interactions with genotype and equol production.

  The American journal of clinical nutrition 20051201

• High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart.

  The British journal of nutrition 20051201

• Effect of pure genistein on bone markers and hot flushes.

  Climacteric : the journal of the International Menopause Society 20051201

• Sensitive high-performance liquid chromatographic method using coulometric electrode array detection for measurement of phytoestrogens in dried blood spots.

  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20051105

• Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.

  Journal of medicinal chemistry 20050908

• Formononetin, a phyto-oestrogen, and its metabolites up-regulate interleukin-4 production in activated T cells via increased AP-1 DNA binding activity.

  Immunology 20050901

• Phytoestrogens induce differential estrogen receptor alpha- or Beta-mediated responses in transfected breast cancer cells.

  Experimental biology and medicine (Maywood, N.J.) 20050901

• Estrogenic and genotoxic potential of equol and two hydroxylated metabolites of Daidzein in cultured human Ishikawa cells.

  Toxicology letters 20050728

• X-ray single-crystal analysis of (-)-(S)-equol isolated from rat's feces.

  Chemistry & biodiversity 20050701

• Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells.

  The Journal of steroid biochemistry and molecular biology 20050401

• Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health.

  Experimental biology and medicine (Maywood, N.J.) 20050301

• Isolation and characterisation of an equol-producing mixed microbial culture from a human faecal sample and its activity under gastrointestinal conditions.

  Archives of microbiology 20050101

• Effect of a soymilk supplement containing isoflavones on urinary F2 isoprostane levels in premenopausal women.

  Nutrition and cancer 20050101

• Protection against photoaging in the hairless mouse by the isoflavone equol.

  Photochemistry and photobiology 20050101

• Consumption of Lactobacillus acidophilus and Bifidobacterium longum do not alter urinary equol excretion and plasma reproductive hormones in premenopausal women.

  European journal of clinical nutrition 20041201

• Lactobacillus gasseri: effects on mouse intestinal flora enzyme activity and isoflavonoids in the caecum and plasma.

  The British journal of nutrition 20041101

• Biotransformation of soy isoflavone-glycosides in laying hens: intestinal absorption and preferential accumulation into egg yolk of equol, a more estrogenic metabolite of daidzein.

  Biochimica et biophysica acta 20040924

• Estrogenicity of the isoflavone metabolite equol on reproductive and non-reproductive organs in mice.

  Biology of reproduction 20040901

• Synthesis of phytoestrogenic isoflavonoid disulfates.

  Steroids 20040901

• Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells.

  Toxicological sciences : an official journal of the Society of Toxicology 20040701

• Mammographic density in relation to daidzein-metabolizing phenotypes in overweight, postmenopausal women.

  Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20040701

• Identification of puerarin and its metabolites in rats by liquid chromatography-tandem mass spectrometry.

  Journal of agricultural and food chemistry 20040616

• Genotoxicity of the isoflavones genistein, daidzein and equol in V79 cells.

  Toxicology letters 20040615

• Distribution of soy-derived phytoestrogens in human breast tissue and biological fluids.

  Obstetrics and gynecology 20040501

• Isoflavones stimulate estrogen receptor-mediated core histone acetylation.

  Biochemical and biophysical research communications 20040423

• Equol is a novel anti-androgen that inhibits prostate growth and hormone feedback.

  Biology of reproduction 20040401

• Urinary isoflavone kinetics: the effect of age, gender, food matrix and chemical composition.

  The British journal of nutrition 20040401

• Influence of soya-based infant formula consumption on isoflavone and gut microflora metabolite concentrations in urine and on faecal microflora composition and metabolic activity in infants and children.

  The British journal of nutrition 20040401

• Serum steroid hormones, sex hormone-binding globulin concentrations, and urinary hydroxylated estrogen metabolites in post-menopausal women in relation to daidzein-metabolizing phenotypes.

  The Journal of steroid biochemistry and molecular biology 20040401

• Equol, a natural estrogenic metabolite from soy isoflavones: convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta.

  Bioorganic & medicinal chemistry 20040315

• Comparisons of percent equol producers between prostate cancer patients and controls: case-controlled studies of isoflavones in Japanese, Korean and American residents.

  Japanese journal of clinical oncology 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

• The topical isoflavonoid NV-07alpha reduces solar-simulated UV-induced suppression of Mantoux reactions in humans.

  Photochemistry and photobiology 20040101

• Measurement of isoflavones using liquid chromatography with multi-channel coulometric electrochemical detection.

  BioFactors (Oxford, England) 20040101

• Oestrogenic compounds and oxidative stress (in human sperm and lymphocytes in the Comet assay).

  Mutation research 20031101

• A toxicity identification evaluation approach to studying estrogenic substances in hog manure and agricultural runoff.

  Environmental toxicology and chemistry 20031001

• Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.

  Chemical research in toxicology 20031001

• Variations in metabolism of the soy isoflavonoid daidzein by human intestinal microfloras from different individuals.

  Archives of microbiology 20030701

• Effects of the isoflavones genistein and equol on the gonadal development of Japanese medaka Oryzias latipes.

  Environmental health perspectives 20030701

• Urinary equol excretion in relation to 2-hydroxyestrone and 16alpha-hydroxyestrone concentrations: an observational study of young to middle-aged women.

  The Journal of steroid biochemistry and molecular biology 20030701

• The phytoestrogen equol increases nitric oxide availability by inhibiting superoxide production: an antioxidant mechanism for cell-mediated LDL modification.

  Free radical biology & medicine 20030515

• Metabolism of isoflavones and lignans by the gut microflora: a study in germ-free and human flora associated rats.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030501

• Quantification of isoflavones and lignans in urine using gas chromatography/mass spectrometry.

  Analytical biochemistry 20030401

• Time-resolved fluoroimmunoassay for equol in plasma and urine.

  The Journal of steroid biochemistry and molecular biology 20030401

• Soy-derived isoflavones exert opposing actions on Guinea pig ventricular myocytes.

  The Journal of pharmacology and experimental therapeutics 20030301

• Soy isoflavonoid equol modulates the growth of benign and malignant prostatic epithelial cells in vitro.

  The Prostate 20030101

• Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry.

  Rapid communications in mass spectrometry : RCM 20030101

• Effect of in utero-administered coumestrol, equol, and organic selenium on biomarkers for phase 2 enzyme capacity and redox status.

  Nutrition and cancer 20030101

• Higher consumption of green tea may enhance equol production.

  Asian Pacific journal of cancer prevention : APJCP 20030101

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

  Bioscience, biotechnology, and biochemistry 20020701

• Quantitative analysis of urinary daidzein and equol by gas chromatography after solid-phase extraction and high-performance liquid chromatography.

  The International journal of biological markers 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

• Animal models impacted by phytoestrogens in commercial chow: implications for pathways influenced by hormones.

  Laboratory investigation; a journal of technical methods and pathology 20010501

• Effect of phytoestrogen and antioxidant supplementation on oxidative DNA damage assessed using the comet assay.

  Mutation research 20010307

• Assaying the estrogenicity of phytoestrogens in cells of different estrogen sensitive tissues.

  Toxicology in vitro : an international journal published in association with BIBRA 20010101