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Enterolactone

CAS No.:
78473-71-9
Catalog Number:
AG01CC6A
Molecular Formula:
Molecular Weight:
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$96
- +
5mg
≥95%
1 week
United States
$232
- +
10mg
≥95%
1 week
United States
$368
- +
50mg
≥95%
1 week
United States
$1418
- +
Product Description
Catalog Number:
AG01CC6A
Chemical Name:
Enterolactone
CAS Number:
78473-71-9
MDL Number:
MFCD01861506
IUPAC Name:
(3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
InChI:
InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m0/s1
InChI Key:
HVDGDHBAMCBBLR-WMLDXEAASA-N
Properties
Complexity:
383  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
298.121g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
298.338g/mol
Monoisotopic Mass:
298.121g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
66.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.3  
Literature
Title Journal
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
Mammary gene expression and activity of antioxidant enzymes and concentration of the mammalian lignan enterolactone in milk and plasma of dairy cows fed flax lignans and infused with flax oil in the abomasum. The British journal of nutrition 20121028
Tissue distribution and cytochrome P450 inhibition of sesaminol and its tetrahydrofuranoid metabolites. Journal of agricultural and food chemistry 20120905
Effects of feeding dairy cows different legume-grass silages on milk phytoestrogen concentration. Journal of dairy science 20120801
Identification and quantification of concentration-dependent biomarkers in MCF-7/BOS cells exposed to 17β-estradiol by 2-D DIGE and label-free proteomics. Journal of proteomics 20120719
Identification of enterodiol as a masker for caffeine bitterness by using a pharmacophore model based on structural analogues of homoeriodictyol. Journal of agricultural and food chemistry 20120627
Antiproliferative activity of lignans against the breast carcinoma cell lines MCF 7 and BT 20. Archives of gynecology and obstetrics 20120401
Serum enterolactone levels and mortality outcome in women with early breast cancer: a retrospective cohort study. Breast cancer research and treatment 20120401
Serum enterolactone and postmenopausal breast cancer risk by estrogen, progesterone and herceptin 2 receptor status. International journal of cancer 20120315
Lignan transformation by gut bacteria lowers tumor burden in a gnotobiotic rat model of breast cancer. Carcinogenesis 20120101
Phytoestrogen biomonitoring: an extractionless LC-MS/MS method for measuring urinary isoflavones and lignans by use of atmospheric pressure photoionization (APPI). Analytical and bioanalytical chemistry 20120101
Comparative effects of sesame seed lignan and flaxseed lignan in reducing the growth of human breast tumors (MCF-7) at high levels of circulating estrogen in athymic mice. Nutrition and cancer 20120101
Genetic susceptibility on CagA-interacting molecules and gene-environment interaction with phytoestrogens: a putative risk factor for gastric cancer. PloS one 20120101
Correlations of urinary phytoestrogen excretion with lifestyle factors and dietary intakes among middle-aged and elderly Chinese women. International journal of molecular epidemiology and genetics 20120101
Antiproliferative and anti-invasive effect of piceatannol, a polyphenol present in grapes and wine, against hepatoma AH109A cells. Journal of biomedicine & biotechnology 20120101
The association between dietary lignans, phytoestrogen-rich foods, and fiber intake and postmenopausal breast cancer risk: a German case-control study. Nutrition and cancer 20120101
In vitro anti-metastatic activity of enterolactone, a mammalian lignan derived from flax lignan, and down-regulation of matrix metalloproteinases in MCF-7 and MDA MB 231 cell lines. Indian journal of cancer 20120101
Plant polyphenols in prevention of heart disease. Bratislavske lekarske listy 20120101
Estimated enterolignans, lignan-rich foods, and fibre in relation to survival after postmenopausal breast cancer. British journal of cancer 20111011
Role of bifidobacteria in the activation of the lignan secoisolariciresinol diglucoside. Applied microbiology and biotechnology 20111001
Association between dietary phyto-oestrogens and bone density in men and postmenopausal women. The British journal of nutrition 20111001
Flaxseed and breast cancer: what should we tell our patients? Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20111001
Serum enterolactone and prognosis of postmenopausal breast cancer. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20111001
Presence of caffeic acid in flaxseed lignan macromolecule. Plant foods for human nutrition (Dordrecht, Netherlands) 20110901
Prediagnostic plasma enterolactone levels and mortality among women with breast cancer. Breast cancer research and treatment 20110801
Intramolecular catalytic asymmetric carbon-hydrogen insertion reactions. Synthetic advantages in total synthesis in comparison with alternative approaches. Organic & biomolecular chemistry 20110607
Cardioprotective activity of flax lignan concentrate extracted from seeds of Linum usitatissimum in isoprenalin induced myocardial necrosis in rats. Interdisciplinary toxicology 20110601
Effect of combined lignan phytoestrogen and melatonin treatment on secretion of steroid hormones by adrenal carcinoma cells. American journal of veterinary research 20110501
Intestinal distribution and excretion of sesaminol and its tetrahydrofuranoid metabolites in rats. Journal of agricultural and food chemistry 20110413
Effect of flaxseed lignans added to milk or fed to cows on oxidative degradation of dairy beverages enriched with polyunsaturated fatty acids. The Journal of dairy research 20110201
Effects of a safflower tea supplement on antioxidative status and bone markers in postmenopausal women. Nutrition research and practice 20110201
Estrogenic activities of sesame lignans and their metabolites on human breast cancer cells. Journal of agricultural and food chemistry 20110112
Whole and fractionated yellow pea flours reduce fasting insulin and insulin resistance in hypercholesterolaemic and overweight human subjects. The British journal of nutrition 20110101
Tamoxifen, flaxseed, and the lignan enterolactone increase stroma- and cancer cell-derived IL-1Ra and decrease tumor angiogenesis in estrogen-dependent breast cancer. Cancer research 20110101
Flavonoid engineering of flax potentiate its biotechnological application. BMC biotechnology 20110101
Gene expression analysis of flax seed development. BMC plant biology 20110101
Coffee consumption modifies risk of estrogen-receptor negative breast cancer. Breast cancer research : BCR 20110101
Phytoestrogen biological actions on Mammalian reproductive system and cancer growth. Scientia pharmaceutica 20110101
Chemoprevention of prostate cancer with nutrients and supplements. Cancer management and research 20110101
Dietary flaxseed administered post thoracic radiation treatment improves survival and mitigates radiation-induced pneumonopathy in mice. BMC cancer 20110101
Phytoestrogen consumption from foods and supplements and epithelial ovarian cancer risk: a population-based case control study. BMC women's health 20110101
Estimated dietary phytoestrogen intake and major food sources among women during the year before pregnancy. Nutrition journal 20110101
Tamoxifen and flaxseed alter angiogenesis regulators in normal human breast tissue in vivo. PloS one 20110101
Estrogenic botanical supplements, health-related quality of life, fatigue, and hormone-related symptoms in breast cancer survivors: a HEAL study report. BMC complementary and alternative medicine 20110101
Changes in human fecal microbiota due to chemotherapy analyzed by TaqMan-PCR, 454 sequencing and PCR-DGGE fingerprinting. PloS one 20110101
Urinary phytoestrogens and risk of prostate cancer in Jamaican men. Cancer causes & control : CCC 20101201
Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucoside. Nutrition research (New York, N.Y.) 20101101
Estrogen-like effects of cadmium in vivo do not appear to be mediated via the classical estrogen receptor transcriptional pathway. Environmental health perspectives 20101001
Reduction in Ki-67 in benign breast tissue of high-risk women with the lignan secoisolariciresinol diglycoside. Cancer prevention research (Philadelphia, Pa.) 20101001
Dietary lignans: physiology and potential for cardiovascular disease risk reduction. Nutrition reviews 20101001
Enterolactone and breast cancer: methodological issues may contribute to conflicting results in observational studies. Nutrition research (New York, N.Y.) 20101001
Profiles of phytoestrogens in human urine from several Asian countries. Journal of agricultural and food chemistry 20100908
Estrogen-induced angiogenic factors derived from stromal and cancer cells are differently regulated by enterolactone and genistein in human breast cancer in vivo. International journal of cancer 20100801
Investigation of relationships between urinary biomarkers of phytoestrogens, phthalates, and phenols and pubertal stages in girls. Environmental health perspectives 20100701
Enterodiol and enterolactone modulate the immune response by acting on nuclear factor-kappaB (NF-kappaB) signaling. Journal of agricultural and food chemistry 20100609
Bacterial transformation of dietary lignans in gnotobiotic rats. FEMS microbiology ecology 20100601
Effects of components present in flaxseed on human colon adenocarcinoma Caco-2 cells: Possible mechanisms of flaxseed on colon cancer development in animals. Drug discoveries & therapeutics 20100601
Development of a high-throughput LC/APCI-MS method for the determination of thirteen phytoestrogens including gut microbial metabolites in human urine and serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100415
Simultaneous determination of 11 phytoestrogens in human serum using a 2 min liquid chromatography/tandem mass spectrometry method. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100415
Comparison of murine and human estrogen sulfotransferase inhibition in vitro and in silico--implications for differences in activity, subunit dimerization and substrate inhibition. Molecular and cellular endocrinology 20100412
Health effects with consumption of the flax lignan secoisolariciresinol diglucoside. The British journal of nutrition 20100401
Reproducibility of plasma and urine biomarkers among premenopausal and postmenopausal women from the Nurses' Health Studies. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20100401
Dietary intake and urinary excretion of lignans in Finnish men. The British journal of nutrition 20100301
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
Chemopreventive actions by enterolactone and 13 VIOXX-related lactone derivatives in H295R human adrenocortical carcinoma cells. Toxicology letters 20100215
Breast, colorectal, and prostate cancer risk in the European Prospective Investigation into Cancer and Nutrition-Norfolk in relation to phytoestrogen intake derived from an improved database. The American journal of clinical nutrition 20100201
Assessment of information to substantiate a health claim on the prevention of prostate cancer by lignans. Nutrients 20100201
Plasma enterolactone and risk of colon and rectal cancer in a case-cohort study of Danish men and women. Cancer causes & control : CCC 20100101
Influence of lignans depletion on murine mammary gland morphology. Nutrition and cancer 20100101
Complementary roles in cancer prevention: protease inhibitor makes the cancer preventive peptide lunasin bioavailable. PloS one 20100101
Production of enterodiol from defatted flaxseeds through biotransformation by human intestinal bacteria. BMC microbiology 20100101
Dietary intake of fish, omega-3, omega-6 polyunsaturated fatty acids and vitamin D and the prevalence of psychotic-like symptoms in a cohort of 33,000 women from the general population. BMC psychiatry 20100101
The dietary isothiocyanate sulforaphane modulates gene expression and alternative gene splicing in a PTEN null preclinical murine model of prostate cancer. Molecular cancer 20100101
Human intestinal bacterium, strain END-2 is responsible for demethylation as well as lactonization during plant lignan metabolism. Biological & pharmaceutical bulletin 20100101
Flaxseed ingestion alters ratio of enterolactone enantiomers in human serum. Journal of nutrition and metabolism 20100101
Reference profile correlation reveals estrogen-like trancriptional activity of Curcumin. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20100101
Blood cell gene expression associated with cellular stress defense is modulated by antioxidant-rich food in a randomised controlled clinical trial of male smokers. BMC medicine 20100101
Effect of dietary intervention on serum lignan levels in pregnant women - a controlled trial. Reproductive health 20100101
Effects of a breast-health herbal formula supplement on estrogen metabolism in pre- and post-menopausal women not taking hormonal contraceptives or supplements: a randomized controlled trial. Breast cancer : basic and clinical research 20100101
Can rye intake decrease risk of human breast cancer? Food & nutrition research 20100101
Antiproliferative activity and induction of apoptosis in estrogen receptor-positive and negative human breast carcinoma cell lines by Gmelina asiatica roots. Pharmacognosy research 20100101
Sesame supplementation does not improve cardiovascular disease risk markers in overweight men and women. Nutrition, metabolism, and cardiovascular diseases : NMCD 20091201
Isoflavonoids - an overview of their biological activities and potential health benefits. Interdisciplinary toxicology 20091201
Weekly excretion of the mammalian lignan enterolactone in milk of dairy cows fed flaxseed meal. The Journal of dairy research 20091101
The interaction of monensin and flaxseed hulls on ruminal and milk concentration of the mammalian lignan enterolactone in late-lactating dairy cows. The Journal of dairy research 20091101
Asymmetric syntheses of (-)-enterolactone and (7'R)-7'-hydroxyenterolactone via organocatalyzed aldol reaction. The Journal of organic chemistry 20091016
Quantitative aspects of the metabolism of lignans in pigs fed fibre-enriched rye and wheat bread. The British journal of nutrition 20091001
Ruminal metabolism of flaxseed ( Linum usitatissimum) lignans to the mammalian lignan enterolactone and its concentration in ruminal fluid, plasma, urine and milk of dairy cows. The British journal of nutrition 20091001
Gastrointestinal microflora, food components and colon cancer prevention. The Journal of nutritional biochemistry 20091001
Concentration of the mammalian lignans enterolactone and enterodiol in milk of cows fed diets containing different concentrations of whole flaxseed. Animal : an international journal of animal bioscience 20091001
Complete genome sequence of Eggerthella lenta type strain (IPP VPI 0255). Standards in genomic sciences 20090929
Milk concentration of the mammalian lignan enterolactone, milk production, milk fatty acid profile, and digestibility in dairy cows fed diets containing whole flaxseed or flaxseed meal. The Journal of dairy research 20090801
Dietary sources of lignans and isoflavones modulate responses to estradiol in estrogen reporter mice. Molecular nutrition & food research 20090801
Occurrence of phytoestrogens in municipal wastewater and surface waters. Journal of environmental monitoring : JEM 20090801
Phyto-oestrogens in herbage and milk from cows grazing white clover, red clover, lucerne or chicory-rich pastures. Animal : an international journal of animal bioscience 20090801
Biotransformation of sesaminol triglucoside to mammalian lignans by intestinal microbiota. Journal of agricultural and food chemistry 20090722
Urinary phytoestrogen excretion and prostate cancer risk: a nested case-control study in the Multiethnic Cohort. British journal of cancer 20090707
Tissue distribution and elimination of sesaminol triglucoside and its metabolites in rat. Molecular nutrition & food research 20090701
Impact of a lignan-rich diet on adiposity and insulin sensitivity in post-menopausal women. The British journal of nutrition 20090701
Plasma phyto-oestrogens and prostate cancer in the European Prospective Investigation into Cancer and Nutrition. British journal of cancer 20090602
Lignans and breast cancer risk in pre- and post-menopausal women: meta-analyses of observational studies. British journal of cancer 20090505
Pleiotropic combinatorial transcriptomes of human breast cancer cells exposed to mixtures of dietary phytoestrogens. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20090401
The binding of lignans, flavonoids and coumestrol to CYP450 aromatase: a molecular modelling study. Molecular and cellular endocrinology 20090325
Plasma enterolignans are not associated with nonfatal myocardial infarction risk. Atherosclerosis 20090301
Dietary enterolactone affects androgen and estrogen levels in healthy postmenopausal women. Annals of the New York Academy of Sciences 20090201
Molecular and biochemical effects of a kola nut extract on androgen receptor-mediated pathways. Journal of toxicology 20090101
Isolation and bioactivities of furfuran type lignan compounds from edible plants. Recent patents on food, nutrition & agriculture 20090101
Effect of the form of the sesame-based diet on the absorption of lignans. The British journal of nutrition 20081201
Fecal and urinary lignans, intrafollicular estradiol, and endometrial receptors in lactating dairy cows fed diets supplemented with hydrogenated animal fat, flaxseed or sunflower seed. The Journal of reproduction and development 20081201
Phytoestrogens and phytoestrogen metabolites differentially modulate immune parameters in human leukocytes. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20081201
Phytoestrogen content of foods of animal origin: dairy products, eggs, meat, fish, and seafood. Journal of agricultural and food chemistry 20081112
Enterolactone is differently associated with estrogen receptor beta-negative and -positive breast cancer in a Swedish nested case-control study. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20081101
In vitro metabolism of flax lignans by ruminal and faecal microbiota of dairy cows. Journal of applied microbiology 20081101
Lack of prospective associations between plasma and urinary phytoestrogens and risk of prostate or colorectal cancer in the European Prospective into Cancer-Norfolk study. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20081001
The effect of a lignan complex isolated from flaxseed on inflammation markers in healthy postmenopausal women. Nutrition, metabolism, and cardiovascular diseases : NMCD 20080901
Dietary lariciresinol attenuates mammary tumor growth and reduces blood vessel density in human MCF-7 breast cancer xenografts and carcinogen-induced mammary tumors in rats. International journal of cancer 20080901
Variation in fasting and non-fasting serum enterolactone concentrations in women of the Malmö Diet and Cancer cohort. European journal of clinical nutrition 20080801
Environmental exposures and puberty in inner-city girls. Environmental research 20080701
Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. Journal of dairy science 20080701
Metabolism of the lignan macromolecule into enterolignans in the gastrointestinal lumen as determined in the simulator of the human intestinal microbial ecosystem. Journal of agricultural and food chemistry 20080625
Dietary flaxseed lignan extract lowers plasma cholesterol and glucose concentrations in hypercholesterolaemic subjects. The British journal of nutrition 20080601
Effects of dietary flaxseed lignan extract on symptoms of benign prostatic hyperplasia. Journal of medicinal food 20080601
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
Effects of metabolites of the lignans enterolactone and enterodiol on osteoblastic differentiation of MG-63 cells. Biological & pharmaceutical bulletin 20080601
Enterolactone restricts the proliferation of the LNCaP human prostate cancer cell line in vitro. Molecular nutrition & food research 20080501
Enterodiol and enterolactone, two major diet-derived polyphenol metabolites have different impact on ERalpha transcriptional activation in human breast cancer cells. The Journal of steroid biochemistry and molecular biology 20080501
Genome analysis of food grade lactic Acid-producing bacteria: from basics to applications. Current genomics 20080501
Urinary excretion of 13 dietary flavonoids and phenolic acids in free-living healthy subjects - variability and possible use as biomarkers of polyphenol intake. European journal of clinical nutrition 20080401
Plasma enterolignan concentrations and colorectal cancer risk in a nested case-control study. American journal of epidemiology 20080315
Global gene expression profiles induced by phytoestrogens in human breast cancer cells. Endocrine-related cancer 20080301
Dietary lignans and postmenopausal breast cancer risk by oestrogen receptor status: a prospective cohort study of Swedish women. British journal of cancer 20080212
Lignan content of selected foods from Japan. Journal of agricultural and food chemistry 20080123
Determination of urinary phytoestrogens by HPLC-MS/MS: a comparison of atmospheric pressure chemical ionization (APCI) and electrospray ionization (ESI). Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080101
Breast cancer risk in relation to urinary and serum biomarkers of phytoestrogen exposure in the European Prospective into Cancer-Norfolk cohort study. Breast cancer research : BCR 20080101
Relationship between metabolic and genomic diversity in sesame (Sesamum indicum L.). BMC genomics 20080101
An amphioxus orthologue of the estrogen receptor that does not bind estradiol: insights into estrogen receptor evolution. BMC evolutionary biology 20080101
Baseline urinary phytoestrogen levels and the natural history of untreated, localised prostate cancer in a British population. The International journal of biological markers 20080101
Timing of supplementation of selenium and isoflavones determines prostate cancer risk factor reduction in rats. Nutrition & metabolism 20080101
Antioxidant activities of the flaxseed lignan secoisolariciresinol diglucoside, its aglycone secoisolariciresinol and the mammalian lignans enterodiol and enterolactone in vitro. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20071101
Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria. Biological & pharmaceutical bulletin 20071101
Enantioselective oxidation of enterodiol to enterolactone by human intestinal bacteria. Biological & pharmaceutical bulletin 20071101
Diet-derived polyphenol metabolite enterolactone is a tissue-specific estrogen receptor activator. Endocrinology 20071001
The human peripheral blood mononuclear cell proteome responds to a dietary flaxseed-intervention and proteins identified suggest a protective effect in atherosclerosis. Proteomics 20070901
Enterolactone induces apoptosis in human prostate carcinoma LNCaP cells via a mitochondrial-mediated, caspase-dependent pathway. Molecular cancer therapeutics 20070901
Phyto-oestrogens and risk of prostate cancer in Scottish men. The British journal of nutrition 20070801
Occurrence of 'mammalian' lignans in plant and water sources. Planta 20070801
Metabolism of isoflavones, lignans and prenylflavonoids by intestinal bacteria: producer phenotyping and relation with intestinal community. FEMS microbiology ecology 20070801
Estrogenic activity of 7-hydroxymatairesinol potassium acetate (HMR/lignan) from Norway spruce (Picea abies) knots and of its active metabolite enterolactone in MCF-7 cells. Pharmacological research 20070801
Role of dietary lignans in the reduction of breast cancer risk. Molecular nutrition & food research 20070701
High throughput quantification of phytoestrogens in human urine and serum using liquid chromatography/tandem mass spectrometry (LC-MS/MS). Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070615
Tissue distribution of lignans in rats in response to diet, dose-response, and competition with isoflavones. Journal of agricultural and food chemistry 20070613
Variations in plasma phytoestrogen concentrations in European adults. The Journal of nutrition 20070501
Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone. Biological & pharmaceutical bulletin 20070501
Phytoestrogen exposure is associated with circulating sex hormone levels in postmenopausal women and interact with ESR1 and NR1I2 gene variants. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20070501
Dietary lignan intake and postmenopausal breast cancer risk by estrogen and progesterone receptor status. Journal of the National Cancer Institute 20070301
Plasma phytoestrogens and subsequent breast cancer risk. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20070220
Flaxseed and its lignans inhibit estradiol-induced growth, angiogenesis, and secretion of vascular endothelial growth factor in human breast cancer xenografts in vivo. Clinical cancer research : an official journal of the American Association for Cancer Research 20070201
Clostridium saccharogumia sp. nov. and Lactonifactor longoviformis gen. nov., sp. nov., two novel human faecal bacteria involved in the conversion of the dietary phytoestrogen secoisolariciresinol diglucoside. Systematic and applied microbiology 20070101
Pilot study of urinary biomarkers of phytoestrogens, phthalates, and phenols in girls. Environmental health perspectives 20070101
Maternal flaxseed diet during pregnancy or lactation increases female rat offspring's susceptibility to carcinogen-induced mammary tumorigenesis. Reproductive toxicology (Elmsford, N.Y.) 20070101
Hydroxymatairesinol and its mammalian metabolite enterolactone reduce the growth and metastasis of subcutaneous AH109A hepatomas in rats. Nutrition and cancer 20070101
Determination of mammalian lignans in biological samples by modified gas chromatography/mass spectrometry. Journal of AOAC International 20070101
Dietary fiber intake and endogenous serum hormone levels in naturally postmenopausal Mexican American women: the Multiethnic Cohort Study. Nutrition and cancer 20070101
Lignans and human health. Critical reviews in clinical laboratory sciences 20070101
Effects of a flaxseed-derived lignan supplement in type 2 diabetic patients: a randomized, double-blind, cross-over trial. PloS one 20070101
Intake of dietary phytoestrogen and indices of antioxidant and bone metabolism of pre- and post-menopausal Korean women. Nutrition research and practice 20070101
Effect of sesamin on serum cholesterol and triglycerides levels in LDL receptor-deficient mice. European journal of nutrition 20061201
Bioavailability of lignans in human subjects. Nutrition research reviews 20061201
Circulating enterolactone and risk of endometrial cancer. International journal of cancer 20061115
Genistein alone and in combination with the mammalian lignans enterolactone and enterodiol induce estrogenic effects on bone and uterus in a postmenopausal breast cancer mouse model. Bone 20060701
Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. The British journal of nutrition 20060701
Determination of plant and enterolignans in human serum by high-performance liquid chromatography with tandem mass spectrometric detection. Journal of pharmaceutical and biomedical analysis 20060607
Plasma enterolactone and genistein and the risk of premenopausal breast cancer. European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20060601
Phyto-oestrogen intake and plasma concentrations in South Asian and native British women resident in England. The British journal of nutrition 20060601
Plasma enterolignans are associated with lower colorectal adenoma risk. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20060601
Serum enterolactone concentration and the risk of coronary heart disease in a case-cohort study of Finnish male smokers. American journal of epidemiology 20060415
Urolithins, ellagic acid-derived metabolites produced by human colonic microflora, exhibit estrogenic and antiestrogenic activities. Journal of agricultural and food chemistry 20060308
Secoisolariciresinol dehydrogenase: mode of catalysis and stereospecificity of hydride transfer in Podophyllum peltatum. Organic & biomolecular chemistry 20060307
Mammalian lignans enterolactone and enterodiol, alone and in combination with the isoflavone genistein, do not promote the growth of MCF-7 xenografts in ovariectomized athymic nude mice. International journal of cancer 20060301
Enterolactone as a risk factor for breast cancer: a review of the published evidence. Clinica chimica acta; international journal of clinical chemistry 20060301
Dietary phytoestrogen, serum enterolactone and risk of prostate cancer: the cancer prostate Sweden study (Sweden). Cancer causes & control : CCC 20060301
Phylogeny of human intestinal bacteria that activate the dietary lignan secoisolariciresinol diglucoside. FEMS microbiology ecology 20060301
Polyphenolic constituents of Actaea racemosa. Journal of natural products 20060301
The plant lignans matairesinol and secoisolariciresinol administered to Min mice do not protect against intestinal tumor formation. Cancer letters 20060227
Suitability of a batch in vitro fermentation model using human faecal microbiota for prediction of conversion of flaxseed lignans to enterolactone with reference to an in vivo rat model. European journal of nutrition 20060201
Xenobiotic phenols in early pregnancy amniotic fluid. Reproductive toxicology (Elmsford, N.Y.) 20060101
Prostatic phyto-oestrogen tissue levels in different Austrian regions. Urologia internationalis 20060101
Flax lignans--analytical methods and how they influence our lunderstanding of biological activity. Journal of AOAC International 20060101
Assessing exposure to lignans and their metabolites in humans. Journal of AOAC International 20060101
Phytoestrogen exposure, polymorphisms in COMT, CYP19, ESR1, and SHBG genes, and their associations with prostate cancer risk. Nutrition and cancer 20060101
Lignans, bacteriocides and organochlorine compounds activate the human pregnane X receptor (PXR). Toxicology and applied pharmacology 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
Urinary phytoestrogen concentrations in the U.S. population (1999-2000). Journal of exposure analysis and environmental epidemiology 20051101
Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. The British journal of nutrition 20051001
Plasma levels of enterolactone and percentage mammographic density among postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20050901
A validated method for the quantification of enterodiol and enterolactone in plasma using isotope dilution liquid chromatography with tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050805
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
Phytoestrogens and prostate cancer risk. Preventive medicine 20050701
Optimization of conditions for the enzymatic hydrolysis of phytoestrogen conjugates in urine and plasma. Analytical biochemistry 20050615
Analysis of environmental biomarkers in urine using an electrochemical detector. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050505
Crystal structures of apo-form and binary/ternary complexes of Podophyllum secoisolariciresinol dehydrogenase, an enzyme involved in formation of health-protecting and plant defense lignans. The Journal of biological chemistry 20050401
Mammalian lignans and genistein decrease the activities of aromatase and 17beta-hydroxysteroid dehydrogenase in MCF-7 cells. The Journal of steroid biochemistry and molecular biology 20050401
Uptake and metabolism of enterolactone and enterodiol by human colon epithelial cells. Archives of biochemistry and biophysics 20050301
[Effects of phytoestrogens on gap junctional intercellular communication]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20050301
Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. The British journal of nutrition 20050301
A thirteen week dietary toxicity study with 7-hydroxymatairesinol potassium acetate (HMRlignan) in rats. Regulatory toxicology and pharmacology : RTP 20050201
Structural determinants of plant lignans for growth of mammary tumors and hormonal responses in vivo. The Journal of steroid biochemistry and molecular biology 20050201
Phytoestrogen exposure correlation with plasma estradiol in postmenopausal women in European Prospective Investigation of Cancer and Nutrition-Norfolk may involve diet-gene interactions. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20050101
Enterolactone induces apoptosis and inhibits growth of Colo 201 human colon cancer cells both in vitro and in vivo. Anticancer research 20050101
Whole sesame seed is as rich a source of mammalian lignan precursors as whole flaxseed. Nutrition and cancer 20050101
Urinary excretion of lignans after administration of isolated plant lignans to rats: the effect of single dose and ten-day exposures. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20041225
Plasma enterolactone and breast cancer incidence by estrogen receptor status. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20041201
Prospective study of plasma enterolactone and prostate cancer risk (Sweden). Cancer causes & control : CCC 20041201
Phytoestrogen tissue levels in benign prostatic hyperplasia and prostate cancer and their association with prostatic diseases. Urology 20041001
Automated online and off-line solid-phase extraction methods for measuring isoflavones and lignans in urine. Journal of chromatographic science 20041001
Glucuronidation, oxidative metabolism, and bioactivation of enterolactone in rhesus monkeys. Archives of biochemistry and biophysics 20040915
Determination of lignans in human plasma by liquid chromatography with coulometric electrode array detection. Analytical biochemistry 20040915
Determination of phytoestrogens in traditional medicinal herbs using gas chromatography--mass spectrometry. The Journal of nutritional biochemistry 20040801
Circulating enterolactone and risk of breast cancer: a prospective study in New York. British journal of cancer 20040705
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
Dietary phytoestrogen intake and premenopausal breast cancer risk in a German case-control study. International journal of cancer 20040610
A new lariciresinol-type butyrolactone lignan derived from hydroxymatairesinol and its identification in spruce wood. Journal of natural products 20040601
Highly elevated serum phyto-oestrogen concentrations in patients with diabetic nephropathy. Journal of internal medicine 20040501
Chemopreventive effects of hydroxymatairesinol on uterine carcinogenesis in Donryu rats. Experimental biology and medicine (Maywood, N.J.) 20040501
Phytoestrogen concentrations in serum and spot urine as biomarkers for dietary phytoestrogen intake and their relation to breast cancer risk in European prospective investigation of cancer and nutrition-norfolk. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20040501
Stereospecific Pd(O)-catalyzed malonate additions to allylic hydroxy phosphonate derivatives: a formal synthesis of (-)-enterolactone. The Journal of organic chemistry 20040416
Serum enterolactone concentration is not associated with breast cancer risk in a nested case-control study. International journal of cancer 20040110
Serum enterolactone levels and the risk of breast cancer in women with palpable cysts. European journal of cancer (Oxford, England : 1990) 20040101
Regulation of low-density lipoprotein receptor activity by estrogens and phytoestrogens in a HepG2 cell model. Annals of nutrition & metabolism 20040101
Reports: plasma and dietary phytoestrogens and risk of premalignant lesions of the cervix. Nutrition and cancer 20040101
Nutrition and cancer: a review of the evidence for an anti-cancer diet. Nutrition journal 20040101
The effect of estrogens and phytoestrogenic lignans on macrophage uptake of atherogenic lipoproteins. BioFactors (Oxford, England) 20040101
Liquid chromatography method for plant and mammalian lignans in human urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20031205
Serum enterolactone concentration is not associated with prostate cancer risk in a nested case-control study. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20031101
Studies on the metabolism of the plant lignans secoisolariciresinol and matairesinol. Journal of agricultural and food chemistry 20031008
Randomised controlled short-term intervention pilot study on rye bran bread in prostate cancer. European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20031001
Liquid chromatographic-tandem mass spectrometric method for the plant lignan 7-hydroxymatairesinol and its potential metabolites in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20030815
Plasma enterolactone or intestinal Bifidobacterium levels do not explain adenoma formation in multiple intestinal neoplasia (Min) mice fed with two different types of rye-bran fractions. The British journal of nutrition 20030701
Lignans and tamoxifen, alone or in combination, reduce human breast cancer cell adhesion, invasion and migration in vitro. Breast cancer research and treatment 20030701
Urinary and serum concentrations of seven phytoestrogens in a human reference population subset. Journal of exposure analysis and environmental epidemiology 20030701
Bioavailability of phyto-oestrogens. The British journal of nutrition 20030601
Risk of cardiovascular disease-related and all-cause death according to serum concentrations of enterolactone: Kuopio Ischaemic Heart Disease Risk Factor Study. Archives of internal medicine 20030512
Enterolactone in breast cyst fluid: correlation with EGF and breast cancer risk. Breast cancer research and treatment 20030501
Quantification of isoflavones and lignans in urine using gas chromatography/mass spectrometry. Analytical biochemistry 20030401
Synthesis of (-)-matairesinol, (-)-enterolactone, and (-)-enterodiol from the natural lignan hydroxymatairesinol. Organic letters 20030220
Rye, lignans and human health. The Proceedings of the Nutrition Society 20030201
Short-term variations in enterolactone in serum, 24-hour urine, and spot urine and relationship with enterolactone concentrations. Clinical chemistry 20030101
Phytoestrogens and breast cancer risk. Review of the epidemiological evidence. Breast cancer research and treatment 20030101
Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid communications in mass spectrometry : RCM 20030101
Quantification of isoflavones and lignans in serum using isotope dilution liquid chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM 20030101
Phytoestrogens and breast cancer. The Journal of steroid biochemistry and molecular biology 20021201
Mammalian lignan formation in rats fed a wheat bran diet. Journal of agricultural and food chemistry 20021009
Phloem fortification in rye bread elevates serum enterolactone level. European journal of clinical nutrition 20021001
Liquid chromatographic-photodiode array mass spectrometric analysis of dietary phytoestrogens from human urine and blood. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020925
Mammalian phytoestrogens: enterodiol and enterolactone. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020925
Structural determinants of plant lignans for the formation of enterolactone in vivo. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020925
Oxidative metabolites and genotoxic potential of mammalian and plant lignans in vitro. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020925
Whole grain food intake elevates serum enterolactone. The British journal of nutrition 20020801
An incident case-referent study on plasma enterolactone and breast cancer risk. European journal of nutrition 20020801
Enterolactone inhibits the growth of 7,12-dimethylbenz(a)anthracene-induced mammary carcinomas in the rat. Molecular cancer therapeutics 20020801
Antioxidant and antitumor effects of hydroxymatairesinol (HM-3000, HMR), a lignan isolated from the knots of spruce. European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20020801
Phyto-oestrogens and cancer. The Lancet. Oncology 20020601
Circulating enterolactone and prostate cancer risk: a Nordic nested case-control study. International journal of cancer 20020501
Comparative study of concentration of isoflavones and lignans in plasma and prostatic tissues of normal control and benign prostatic hyperplasia. Yonsei medical journal 20020401
Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid. The Journal of organic chemistry 20020322
Use of oral antimicrobials decreases serum enterolactone concentration. American journal of epidemiology 20020301
Relationships of urinary phyto-oestrogen excretion to BMD in postmenopausal women. Clinical endocrinology 20020301
Association between low serum enterolactone and increased plasma F2-isoprostanes, a measure of lipid peroxidation. Atherosclerosis 20020201
The effect of flaxseed supplementation in processed foods on serum fatty acids and enterolactone. European journal of clinical nutrition 20020201
Dietary determinants of plasma enterolactone. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20020101
Exposure to flaxseed or its purified lignan during suckling only or continuously does not alter reproductive indices in male and female offspring. Journal of toxicology and environmental health. Part A 20011207
In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. Journal of agricultural and food chemistry 20010701
Exposure to flaxseed and its purified lignan reduces bone strength in young but not older male rats. Journal of toxicology and environmental health. Part A 20010511
Analytical performance of luminescent immunoassays of different format for serum daidzein analysis. Fresenius' journal of analytical chemistry 20010501
Secoisolariciresinol dehydrogenase purification, cloning, and functional expression. Implications for human health protection. The Journal of biological chemistry 20010420
Phytochemical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor alpha and beta. The Journal of clinical endocrinology and metabolism 20010401
Serum enterolactone and risk of breast cancer: a case-control study in eastern Finland. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20010401
Urinary phytoestrogens and postmenopausal breast cancer risk. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20010301
Effect of mammalian lignans on the growth of prostate cancer cell lines. Anticancer research 20010101
Uptake and metabolism of hydroxymatairesinol in relation to its anticarcinogenicity in DMBA-induced rat mammary carcinoma model. Nutrition and cancer 20010101
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