Equol: history, chemistry, and formation (Q24594674)

The pharmacokinetic behavior of the soy isoflavone metabolite S-(-)equol and its diastereoisomer R-(+)equol in healthy adults determined by using stable-isotope-labeled tracers

Europe PubMed Central

title

Equol: history, chemistry, and formation (English)

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Kenneth D R Setchell

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Carlo Clerici

series ordinal

2

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language of work or name

English

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publication date

July 2010

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published in

Journal of Nutrition

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volume

140

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issue

7

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page(s)

1355S-62S

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cites work

1 reference

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Equol, a new inactive phenol isolated from the ketohydroxyoestrin fraction of mares' urine

24 March 2017

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Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium

24 March 2017

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The identification of the weak oestrogen equol [7-hydroxy-3-(4'-hydroxyphenyl)chroman] in human urine

24 March 2017

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Method of defining equol-producer status and its frequency among vegetarians

24 March 2017

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Prevalence of daidzein-metabolizing phenotypes differs between Caucasian and Korean American women and girls

24 March 2017

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

24 March 2017

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

24 March 2017

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Interindividual variation in metabolism of soy isoflavones and lignans: influence of habitual diet on equol production by the gut microflora

24 March 2017

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Comparison of isoflavones among dietary intake, plasma concentration and urinary excretion for accurate estimation of phytoestrogen intake

24 March 2017

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Pharmacokinetics of soybean isoflavones in plasma, urine and feces of men after ingestion of 60 g baked soybean powder (kinako)

24 March 2017

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Urinary equol excretion with a soy challenge: influence of habitual diet

24 March 2017

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Genistein, a specific inhibitor of tyrosine-specific protein kinases

24 March 2017

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Urinary phytoestrogen excretion and postmenopausal breast cancer risk: the multiethnic cohort study

7 April 2017

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The pharmacokinetics of S-(-)equol administered as SE5-OH tablets to healthy postmenopausal women

27 September 2017

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

27 September 2017

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Plasma phyto-oestrogens and prostate cancer in the European Prospective Investigation into Cancer and Nutrition

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Is equol the key to the efficacy of soy foods?

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Stereospecific biotransformation of dihydrodaidzein into (3S)-equol by the human intestinal bacterium Eggerthella strain Julong 732.

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Isolation of a human intestinal bacterium capable of daidzein and genistein conversion

27 September 2017

1 reference

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Conversion of daidzein and genistein by an anaerobic bacterium newly isolated from the mouse intestine.

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Asaccharobacter celatus gen. nov., sp. nov., isolated from rat caecum

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Breast cancer risk in relation to urinary and serum biomarkers of phytoestrogen exposure in the European Prospective into Cancer-Norfolk cohort study

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Variations in phytoestrogen content between different mill dates of the same diet produces significant differences in the time of vaginal opening in CD-1 mice and F344 rats but not in CD Sprague-Dawley rats

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Isolation of an isoflavone-metabolizing, Clostridium-like bacterium, strain TM-40, from human faeces

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

p-Ethylphenylsulphuric acid in goat urine

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Selecting the appropriate rodent diet for endocrine disruptor research and testing studies

27 September 2017

1 reference

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Oestrogenic activity of subterranean clover. I. The oestrogenic activity of genistein

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Treatment with antibiotics reduces plasma equol concentration in cynomolgus monkeys (Macaca fascicularis).

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

The clinical importance of the metabolite equol-a clue to the effectiveness of soy and its isoflavones

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

27 September 2017

1 reference

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Dietary isoflavones: biological effects and relevance to human health

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Metabolism of estrogenic isoflavones in domestic animals.

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

In vitro hormonal effects of soybean isoflavones

27 September 2017

1 reference

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Nonsteroidal estrogens of dietary origin: possible roles in hormone-dependent disease

27 September 2017

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Origin of lignans in mammals and identification of a precursor from plants

27 September 2017

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Lignan formation in man--microbial involvement and possible roles in relation to cancer

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Lability of equol to acidic hydrolysis procedures

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Composition of some urinary calculi of ruminants in Western Australia

27 September 2017

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The effects of plant oestrogens on animal reproduction

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

The constitution of equol

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

The definitive identification of the lignans trans-2,3-bis(3-hydroxybenzyl)-γ-butyrolactone and 2,3-bis(3-hydroxybenzyl)butane-1,4-diol in human and animal urine

30 May 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Identification of lignans and phytoestrogens in urine of chimpanzees.

30 May 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Excretion of Radioactive Daidzein and Equol as Monosulfates and Disulfates in the Urine of the Laying Hen

30 May 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Dietary seaweed modifies estrogen and phytoestrogen metabolism in healthy postmenopausal women

30 May 2018

1 reference

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Report on the 8th International Symposium on the Role of Soy in Health Promotion and Chronic Disease Prevention and Treatment.

28 November 2018

1 reference

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

28 November 2018

1 reference

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

28 November 2018

1 reference

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Bioconversion of soy isoflavones daidzin and daidzein by Bifidobacterium strains

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Oral antibiotics decrease urinary isoflavonoid excretion in children after soy consumption

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Low activities of intestinal lactase suppress the early phase absorption of soy isoflavones in Japanese adults

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Microbial and dietary factors are associated with the equol producer phenotype in healthy postmenopausal women

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Phenotypic typing, technological properties and safety aspects of Lactococcus garvieae strains from dairy environments.

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Variations in plasma phytoestrogen concentrations in European adults

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Metabolic phenotype of isoflavones differ among female rats, pigs, monkeys, and women

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Urinary phytoestrogen concentrations in the U.S. population (1999-2000).

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Familial correlations, segregation analysis, and nongenetic correlates of soy isoflavone-metabolizing phenotypes

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Higher consumption of green tea may enhance equol production

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Dietary phytoestrogens accelerate the time of vaginal opening in immature CD-1 mice.

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Metabolism of the soybean isoflavone glycoside genistin in vitro by human gut bacteria and the effect of prebiotics

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Variations in isoflavone levels in soy foods and soy protein isolates and issues related to isoflavone databases and food labeling

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Solvent extraction selection in the determination of isoflavones in soy foods

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Transfer of soy isoflavone into the egg yolk of chickens

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Phytoestrogen content of purified, open- and closed-formula laboratory animal diets.

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2884333

Isoflavone content of infant formulas and the metabolic fate of these phytoestrogens in early life

28 November 2018

1 reference

12 December 2020

Safety and pharmacokinetics of purified soy isoflavones: single-dose administration to postmenopausal women

1 reference

12 December 2020

Exposure of infants to phyto-oestrogens from soy-based infant formula

1 reference

12 December 2020

Lignans in man and in animal species

1 reference

12 December 2020

Dietary intake and sources of isoflavones among Japanese

1 reference

12 December 2020

Urinary pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein

1 reference

12 December 2020

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

1 reference

12 December 2020

In vitro incubation of human feces with daidzein and antibiotics suggests interindividual differences in the bacteria responsible for equol production

1 reference

12 December 2020

Biotransformation of genistein in the rat: elucidation of metabolite structure by product ion mass fragmentology

1 reference

12 December 2020

The variable metabolic response to dietary isoflavones in humans

1 reference

12 December 2020

Soy isoflavone aglycones are absorbed faster and in higher amounts than their glucosides in humans

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12 December 2020

Plasma phytoestrogens are not altered by probiotic consumption in postmenopausal women with and without a history of breast cancer

1 reference

12 December 2020

Dietary fructooligosaccharides modify intestinal bioavailability of a single dose of genistein and daidzein and affect their urinary excretion and kinetics in blood of rats

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12 December 2020

Total synthesis of (S)-equol

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12 December 2020

Demethylation of the Plant Œstrogen Biochanin A in the Rat

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12 December 2020

The excretion of lignans in rats -- evidence for an intestinal bacterial source for this new group of compounds

1 reference

12 December 2020

Plasma and urinary kinetics of the isoflavones daidzein and genistein after a single soy meal in humans

1 reference

12 December 2020

The metabolism of Phyto-oestrogens in sheep

1 reference

12 December 2020

Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements

1 reference

12 December 2020

Isolation of human intestinal bacteria metabolizing the natural isoflavone glycosides daidzin and genistin

1 reference

12 December 2020

Comparing the pharmacokinetics of daidzein and genistein with the use of 13C-labeled tracers in premenopausal women

1 reference

12 December 2020

Pasta naturally enriched with isoflavone aglycons from soy germ reduces serum lipids and improves markers of cardiovascular risk

1 reference

12 December 2020

Chemical synthesis of [(13)c]daidzein

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12 December 2020

Identification of equol in the urine of the domestic fowl

1 reference

12 December 2020

Radioactive conversion products of intramuscularly injected [4-14C]formononetin including sulfates in the urine of hens

1 reference

12 December 2020

Steroid and phyto-oestrogen binding to sheep uterine receptors in vitro

1 reference

12 December 2020

Synthesis and labeling of isoflavone phytoestrogens, including daidzein and genistein

1 reference

12 December 2020

The development of the bacterial flora in normal neonates

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12 December 2020

THE CONVERSION OF GENISTEIN TO EQUOL IN THE FOWL

1 reference

12 December 2020

Steroids and other lipids of pregnant cow's urine

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12 December 2020

Conjugation of Lignans in human urine

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12 December 2020

Bioavailability of soybean isoflavones from aglycone and glucoside forms in American women

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12 December 2020

Synthesis of 13C labelled daidzein and formononetin

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12 December 2020

Evidence for lack of absorption of soy isoflavone glycosides in humans, supporting the crucial role of intestinal metabolism for bioavailability

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12 December 2020

On the mechanism of estrogen action

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12 December 2020

Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver beta-glucosidase activity

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12 December 2020

Wheat bran and soy protein feeding do not alter urinary excretion of the isoflavan equol in premenopausal women

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12 December 2020

Probiotic consumption does not enhance the cholesterol-lowering effect of soy in postmenopausal women

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12 December 2020

Identification of phytoestrogens in the urine of male dogs

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12 December 2020

Genistein, daidzein, and their .beta.-glycoside conjugates: antitumor isoflavones in soybean foods from American and Asian diets

1 reference

Crossref

https://api.crossref.org/works/10.3945%2FJN.109.119776

7 January 2021

inferred from DOI database lookup

Identifiers

DOI

10.3945/JN.109.119776

1 reference

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PubMed publication ID

20519412

1 reference