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PubMed1995

Effects of coumestrol and equol on the developing reproductive tract of the rat.

The phytoestrogens, coumestrol and equol, are weakly estrogenic. Here, we have examined their ability to induce responses in the neonatal rat uterus. Potent estrogens such as diethylstilbestrol (DES) and 17 beta-estradiol which initially double uterine weight on postnatal Day (PND) 5 when given on PND 1-5 subsequently reduce both uterine growth and gland development at later ages. In this study, Sprague-Dawley pups were treated neonatally (PND 1-5) with various doses of coumestrol and equol, and sacrificed at different ages to determine alterations in biochemical and morphological endpoints. Other rats were injected with the same compounds during the critical period of gland genesis (PND 10-14) to examine their effects on gland development. At the 100 micrograms coumestrol dose, on PND 1-5, premature gland development and increased uterine weight were observed. However, at later ages, uterine weight was significantly lowered and there was a severe suppression in the estrogen receptor (ER) levels. Equol lowered uterine weight at the later ages but did not affect ER levels. When given on PND 10-14, both coumestrol and equol caused a dose-dependent inhibition of gland genesis though not as severe as either DES or tamoxifen. Coumestrol was about 10(3) more potent than equol as an estrogen and behaved much like DES with respect to its effects on uterine weight, glands, and ER levels. At the doses used in this study, equol failed to demonstrate either estrogenic or antiestrogenic activity.

Animals↗
PubMedDate not supplied

Protective effect of the isoflavonoid equol against hairless mouse skin carcinogenesis induced by UV radiation alone or with a chemical cocarcinogen.

Isoflavones derived from many edible plants, such as genistein from the soybean, have well-documented antioxidant and estrogenic activity but may also be anticarcinogenic. In this study, we examined the potential of the isoflavone equol [(S)-4',7-dihydroxyisoflavane] to protect from skin carcinogenesis in the hairless mouse. Daily topical applications of equol lotions significantly protected against skin carcinogenesis induced by chronic exposure to solar-simulated UV radiation (SSUV) or by topical treatment with the chemical carcinogen 7,12-dimethylbenz(a)anthracene (DMBA) or by the combined cocarcinogenic treatment of DMBA followed by chronic SSUV. Monitoring of tumor development for 40 weeks showed significantly delayed tumor appearance and reduced tumor multiplicity in all equol-treated groups. In mice treated with either SSUV or DMBA + SSUV, equol significantly reduced the proportion of tumors progressing from benign papillomas to malignant squamous cell carcinoma (SCC) by 33-58% and reduced the average diameter of SCC by 71-82%. In a short-term study, equol dose dependently inhibited the SSUV induction of the tumor promotion biomarker enzyme, ornithine decarboxylase, in the skin, suggesting the anticarcinogenic activity of equol may be attributed to its inhibition of the tumor promotion phase of carcinogenesis.

Animals↗
PubMed2004

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

Dietary soy-isoflavones have recently been noted as phytoestrogens with potentially beneficial effects on human health, and they are biologically transformed in the intestinal tract into aglycones and further into several specific metabolites. Here we report that in laying hens daidzin, a soy isoflavone-glycoside, in the diet was transformed into equol, absorbed, transported in circulating peripheral blood, and preferentially accumulated into egg yolk in its conjugated form. Laying hens were fed experimental diets containing two levels of soy isoflavone-glycosides (177 or 528 mg per 100 g diet) for 21 or 42 days, and blood and eggs were collected at 1- to 9-day intervals. HPLC analyses revealed that most of the isoflavones (daidzein, glycitein, and genistein) and a metabolite, equol, were present in blood and egg yolk in conjugated form. The concentration of equol-conjugates in blood plasma and egg yolk was higher than any of the other three isoflavone-conjugates analyzed and, especially in egg yolk, the equol-conjugates comprised no less than 60% of the total isoflavone-conjugates. The isoflavones, including equol, distributed mostly (95%) in the high-density fraction of blood serum, and more (65%) in the granule fraction of egg yolk. These results raise the possibility that feeding domestic animals soy-based fodder produces animal-based foods rich in a more active form of phytoestrogens.

Animal Feed↗
PubMed2005

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

The extent of conversion of daidzein to its metabolite, equol, by intestinal microflora may be a critical step that determines if a diet rich in daidzein protects against the deterioration of bone after estrogen withdrawal. The objective was to determine the extent that daidzein is converted to equol. In addition, bone mineral content (BMC), bone mineral density (BMD) and strength of femurs and lumbar vertebrae (LV) in four mouse strains were measured. Mice were ovariectomized and fed control diet (AIN93G) with or without daidzein (200 mg daidzein/kg diet) for 3 weeks, after which serum, femurs and LV were collected. Serum daidzein and equol were elevated in all mice fed daidzein. Among mice fed daidzein, the CD-1 and Swiss-Webster (SW) mice had higher (P<.001) serum equol than C57BL/6 (C57) and C3H mice. Differences due to mouse strain were observed for all bone outcomes. C57 mice had lower femur BMC (P<.001), BMD (P<.001) and peak load at femur midpoint (P<.001) and neck (P<.001) than other mouse strains. C57 mice also had a lower femur midpoint yield load (P<.001) and resilience (P<.001) than C3H mice. C57 mice had a lower LV1-4 BMC (P<.001) and BMD (P<.001) compared with all mouse strains and peak load of LV3 was lower than CD-1 and SW mice. Differences in serum equol, BMD and bone strength properties should be considered when selecting a mouse strain for investigating whether dietary strategies that include isoflavones preserve bone tissue after ovariectomy.

Animals↗
PubMed2006

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

Human and animal studies suggest that dietary soy isoflavones reduce cancer risk, ameliorate postmenopausal syndrome and decrease bone resorption in postmenopausal women. The capacity to form the metabolite equol from daidzein is suggested as an important modulator of response to isoflavones; this capacity depends on gut colonization with appropriate bacteria. We administered a dietary supplement containing high-dose purified soy isoflavones (genistein, 558 mg/day; daidzein, 296 mg/day; and glycitein, 44 mg/day) to 30 postmenopausal women for 84 days and collected peripheral lymphocytes at timed intervals. Using microarray analysis, we determined whether changes in gene expression associated with this treatment support existing hypotheses as to isoflavones' mechanisms of action. Expression of a large number of genes was altered by isoflavone treatment, including induction of genes associated with cyclic adenosine 3',5'-monophosphate (cAMP) signaling and cell differentiation and decreased expression of genes associated with cyclin-dependent kinase activity and cell division. We report that isoflavone treatment in subjects who have the capacity to produce equol differentially affects gene expression as compared with nonproducers, supporting the plausibility of the importance of equol production. In general, isoflavones had a stronger effect on some putative estrogen-responsive genes in equol producers than in nonproducers. Our study suggests that, in humans, isoflavone changes are related to increased cell differentiation, increased cAMP signaling and G-protein-coupled protein metabolism and increased steroid hormone receptor activity and have some estrogen agonist effects; equol-production status is likely to be an important modulator of responses to isoflavones.

Administration, Oral↗
PubMed2006

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

Equol production, isoflavone excretion, and the salivary estradiol profile among 36 females, native Irish Caucasian volunteers following ingestion of 200mL soymilk is reported. The soymilk contained daidzein (73+/-6.7mg) and genistein (86+/-10.2mg). Volunteers provided personal and family medical history. Dietary analysis revealed that all volunteers regularly consumed soy-based or soy-supplemented food products. The mean age, mean age at menarche, and body mass index of volunteers were 46.6+/-12.3 years, 13.1 years and 26.1, respectively. The average number of children per volunteer was 2.13. Twelve (34%) of the volunteers were found to be first-degree relatives of breast cancer patients. Following consumption of the soymilk, equol was detected in the urine of 18 (51%) of the volunteers. Mean urinary daidzein and genistein concentrations during the hours following soymilk ingestion were 13.5 and 16.7microg/mg creatinine, respectively, however, some volunteers excreted little (less than 4.0microg/mg) or no isoflavone. Salivary estradiol in most (24) volunteers had decreased from 51.5+/-28.67pmol/L pre-ingestion to 29.75+/-16.13pmol/L 5h after drinking the soymilk. However, the salivary estradiol in 12 subjects (34%) increased from 33.76+/-13.4pmol/L to 137.4+/-65.64pmol/L over the same period. Individuals whose salivary estradiol increased had significantly less children (1.58 (P<0.05)), were more likely to (a) return urine samples with low isoflavone content (50.3% compared to 25%), (b) to be equol producers (67% compared to 41.7%), and (c) to be first-degree relatives of breast cancer patients (41.7% compared to 25%). Volunteers who reported a first-degree link to breast cancer were more likely to have a higher body mass index (29.0 compared to 26.1 (P<0.05)), to be equol producers (75% compared to 51%), and to excrete isoflavones in low quantities only (60% compared to 50%). First-degree relatives also had fewer children (1.75 (P<0.05)). The results indicate a significant, distinctive variation in equol production, isoflavone excretion and salivary estradiol profile among individual volunteers following ingestion of soymilk.

Adult↗
PubMed2004

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

BACKGROUND: Our previous case-control study revealed that the Japanese residents in Japan could be divided into those who are able to degrade daidzein, a soybean isoflavone, to equol and those without this ability, and that the incidence of prostate cancer is higher in the latter group. METHODS: We recently conducted a similar case-control study involving not only Japanese residents in Japan but also Korean residents in Korea. The incidence of prostate cancer in Korean residents is known to be close to that of Japanese residents in Japan. On the other hand, American residents in the United States have a markedly higher incidence of prostate cancer as compared to Japanese residents in Japan. RESULTS: The number of subjects was 295 in Japan (133 patients and 162 controls), 122 in Korea (61 patients and 61 controls) and 45 in the United States (24 patients and 21 controls). The percentage of equol producers among patients and controls was 29% and 46% in Japan (P = 0.004) and 30% and 59% in Korea (P = 0.001), respectively. The active isoflavone level was markedly lower and the percentage of equol producers was also lower (17% for patients and 14% for controls) for Americans as compared to the Japanese and Koreans. CONCLUSIONS: These results suggest that the ability of producing equol or equol itself is closely related to the lower incidence of prostate cancer. The results also suggest that a diet based on soybean isoflavones will be useful in preventing prostate cancer.

Adult↗
PubMed2006

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

Isoflavones (mainly daidzein and genistin) belong to the flavonoid group of compounds and are classified as phytoestrogens. In the intestine, daidzin is converted to daidzein by beta-glucosidase, and then daidzein is converted to O-desmethylangolensin (O-DMA) or equol via dihydrodaidzein by enzymes of intestinal bacteria. We isolated, for the first time, an anaerobic gram-positive rod-shaped strain capable of producing equol from daidzein. Its 16S rDNA gene sequence (1428 bp) showed 99% similarity with that of the human intestinal bacterium SNU-Julong 732 (AY310748) and 93% similarity with that of Eggerthella lenta ATCC 25559(T) (AF292375). This strain converted daidzein to equol via dihydrodaidzein in an equol-assay medium anaerobically. The addition of butyric acid and arginine increased the conversion ratio of daidzein to equol 4.7- and 4.5-fold, respectively.

Actinobacteria↗
PubMed2003

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

The estrogenic isoflavone compound genistein recently has been found in the effluents of sewage treatment plants and pulp mills, and the related compound equol has been detected in the runoff from agricultural fields treated with hog manure. Waterborne exposures of Japanese medaka (Oryzias latipes) to equol from soon after hatch to approximately 100 days posthatch induced gonadal intersex (i.e., testis-ova) in males at incidences of 10 and 87% in equol treatments of 0.4 and 0.8 micro g/L, respectively. Exposure to the highest test concentration of genistein, 1,000 micro g/L, also caused a low incidence (i.e., 12%) of gonadal intersex in male medaka. The ovaries of female medaka from both equol and genistein treatments showed delayed oocyte maturation, atretic oocytes, an enlarged ovarian lumen, proliferation of somatic stromal tissue, and primordial germ cells; responses were concentration dependent. Alterations to externally visible secondary sex characteristics occurred in medaka exposed to both equol and genistein. In treatments with 1,000 micro g/L genistein, 72% of male medaka (as identified by the gonadal phenotype) showed feminized secondary sex characteristics. Gonadal intersex and alterations to secondary sex characteristics have been noted in several fish populations around the world. This laboratory study indicates that isoflavone compounds should be considered candidate estrogenic compounds that may be involved in the alteration of sexual development in feral fish populations.

Animals↗
PubMed1980

Effect of equol on oestrogen receptors and on synthesis of DNA and protein in the immature rat uterus.

In immature, 3-week-old female rats, 5 mg equol given by subcutaneous injection increased uterine wet weight 24 h later to the same degree as did 5 microgram oestradiol-17 beta. At this dose there was more receptor complex binding to the nucleus in the equol-injected rats than in the rats injected with oestradiol-17 beta even after 6 h. However, the equol-receptor complex that bound to the nucleus was more extractable with 0 x 3 M-KCl. In the equol-injected rats the duration of uterine growth was shorter and there was less receptor replenishment and synthesis of protein and DNA than in the rats injected with oestradiol-17 beta 30 h after either injection. It was concluded that equol is a weakly oestrogenic compound which is antagonistic to oestradiol-17 beta by competing with oestradiol-receptor complex for nuclear binding and yet fails to initiate the replenishment of oestrogen receptors effectively in the cytoplasm.

Animals↗
PubMed1984

Soya--a dietary source of the non-steroidal oestrogen equol in man and animals.

The dietary origin of the weak oestrogen equol (7-hydroxy-3-(4'-hydroxyphenyl)-chroman) present in human urine has been investigated using gas chromatography-mass spectrometry. Feeding experiments with different food constituents and monitoring the urinary excretion of equol revealed that soya food yields more than 0.1 mg urinary equol/g flour ingested. From this source the glucoside of daidzein (4',7-dihydroxyisoflavone) has been isolated and identified as a precursor of equol. Both equol and daidzein were characterized as monoglucuronide conjugates in human urine and the concentration of urinary equol exceeded the concentrations of the classical oestrogens by 100- to 1000-fold after ingestion of a single meal containing soya protein. The potential biological significance of this result is discussed.

Adult↗
PubMed1984

The oestrogenicity of equol in sheep.

The effects of intramuscular injection of synthetic racemic equol (+/- 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol) into wethers have been examined with respect to maintenance of plasma level, teat growth rate and the activity of the respiratory enzyme glucose-6-phosphate dehydrogenase. At a dose rate of 1.03 mmol/day a steady rise in 'total' (free plus conjugated) equol in plasma occurred to 1.78 mumol/l in 4 days. A dose rate of 2.07 mmol/day produced only a further slight increase in plasma equol. At a lower dose rate of 0.52 mmol/day the plasma concentration reached 0.62 mumol/l in 2 days and this was not exceeded thereafter. At the dose rate of 1.03 mmol/day over 7 days significant increases in teat length and glucose-6-phosphate dehydrogenase activity occurred but no significant changes were observed at the dose rate of 0.52 mmol/day. It appears that threshold levels of intake of equol which maintain a plasma level of about 1.65 mumol/l are needed for oestrogenic effects to become apparent within a relatively short time. Administration of 1.03 mmol/day over 5 days to ovariectomized ewes produced significant increases in uterine weight equivalent to those produced by 92 nmol stilboestrol dipropionate. Thus stilboestrol was apparently 56 000 times more potent than racemic equol.

Animals↗
PubMed2006

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

Equol, an isoflavonoid metabolite produced from the dietary isoflavone daidzein by the gut microflora in mammals, has been found to protect not only against ultraviolet (UV) radiation-induced cutaneous inflammation and photoimmune suppression, but also have antiphotocarcinogenic properties in mice. Because the state of DNA damage has been correlated with suppression of the immune system and photocarcinogenesis, we have therefore examined the potential of equol to offer protection from solar-simulated UV (SSUV) radiation-induced DNA damage in hairless mice by the immunohistochemical approach using monoclonal antibody specific for cyclobutane pyrimidine dimers (CPDs; H3 antibody). Topical application of 20 microM equol lotion, which was applied both before and after SSUV significantly reduced the number of CPDs. This reduction was evident immediately after SSUV exposure, at 1 h after exposure, and at 24 h after exposure, revealing 54%, 50%, and 26% reduction in CPDs, respectively. When the same concentration was applied for 5 consecutive days after SSUV exposure, there was no significant difference in the reduction of CPDs immediately after SSUV irradiation or at 1 hour afterwards, but there were significant reductions of 23% and 42% at 24 and 48 h after SSUV exposure, respectively. Despite apparently reducing the number of CPDs post-SSUV, topically applied equol did not appear to increase the rate of dimer removal. To conclude, equol applied topically prior to SSUV irradiation offers protection against CPD formation in hairless mice, possibly by acting as a suncreen and thus inhibiting DNA photodamage.

Administration, Topical↗
PubMed1987

Stimulation of breast cancer cells in vitro by the environmental estrogen enterolactone and the phytoestrogen equol.

The phenolic lignans enterolactone and enterodiol appear periodically in women's urine, dependent upon synthesis from plant-derived lignans by the intestinal microflora. The phytoestrogen equol is also present in women's urine, and is also derived from a vegetarian diet. Antiestrogenic or antiproliferative actions of these compounds have been postulated and related to the observation that there is a reduced incidence of breast cancer associated with diet. We evaluated the estrogenic and antiestrogenic activity of these compounds using four sensitive assays in tissue culture, including the use of human breast cancer cell lines T47D and MCF-7. Unexpectedly, we found that enterolactone and enterodiol, as well as equol, are weak estrogens, and that enterolactone and equol could stimulate the growth of estrogen-dependent breast cancer cell lines. We suggest that these environmental agents can promote the growth of breast cancer, particularly hormone-dependent metastases that may be located near the gut or in the mesenteries or liver, where the concentration of these intestinally produced compounds would be highest. Treatment with an antiestrogen such as tamoxifen blocks the estrogenic activity of these compounds. In the absence of treatment with an antiestrogen such as tamoxifen, hormonal therapy to block steroidal estrogen synthesis in a patient with breast cancer could conceivably be circumvented by a vegeterian diet rich in the precursors to estrogenic compounds such as enterolactone and equol.

4-Butyrolactone↗
PubMed2005

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

Using a method of high-performance liquid chromatography (HPLC) with coulometric array, we measured isoflavone levels in sera from seven volunteers before and after three days of ingesting Soyaflavone E (an isoflavones powder) and from 129 female farmers (Japanese Multiple Environmental Toxicants Study; JMETS). Results showed that the serum isoflavone concentrations rose dramatically after three days of ingesting Soyaflavone E in all subjects except for the serum equol concentrations in two subjects. The geometric mean concentrations of daidzein, genistein, and equol in the serum of 129 Japanese women were 25.0 ng/ml of daidzein, 94.1 ng/ml of genistein, and 9.6 ng/ml of equol. Interestingly, there existed two dominant groups in terms of serum equol concentrations in an independent manner of soy-derived product intake among the study participants.

Adult↗
PubMed2003

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

To explore the importance of equol on health outcomes in future studies, it was necessary to develop a method to reduce equol production. Female monkeys (n = 22) fed a soy diet were treated twice daily with vehicle (control; n = 4), doxycycline (2.5 mg/kg; n = 4), metronidazole (125 mg/d; n = 3), kanamycin (1000 mg/d; n = 4), vancomycin (100 mg/d; n = 3) or kanamycin+vancomycin (n = 4). Plasma samples were collected 4 h postfeeding at baseline, after 4 wk of treatment and 8 wk after the end of treatment and analyzed for isoflavonoid concentrations. Fecal swabs were collected at baseline and at the end of antibiotic treatment for analysis of Gram(+) and Gram(-) bacterial growth. Equol concentrations were reduced (P < 0.05) compared with baseline by 80, 93, 98 and 99% after treatment with metronidazole (955 +/- 164 vs. 193 +/- 53 nmol/L), kanamycin (545 +/- 211 vs. 37.1 +/- 17.6 nmol/L), vancomycin (607 +/- 163 vs. 8.9 +/- 8.2 nmol/L) and kanamycin+vancomycin (721 +/- 169 vs. 17.4 +/- 17.3 nmol/L), respectively. Daidzein concentrations were increased (P < 0.05) compared with baseline by treatment with doxycycline (336 +/- 87 vs. 576 +/- 76 nmol/L), kanamycin (168 +/- 67 vs. 374 +/- 15 nmol/L), and kanamycin+vancomycin (166 +/- 35 vs. 384 +/- 78 nmol/L). Similar increases (P < 0.05) in dihydrodaidzein were observed after treatment with kanamycin (31.2 +/- 6.2 vs. 479 +/- 188 nmol/L) and metronidazole (56.0 +/- 27.9 vs. 414 +/- 212 nmol/L). Isoflavonoid concentrations returned to baseline values after antibiotic treatment was terminated. Gram(+) bacterial growth was reduced by all treatments, including Control, compared with baseline. In conclusion, treatment with antibiotics resulted in a marked reduction in plasma equol concentrations and altered plasma isoflavonoid patterns in cynomolgus monkeys.

Administration, Oral↗
PubMed1975

Excretion of radioactive diadzein and equol as monosulfates and disulfates in the urine of the laying hen.

The phytoestrogen, diadzein, was injected intramuscularly as [4-14-C]daidzein into two laying hens. The radioactive materials in the urine for the succeeding 23 (hen 1) or 14 (hen 2) days were fractionated on a DEAE-Sephadex column by a gradient of NaCl and the fractions thus separated were further analyzed by solvent partition, susceptability to enzymic cleavage and thin-layer chromatography. The sic following components were identified and quantitated: [14-C]diadzein, [14-C]equol, [14-C]diadzein monosulfate, [14-C]equol monosulfate, [14-C]diazein disulfate, and [14-C]equol disulfate. The urine from hen 2 yielded also the sulfate of an unidentified conversion product of [14-C]daidzein. Repeared tests for glucuronides of [14-C]daidzein or its conversion products gave negative results, excluding the possibility that any appreciable proportion of the radioactivity in the urine was in the form of beta-glucuronide. It is concluded that the diadzein and the equol excretion in the urine of the laying hen are present for the most part as monosulfates and disulfates.

Animals↗
PubMed1998

Inhibition of mouse and human CYP 1A- and 2E1-dependent substrate metabolism by the isoflavonoids genistein and equol.

The inhibitory effect of the isoflavonoids genistein and equol on cytochrome P450 activities has been investigated. Genistein and equol inhibited the high capacity component of p-nitrophenol (CYP2E1 substrate) metabolism in liver microsomes from acetone-induced mice with IC50 values of approximately 10 mM and 560 microM, respectively (cf. diethyldithiocarbamate, IC50, 69 microM). Using human CYP2E1 from a specific expression system (which overcame multienzyme involvement in the rodent system), non-competitive inhibition was also seen with both isoflavonoids. Genistein and equol also inhibited the high capacity component of ethoxyresorufin (CYP1A substrate) metabolism in liver microsomes from beta-naphthoflavone-induced mice with IC50 values of 5.6 mM and 1.7 mM, respectively (cf. alpha-naphthoflavone, IC50 0.8 microM). Using human CYPIA2 from a specific expression system, noncompetitive inhibition was seen with both isoflavonoids. CYP1A1 inhibition offers a possible explanation for the chemopreventative effect of genistein against, for example, dimethylbenz[a]anthracene genotoxicity reported in animals but the IC50 values negate the relevance of this specific chemopreventative action at the levels likely to be achieved from the human diet.

Animals↗