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Shigeto Uchiyama - One of the best experts on this subject based on the ideXlab platform.

  • Relation between premenstrual syndrome and Equol-production status.
    The journal of obstetrics and gynaecology research, 2016
    Co-Authors: Takashi Takeda, Shigeto Uchiyama, Tomomi Ueno, Keizo Hiramatsu, Masami Shiina
    Abstract:

    Aim Consumption of isoflavones, which are predominantly derived from soybeans, reduces the risk of estrogen-related diseases, such as menopausal symptoms, breast cancer, osteoporosis, and cardiovascular disease. Equol is more bioavailable than other soy isoflavones, and Equol producers are believed to benefit to a greater extent. This study was conducted to evaluate the relation between premenstrual syndrome (PMS) and Equol-production status in Japanese reproductive-age women. Methods This was a cross-sectional, observational study. The study included 144 Japanese women aged 20–45 years. PMS patients (n = 46) were recruited at three obstetrics and gynecology clinics. Control group women (n = 98) who were not receiving therapy for PMS were recruited from the local area by advertisement. The participants’ Equol-production status was determined using urine samples collected after a soy challenge test. Results The prevalence of Equol producers was 41.8% in the control group and 23.9% in the patient group (P = 0.042). Using univariate analysis, significant risk factors for Equol non-producers were being a PMS patient and being younger. In multivariate analysis with a step-wise model, being a PMS patient (odds ratio, 2.342; 95% confidence interval, 1.021–5.698) was shown to be a significant risk factor for being an Equol non-producer. Conclusion This study showed a relation between PMS and Equol-production status in Japanese women.

  • a cross sectional study of Equol producer status and self reported vasomotor symptoms
    Menopause, 2015
    Co-Authors: Katherine M Newton, Shigeto Uchiyama, Tomomi Ueno, Susan D Reed, Soh Iwashita, Gabrielle Gunderson, Sharon Fuller, Johanna W Lampe
    Abstract:

    OBJECTIVE This study aims to evaluate the associations of vasomotor symptom (VMS) frequency, bother, and severity with Equol producer status and dietary daidzein intake. METHODS This is an observational study. This study included women aged 45 to 55 years, in postmenopause or in the menopausal transition, who had soy food intake of three or more servings per week. Exclusion criteria included severe concurrent disease, pregnancy or planned pregnancy, and current use of oral or transdermal hormones or selective estrogen receptor modulators. After screening, 375 participants completed a 3-day VMS diary and a 24-hour urine collection. Women with a urine daidzein or genistein concentration of 100 ng/mL or higher were included. We evaluated the association of VMS--dichotomized as lower than or equal to versus higher than the mean number of VMS per day (<2.33, ≥ 2.33)--with quartiles of daidzein intake. RESULTS Overall, 129 (35%) of 365 women were Equol producers. The mean (SD) urinary Equol excretion was 0.67 (1.57) mg/day (50th percentile, 0 mg/d; 95th percentile, 4.12 mg/d). Among Equol producers, the mean (SD) urinary Equol excretion was 1.91 (2.15) mg/day (50th percentile, 1.09 mg/d; 95th percentile, 6.27 mg/d). Among Equol producers, compared with those in the lowest quartile of dietary daidzein intake (mean, 4.9 mg/d), those in the highest quartile (mean, 28.5 mg/d) were 76% less likely to have VMS higher than the mean number of VMS (odds ratio, 0.24; 95% CI, 0.07-0.83; trend test across all daidzein levels, P = 0.06). Among Equol nonproducers, there were no associations between daidzein intake and VMS frequency. There were no differences in VMS bother or severity among Equol producers or nonproducers by dietary daidzein level. CONCLUSIONS Among Equol producers, higher Equol availability attributable to higher soy consumption contributes to decreased VMS.

  • Effects of natural S-Equol supplements on overweight or obesity and metabolic syndrome in the Japanese, based on sex and Equol status.
    Clinical endocrinology, 2013
    Co-Authors: Takeshi Usui, Tomomi Ueno, Mayu Tochiya, Yousuke Sasaki, Kazuya Muranaka, Hajime Yamakage, Akihiro Himeno, Akira Shimatsu, Asami Inaguma, Shigeto Uchiyama
    Abstract:

    SummaryObjectives Epidemiologic studies indicate that soy intake has an important role in the prevention of age-related health problems. Daidzein, the principal isoflavone contained in soy, is converted to S-Equol by the intestinal bacteria. Not all individuals, however, can produce S-Equol, which is considered the most biologically active metabolite. We studied the effects of a natural S-Equol supplement on metabolic parameters associated with overweight or obesity and metabolic syndrome. Methods The study was a randomized, double-blinded, placebo-controlled, crossover design with no washout period. All subjects were considered overweight or obese if they had a body mass index ≧25 kg/m2. Placebo or natural S-Equol tablets containing 10 mg S-Equol were orally ingested each day for 12 weeks. A total of 54 Japanese overweight or obese outpatients were enrolled. The Equol phenotype was determined, and various metabolic parameters, including cardio-ankle vascular index (CAVI), were measured. Results Equol non-producers comprised 67·9% of the overweight or obese subjects. The ratio of Equol non-producers in this overweight or obese subject group was higher than the previously reported ratio of Equol non-producers (approximately 50%) in the general population. Compared with the placebo group, intervention with natural S-Equol led to a significant decrease in HbA1c, serum low-density lipoprotein cholesterol (LDL-C) levels and CAVI score. Furthermore, the effect was more prominent in the subgroup of female Equol non-producers. Conclusion The ratio of Equol non-producers in overweight or obese populations might be higher than generally reported. Natural S-Equol might have a role in glycaemic control and in the prevention of cardiovascular disease by its effects to lower LDL-C levels and CAVI scores in overweight or obese individuals.

  • discovery of an s Equol rich food stinky tofu a traditional fermented soy product in taiwan
    International Journal of Food Sciences and Nutrition, 2012
    Co-Authors: Yasuhiro Abiru, Shigeto Uchiyama, Tomomi Ueno, Megumi Kumemura, Kyosuke Masaki
    Abstract:

    A recent epidemiological study showed that daily intake of mg quantities of S-Equol is required for health-promoting effects in menopausal women. However, the maximum Equol content in food was reported to be approximately 130 μg/100 g in egg yolk. The objective of this study was to find a high Equol-containing food. We measured the Equol content of 33 egg yolks and 21 fermented soybean foods. Equol was detected in 28 egg yolks at the maximum content of 43 μg/100 g. In the fermented soybean foods, Equol was detected only in stinky tofu. We examined 16 stinky tofu samples purchased during different seasons and the average Equol content was 1.39 mg/100 g, ranging from 0.34 to 2.68 mg/100 g. Equol was present in stinky tofu as the S-enantiomeric form and as an aglycon type. This is the first report demonstrating that stinky tofu contains high levels of S-Equol, which may exert beneficial effects in menopausal women.

  • identification of a novel dihydrodaidzein racemase essential for biosynthesis of Equol from daidzein in lactococcus sp strain 20 92
    Applied and Environmental Microbiology, 2012
    Co-Authors: Yoshikazu Shimada, Masayuki Takahashi, Norihiro Miyazawa, Yasuhiro Abiru, Shigeto Uchiyama, Haretsugu Hishigaki
    Abstract:

    Equol is metabolized from daidzein, a soy isoflavone, by the gut microflora. In this study, we identified a novel dihydrodaidzein racemase (l-DDRC) that is involved in Equol biosynthesis in a lactic acid bacterium, Lactococcus sp. strain 20-92, and confirmed that histidine-tagged recombinant l-DDRC (l-DDRC-His) was able to convert both the (R)- and (S)-enantiomers of dihydrodaidzein to the racemate. Moreover, we showed that recombinant l-DDRC-His was essential for in vitro Equol production from daidzein by a recombinant enzyme mixture and that efficient in vitro Equol production from daidzein was possible using at least four enzymes, including l-DDRC. We also proposed a model of the metabolic pathway from daidzein to Equol in Lactococcus strain 20-92.

Tomomi Ueno - One of the best experts on this subject based on the ideXlab platform.

  • Relation between premenstrual syndrome and Equol-production status.
    The journal of obstetrics and gynaecology research, 2016
    Co-Authors: Takashi Takeda, Shigeto Uchiyama, Tomomi Ueno, Keizo Hiramatsu, Masami Shiina
    Abstract:

    Aim Consumption of isoflavones, which are predominantly derived from soybeans, reduces the risk of estrogen-related diseases, such as menopausal symptoms, breast cancer, osteoporosis, and cardiovascular disease. Equol is more bioavailable than other soy isoflavones, and Equol producers are believed to benefit to a greater extent. This study was conducted to evaluate the relation between premenstrual syndrome (PMS) and Equol-production status in Japanese reproductive-age women. Methods This was a cross-sectional, observational study. The study included 144 Japanese women aged 20–45 years. PMS patients (n = 46) were recruited at three obstetrics and gynecology clinics. Control group women (n = 98) who were not receiving therapy for PMS were recruited from the local area by advertisement. The participants’ Equol-production status was determined using urine samples collected after a soy challenge test. Results The prevalence of Equol producers was 41.8% in the control group and 23.9% in the patient group (P = 0.042). Using univariate analysis, significant risk factors for Equol non-producers were being a PMS patient and being younger. In multivariate analysis with a step-wise model, being a PMS patient (odds ratio, 2.342; 95% confidence interval, 1.021–5.698) was shown to be a significant risk factor for being an Equol non-producer. Conclusion This study showed a relation between PMS and Equol-production status in Japanese women.

  • a cross sectional study of Equol producer status and self reported vasomotor symptoms
    Menopause, 2015
    Co-Authors: Katherine M Newton, Shigeto Uchiyama, Tomomi Ueno, Susan D Reed, Soh Iwashita, Gabrielle Gunderson, Sharon Fuller, Johanna W Lampe
    Abstract:

    OBJECTIVE This study aims to evaluate the associations of vasomotor symptom (VMS) frequency, bother, and severity with Equol producer status and dietary daidzein intake. METHODS This is an observational study. This study included women aged 45 to 55 years, in postmenopause or in the menopausal transition, who had soy food intake of three or more servings per week. Exclusion criteria included severe concurrent disease, pregnancy or planned pregnancy, and current use of oral or transdermal hormones or selective estrogen receptor modulators. After screening, 375 participants completed a 3-day VMS diary and a 24-hour urine collection. Women with a urine daidzein or genistein concentration of 100 ng/mL or higher were included. We evaluated the association of VMS--dichotomized as lower than or equal to versus higher than the mean number of VMS per day (<2.33, ≥ 2.33)--with quartiles of daidzein intake. RESULTS Overall, 129 (35%) of 365 women were Equol producers. The mean (SD) urinary Equol excretion was 0.67 (1.57) mg/day (50th percentile, 0 mg/d; 95th percentile, 4.12 mg/d). Among Equol producers, the mean (SD) urinary Equol excretion was 1.91 (2.15) mg/day (50th percentile, 1.09 mg/d; 95th percentile, 6.27 mg/d). Among Equol producers, compared with those in the lowest quartile of dietary daidzein intake (mean, 4.9 mg/d), those in the highest quartile (mean, 28.5 mg/d) were 76% less likely to have VMS higher than the mean number of VMS (odds ratio, 0.24; 95% CI, 0.07-0.83; trend test across all daidzein levels, P = 0.06). Among Equol nonproducers, there were no associations between daidzein intake and VMS frequency. There were no differences in VMS bother or severity among Equol producers or nonproducers by dietary daidzein level. CONCLUSIONS Among Equol producers, higher Equol availability attributable to higher soy consumption contributes to decreased VMS.

  • Effects of natural S-Equol supplements on overweight or obesity and metabolic syndrome in the Japanese, based on sex and Equol status.
    Clinical endocrinology, 2013
    Co-Authors: Takeshi Usui, Tomomi Ueno, Mayu Tochiya, Yousuke Sasaki, Kazuya Muranaka, Hajime Yamakage, Akihiro Himeno, Akira Shimatsu, Asami Inaguma, Shigeto Uchiyama
    Abstract:

    SummaryObjectives Epidemiologic studies indicate that soy intake has an important role in the prevention of age-related health problems. Daidzein, the principal isoflavone contained in soy, is converted to S-Equol by the intestinal bacteria. Not all individuals, however, can produce S-Equol, which is considered the most biologically active metabolite. We studied the effects of a natural S-Equol supplement on metabolic parameters associated with overweight or obesity and metabolic syndrome. Methods The study was a randomized, double-blinded, placebo-controlled, crossover design with no washout period. All subjects were considered overweight or obese if they had a body mass index ≧25 kg/m2. Placebo or natural S-Equol tablets containing 10 mg S-Equol were orally ingested each day for 12 weeks. A total of 54 Japanese overweight or obese outpatients were enrolled. The Equol phenotype was determined, and various metabolic parameters, including cardio-ankle vascular index (CAVI), were measured. Results Equol non-producers comprised 67·9% of the overweight or obese subjects. The ratio of Equol non-producers in this overweight or obese subject group was higher than the previously reported ratio of Equol non-producers (approximately 50%) in the general population. Compared with the placebo group, intervention with natural S-Equol led to a significant decrease in HbA1c, serum low-density lipoprotein cholesterol (LDL-C) levels and CAVI score. Furthermore, the effect was more prominent in the subgroup of female Equol non-producers. Conclusion The ratio of Equol non-producers in overweight or obese populations might be higher than generally reported. Natural S-Equol might have a role in glycaemic control and in the prevention of cardiovascular disease by its effects to lower LDL-C levels and CAVI scores in overweight or obese individuals.

  • discovery of an s Equol rich food stinky tofu a traditional fermented soy product in taiwan
    International Journal of Food Sciences and Nutrition, 2012
    Co-Authors: Yasuhiro Abiru, Shigeto Uchiyama, Tomomi Ueno, Megumi Kumemura, Kyosuke Masaki
    Abstract:

    A recent epidemiological study showed that daily intake of mg quantities of S-Equol is required for health-promoting effects in menopausal women. However, the maximum Equol content in food was reported to be approximately 130 μg/100 g in egg yolk. The objective of this study was to find a high Equol-containing food. We measured the Equol content of 33 egg yolks and 21 fermented soybean foods. Equol was detected in 28 egg yolks at the maximum content of 43 μg/100 g. In the fermented soybean foods, Equol was detected only in stinky tofu. We examined 16 stinky tofu samples purchased during different seasons and the average Equol content was 1.39 mg/100 g, ranging from 0.34 to 2.68 mg/100 g. Equol was present in stinky tofu as the S-enantiomeric form and as an aglycon type. This is the first report demonstrating that stinky tofu contains high levels of S-Equol, which may exert beneficial effects in menopausal women.

  • s Equol and the fermented soy product se5 oh containing s Equol similarly decrease ovariectomy induced increase in rat tail skin temperature in an animal model of hot flushes
    Menopause, 2011
    Co-Authors: Takeshi Yoneda, Tomomi Ueno, Shigeto Uchiyama
    Abstract:

    Objective The aim of this study was to compare the effect of SE5-OH, a fermented soy product containing S-Equol, with purified S-Equol on hot flushes in an ovariectomized rat model. Methods Eleven-week-old female Sprague-Dawley rats were assigned to either the sham group (vehicle; n = 30) or one of four ovariectomized groups: control (vehicle; n = 30), conjugated equine estrogens (CEE; 6.0 mg kg(-1) d(-1) CEE; n = 10), SE5-OH (2,000 mg kg(-1) d(-1) SE5-OH containing 11.7 mg kg(-1) d(-1) as S-Equol; n = 30), and S-Equol (11.7 mg kg(-1) d(_1) S-Equol; n = 30). Three days after sham operation or ovariectomy, animals were treated once daily for 38 days. Tail skin temperature (TST) was assessed on days 21, 28, and 35 after surgery. Plasma estradiol and follicle-stimulating hormone levels and uterine weight and uteri histology were evaluated at the end of treatment. Results The rise in TST resulting from ovariectomy was inhibited by CEE, SE5-OH, and S-Equol. Compared with the control, TST was decreased by 68.9% and 86.2% in SE5-OH group on days 21 and 28, respectively (P = 0.014, 0.020), and by 60.1% and 89.1% in S-Equol group, respectively (P = 0.038, 0.016). Unlike in the CEE group, plasma estradiol and follicle-stimulating hormone levels, uterine weight, epithelial height, stromal expansion, and myometrial thickness were not affected in SE5-OH and S-Equol groups. Conclusions The results of this animal model of hot flushes suggest that S-Equol is one of the primary components of SE5-OH and that both SE5-OH and S-Equol represent promising alternatives for the treatment of menopausal symptoms. Clinical research is needed to confirm these findings.

Edwin D. Lephart - One of the best experts on this subject based on the ideXlab platform.

  • biochemical investigation and gene analysis of Equol a plant and soy derived isoflavonoid with antiaging and antioxidant properties with potential human skin applications
    Biofactors, 2012
    Co-Authors: Remona Gopaul, Helen Knaggs, Edwin D. Lephart
    Abstract:

    The purpose of this study was to investigate the effects of Equol, a plant and intestinal flora derived isoflavonoid molecule on the expression of skin genes and proteins using human dermal models. As Equol has been shown to mimic 17β-estradiol and bind specifically to 5α-dihydrotestostone (5α-DHT), these agents were used (in addition to Equol) to determine whether Equol may play important and beneficial roles in the extracellular matrix (ECM). Equol at 0.3 or 1.2% in qPCR experiments using a human skin barrier model examined ECM gene expression. Equol, 5α-DHT, and 17β-estradiol at 10 nM were studied in human monolayer fibroblasts cultures (hMFC) for ECM protein expression. Human fibroblast three-dimensional organotypic cultures revealed Equol's influence (@ 10 nM) on ECM proteins via fluorescent-activated cell sorting (FACS) analysis. In qPCR experiments, Equol significantly increased collagen, elastin (ELN), and tissue inhibitor of metalloprotease and decreased metalloproteinases (MMPs) gene expression and caused significant positive changes in skin antioxidant and antiaging genes. In hMFC, Equol significantly increased collagen type I (COL1A1), whereas, 5α-DHT significantly decreased cell viability that was blocked by Equol. FACS analysis showed Equol and 17β-estradiol significantly stimulated COL1A1, collagen type III (COL3A1), and ELN while MMPs were significantly decreased compared with control values. Finally, tamoxifen blocked the positive influences of Equol on ECM proteins via FACS analysis. These findings suggest that Equol has the potential to be used topically for the treatment and prevention of skin aging, by enhancing ECM components in human skin.

  • Equol an isoflavonoid potential for improved prostate health in vitro and in vivo evidence
    Reproductive Biology and Endocrinology, 2011
    Co-Authors: Trent D Lund, Crystal Blake, Amy Hamaker, Edwin D. Lephart
    Abstract:

    Background: To determine: in vitro binding affinity of Equol for 5alpha-dihydrotestosterone (5alpha-DHT), in vitro effects of Equol treatment in human prostate cancer (LNCap) cells, and in vivo effects of Equol on rat prostate weight and circulating levels of sex steroid hormones. Methods: First, in vitro Equol binding affinity for 5alpha-DHT was determined using 14C5alpha-DHT combined with cold 5alpha-DHT (3.0 nM in all samples). These steroids were incubated with increasing concentrations of Equol (02,000 nM) and analyzed by Sephadex LH-20 column chromatography. 14C5alpha-DHT peak/profiles were determined by scintillation counting of column fractions. Using the 14C5alpha-DHT peak (0 nM Equol) as a reference standard, a binding curve was generated by quantifying shifts in the 14C5alpha-DHT peaks as Equol concentrations increased. Second, Equol’s in vitro effects on LNCap cells were determined by culturing cells (48 hours) in the presence of increasing concentrations of dimethyl sulfoxide (DMSO) (vehicle-control), 5alpha-DHT, Equol or 5alpha-DHT+Equol. Following culture, prostate specific antigen (PSA) levels were quantified via ELISA. Finally, the in vivo effects of Equol were tested in sixteen male Long-Evans rats fed a low isoflavone diet. From 190215 days, animals received 0.1cc s.c. injections of either DMSO-control vehicle (n = 8) or 1.0 mg/kg (body weight) of Equol (in DMSO) (n = 8). At 215 days, body and prostate weights were recorded, trunk blood was collected and serum assayed for luteinizing hormone (LH), 5alpha-DHT, testosterone and 17beta-estradiol levels. Results: Maximum and half maximal Equol binding to 5alpha-DHT occurred at approximately 100 nM and 4.8 nM respectively. LNCap cells cultured in the presence of 5alpha-DHT significantly increased PSA levels. However, in the presence of 5alpha-DHT+Equol, Equol blocked the significant increases in PSA levels from LNCap cells. In vivo Equol treatment significantly decreased rat prostate weights and serum 5alpha-DHT levels but did not alter LH, testosterone, and estradiol levels. Conclusions: Equol administration appears to have potential beneficial effects for prostate health and other 5alpha-DHT mediated disorders. Equol administration: reduces PSA levels from LNCap cells under 5alpha-DHT stimulation, decreases rat prostate size, decreases serum 5alpha-DHT levels and androgen hormone action, while not altering other circulating sex steroids or LH levels.

  • Equol an isoflavonoid potential for improved prostate health in vitro and in vivo evidence
    Reproductive Biology and Endocrinology, 2011
    Co-Authors: Trent D Lund, Crystal Blake, Amy Hamaker, Edwin D. Lephart
    Abstract:

    Background To determine: in vitro binding affinity of Equol for 5alpha-dihydrotestosterone (5alpha-DHT), in vitro effects of Equol treatment in human prostate cancer (LNCap) cells, and in vivo effects of Equol on rat prostate weight and circulating levels of sex steroid hormones.

  • s Equol a potent ligand for estrogen receptor β is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora
    The American Journal of Clinical Nutrition, 2005
    Co-Authors: Kenneth D. R. Setchell, Edwin D. Lephart, Nadine M Brown, Sidney John Cole, Carlo Alfredo Clerici, Claire Heenan, Danilo Castellani, Brian Wolfe, Linda Nechemiaszimmer, Trent D Lund
    Abstract:

    BACKGROUND The discovery of Equol in human urine more than 2 decades ago and the finding that it is bacterially derived from daidzin, an isoflavone abundant in soy foods, led to the current nutritional interest in soy foods. Equol, unlike the soy isoflavones daidzein or genistein, has a chiral center and therefore can occur as 2 distinct diastereoisomers. OBJECTIVE Because it was unclear which enantiomer was present in humans, our objectives were to characterize the exact structure of Equol, to examine whether the S- and R-Equol enantiomers are bioavailable, and to ascertain whether the differences in their conformational structure translate to significant differences in affinity for estrogen receptors. DESIGN With the use of chiral-phase HPLC and mass spectrometry, Equol was isolated from human urine and plasma, and its enantiomeric structure was defined. Human fecal flora were cultured in vitro and incubated with daidzein to ascertain the stereospecificity of the bacterial production of Equol. The pharmacokinetics of S- and R- Equol were determined in 3 healthy adults after single-bolus oral administration of both enantiomers, and the affinity of each Equol enantiomer for estrogen receptors was measured. RESULTS Our studies definitively establish S-Equol as the exclusive product of human intestinal bacterial synthesis from soy isoflavones and also show that both enantiomers are bioavailable. S-Equol has a high affinity for estrogen receptor beta (K(i) = 0.73 nmol/L), whereas R-Equol is relatively inactive. CONCLUSIONS Humans have acquired an ability to exclusively synthesize S-Equol from the precursor soy isoflavone daidzein, and it is significant that, unlike R-Equol, this enantiomer has a relatively high affinity for estrogen receptor beta.

  • Equol is a novel anti androgen that inhibits prostate growth and hormone feedback
    Biology of Reproduction, 2004
    Co-Authors: Trent D Lund, Edwin D. Lephart, Kenneth D. R. Setchell, Daniel J Munson, Megan E Haldy, Robert J Handa
    Abstract:

    Equol (7-hydroxy-3[49hydroxyphenyl]-chroman) is the major metabolite of the phytoestrogen daidzein, one of the main isoflavones found abundantly in soybeans and soy foods. Equol may be an important biologically active molecule based on recent studies demonstrating that Equol can modulate reproductive function. In this study, we examined the effects of Equol on prostate growth and LH secretion and determined some of the mechanisms by which it might act. Administration of Equol to intact male rats for 4‐7 days reduced ventral prostate and epididymal weight and increased circulating LH levels. Using binding assays, we determined that Equol specifically binds 5a-dihydrotestosterone (DHT), but not testosterone, dehydroepiandrosterone, or estrogen with high affinity. Equol does not bind the prostatic androgen receptor, and has a modest affinity for recombinant estrogen receptor (ER) b, and no affinity for ERa. In castrated male rats treated with DHT, concomitant treatment with Equol blocked DHT’s trophic effects on the ventral prostate gland growth and inhibitory feedback effects on plasma LH levels without changes in circulating DHT. Therefore, Equol can bind circulating DHT and sequester it from the androgen receptor, thus altering growth and physiological hormone responses that are regulated by androgens. These data suggest a novel model to explain Equol’s biological properties. The significance of Equol’s ability to specifically bind and sequester DHT from the androgen receptor have important ramifications in health and disease and may indicate a broad and important usage for Equol in the treatment of androgen-mediated pathologies. androgen receptor, epididymis, prostate, steroid hormones, testosterone

Kenneth D. R. Setchell - One of the best experts on this subject based on the ideXlab platform.

  • Dietary Factors Influence Production of the Soy Isoflavone Metabolite S-(-)Equol in Healthy Adults
    The Journal of nutrition, 2013
    Co-Authors: Kenneth D. R. Setchell, James E Heubi, Nadine M Brown, Suzanne S. Summer, Eileen C. King, Sidney John Cole, Trish Guy, Bevan Hokin
    Abstract:

    S-(-)Equol, an intestinally derived metabolite of the soy isoflavone daidzein, is proposed to enhance the efficacy of soy diets. Adults differ in their ability to produce Equol when consuming soy foods for reasons that remain unclear. Therefore, we performed a comprehensive dietary analysis of 143 macro- and micronutrients in 159 healthy adults in the United States (n = 89) and Australia (n = 70) to determine whether the intake of specific nutrients favors Equol production. Three-d diet records were collected and analyzed using Nutrition Data System for Research software and S-(-)Equol was measured in urine by mass spectrometry. Additionally, in a subset of Equol producers and nonproducers (n = 10/group), we examined the long-term stability of Equol producer status by retesting 12, 18, and 24 mo later. Finally, the effect of oral administration of the antibiotic metronidazole (500 mg/d for 7 d) on Equol production was examined in 5 adults monitored during a 4-mo follow-up period. Equol producers accounted for 30.3% and 28.6% of the United States and Australian participants, respectively (overall frequency, 29.6%). No significant differences were observed for total protein, carbohydrate, fat, saturated fat, or fiber intakes between Equol producers and nonproducers. However, principal component analysis revealed differences in several nutrients, including higher intakes of polyunsaturated fatty acids (P = 0.039), maltose (P = 0.02), and vitamins A (P = 0.01) and E (P = 0.035) and a lower intake of total cholesterol (P = 0.010) in Equol producers. During a 2-y period, Equol producer status remained unchanged in all nonproducers and in 80% of Equol producers, whereas metronidazole abolished Equol production in only 20% of participants. In conclusion, these findings suggest that major differences in the macronutrient content of the diet appear not to influence Equol production, but subtle differences in some nutrients may influence the ability to produce Equol, which was a relatively stable phenomenon.

  • Equol history chemistry and formation
    Journal of Nutrition, 2010
    Co-Authors: Kenneth D. R. Setchell, Carlo Alfredo Clerici
    Abstract:

    Equol, first isolated from equine urine in 1932 and identified 50 years later in human urine as a metabolite of the soy isoflavones, daidzin and daidzein, is produced by intestinal bacteria in some, but not all, adults. This observation led to the term Equol-producers to define those adults that could make Equol in response to consuming soy isoflavones and the hypothesis that the health benefits of soy-based diets may be greater in Equol-producers than in Equol nonproducers. By virtue of a chiral center, Equol occurs as a diastereoisomer and intestinal bacteria are enantiospecific in synthesizing exclusively the S-(-)Equol enantiomer, an enantiomer that has selective affinity for the estrogen receptor-β. Both enantiomers are of interest from a clinical and pharmacological perspective and are currently being developed as nutraceutical and pharmacological agents. The wide range of biological activities these enantiomers possess warrants their investigation for the treatment of a number of hormone-related conditions involving estrogen-dependent and androgen-related conditions. The following review describes the history, chemistry, and factors governing the intestinal bacterial formation of Equol.

  • Equol: Pharmacokinetics and Biological Actions
    The Journal of nutrition, 2010
    Co-Authors: Kenneth D. R. Setchell, Carlo Alfredo Clerici
    Abstract:

    Equol [7-hydroxy-3-(4'-hydroxyphenyl)-chroman], an isoflavan produced by intestinal bacteria in response to soy isoflavone intake in some but not all humans, exhibits a wide range of biological properties. It exists as the diastereoisomers S-(-) Equol and R-(+)Equol. Intestinal bacteria produce exclusively S-(-)Equol, which has selective affinity for estrogen receptor (ER)-β- The evidence is conflicting on whether there is an advantage to producing S-(-)Equol in response to soy isoflavone intakes, but the ability to now synthesize these diastereoisomers opens the way for future clinical trials to directly examine their potential in a number of hormone-dependent conditions. In this review, the plasma and urinary pharmacokinetics of S-(-)Equol and R-(+)Equol are reviewed and summarized, and some of the more recent evidence supporting potential biological effects of S-(-)Equol is considered.

  • 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
    The American Journal of Clinical Nutrition, 2009
    Co-Authors: Kenneth D. R. Setchell, Xueheng Zhao, James E Heubi, Nadine M Brown
    Abstract:

    Background: The nonsteroidal estrogen Equol occurs as diastereoisomers, S-(−)Equol and R-(+)Equol, both of which have significant biological actions. S-(−)Equol, the naturally occurring enantiomer produced by 20–30% of adults consuming soy foods, has selective affinity for estrogen receptor-β, whereas both enantiomers modulate androgen action. Little is known about the pharmacokinetics of the diastereoisomers, despite current interest in developing Equol as a nutraceutical or pharmaceutical agent. Objective: The objective was to compare the pharmacokinetics of S-(−)Equol and R-(+)Equol by using [13C] stable-isotope-labeled tracers to facilitate the optimization of clinical studies aimed at evaluating the potential of these diastereoisomers in the prevention and treatment of estrogen- and androgen-dependent conditions. Design: A randomized, crossover, open-label study in 12 healthy adults (6 men and 6 women) compared the plasma and urinary pharmacokinetics of orally administered enantiomeric pure forms of S-(−)[2-13C]Equol, R-(+)[2-13C]Equol, and the racemic mixture. Plasma and urinary [13C]R-Equol and [13C]S-Equol concentrations were measured by tandem mass spectrometry. Results: Plasma [13C]Equol concentration appearance and disappearance curves showed that both enantiomers were rapidly absorbed, attained high circulating concentrations, and had a similar terminal elimination half-life of 7–8 h. The systemic bioavailability and fractional absorption of R-(+)[2-13C]Equol were higher than those of S-(−)[2-13C]Equol or the racemate. The pharmacokinetics of racemic (±)[2-13C]Equol were different from those of the individual enantiomers: slower absorption, lower peak plasma concentrations, and lower systemic bioavailability. Conclusions: The high bioavailability of both diastereoisomers contrasts with previous findings for the soy isoflavones daidzein and genistein, both of which have relatively poor bioavailability, and suggests that low doses of Equol taken twice daily may be sufficient to achieve biological effects.

  • The Pharmacokinetics of S-(-)Equol Administered as SE5-OH Tablets to Healthy Postmenopausal Women
    The Journal of nutrition, 2009
    Co-Authors: Kenneth D. R. Setchell, Xueheng Zhao, Susan E. Shoaf, Karen Ragland
    Abstract:

    The soy isoflavone metabolite, S-(-)Equol, has selective affinity for estrogen receptor (ER)beta and also antagonizes in vivo the action of dihydrotestosterone. It is therefore of interest as a potential new therapeutic agent in hormone-dependent conditions and is under development as a nutraceutical. Our objective in this study was to define the pharmacokinetics of natural S-(-)Equol after administration of SE5-OH, a newly developed S-(-)Equol supplement made by incubation of the Equol-producing bacterium Lactococcus garvieae with soy germ isoflavones. In a single-center, open-label, randomized, 2-period crossover design study, the pharmacokinetics of S-(-)Equol administered as single-bolus oral doses of 10 and 30 mg in the form of SE5-OH tablets was determined in 12 healthy postmenopausal women. S-(-)Equol was measured in plasma and urine collected at timed intervals over a 48-h period postdosing using tandem MS. Equol-producer status was also determined after a soymilk challenge conducted after the pharmacokinetic sampling was complete. S-(-)Equol was rapidly absorbed after oral administration and attained high plasma concentrations, with a plasma elimination half-life of 8 h. The maximum plasma concentration/dose, area under the plasma concentration-time curve from time 0 to infinity/dose, and the fraction of dose excreted in urine (%f(e,u)) were similar for the 2 doses, indicating a dose-proportional response in total S-(-)Equol pharmacokinetics. The systemic bioavailability of S-(-)Equol was very high, as the %f(e,u) was 82% for both doses, which is greater than published data for the soy isoflavones daidzein and genistein. Three participants were determined to be Equol-producers, representing a 25% frequency, and Equol-producer status had no effect on natural S-(-)Equol pharmacokinetics.

Johanna W Lampe - One of the best experts on this subject based on the ideXlab platform.

  • a cross sectional study of Equol producer status and self reported vasomotor symptoms
    Menopause, 2015
    Co-Authors: Katherine M Newton, Shigeto Uchiyama, Tomomi Ueno, Susan D Reed, Soh Iwashita, Gabrielle Gunderson, Sharon Fuller, Johanna W Lampe
    Abstract:

    OBJECTIVE This study aims to evaluate the associations of vasomotor symptom (VMS) frequency, bother, and severity with Equol producer status and dietary daidzein intake. METHODS This is an observational study. This study included women aged 45 to 55 years, in postmenopause or in the menopausal transition, who had soy food intake of three or more servings per week. Exclusion criteria included severe concurrent disease, pregnancy or planned pregnancy, and current use of oral or transdermal hormones or selective estrogen receptor modulators. After screening, 375 participants completed a 3-day VMS diary and a 24-hour urine collection. Women with a urine daidzein or genistein concentration of 100 ng/mL or higher were included. We evaluated the association of VMS--dichotomized as lower than or equal to versus higher than the mean number of VMS per day (<2.33, ≥ 2.33)--with quartiles of daidzein intake. RESULTS Overall, 129 (35%) of 365 women were Equol producers. The mean (SD) urinary Equol excretion was 0.67 (1.57) mg/day (50th percentile, 0 mg/d; 95th percentile, 4.12 mg/d). Among Equol producers, the mean (SD) urinary Equol excretion was 1.91 (2.15) mg/day (50th percentile, 1.09 mg/d; 95th percentile, 6.27 mg/d). Among Equol producers, compared with those in the lowest quartile of dietary daidzein intake (mean, 4.9 mg/d), those in the highest quartile (mean, 28.5 mg/d) were 76% less likely to have VMS higher than the mean number of VMS (odds ratio, 0.24; 95% CI, 0.07-0.83; trend test across all daidzein levels, P = 0.06). Among Equol nonproducers, there were no associations between daidzein intake and VMS frequency. There were no differences in VMS bother or severity among Equol producers or nonproducers by dietary daidzein level. CONCLUSIONS Among Equol producers, higher Equol availability attributable to higher soy consumption contributes to decreased VMS.

  • is Equol the key to the efficacy of soy foods
    The American Journal of Clinical Nutrition, 2009
    Co-Authors: Johanna W Lampe
    Abstract:

    Gut bacterial modification of soy isoflavones produces metabolites that differ in biological activity from the parent compounds. Hydrolysis of glycosides results in more active compounds. In contrast, further degradation and transformation of aglycones produce more or less active compounds, depending on the substrate metabolized and the product formed. Bacterial metabolism of soy isoflavones varies among individuals. The predominant daidzein metabolites produced by human intestinal bacteria are Equol and O-desmethylangolensin. Among humans, 30-50% have the bacteria capable of producing Equol and 80-90% harbor O-desmethylangolensin-producing bacteria. Factors that influence the capacity to produce Equol and O-desmethylangolensin are not clearly established; however, gut physiology, host genetics, and diet are reported to contribute to interindividual differences in conversion of daidzein to Equol. Effects of these phenotypes on human health are poorly characterized. Some studies in high soy-consuming populations reported an inverse association between urinary and serum Equol concentrations and breast and prostate cancer risk. Furthermore, several studies of soy supplementation and bone density suggest that soy products may be more effective in maintaining bone density in Equol-producing individuals. Factors that contribute to the phenotypes and the relation of these specific phenotypes to human health need to be further elucidated. The extent to which isoflavone metabolism is key to the efficacy of soy foods remains to be established.

  • in vitro incubation of human feces with daidzein and antibiotics suggests interindividual differences in the bacteria responsible for Equol production
    Journal of Nutrition, 2004
    Co-Authors: Charlotte Atkinson, Sheryl H Berman, Olivier Humbert, Johanna W Lampe
    Abstract:

    Daidzein can be metabolized to Equol, dihydrodaidzein (DHD), and O-desmethylangolensin (ODMA) by intestinal bacteria. Only one third to one half of individuals produce Equol, and evidence exists to support potential cancer-protective effects of Equol production. We investigated the in vitro metabolism of daidzein by fecal bacteria and assessed the effect of several antibiotics on metabolism. Fresh or previously frozen feces from 7 Equol producers and 6 nonproducers were incubated with daidzein, with or without antibiotics, for 5 d at 37 degrees C. With the exception of one previously frozen sample, fecal inoculates from Equol producers converted daidzein to Equol. Conversion occurred under anaerobic, but not aerobic conditions. Fecal inoculates from Equol nonproducers did not produce Equol, but some produced ODMA and DHD. Between-subject differences in the effects of antibiotics on daidzein metabolism were apparent. Some antibiotics inhibited the production of Equol but had no effect on DHD production. These results suggest that several bacteria may be involved in daidzein metabolism, and that they may differ among subjects. This simple in vitro system can facilitate the study of factors influencing Equol production and minimize the need for animal models or human interventions. Furthermore, these analyses can be conducted on fecal samples that have been frozen and stored.

  • wheat bran and soy protein feeding do not alter urinary excretion of the isoflavan Equol in premenopausal women
    Journal of Nutrition, 2001
    Co-Authors: Johanna W Lampe, Kristiina Wähälä, Heather E Skor, William N Howald, Chu Chen
    Abstract:

    The capacity to convert the soy isoflavone daidzein to Equol in vivo is presumably determined by an individual's intestinal microfloral populations; however, diet may also influence this conversion. The objectives of the present study were to determine whether a 1-mo supplementation of dietary fiber as wheat bran increases urinary Equol excretion in Equol excreters and stimulates Equol production in nonexcreters and whether longer-term soy isoflavone intake increases Equol production or alters overall urinary isoflavone excretion. First, we screened 74 women, ages 20-40 y, and determined their Equol-excreter status. In these women, health and lifestyle patterns and habitual dietary intake did not differ according to Equol-excreter status. Next, 26 of the women (13 Equol excreters and 13 nonexcreters) were assigned (blocked on Equol-excreter status) to either longer-term (1 mo) or short-term (4 d) soy protein supplementation. Within each soy treatment group, women participated in two 1-mo intervention periods (the exact length was determined by each woman's menstrual cycle) during which they consumed their usual diets supplemented daily with either 0 or 16 g dietary fiber in a randomized crossover design. A 1-mo washout period separated the two diet periods. Among the 19 women who completed both periods, fiber supplementation did not increase Equol production in Equol excreters or nonexcreters. In addition, isoflavonoid excretion did not differ by fiber dose or length of soy intervention. These results suggest that a daily 16 g-fiber dose as wheat bran and the addition of soy protein do not alter significantly the capacity of colonic microflora to produce Equol.

  • urinary Equol excretion with a soy challenge influence of habitual diet
    Experimental Biology and Medicine, 1998
    Co-Authors: Johanna W Lampe, Susan C Karr, Andrea M Hutchins, Joanne L Slavin
    Abstract:

    AbstractEquol is an isoflavonoid phytoestrogen produced from the soy isoflavone daidzein by gut microflora. Not all humans produce Equol from daidzein, presumably due to differences in colonic bact...