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Effects of genistein and equol on human and rat testicular 3β-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase 3 activities

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Asian Journal of Andrology 2010年第4期12卷 519-526页

作者： Guo-Xin Hu Bing-Hai Zhao Yan-Hui Chu Hong-Yu Zhou Benson T. Akingbemi Zhi-Qiang Zheng Ren-Shan Ge Population Council New York NY 10065 USA School of Pharmacy Wenzhou Medical College Wenzhou 325000 China Heilongjiang Key Laboratory of Anti-fibrosis Biotherapy Mudanjiang Medical University Mudanjiang 157001 China Departments of Anatomy Physiology and Pharmacology Auburn University Auburn AL 36849 USA The Second Affiliated Hospital Wenzhou Medical College Wenzhou 325000 China

The objective of the present study was to investigate the effects of genistein and equol on 3β-hydroxysteroid de- hydrogenase （3β-HSD） and 17β-hydroxysteroid dehydrogenase 3 （17β-HSD3） in human and rat testis microsomes. These enzymes （3β-HSD and 17β-HSD3）, along with two others （cytochrome P450 side-chain cleavage enzyme and cytochrome P450 17α-hydroxylase/17-20 lyase）, catalyze the reactions that convert the steroid cholesterol into the sex hormone testosterone. Genistein inhibited 3β-HSD activity （0.2 μmol L^-1 pregnenolone） with half-maximal inhibition or a half-maximal inhibitory concentration （IC50） of 87 ± 15 （human） and 636 ± 155 nmol L^-1 （rat）. Genistein＇s mode of action on 3β-HSD activity was competitive for the substrate pregnenolonrge and noncompetitive for the cofactor NAD＋. There was no difference in genistein＇s potency of 3β-HSD inhibition between intact rat Leydig cells and testis microsomes. In contrast to its potent inhibition of 3β-HSD, genistein had lesser effects on human and rat 17β-HSD3 （0.1 μmol L^-1 androstenedione）, with an IC50 〉 100μmol L^-1. On the other hand, equol only inhibited human 3β-HSD by 42%, and had no effect on 3β-HSD and 17β-HSD3 in rat tissues. These observations imply that the ability of soy isoflavones to regulate androgen biosynthesis in Leydig cells is due in part to action on Leydig cell 3β- HSD activity. Given the increasing intake of soy-based food products and their potential effect on blood androgen levels, these findings are greatly relevant to public health.

关键词： 3β-hydroxysteroid dehydrogenase 17β-hydroxysteroid dehydrogenase 3 enzyme inhibition equol genistein

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The role of OPG/RANK/RANKL signaling pathway in the protective effect of equol on postmenopausal osteoporosis

The role of OPG/RANK/RANKL signaling pathway in the protecti...

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中国营养学会第十五届全国营养科学大会

作者： Xiangmin Ni Bin Wu Jian Wang Xinqiao Hospital Army Medical University 陆军军医大学

equol(Eq) is one of the end products of soy isoflavones(SI) in vivo. The structure and biological activity of Eq are very similar to estrogen,whose attenuation plays an important role in the occurrence and development of postmenopausal osteoporosis(PMOP).However, the effect and mechanism of Eq on PMOP have not been reported yet. This study aims to explore the protective effect of equol on PMOP and the role of OPG/RANK/RANKL signaling pathway in the osteoprotective effect. Methods The osteoblast ROS1728 were cultured with Eq(10-8 mol/L,10-7 mol/L,10-6 mol/L),estradiol(E2), separately, to detect the effect of Eq on the proliferation, apoptosis, cell cycle and expression of OPG/RANK/RANKL signaling pathway of osteoblasts. Then RNA silencing technology was used to explore the receptors through which Eq plays a role. In vivo study, female sprague dawley(SD) rats underwent ovariectomy to establish PMOP model and received intraperitoneal injection of Eq(at 0.25 mg/kg.d,0.5 mg/kg.d),E2 or normal saline for 8 weeks, and the control group received intraperitoneal injection of normal saline. The bone mineral density(BMD) and histomorphological changes of femoral bone were detected through dual-energy Xray bone densitometer and HE staining, the serum levels of bone metabolism indicators, OPG and RANKL were detected by ELISA kits, the mRNA expression levels of OPG and RANKL in bone marrow cells were ascertained by qRT-PCR method. Results In vitro study, Eq promoted the proliferation of osteoblasts and inhibited the apoptosis of osteoblasts, increased the proportion of cells in S phase and G2/M phase dose-dependently as E2 did. Eq treatment can regulate the expression of OPG/RANK/RANKL signaling pathway of osteoblasts, and this regulatory effect is mainly mediated through the ERβ receptor. In vivo study, compared with OVX group, the microstructure and BMD of the femur of rats were significantly improved through Eq or E2 intervention;the Eq or E2 treatment significantly increased

关键词： equol Postmenopausal osteoporosis Osteoblast OPG/RANK/RANKL

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Review: Anti-Oxidant and Anti-Aging Properties of equol in Prostate Health (BPH)

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Open Journal of Endocrine and Metabolic Diseases 2014年第1期4卷 1-12页

作者： Edwin D. Lephart The Department of Physiology and Developmental Biology Brigham Young University Provo USA The Neuroscience Center Brigham Young University Provo USA

Benign prostatic hyperplasia (BPH) is the pathological cellular progression of glandular proliferation associated with aging. The primary changes in prostate disorders are mediated by the conversion of the principle androgen, testosterone, to its more potent metabolite, 5α-dihydrotestosterone (5α-DHT). However, recent evidence suggests that estrogen hormonal actions via estrogen receptor subtypes also play an important role in BPH. Current pharmaceutical options for BPH have advantages, limitations and adverse effects. Complementary and Alternative Medicine (CAM) treatments for BPH include botanicals such as polyphenols and isoflavones. equol is a polyphenolic/isoflavonoid molecule derived from intestinal metabolism, dairy and dietary plant sources. equol has potent anti-oxidant and anti-aging properties to decrease prostatic irritation and potentially neoplastic growth. It has the unique characteristic to bind specifically 5α-DHT by sequestering 5α-DHT from the androgen receptor (AR), thus decreasing androgen hormone actions to improve prostate health by acting as a selective androgen modulator (SAM). It also has affinity for estrogen related receptor gamma (ERR-γ) and estrogen receptor beta (ER-β) within the prostate that is known to improve male health via selective estrogen receptor modulatory (SERM) activities to decrease inflammation, cellular proliferation and carcinogenesis. The possible clinical efficacy of equol on the symptoms associated with BPH is presented and the reviewed findings suggest that equol may provide a well-tolerated and rapid beneficial therapy for BPH that can be used alone or in combination with current pharmaceutical therapies. The beneficial clinical efficacy of equol observed may be due to the multiple positive biological actions that are not present in current pharmaceutical treatments.

关键词： Androgens Estrogens Isoflavonoid equol BPH SERM Selective Androgen Modulator (SAM)

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Severe &Moderate BPH Symptoms in Mid-Aged Men Improve with Isoflavonoid-equol Treatment: Pilot Intervention Study

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Open Journal of Urology 2013年第1期3卷 21-27页

作者： Edwin D. Lephart The Department of Physiology and Developmental Biology Brigham Young University Provo USA

Benign prostatic hyperplasia (BPH) is the pathological cellular progression of glandular proliferation associated with aging. Current available treatment options for BPH have limitations and various adverse effects. equol is a polyphenolic/isoflavonoid molecule derived from intestinal metabolism, dairy and dietary plant sources. It has the unique characteristic to bind specifically 5α-dihydrotestosterone (5α-DHT) by sequestering 5α-DHT from the androgen receptor, thus decreasing androgen hormone actions to improve prostate health by acting as a selective androgen modulator (SAM). It also has affinity for estrogen related receptor gamma (ERR-γ) and estrogen receptor beta (ER-β) within the prostate that is known to improve male health via selective estrogen receptor modulatory (SERM) activities to decrease inflammation, cellular proliferation and carcinogenesis. We investigated the possible clinical efficacy of equol on the symptoms associated with benign prostatic hyperplasia (BPH) in this study. Materials and Methods: We performed a pilot intervention study evaluating the effects of low dose oral equol supplement (6 mg, twice a day with meals) for 4 weeks in a total of 18 men (49 - 60 years old) with moderate or severe BPH. Subjects included in the study: gave informed consent, underwent a physical examination and verified their BPH symptoms as measured by the International Prostate Symptom Scores (IPSS) and then were assigned to the moderate or severe BPH groups based upon their total IPSS index. All adverse events were reported. The primary efficacy measure was the IPSS parameters comparing baseline to 2 and 4 week IPSS indices. Blood samples were collected at the baseline and 4th week visits that served as secondary efficacy parameters that included testosterone, 5α-DHT and general blood chemistries along with cardiac and hepatic function panels. Results: Low dose equol positively improved moderate to severe BPH symptoms according to the IPSS indices. In moderate

关键词： Isoflavonoid equol BPH Androgens SERM

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<i>In Vitro</i>Effect of Soy Isoflavone and equol on Soluble CD40L Release Stimulated by Ristocetin in Platelets from Postmenopause Women

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Journal of Biomedical Science and Engineering 2015年第1期8卷 24-30页

作者： Natalia Gonzalez Argelia Garrido Ingrid Acevedo Luis Valladares Institute of Nutrition and Food Technology Universidad de Chile Santiago Chile

The inhibition of specific flavonoid on the in vitro platelet aggregation induced by collagen, arachidonic acid and thromboxane A2 (TxA2) agonist, seems to be related mostly to their ability to compete for binding to the TxA2 receptor (TP). The aim of this study was to analyze the effect of soy isoflavone and equol in terms of inhibiting the platelet aggregation and sCD40L release stimulated by ristocetin, an in vitro-activator of glycoprotein Ib/IX/V, in platelets from postmenopausal women. When platelets were stimulated by 0.75 mg/ml ristocetin, equol (10 μM) exhibited a greater inhibitory activity on platelet aggregation (~68%) than genistein or daidzein. The effect of equol was dependent on the concentration of platelet aggregation agonist. In the presence of ristocetin (0.75 mg/ml, 1.125 mg/ml and 1.5 mg/ml), the inhibitory effect of 10 μM equol was 68% ± 5%, 54% ± 4% and 31% ± 5%, respectively. equol (10 μM) was a potent inhibitor (~35%) of sCD40L release when stimulated with 1.5 mg/ml ristocetin. However, no significant differences were noted in platelets incubated in the presence of genistein or daidzein and stimulated by ristocetin. On the other hand, SQ29548, a high TP antagonist, also inhibited the sCD40L release stimulated by ristocetin. Finally, 10 μM of genistein, daidzein or equol did not significantly affect the thromboxane B2 production when platelets were incubated with 1.5 mg/ml ristocetin. The relevance of this study was to find that equol exhibits a potent activity by inhibiting ristocetin-induced sCD40L release, suggesting that soy isoflavone has important biological effects on the hemostatic system. However, clinical trials will be necessary to assess the effect of equol on platelet and their impact on inflammatory markers.

关键词： Platelet sCD40L Phyoestrogen Isoflavone equol

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Correlation of equol (7-Hydroxy-3-(4-Hydroxyphenyl)Chroman) in Woman Urine with the Symptoms of Menopause

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Journal of Biosciences and Medicines 2016年第1期4卷 132-138页

作者： Rima Yulia Effriyanti Tita Husnitawati Madjid Hanom Husni Syam Department of Obstetrics and Gynecology Faculty of Medicine Universitas Padjadjaran/Dr. Hasan Sadikin General Hospital Bandung Indonesia

Objective: In order to identify the correlation between equol excreted through human urine and the symptom of menopause. Methods: The method used is cross sectional study examined to 99 postmenopausal women fulfilling the inclusion criteria from February 2014 to July 2014. This research was taken in the Endocrinology Clinic, Department of Obstetrics and Gynecology, Hasan Sadikin Hospital and Unpad’s Pharmacokinetic Laboratory. All objects were interviewed using menopause rating scale (MRS) questionnaire. Their urine samples were analyzed using high performance liquid chromatography (HPLC). Then the results of questionnaire and HPLC test were evaluated. Results: The result is 97 objects (98%) detected having menopausal symptoms, produced equol. There is significant correlation between the level of equol in post-menopausal women that showed correlation (-0.71) which mean the higher the equol level, the lower the MRS score (p equol level in menopause women urine is a good predictor to identify the level of menopause symptoms.

关键词： equol Menopause Symptoms Menopause Rating Scale

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The cross-sectional study of the relationship between soy isoflavones,equol and the menopausal symptoms in Japanese women

The cross-sectional study of the relationship between soy is...

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中国营养学会第十次全国营养学术会议暨第七届会员代表大会

作者： Shigeto Uchiyama Tomomi Ueno Kyosuke Masaki Seiichi Shimizu Takeshi Aso Tomoko Shirota Otsuka Pharmaceutical Co. Ltd. Saga Nutraceuticals Research Institute Miyagi Gakuin Women’s University Tokyo Medical and Dental University Hospital Faculty of Medicine Nakamura Gakuen University Division of Nutritional Biochemistry

The objective of the study was to investigate the relationship between urinary excretion of isoflavones and menopausal symptoms of Japanese women in peri-and postmenopausal *** and eight dietitians living in Fukuoka prefecture were recruited into the ***-rated postal surveies and collections of 24hr urine sample for measurement of urinary total isoflavonoids,genistein,daidzein and equol levels by HPLC were *** urinary excretions of isoflavonoids,genistein,daidzein and equol were 38.9±29.2,19.6±15.1,10.0±8.9,9.34±14.1μmol/24hr (mean±SD),*** genistein and daidzein were detected in all samples,but equol was detected only 51.6%.Menopausal symptoms were evaluated using simplified menopausal index (SMI) in 59 peri-and postmenopausal *** 50 percentile value of SMI score was 15,and the women complaining hot flushes,palpitation and chillness in extremities were 20.8%,41.5%,34.0%,respectively. No significant difference in urinary excretion of genistein and daidzein was detected between the groups of high SMI(greater than 15) and low SMI (less than 15),but the equol levels of higher SMI group were significantly lower than those of lower SMI group (Pequol converted from isoflavones by intestinal bacteria mainly contribute to suppress the menopausal *** quantitative analysis indicated that urinary epuol more than 5μmol/24hr is necessary for reducing the menopausal symptoms of Japanese menopausal women.

关键词： Soy isoflavone equol Menopausal symptoms urinary excretion Japanese peri-and postmenopausal women

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ERK1/2信号通路对genistein和equol雌激素效应的影响

ERK1/2信号通路对genistein和equol雌激素效应的影响

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作者：刘华青南京医科大学

学位级别：硕士

MAPK信号转导通路的异常与多种肿瘤或增殖性疾病关系密切。现已在哺乳动物细胞克隆和鉴定了4个MAPK亚族: ERK1/2、ERK5、JNK和p38 MAPK,其中ERK1/2与乳腺癌最相关。在MCF-7乳腺癌细胞中,ERK1/2激活是雌二醇诱导的细胞增殖关键信号转导... 详细信息

MAPK信号转导通路的异常与多种肿瘤或增殖性疾病关系密切。现已在哺乳动物细胞克隆和鉴定了4个MAPK亚族: ERK1/2、ERK5、JNK和p38 MAPK,其中ERK1/2与乳腺癌最相关。在MCF-7乳腺癌细胞中,ERK1/2激活是雌二醇诱导的细胞增殖关键信号转导事件。雌激素在乳腺癌细胞中的增殖效应主要是通过雌激素受体机制。genistein和daidzein是两种存在于大豆中的主要异黄酮成分,equol是daidzein的关键代谢物,由于它们可能作为激素替代治疗的天然替代物,减轻绝经后综合症,所以受到广泛关注。雌激素和异黄酮类植物雌激素的经典基因组效应是通过雌激素受体-激素复合物结合靶基因启动子区特异雌激素反应元件,转录激活响应基因;雌激素也可通过其它转录因子激活靶基因而不依赖于雌激素反应元件。最近研究显示,细胞表面受体能快速响应雌激素和植物雌激素。这些膜相关雌激素受体和细胞信号通路(如MEK/ERK和PI3K通路)交互作用,从而启动非基因组效应。信号转导通路可连接雌激素基因组效应与非基因组效应。这种从非基因组到基因组信号机制不同于雌激素受体(ER)作用于替代反应元件调控转录。ERα是许多乳腺癌生长的主要调控点,提供可能的治疗靶点。更好的理解ER机制以及ER和ERK1/2信号通路的交互作用可以为激素依赖型乳腺癌治疗提供更有针对性策略,以及对认识膳食中的雌激素样物质对激素依赖型乳腺癌患者的健康效应以及正确指导乳腺癌患者膳食选择均具有重要意义。目的:以激素依赖型乳腺癌细胞为模型,研究ERK1/2信号通路对genistein和equol雌激素效应的影响,探讨ERK1/2信号通路与ERα介导转录激活的关系。方法:采用噻唑蓝(MTT)比色法检测genistein和equol以及联合信号通路抑制剂对激素依赖型MCF-7乳腺癌细胞增殖的影响;采用流式细胞仪检测genistein和equol以及联合ER拮抗剂与MEK1/2抑制剂处理细胞48后细胞周期变化;实时定量PCR检测genistein和equol以及联合ERα拮抗剂与MEK1/2抑制剂处理细胞后ERα靶基因pS2、GREB1和EEIG1的表达;Western blotting检测genistein和equol以及联合雌激素拮抗剂ICI、MEK1/2抑制剂U0126对ERα和ERK1/2信号蛋白表达的影响;应用报告基因方法检测genistein和equol以及联合ERα拮抗剂与MEK1/2抑制剂处理MDA-MB-231细胞24h后雌激素反应元件报告基因活性结果:MTT及流式细胞分析结果显示,生理浓度的genistein和equo(l0.01-10μM)促进MCF-7乳腺癌细胞增殖和S期进程。这些作用能被ERα拮抗剂OHT、ICI以及MEK1/2抑制剂U0126阻断,说明这种促进效应涉及到ER依赖机制和MEK/ERK信号通路。报告基因实验结果显示U0126能完全阻断genistein和equol诱导的ERα转录活性;实时定量PCR检测结果显示, genistein和equol能诱导ERα靶基因pS2、GREB1和EEIG1的表达,呈现时间效应,而且这种诱导作用能被ERα拮抗剂以及MEK1/2抑制剂阻断;提示MEK/ERK信号通路是ERα介导的转录所需要的。Western blotting检测结果显示genistein和equol诱导延迟ERK1/2激活,U0126能阻断ERK1/2激活,并且能进一步减少genistein和equol介导的ERα蛋白表达;而抗雌激素ICI对genistein和equol介导延迟的ERK1/2激活没有影响,这表明ERK1/2激活可能位于ERα介导的信号通路的上游。结论:低浓度的genistein和equol是通过ERα介导转录和ERK1/2激活促进细胞增殖和细胞周期进程,延迟而稳定的ERK1/2激活是genistein和equol诱导ERα转录活性所需要的。

关键词： genistein equol ERK1/2 ERα转录活性 MCF-7乳腺癌细胞

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ERK1/2信号通路对genistein和equol雌激素效应的影响

ERK1/2信号通路对genistein和equol雌激素效应的影响

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食品、饲料安全与风险评估学术会议

作者：刘华青李忠南京医科大学公共卫生学院

前言genistein和daidzein是两种存在于大豆中的主要异黄酮成分,equol是daidzein的关键代谢物,由于它们可能作为激素替代治疗的天然替代物,减轻绝经后综合症,所以受到广泛关注。雌激素和异黄酮类植物雌激素的经典基因组效应是通过雌激素... 详细信息

前言genistein和daidzein是两种存在于大豆中的主要异黄酮成分,equol是daidzein的关键代谢物,由于它们可能作为激素替代治疗的天然替代物,减轻绝经后综合症,所以受到广泛关注。雌激素和异黄酮类植物雌激素的经典基因组效应是通过雌激素受体-激素复合物结合靶基因启动子区特异雌激素反应元件,转录激活响应基因;雌激素也可通过其它转录因

关键词： genistein 信号通路 equol ERK1/2 细胞周期进程雌激素反应元件雌激素效应

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雌马醇对映体的高效液相色谱分离

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药物分析杂志 2006年第6期26卷 795-798页

作者：陈磊万谦宏天津大学药物科学与技术学院天津300072

目的:考察色谱条件对 equol 对映体手性分离的影响,建立反相条件下手性流动相添加剂法色谱分离方法。方法:采用高效液相色谱手性流动相法,固定相为 ODS 柱(250mm×4.6mm,5μm),流动相为环糊精水溶液与有机改性剂(甲醇、乙醇、异丙醇、乙... 详细信息

目的:考察色谱条件对 equol 对映体手性分离的影响,建立反相条件下手性流动相添加剂法色谱分离方法。方法:采用高效液相色谱手性流动相法,固定相为 ODS 柱(250mm×4.6mm,5μm),流动相为环糊精水溶液与有机改性剂(甲醇、乙醇、异丙醇、乙腈)的混合溶液,流速1.0mL·min^(-1),检测波长254nm,柱温为室温。结果:首次用β-环糊精作为手性流动相添加剂成功拆分了 equol 对映体,并确立最佳分离条件:30mmol·L^(-1)β-CD 水溶液(pH 6.4)-乙腈(95:5),分离因子(α)可达1.21。结论:本方法简便易行,操作成本低,可直接放大到制备分离。

关键词：手性拆分 equol 手性流动相添加剂 β-环糊精大豆异黄酮

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