Equol (BioDeep_00000017405)
Main id: BioDeep_00000001684
human metabolite PANOMIX_OTCML-2023 blood metabolite
代谢物信息卡片
2H-1-Benzopyran-7-ol, 3,4-dihydro-3-(4-hydroxyphenyl)-; 7,4-Homoisoflavane; (+/-)-Equol; NV 07alpha
化学式: C15H14O3 (242.0943)
中文名称: (±)-雌马酚, 雌马酚
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1(O)C=CC2CC(C3C=CC(O)=CC=3)COC=2C=1
InChI: InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2
描述信息
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
3-(4-Hydroxyphenyl)chroman-7-ol is a member of hydroxyisoflavans.
(±)-Equol is the racemate of equol. (±)-equol exhibits EC50s of 200 and 74 nM for human ERα and ERβ, respectively. Equol is a metabolite of the soy isoflavones, daidzin and daidzein.
同义名列表
35 个代谢物同义名
2H-1-Benzopyran-7-ol, 3,4-dihydro-3-(4-hydroxyphenyl)-; 7,4-Homoisoflavane; (+/-)-Equol; NV 07alpha; 2H-1-Benzopyran-7-ol, 3,4-dihydro-3-(4-hydroxyphenyl)-; 3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol; 3-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol; 3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol; (R,S)-Equol; Equol (+/-)-;Equol (racemic); 7-Hydroxy-3-(4-hydroxyphenyl)chroman; 7-hydroxy-3-(4-hydroxyphenyl)chroman; 4,7-dihydroxy-3,4-dihydroisoflavone; ( inverted exclamation markA)-Equol; 3-(4-Hydroxy-phenyl)-chroman-7-ol; 3-(4-Hydroxyphenyl)chroman-7-ol; (+/-) 7,4-Dihydroxy Isoflavane; (+/-)-Equol, >=99.0\\% (TLC); 4,7-Dihydroxyflavandiol; 4,7-dihydroxyisoflavane; 7,4-dihydroxyisoflavan; 7,4-Homoisoflavane; EQUOL,(+/-)-(SH); UNII-2RZ8A7D0E8; Equol (racemic); (plusmn)-Equol; (.+/-.)-Equol; Equol, (+/-)-; SMP2_000187; (R,S)-Equol; Equol (R,S); (+/-)-Equol; 2RZ8A7D0E8; (+/-)Equol; NV-07alpha; (RS)-Equol; Rac-Equol; (±)-Equol; Equol
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:181441
- PubChem: 382975
- HMDB: HMDB0243678
- ChEMBL: CHEMBL1957037
- LipidMAPS: LMPK12080003
- MeSH: 4,7-dihydroxy-3,4-dihydroisoflavone
- ChemIDplus: 0094105905
- CAS: 94105-90-5
- CAS: 66036-38-2
- medchemexpress: HY-100583A
- RefMet: Equol
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
2 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Nozomu Miyazaki, Ryota Katsura, Chiaki Ozaki, Tatsuo Suzutani. Protective effect of equol intake on bladder dysfunction in a rat model of bladder outlet obstruction.
Lower urinary tract symptoms.
2024 May; 16(3):e12518. doi:
10.1111/luts.12518. [PMID: 38777796] - Remi Yoshikata, Khin Zay Yar Myint, Junichi Taguchi. Comparison of blood and urine concentrations of equol by LC‒MS/MS method and factors associated with equol production in 466 Japanese men and women.
PloS one.
2024; 19(3):e0288946. doi:
10.1371/journal.pone.0288946. [PMID: 38536793] - Jongkeun Choi, Yongho Kim, Bekir Engin Eser, Jaehong Han. Theoretical study on the glycosidic C-C bond cleavage of 3''-oxo-puerarin.
Scientific reports.
2023 09; 13(1):16282. doi:
10.1038/s41598-023-43379-1. [PMID: 37770535] - Fei Teng, Zhongwen Lu, Fei Gao, Jing Liang, Jiawen Li, Xuanhe Tian, Xianshuai Wang, Haowei Guan, Jin Wang. Systems biology approaches to identify potential targets and inhibitors of the intestinal microbiota to treat depression.
Scientific reports.
2023 07; 13(1):11225. doi:
10.1038/s41598-023-38444-8. [PMID: 37433869] - Damien P Belobrajdic, Genevieve James-Martin, Darren Jones, Cuong D Tran. Soy and Gastrointestinal Health: A Review.
Nutrients.
2023 Apr; 15(8):. doi:
10.3390/nu15081959. [PMID: 37111176] - Neal D Barnard, Hana Kahleova, Danielle N Holtz, Tatiana Znayenko-Miller, Macy Sutton, Richard Holubkov, Xueheng Zhao, Stephanie Galandi, Kenneth D R Setchell. A dietary intervention for vasomotor symptoms of menopause: a randomized, controlled trial.
Menopause (New York, N.Y.).
2023 01; 30(1):80-87. doi:
10.1097/gme.0000000000002080. [PMID: 36253903] - Rachel L Shrode, Nicole Cady, Samantha N Jensen, Nicholas Borcherding, Ashutosh K Mangalam. Isoflavone consumption reduces inflammation through modulation of phenylalanine and lipid metabolism.
Metabolomics : Official journal of the Metabolomic Society.
2022 10; 18(11):84. doi:
10.1007/s11306-022-01944-1. [PMID: 36289122] - X Yu, Y Q Zou, Y Wang, Z K Chen, D F Ma. [Equol and its enantiomers inhibited urethane-induced lung cancer in mice].
Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences.
2022 Apr; 54(2):244-248. doi:
. [PMID: 35435186] - Xiao Zhang, Akira Fujiyoshi, Vasudha Ahuja, Abhishek Vishnu, Emma Barinas-Mitchell, Aya Kadota, Katsuyuki Miura, Daniel Edmundowicz, Hirotsugu Ueshima, Akira Sekikawa. Association of equol producing status with aortic calcification in middle-aged Japanese men: The ERA JUMP study.
International journal of cardiology.
2022 Apr; 352(?):158-164. doi:
10.1016/j.ijcard.2022.01.065. [PMID: 35122909] - Hiroaki Takeuchi, Yu Yoshikane, Hirotsugu Takenaka, Asako Kimura, Jahirul Md Islam, Reimi Matsuda, Aoi Okamoto, Yusuke Hashimoto, Rie Yano, Koichi Yamaguchi, Shouichi Sato, Satoshi Ishizuka. Health Effects of Drinking Water Produced from Deep Sea Water: A Randomized Double-Blind Controlled Trial.
Nutrients.
2022 Jan; 14(3):. doi:
10.3390/nu14030581. [PMID: 35276942] - Qianrui Wang, Bert Spenkelink, Rungnapa Boonpawa, Ivonne M C M Rietjens. Use of Physiologically Based Pharmacokinetic Modeling to Predict Human Gut Microbial Conversion of Daidzein to S-Equol.
Journal of agricultural and food chemistry.
2022 Jan; 70(1):343-352. doi:
10.1021/acs.jafc.1c03950. [PMID: 34855380] - Guang Xiong, Changbo Huang, Yuping Zou, Ziyin Tao, Jun Zou, Jiean Huang. Associations of Urinary Phytoestrogen Concentrations with Nonalcoholic Fatty Liver Disease among Adults.
Journal of healthcare engineering.
2022; 2022(?):4912961. doi:
10.1155/2022/4912961. [PMID: 35399831] - Juyeon Lee, Ju-Young Kang, Kwang-Pil Ko, Sue-Kyung Park. The Association between Plasma Concentration of Phytoestrogens and Hypertension within the Korean Multicenter Cancer Cohort.
Nutrients.
2021 Dec; 13(12):. doi:
10.3390/nu13124366. [PMID: 34959918] - Mitsuo Sakamoto, Nao Ikeyama, Masahiro Yuki, Takumi Murakami, Hiroshi Mori, Takao Iino, Moriya Ohkuma. Adlercreutzia hattorii sp. nov., an equol non-producing bacterium isolated from human faeces.
International journal of systematic and evolutionary microbiology.
2021 Dec; 71(12):. doi:
10.1099/ijsem.0.005121. [PMID: 34870581] - Takemi Akahane, Daisuke Kaya, Ryuichi Noguchi, Kosuke Kaji, Haruna Miyakawa, Yukihisa Fujinaga, Yuki Tsuji, Hiroaki Takaya, Yasuhiko Sawada, Masanori Furukawa, Koh Kitagawa, Takahiro Ozutsumi, Hideto Kawaratani, Kei Moriya, Tadashi Namisaki, Hitoshi Yoshiji. Association between Equol Production Status and Nonalcoholic Steatohepatitis.
International journal of molecular sciences.
2021 Nov; 22(21):. doi:
10.3390/ijms222111904. [PMID: 34769332] - Geethika S G Liyanage, Ryo Inoue, Mina Fujitani, Tomoko Ishijima, Taisei Shibutani, Keiko Abe, Taro Kishida, Shinji Okada. Effects of Soy Isoflavones, Resistant Starch and Antibiotics on Polycystic Ovary Syndrome (PCOS)-Like Features in Letrozole-Treated Rats.
Nutrients.
2021 Oct; 13(11):. doi:
10.3390/nu13113759. [PMID: 34836015] - Zhao-Min Liu, Di Zhang, Guoyi Li, Suzanne C Ho, Yu-Ming Chen, Jing Ma, Qi Huang, Shuyi Li, Wen-Hua Ling. The 6-month effect of whole soy and purified isoflavones daidzein on thyroid function-A double-blind, randomized, placebo controlled trial among Chinese equol-producing postmenopausal women.
Phytotherapy research : PTR.
2021 Oct; 35(10):5838-5846. doi:
10.1002/ptr.7244. [PMID: 34494323] - Tomoko Fujitani, Yukiko Fujii, Zhaoqing Lyu, Mariko Harada Sassa, Kouji H Harada. Urinary equol levels are positively associated with urinary estradiol excretion in women.
Scientific reports.
2021 09; 11(1):19532. doi:
10.1038/s41598-021-98872-2. [PMID: 34593903] - Kelsey Rhian Pool, Tayler Catherine Kent, Dominique Blache. Oestrogenic metabolite equol negatively impacts the functionality of ram spermatozoa in vitro.
Theriogenology.
2021 Sep; 172(?):216-222. doi:
10.1016/j.theriogenology.2021.07.005. [PMID: 34280666] - Susana Langa, José M Landete. Strategies to achieve significant physiological concentrations of bioactive phytoestrogens in plasma.
Critical reviews in food science and nutrition.
2021 Sep; ?(?):1-13. doi:
10.1080/10408398.2021.1971946. [PMID: 34470513] - Yuqi Dou, Gonglie Chen, Yuanfa Cai, Xiao Lin, Zekun Chen, Xue Yu, Ying Wang, Ling Zhang, Yuhui Wang, Defu Ma. [Lipids-lowering effects of equol on low density lipoprotein receptor knockout hamsters].
Wei sheng yan jiu = Journal of hygiene research.
2021 Sep; 50(5):775-780. doi:
10.19813/j.cnki.weishengyanjiu.2021.05.012. [PMID: 34749871] - Hitomi Tanaka, Shosuke Ito, Makoto Ojika, Tomoko Nishimaki-Mogami, Kazunari Kondo, Kazumasa Wakamatsu. The Oxidation of Equol by Tyrosinase Produces a Unique Di-ortho-Quinone: Possible Implications for Melanocyte Toxicity.
International journal of molecular sciences.
2021 Aug; 22(17):. doi:
10.3390/ijms22179145. [PMID: 34502054] - Mercedes Y Lacourt-Ventura, Brayan Vilanova-Cuevas, Delmarie Rivera-Rodríguez, Raysa Rosario-Acevedo, Christine Miranda, Gerónimo Maldonado-Martínez, Johanna Maysonet, Darlene Vargas, Yelitza Ruiz, Robert Hunter-Mellado, Luis A Cubano, Suranganie Dharmawardhane, Johanna W Lampe, Abel Baerga-Ortiz, Filipa Godoy-Vitorino, Michelle M Martínez-Montemayor. Soy and Frequent Dairy Consumption with Subsequent Equol Production Reveals Decreased Gut Health in a Cohort of Healthy Puerto Rican Women.
International journal of environmental research and public health.
2021 08; 18(16):. doi:
10.3390/ijerph18168254. [PMID: 34444002] - Tobias Goris, Rafael R C Cuadrat, Annett Braune. Flavonoid-Modifying Capabilities of the Human Gut Microbiome-An In Silico Study.
Nutrients.
2021 08; 13(8):. doi:
10.3390/nu13082688. [PMID: 34444848] - Cong Lu, Rongjing Gao, Yingyu Zhang, Ning Jiang, Ying Chen, Jing Sun, Qiong Wang, Bei Fan, Xinmin Liu, Fengzhong Wang. S-equol, a metabolite of dietary soy isoflavones, alleviates lipopolysaccharide-induced depressive-like behavior in mice by inhibiting neuroinflammation and enhancing synaptic plasticity.
Food & function.
2021 Jul; 12(13):5770-5778. doi:
10.1039/d1fo00547b. [PMID: 34038497] - Yingyu Guo, Lichao Zhao, Xiang Fang, Qingping Zhong, Huijun Liang, Wenou Liang, Li Wang. Isolation and identification of a human intestinal bacterium capable of daidzein conversion.
FEMS microbiology letters.
2021 05; 368(8):. doi:
10.1093/femsle/fnab046. [PMID: 33930123] - Jung-Hoon Kim, Chiyeon Lim, Suin Cho. Ischemic-time associated reductions in equol monosulfate plasma levels in a mouse model of ischemic stroke: support the existence of a 'brain-gut axis'.
Neuroreport.
2021 04; 32(6):458-464. doi:
10.1097/wnr.0000000000001618. [PMID: 33657076] - Ankur Kumar Tanwar, Neha Dhiman, Amit Kumar, Vikas Jaitak. Engagement of phytoestrogens in breast cancer suppression: Structural classification and mechanistic approach.
European journal of medicinal chemistry.
2021 Mar; 213(?):113037. doi:
10.1016/j.ejmech.2020.113037. [PMID: 33257172] - Koichiro Hayashi, Hidetaka Yamaguchi, Hiroshi Amaoka, Terumasa Takahara, Shiori Kunisa, Nanae Tamai, Nagisa Maejima, Nana Watanabe, Yui Kobayashi, Hirofumi Tanaka. Equol-producing status affects exercise training-induced improvement in arterial compliance in postmenopausal women.
Journal of applied physiology (Bethesda, Md. : 1985).
2021 03; 130(3):827-835. doi:
10.1152/japplphysiol.00651.2020. [PMID: 33356982] - Takahito Chiba, Takuya Nagai, Futoshi Kohda, Takeshi Nakahara, Michihiro Kono. The Connection between Urinary Equol Levels and the Prevalence of Atopic Dermatitis.
International archives of allergy and immunology.
2021; 182(1):32-38. doi:
10.1159/000510119. [PMID: 32932251] - Shelby L Johnson, Hyun Y Park, Dhiraj A Vattem, Paula Grammas, Hang Ma, Navindra P Seeram. Equol, a Blood-Brain Barrier Permeable Gut Microbial Metabolite of Dietary Isoflavone Daidzein, Exhibits Neuroprotective Effects against Neurotoxins Induced Toxicity in Human Neuroblastoma SH-SY5Y Cells and Caenorhabditis elegans.
Plant foods for human nutrition (Dordrecht, Netherlands).
2020 Dec; 75(4):512-517. doi:
10.1007/s11130-020-00840-0. [PMID: 32761299] - Yun-Fei Ge, Chun-Hong Wei, Wei-Hao Wang, Long-Kui Cao. The resistant starch from sorghum regulates lipid metabolism in menopausal rats via equol.
Journal of food biochemistry.
2020 08; 44(8):e13295. doi:
10.1111/jfbc.13295. [PMID: 32572977] - Zhao-Min Liu, Guoyi Li, Di Zhang, Suzanne C Ho, Yu-Ming Chen, Jing Ma, Qi Huang, Shuyi Li, Wen-Hua Ling. Effect of whole soy and purified daidzein on androgenic hormones in chinese equol-producing post-menopausal women: a six-month randomised, double-blinded and Placebo-Controlled trial.
International journal of food sciences and nutrition.
2020 Aug; 71(5):644-652. doi:
10.1080/09637486.2020.1712682. [PMID: 31914834] - Christoph Haudum, Lisa Lindheim, Angelo Ascani, Christian Trummer, Angela Horvath, Julia Münzker, Barbara Obermayer-Pietsch. Impact of Short-Term Isoflavone Intervention in Polycystic Ovary Syndrome (PCOS) Patients on Microbiota Composition and Metagenomics.
Nutrients.
2020 Jun; 12(6):. doi:
10.3390/nu12061622. [PMID: 32492805] - Hongli Dong, Feng Xiong, Qingwei Zhong, Yihong Li, Meng Liu, Wenhua Ling, Xinyi Tang, Yuming Chen. Urinary equol is associated with bioavailable testosterone but not total testosterone in women.
Endocrine journal.
2020 Mar; 67(3):257-266. doi:
10.1507/endocrj.ej19-0319. [PMID: 31748434] - Hong-Li Dong, Xin-Yi Tang, Yun-Yang Deng, Qing-Wei Zhong, Cheng Wang, Zhe-Qing Zhang, Yu-Ming Chen. Urinary equol, but not daidzein and genistein, was inversely associated with the risk of type 2 diabetes in Chinese adults.
European journal of nutrition.
2020 Mar; 59(2):719-728. doi:
10.1007/s00394-019-01939-0. [PMID: 30953148] - Qianrui Wang, Bert Spenkelink, Rungnapa Boonpawa, Ivonne M C M Rietjens, Karsten Beekmann. Use of Physiologically Based Kinetic Modeling to Predict Rat Gut Microbial Metabolism of the Isoflavone Daidzein to S-Equol and Its Consequences for ERα Activation.
Molecular nutrition & food research.
2020 03; 64(6):e1900912. doi:
10.1002/mnfr.201900912. [PMID: 32027771] - Hiroko Yoshioka, Masamichi Watanabe, Fumio Nanba, Toshio Suzuki, Satoru Fukiya, Atsushi Yokota, Toshiya Toda. Administration of Cholic Acid Inhibits Equol Production from Daidzein in Mice.
Journal of nutritional science and vitaminology.
2020; 66(6):571-576. doi:
10.3177/jnsv.66.571. [PMID: 33390399] - Kanumuri Siva Rama Raju, Mamunur Rashid, Manoj Gundeti, Isha Taneja, Mohd Yaseen Malik, Sandeep Kumar Singh, Swati Chaturvedi, Muralikrishna Challagundla, Sheelendra Pratap Singh, J R Gayen, Muhammad Wahajuddin. LC-ESI-MS/MS method for the simultaneous determination of isoformononetin, daidzein, and equol in rat plasma: Application to a preclinical pharmacokinetic study.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2019 Oct; 1129(?):121776. doi:
10.1016/j.jchromb.2019.121776. [PMID: 31629309] - Yuan Heng, Min Jung Kim, Hye Jeong Yang, Suna Kang, Sunmin Park. Lactobacillus intestinalis efficiently produces equol from daidzein and chungkookjang, short-term fermented soybeans.
Archives of microbiology.
2019 Oct; 201(8):1009-1017. doi:
10.1007/s00203-019-01665-5. [PMID: 31069407] - Jian Zhang, Li Ren, Min Yu, Xiaojiang Liu, Wenyu Ma, Lu Huang, Xuegang Li, Xiaoli Ye. S-equol inhibits proliferation and promotes apoptosis of human breast cancer MCF-7 cells via regulating miR-10a-5p and PI3K/AKT pathway.
Archives of biochemistry and biophysics.
2019 09; 672(?):108064. doi:
10.1016/j.abb.2019.108064. [PMID: 31390527] - Thomas Migkos, Lenka Applová, Pavel Horký, Václav Tvrdý, Jana Karlíčková, Kateřina Macáková, Marcel Hrubša, Maria Carmen Catapano, Magdalena Tomanek, Milan Pour, Přemysl Mladěnka. The influence of microbial isoflavonoid specific metabolites on platelets and transition metals iron and copper.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2019 Sep; 62(?):152974. doi:
10.1016/j.phymed.2019.152974. [PMID: 31181402] - Jeong Eun Kwon, Jaewon Lim, Ina Bang, Inhye Kim, Donghyuk Kim, Se Chan Kang. Fermentation product with new equol-producing Lactobacillus paracasei as a probiotic-like product candidate for prevention of skin and intestinal disorder.
Journal of the science of food and agriculture.
2019 Jul; 99(9):4200-4210. doi:
10.1002/jsfa.9648. [PMID: 30767231] - Aki Obara, Mizuki Kinoshita, Kaori Hosoda, Akitomo Yokokawa, Hiromi Shibasaki, Kazuo Ishii. Identification of equol-7-glucuronide-4'-sulfate, monoglucuronides and monosulfates in human plasma of 2 equol producers after administration of kinako by LC-ESI-MS.
Pharmacology research & perspectives.
2019 06; 7(3):e00478. doi:
10.1002/prp2.478. [PMID: 31086672] - Erin N Bax, Karlee E Cochran, Jiude Mao, Charles E Wiedmeyer, Cheryl S Rosenfeld. Opposing effects of S-equol supplementation on metabolic and behavioral parameters in mice fed a high-fat diet.
Nutrition research (New York, N.Y.).
2019 04; 64(?):39-48. doi:
10.1016/j.nutres.2018.12.008. [PMID: 30802721] - Ludmila Křížová, Kateřina Dadáková, Jitka Kašparovská, Tomáš Kašparovský. Isoflavones.
Molecules (Basel, Switzerland).
2019 Mar; 24(6):. doi:
10.3390/molecules24061076. [PMID: 30893792] - Chikara Iino, Tadashi Shimoyama, Kaori Iino, Yoshihito Yokoyama, Daisuke Chinda, Hirotake Sakuraba, Shinsaku Fukuda, Shigeyuki Nakaji. Daidzein Intake Is Associated with Equol Producing Status through an Increase in the Intestinal Bacteria Responsible for Equol Production.
Nutrients.
2019 Feb; 11(2):. doi:
10.3390/nu11020433. [PMID: 30791484] - James W Daily, Byoung-Seob Ko, Jina Ryuk, Meiling Liu, Weijun Zhang, Sunmin Park. Equol Decreases Hot Flashes in Postmenopausal Women: A Systematic Review and Meta-Analysis of Randomized Clinical Trials.
Journal of medicinal food.
2019 Feb; 22(2):127-139. doi:
10.1089/jmf.2018.4265. [PMID: 30592686] - Anna Fickler, Stefanie Staats, Gerald Rimbach, Carsten Schulz. Screening dietary biochanin A, daidzein, equol and genistein for their potential to increase DHA biosynthesis in rainbow trout (Oncorhynchus mykiss).
PloS one.
2019; 14(1):e0210197. doi:
10.1371/journal.pone.0210197. [PMID: 30645603] - Mina Fujitani, Takafumi Mizushige, Keshab Bhattarai, Sudhashree Adhikari, Junji Ishikawa, Taro Kishida. Dietary daidzein induces accumulation of S-equol in enterohepatic circulation to far higher levels than that of daidzein in female rats with and without ovariectomy.
Biomedical research (Tokyo, Japan).
2019; 40(3):97-105. doi:
10.2220/biomedres.40.97. [PMID: 31231095] - Giovanni Brotzu, Anna Maria Fadda, Maria Letizia Manca, Thomas Manca, Francesca Marongiu, Monica Campisi, Francesca Consolaro. A liposome-based formulation containing equol, dihomo-γ-linolenic acid and propionyl-l-carnitine to prevent and treat hair loss: A prospective investigation.
Dermatologic therapy.
2019 01; 32(1):e12778. doi:
10.1111/dth.12778. [PMID: 30371981] - Anna Fickler, Stefanie Staats, Stéphanie Céline Michl, Mario Hasler, Gerald Rimbach, Carsten Schulz. Combination of Dietary Ahiflower Oil and Equol Enhances Long-Chain Polyunsaturated Fatty Acid Levels in Rainbow Trout Tissues.
Lipids.
2018 11; 53(11-12):1069-1083. doi:
10.1002/lipd.12117. [PMID: 30723899] - Remi Yoshikata, Khin Zay Yar Myint, Hiroaki Ohta. Effects of Equol Supplement on Bone and Cardiovascular Parameters in Middle-Aged Japanese Women: A Prospective Observational Study.
Journal of alternative and complementary medicine (New York, N.Y.).
2018 Jul; 24(7):701-708. doi:
10.1089/acm.2018.0050. [PMID: 29722549] - Li Gao, Ke-Xin Wang, Nan-Nan Zhang, Jia-Qi Li, Xue-Mei Qin, Xiu-Ling Wang. 1H Nuclear Magnetic Resonance Based Metabolomics Approach Reveals the Metabolic Mechanism of (-)-5-Hydroxy-equol against Hepatocellular Carcinoma Cells in Vitro.
Journal of proteome research.
2018 05; 17(5):1833-1843. doi:
10.1021/acs.jproteome.7b00853. [PMID: 29589762] - Pilar Gaya, Abel Sánchez-Jiménez, Ángela Peirotén, Margarita Medina, José Maria Landete. Incomplete metabolism of phytoestrogens by gut microbiota from children under the age of three.
International journal of food sciences and nutrition.
2018 May; 69(3):334-343. doi:
10.1080/09637486.2017.1353955. [PMID: 28728453] - Salvatore Caruso, Stefano Cianci, Valentina Fava, Agnese M C Rapisarda, Silvia Cutello, Antonio Cianci. Vaginal health of postmenopausal women on nutraceutical containing equol.
Menopause (New York, N.Y.).
2018 04; 25(4):430-435. doi:
10.1097/gme.0000000000001061. [PMID: 29315133] - Takashi Takeda, Tomomi Ueno, Shigeto Uchiyama, Masami Shiina. Premenstrual symptoms interference and equol production status in Japanese collegiate athletes: A cross-sectional study.
The journal of obstetrics and gynaecology research.
2018 Mar; 44(3):488-494. doi:
10.1111/jog.13552. [PMID: 29226551] - Gerson Hernandez, Liqin Zhao, Adrian A Franke, Yu-Ling Chen, Wendy J Mack, Roberta D Brinton, Lon S Schneider. Pharmacokinetics and safety profile of single-dose administration of an estrogen receptor β-selective phytoestrogenic (phytoSERM) formulation in perimenopausal and postmenopausal women.
Menopause (New York, N.Y.).
2018 02; 25(2):191-196. doi:
10.1097/gme.0000000000000984. [PMID: 28926513] - Yuki Ideno, Kunihiko Hayashi, Junko Nakajima-Shimada, Yoko Onizuka, Mikiko Kishi, Tomomi Ueno, Shigeto Uchiyama. Optimal cut-off value for equol-producing status in women: The Japan Nurses' Health Study urinary isoflavone concentration survey.
PloS one.
2018; 13(7):e0201318. doi:
10.1371/journal.pone.0201318. [PMID: 30048499] - Jeong Eun Kwon, Jaewon Lim, Inhye Kim, Donghyuk Kim, Se Chan Kang. Isolation and identification of new bacterial stains producing equol from Pueraria lobata extract fermentation.
PloS one.
2018; 13(2):e0192490. doi:
10.1371/journal.pone.0192490. [PMID: 29447179] - A Braune, M Blaut. Evaluation of inter-individual differences in gut bacterial isoflavone bioactivation in humans by PCR-based targeting of genes involved in equol formation.
Journal of applied microbiology.
2018 Jan; 124(1):220-231. doi:
10.1111/jam.13616. [PMID: 29055162] - Michiya Igase, Keiji Igase, Yasuharu Tabara, Yasumasa Ohyagi, Katsuhiko Kohara. Cross-sectional study of equol producer status and cognitive impairment in older adults.
Geriatrics & gerontology international.
2017 Nov; 17(11):2103-2108. doi:
10.1111/ggi.13029. [PMID: 28345266] - Jiaoyu Wang, Ling Li, Yeshi Yin, Zhuokan Gu, Rongyao Chai, Yanli Wang, Guochang Sun. Equol, a Clinically Important Metabolite, Inhibits the Development and Pathogenicity of Magnaporthe oryzae, the Causal Agent of Rice Blast Disease.
Molecules (Basel, Switzerland).
2017 Oct; 22(10):. doi:
10.3390/molecules22101799. [PMID: 29064450] - Hiroko Horiuchi, Atsuko Usami, Rie Shirai, Naoki Harada, Shinichi Ikushiro, Toshiyuki Sakaki, Yoshihisa Nakano, Hiroshi Inui, Ryoichi Yamaji. S-Equol Activates cAMP Signaling at the Plasma Membrane of INS-1 Pancreatic β-Cells and Protects against Streptozotocin-Induced Hyperglycemia by Increasing β-Cell Function in Male Mice.
The Journal of nutrition.
2017 09; 147(9):1631-1639. doi:
10.3945/jn.117.250860. [PMID: 28768836] - Keiko Wada, Tomomi Ueno, Shigeto Uchiyama, Yasuhiro Abiru, Michiko Tsuji, Kie Konishi, Fumi Mizuta, Yuko Goto, Takashi Tamura, Makoto Shiraki, Shinichi Iwasa, Chisato Nagata. Relationship of equol production between children aged 5-7 years and their mothers.
European journal of nutrition.
2017 Aug; 56(5):1911-1917. doi:
10.1007/s00394-016-1233-x. [PMID: 27256298] - Claudio Gardana, Paolo Simonetti. Long-term kinetics of daidzein and its main metabolites in human equol-producers after soymilk intake: identification of equol-conjugates by UPLC-orbitrap-MS and influence of the number of transforming bacteria on plasma kinetics.
International journal of food sciences and nutrition.
2017 Jun; 68(4):496-506. doi:
10.1080/09637486.2016.1256380. [PMID: 27851886] - Lindsey M Miller, Johanna W Lampe, Katherine M Newton, Gabrielle Gundersen, Sharon Fuller, Susan D Reed, Cara L Frankenfeld. Being overweight or obese is associated with harboring a gut microbial community not capable of metabolizing the soy isoflavone daidzein to O-desmethylangolensin in peri- and post-menopausal women.
Maturitas.
2017 May; 99(?):37-42. doi:
10.1016/j.maturitas.2017.02.006. [PMID: 28364866] - Lucía Guadamuro, Anja B Dohrmann, Christoph C Tebbe, Baltasar Mayo, Susana Delgado. Bacterial communities and metabolic activity of faecal cultures from equol producer and non-producer menopausal women under treatment with soy isoflavones.
BMC microbiology.
2017 04; 17(1):93. doi:
10.1186/s12866-017-1001-y. [PMID: 28415978] - Remi Yoshikata, Khin Z Myint, Hiroaki Ohta. Relationship between equol producer status and metabolic parameters in 743 Japanese women: equol producer status is associated with antiatherosclerotic conditions in women around menopause and early postmenopause.
Menopause (New York, N.Y.).
2017 02; 24(2):216-224. doi:
10.1097/gme.0000000000000743. [PMID: 27676633] - Elizabeth J Reverri, Carolyn M Slupsky, Darya O Mishchuk, Francene M Steinberg. Metabolomics reveals differences between three daidzein metabolizing phenotypes in adults with cardiometabolic risk factors.
Molecular nutrition & food research.
2017 01; 61(1):. doi:
10.1002/mnfr.201600132. [PMID: 27364093] - Vasudha Ahuja, Katsuyuki Miura, Abhishek Vishnu, Akira Fujiyoshi, Rhobert Evans, Maryam Zaid, Naoko Miyagawa, Takashi Hisamatsu, Aya Kadota, Tomonori Okamura, Hirotsugu Ueshima, Akira Sekikawa. Significant inverse association of equol-producer status with coronary artery calcification but not dietary isoflavones in healthy Japanese men.
The British journal of nutrition.
2017 01; 117(2):260-266. doi:
10.1017/s000711451600458x. [PMID: 28205492] - Takashi Takeda, Tomomi Ueno, Shigeto Uchiyama, Keizo Hiramatsu, Masami Shiina. Relation between premenstrual syndrome and equol-production status.
The journal of obstetrics and gynaecology research.
2016 Nov; 42(11):1575-1580. doi:
10.1111/jog.13073. [PMID: 27352905] - Francisco A Tomás-Barberán, María V Selma, Juan C Espín. Interactions of gut microbiota with dietary polyphenols and consequences to human health.
Current opinion in clinical nutrition and metabolic care.
2016 11; 19(6):471-476. doi:
10.1097/mco.0000000000000314. [PMID: 27490306] - Takashi Takeda. Additional data to 'Relation between premenstrual syndrome and equol-production status'.
The journal of obstetrics and gynaecology research.
2016 Nov; 42(11):1631. doi:
10.1111/jog.13125. [PMID: 27527369] - Yoshie Nagata, Yukiko Sugiyama, Fumimasa Fukuta, Akio Takayanagi, Naoya Masumori, Taiji Tsukamoto, Hiroshi Akasaka, Hirofumi Ohnishi, Shigeyuki Saitoh, Tetsuji Miura, Kaoru Moriyama, Hirokazu Tsuji, Hideyuki Akaza, Mitsuru Mori. Relationship of serum levels and dietary intake of isoflavone, and the novel bacterium Slackia sp. strain NATTS with the risk of prostate cancer: a case-control study among Japanese men.
International urology and nephrology.
2016 Sep; 48(9):1453-60. doi:
10.1007/s11255-016-1335-7. [PMID: 27262851] - Stefanie C Fleck, Mona I Churchwell, Daniel R Doerge, Justin G Teeguarden. Urine and serum biomonitoring of exposure to environmental estrogens II: Soy isoflavones and zearalenone in pregnant women.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2016 Sep; 95(?):19-27. doi:
10.1016/j.fct.2016.05.021. [PMID: 27255803] - Shungo Fujii, Nobuyuki Takahashi, Hirofumi Inoue, Shin-Ichi Katsumata, Yuji Kikkawa, Makoto Machida, Yoshiko Ishimi, Mariko Uehara. A combination of soy isoflavones and cello-oligosaccharides changes equol/O-desmethylangolensin production ratio and attenuates bone fragility in ovariectomized mice.
Bioscience, biotechnology, and biochemistry.
2016 Aug; 80(8):1632-5. doi:
10.1080/09168451.2016.1184559. [PMID: 27191709] - Charlotte Atkinson, Roberta M Ray, Wenjin Li, Ming-Gang Lin, Dao Li Gao, Jackilen Shannon, Helge Stalsberg, Peggy L Porter, Cara L Frankenfeld, Kristiina Wähälä, David B Thomas, Johanna W Lampe. Plasma equol concentration is not associated with breast cancer and fibrocystic breast conditions among women in Shanghai, China.
Nutrition research (New York, N.Y.).
2016 08; 36(8):863-71. doi:
10.1016/j.nutres.2016.03.008. [PMID: 27440541] - Chen Wang, Shiyi Zhang, Yuyin Zhou, Chong Huang, Di Mu, John P Giesy, Jianying Hu. Equol Induces Gonadal Intersex in Japanese Medaka (Oryzias latipes) at Environmentally Relevant Concentrations: Comparison with 17β-Estradiol.
Environmental science & technology.
2016 07; 50(14):7852-60. doi:
10.1021/acs.est.6b02211. [PMID: 27305592] - Shin-Ichi Katsumata, Maiko Fujioka, Shungo Fujii, Ken Takeda, Yoshiko Ishimi, Mariko Uehara. Kanamycin inhibits daidzein metabolism and abilities of the metabolites to prevent bone loss in ovariectomized mice.
BMC research notes.
2016 Jul; 9(?):334. doi:
10.1186/s13104-016-2139-7. [PMID: 27388904] - Yuko Tousen, Yu Matsumoto, Chiho Matsumoto, Yoriko Nishide, Yuya Nagahata, Isao Kobayashi, Yoshiko Ishimi. The combined effects of soya isoflavones and resistant starch on equol production and trabecular bone loss in ovariectomised mice.
The British journal of nutrition.
2016 07; 116(2):247-57. doi:
10.1017/s0007114516001537. [PMID: 27197747] - Motoi Tamura, Sachiko Hori, Hiroyuki Nakagawa, Satoshi Yamauchi, Takuya Sugahara. Effects of an equol-producing bacterium isolated from human faeces on isoflavone and lignan metabolism in mice.
Journal of the science of food and agriculture.
2016 Jul; 96(9):3126-32. doi:
10.1002/jsfa.7490. [PMID: 26455424] - Mohammad Talaei, Bee L Lee, Choon N Ong, Rob M van Dam, Jian M Yuan, Woon P Koh, An Pan. Urine phyto-oestrogen metabolites are not significantly associated with risk of type 2 diabetes: the Singapore Chinese health study.
The British journal of nutrition.
2016 05; 115(9):1607-15. doi:
10.1017/s0007114516000581. [PMID: 26949260] - S Persiani, F Sala, C Manzotti, M Colovic, M Zangarini, Y Donazzolo, B Barbetta, C Vitalini, G Giacovelli, C Benvenuti, L C Rovati. Evaluation of Levothyroxine Bioavailability after Oral Administration of a Fixed Combination of Soy Isoflavones in Post-menopausal Female Volunteers.
Drug research.
2016 Mar; 66(3):136-40. doi:
10.1055/s-0035-1555784. [PMID: 26125285] - Sara Hazim, Peter J Curtis, Manuel Y Schär, Luisa M Ostertag, Colin D Kay, Anne-Marie Minihane, Aedín Cassidy. Acute benefits of the microbial-derived isoflavone metabolite equol on arterial stiffness in men prospectively recruited according to equol producer phenotype: a double-blind randomized controlled trial.
The American journal of clinical nutrition.
2016 Mar; 103(3):694-702. doi:
10.3945/ajcn.115.125690. [PMID: 26843154] - Zhao-min Liu, Suzanne C Ho, Yu-ming Chen, Yao Jie Xie, Zhi-guan Huang, Wen-hua Ling. Research protocol: effect of natural S-equol on blood pressure and vascular function--a six-month randomized controlled trial among equol non-producers of postmenopausal women with prehypertension or untreated stage 1 hypertension.
BMC complementary and alternative medicine.
2016 Mar; 16(?):89. doi:
10.1186/s12906-016-1065-5. [PMID: 26928904] - Rafidah Hod, Wided Kouidhi, Mustafa Ali Mohd, Ruby Husain. Plasma isoflavones in Malaysian men according to vegetarianism and by age.
Asia Pacific journal of clinical nutrition.
2016; 25(1):89-96. doi:
10.6133/apjcn.2016.25.1.02. [PMID: 26965767] - Ting Zhang, Qin Hu, Linying Shi, Li Qin, Qianyong Zhang, Mantian Mi. Equol Attenuates Atherosclerosis in Apolipoprotein E-Deficient Mice by Inhibiting Endoplasmic Reticulum Stress via Activation of Nrf2 in Endothelial Cells.
PloS one.
2016; 11(12):e0167020. doi:
10.1371/journal.pone.0167020. [PMID: 27907038] - Joanna M Redmon, Binu Shrestha, Rosario Cerundolo, Michael H Court. Soy isoflavone metabolism in cats compared with other species: urinary metabolite concentrations and glucuronidation by liver microsomes.
Xenobiotica; the fate of foreign compounds in biological systems.
2016; 46(5):406-15. doi:
10.3109/00498254.2015.1086038. [PMID: 26366946] - Begoña Redruello, Lucía Guadamuro, Isabel Cuesta, Jorge R Álvarez-Buylla, Baltasar Mayo, Susana Delgado. A novel UHPLC method for the rapid and simultaneous determination of daidzein, genistein and equol in human urine.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2015 Nov; 1005(?):1-8. doi:
10.1016/j.jchromb.2015.09.029. [PMID: 26444491] - Gangadhara R Sareddy, Ratna K Vadlamudi. Cancer therapy using natural ligands that target estrogen receptor beta.
Chinese journal of natural medicines.
2015 Nov; 13(11):801-807. doi:
10.1016/s1875-5364(15)30083-2. [PMID: 26614454] - Z-M Liu, S C Ho, Y-M Chen, B Tomlinson, S Ho, K To, J Woo. Effect of whole soy and purified daidzein on ambulatory blood pressure and endothelial function--a 6-month double-blind, randomized controlled trial among Chinese postmenopausal women with prehypertension.
European journal of clinical nutrition.
2015 Oct; 69(10):1161-8. doi:
10.1038/ejcn.2015.24. [PMID: 25782428] - Markus Lipovac, Angelika Pfitscher, Stefanie Hobiger, Thomas Laschitz, Martin Imhof, Peter Chedraui, Alois Jungbauer. Red clover isoflavone metabolite bioavailability is decreased after fructooligosaccharide supplementation.
Fitoterapia.
2015 Sep; 105(?):93-101. doi:
10.1016/j.fitote.2015.06.011. [PMID: 26073948] - Lisa Y Cho, Jae Jeong Yang, Kwang-Pil Ko, Seung Hyun Ma, Aesun Shin, Bo Youl Choi, Hyun Ja Kim, Dong Soo Han, Kyu Sang Song, Yong Sung Kim, Soung-Hoon Chang, Hai-Rim Shin, Daehee Kang, Keun-Young Yoo, Sue K Park. Gene polymorphisms in the ornithine decarboxylase-polyamine pathway modify gastric cancer risk by interaction with isoflavone concentrations.
Gastric cancer : official journal of the International Gastric Cancer Association and the Japanese Gastric Cancer Association.
2015 Jul; 18(3):495-503. doi:
10.1007/s10120-014-0396-5. [PMID: 25079701] - Baogang Xie, Shuohua Zhang, Jie Liu, Xuejun Zhan, Daze Xie, Zhirong Zhang. Enhanced Estrogenic Activity of Soybean Isoflavones by Coadministration of Liuwei Dihuang Pills in Ovariectomized Rats.
Phytotherapy research : PTR.
2015 Jul; 29(7):1054-61. doi:
10.1002/ptr.5346. [PMID: 25826579] - Katherine M Newton, Susan D Reed, Shigeto Uchiyama, Conghui Qu, Tomomi Ueno, Soh Iwashita, Gabrielle Gunderson, Sharon Fuller, Johanna W Lampe. A cross-sectional study of equol producer status and self-reported vasomotor symptoms.
Menopause (New York, N.Y.).
2015 May; 22(5):489-95. doi:
10.1097/gme.0000000000000363. [PMID: 25380274] - Panida Loutchanwoot, Prayook Srivilai, Hubertus Jarry. The influence of equol on the hypothalamic-pituitary-thyroid axis and hepatic lipid metabolic parameters in adult male rats.
Life sciences.
2015 May; 128(?):1-7. doi:
10.1016/j.lfs.2015.02.002. [PMID: 25744395] - Kwang-Pil Ko, Cheong-Sik Kim, Younjhin Ahn, Seon-Joo Park, Yeon-Jeong Kim, Jae Kyung Park, Young-Khi Lim, Keun-Young Yoo, Sung Soo Kim. Plasma isoflavone concentration is associated with decreased risk of type 2 diabetes in Korean women but not men: results from the Korean Genome and Epidemiology Study.
Diabetologia.
2015 Apr; 58(4):726-35. doi:
10.1007/s00125-014-3463-x. [PMID: 25533387] - Subroto Acharjee, Jin-Rong Zhou, Tarec K Elajami, Francine K Welty. Effect of soy nuts and equol status on blood pressure, lipids and inflammation in postmenopausal women stratified by metabolic syndrome status.
Metabolism: clinical and experimental.
2015 Feb; 64(2):236-43. doi:
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