Dihydrodaidzein (BioDeep_00000000475)

 

Secondary id: BioDeep_00000270119, BioDeep_00000380897, BioDeep_00000396678

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


(R)-23-Dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

化学式: C15H12O4 (256.0735552)
中文名称: (S)-二氢大豆苷元, 二氢大豆苷元, 二氢7-羟基-3-(4-羟苯基)-4-苯并吡喃酮, 二氢黄豆苷元
谱图信息: 最多检出来源 Viridiplantae(plant) 0.24%

分子结构信息

SMILES: c1(ccc2c(c1)OC[C@@H](C2=O)c1ccc(cc1)O)O
InChI: InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2

描述信息

Dihydrodaidzein is one of the most prominent dietary phytoestrogens. Dietary phytoestrogens have been implicated in the prevention of chronic diseases (PMID:12270199). Dihydrodaidzein is a biomarker for the consumption of soy beans and other soy products.
Dihydrodaidzein is a hydroxyisoflavanone that is isoflavanone carrying two hydroxy substituents located at positions 4 and 7. It has a role as a metabolite.
A hydroxyisoflavanone that is isoflavanone carrying two hydroxy substituents located at positions 4 and 7.
Dihydrodaidzein is one of the most prominent dietary phytoestrogens.
S-Dihydrodaidzein is the (S)-enantiomer of dihydrodaidzein which is one of the most prominent dietary phytoestrogens[1][2].

同义名列表

19 个代谢物同义名

(R)-23-Dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one; 7-hydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one; 7-hydroxy-3-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one; 7-hydroxy-3-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one; ( inverted exclamation markA)-Dihydrodaidzein; 7-hydroxy-3-(4-hydroxyphenyl)chroman-4-one; 7-Hydroxy-3-(4-hydroxyphenyl)-4-chromanone; Isoflavanone, 4,7-dihydroxy-; 4,7-dihydroxy-Isoflavanone; 7,4-Dihydroxyisoflavanone; Dihydrodaidzein (keto); (+/-)-Dihydrodaidzein; Dihydro Daidzein; DihydroDaidzein; Dihydrodazein; (±)-Dihydrodaidzein; S-Dihydrodaidzein; Dihydrodaidzein



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

  • coumestrol biosynthesis: (S)-dihydrodaidzein + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ (3R)-2'-hydroxydihydrodaidzein + H2O + an oxidized [NADPH-hemoprotein reductase]

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

  • 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]
  • 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]
  • 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]
  • Xianglan Zhang, Yu-Tang Gao, Gong Yang, Honglan Li, Qiuyin Cai, Yong-Bing Xiang, Bu-Tian Ji, Adrian A Franke, Wei Zheng, Xiao-Ou Shu. Urinary isoflavonoids and risk of coronary heart disease. International journal of epidemiology. 2012 Oct; 41(5):1367-75. doi: 10.1093/ije/dys130. [PMID: 22927214]
  • Ming Wang, Hui Zhao, Xiu-Ling Wang, Hong-Lei Zhang, Qing-Hong Hao. [C-ring cleavage of liquiritigenin extracted from licorice roots by an oxygen-tolerant bovine rumen bacterium strain Aeroto-Niu-O16]. Yao xue xue bao = Acta pharmaceutica Sinica. 2012 May; 47(5):664-9. doi: . [PMID: 22812014]
  • Takeshi Aso, Shigeto Uchiyama, Yasuhiro Matsumura, Makoto Taguchi, Masahiro Nozaki, Kiyoshi Takamatsu, Bunpei Ishizuka, Toshiro Kubota, Hideki Mizunuma, Hiroaki Ohta. A natural S-equol supplement alleviates hot flushes and other menopausal symptoms in equol nonproducing postmenopausal Japanese women. Journal of women's health (2002). 2012 Jan; 21(1):92-100. doi: 10.1089/jwh.2011.2753. [PMID: 21992596]
  • Motoi Tamura, Sachiko Hori, Chigusa Hoshi, Hiroyuki Nakagawa. Effects of rice bran oil on the intestinal microbiota and metabolism of isoflavones in adult mice. International journal of molecular sciences. 2012; 13(8):10336-49. doi: 10.3390/ijms130810336. [PMID: 22949864]
  • Katherine M Whitehouse-Tedd, Nicholas J Cave, Claudia E Ugarte, Lucy A Waldron, Jeevan K Prasain, Alireza Arabshahi, Stephen Barnes, David G Thomas. Dietary isoflavone absorption, excretion, and metabolism in captive cheetahs (Acinonyx jubatus). Journal of zoo and wildlife medicine : official publication of the American Association of Zoo Veterinarians. 2011 Dec; 42(4):658-70. doi: 10.1638/2011-0060.1. [PMID: 22204061]
  • Ewelina Szliszka, Wojciech Krol. Soy isoflavones augment the effect of TRAIL-mediated apoptotic death in prostate cancer cells. Oncology reports. 2011 Sep; 26(3):533-41. doi: 10.3892/or.2011.1332. [PMID: 21637922]
  • Takeshi Yoneda, Tomomi Ueno, Shigeto Uchiyama. 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 (New York, N.Y.). 2011 Jul; 18(7):814-20. doi: 10.1097/gme.0b013e318208fb0d. [PMID: 21451423]
  • Yuko Tousen, Junko Ezaki, Yasuhiro Fujii, Tomomi Ueno, Mamoru Nishimuta, Yoshiko Ishimi. Natural S-equol decreases bone resorption in postmenopausal, non-equol-producing Japanese women: a pilot randomized, placebo-controlled trial. Menopause (New York, N.Y.). 2011 May; 18(5):563-74. doi: 10.1097/gme.0b013e3181f85aa7. [PMID: 21252728]
  • Motoi Tamura, Sachiko Hori, Hiroyuki Nakagawa. Lactobacillus rhamnosus JCM 2771: impact on metabolism of isoflavonoids in the fecal flora from a male equol producer. Current microbiology. 2011 May; 62(5):1632-7. doi: 10.1007/s00284-011-9904-6. [PMID: 21365446]
  • Jeffry B Plomley, Richard L Jackson, Richard J Schwen, Jeffrey S Greiwe. Development of chiral liquid chromatography-tandem mass spectrometry isotope dilution methods for the determination of unconjugated and total S-equol in human plasma and urine. Journal of pharmaceutical and biomedical analysis. 2011 Apr; 55(1):125-34. doi: 10.1016/j.jpba.2010.12.031. [PMID: 21247718]
  • Gisela H Degen, Meinolf Blaszkewicz, Lijie Shi, Anette E Buyken, Thomas Remer. Urinary isoflavone phytoestrogens in German children and adolescents--a longitudinal examination in the DONALD cohort. Molecular nutrition & food research. 2011 Mar; 55(3):359-67. doi: 10.1002/mnfr.201000325. [PMID: 20938994]
  • Corinne C Hoerger, Arnaud P Praplan, Linus Becker, Felix E Wettstein, Konrad Hungerbühler, Thomas D Bucheli. Quantification of five isoflavones and coumestrol in various solid agroenvironmental matrices using ¹³c₃-labeled internal standards. Journal of agricultural and food chemistry. 2011 Feb; 59(3):847-56. doi: 10.1021/jf1039266. [PMID: 21204535]
  • Pamela J Magee. Is equol production beneficial to health?. The Proceedings of the Nutrition Society. 2011 Feb; 70(1):10-8. doi: 10.1017/s0029665110003940. [PMID: 21092366]
  • Richard L Jackson, Jeffrey S Greiwe, Pankaj B Desai, Richard J Schwen. Single-dose and steady-state pharmacokinetic studies of S-equol, a potent nonhormonal, estrogen receptor β-agonist being developed for the treatment of menopausal symptoms. Menopause (New York, N.Y.). 2011 Feb; 18(2):185-93. doi: 10.1097/gme.0b013e3181e9779c. [PMID: 21341397]
  • Trent D Lund, Crystal Blake, Lihong Bu, Amy N Hamaker, Edwin D Lephart. Equol an isoflavonoid: potential for improved prostate health, in vitro and in vivo evidence. Reproductive biology and endocrinology : RB&E. 2011 Jan; 9(?):4. doi: 10.1186/1477-7827-9-4. [PMID: 21232127]
  • Takayuki Minekawa, Akira Kambegawa, Kumiko Shindome, Hiroshi Ohkuma, Katsushi Abe, Hiroaki Maekawa, Hidetoshi Arakawa. Development of bioluminescent enzyme immunoassay for s-equol using firefly luciferase and its application to the assessment of equol-producer status. Chemical & pharmaceutical bulletin. 2011; 59(1):84-7. doi: 10.1248/cpb.59.84. [PMID: 21212552]
  • Maria D Jackson, Norma D McFarlane-Anderson, Garfield A Simon, Franklyn I Bennett, Susan P Walker. Urinary phytoestrogens and risk of prostate cancer in Jamaican men. Cancer causes & control : CCC. 2010 Dec; 21(12):2249-57. doi: 10.1007/s10552-010-9648-9. [PMID: 20924663]
  • Ting-Fu Ko, Hui-Su Tsai, Shu-Mei Lin, Chi-Dong Liu, Show-Phon Learn, Robin Y Y Chiou. GC-MS determined distribution of urinary equol producers as affected by age, gender, and repeated ingestions of soymilk. Journal of food science. 2010 Nov; 75(9):H306-10. doi: 10.1111/j.1750-3841.2010.01860.x. [PMID: 21535605]
  • Yulin Ma, Jennifer C Sullivan, Derek A Schreihofer. Dietary genistein and equol (4', 7 isoflavandiol) reduce oxidative stress and protect rats against focal cerebral ischemia. American journal of physiology. Regulatory, integrative and comparative physiology. 2010 Sep; 299(3):R871-7. doi: 10.1152/ajpregu.00031.2010. [PMID: 20631292]
  • Jihye Kim, Hye Jin Kim, Hyojee Joung, Min Kyung Park, Shanji Li, YoonJu Song, Adrian A Franke, Hee-Young Paik. Overnight urinary excretion of isoflavones as an indicator for dietary isoflavone intake in Korean girls of pubertal age. The British journal of nutrition. 2010 Sep; 104(5):709-15. doi: 10.1017/s0007114510000978. [PMID: 20385037]
  • Adrian A Franke, Sandra M Hebshi, Ian Pagano, Naoko Kono, Wendy J Mack, Howard N Hodis. Urine accurately reflects circulating isoflavonoids and ascertains compliance during soy intervention. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2010 Jul; 19(7):1775-83. doi: 10.1158/1055-9965.epi-10-0116. [PMID: 20615889]
  • Selin Bolca, Willy Verstraete. Microbial equol production attenuates colonic methanogenesis and sulphidogenesis in vitro. Anaerobe. 2010 Jun; 16(3):247-52. doi: 10.1016/j.anaerobe.2010.03.002. [PMID: 20298796]
  • S Sehmisch, J Uffenorde, S Maehlmeyer, M Tezval, H Jarry, K M Stuermer, E K Stuermer. Evaluation of bone quality and quantity in osteoporotic mice--the effects of genistein and equol. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2010 May; 17(6):424-30. doi: 10.1016/j.phymed.2009.10.004. [PMID: 20036112]
  • Nadine M Brown, Carrie A Belles, Stephanie L Lindley, Linda D Zimmer-Nechemias, Xueheng Zhao, David P Witte, Mi-Ok Kim, Kenneth D R Setchell. The chemopreventive action of equol enantiomers in a chemically induced animal model of breast cancer. Carcinogenesis. 2010 May; 31(5):886-93. doi: 10.1093/carcin/bgq025. [PMID: 20110282]
  • Ciska Wyns, Selin Bolca, Denis De Keukeleire, Arne Heyerick. Development of a high-throughput LC/APCI-MS method for the determination of thirteen phytoestrogens including gut microbial metabolites in human urine and serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Apr; 878(13-14):949-56. doi: 10.1016/j.jchromb.2010.02.022. [PMID: 20299290]
  • Jeevan K Prasain, Alireza Arabshahi, D Ray Moore, Gail A Greendale, J Michael Wyss, Stephen Barnes. Simultaneous determination of 11 phytoestrogens in human serum using a 2 min liquid chromatography/tandem mass spectrometry method. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Apr; 878(13-14):994-1002. doi: 10.1016/j.jchromb.2010.02.032. [PMID: 20346741]
  • Hirokazu Tsuji, Kaoru Moriyama, Koji Nomoto, Naoto Miyanaga, Hideyuki Akaza. Isolation and characterization of the equol-producing bacterium Slackia sp. strain NATTS. Archives of microbiology. 2010 Apr; 192(4):279-87. doi: 10.1007/s00203-010-0546-z. [PMID: 20237913]
  • Anke Thielemann, Wolfgang Wuttke, Marcus Wuttke, Dana Seidlova-Wuttke. Comparison of urodynamic effects of phytoestrogens equol, puerarin and genistein with these of estradiol 17beta in ovariectomized rats. Experimental gerontology. 2010 Feb; 45(2):129-37. doi: 10.1016/j.exger.2009.11.003. [PMID: 19903517]
  • Mohammad Tezval, Stephan Sehmisch, Dana Seidlová-Wuttke, Thomas Rack, Leila Kolios, Wolfgang Wuttke, Klaus Michael Stuermer, Ewa Klara Stuermer. Changes in the histomorphometric and biomechanical properties of the proximal femur of ovariectomized rat after treatment with the phytoestrogens genistein and equol. Planta medica. 2010 Feb; 76(3):235-40. doi: 10.1055/s-0029-1186136. [PMID: 19764010]
  • Ralph W deVere White, Alexander Tsodikov, Eschelle C Stapp, Stephanie E Soares, Hajime Fujii, Robert M Hackman. Effects of a high dose, aglycone-rich soy extract on prostate-specific antigen and serum isoflavone concentrations in men with localized prostate cancer. Nutrition and cancer. 2010; 62(8):1036-43. doi: 10.1080/01635581.2010.492085. [PMID: 21058191]
  • Baohua Liu, Liqiang Qin, Aiping Liu, Shigeto Uchiyama, Tomomi Ueno, Xuetuo Li, Peiyu Wang. Prevalence of the equol-producer phenotype and its relationship with dietary isoflavone and serum lipids in healthy Chinese adults. Journal of epidemiology. 2010; 20(5):377-84. doi: 10.2188/jea.je20090185. [PMID: 20671375]
  • Eeva A Mustonen, Mikko Tuori, Ilkka Saastamoinen, Juhani Taponen, Kristiina Wähälä, Hannu Saloniemi, Aila Vanhatalo. Equol in milk of dairy cows is derived from forage legumes such as red clover. The British journal of nutrition. 2009 Dec; 102(11):1552-6. doi: 10.1017/s0007114509990857. [PMID: 19622190]
  • Selin Bolca, Ciska Wyns, Sam Possemiers, Herman Depypere, Denis De Keukeleire, Marc Bracke, Willy Verstraete, Arne Heyerick. Cosupplementation of isoflavones, prenylflavonoids, and lignans alters human exposure to phytoestrogen-derived 17beta-estradiol equivalents. The Journal of nutrition. 2009 Dec; 139(12):2293-300. doi: 10.3945/jn.109.113639. [PMID: 19864398]
  • Motoi Tamura, Sachiko Hori, Hiroyuki Nakagawa. Dietary cholesterol lowers plasma and cecal equol concentrations in mice. Nutrition research (New York, N.Y.). 2009 Dec; 29(12):882-7. doi: 10.1016/j.nutres.2009.10.014. [PMID: 19963162]
  • Claudio Gardana, Enrica Canzi, Paolo Simonetti. The role of diet in the metabolism of daidzein by human faecal microbiota sampled from Italian volunteers. The Journal of nutritional biochemistry. 2009 Dec; 20(12):940-7. doi: 10.1016/j.jnutbio.2008.08.006. [PMID: 19071008]
  • Ho Seok Kwak, So Young Park, Mi Gyeong Kim, Chang Hoon Yim, Hyun Koo Yoon, Ki Ok Han. Marked individual variation in isoflavone metabolism after a soy challenge can modulate the skeletal effect of isoflavones in premenopausal women. Journal of Korean medical science. 2009 Oct; 24(5):867-73. doi: 10.3346/jkms.2009.24.5.867. [PMID: 19794985]
  • Eun Jeong Choi. Chronic equol administration attenuates the antioxidant defense system and causes apoptosis in the mouse brain. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2009 Aug; 47(8):1779-84. doi: 10.1016/j.fct.2009.04.036. [PMID: 19409442]
  • Charlotte Atkinson, Katherine M Newton, Erin J Aiello Bowles, Constance D Lehman, Frank Z Stanczyk, Kim C Westerlind, Lin Li, Johanna W Lampe. Daidzein-metabolizing phenotypes in relation to mammographic breast density among premenopausal women in the United States. Breast cancer research and treatment. 2009 Aug; 116(3):587-94. doi: 10.1007/s10549-008-0199-7. [PMID: 18821061]
  • Christopher D Gardner, Beibei Oelrich, Jenny P Liu, David Feldman, Adrian A Franke, James D Brooks. Prostatic soy isoflavone concentrations exceed serum levels after dietary supplementation. The Prostate. 2009 May; 69(7):719-26. doi: 10.1002/pros.20922. [PMID: 19180569]
  • Raewyn C Poulsen, Du Toit Loots, Paul J Moughan, Marlena C Kruger. Ileal and faecal digestibility of daidzein and genistein and plasma bioavailability of these isoflavones and their bioactive metabolites in the ovariectomised rat. Molecular nutrition & food research. 2009 May; 53 Suppl 1(?):S27-35. doi: 10.1002/mnfr.200800080. [PMID: 19156712]
  • Charlotte Carreau, Gilles Flouriot, Catherine Bennetau-Pelissero, Mylène Potier. Respective contribution exerted by AF-1 and AF-2 transactivation functions in estrogen receptor alpha induced transcriptional activity by isoflavones and equol: consequence on breast cancer cell proliferation. Molecular nutrition & food research. 2009 May; 53(5):652-8. doi: 10.1002/mnfr.200800061. [PMID: 19065587]
  • Estatira Sepehr, Gerard M Cooke, Patrick Robertson, G Sarwar Gilani. Effect of glycosidation of isoflavones on their bioavailability and pharmacokinetics in aged male rats. Molecular nutrition & food research. 2009 May; 53 Suppl 1(?):S16-26. doi: 10.1002/mnfr.200800170. [PMID: 19437481]
  • Eun Jeong Choi, Gun-Hee Kim. Hepatoprotective effects of daidzein against 7,12-dimetylbenz[a]anthracene-induced oxidative stress in mice. International journal of molecular medicine. 2009 May; 23(5):659-64. doi: 10.3892/ijmm_00000177. [PMID: 19360325]
  • Leila Kolios, Stephan Sehmisch, Florian Daub, Thomas Rack, Mohammed Tezval, Klaus Michael Stuermer, Ewa Klara Stuermer. Equol but not genistein improves early metaphyseal fracture healing in osteoporotic rats. Planta medica. 2009 Apr; 75(5):459-65. doi: 10.1055/s-0029-1185380. [PMID: 19241330]
  • Kelly R Walsh, Sara J Haak, Nathan D Fastinger, Torsten Bohn, Qingguo Tian, Donald C Mahan, Steven J Schwartz, Mark L Failla. Gastrointestinal absorption and metabolism of soy isoflavonoids in ileal-canulated swine. Molecular nutrition & food research. 2009 Feb; 53(2):277-86. doi: 10.1002/mnfr.200800014. [PMID: 18837469]
  • Heather B Patisaul, Katherine T Burke, Ruth E Hinkle, Heather B Adewale, Damian Shea. Systemic administration of diarylpropionitrile (DPN) or phytoestrogens does not affect anxiety-related behaviors in gonadally intact male rats. Hormones and behavior. 2009 Feb; 55(2):319-28. doi: 10.1016/j.yhbeh.2008.11.004. [PMID: 19071129]
  • Naoko Ishiwata, Melissa K Melby, Shoichi Mizuno, Shaw Watanabe. New equol supplement for relieving menopausal symptoms: randomized, placebo-controlled trial of Japanese women. Menopause (New York, N.Y.). 2009 Jan; 16(1):141-8. doi: 10.1097/gme.0b013e31818379fa. [PMID: 19131846]
  • M Tanaka, K Fujimoto, Y Chihara, K Torimoto, T Yoneda, N Tanaka, A Hirayama, N Miyanaga, H Akaza, Y Hirao. Isoflavone supplements stimulated the production of serum equol and decreased the serum dihydrotestosterone levels in healthy male volunteers. Prostate cancer and prostatic diseases. 2009; 12(3):247-52. doi: 10.1038/pcan.2009.10. [PMID: 19597532]
  • Carey E Gleason, Cynthia M Carlsson, Jodi H Barnet, Sarah A Meade, Kenneth D R Setchell, Craig S Atwood, Sterling C Johnson, Michele L Ries, Sanjay Asthana. A preliminary study of the safety, feasibility and cognitive efficacy of soy isoflavone supplements in older men and women. Age and ageing. 2009 Jan; 38(1):86-93. doi: 10.1093/ageing/afn227. [PMID: 19054783]
  • Lu Wang, Haitian Zhao, Cuilin Cheng, Fangqin Xie. [Effect of equol of a isoflavone metabolite on menopausal symptoms]. Wei sheng yan jiu = Journal of hygiene research. 2009 Jan; 38(1):117-9. doi: NULL. [PMID: 19267091]
  • Charlotte Atkinson, Katherine M Newton, Frank Z Stanczyk, Kim C Westerlind, Lin Li, Johanna W Lampe. Daidzein-metabolizing phenotypes in relation to serum hormones and sex hormone binding globulin, and urinary estrogen metabolites in premenopausal women in the United States. Cancer causes & control : CCC. 2008 Dec; 19(10):1085-93. doi: 10.1007/s10552-008-9172-3. [PMID: 18478336]
  • Angelika Pfitscher, Evelyne Reiter, Alois Jungbauer. Receptor binding and transactivation activities of red clover isoflavones and their metabolites. The Journal of steroid biochemistry and molecular biology. 2008 Nov; 112(1-3):87-94. doi: 10.1016/j.jsbmb.2008.08.007. [PMID: 18809497]
  • Shin-ichiro Yokoyama, Tohru Suzuki. Isolation and characterization of a novel equol-producing bacterium from human feces. Bioscience, biotechnology, and biochemistry. 2008 Oct; 72(10):2660-6. doi: 10.1271/bbb.80329. [PMID: 18838805]
  • Izabela Woclawek-Potocka, Mariusz Krzysztof Piskula, Mamadou Bah, Marta Jolanta Siemieniuch, Anna Korzekwa, Edyta Brzezicka, Dariusz Jan Skarzynski. Concentrations of isoflavones and their metabolites in the blood of pregnant and non-pregnant heifers fed soy bean. The Journal of reproduction and development. 2008 Oct; 54(5):358-63. doi: 10.1262/jrd.20013. [PMID: 18678989]
  • Takuya Ohtomo, Mariko Uehara, José Luis Peñalvo, Herman Adlercreutz, Shin-ichi Katsumata, Kazuharu Suzuki, Ken Takeda, Ritsuko Masuyama, Yoshiko Ishimi. Comparative activities of daidzein metabolites, equol and O-desmethylangolensin, on bone mineral density and lipid metabolism in ovariectomized mice and in osteoclast cell cultures. European journal of nutrition. 2008 Aug; 47(5):273-9. doi: 10.1007/s00394-008-0723-x. [PMID: 18622636]
  • Jong-Sik Jin, Tomohiro Nishihata, Nobuko Kakiuchi, Masao Hattori. Biotransformation of C-glucosylisoflavone puerarin to estrogenic (3S)-equol in co-culture of two human intestinal bacteria. Biological & pharmaceutical bulletin. 2008 Aug; 31(8):1621-5. doi: 10.1248/bpb.31.1621. [PMID: 18670101]
  • Gertraud Maskarinec, Kirsten Watts, Jamie Kagihara, Sandra M Hebshi, Adrian A Franke. Urinary isoflavonoid excretion is similar after consuming soya milk and miso soup in Japanese-American women. The British journal of nutrition. 2008 Aug; 100(2):424-9. doi: 10.1017/s0007114508898686. [PMID: 18275624]
  • Hei-Jen Jou, Shiao-Chi Wu, Fang-Wei Chang, Pei-Ying Ling, Kung Shen Chu, Wen-Huey Wu. Effect of intestinal production of equol on menopausal symptoms in women treated with soy isoflavones. International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics. 2008 Jul; 102(1):44-9. doi: 10.1016/j.ijgo.2008.01.028. [PMID: 18395723]
  • John M Pendleton, Winston W Tan, Satoshi Anai, Myron Chang, Wei Hou, Kathleen T Shiverick, Charles J Rosser. Phase II trial of isoflavone in prostate-specific antigen recurrent prostate cancer after previous local therapy. BMC cancer. 2008 May; 8(?):132. doi: 10.1186/1471-2407-8-132. [PMID: 18471323]
  • Toshinari Maruo, Mitsuo Sakamoto, Chiaki Ito, Toshiya Toda, Yoshimi Benno. Adlercreutzia equolifaciens gen. nov., sp. nov., an equol-producing bacterium isolated from human faeces, and emended description of the genus Eggerthella. International journal of systematic and evolutionary microbiology. 2008 May; 58(Pt 5):1221-7. doi: 10.1099/ijs.0.65404-0. [PMID: 18450717]
  • Zhuo-Teng Yu, Wen Yao, Wei-Yun Zhu. Isolation and identification of equol-producing bacterial strains from cultures of pig faeces. FEMS microbiology letters. 2008 May; 282(1):73-80. doi: 10.1111/j.1574-6968.2008.01108.x. [PMID: 18328079]
  • Dominik Rachoń, Anne Menche, Tina Vortherms, Dana Seidlová-Wuttke, Wolfgang Wuttke. Effects of dietary equol administration on the mammary gland in ovariectomized Sprague-Dawley rats. Menopause (New York, N.Y.). 2008 Mar; 15(2):340-5. doi: 10.1097/gme.0b013e318093df58. [PMID: 17693898]
  • Brunhild M Halm, Adrian A Franke, Leslie A Ashburn, Sandra M Hebshi, Lynne R Wilkens. Oral antibiotics decrease urinary isoflavonoid excretion in children after soy consumption. Nutrition and cancer. 2008; 60(1):14-22. doi: 10.1080/01635580701586747. [PMID: 18444131]
  • Brigitte Chanteranne, Francesco Branca, A Kaardinal, K Wahala, Véronique Braesco, Philippe Ladroite, Fred Brouns, Véronique Coxam. Food matrix and isoflavones bioavailability in early post menopausal women: a European clinical study. Clinical interventions in aging. 2008; 3(4):711-8. doi: 10.2147/cia.s4085. [PMID: 19281063]
  • K Fujimoto, M Tanaka, Y Hirao, Y Nagata, M Mori, N Miyanaga, H Akaza, W-J Kim. Age-stratified serum levels of isoflavones and proportion of equol producers in Japanese and Korean healthy men. Prostate cancer and prostatic diseases. 2008; 11(3):252-7. doi: 10.1038/sj.pcan.4501030. [PMID: 18180805]
  • Chisato Nagata, Tomomi Ueno, Shigeto Uchiyama, Yasuko Nagao, Satoru Yamamoto, Chiken Shibuya, Yoshitomo Kashiki, Hiroyuki Shimizu. Dietary and lifestyle correlates of urinary excretion status of equol in Japanese women. Nutrition and cancer. 2008; 60(1):49-54. doi: 10.1080/01635580701525885. [PMID: 18444135]
  • Barbara J Fuhrman, Barbara E Teter, Maddalena Barba, Celia Byrne, Adalberto Cavalleri, Brydon J Grant, Peter J Horvath, Daniele Morelli, Elisabetta Venturelli, Paola C Muti. Equol status modifies the association of soy intake and mammographic density in a sample of postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2008 Jan; 17(1):33-42. doi: 10.1158/1055-9965.epi-07-0193. [PMID: 18199709]
  • Dominik Rachoń, Dana Seidlová-Wuttke, Tina Vortherms, Wolfgang Wuttke. Effects of dietary equol administration on ovariectomy induced bone loss in Sprague-Dawley rats. Maturitas. 2007 Nov; 58(3):308-15. doi: 10.1016/j.maturitas.2007.09.005. [PMID: 17961939]
  • Dominik Rachoń, Tina Vortherms, Dana Seidlová-Wuttke, Wolfgang Wuttke. Effects of dietary equol on body weight gain, intra-abdominal fat accumulation, plasma lipids, and glucose tolerance in ovariectomized Sprague-Dawley rats. Menopause (New York, N.Y.). 2007 Sep; 14(5):925-32. doi: 10.1097/gme.0b013e31802d979b. [PMID: 17414092]
  • Jian Wu, Jun Oka, Junko Ezaki, Takuya Ohtomo, Tomomi Ueno, Shigeto Uchiyama, Toshiya Toda, Mariko Uehara, Yoshiko Ishimi. Possible role of equol status in the effects of isoflavone on bone and fat mass in postmenopausal Japanese women: a double-blind, randomized, controlled trial. Menopause (New York, N.Y.). 2007 Sep; 14(5):866-74. doi: 10.1097/gme.0b013e3180305299. [PMID: 17464237]
  • C L Heald, M R Ritchie, C Bolton-Smith, M S Morton, F E Alexander. Phyto-oestrogens and risk of prostate cancer in Scottish men. The British journal of nutrition. 2007 Aug; 98(2):388-96. doi: 10.1017/s0007114507700703. [PMID: 17403269]
  • Estatira Sepehr, Gerard Cooke, Patrick Robertson, G Sarwar Gilani. Bioavailability of soy isoflavones in rats Part I: application of accurate methodology for studying the effects of gender and source of isoflavones. Molecular nutrition & food research. 2007 Jul; 51(7):799-812. doi: 10.1002/mnfr.200700083. [PMID: 17576640]
  • Stefan Moors, Meinolf Blaszkewicz, Hermann M Bolt, Gisela H Degen. Simultaneous determination of daidzein, equol, genistein and bisphenol A in human urine by a fast and simple method using SPE and GC-MS. Molecular nutrition & food research. 2007 Jul; 51(7):787-98. doi: 10.1002/mnfr.200600289. [PMID: 17579895]
  • Lijuan Chen, Xia Zhao, Linyu Fang, David E Games. Quantitative determination of acetyl glucoside isoflavones and their metabolites in human urine using combined liquid chromatography-mass spectrometry. Journal of chromatography. A. 2007 Jun; 1154(1-2):103-10. doi: 10.1016/j.chroma.2007.03.010. [PMID: 17499260]
  • Fatemeh Rafii, Leslie D Jackson, Ian Ross, Thomas M Heinze, Sherry M Lewis, Anane Aidoo, Lascelles Lyn-Cook, Mugimane Manjanatha. Metabolism of daidzein by fecal bacteria in rats. Comparative medicine. 2007 Jun; 57(3):282-6. doi: NULL. [PMID: 17605343]
  • Hassanali Vatanparast, Philip D Chilibeck. Does the effect of soy phytoestrogens on bone in postmenopausal women depend on the equol-producing phenotype?. Nutrition reviews. 2007 Jun; 65(6 Pt 1):294-9. doi: 10.1301/nr.2007.jun.294-299. [PMID: 17605306]
  • Duncan C S Talbot, Richard M Ogborne, Tony Dadd, Herman Adlercreutz, Geoff Barnard, Susanne Bugel, Fortune Kohen, Sandra Marlin, Jerry Piron, Aedin Cassidy, Jonathan Powell. Monoclonal antibody-based time-resolved fluorescence immunoassays for daidzein, genistein, and equol in blood and urine: application to the Isoheart intervention study. Clinical chemistry. 2007 Apr; 53(4):748-56. doi: 10.1373/clinchem.2006.075077. [PMID: 17317887]
  • D Rachoń, T Vortherms, D Seidlová-Wuttke, W Wuttke. Effects of dietary equol on the pituitary of the ovariectomized rats. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2007 Apr; 39(4):256-61. doi: 10.1055/s-2007-973074. [PMID: 17447162]
  • Sang-Ah Lee, Wanqing Wen, Yong-Bing Xiang, Stephen Barnes, Dake Liu, Qiuyin Cai, Wei Zheng, Xiao Ou Shu. Assessment of dietary isoflavone intake among middle-aged Chinese men. The Journal of nutrition. 2007 Apr; 137(4):1011-6. doi: 10.1093/jn/137.4.1011. [PMID: 17374669]
  • Sébastien Vergne, Karine Titier, Virginie Bernard, Julien Asselineau, Marlène Durand, Valérie Lamothe, Mylène Potier, Paul Perez, Jacques Demotes-Mainard, Philippe Chantre, Nicholas Moore, Catherine Bennetau-Pelissero, Patrick Sauvant. Bioavailability and urinary excretion of isoflavones in humans: effects of soy-based supplements formulation and equol production. Journal of pharmaceutical and biomedical analysis. 2007 Mar; 43(4):1488-94. doi: 10.1016/j.jpba.2006.10.006. [PMID: 17110073]
  • D Tsangalis, G Wilcox, N P Shah, A E J McGill, L Stojanovska. Urinary excretion of equol by postmenopausal women consuming soymilk fermented by probiotic bifidobacteria. European journal of clinical nutrition. 2007 Mar; 61(3):438-41. doi: 10.1038/sj.ejcn.1602530. [PMID: 17021598]
  • Motoi Tamura, Tojiro Tsushida, Kazuki Shinohara. Isolation of an isoflavone-metabolizing, Clostridium-like bacterium, strain TM-40, from human faeces. Anaerobe. 2007 Feb; 13(1):32-5. doi: 10.1016/j.anaerobe.2006.10.001. [PMID: 17113326]
  • Shin-Ichiro Yokoyama, Tsuyoshi Kuzuguchi. Rapid and convenient detection of urinary equol by thin-layer chromatography. Journal of nutritional science and vitaminology. 2007 Feb; 53(1):43-7. doi: 10.3177/jnsv.53.43. [PMID: 17484378]
  • G Maskarinec, R Yamakawa, S Hebshi, A A Franke. Urinary isoflavonoid excretion and soy consumption in three generations of Japanese women in Hawaii. European journal of clinical nutrition. 2007 Feb; 61(2):255-61. doi: 10.1038/sj.ejcn.1602511. [PMID: 16929241]
  • Michael C Hall, Bridget O'Brien, Tom McCormack. Equol producer status, salivary estradiol profile and urinary excretion of isoflavones in Irish Caucasian women, following ingestion of soymilk. Steroids. 2007 Jan; 72(1):64-70. doi: 10.1016/j.steroids.2006.10.010. [PMID: 17157887]
  • Mary H McMullen, Jill M Hamilton-Reeves, Melissa J L Bonorden, Kerry E Wangen, William R Phipps, Joellen M Feirtag, Mindy S Kurzer. Consumption of Lactobacillus acidophilus and Bifidobacterium longum does not alter phytoestrogen metabolism and plasma hormones in men: a pilot study. Journal of alternative and complementary medicine (New York, N.Y.). 2006 Nov; 12(9):887-94. doi: 10.1089/acm.2006.12.887. [PMID: 17109580]
  • Chisato Nagata, Shinichi Iwasa, Makoto Shiraki, Tomomi Ueno, Shigeto Uchiyama, Koji Urata, Yukari Sahashi, Hiroyuki Shimizu. Associations among maternal soy intake, isoflavone levels in urine and blood samples, and maternal and umbilical hormone concentrations (Japan). Cancer causes & control : CCC. 2006 Nov; 17(9):1107-13. doi: 10.1007/s10552-006-0044-4. [PMID: 17006716]
  • Jie Shen, Melanie White, Alan J Husband, Brett D Hambly, Shisan Bao. Phytoestrogen derivatives differentially inhibit arterial neointimal proliferation in a mouse model. European journal of pharmacology. 2006 Oct; 548(1-3):123-8. doi: 10.1016/j.ejphar.2006.07.050. [PMID: 16950243]
  • Sheeja Joy, Richard C M Siow, David J Rowlands, Marko Becker, Amanda W Wyatt, Philip I Aaronson, Clive W Coen, Imre Kallo, Ron Jacob, Giovanni E Mann. The isoflavone Equol mediates rapid vascular relaxation: Ca2+-independent activation of endothelial nitric-oxide synthase/Hsp90 involving ERK1/2 and Akt phosphorylation in human endothelial cells. The Journal of biological chemistry. 2006 Sep; 281(37):27335-45. doi: 10.1074/jbc.m602803200. [PMID: 16840783]
  • Charles E Wood, Susan E Appt, Thomas B Clarkson, Adrian A Franke, Cynthia J Lees, Daniel R Doerge, J Mark Cline. Effects of high-dose soy isoflavones and equol on reproductive tissues in female cynomolgus monkeys. Biology of reproduction. 2006 Sep; 75(3):477-86. doi: 10.1095/biolreprod.106.052142. [PMID: 16723506]
  • Akiko Tamura, Megumi Nishimukai, Norihiro Shigematsu, Hiroshi Hara. Supplementation of difructose anhydride III enhanced elevation of plasma equol concentrations and lowered plasma total cholesterol in isoflavone-fed rats. The British journal of nutrition. 2006 Sep; 96(3):442-9. doi: . [PMID: 16925848]
  • N Védrine, J Mathey, C Morand, M Brandolini, M-J Davicco, L Guy, C Rémésy, V Coxam, C Manach. One-month exposure to soy isoflavones did not induce the ability to produce equol in postmenopausal women. European journal of clinical nutrition. 2006 Sep; 60(9):1039-45. doi: 10.1038/sj.ejcn.1602415. [PMID: 16482068]
  • Eun Jeong Choi. The prooxidant, rather than antioxidant, acts of daidzein in vivo and in vitro: daidzein suppresses glutathione metabolism. European journal of pharmacology. 2006 Aug; 542(1-3):162-9. doi: 10.1016/j.ejphar.2006.05.020. [PMID: 16797001]
  • Tak Yi Lau, Lai K Leung. Soya isoflavones suppress phorbol 12-myristate 13-acetate-induced COX-2 expression in MCF-7 cells. The British journal of nutrition. 2006 Jul; 96(1):169-76. doi: 10.1079/bjn20061639. [PMID: 16870006]
  • Steven Cooper, John R Latendresse, Daniel R Doerge, Nathan C Twaddle, Xin Fu, K Barry Delclos. Dietary modulation of p-nonylphenol-induced polycystic kidneys in male Sprague-Dawley rats. Toxicological sciences : an official journal of the Society of Toxicology. 2006 Jun; 91(2):631-42. doi: 10.1093/toxsci/kfj171. [PMID: 16554316]
  • Izabela Woclawek-Potocka, Aleksandra Bober, Anna Korzekwa, Kiyoshi Okuda, Dariusz J Skarzynski. Equol and para-ethyl-phenol stimulate prostaglandin F(2alpha) secretion in bovine corpus luteum: intracellular mechanisms of action. Prostaglandins & other lipid mediators. 2006 May; 79(3-4):287-97. doi: 10.1016/j.prostaglandins.2006.03.003. [PMID: 16647642]