Dihydrodaidzein (BioDeep_00000000475)
Secondary id: BioDeep_00000270119, BioDeep_00000380897, BioDeep_00000396678
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite
代谢物信息卡片
(R)-23-Dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
化学式: C15H12O4 (256.0736)
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 Homo sapiens(plant) 25.19%
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
- ChEBI: CHEBI:75842
- KEGG: C90417
- PubChem: 176907
- HMDB: HMDB0005760
- LipidMAPS: LMPK12050447
- MeSH: dihydrodaidzein
- ChemIDplus: 0017238050
- MetaCyc: 2-HYDROXY-23-DIHYDRODAIDZEIN
- KNApSAcK: C00009533
- foodb: FDB023752
- chemspider: 154076
- CAS: 879559-75-8
- CAS: 58865-02-4
- CAS: 17238-05-0
- MetaboLights: MTBLC75842
- RefMet: Dihydrodaidzein
- medchemexpress: HY-N1461
- medchemexpress: HY-N4200
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
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Fitoterapia.
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International journal of epidemiology.
2012 Oct; 41(5):1367-75. doi:
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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.
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Chemical & pharmaceutical bulletin.
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Carcinogenesis.
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Experimental gerontology.
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Hormones and behavior.
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Prostate cancer and prostatic diseases.
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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]
