Dihydrogenistein (BioDeep_00000009905)

 

Secondary id: BioDeep_00001874643

human metabolite Endogenous blood metabolite


代谢物信息卡片


2,3-Dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

化学式: C15H12O5 (272.0684702)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.52%

分子结构信息

SMILES: C1C(C(=O)C2=C(C=C(C=C2O1)O)O)C3=CC=C(C=C3)O
InChI: InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-6,11,16-18H,7H2

描述信息

Dihydrogenistein is a metabolite of the soy isoflavone genistin (the glycoside conjugate of genistein) by intestinal bacteria. Isoflavones are one of the three major classes of phytoestrogens; phytoestrogens are a diverse group of plant-derived compounds that structurally and functionally mimic mammalian estrogen. The isoflavone genistin is one of the most prevalent in soy foods. They are biologically inactive; once ingested, they are cleaved by glucosidases to "aglycones", genistein. Epidemiological studies have associated high soy intake with a lowered risk for certain hormone-dependent disease. Many studies reveal that the incidence of prostate cancer and breast cancer is much lower in Asian people in comparison to people from the West and, and the prevailing contribution to this difference has been attributed to the diet. Soy foods and soy-derived products which contain abundant isoflavones are consumed in large quantities by Asian people. In vitro, isoflavone metabolites have dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. (PMID: 17499260, 16965913) [HMDB]. Dihydrogenistein is a biomarker for the consumption of soy beans and other soy products.
Dihydrogenistein is a metabolite of the soy isoflavone genistin (the glycoside conjugate of genistein) by intestinal bacteria. Isoflavones are one of the three major classes of phytoestrogens; phytoestrogens are a diverse group of plant-derived compounds that structurally and functionally mimic mammalian estrogen. The isoflavone genistin is one of the most prevalent in soy foods. They are biologically inactive; once ingested, they are cleaved by glucosidases to "aglycones", genistein. Epidemiological studies have associated high soy intake with a lowered risk for certain hormone-dependent disease. Many studies reveal that the incidence of prostate cancer and breast cancer is much lower in Asian people in comparison to people from the West and, and the prevailing contribution to this difference has been attributed to the diet. Soy foods and soy-derived products which contain abundant isoflavones are consumed in large quantities by Asian people. In vitro, isoflavone metabolites have dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. (PMID: 17499260, 16965913). Dihydrogenistein is a biomarker for the consumption of soy beans and other soy products.

同义名列表

7 个代谢物同义名

2,3-Dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one; 4,5,7-Trihydroxyisoflavan-4-one; 4,5,7-Trihydroxy-isoflavanone; 4,5,7-Trihydroxyisoflavanone; (S)-Dihydrogenistein; Dihydrogenistein



数据库引用编号

14 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

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)

1 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

  • Yan Lin, Yi Kuang, Kai Li, Shuang Wang, Shuai Ji, Kuan Chen, Wei Song, Xue Qiao, Min Ye. Nrf2 activators from Glycyrrhiza inflata and their hepatoprotective activities against CCl4-induced liver injury in mice. Bioorganic & medicinal chemistry. 2017 10; 25(20):5522-5530. doi: 10.1016/j.bmc.2017.08.018. [PMID: 28835349]
  • 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]
  • Koji Kato, Hiroyuki Kusuhara, Yuji Kumagai, Ichiro Ieiri, Haruyuki Mori, Sumito Ito, Yasuhiro Nakai, Kazuya Maeda, Yuichi Sugiyama. Association of multidrug resistance-associated protein 2 single nucleotide polymorphism rs12762549 with the basal plasma levels of phase II metabolites of isoflavonoids in healthy Japanese individuals. Pharmacogenetics and genomics. 2012 May; 22(5):344-54. doi: 10.1097/fpc.0b013e3283517012. [PMID: 22407408]
  • 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]
  • Irena Baranowska, Sylwia Magiera, Jacek Baranowski. UHPLC method for the simultaneous determination of β-blockers, isoflavones and their metabolites in human urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Mar; 879(9-10):615-26. doi: 10.1016/j.jchromb.2011.01.026. [PMID: 21345747]
  • 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]
  • Annett Braune, Ronald Maul, Nils Helge Schebb, Sabine E Kulling, Michael Blaut. The red clover isoflavone irilone is largely resistant to degradation by the human gut microbiota. Molecular nutrition & food research. 2010 Jul; 54(7):929-38. doi: 10.1002/mnfr.200900233. [PMID: 19998384]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • Begoña Cerdá, Paula Periago, Juan Carlos Espín, Francisco A Tomás-Barberán. Identification of urolithin a as a metabolite produced by human colon microflora from ellagic acid and related compounds. Journal of agricultural and food chemistry. 2005 Jul; 53(14):5571-6. doi: 10.1021/jf050384i. [PMID: 15998116]
  • Anna H Wu, Mimi C Yu, Chui-Chen Tseng, Nathan C Twaddle, Daniel R Doerge. Plasma isoflavone levels versus self-reported soy isoflavone levels in Asian-American women in Los Angeles County. Carcinogenesis. 2004 Jan; 25(1):77-81. doi: 10.1093/carcin/bgg189. [PMID: 14555615]
  • Maija Kaamanen, Herman Adlercreutz, Matti Jauhiainen, Matti J Tikkanen. Accumulation of genistein and lipophilic genistein derivatives in lipoproteins during incubation with human plasma in vitro. Biochimica et biophysica acta. 2003 Mar; 1631(2):147-52. doi: 10.1016/s1388-1981(02)00363-3. [PMID: 12633680]
  • Hesso Farhan, Kristiina Wähälä, Heide S Cross. Genistein inhibits vitamin D hydroxylases CYP24 and CYP27B1 expression in prostate cells. The Journal of steroid biochemistry and molecular biology. 2003 Mar; 84(4):423-9. doi: 10.1016/s0960-0760(03)00063-3. [PMID: 12732287]
  • Adrian A Franke, Laurie J Custer, Lynne R Wilkens, Loïc Le Le Marchand, Abraham M Y Nomura, Marc T Goodman, Laurence N Kolonel. Liquid chromatographic-photodiode array mass spectrometric analysis of dietary phytoestrogens from human urine and blood. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2002 Sep; 777(1-2):45-59. doi: 10.1016/s1570-0232(02)00216-7. [PMID: 12270199]
  • Yuliya Dobrydneva, Roy L Williams, Gary Z Morris, Peter F Blackmore. Dietary phytoestrogens and their synthetic structural analogues as calcium channel blockers in human platelets. Journal of cardiovascular pharmacology. 2002 Sep; 40(3):399-410. doi: 10.1097/00005344-200209000-00009. [PMID: 12198326]
  • Rafaëlla L'homme, Elke Brouwers, Nawaf Al-Maharik, O Lapcík, R Hampl, Heikki Mikola, K Wähälä, Herman Adlercreutz. Time-resolved fluoroimmunoassay of plasma and urine O-desmethylangolensin. The Journal of steroid biochemistry and molecular biology. 2002 Aug; 81(4-5):353-61. doi: 10.1016/s0960-0760(02)00073-0. [PMID: 12361725]
  • N G Coldham, C Darby, M Hows, L J King, A Q Zhang, M J Sauer. Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism. Xenobiotica; the fate of foreign compounds in biological systems. 2002 Jan; 32(1):45-62. doi: 10.1080/00498250110085809. [PMID: 11820509]
  • T Yasuda, J Ueda, K Ohsawa. Urinary metabolites of genistein administered orally to rats. Chemical & pharmaceutical bulletin. 2001 Nov; 49(11):1495-7. doi: 10.1248/cpb.49.1495. [PMID: 11724248]
  • K Morito, T Hirose, J Kinjo, T Hirakawa, M Okawa, T Nohara, S Ogawa, S Inoue, M Muramatsu, Y Masamune. Interaction of phytoestrogens with estrogen receptors alpha and beta. Biological & pharmaceutical bulletin. 2001 Apr; 24(4):351-6. doi: 10.1248/bpb.24.351. [PMID: 11305594]
  • T D Lund, T W West, L Y Tian, L H Bu, D L Simmons, K D Setchell, H Adlercreutz, E D Lephart. Visual spatial memory is enhanced in female rats (but inhibited in males) by dietary soy phytoestrogens. BMC neuroscience. 2001; 2(?):20. doi: 10.1186/1471-2202-2-20. [PMID: 11801187]