O-Desmethylangolensin (BioDeep_00001873926)

Main id: BioDeep_00000027904

 

PANOMIX_OTCML-2023


代谢物信息卡片


O-Desmethylangolensin

化学式: C15H14O4 (258.0892044)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C1=CC=C(C=C1)O)C(=O)C2=C(C=C(C=C2)O)O
InChI: InChI=1S/C15H14O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-9,16-18H,1H3

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
O-Desmethylangolensin is a metabolite of soy isoflavone, daidzein metabolized by gut microbiota. O-Desmethylangolensin possesses antioxidant activity[1][2].

同义名列表

1 个代谢物同义名

O-Desmethylangolensin



数据库引用编号

6 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

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0 个相关的物种来源信息

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  • 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。

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文献列表

  • Jing Sun, Hong Jiang, Weijing Wang, Xue Dong, Dongfeng Zhang. Associations of Urinary Phytoestrogen Concentrations with Sleep Disorders and Sleep Duration among Adults. Nutrients. 2020 Jul; 12(7):. doi: 10.3390/nu12072103. [PMID: 32708566]
  • 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]
  • Olivia Cardenas-Trowers, Isuzu Meyer, Holly E Richter, Ilana Addis, Alayne D Markland. Association of Urinary Phytoestrogens With Pelvic Organ Prolapse and Fecal Incontinence Symptoms in Postmenopausal Women. Female pelvic medicine & reconstructive surgery. 2019 Mar; 25(2):161-166. doi: 10.1097/spv.0000000000000661. [PMID: 30807421]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • C L Frankenfeld, C Atkinson, K Wähälä, J W Lampe. Obesity prevalence in relation to gut microbial environments capable of producing equol or O-desmethylangolensin from the isoflavone daidzein. European journal of clinical nutrition. 2014 Apr; 68(4):526-30. doi: 10.1038/ejcn.2014.23. [PMID: 24569543]
  • Claudio Gardana, Enrica Canzi, Paolo Simonetti. R(-)-O-desmethylangolensin is the main enantiomeric form of daidzein metabolite produced by human in vitro and in vivo. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Mar; 953-954(?):30-7. doi: 10.1016/j.jchromb.2014.01.048. [PMID: 24561352]
  • Ling Shi, Heather Harker Ryan, Emily Jones, Tiffany A Moore Simas, Alice H Lichtenstein, Qi Sun, Laura L Hayman. Urinary isoflavone concentrations are inversely associated with cardiometabolic risk markers in pregnant U.S. women. The Journal of nutrition. 2014 Mar; 144(3):344-51. doi: 10.3945/jn.113.184069. [PMID: 24381220]
  • Eun Jeong Choi, Gun-Hee Kim. The antioxidant activity of daidzein metabolites, O‑desmethylangolensin and equol, in HepG2 cells. Molecular medicine reports. 2014 Jan; 9(1):328-32. doi: 10.3892/mmr.2013.1752. [PMID: 24154619]
  • Zhao-min Liu, Suzanne C Ho, Yu-ming Chen, Jun Liu, Jean Woo. Cardiovascular risks in relation to daidzein metabolizing phenotypes among Chinese postmenopausal women. PloS one. 2014; 9(2):e87861. doi: 10.1371/journal.pone.0087861. [PMID: 24533060]
  • Michael E Rybak, Maya R Sternberg, Christine M Pfeiffer. Sociodemographic and lifestyle variables are compound- and class-specific correlates of urine phytoestrogen concentrations in the U.S. population. The Journal of nutrition. 2013 Jun; 143(6):986S-94S. doi: 10.3945/jn.112.172981. [PMID: 23596167]
  • Eun Jeong Choi, Jae-In Lee, Gun-Hee Kim. Anticancer effects of O-desmethylangolensin are mediated through cell cycle arrest at the G2/M phase and mitochondrial-dependent apoptosis in Hep3B human hepatocellular carcinoma cells. International journal of molecular medicine. 2013 Mar; 31(3):726-30. doi: 10.3892/ijmm.2013.1230. [PMID: 23314756]
  • Monika Eichholzer, Aline Richard, Esther Walser-Domjan, Jakob Linseisen, Sabine Rohrmann. Urinary phytoestrogen levels and frailty in older American women of the National Health and Nutrition Examination Survey (NHANES) 1999-2002: a cross-sectional study. Annals of nutrition & metabolism. 2013; 63(4):269-76. doi: 10.1159/000356453. [PMID: 24334908]
  • Charlotte Atkinson, Katherine M Newton, Mellissa Yong, Frank Z Stanczyk, Kim C Westerlind, Lin Li, Johanna W Lampe. Daidzein-metabolizing phenotypes in relation to bone density and body composition among premenopausal women in the United States. Metabolism: clinical and experimental. 2012 Dec; 61(12):1678-82. doi: 10.1016/j.metabol.2012.05.012. [PMID: 22819530]
  • Cara L Frankenfeld. O-desmethylangolensin: the importance of equol's lesser known cousin to human health. Advances in nutrition (Bethesda, Md.). 2011 Jul; 2(4):317-24. doi: 10.3945/an.111.000539. [PMID: 22332073]
  • Cara L Frankenfeld. Dairy consumption is a significant correlate of urinary equol concentration in a representative sample of US adults. The American journal of clinical nutrition. 2011 May; 93(5):1109-16. doi: 10.3945/ajcn.111.011825. [PMID: 21389178]
  • Kaiping Guo, Bo Zhang, Chaogang Chen, Shigeto Uchiyama, Tomomi Ueno, Yuming Chen, Yixiang Su. Daidzein-metabolising phenotypes in relation to serum lipids and uric acid in adults in Guangzhou, China. The British journal of nutrition. 2010 Jul; 104(1):118-24. doi: 10.1017/s0007114510000279. [PMID: 20205965]
  • Shin-ichiro Yokoyama, Toshio Niwa, Toshihiko Osawa, Tohru Suzuki. Characterization of an O-desmethylangolensin-producing bacterium isolated from human feces. Archives of microbiology. 2010 Jan; 192(1):15-22. doi: 10.1007/s00203-009-0524-5. [PMID: 19904524]
  • 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]
  • 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]
  • 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]
  • Charlotte Atkinson, Katherine M Newton, Erin J Aiello Bowles, Mellissa Yong, Johanna W Lampe. Demographic, anthropometric, and lifestyle factors and dietary intakes in relation to daidzein-metabolizing phenotypes among premenopausal women in the United States. The American journal of clinical nutrition. 2008 Mar; 87(3):679-87. doi: 10.1093/ajcn/87.3.679. [PMID: 18326607]
  • 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]
  • 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]
  • Cara L Frankenfeld, Anne McTiernan, Wendy K Thomas, Kristin LaCroix, Lynda McVarish, Victoria L Holt, Stephen M Schwartz, Johanna W Lampe. Postmenopausal bone mineral density in relation to soy isoflavone-metabolizing phenotypes. Maturitas. 2006 Feb; 53(3):315-24. doi: 10.1016/j.maturitas.2005.05.016. [PMID: 16019168]
  • Cara L Frankenfeld, Charlotte Atkinson, Wendy K Thomas, Alex Gonzalez, Tuija Jokela, Kristiina Wähälä, Stephen M Schwartz, Shuying S Li, Johanna W Lampe. High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart. The British journal of nutrition. 2005 Dec; 94(6):873-6. doi: 10.1079/bjn20051565. [PMID: 16351761]
  • Tammy E Hedlund, Paul D Maroni, Paul G Ferucci, Robert Dayton, Stephen Barnes, Kenneth Jones, Ray Moore, Lorraine G Ogden, Kristiina Wähälä, Holly M Sackett, Karen J Gray. Long-term dietary habits affect soy isoflavone metabolism and accumulation in prostatic fluid in caucasian men. The Journal of nutrition. 2005 Jun; 135(6):1400-6. doi: 10.1093/jn/135.6.1400. [PMID: 15930444]
  • Karel Decroos, Steffi Vanhemmens, Sofie Cattoir, Nico Boon, Willy Verstraete. Isolation and characterisation of an equol-producing mixed microbial culture from a human faecal sample and its activity under gastrointestinal conditions. Archives of microbiology. 2005 Jan; 183(1):45-55. doi: 10.1007/s00203-004-0747-4. [PMID: 15578160]
  • Cara L Frankenfeld, Anne McTiernan, Erin J Aiello, Wendy K Thomas, Kristin LaCroix, Judy Schramm, Stephen M Schwartz, Victoria L Holt, Johanna W Lampe. Mammographic density in relation to daidzein-metabolizing phenotypes in overweight, postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2004 Jul; 13(7):1156-62. doi: NULL. [PMID: 15247126]
  • Leane Hoey, Ian R Rowland, Antony S Lloyd, Don B Clarke, Helen Wiseman. Influence of soya-based infant formula consumption on isoflavone and gut microflora metabolite concentrations in urine and on faecal microflora composition and metabolic activity in infants and children. The British journal of nutrition. 2004 Apr; 91(4):607-16. doi: 10.1079/bjn20031083. [PMID: 15035688]
  • Cara L Frankenfeld, Anne McTiernan, Shelley S Tworoger, Charlotte Atkinson, Wendy K Thomas, Frank Z Stanczyk, Santica M Marcovina, David S Weigle, Noel S Weiss, Victoria L Holt, Stephen M Schwartz, Johanna W Lampe. Serum steroid hormones, sex hormone-binding globulin concentrations, and urinary hydroxylated estrogen metabolites in post-menopausal women in relation to daidzein-metabolizing phenotypes. The Journal of steroid biochemistry and molecular biology. 2004 Apr; 88(4-5):399-408. doi: 10.1016/j.jsbmb.2004.01.006. [PMID: 15145450]
  • Philip B Grace, James I Taylor, Nigel P Botting, Tara Fryatt, Mark F Oldfield, Sheila A Bingham. Quantification of isoflavones and lignans in urine using gas chromatography/mass spectrometry. Analytical biochemistry. 2003 Apr; 315(1):114-21. doi: 10.1016/s0003-2697(02)00707-8. [PMID: 12672419]
  • 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]
  • Y Arai, M Uehara, Y Sato, M Kimira, A Eboshida, H Adlercreutz, S Watanabe. Comparison of isoflavones among dietary intake, plasma concentration and urinary excretion for accurate estimation of phytoestrogen intake. Journal of epidemiology. 2000 Mar; 10(2):127-35. doi: 10.2188/jea.10.127. [PMID: 10778038]
  • W Zheng, Q Dai, L J Custer, X O Shu, W Q Wen, F Jin, A A Franke. Urinary excretion of isoflavonoids and the risk of breast cancer. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1999 Jan; 8(1):35-40. doi: NULL. [PMID: 9950237]
  • A Zeleniuch-Jacquotte, H Adlercreutz, A Akhmedkhanov, P Toniolo. Reliability of serum measurements of lignans and isoflavonoid phytoestrogens over a two-year period. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1998 Oct; 7(10):885-9. doi: NULL. [PMID: 9796633]
  • A M Hutchins, J L Slavin, J W Lampe. Urinary isoflavonoid phytoestrogen and lignan excretion after consumption of fermented and unfermented soy products. Journal of the American Dietetic Association. 1995 May; 95(5):545-51. doi: 10.1016/s0002-8223(95)00149-2. [PMID: 7722188]
  • H Adlercreutz, H Markkanen, S Watanabe. Plasma concentrations of phyto-oestrogens in Japanese men. Lancet (London, England). 1993 Nov; 342(8881):1209-10. doi: 10.1016/0140-6736(93)92188-y. [PMID: 7901532]
  • H Adlercreutz, T Fotsis, C Bannwart, K Wähälä, G Brunow, T Hase. Isotope dilution gas chromatographic-mass spectrometric method for the determination of lignans and isoflavonoids in human urine, including identification of genistein. Clinica chimica acta; international journal of clinical chemistry. 1991 Jul; 199(3):263-78. doi: 10.1016/0009-8981(91)90120-2. [PMID: 1663006]
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