Estra-1(10),2,4-triene-2,3,17-triol (BioDeep_00000841192)
代谢物信息卡片
Estra-1(10),2,4-triene-2,3,17-triol
化学式: C18H24O3 (288.1725354)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)O)O
InChI: InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3
描述信息
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
同义名列表
1 个代谢物同义名
相关代谢途径
Reactome(0)
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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)
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PharmGKB(0)
0 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
- Nhung Le, Melissa Cregger, Veronica Brown, Julio Loret de Mola, Pamela Bremer, Lyn Nguyen, Kathleen Groesch, Teresa Wilson, Paula Diaz-Sylvester, Andrea Braundmeier-Fleming. Association of microbial dynamics with urinary estrogens and estrogen metabolites in patients with endometriosis.
PloS one.
2021; 16(12):e0261362. doi:
10.1371/journal.pone.0261362. [PMID: 34914785] - Emil Jakobsen, Sofie C Lange, Jens V Andersen, Claus Desler, Henriette F Kihl, Michaela C Hohnholt, Malin H Stridh, Lene J Rasmussen, Helle S Waagepetersen, Lasse K Bak. The inhibitors of soluble adenylate cyclase 2-OHE, KH7, and bithionol compromise mitochondrial ATP production by distinct mechanisms.
Biochemical pharmacology.
2018 09; 155(?):92-101. doi:
10.1016/j.bcp.2018.06.023. [PMID: 29940175] - Peter Thomas. Role of G-protein-coupled estrogen receptor (GPER/GPR30) in maintenance of meiotic arrest in fish oocytes.
The Journal of steroid biochemistry and molecular biology.
2017 03; 167(?):153-161. doi:
10.1016/j.jsbmb.2016.12.005. [PMID: 28007532] - Chieh-Ming Fang, Ming-Chun Ku, Che-Kai Chang, Huei-Chen Liang, Tzu-Fan Wang, Chih-Hsing Wu, Shu-Hui Chen. Identification of Endogenous Site-specific Covalent Binding of Catechol Estrogens to Serum Proteins in Human Blood.
Toxicological sciences : an official journal of the Society of Toxicology.
2015 Dec; 148(2):433-42. doi:
10.1093/toxsci/kfv190. [PMID: 26342215] - W L Gao, L S Wu, J H Zi, B Wu, Y Z Li, Y C Song, D Z Cai. Measurement of serum estrogen and estrogen metabolites in pre- and postmenopausal women with osteoarthritis using high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas.
2015 Feb; 48(2):146-53. doi:
10.1590/1414-431x20144129. [PMID: 25410577] - Hui-Hui Li, Ying-Jie Zhao, Yan Li, Cai-Feng Dai, Sheikh O Jobe, Xing-Sheng Yang, Xing-Fu Li, Manish S Patankar, Ronald R Magness, Jing Zheng. Estradiol 17β and its metabolites stimulate cell proliferation and antagonize ascorbic acid-suppressed cell proliferation in human ovarian cancer cells.
Reproductive sciences (Thousand Oaks, Calif.).
2014 Jan; 21(1):102-11. doi:
10.1177/1933719113492211. [PMID: 23757313] - R J Aitken, T B Smith, T Lord, L Kuczera, A J Koppers, N Naumovski, H Connaughton, M A Baker, G N De Iuliis. On methods for the detection of reactive oxygen species generation by human spermatozoa: analysis of the cellular responses to catechol oestrogen, lipid aldehyde, menadione and arachidonic acid.
Andrology.
2013 Mar; 1(2):192-205. doi:
10.1111/j.2047-2927.2012.00056.x. [PMID: 23316012] - Xin Sun, Jagadeesan Nair, Jakob Linseisen, Robert W Owen, Helmut Bartsch. Lipid peroxidation and DNA adduct formation in lymphocytes of premenopausal women: Role of estrogen metabolites and fatty acid intake.
International journal of cancer.
2012 Nov; 131(9):1983-90. doi:
10.1002/ijc.27479. [PMID: 22322480] - Sharon Anderson, Terry T Oyama, Jessie N Lindsley, William E Schutzer, Douglas R Beard, Vincent H Gattone, Radko Komers. 2-Hydroxyestradiol slows progression of experimental polycystic kidney disease.
American journal of physiology. Renal physiology.
2012 Mar; 302(5):F636-45. doi:
10.1152/ajprenal.00265.2011. [PMID: 22160773] - Daniel W Sepkovic, Laura Raucci, Johann Stein, Antoine D Carlisle, Karen Auborn, H Barbara Ksieski, Themba Nyirenda, H Leon Bradlow. 3,3'-Diindolylmethane increases serum interferon-γ levels in the K14-HPV16 transgenic mouse model for cervical cancer.
In vivo (Athens, Greece).
2012 Mar; 26(2):207-11. doi:
NULL. [PMID: 22351660] - P S Tofovic, B M Rosado, K R Dubey, Z Mi, Edwin K Jackson. Effects of estradiol metabolites on cAMP production and degradation.
Prilozi.
2009 Jul; 30(1):5-24. doi:
. [PMID: 19736528] - Kenneth R Hallows, Huamin Wang, Robert S Edinger, Michael B Butterworth, Nicholas M Oyster, Hui Li, Jochen Buck, Lonny R Levin, John P Johnson, Núria M Pastor-Soler. Regulation of epithelial Na+ transport by soluble adenylyl cyclase in kidney collecting duct cells.
The Journal of biological chemistry.
2009 Feb; 284(9):5774-83. doi:
10.1074/jbc.m805501200. [PMID: 19126549] - Xiaoying Qiao, Kristi R McConnell, Raouf A Khalil. Sex steroids and vascular responses in hypertension and aging.
Gender medicine.
2008; 5 Suppl A(?):S46-64. doi:
10.1016/j.genm.2008.03.006. [PMID: 18395683] - Melissa J Wentz, Shao-Qing Shi, Leili Shi, Salama A Salama, Hassan M Harirah, Hala Fouad, Robert E Garfield, Ayman Al-Hendy. Treatment with an inhibitor of catechol-O-methyltransferase activity reduces preterm birth and impedes cervical resistance to stretch in pregnant rats.
Reproduction (Cambridge, England).
2007 Dec; 134(6):831-9. doi:
10.1530/rep-07-0245. [PMID: 18042640] - Heather Greenlee, Yu Chen, Geoffrey C Kabat, Qiao Wang, Muhammad G Kibriya, Irina Gurvich, Daniel W Sepkovic, H Leon Bradlow, Ruby T Senie, Regina M Santella, Habibul Ahsan. Variants in estrogen metabolism and biosynthesis genes and urinary estrogen metabolites in women with a family history of breast cancer.
Breast cancer research and treatment.
2007 Mar; 102(1):111-7. doi:
10.1007/s10549-006-9308-7. [PMID: 16850246] - Christopher M Masi, Louise C Hawkley, Jarett D Berry, John T Cacioppo. Estrogen metabolites and systolic blood pressure in a population-based sample of postmenopausal women.
The Journal of clinical endocrinology and metabolism.
2006 Mar; 91(3):1015-20. doi:
10.1210/jc.2005-2339. [PMID: 16384842] - J R Muñoz-Castañeda, I Túnez, M C Muñoz, I Bujalance, J Muntané, P Montilla. Effect of catecholestrogen administration during adriamycin-induced cardiomyopathy in ovariectomized rat.
Free radical research.
2005 Sep; 39(9):943-8. doi:
10.1080/10715760400013805. [PMID: 16087475] - C S A Markides, J G Liehr. Specific binding of 4-hydroxyestradiol to mouse uterine protein: evidence of a physiological role for 4-hydroxyestradiol.
The Journal of endocrinology.
2005 May; 185(2):235-42. doi:
10.1677/joe.1.06014. [PMID: 15845916] - V K Turan, R I Sanchez, J J Li, S A Li, K R Reuhl, P E Thomas, A H Conney, M A Gallo, F C Kauffman, S Mesia-Vela. The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone.
The Journal of endocrinology.
2004 Oct; 183(1):91-9. doi:
10.1677/joe.1.05802. [PMID: 15525577] - P H Roos, S Tschirbs, A Hack, P Welge, M Wilhelm. Different mechanisms of handling ingested polycyclic aromatic hydrocarbons in mammalian species: organ-specific response patterns of CYP1A1-induction after oral intake of PAH-contaminated soils.
Xenobiotica; the fate of foreign compounds in biological systems.
2004 Sep; 34(9):781-95. doi:
10.1080/00498250400010880. [PMID: 15742974] - Lefteris C Zacharia, Claude A Piché, Robert M Fielding, Kathleen M Holland, S Dean Allison, Raghvendra K Dubey, Edwin K Jackson. 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol.
The Journal of pharmacology and experimental therapeutics.
2004 Jun; 309(3):1093-7. doi:
10.1124/jpet.103.062505. [PMID: 14872091] - Lefteris C Zacharia, Joseph A Gogos, Maria Karayiorgou, Edwin K Jackson, Delbert G Gillespie, Federica Barchiesi, Raghvendra K Dubey. Methoxyestradiols mediate the antimitogenic effects of 17beta-estradiol: direct evidence from catechol-O-methyltransferase-knockout mice.
Circulation.
2003 Dec; 108(24):2974-8. doi:
10.1161/01.cir.0000106900.66354.30. [PMID: 14662705] - Michael Teepker, Norman Anthes, Jürgen-Christian Krieg, Helmut Vedder. 2-OH-estradiol, an endogenous hormone with neuroprotective functions.
Journal of psychiatric research.
2003 Nov; 37(6):517-23. doi:
10.1016/s0022-3956(03)00068-2. [PMID: 14563383] - Raghvendra K Dubey, Lefteris C Zacharia, Delbert G Gillespie, Bruno Imthurn, Edwin K Jackson. Catecholamines block the antimitogenic effect of estradiol on human glomerular mesangial cells.
Hypertension (Dallas, Tex. : 1979).
2003 Sep; 42(3):349-55. doi:
10.1161/01.hyp.0000088320.81260.26. [PMID: 12913061] - Kaori Takanashi, Yasunori Osanai, Takahiro Kyo, Itsuo Yoshizawa. Comparison of ex vivo inhibitory effect between 2-hydroxyestradiol and its 17-sulfate on rat hepatic microsomal lipid peroxidation.
Lipids.
2003 Aug; 38(8):847-54. doi:
10.1007/s11745-003-1135-4. [PMID: 14577664] - Lefteris C Zacharia, Raghvendra K Dubey, Zaichuan Mi, Edwin K Jackson. Methylation of 2-hydroxyestradiol in isolated organs.
Hypertension (Dallas, Tex. : 1979).
2003 Jul; 42(1):82-7. doi:
10.1161/01.hyp.0000074702.06466.27. [PMID: 12771046] - Raghvendra K Dubey, Delbert G Gillespie, Lefteris C Zacharia, Federica Barchiesi, Bruno Imthurn, Edwin K Jackson. CYP450- and COMT-derived estradiol metabolites inhibit activity of human coronary artery SMCs.
Hypertension (Dallas, Tex. : 1979).
2003 Mar; 41(3 Pt 2):807-13. doi:
10.1161/01.hyp.0000048862.28501.72. [PMID: 12624000] - Stevan P Tofovic, Raghvendra Dubey, Eman M Salah, Edwin K Jackson. 2-Hydroxyestradiol attenuates renal disease in chronic puromycin aminonucleoside nephropathy.
Journal of the American Society of Nephrology : JASN.
2002 Nov; 13(11):2737-47. doi:
10.1097/01.asn.0000031804.77546.f5. [PMID: 12397044] - Sanae Muraoka, Toshiaki Miura. Protection by estrogens of biological damage by 2,2'-azobis(2-amidinopropane) dihydrochloride.
The Journal of steroid biochemistry and molecular biology.
2002 Nov; 82(4-5):343-8. doi:
10.1016/s0960-0760(02)00216-9. [PMID: 12589941] - S P Tofovic, R K Dubey, E K Jackson. 2-Hydroxyestradiol attenuates the development of obesity, the metabolic syndrome, and vascular and renal dysfunction in obese ZSF1 rats.
The Journal of pharmacology and experimental therapeutics.
2001 Dec; 299(3):973-7. doi:
. [PMID: 11714885] - R K Dubey, E K Jackson, P J Keller, B Imthurn, M Rosselli. Estradiol metabolites inhibit endothelin synthesis by an estrogen receptor-independent mechanism.
Hypertension (Dallas, Tex. : 1979).
2001 Feb; 37(2 Pt 2):640-4. doi:
10.1161/01.hyp.37.2.640. [PMID: 11230349] - S Xiao, D G Gillespie, C Baylis, E K Jackson, R K Dubey. Effects of estradiol and its metabolites on glomerular endothelial nitric oxide synthesis and mesangial cell growth.
Hypertension (Dallas, Tex. : 1979).
2001 Feb; 37(2 Pt 2):645-50. doi:
10.1161/01.hyp.37.2.645. [PMID: 11230350] - I Terashima, N Suzuki, S Shibutani. Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells.
Biochemistry.
2001 Jan; 40(1):166-72. doi:
10.1021/bi002273c. [PMID: 11141067] - A F Badawi, E L Cavalieri, E G Rogan. Effect of chlorinated hydrocarbons on expression of cytochrome P450 1A1, 1A2 and 1B1 and 2- and 4-hydroxylation of 17beta-estradiol in female Sprague-Dawley rats.
Carcinogenesis.
2000 Aug; 21(8):1593-9. doi:
10.1093/carcin/21.8.1593. [PMID: 10910964] - R R Newbold, J G Liehr. Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens.
Cancer research.
2000 Jan; 60(2):235-7. doi:
. [PMID: 10667565] - C E Garner, H B Matthews, L T Burka. Phenolphthalein metabolite inhibits catechol-O-methyltransferase-mediated metabolism of catechol estrogens: a possible mechanism for carcinogenicity.
Toxicology and applied pharmacology.
2000 Jan; 162(2):124-31. doi:
10.1006/taap.1999.8830. [PMID: 10637136] - A M Leal, M Begoña Ruiz-Larrea, R Martínez, M Lacort. Cytoprotective actions of estrogens against tert-butyl hydroperoxide-induced toxicity in hepatocytes.
Biochemical pharmacology.
1998 Dec; 56(11):1463-9. doi:
10.1016/s0006-2952(98)00248-2. [PMID: 9827578] - T Miura, S Muraoka, Y Fujimoto. Effect of estrogens on the oxidative damage induced by ferrylmyoglobin.
The Journal of steroid biochemistry and molecular biology.
1998 Oct; 67(1):57-62. doi:
10.1016/s0960-0760(98)00068-5. [PMID: 9780030] - Z Cheng, G R Rios, C D King, B L Coffman, M D Green, B Mojarrabi, P I Mackenzie, T R Tephly. Glucuronidation of catechol estrogens by expressed human UDP-glucuronosyltransferases (UGTs) 1A1, 1A3, and 2B7.
Toxicological sciences : an official journal of the Society of Toxicology.
1998 Sep; 45(1):52-7. doi:
10.1006/toxs.1998.2494. [PMID: 9848110] - K Yagi. Female hormones act as natural antioxidants--a survey of our research.
Acta biochimica Polonica.
1997; 44(4):701-9. doi:
10.18388/abp.1997_4372. [PMID: 9584850] - T Miura, S Muraoka, T Ogiso. Inhibition of lipid peroxidation by estradiol and 2-hydroxyestradiol.
Steroids.
1996 Jun; 61(6):379-83. doi:
10.1016/0039-128x(96)00044-x. [PMID: 8776801] - B T Zhu, J G Liehr. Inhibition of catechol O-methyltransferase-catalyzed O-methylation of 2- and 4-hydroxyestradiol by quercetin. Possible role in estradiol-induced tumorigenesis.
The Journal of biological chemistry.
1996 Jan; 271(3):1357-63. doi:
10.1074/jbc.271.3.1357. [PMID: 8576124] - B Ruiz-Larrea, A Leal, C Martín, R Martínez, M Lacort. Effects of estrogens on the redox chemistry of iron: a possible mechanism of the antioxidant action of estrogens.
Steroids.
1995 Nov; 60(11):780-3. doi:
10.1016/0039-128x(95)00119-b. [PMID: 8585103] - M B Ruiz-Larrea, A Leal, R Martínez, C Martín, M Lacort. Mechanism of inhibition of microsomal lipid peroxidation by estrogens: possible interactions with the cytochrome P450-dependent monooxygenase system.
Biochemical Society transactions.
1995 May; 23(2):256S. doi:
10.1042/bst023256s. [PMID: 7672280] - S Taniguchi, T Yanase, K Kobayashi, R Takayanagi, M Haji, F Umeda, H Nawata. Catechol estrogens are more potent antioxidants than estrogens for the Cu(2+)-catalyzed oxidation of low or high density lipoprotein: antioxidative effects of steroids on lipoproteins.
Endocrine journal.
1994 Dec; 41(6):605-11. doi:
10.1507/endocrj.41.605. [PMID: 7704084] - X Han, J G Liehr. 8-Hydroxylation of guanine bases in kidney and liver DNA of hamsters treated with estradiol: role of free radicals in estrogen-induced carcinogenesis.
Cancer research.
1994 Nov; 54(21):5515-7. doi:
NULL. [PMID: 7923187] - M B Ruiz-Larrea, A M Leal, M Liza, M Lacort, H de Groot. Antioxidant effects of estradiol and 2-hydroxyestradiol on iron-induced lipid peroxidation of rat liver microsomes.
Steroids.
1994 Jun; 59(6):383-8. doi:
10.1016/0039-128x(94)90006-x. [PMID: 7940617] - F R Tekpetey, D T Armstrong. Catecholestrogen modulation of steroid production by rat luteal cells: mechanism of action.
Molecular and cellular endocrinology.
1994 May; 101(1-2):49-57. doi:
10.1016/0303-7207(94)90218-6. [PMID: 9397936] - X Han, J G Liehr. DNA single-strand breaks in kidneys of Syrian hamsters treated with steroidal estrogens: hormone-induced free radical damage preceding renal malignancy.
Carcinogenesis.
1994 May; 15(5):997-1000. doi:
10.1093/carcin/15.5.997. [PMID: 8200107] - K Jankowski, D Kulawiak, M Woźniak. Inhibitory effect of 2-hydroxyestradiol on lipid peroxidation in placental microsomes.
Acta biochimica Polonica.
1994; 41(2):151-2. doi:
10.18388/abp.1994_4742. [PMID: 7976029] - B T Zhu, J G Liehr. Inhibition of the catechol-O-methyltransferase-catalyzed O-methylation of 2- and 4-hydroxyestradiol by catecholamine: implications for the mechanism of estrogen-induced carcinogenesis.
Archives of biochemistry and biophysics.
1993 Jul; 304(1):248-56. doi:
10.1006/abbi.1993.1346. [PMID: 8323288] - K Saegusa, E Suzuki, T Anjo, Y Matsuki, T Nambara. Determination of catechol and guaiacol estrogens in urine by capillary gas chromatography/mass spectrometry.
Biomedical chromatography : BMC.
1993 May; 7(3):172-6. doi:
10.1002/bmc.1130070315. [PMID: 8391354] - C F Rosenkrans, B C Paria, D L Davis, G Milliken. Synthesis of prostaglandins by pig blastocysts cultured in medium containing estradiol or catechol estrogen.
Prostaglandins.
1992 Apr; 43(4):309-19. doi:
10.1016/0090-6980(92)90031-n. [PMID: 1319081] - D Roy, J G Liehr. Target organ-specific inactivation of drug metabolizing enzymes in kidney of hamsters treated with estradiol.
Molecular and cellular biochemistry.
1992 Mar; 110(1):31-9. doi:
10.1007/bf02385003. [PMID: 1315925] - J C Seegers, C H van Aswegen, B L Nieuwoudt, W S Joubert. Morphological effects of the catecholestrogens on cells of the seminiferous tubules of Sprague-Dawley rats.
Andrologia.
1991 Sep; 23(5):339-45. doi:
10.1111/j.1439-0272.1991.tb02576.x. [PMID: 1666271] - F R Tekpetey, D T Armstrong. Steroidogenic response of rat and pig luteal cells to estradiol-17 beta and catecholestrogens in vitro.
Biology of reproduction.
1991 Sep; 45(3):498-505. doi:
10.1095/biolreprod45.3.498. [PMID: 1664248] - R W Brueggemeier, K Tseng, N E Katlic, M A Beleh, Y C Lin. Estrogen metabolism in primary kidney cell cultures from Syrian hamsters.
Journal of steroid biochemistry.
1990 Jul; 36(4):325-31. doi:
10.1016/0022-4731(90)90225-h. [PMID: 2391962] - J G Liehr, D Roy, A Ari-Ulubelen, Q D Bui, J Weisz, H W Strobel. Effect of chronic estrogen treatment of Syrian hamsters on microsomal enzymes mediating formation of catecholestrogens and their redox cycling: implications for carcinogenesis.
Journal of steroid biochemistry.
1990 Apr; 35(5):555-60. doi:
10.1016/0022-4731(90)90198-2. [PMID: 2162450] - D Roy, J Weisz, J G Liehr. The O-methylation of 4-hydroxyestradiol is inhibited by 2-hydroxyestradiol: implications for estrogen-induced carcinogenesis.
Carcinogenesis.
1990 Mar; 11(3):459-62. doi:
10.1093/carcin/11.3.459. [PMID: 2311190] - D Roy, Q D Bui, J Weisz, J G Liehr. Comparison of assays for catechol estrogen synthase activity: product isolation vs radioenzymatic catechol-O-methyltransferase-coupled procedures.
Journal of steroid biochemistry.
1989 Aug; 33(2):243-9. doi:
10.1016/0022-4731(89)90300-2. [PMID: 2549304] - J J Fernández-Ruiz, C Alvarez-Sanz, J A Ramos. 2-Hydroxyestradiol is not mediating the effects of estradiol on tuberoinfundibular dopaminergic neurons controlling prolactin secretion in female rats.
Journal of steroid biochemistry.
1989 Jan; 32(1A):71-5. doi:
10.1016/0022-4731(89)90016-2. [PMID: 2536446] - L J Spicer, J M Hammond. Mechanism of action of 2-hydroxyestradiol on steroidogenesis in ovarian granulosa cells: interactions with catecholamines and gonadotropins involve cyclic adenosine monophosphate.
Biology of reproduction.
1989 Jan; 40(1):87-95. doi:
10.1095/biolreprod40.1.87. [PMID: 2538165] - G Emons, G R Merriam, D Pfeiffer, D L Loriaux, P Ball, R Knuppen. Metabolism of exogenous 4- and 2-hydroxyestradiol in the human male.
Journal of steroid biochemistry.
1987 Nov; 28(5):499-504. doi:
10.1016/0022-4731(87)90508-5. [PMID: 2824929] - K E Hudson, E J Wickings, S G Hillier. Effects of 2-hydroxyoestradiol, oestradiol and testosterone on FSH-induction of catecholamine- and gonadotrophin-responsive progesterone biosynthesis in rat granulosa cell cultures.
Journal of steroid biochemistry.
1987 Sep; 28(3):267-72. doi:
10.1016/0022-4731(87)91017-x. [PMID: 2821323] - S W Lamberts, T Verleun. Differences in the mechanism of the inhibitory actions of catecholestrogens, tamoxifen and high concentrations of estrogens on prolactin release by cultured rat pituitary tumor cells.
European journal of cancer & clinical oncology.
1987 Aug; 23(8):1117-23. doi:
10.1016/0277-5379(87)90143-x. [PMID: 2820746] - L J Spicer, J M Hammond. Catecholestrogens stimulate progestin secretion by cultured porcine granulosa cells.
Molecular and cellular endocrinology.
1987 Mar; 50(1-2):139-47. doi:
10.1016/0303-7207(87)90086-4. [PMID: 3034696] - M Nakano, K Sugioka, I Naito, S Takekoshi, E Niki. Novel and potent biological antioxidants on membrane phospholipid peroxidation: 2-hydroxy estrone and 2-hydroxy estradiol.
Biochemical and biophysical research communications.
1987 Feb; 142(3):919-24. doi:
10.1016/0006-291x(87)91501-4. [PMID: 3827906] - N Parvizi. Differential effects of catecholoestradiol-17 beta and oestradiol-17 beta on concentrations of plasma LH in the fetal pig.
The Journal of endocrinology.
1986 Nov; 111(2):297-300. doi:
10.1677/joe.0.1110297. [PMID: 3794584] - Y Okatani. [Study on the central action of catecholestrogen: effect of 2-hydroxyestrogens on the preovulatory LH surge].
Nihon Sanka Fujinka Gakkai zasshi.
1986 Feb; 38(2):151-60. doi:
. [PMID: 3514773] - J G Liehr, W F Fang, D A Sirbasku, A Ari-Ulubelen. Carcinogenicity of catechol estrogens in Syrian hamsters.
Journal of steroid biochemistry.
1986 Jan; 24(1):353-6. doi:
10.1016/0022-4731(86)90080-4. [PMID: 3009986] - P Ball, G Emons. Effects of short-term exposure to catecholestrogens on serum concentrations of gonadotrophins and metabolism of catecholestrogens in ovariectomized rats.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.
1985 Apr; 17(4):184-8. doi:
10.1055/s-2007-1013487. [PMID: 2989139] - I Yoshizawa, M Kameyama. Specific antiserum to 2-hydroxyestradiol 17-sulfate (clinical analysis on steroids. XXX).
Chemical & pharmaceutical bulletin.
1985 Feb; 33(2):679-84. doi:
10.1248/cpb.33.679. [PMID: 4017113] - A K Brar, G Fink. Effects of acute administration of 2-hydroxylated metabolites of oestrogens on LH and prolactin secretion in male and female prepubertal rats.
The Journal of endocrinology.
1984 Dec; 103(3):317-25. doi:
10.1677/joe.0.1030317. [PMID: 6094697] - S Miyabo, S Kishida, T Sugiyama, T Hashimoto, Y Fujii, M Teranishi. Effects of 2-hydroxyoestradiol and 4-hydroxyoestradiol on gonadotrophin and prolactin secretion in women.
Acta endocrinologica.
1984 Jan; 105(1):1-5. doi:
10.1530/acta.0.1050001. [PMID: 6421038] - P Ball, G Emons, H Kayser, J Teichmann. Metabolic clearance rates of catechol estrogens in rats.
Endocrinology.
1983 Nov; 113(5):1781-3. doi:
10.1210/endo-113-5-1781. [PMID: 6628326] - N J MacLusky, M Riskalla, L Krey, N Parvizi, F Naftolin. Anovulation in female rats induced by neonatal administration of the catechol estrogens, 2-hydroxy-estradiol and 4-hydroxy-estradiol.
Neuroendocrinology.
1983 Nov; 37(5):321-7. doi:
10.1159/000123569. [PMID: 6196675] - G R Merriam, D G Pfeiffer, D L Loriaux, M B Lipsett. Catechol estrogens and the control of gonadotropin and prolactin secretion in man.
Journal of steroid biochemistry.
1983 Jul; 19(1B):619-25. doi:
10.1016/0022-4731(83)90227-3. [PMID: 6310245] - N Parvizi, F Ellendorff. Catecholestrogens in the brain: neuroendocrine integration.
Journal of steroid biochemistry.
1983 Jul; 19(1B):615-8. doi:
10.1016/0022-4731(83)90226-1. [PMID: 6310244] - S Kono, G R Merriam, D D Brandon, D L Loriaux, M B Lipsett, T Fujino. Radioimmunoassay and metabolic clearance rate of catecholestrogens, 2-hydroxyestrone and 2-hydroxyestradiol in man.
Journal of steroid biochemistry.
1983 Jul; 19(1B):627-33. doi:
10.1016/0022-4731(83)90228-5. [PMID: 6310246] - J Schneider, H L Bradlow, G Strain, J Levin, K Anderson, J Fishman. Effects of obesity on estradiol metabolism: decreased formation of nonuterotropic metabolites.
The Journal of clinical endocrinology and metabolism.
1983 May; 56(5):973-8. doi:
10.1210/jcem-56-5-973. [PMID: 6833471] - N Parvizi, W Wuttke. Catecholestrogens affect catecholamine turnover rates in the anterior part of the mediobasal hypothalamus and medial preoptic area in the male and female castrated rat.
Neuroendocrinology.
1983; 36(1):21-6. doi:
10.1159/000123523. [PMID: 6828204] - K Uchida, S Morimoto, I Yamamoto, T Kigoshi, S Miyabo, Y Fujii. Effect of the catecholestrogen 2-hydroxyestradiol on the renin-angiotensin system in the rat.
Endocrinologia japonica.
1982 Dec; 29(6):709-12. doi:
10.1507/endocrj1954.29.709. [PMID: 6763895] - I J Clarke, K Wynne, J W Funder, J K Findlay. Effects of 2-hydroxyoestradiol-17 beta on plasma luteinizing hormone, follicle-stimulating hormone and prolactin, and nuclear translocation of pituitary oestrogen receptors in ovariectomized ewes.
The Journal of endocrinology.
1982 Oct; 95(1):19-27. doi:
10.1677/joe.0.0950019. [PMID: 6290586] - S Kono. [Specific radioimmunoassay and physiological significance of unconjugated 2-hydroxyestrone and 2-hydroxyestradiol-17 beta in human blood (author's transl)].
Nihon Sanka Fujinka Gakkai zasshi.
1982 Jun; 34(6):794-800. doi:
. [PMID: 6284845] - J F Rodriguez-Sierra, C A Blake. Catecholestrogens and release of anterior pituitary gland hormones. II. Prolactin.
Endocrinology.
1982 Feb; 110(2):325-9. doi:
10.1210/endo-110-2-325. [PMID: 6276130] - J F Rodriguez-Sierra, C A Blake. Catecholestrogens and release of anterior pituitary gland hormones. I. Luteinizing hormone.
Endocrinology.
1982 Feb; 110(2):318-24. doi:
10.1210/endo-110-2-318. [PMID: 6276129] - S Kono, G R Merriam, D D Brandon, D L Loriaux, M B Lipsett. Radioimmunoassay and metabolism of the catechol estrogen 2-hydroxyestradiol.
The Journal of clinical endocrinology and metabolism.
1982 Jan; 54(1):150-4. doi:
10.1210/jcem-54-1-150. [PMID: 7054211] - S H Shin, L Bates, P H Jellinck. Temporal and other effects of catechol estrogens on prolactin secretion in the rat.
Neuroendocrinology.
1981 Dec; 33(6):352-7. doi:
10.1159/000123260. [PMID: 6275286] - S Franks, N J MacLusky, S J Naish, F Naftolin. Actions of catechol oestrogens on concentrations of serum luteinizing hormone in the adult castrated rat: various effects of 4-hydroxyoestradiol and 2-hydroxyoestradiol.
The Journal of endocrinology.
1981 May; 89(2):289-95. doi:
10.1677/joe.0.0890289. [PMID: 7241016] - H Kieczka, H Remmer. Influence of oxygen on the inhibition of liver microsomal activation of carbon tetrachloride by the catechol 2-hydroxyestradiol-17 beta.
Biochemical pharmacology.
1981 Feb; 30(4):319-24. doi:
10.1016/0006-2952(81)90061-7. [PMID: 7194046] - H Breuer, H T Schneider, C Doberauer, S Grüter, W Ladosky. Effects of oestradiol-17 beta and 2-hydroxy-oestradiol-17 beta on LH-concentration in plasma and COMT activities in hypothalamic nuclei of rats.
Experimental brain research.
1981; Suppl 3(?):118-29. doi:
10.1007/978-3-642-45525-4_9. [PMID: 7250242] - J M Schaeffer, S Stevens, R G Smith, A J Hsueh. Binding of 2-hydroxyestradiol to rat anterior pituitary cell membranes.
The Journal of biological chemistry.
1980 Oct; 255(20):9838-43. doi:
. [PMID: 7430105] - R L Barbieri, R B Todd, H Morishita, K J Ryan, J Fishman, F Naftolin. Response of serum prolactin to catechol estrogen in the immature rat.
Fertility and sterility.
1980 Oct; 34(4):391-3. doi:
NULL. [PMID: 6252068] - S Franks, P Ball, F Naftolin, K B Ruf. Effect of catechol oestrogens on induced ovulation in the immature rat.
The Journal of endocrinology.
1980 Aug; 86(2):263-8. doi:
10.1677/joe.0.0860263. [PMID: 6253586] - C P Martucci, J Fishman. Impact of continuously administered catechol estrogens on uterine growth and luteinizing hormone secretion.
Endocrinology.
1979 Dec; 105(6):1288-92. doi:
10.1210/endo-105-6-1288. [PMID: 499073] - L R AXELROD, P N RAO, J W GOLDZIEHER. The conversion of 2-hydroxyestradiol-17 beta to 2-hydroxy and 2-methoxy metabolites in human urine.
Archives of biochemistry and biophysics.
1961 Aug; 94(?):265-8. doi:
10.1016/0003-9861(61)90040-6. [PMID: 13685342]