16α-Hydroxyestrone (BioDeep_00001868314)
Main id: BioDeep_00000637483
代谢物信息卡片
16alpha-hydroxyestrone
化学式: C18H22O3 (286.15688620000003)
中文名称: 16α-羟基雌酮
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC12CCC3C(C1CC(C2=O)O)CCC4=C3C=CC(=C4)O
InChI: InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
描述信息
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
The 16alpha-hydroxy derivative of estrone; a minor estrogen metabolite.
同义名列表
2 个代谢物同义名
数据库引用编号
12 个数据库交叉引用编号
- ChEBI: CHEBI:776
- KEGG: C05300
- PubChem: 115116
- ChEMBL: CHEMBL1233720
- CAS: 566-76-7
- MetaboLights: MTBLC776
- PubChem: 7684
- LipidMAPS: LMST02010041
- PDB-CCD: J2Z
- 3DMET: B01840
- NIKKAJI: J130.683I
- RefMet: 16alpha-Hydroxyestrone
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)
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
- Xueying Ye, Tao Peng, Yuan Li, Tongwang Huang, Hui Wang, Zhong Hu. Identification of an important function of CYP123: Role in the monooxygenase activity in a novel estradiol degradation pathway in bacteria.
The Journal of steroid biochemistry and molecular biology.
2022 01; 215(?):106025. doi:
10.1016/j.jsbmb.2021.106025. [PMID: 34775032] - Frank Z Stanczyk. The 2-/16α-Hydroxylated Estrogen Ratio-Breast Cancer Risk Hypothesis: Insufficient Evidence for its Support.
The Journal of steroid biochemistry and molecular biology.
2020 07; 201(?):105685. doi:
10.1016/j.jsbmb.2020.105685. [PMID: 32320758] - Wahid Ali Khan, Mohd Wajid Ali Khan, Subuhi Sherwani, Waseem Ahmad Siddiqui. Depression enhanced the production of autoantibodies against 16α‑hydroxyestrone-estrogen receptor adduct in breast cancer.
International immunopharmacology.
2019 Jan; 66(?):251-259. doi:
10.1016/j.intimp.2018.11.018. [PMID: 30500622] - Vicky C Chang, Michelle Cotterchio, Beatrice A Boucher, David J A Jenkins, Lucia Mirea, Susan E McCann, Lilian U Thompson. Effect of Dietary Flaxseed Intake on Circulating Sex Hormone Levels among Postmenopausal Women: A Randomized Controlled Intervention Trial.
Nutrition and cancer.
2019; 71(3):385-398. doi:
10.1080/01635581.2018.1516789. [PMID: 30375890] - Cynthia A Thomson, H H Sherry Chow, Betsy C Wertheim, Denise J Roe, Alison Stopeck, Gertraud Maskarinec, Maria Altbach, Pavani Chalasani, Chuan Huang, Meghan B Strom, Jean-Philippe Galons, Patricia A Thompson. A randomized, placebo-controlled trial of diindolylmethane for breast cancer biomarker modulation in patients taking tamoxifen.
Breast cancer research and treatment.
2017 Aug; 165(1):97-107. doi:
10.1007/s10549-017-4292-7. [PMID: 28560655] - Regina G Ziegler, Barbara J Fuhrman, Steven C Moore, Charles E Matthews. Epidemiologic studies of estrogen metabolism and breast cancer.
Steroids.
2015 Jul; 99(Pt A):67-75. doi:
10.1016/j.steroids.2015.02.015. [PMID: 25725255] - Dina Nikitina, Marcia Llacuachaqui, Daniel Sepkovic, H Leon Bradlow, Steven A Narod, Joanne Kotsopoulos. The effect of oral 3,3'-diindolylmethane supplementation on the 2:16α-OHE ratio in BRCA1 mutation carriers.
Familial cancer.
2015 Jun; 14(2):281-6. doi:
10.1007/s10689-015-9783-2. [PMID: 25613194] - Anushka Dikshit, Manoel Adrião Gomes Filho, Erfan Eilati, Stacey McGee, Carrie Small, Chunqi Gao, Thomas Klug, Dale Buchanan Hales. Flaxseed reduces the pro-carcinogenic micro-environment in the ovaries of normal hens by altering the PG and oestrogen pathways in a dose-dependent manner.
The British journal of nutrition.
2015 May; 113(9):1384-95. doi:
10.1017/s000711451500029x. [PMID: 25850566] - Xiangyan Ruan, Harald Seeger, Diethelm Wallwiener, Jens Huober, Alfred O Mueck. The ratio of the estradiol metabolites 2-hydroxyestrone (2-OHE1) and 16α-hydroxyestrone (16-OHE1) may predict breast cancer risk in postmenopausal but not in premenopausal women: two case-control studies.
Archives of gynecology and obstetrics.
2015 May; 291(5):1141-6. doi:
10.1007/s00404-014-3512-1. [PMID: 25318606] - Paulina M Merino, Daniela Martínez, German Iñiguez, Patricia Lopez, Fernando Cassorla, Francisco Perez-Bravo, Ethel Codner. Elevation of C-reactive protein during the luteal phase in healthy adolescents.
Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology.
2015 Apr; 31(4):260-3. doi:
10.3109/09513590.2014.982086. [PMID: 25392126] - 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] - Estela Ytelina Godínez Martínez, René Santillán Ballesteros, Ana Elena Lemus Bravo, Reyna Sámano, Maricruz Tolentino Dolores, Ana Lilia Rodríguez Ventura, Ana Rosa Juárez González. [Determination of 2-hydroxyestrone /16α-hydroxyestrone ratio in urine of Mexican women as a risk indicator for breast cancer and its relationship with other risk factors].
Nutricion hospitalaria.
2014 Oct; 31(2):835-40. doi:
10.3305/nh.2015.31.2.8172. [PMID: 25617571] - Gertraud Maskarinec, Sreang Heak, Yukiko Morimoto, Laurie Custer, Adrian A Franke. The relation of urinary estrogen metabolites with mammographic densities in premenopausal women.
Cancer epidemiology.
2012 Oct; 36(5):e310-6. doi:
10.1016/j.canep.2012.03.014. [PMID: 22537763] - Charles E Matthews, Renee T Fortner, Xia Xu, Susan E Hankinson, A Heather Eliassen, Regina G Ziegler. Association between physical activity and urinary estrogens and estrogen metabolites in premenopausal women.
The Journal of clinical endocrinology and metabolism.
2012 Oct; 97(10):3724-33. doi:
10.1210/jc.2012-1732. [PMID: 22855335] - G Maskarinec, Y Morimoto, S Heak, M Isaki, A Steinbrecher, L Custer, A A Franke. Urinary estrogen metabolites in two soy trials with premenopausal women.
European journal of clinical nutrition.
2012 Sep; 66(9):1044-9. doi:
10.1038/ejcn.2012.71. [PMID: 22713773] - Jiang Huang, Jianghao Sun, Yanhua Chen, Yongmei Song, Lijia Dong, Qinmin Zhan, Ruiping Zhang, Zeper Abliz. Analysis of multiplex endogenous estrogen metabolites in human urine using ultra-fast liquid chromatography-tandem mass spectrometry: a case study for breast cancer.
Analytica chimica acta.
2012 Jan; 711(?):60-8. doi:
10.1016/j.aca.2011.10.058. [PMID: 22152797] - N T Telang, G Li, D W Sepkovic, H L Bradlow, G Y C Wong. Anti-proliferative effects of Chinese herb Cornus officinalis in a cell culture model for estrogen receptor-positive clinical breast cancer.
Molecular medicine reports.
2012 01; 5(1):22-8. doi:
10.3892/mmr.2011.617. [PMID: 21971582] - Yukiko Morimoto, Shannon M Conroy, Ian S Pagano, Marissa Isaki, Adrian A Franke, Frank J Nordt, Gertraud Maskarinec. Urinary estrogen metabolites during a randomized soy trial.
Nutrition and cancer.
2012; 64(2):307-14. doi:
10.1080/01635581.2012.648819. [PMID: 22293063] - Shawn Patel, Louise C Hawkley, John T Cacioppo, Christopher M Masi. Dietary fiber and serum 16α-hydroxyestrone, an estrogen metabolite associated with lower systolic blood pressure.
Nutrition (Burbank, Los Angeles County, Calif.).
2011 Jul; 27(7-8):778-81. doi:
10.1016/j.nut.2010.08.017. [PMID: 21035306] - Kannan Rangiah, Sumit J Shah, Anil Vachani, Eugene Ciccimaro, Ian A Blair. Liquid chromatography/mass spectrometry of pre-ionized Girard P derivatives for quantifying estrone and its metabolites in serum from postmenopausal women.
Rapid communications in mass spectrometry : RCM.
2011 May; 25(9):1297-307. doi:
10.1002/rcm.4982. [PMID: 21488127] - Shilpi Rajoria, Robert Suriano, Perminder Singh Parmar, Yushan Lisa Wilson, Uchechukwu Megwalu, Augustine Moscatello, H Leon Bradlow, Daniel W Sepkovic, Jan Geliebter, Stimson P Schantz, Raj K Tiwari. 3,3'-diindolylmethane modulates estrogen metabolism in patients with thyroid proliferative disease: a pilot study.
Thyroid : official journal of the American Thyroid Association.
2011 Mar; 21(3):299-304. doi:
10.1089/thy.2010.0245. [PMID: 21254914] - Nadia Obi, Alina Vrieling, Judith Heinz, Jenny Chang-Claude. Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer?.
International journal of women's health.
2011 Feb; 3(?):37-51. doi:
10.2147/ijwh.s7595. [PMID: 21339936] - Lulu Fu, Hong Xu. A preliminary study of the effectiveness of chinese therapeutic food on regulating female reproductive hormones.
Integrative medicine insights.
2011; 6(?):7-12. doi:
10.4137/imi.s5782. [PMID: 21614163] - Maggie Laidlaw, Carla A Cockerline, Daniel W Sepkovic. Effects of a breast-health herbal formula supplement on estrogen metabolism in pre- and post-menopausal women not taking hormonal contraceptives or supplements: a randomized controlled trial.
Breast cancer : basic and clinical research.
2010 Dec; 4(?):85-95. doi:
10.4137/bcbcr.s6505. [PMID: 21234288] - W Gao, C Zeng, D Cai, B Liu, Y Li, X Wen, Y Chen. Serum concentrations of selected endogenous estrogen and estrogen metabolites in pre- and post-menopausal Chinese women with osteoarthritis.
Journal of endocrinological investigation.
2010 Oct; 33(9):644-9. doi:
10.1007/bf03346664. [PMID: 20339312] - R G Ziegler, J M Faupel-Badger, L Y Sue, B J Fuhrman, R T Falk, J Boyd-Morin, M K Henderson, R N Hoover, T D Veenstra, L K Keefer, X Xu. A new approach to measuring estrogen exposure and metabolism in epidemiologic studies.
The Journal of steroid biochemistry and molecular biology.
2010 Aug; 121(3-5):538-45. doi:
10.1016/j.jsbmb.2010.03.068. [PMID: 20382222] - Susan R Sturgeon, Stella L Volpe, Elaine Puleo, Elizabeth R Bertone-Johnson, Joanna Heersink, Sara Sabelawski, Kristina Wahala, Carol Bigelow, Mindy S Kurzer. Effect of flaxseed consumption on urinary levels of estrogen metabolites in postmenopausal women.
Nutrition and cancer.
2010; 62(2):175-80. doi:
10.1080/01635580903305342. [PMID: 20099191] - Jessica M Faupel-Badger, Barbara J Fuhrman, Xia Xu, Roni T Falk, Larry K Keefer, Timothy D Veenstra, Robert N Hoover, Regina G Ziegler. Comparison of liquid chromatography-tandem mass spectrometry, RIA, and ELISA methods for measurement of urinary estrogens.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2010 Jan; 19(1):292-300. doi:
10.1158/1055-9965.epi-09-0643. [PMID: 20056650] - Christopher M Masi, Louise C Hawkley, Xia Xu, Timothy D Veenstra, John T Cacioppo. Serum estrogen metabolites and systolic blood pressure among middle-aged and older women and men.
American journal of hypertension.
2009 Nov; 22(11):1148-53. doi:
10.1038/ajh.2009.155. [PMID: 19713943] - Maddalena Barba, Li Yang, Holger J Schünemann, Francesca Sperati, Sara Grioni, Saverio Stranges, Kim C Westerlind, Giovanni Blandino, Michele Gallucci, Rossella Lauria, Luca Malorni, Paola Muti. Urinary estrogen metabolites and prostate cancer: a case-control study and meta-analysis.
Journal of experimental & clinical cancer research : CR.
2009 Oct; 28(?):135. doi:
10.1186/1756-9966-28-135. [PMID: 19814782] - Martin Schmidt, Regina Hartung, Silvia Capellino, Maurizio Cutolo, Antje Pfeifer-Leeg, Rainer H Straub. Estrone/17beta-estradiol conversion to, and tumor necrosis factor inhibition by, estrogen metabolites in synovial cells of patients with rheumatoid arthritis and patients with osteoarthritis.
Arthritis and rheumatism.
2009 Oct; 60(10):2913-22. doi:
10.1002/art.24859. [PMID: 19790073] - Annie Im, Victor G Vogel, Gretchen Ahrendt, Stacy Lloyd, Camille Ragin, Seymour Garte, Emanuela Taioli. Urinary estrogen metabolites in women at high risk for breast cancer.
Carcinogenesis.
2009 Sep; 30(9):1532-5. doi:
10.1093/carcin/bgp139. [PMID: 19502596] - Alan A Arslan, Roy E Shore, Yelena Afanasyeva, Karen L Koenig, Paolo Toniolo, Anne Zeleniuch-Jacquotte. Circulating estrogen metabolites and risk for breast cancer in premenopausal women.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2009 Aug; 18(8):2273-9. doi:
10.1158/1055-9965.epi-09-0312. [PMID: 19661086] - Go Li, Daniel W Sepkovic, H Leon Bradlow, Nitin T Telang, George Y C Wong. Lycium barbarum inhibits growth of estrogen receptor positive human breast cancer cells by favorably altering estradiol metabolism.
Nutrition and cancer.
2009; 61(3):408-14. doi:
10.1080/01635580802585952. [PMID: 19373615] - 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] - Mylène Aubertin-Leheudre, Sherwood Gorbach, Margo Woods, Johanna T Dwyer, Barry Goldin, Herman Adlercreutz. Fat/fiber intakes and sex hormones in healthy premenopausal women in USA.
The Journal of steroid biochemistry and molecular biology.
2008 Nov; 112(1-3):32-9. doi:
10.1016/j.jsbmb.2008.08.002. [PMID: 18761407] - MaryFran R Sowers, John Randolph, Mary Jannausch, Bill Lasley, Elizabeth Jackson, Daniel McConnell. Levels of sex steroid and cardiovascular disease measures in premenopausal and hormone-treated women at midlife: implications for the "timing hypothesis".
Archives of internal medicine.
2008 Oct; 168(19):2146-53. doi:
10.1001/archinte.168.19.2146. [PMID: 18955645] - Latanya M Scott, Xia Xu, Timothy D Veenstra, Janet A Tooze, Charles E Wood, Thomas C Register, Nancy D Kock, J Mark Cline. Past oral contraceptive use and current dietary soy isoflavones influence estrogen metabolism in postmenopausal monkeys (Macaca fascicularis).
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2008 Oct; 17(10):2594-602. doi:
10.1158/1055-9965.epi-08-0278. [PMID: 18843000] - A Heather Eliassen, Stacey A Missmer, Shelley S Tworoger, Susan E Hankinson. Circulating 2-hydroxy- and 16alpha-hydroxy estrone levels and risk of breast cancer among postmenopausal women.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2008 Aug; 17(8):2029-35. doi:
10.1158/1055-9965.epi-08-0262. [PMID: 18708395] - MaryFran Sowers, Daniel McConnell, Mary L Jannausch, John F Randolph, Robert Brook, Ellen B Gold, Sybil Crawford, Bill Lasley. Oestrogen metabolites in relation to isoprostanes as a measure of oxidative stress.
Clinical endocrinology.
2008 May; 68(5):806-13. doi:
10.1111/j.1365-2265.2007.03108.x. [PMID: 17980014] - Su-Ui Lee, Myung chull Rhee, Yong Ki Min, Seong Hwan Kim. Involvement of peroxiredoxin IV in the 16alpha-hydroxyestrone-induced proliferation of human MCF-7 breast cancer cells.
Cell biology international.
2008 Apr; 32(4):401-5. doi:
10.1016/j.cellbi.2007.12.009. [PMID: 18272409] - Sarah M Mense, Tom K Hei, Ramesh K Ganju, Hari K Bhat. Phytoestrogens and breast cancer prevention: possible mechanisms of action.
Environmental health perspectives.
2008 Apr; 116(4):426-33. doi:
10.1289/ehp.10538. [PMID: 18414622] - Kathryn H Schmitz, Meghan Warren, Andrew G Rundle, Nancy I Williams, Myron D Gross, Mindy S Kurzer. Exercise effect on oxidative stress is independent of change in estrogen metabolism.
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):220-3. doi:
10.1158/1055-9965.epi-07-0058. [PMID: 18199727] - Christophe Stavrakakis, Ronan Colin, Valérie Héquet, Catherine Faur, Pierre Le Cloirec. Development and statistical validation of a quantitative method for the determination of steroid hormones in environmental water by column liquid chromatography/tandem mass spectrometry.
Journal of AOAC International.
2008 Jan; 91(1):237-46. doi:
10.1093/jaoac/91.1.237. [PMID: 18376603] - Heather Greenlee, Charlotte Atkinson, Frank Z Stanczyk, Johanna W Lampe. A pilot and feasibility study on the effects of naturopathic botanical and dietary interventions on sex steroid hormone metabolism in premenopausal women.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2007 Aug; 16(8):1601-9. doi:
10.1158/1055-9965.epi-06-0938. [PMID: 17684134] - I P Hsu, H J Jou, C W Huang, T A Wang, W H Wu. The effects of soygerm extracts on blood lipoproteins, antioxidative capacity and urinary estrogen metabolites in postmenopausal women on hormone therapy.
International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics.
2007 Jul; 98(1):29-33. doi:
10.1016/j.ijgo.2007.03.031. [PMID: 17467711] - Leonard A Cohen, Jeffrey S Crespin, Carla Wolper, Edith A Zang, Brian Pittman, Zhonglin Zhao, Peter R Holt. Soy isoflavone intake and estrogen excretion patterns in young women: effect of probiotic administration.
In vivo (Athens, Greece).
2007 May; 21(3):507-12. doi:
. [PMID: 17591361] - Charles E Wood, Thomas C Register, J Mark Cline. Soy isoflavonoid effects on endogenous estrogen metabolism in postmenopausal female monkeys.
Carcinogenesis.
2007 Apr; 28(4):801-8. doi:
10.1093/carcin/bgl163. [PMID: 17032659] - Kristin L Campbell, Kim C Westerlind, Vicki J Harber, Gordon J Bell, John R Mackey, Kerry S Courneya. Effects of aerobic exercise training on estrogen metabolism in premenopausal women: a randomized controlled trial.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2007 Apr; 16(4):731-9. doi:
10.1158/1055-9965.epi-06-0784. [PMID: 17416764] - 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] - Susan E McCann, Jean Wactawski-Wende, Kari Kufel, James Olson, Bladimir Ovando, Susan Nowell Kadlubar, Warren Davis, Lisa Carter, Paola Muti, Peter G Shields, Jo L Freudenheim. Changes in 2-hydroxyestrone and 16alpha-hydroxyestrone metabolism with flaxseed consumption: modification by COMT and CYP1B1 genotype.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2007 Feb; 16(2):256-62. doi:
10.1158/1055-9965.epi-06-0633. [PMID: 17301257] - T H Lippert, H Adlercreutz, M R Berger, H Seeger, A O Mueck. Urinary phytoestrogen excretion of rats bearing methylnitrosourea-induced mammary carcinoma in response to treatment with 2-methoxyestradiol.
The Journal of steroid biochemistry and molecular biology.
2007 Feb; 103(2):158-62. doi:
10.1016/j.jsbmb.2006.08.005. [PMID: 17081745] - T L Klug, E Bågeman, C Ingvar, C Rose, H Jernström. Moderate coffee and alcohol consumption improves the estrogen metabolite profile in adjuvant treated breast cancer patients: a pilot study comparing pre- and post-operative levels.
Molecular genetics and metabolism.
2006 Dec; 89(4):381-9. doi:
10.1016/j.ymgme.2006.08.005. [PMID: 16978896] - Maurizio Cutolo, Silvia Capellino, Alberto Sulli, Bruno Serioli, Maria Elena Secchi, Barbara Villaggio, Rainer H Straub. Estrogens and autoimmune diseases.
Annals of the New York Academy of Sciences.
2006 Nov; 1089(?):538-47. doi:
10.1196/annals.1386.043. [PMID: 17261796] - MaryFran R Sowers, Angela L Wilson, Sharon R Kardia, Jian Chu, Daniel S McConnell. CYP1A1 and CYP1B1 polymorphisms and their association with estradiol and estrogen metabolites in women who are premenopausal and perimenopausal.
The American journal of medicine.
2006 Sep; 119(9 Suppl 1):S44-51. doi:
10.1016/j.amjmed.2006.07.006. [PMID: 16949388] - MaryFran R Sowers, Daniel McConnell, Mary Jannausch, Ayse G Buyuktur, Marc Hochberg, David A Jamadar. Estradiol and its metabolites and their association with knee osteoarthritis.
Arthritis and rheumatism.
2006 Aug; 54(8):2481-7. doi:
10.1002/art.22005. [PMID: 16871545] - Edwin K Chan, Daniel W Sepkovic, Helen J Yoo Bowne, Guo Pei Yu, Stimson P Schantz. A hormonal association between estrogen metabolism and proliferative thyroid disease.
Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery.
2006 Jun; 134(6):893-900. doi:
10.1016/j.otohns.2006.01.020. [PMID: 16730526] - MaryFran R Sowers, Sybil Crawford, Daniel S McConnell, John F Randolph, Ellen B Gold, Margaret K Wilkin, Bill Lasley. Selected diet and lifestyle factors are associated with estrogen metabolites in a multiracial/ethnic population of women.
The Journal of nutrition.
2006 Jun; 136(6):1588-95. doi:
10.1093/jn/136.6.1588. [PMID: 16702326] - R Naik, S Nixon, A Lopes, K Godfrey, M H Hatem, J M Monaghan. A randomized phase II trial of indole-3-carbinol in the treatment of vulvar intraepithelial neoplasia.
International journal of gynecological cancer : official journal of the International Gynecological Cancer Society.
2006 Mar; 16(2):786-90. doi:
10.1111/j.1525-1438.2006.00386.x. [PMID: 16681761] - W H Wu, S C Lu, T F Wang, H J Jou, T A Wang. Effects of docosahexaenoic acid supplementation on blood lipids, estrogen metabolism, and in vivo oxidative stress in postmenopausal vegetarian women.
European journal of clinical nutrition.
2006 Mar; 60(3):386-92. doi:
10.1038/sj.ejcn.1602328. [PMID: 16278686] - 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] - H Leon Bradlow, Helena Jernström, Daniel W Sepkovic, Thomas L Klug, Steven A Narod. Comparison of plasma and urinary levels of 2-hydroxyestrogen and 16 alpha-hydroxyestrogen metabolites.
Molecular genetics and metabolism.
2006 Feb; 87(2):135-46. doi:
10.1016/j.ymgme.2005.08.001. [PMID: 16165383] - Geoffrey C Kabat, Erin S O'Leary, Marilie D Gammon, Daniel W Sepkovic, Susan L Teitelbaum, Julie A Britton, Mary B Terry, Alfred I Neugut, H Leon Bradlow. Estrogen metabolism and breast cancer.
Epidemiology (Cambridge, Mass.).
2006 Jan; 17(1):80-8. doi:
10.1097/01.ede.0000190543.40801.75. [PMID: 16357599] - Anja Wellejus, Anja Olsen, Anne Tjonneland, Birthe L Thomsen, Kim Overvad, Steffen Loft. Urinary hydroxyestrogens and breast cancer risk among postmenopausal women: a prospective study.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2005 Sep; 14(9):2137-42. doi:
10.1158/1055-9965.epi-04-0934. [PMID: 16172222] - Wen-Huey Wu, Li-Yun Liu, Cheng-Jih Chung, Hei-Jen Jou, Tzong-An Wang. Estrogenic effect of yam ingestion in healthy postmenopausal women.
Journal of the American College of Nutrition.
2005 Aug; 24(4):235-43. doi:
10.1080/07315724.2005.10719470. [PMID: 16093400] - Ann T Bentz, Carole M Schneider, Kim C Westerlind. The relationship between physical activity and 2-hydroxyestrone, 16alpha-hydroxyestrone, and the 2/16 ratio in premenopausal women (United States).
Cancer causes & control : CCC.
2005 May; 16(4):455-61. doi:
10.1007/s10552-004-6256-6. [PMID: 15953988] - Stefanie Weber, Prisca Leuschner, Peter Kämpfer, Wolfgang Dott, Juliane Hollender. Degradation of estradiol and ethinyl estradiol by activated sludge and by a defined mixed culture.
Applied microbiology and biotechnology.
2005 Apr; 67(1):106-12. doi:
10.1007/s00253-004-1693-4. [PMID: 15290133] - Jane Teas, Joan E Cunningham, Jay H Fowke, Daniela Nitcheva, C P Kanwat, R J Boulware, Daniel W Sepkovic, Thomas G Hurley, James R Hebert. Urinary estrogen metabolites, prostate specific antigen, and body mass index among African-American men in South Carolina.
Cancer detection and prevention.
2005; 29(6):494-500. doi:
10.1016/j.cdp.2005.08.004. [PMID: 16289388] - Valentina Paracchini, Paola Pedotti, Sara Raimondi, Seymour Garte, H Leon Bradlow, Daniel W Sepkovic, Emanuela Taioli. A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio.
Clinical chemistry and laboratory medicine.
2005; 43(7):702-6. doi:
10.1515/cclm.2005.119. [PMID: 16207128] - Reina C Armamento-Villareal, Nicola Napoli, Thomas Klug, Roberto Civitelli. The oxidative metabolism of estrogen modulates response to ERT/HRT in postmenopausal women.
Bone.
2004 Sep; 35(3):682-8. doi:
10.1016/j.bone.2004.05.010. [PMID: 15336604] - Charles E Matthews, Jay H Fowke, Qi Dai, H Leon Bradlow, Fan Jin, Xiao-Ou Shu, Yu-Tang Gao, Christopher Longcope, James R Hebert, Wei Zheng. Physical activity, body size, and estrogen metabolism in women.
Cancer causes & control : CCC.
2004 Jun; 15(5):473-81. doi:
10.1023/b:caco.0000036445.04238.87. [PMID: 15286467] - Amr S Soliman, Suryanarayana V Vulimiri, Heather E Kleiner, Jianjun Shen, Saad Eissa, Magda Morad, Hala Taha, Farzana Lukmanji, Donghui Li, Dennis A Johnston, Herng-Hsang Lo, Serrine Lau, John Digiovanni, Melissa L Bondy. High levels of oxidative DNA damage in lymphocyte DNA of premenopausal breast cancer patients from Egypt.
International journal of environmental health research.
2004 Apr; 14(2):121-34. doi:
10.1080/0960312042000209534. [PMID: 15203457] - A O Mueck, H Seeger, D Wallwiener. Endogenous estradiol metabolism during treatment with oral contraceptives.
International journal of clinical pharmacology and therapeutics.
2004 Mar; 42(3):160-4. doi:
10.5414/cpp42160. [PMID: 15049436] - M Cutolo, A Sulli, S Capellino, B Villaggio, P Montagna, B Seriolo, R H Straub. Sex hormones influence on the immune system: basic and clinical aspects in autoimmunity.
Lupus.
2004; 13(9):635-8. doi:
10.1191/0961203304lu1094oa. [PMID: 15485092] - Shelley S Tworoger, Jessica Chubak, Erin J Aiello, Cornelia M Ulrich, Charlotte Atkinson, John D Potter, Yutaka Yasui, Patricia L Stapleton, Johanna W Lampe, Federico M Farin, Frank Z Stanczyk, Anne McTiernan. Association of CYP17, CYP19, CYP1B1, and COMT polymorphisms with serum and urinary sex hormone concentrations in postmenopausal women.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2004 Jan; 13(1):94-101. doi:
10.1158/1055-9965.epi-03-0026. [PMID: 14744739] - Kathie M Dalessandri, Gary L Firestone, Mark D Fitch, H Leon Bradlow, Leonard F Bjeldanes. Pilot study: effect of 3,3'-diindolylmethane supplements on urinary hormone metabolites in postmenopausal women with a history of early-stage breast cancer.
Nutrition and cancer.
2004; 50(2):161-7. doi:
10.1207/s15327914nc5002_5. [PMID: 15623462] - A O Mueck, H Seeger, T H Lippert. [Estrogen-dependent neoplasia - what is the significance of estradiol metabolites].
Zentralblatt fur Gynakologie.
2003 Nov; 125(11):458-66. doi:
10.1055/s-2003-44575. [PMID: 14634875] - Jane A Cauley, Joseph M Zmuda, Michelle E Danielson, Britt-Marie Ljung, Douglas C Bauer, Steven R Cummings, Lewis H Kuller. Estrogen metabolites and the risk of breast cancer in older women.
Epidemiology (Cambridge, Mass.).
2003 Nov; 14(6):740-4. doi:
10.1097/01.ede.0000091607.77374.74. [PMID: 14569192] - Charlotte Atkinson, Heather E Skor, E Dawn Fitzgibbons, Delia Scholes, Chu Chen, Kristiina Wähälä, Stephen M Schwartz, Johanna W Lampe. Urinary equol excretion in relation to 2-hydroxyestrone and 16alpha-hydroxyestrone concentrations: an observational study of young to middle-aged women.
The Journal of steroid biochemistry and molecular biology.
2003 Jul; 86(1):71-7. doi:
10.1016/s0960-0760(03)00259-0. [PMID: 12943746] - R B Alvarez-Vasquez, D Axelrod, K Frenkel, M C Newman, D W Sepkovic, H L Bradlow, B Zumoff. Influence of postmenopausal hormone replacement therapy on an estrogen metabolite biomarker of risk for breast cancer.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.
2003 Jun; 35(6):358-61. doi:
10.1055/s-2003-41357. [PMID: 12920658] - H Jernström, T L Klug, D W Sepkovic, H L Bradlow, S A Narod. Predictors of the plasma ratio of 2-hydroxyestrone to 16alpha-hydroxyestrone among pre-menopausal, nulliparous women from four ethnic groups.
Carcinogenesis.
2003 May; 24(5):991-1005. doi:
10.1093/carcin/bgg047. [PMID: 12771045] - Diane S Thompson, Margaret A Kirshner, Thomas L Klug, Kari B Kastango, Bruce G Pollock. A preliminary study of the effect of fluoxetine treatment on the 2:16-alpha-hydroxyestrone ratio in young women.
Therapeutic drug monitoring.
2003 Feb; 25(1):125-8. doi:
10.1097/00007691-200302000-00021. [PMID: 12548158] - Seon Hwa Lee, Kyung Mee Kim, Byung Hwa Jung, Woung Youn Chung, Cheong Soo Park, Bong Chul Chung. Estrogens in female thyroid cancer: alteration of urinary profiles in pre- and post-operative cases.
Cancer letters.
2003 Jan; 189(1):27-32. doi:
10.1016/s0304-3835(02)00514-1. [PMID: 12445674] - Jay H Fowke, Dai Qi, H Leon Bradlow, Xiao Ou Shu, Yu Tang Gao, Jin Rong Cheng, Fan Jin, Wei Zheng. Urinary estrogen metabolites and breast cancer: differential pattern of risk found with pre- versus post-treatment collection.
Steroids.
2003 Jan; 68(1):65-72. doi:
10.1016/s0039-128x(02)00116-2. [PMID: 12475724] - Paola Muti, Kim Westerlind, Tiejian Wu, Thomas Grimaldi, John De Berry, Holger Schünemann, Jo L Freudenheim, Helyn Hill, Giuseppe Carruba, Leon Bradlow. Urinary estrogen metabolites and prostate cancer: a case-control study in the United States.
Cancer causes & control : CCC.
2002 Dec; 13(10):947-55. doi:
10.1023/a:1021986811425. [PMID: 12588091] - Sidika E Kasim-Karakas, Rogelio U Almario, Laura Gregory, Heather Todd, Rodney Wong, Bill L Lasley. Effects of prune consumption on the ratio of 2-hydroxyestrone to 16alpha-hydroxyestrone.
The American journal of clinical nutrition.
2002 Dec; 76(6):1422-7. doi:
10.1093/ajcn/76.6.1422. [PMID: 12450912] - Richard S Lord, Bradley Bongiovanni, J Alexander Bralley. Estrogen metabolism and the diet-cancer connection: rationale for assessing the ratio of urinary hydroxylated estrogen metabolites.
Alternative medicine review : a journal of clinical therapeutic.
2002 Apr; 7(2):112-29. doi:
. [PMID: 11991791] - Giske Ursin, Stephanie London, Dongyun Yang, Chiu-Chen Tseng, Malcolm C Pike, Leslie Bernstein, Frank Z Stanczyk, Elisabet Gentzschein. Urinary 2-hydroxyestrone/16alpha-hydroxyestrone ratio and family history of breast cancer in premenopausal women.
Breast cancer research and treatment.
2002 Mar; 72(2):139-43. doi:
10.1023/a:1014896417653. [PMID: 12038704] - A O Mueck, H Seeger, T Gräser, M Oettel, T H Lippert. The effects of postmenopausal hormone replacement therapy and oral contraceptives on the endogenous estradiol metabolism.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.
2001 Dec; 33(12):744-7. doi:
10.1055/s-2001-19139. [PMID: 11753761] - S Lotinun, K C Westerlind, R T Turner. Tissue-selective effects of continuous release of 2-hydroxyestrone and 16alpha-hydroxyestrone on bone, uterus and mammary gland in ovariectomized growing rats.
The Journal of endocrinology.
2001 Jul; 170(1):165-74. doi:
10.1677/joe.0.1700165. [PMID: 11431149] - E Riza, I dos Santos Silva, B De Stavola, H L Bradlow, D W Sepkovic, D Linos, A Linos. Urinary estrogen metabolites and mammographic parenchymal patterns in postmenopausal women.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2001 Jun; 10(6):627-34. doi:
NULL. [PMID: 11401912] - H Jernström, D Vesprini, H L Bradlow, S A Narod. Re: CYP17 promoter polymorphism and breast cancer in Australian women under age forty years.
Journal of the National Cancer Institute.
2001 Apr; 93(7):554-5. doi:
10.1093/jnci/93.7.554. [PMID: 11287451] - W Zheng, F Jin, L A Dunning, X O Shu, Q Dai, W Q Wen, Y T Gao, J L Holtzman. Epidemiological study of urinary 6beta-hydroxycortisol to cortisol ratios and breast cancer risk.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2001 Mar; 10(3):237-42. doi:
NULL. [PMID: 11303593] - F W Spierto, F Gardner, S J Smith. Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults.
Steroids.
2001 Jan; 66(1):59-62. doi:
10.1016/s0039-128x(00)00139-2. [PMID: 11090660] - M C Bell, P Crowley-Nowick, H L Bradlow, D W Sepkovic, D Schmidt-Grimminger, P Howell, E J Mayeaux, A Tucker, E A Turbat-Herrera, J M Mathis. Placebo-controlled trial of indole-3-carbinol in the treatment of CIN.
Gynecologic oncology.
2000 Aug; 78(2):123-9. doi:
10.1006/gyno.2000.5847. [PMID: 10926790] - J H Fowke, C Longcope, J R Hebert. Brassica vegetable consumption shifts estrogen metabolism in healthy postmenopausal women.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2000 Aug; 9(8):773-9. doi:
NULL. [PMID: 10952093] - L J Lu, M Cree, S Josyula, M Nagamani, J J Grady, K E Anderson. Increased urinary excretion of 2-hydroxyestrone but not 16alpha-hydroxyestrone in premenopausal women during a soya diet containing isoflavones.
Cancer research.
2000 Mar; 60(5):1299-305. doi:
. [PMID: 10728690] - R T Falk, S C Rossi, T R Fears, D W Sepkovic, A Migella, H Adlercreutz, J Donaldson, H L Bradlow, R G Ziegler. A new ELISA kit for measuring urinary 2-hydroxyestrone, 16alpha-hydroxyestrone, and their ratio: reproducibility, validity, and assay performance after freeze-thaw cycling and preservation by boric acid.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2000 Jan; 9(1):81-7. doi:
NULL. [PMID: 10667467] - T Kishida, M Beppu, K Nashiki, T Izumi, K Ebihara. Effect of dietary soy isoflavone aglycones on the urinary 16alpha-to-2-hydroxyestrone ratio in C3H/HeJ mice.
Nutrition and cancer.
2000; 38(2):209-14. doi:
10.1207/s15327914nc382_10. [PMID: 11525599]