2-Hydroxyestrone (BioDeep_00000005782)
Main id: BioDeep_00000637483
human metabolite Endogenous blood metabolite natural product
代谢物信息卡片
(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
化学式: C18H22O3 (286.1569)
中文名称: 2-羟基雌酮
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC12CCC3C(C1CCC2=O)CCC4=CC(=C(C=C34)O)O
InChI: InChI=1S/C18H22O3/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/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1
描述信息
2-Hydroxyestrone (2-OHE1), also known as estra-1,3,5(10)-trien-2,3-diol-17-one, is an endogenous, naturally occurring catechol estrogen and a major metabolite of estrone and estradiol. 2-Hydroxyestrone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 2-Hydroxyestrone is considered to be a steroid molecule. It is formed irreversibly from estrone in the liver and to a lesser extent in other tissues via 2-hydroxylation mediated by cytochrome P450 enzymes, mainly the CYP3A and CYP1A subfamilies. 2-OHE1 is the most abundant catechol estrogen in the body. 2-Hydroxyestrone is found in all vertebrates. Vertebrates, especially mammals, metabolizes estrogen into two major pathways and one minor. The two major pathways lead to 2-hydroxyestrone and 16a-hydroxyestrone (2-OHE1 and 16a OHE1, respectively). The minor pathway leads to 4-hydroxyestrone (4-OHE1). 2a-hydroxyestrone is considered to be the good steroid metabolite (PMID: 8943806) as 2-hydroxyestrone does not stimulate cell growth and it blocks the action of stronger estrogens that may be carcinogenic. 2-hydroxyestrone is not significantly uterotrophic, whereas other hydroxylated estrogen metabolites including 2-hydroxyestradiol, 16a-hydroxyestrone, estriol, 4-hydroxyestradiol, and 4-hydroxyestrone all are. A low urinary ratio of 2-hydroxyestrone to 16-alpha-hydroxyestrone is a strong predictor of breast cancer risk among women (PMID: 19502596).
Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecular formula is C18H22O2. estrone has a melting point of 254.5 degrees Celsius. estrone is one of the three estrogens, which also include estriol and estradiol. estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. estrone sulfate is relevant to health and disease due to its conversion to estrone sulfate, a long-lived derivative of estrone. estrone sulfate acts as a pool of estrone which can be converted as needed to the more active estradiol. [HMDB]
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
D020011 - Protective Agents > D016588 - Anticarcinogenic Agents
D000970 - Antineoplastic Agents
同义名列表
9 个代谢物同义名
(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one; (1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one; Estra-1,3,5(10)-trien-17-one, 2,3-dihydroxy-; 2,3-Dihydroxyestra-1,3,5(10)-trien-17-one; 2-Hydroxyestrone, 4-(14)C-labeled; 2-hydroxyestrone; Catecholestrone; 2-OHE1; 2-Hydroxyestrone
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:1156
- KEGG: C05298
- PubChem: 440623
- PubChem: 9685
- HMDB: HMDB0000343
- Metlin: METLIN2579
- ChEMBL: CHEMBL1627343
- Wikipedia: 2-Hydroxyestrone
- foodb: FDB021966
- CAS: 362-06-1
- PMhub: MS000018652
- PubChem: 7682
- LipidMAPS: LMST02010032
- 3DMET: B01838
- NIKKAJI: J108.087C
- RefMet: 2-Hydroxyestrone
- KNApSAcK: 1156
- LOTUS: LTS0138930
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
8 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(2)
- Estrogen metabolism:
2-Methoxyestrone ⟶ 2-Methoxyestrone 3-glucuronide - Estrogen metabolism:
2-Methoxyestradiol ⟶ 2-methoxy-17beta-estradiol 3-glucuronide
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(6)
- Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine - Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine - Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine - Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine - Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine - Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine
PharmGKB(0)
10 个相关的物种来源信息
- 7711 - Chordata: LTS0138930
- 2759 - Eukaryota: LTS0138930
- 9604 - Hominidae: LTS0138930
- 9605 - Homo: LTS0138930
- 9606 - Homo sapiens:
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1038/NBT.2488
- 9606 - Homo sapiens: LTS0138930
- 40674 - Mammalia: LTS0138930
- 33208 - Metazoa: LTS0138930
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
- Xiaoli Zhang, Na Yang, Min Wang, JiaJia Ge, Huaijun Zhu, Jun He, Weihong Ge. Establishment and validation of a sensitive LC-MS/MS method for quantification of urinary estrogens in women with gestational diabetes mellitus.
Journal of pharmaceutical and biomedical analysis.
2022 Nov; 221(?):115044. doi:
10.1016/j.jpba.2022.115044. [PMID: 36126614] - 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] - 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] - 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] - Hannah Oh, Zeina G Khodr, Mark E Sherman, Maya Palakal, Ruth M Pfeiffer, Laura Linville, Berta M Geller, Pamela M Vacek, Donald L Weaver, Rachael E Chicoine, Roni T Falk, Hisani N Horne, Daphne Papathomas, Deesha A Patel, Jackie Xiang, Xia Xu, Timothy Veenstra, Stephen M Hewitt, John A Shepherd, Louise A Brinton, Jonine D Figueroa, Gretchen L Gierach. Relation of Serum Estrogen Metabolites with Terminal Duct Lobular Unit Involution Among Women Undergoing Diagnostic Image-Guided Breast Biopsy.
Hormones & cancer.
2016 12; 7(5-6):305-315. doi:
10.1007/s12672-016-0265-2. [PMID: 27138982] - 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] - Alan A Arslan, Karen L Koenig, Per Lenner, Yelena Afanasyeva, Roy E Shore, Yu Chen, Eva Lundin, Paolo Toniolo, Göran Hallmans, Anne Zeleniuch-Jacquotte. Circulating estrogen metabolites and risk of breast cancer in postmenopausal women.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2014 Jul; 23(7):1290-7. doi:
10.1158/1055-9965.epi-14-0009. [PMID: 24769889] - Nitin Telang, Gou Li, Daniel Sepkovic, H Leon Bradlow, George Y C Wong. Comparative efficacy of extracts from Lycium barbarum bark and fruit on estrogen receptor positive human mammary carcinoma MCF-7 cells.
Nutrition and cancer.
2014; 66(2):278-84. doi:
10.1080/01635581.2014.864776. [PMID: 24377707] - 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] - 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] - Man Ho Choi, Ju-Yeon Moon, Sung-Hee Cho, Bong Chul Chung, Eun Jig Lee. Metabolic alteration of urinary steroids in pre- and post-menopausal women, and men with papillary thyroid carcinoma.
BMC cancer.
2011 Aug; 11(?):342. doi:
10.1186/1471-2407-11-342. [PMID: 21824401] - 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] - Emanuela Taioli, Annie Im, Xia Xu, Timothy D Veenstra, Gretchen Ahrendt, Seymour Garte. Comparison of estrogens and estrogen metabolites in human breast tissue and urine.
Reproductive biology and endocrinology : RB&E.
2010 Aug; 8(?):93. doi:
10.1186/1477-7827-8-93. [PMID: 20678202] - 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] - 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] - 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] - Roni T Falk, Xia Xu, Larry Keefer, Timothy D Veenstra, Regina G Ziegler. A liquid chromatography-mass spectrometry method for the simultaneous measurement of 15 urinary estrogens and estrogen metabolites: assay reproducibility and interindividual variability.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2008 Dec; 17(12):3411-8. doi:
10.1158/1055-9965.epi-08-0355. [PMID: 19064556] - 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] - 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] - 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] - 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] - Masatoki Katayama, Kiyoshi Takamatsu, Satoru Kaneko, Keisuke Miyaji, Hiromichi Ishikawa, Yoshifumi Matsuda. HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector.
Journal of separation science.
2007 Sep; 30(14):2279-85. doi:
10.1002/jssc.200700096. [PMID: 17668912] - 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] - N Napoli, R Faccio, V Shrestha, S Bucchieri, G Battista Rini, R Armamento-Villareal. Estrogen metabolism modulates bone density in men.
Calcified tissue international.
2007 Apr; 80(4):227-32. doi:
10.1007/s00223-007-9014-4. [PMID: 17406768] - 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] - 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] - James J Grady. Analysis of change.
Methods in molecular biology (Clifton, N.J.).
2007; 404(?):261-71. doi:
10.1007/978-1-59745-530-5_13. [PMID: 18450054] - 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] - 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] - Vessela N Kristensen, Anya Tsalenko, Jurgen Geisler, Anne Faldaas, Grethe Irene Grenaker, Ole Christian Lingjaerde, Ståle Fjeldstad, Zohar Yakhini, Per Eystein Lønning, Anne-Lise Børresen-Dale. Multilocus analysis of SNP and metabolic data within a given pathway.
BMC genomics.
2006 Jan; 7(?):5. doi:
10.1186/1471-2164-7-5. [PMID: 16412218] - 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] - Daniel Lukaczer, Gary Darland, Matthew Tripp, DeAnn Liska, Robert H Lerman, Barbara Schiltz, Jeffrey S Bland. Clinical effects of a proprietary combination isoflavone nutritional supplement in menopausal women: a pilot trial.
Alternative therapies in health and medicine.
2005 Sep; 11(5):60-5. doi:
. [PMID: 16189949] - Jin Yoshida, Shinji Kumagai, Takeo Tabuchi, Hiroshi Kosaka, Susumu Akasaka, Hajime Oda. Effects of dioxin on metabolism of estrogens in waste incinerator workers.
Archives of environmental & occupational health.
2005 Jul; 60(4):215-22. doi:
10.3200/aeoh.60.4.215-222. [PMID: 17214292] - 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] - Kristin L Campbell, Kim C Westerlind, Vicki J Harber, Christine M Friedenreich, Kerry S Courneya. Associations between aerobic fitness and estrogen metabolites in premenopausal women.
Medicine and science in sports and exercise.
2005 Apr; 37(4):585-92. doi:
10.1249/01.mss.0000158185.23595.24. [PMID: 15809556] - 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] - Nikhil K Basu, Shigeki Kubota, Meselhy R Meselhy, Marco Ciotti, Bhabadeb Chowdhury, Masao Hartori, Ida S Owens. Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
The Journal of biological chemistry.
2004 Jul; 279(27):28320-9. doi:
10.1074/jbc.m401396200. [PMID: 15117964] - 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] - Charlotte Atkinson, Johanna W Lampe, Shelley S Tworoger, Cornelia M Ulrich, Deborah Bowen, Melinda L Irwin, Robert S Schwartz, Bharat K Rajan, Yutaka Yasui, John D Potter, Anne McTiernan. Effects of a moderate intensity exercise intervention on estrogen metabolism 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 May; 13(5):868-74. doi:
. [PMID: 15159321] - 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] - 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] - Claudia Weidler, Peter Härle, Joerg Schedel, Martin Schmidt, Jürgen Schölmerich, Rainer H Straub. Patients with rheumatoid arthritis and systemic lupus erythematosus have increased renal excretion of mitogenic estrogens in relation to endogenous antiestrogens.
The Journal of rheumatology.
2004 Mar; 31(3):489-94. doi:
. [PMID: 14994392] - 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] - 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] - Chi-Chen Hong, Bing-Kou Tang, Geoffrey L Hammond, David Tritchler, Martin Yaffe, Norman F Boyd. Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study.
Breast cancer research : BCR.
2004; 6(4):R352-65. doi:
10.1186/bcr798. [PMID: 15217502] - Chi-Chen Hong, Bing-Kou Tang, Venketeshwer Rao, Sanjiv Agarwal, Lisa Martin, David Tritchler, Martin Yaffe, Norman F Boyd. Cytochrome P450 1A2 (CYP1A2) activity, mammographic density, and oxidative stress: a cross-sectional study.
Breast cancer research : BCR.
2004; 6(4):R338-51. doi:
10.1186/bcr797. [PMID: 15217501] - Jane L Limer, Valerie Speirs. Phyto-oestrogens and breast cancer chemoprevention.
Breast cancer research : BCR.
2004; 6(3):119-27. doi:
10.1186/bcr781. [PMID: 15084232] - 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] - S Rinaldi, C N Moret, R Kaaks, C Biessy, M S Kurzer, H Déchaud, P H M Peeters, P A H van Noord. Reproducibility over time of measurements of androgens, estrogens and hydroxy estrogens in urine samples from post-menopausal women.
European journal of epidemiology.
2003; 18(5):417-24. doi:
10.1023/a:1024209122412. [PMID: 12889688] - 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] - Xia Xu, Regina G Ziegler, David J Waterhouse, Joseph E Saavedra, Larry K Keefer. Stable isotope dilution high-performance liquid chromatography-electrospray ionization mass spectrometry method for endogenous 2- and 4-hydroxyestrones in human urine.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2002 Nov; 780(2):315-30. doi:
10.1016/s1570-0232(02)00539-1. [PMID: 12401358] - Alfred O Mueck, Harald Seeger, Diethelm Wallwiener. Impact of hormone replacement therapy on endogenous estradiol metabolism in postmenopausal women.
Maturitas.
2002 Oct; 43(2):87-93. doi:
10.1016/s0378-5122(02)00160-3. [PMID: 12385856] - 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] - K Jaga, H Duvvi. Risk reduction for DDT toxicity and carcinogenesis through dietary modification.
The journal of the Royal Society for the Promotion of Health.
2001 Jun; 121(2):107-13. doi:
10.1177/146642400112100212. [PMID: 11467202] - M Vallée, C Albert, G Beaudry, D W Hum, A Bélanger. Isolation and characterization of the monkey UDP-glucuronosyltransferase cDNA clone monUGT1A01 active on bilirubin and estrogens.
The Journal of steroid biochemistry and molecular biology.
2001 Jun; 77(4-5):239-49. doi:
10.1016/s0960-0760(01)00062-0. [PMID: 11457662]
