Document Type : Review article
Authors
1 Department of Environmental Health Engineering, Zanjan University of Medical Sciences, Zanjan, Iran
2 Assistant Professor, Department of Environmental Health Engineering, Zanjan University of Medical Sciences, Zanjan, Iran
Abstract
Endocrine-disrupting compounds (EDCs) as active biological compounds can pose a threat to the environment through acute and chronic toxicity in organisms, accumulation in the ecosystem, and loss of habitats and biodiversity. They also have a range of possible adverse effects on environmental and ecological health. Estradiol, as one of the natural estrogenic hormones released by the humans and livestock, may exert endocrine-disrupting effects on the nanogram-per-liter range and cause serious problems for the aquatic organisms and animals in many aquatic systems. Various studies have reported the presence of synthetic estrogens such as 17 alpha-ethinyl estradiol (EE2) and natural estrogens including 17 beta-estradiol (E2) in wastewater sludge, surface water, river bed sediment, and also digested and activated sludge. The aim of the present study was to review and evaluate the endocrine disrupting compounds especially 17 beta-estradiol, as a representative of estrogen hormones present in the environment and their disturbing effects on humans and wildlife.
Keywords
Main Subjects
1.Chang HS, Choo KH, Lee B, Choi SJ. The methods of identification, analysis, and removal of endocrine disrupting compounds (EDCs) in water. J Hazard Mater. 2009;172(1):1- 12. doi: 10.1016/j.jhazmat.2009.06.135.
2.Belgiorno V, Rizzo L, Fatta D, Della Rocca C, Lofrano G, Nikolaou A, et al. Review on endocrine disrupting-emerging compounds in urban wastewater: occurrence and removal by photocatalysis and ultrasonic irradiation for wastewater reuse. Desalination. 2007;215(1-3):166-76. doi: 10.1016/j. desal.2006.10.035.
3.Zhang C, Li Y, Wang C, Niu L, Cai W. Occurrence of endocrine disrupting compounds in aqueous environment and their bacterial degradation: A review. Crit Rev Environ Sci Technol. 2016;46(1):1-59. doi: 10.1080/10643389.2015.1061881.
4.Esplugas S, Bila DM, Krause LGT, Dezotti M. Ozonation and advanced oxidation technologies to remove endocrine disrupting chemicals (EDCs) and pharmaceuticals and personal care products (PPCPs) in water effluents. J Hazard Mater. 2007;149(3):631-42. doi: 10.1016/j.jhazmat.2007.07.073.
5.Zeng Q, Li Y, Gu G, Zhao J, Zhang C, Luan J. Sorption and biodegradation of 17beta-estradiol by acclimated aerobic activated sludge and isolation of the bacterial strain. Environ Eng Sci. 2009;26(4):783-90. doi: 10.1089/ees.2008.0116.
6.Ouellette J, Dos Santos SC, Lepine F, Juteau P, Deziel E, Villemur R. High absorption of endocrine disruptors by Hytrel: towards the development of a two-phase partitioning bioreactor. J Chem Technol Biotechnol. 2013;88(1):119-25. doi: 10.1002/jctb.3864.
7.Sang Y, Xiong G, Maser E. Identification of a new steroid degrading bacterial strain H5 from the Baltic Sea and isolation of two estradiol inducible genes. J Steroid Biochem Mol Biol. 2012;129(1-2):22-30. doi: 10.1016/j.jsbmb.2011.01.018.
8.Weber S, Leuschner P, Kampfer P, Dott W, Hollender J. Degradation of estradiol and ethinyl estradiol by activated sludge and by a defined mixed culture. Appl Microbiol Biotechnol. 2005;67(1):106-12. doi: 10.1007/s00253-004- 1693-4.
9.Welshons WV, Thayer KA, Judy BM, Taylor JA, Curran EM, vom Saal FS. Large effects from small exposures. I. Mechanisms for endocrine-disrupting chemicals with estrogenic activity. Environ Health Perspect. 2003;111(8):994-1006. doi: 10.1289/ehp.5494.
10.Yang M, Park MS, Lee HS. Endocrine disrupting chemicals: human exposure and health risks. J Environ Sci Health C Environ Carcinog Ecotoxicol Rev. 2006;24(2):183-224. doi: 10.1080/10590500600936474.
11.Balabanic D, Rupnik M, Klemencic AK. Negative impact of endocrine-disrupting compounds on human reproductive health. Reprod Fertil Dev. 2011;23(3):403-16. doi: 10.1071/ rd09300.
12.Schug TT, Janesick A, Blumberg B, Heindel JJ. Endocrine disrupting chemicals and disease susceptibility. J SteroidBiochem Mol Biol. 2011;127(3-5):204-15. doi: 10.1016/j. jsbmb.2011.08.007.
13.Jarrell JF, Villeneuve D, Franklin C, Bartlett S, Wrixon W, Kohut J, Zouves CG. Contamination of human ovarian follicular fluid and serum by chlorinated organic compounds in three Canadian cities. CMAJ. 1993;148(8):1321.
14.Fernandez MF, Olmos B, Granada A, Lopez-Espinosa MJ, Molina-Molina JM, Fernandez JM, et al. Human exposure to endocrine-disrupting chemicals and prenatal risk factors for cryptorchidism and hypospadias: a nested case-control study. Environ Health Perspect. 2007;115 Suppl 1:8-14. doi: 10.1289/ehp.9351.
15.Colborn T, vom Saal FS, Soto AM. Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ Health Perspect. 1993;101(5):378-84. doi: 10.1289/ ehp.93101378.
16.Vos JG, Dybing E, Greim HA, Ladefoged O, Lambre C, Tarazona JV, et al. Health effects of endocrine-disrupting chemicals on wildlife, with special reference to the European situation. Crit Rev Toxicol. 2000;30(1):71-133. doi: 10.1080/10408440091159176.
17.Vethaak AD, Lahr J, Schrap SM, Belfroid AC, Rijs GB, Gerritsen A, et al. An integrated assessment of estrogenic contamination and biological effects in the aquatic environment of The Netherlands. Chemosphere. 2005;59(4):511-24. doi: 10.1016/j.chemosphere.2004.12.053.
18.Kirby MF, Allen YT, Dyer RA, Feist SW, Katsiadaki I, Matthiessen P, et al. Surveys of plasma vitellogenin and intersex in male flounder (Platichthys flesus) as measures of endocrine disruption by estrogenic contamination in United Kingdom estuaries: temporal trends, 1996 to 2001. Environ Toxicol Chem. 2004;23(3):748-58.
19.Jobling S, Coey S, Whitmore JG, Kime DE, Van Look KJ, McAllister BG, et al. Wild intersex roach (Rutilus rutilus) have reduced fertility. Biol Reprod. 2002;67(2):515-24.
20.Ying GG, Kookana RS, Dillon P. Sorption and degradation of selected five endocrine disrupting chemicals in aquifer material. Water Res. 2003;37(15):3785-91. doi: 10.1016/ s0043-1354(03)00261-6.
21.Yin GG, Kookana RS, Ru YJ. Occurrence and fate of hormone steroids in the environment. Environ Int. 2002;28(6):545-51.
22.Auriol M, Filali-Meknassi Y, Tyagi RD, Adams CD, Surampalli RY. Endocrine disrupting compounds removal from wastewater, a new challenge. Process Biochem. 2006;41(3):525-39. doi: 10.1016/j.procbio.2005.09.017.
23.Barnabe S, Brar SK, Tyagi RD, Beauchesne I, Surampalli RY. Pre-treatment and bioconversion of wastewater sludge to value-added products--fate of endocrine disrupting compounds. Sci Total Environ. 2009;407(5):1471-88. doi: 10.1016/j.scitotenv.2008.11.015.
24.Rezka P, Balcerzak W, Krylów M. Occurrence of synthetic and natural estrogenic hormones in the aquatic environment. Czasopismo Techniczne. 2016;2015(25):47-54. doi: 10.4467/2353737XCT.15.359.4824.
25.Snyder SA, Keith TL, Verbrugge DA, Snyder EM, Gross TS, Kannan K, et al. Analytical methods for detection of selected estrogenic compounds in aqueous mixtures. Environ Sci Technol. 1999;33(16):2814-20. doi: 10.1021/es981294f.
26.Brossa L, Marce RM, Borrull F, Pocurull E. Occurrence of twenty-six endocrine-disrupting compounds in environmental water samples from Catalonia, Spain. Environ Toxicol Chem. 2005;24(2):261-7.
27.Belfroid AC, Van der Horst A, Vethaak AD, Schafer AJ, Rijs GB, Wegener J, et al. Analysis and occurrence of estrogenic hormones and their glucuronides in surface water and waste water in The Netherlands. Sci Total Environ. 1999;225(1- 2):101-8.
28.Huang CH, Sedlak DL. Analysis of estrogenic hormones in municipal wastewater effluent and surface water using enzymelinked immunosorbent assay and gas chromatography/tandem mass spectrometry. Environ Toxicol Chem. 2001;20(1):133-9.
29.Ternes TA, Stumpf M, Mueller J, Haberer K, Wilken RD, Servos M. Behavior and occurrence of estrogens in municipal sewage treatment plants--I. Investigations in Germany, Canada and Brazil. Sci Total Environ. 1999;225(1-2):81-90.
30.Cargouet M, Perdiz D, Mouatassim-Souali A, TamisierKarolak S, Levi Y. Assessment of river contamination by estrogenic compounds in Paris area (France). Sci Total Environ. 2004;324(1-3):55-66. doi: 10.1016/j.scitotenv.2003.10.035.
31.Xiao XY, McCalley DV, McEvoy J. Analysis of estrogens in river water and effluents using solid-phase extraction and gas chromatography-negative chemical ionisation mass spectrometry of the pentafluorobenzoyl derivatives. J Chromatogr A. 2001;923(1-2):195-204.
32.Lagana A, Bacaloni A, De Leva I, Faberi A, Fago G, Marino A. Analytical methodologies for determining the occurrence of endocrine disrupting chemicals in sewage treatment plants and natural waters. Anal Chim Acta. 2004;501(1):79-88. doi: 10.1016/j.aca.2003.09.020.
33.Ismail A, Hazizan AF, Zulkifli SZ, Mohamat-Yusuff F, Omar H, Arizono K. Determination of 17beta-estradiol concentration in aquatic environment of Peninsular Malaysia using the ELISA technique. Life Sci J. 2014;11(8):673-9.
34.Isobe T, Shiraishi H, Yasuda M, Shinoda A, Suzuki H, Morita M. Determination of estrogens and their conjugates in water using solid-phase extraction followed by liquid chromatographytandem mass spectrometry. J Chromatogr A. 2003;984(2):195- 202.
35.Atkinson SK, Marlatt VL, Kimpe LE, Lean DR, Trudeau VL, Blais JM. The occurrence of steroidal estrogens in south-eastern Ontario wastewater treatment plants. Sci Total Environ. 2012;430:119-25. doi: 10.1016/j.scitotenv.2012.04.069.
36.Yuan X, Li T, Zhou L, Zhao X. Characteristics and risk assessment of estrogenic compounds in rivers of southern Jiangsu province, China. IERI Procedia. 2014;9:176-84. doi: 10.1016/j.ieri.2014.09.059.
37.Spengler P, Korner W, Metzger JW. Substances with estrogenic activity in effluents of sewage treatment plants in southwestern Germany. 1. Chemical analysis. Environ Toxicol Chem. 2001;20(10):2133-41.
38.Petrovic M, Sole M, Lopez de Alda MJ, Barcelo D. Endocrine disruptors in sewage treatment plants, receiving river waters, and sediments: integration of chemical analysis and biological effects on feral carp. Environ Toxicol Chem. 2002;21(10):2146- 56.
39.Desbrow C, Routledge EJ, Brighty GC, Sumpter JP, Waldock M. Identification of estrogenic chemicals in STW effluent. 1. Chemical fractionation and in vitro biological screening. Environ Sci Technol. 1998;32(11):1549-58. doi: 10.1021/ es9707973.
40.Pauwels B, Noppe H, De Brabander H, Verstraete W. Comparison of steroid hormone concentrations in domestic and hospital wastewater treatment plants. J Environ Eng. 2008;134(11):933-6. doi: 10.1061/(ASCE)0733- 9372(2008)134:11(933).
41.Jafari AJ, Pourkabireh Abbasabad R, Salehzadeh A. Endocrine disrupting contaminants in water resources and sewage in Hamadan City of Iran. J Environ Health Sci Eng. 2009;6(2):89- 96.
42.Hassani G, Babaei A, Takdastan A, Shirmardi M, Yousefian F, Mohammadi MJ. Occurrence and fate of 17beta -estradiol in water resources and wastewater in Ahvaz, Iran. Global Nest J. 2016;18(4):855-66. doi: 10.30955/gnj.002053.
43.Mohagheghian A, Nabizadeh R, Mesdghinia A, Rastkari N, Mahvi AH, Alimohammadi M, et al. Distribution of estrogenic steroids in municipal wastewater treatment plantsin Tehran, Iran. J Environ Health Sci Eng. 2014;12(1):97. doi: 10.1186/2052-336x-12-97.
44.Clouzot L, Doumenq P, Roche N, Marrot B. Kinetic parameters for 17alpha-ethinylestradiol removal by nitrifying activated sludge developed in a membrane bioreactor. Bioresour Technol. 2010;101(16):6425-31. doi: 10.1016/j. biortech.2010.03.039.
45.Liu B, Liu X. Direct photolysis of estrogens in aqueous solutions. Sci Total Environ. 2004;320(2-3):269-74. doi: 10.1016/j.scitotenv.2003.08.005.
46.Yoon Y, Westerhoff P, Snyder SA, Esparza M. HPLCfluorescence detection and adsorption of bisphenol A, 17beta-estradiol, and 17alpha-ethynyl estradiol on powdered activated carbon. Water Res. 2003;37(14):3530-7. doi: 10.1016/S0043-1354(03)00239-2.
47.Mai J, Sun W, Xiong L, Liu Y, Ni J. Titanium dioxide mediated photocatalytic degradation of 17beta-estradiol in aqueous solution. Chemosphere. 2008;73(4):600-6. doi: 10.1016/j. chemosphere.2008.05.073.
48.Yaping Z, Jiangyong H. Photo-Fenton degradation of 17betaestradiol in presence of alpha-FeOOHR and H2O2. Appl Catal B. 2008;78(3):250-8. doi: 10.1016/j.apcatb.2007.09.026.
49.Villemur R, Dos Santos SC, Ouellette J, Juteau P, Lepine F, Deziel E. Biodegradation of endocrine disruptors in solidliquid two-phase partitioning systems by enrichment cultures. Appl Environ Microbiol. 2013;79(15):4701-11. doi: 10.1128/ aem.01239-13.
50.San-Valero P, Gabaldon C, Penya-roja JM, Quijano G. Enhanced styrene removal in a two-phase partitioning bioreactor operated as a biotrickling filter: Towards full-scale applications. Chem Eng J. 2017;309:588-95. doi: 10.1016/j. cej.2016.10.054.
51.Moore K, McGuire KI, Gordon R, Woodruff TJ. Birth control hormones in water: separating myth from fact. Contraception. 2011;84(2):115-8. doi: 10.1016/j.contraception.2011.04.014.
2.Belgiorno V, Rizzo L, Fatta D, Della Rocca C, Lofrano G, Nikolaou A, et al. Review on endocrine disrupting-emerging compounds in urban wastewater: occurrence and removal by photocatalysis and ultrasonic irradiation for wastewater reuse. Desalination. 2007;215(1-3):166-76. doi: 10.1016/j. desal.2006.10.035.
3.Zhang C, Li Y, Wang C, Niu L, Cai W. Occurrence of endocrine disrupting compounds in aqueous environment and their bacterial degradation: A review. Crit Rev Environ Sci Technol. 2016;46(1):1-59. doi: 10.1080/10643389.2015.1061881.
4.Esplugas S, Bila DM, Krause LGT, Dezotti M. Ozonation and advanced oxidation technologies to remove endocrine disrupting chemicals (EDCs) and pharmaceuticals and personal care products (PPCPs) in water effluents. J Hazard Mater. 2007;149(3):631-42. doi: 10.1016/j.jhazmat.2007.07.073.
5.Zeng Q, Li Y, Gu G, Zhao J, Zhang C, Luan J. Sorption and biodegradation of 17beta-estradiol by acclimated aerobic activated sludge and isolation of the bacterial strain. Environ Eng Sci. 2009;26(4):783-90. doi: 10.1089/ees.2008.0116.
6.Ouellette J, Dos Santos SC, Lepine F, Juteau P, Deziel E, Villemur R. High absorption of endocrine disruptors by Hytrel: towards the development of a two-phase partitioning bioreactor. J Chem Technol Biotechnol. 2013;88(1):119-25. doi: 10.1002/jctb.3864.
7.Sang Y, Xiong G, Maser E. Identification of a new steroid degrading bacterial strain H5 from the Baltic Sea and isolation of two estradiol inducible genes. J Steroid Biochem Mol Biol. 2012;129(1-2):22-30. doi: 10.1016/j.jsbmb.2011.01.018.
8.Weber S, Leuschner P, Kampfer P, Dott W, Hollender J. Degradation of estradiol and ethinyl estradiol by activated sludge and by a defined mixed culture. Appl Microbiol Biotechnol. 2005;67(1):106-12. doi: 10.1007/s00253-004- 1693-4.
9.Welshons WV, Thayer KA, Judy BM, Taylor JA, Curran EM, vom Saal FS. Large effects from small exposures. I. Mechanisms for endocrine-disrupting chemicals with estrogenic activity. Environ Health Perspect. 2003;111(8):994-1006. doi: 10.1289/ehp.5494.
10.Yang M, Park MS, Lee HS. Endocrine disrupting chemicals: human exposure and health risks. J Environ Sci Health C Environ Carcinog Ecotoxicol Rev. 2006;24(2):183-224. doi: 10.1080/10590500600936474.
11.Balabanic D, Rupnik M, Klemencic AK. Negative impact of endocrine-disrupting compounds on human reproductive health. Reprod Fertil Dev. 2011;23(3):403-16. doi: 10.1071/ rd09300.
12.Schug TT, Janesick A, Blumberg B, Heindel JJ. Endocrine disrupting chemicals and disease susceptibility. J SteroidBiochem Mol Biol. 2011;127(3-5):204-15. doi: 10.1016/j. jsbmb.2011.08.007.
13.Jarrell JF, Villeneuve D, Franklin C, Bartlett S, Wrixon W, Kohut J, Zouves CG. Contamination of human ovarian follicular fluid and serum by chlorinated organic compounds in three Canadian cities. CMAJ. 1993;148(8):1321.
14.Fernandez MF, Olmos B, Granada A, Lopez-Espinosa MJ, Molina-Molina JM, Fernandez JM, et al. Human exposure to endocrine-disrupting chemicals and prenatal risk factors for cryptorchidism and hypospadias: a nested case-control study. Environ Health Perspect. 2007;115 Suppl 1:8-14. doi: 10.1289/ehp.9351.
15.Colborn T, vom Saal FS, Soto AM. Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ Health Perspect. 1993;101(5):378-84. doi: 10.1289/ ehp.93101378.
16.Vos JG, Dybing E, Greim HA, Ladefoged O, Lambre C, Tarazona JV, et al. Health effects of endocrine-disrupting chemicals on wildlife, with special reference to the European situation. Crit Rev Toxicol. 2000;30(1):71-133. doi: 10.1080/10408440091159176.
17.Vethaak AD, Lahr J, Schrap SM, Belfroid AC, Rijs GB, Gerritsen A, et al. An integrated assessment of estrogenic contamination and biological effects in the aquatic environment of The Netherlands. Chemosphere. 2005;59(4):511-24. doi: 10.1016/j.chemosphere.2004.12.053.
18.Kirby MF, Allen YT, Dyer RA, Feist SW, Katsiadaki I, Matthiessen P, et al. Surveys of plasma vitellogenin and intersex in male flounder (Platichthys flesus) as measures of endocrine disruption by estrogenic contamination in United Kingdom estuaries: temporal trends, 1996 to 2001. Environ Toxicol Chem. 2004;23(3):748-58.
19.Jobling S, Coey S, Whitmore JG, Kime DE, Van Look KJ, McAllister BG, et al. Wild intersex roach (Rutilus rutilus) have reduced fertility. Biol Reprod. 2002;67(2):515-24.
20.Ying GG, Kookana RS, Dillon P. Sorption and degradation of selected five endocrine disrupting chemicals in aquifer material. Water Res. 2003;37(15):3785-91. doi: 10.1016/ s0043-1354(03)00261-6.
21.Yin GG, Kookana RS, Ru YJ. Occurrence and fate of hormone steroids in the environment. Environ Int. 2002;28(6):545-51.
22.Auriol M, Filali-Meknassi Y, Tyagi RD, Adams CD, Surampalli RY. Endocrine disrupting compounds removal from wastewater, a new challenge. Process Biochem. 2006;41(3):525-39. doi: 10.1016/j.procbio.2005.09.017.
23.Barnabe S, Brar SK, Tyagi RD, Beauchesne I, Surampalli RY. Pre-treatment and bioconversion of wastewater sludge to value-added products--fate of endocrine disrupting compounds. Sci Total Environ. 2009;407(5):1471-88. doi: 10.1016/j.scitotenv.2008.11.015.
24.Rezka P, Balcerzak W, Krylów M. Occurrence of synthetic and natural estrogenic hormones in the aquatic environment. Czasopismo Techniczne. 2016;2015(25):47-54. doi: 10.4467/2353737XCT.15.359.4824.
25.Snyder SA, Keith TL, Verbrugge DA, Snyder EM, Gross TS, Kannan K, et al. Analytical methods for detection of selected estrogenic compounds in aqueous mixtures. Environ Sci Technol. 1999;33(16):2814-20. doi: 10.1021/es981294f.
26.Brossa L, Marce RM, Borrull F, Pocurull E. Occurrence of twenty-six endocrine-disrupting compounds in environmental water samples from Catalonia, Spain. Environ Toxicol Chem. 2005;24(2):261-7.
27.Belfroid AC, Van der Horst A, Vethaak AD, Schafer AJ, Rijs GB, Wegener J, et al. Analysis and occurrence of estrogenic hormones and their glucuronides in surface water and waste water in The Netherlands. Sci Total Environ. 1999;225(1- 2):101-8.
28.Huang CH, Sedlak DL. Analysis of estrogenic hormones in municipal wastewater effluent and surface water using enzymelinked immunosorbent assay and gas chromatography/tandem mass spectrometry. Environ Toxicol Chem. 2001;20(1):133-9.
29.Ternes TA, Stumpf M, Mueller J, Haberer K, Wilken RD, Servos M. Behavior and occurrence of estrogens in municipal sewage treatment plants--I. Investigations in Germany, Canada and Brazil. Sci Total Environ. 1999;225(1-2):81-90.
30.Cargouet M, Perdiz D, Mouatassim-Souali A, TamisierKarolak S, Levi Y. Assessment of river contamination by estrogenic compounds in Paris area (France). Sci Total Environ. 2004;324(1-3):55-66. doi: 10.1016/j.scitotenv.2003.10.035.
31.Xiao XY, McCalley DV, McEvoy J. Analysis of estrogens in river water and effluents using solid-phase extraction and gas chromatography-negative chemical ionisation mass spectrometry of the pentafluorobenzoyl derivatives. J Chromatogr A. 2001;923(1-2):195-204.
32.Lagana A, Bacaloni A, De Leva I, Faberi A, Fago G, Marino A. Analytical methodologies for determining the occurrence of endocrine disrupting chemicals in sewage treatment plants and natural waters. Anal Chim Acta. 2004;501(1):79-88. doi: 10.1016/j.aca.2003.09.020.
33.Ismail A, Hazizan AF, Zulkifli SZ, Mohamat-Yusuff F, Omar H, Arizono K. Determination of 17beta-estradiol concentration in aquatic environment of Peninsular Malaysia using the ELISA technique. Life Sci J. 2014;11(8):673-9.
34.Isobe T, Shiraishi H, Yasuda M, Shinoda A, Suzuki H, Morita M. Determination of estrogens and their conjugates in water using solid-phase extraction followed by liquid chromatographytandem mass spectrometry. J Chromatogr A. 2003;984(2):195- 202.
35.Atkinson SK, Marlatt VL, Kimpe LE, Lean DR, Trudeau VL, Blais JM. The occurrence of steroidal estrogens in south-eastern Ontario wastewater treatment plants. Sci Total Environ. 2012;430:119-25. doi: 10.1016/j.scitotenv.2012.04.069.
36.Yuan X, Li T, Zhou L, Zhao X. Characteristics and risk assessment of estrogenic compounds in rivers of southern Jiangsu province, China. IERI Procedia. 2014;9:176-84. doi: 10.1016/j.ieri.2014.09.059.
37.Spengler P, Korner W, Metzger JW. Substances with estrogenic activity in effluents of sewage treatment plants in southwestern Germany. 1. Chemical analysis. Environ Toxicol Chem. 2001;20(10):2133-41.
38.Petrovic M, Sole M, Lopez de Alda MJ, Barcelo D. Endocrine disruptors in sewage treatment plants, receiving river waters, and sediments: integration of chemical analysis and biological effects on feral carp. Environ Toxicol Chem. 2002;21(10):2146- 56.
39.Desbrow C, Routledge EJ, Brighty GC, Sumpter JP, Waldock M. Identification of estrogenic chemicals in STW effluent. 1. Chemical fractionation and in vitro biological screening. Environ Sci Technol. 1998;32(11):1549-58. doi: 10.1021/ es9707973.
40.Pauwels B, Noppe H, De Brabander H, Verstraete W. Comparison of steroid hormone concentrations in domestic and hospital wastewater treatment plants. J Environ Eng. 2008;134(11):933-6. doi: 10.1061/(ASCE)0733- 9372(2008)134:11(933).
41.Jafari AJ, Pourkabireh Abbasabad R, Salehzadeh A. Endocrine disrupting contaminants in water resources and sewage in Hamadan City of Iran. J Environ Health Sci Eng. 2009;6(2):89- 96.
42.Hassani G, Babaei A, Takdastan A, Shirmardi M, Yousefian F, Mohammadi MJ. Occurrence and fate of 17beta -estradiol in water resources and wastewater in Ahvaz, Iran. Global Nest J. 2016;18(4):855-66. doi: 10.30955/gnj.002053.
43.Mohagheghian A, Nabizadeh R, Mesdghinia A, Rastkari N, Mahvi AH, Alimohammadi M, et al. Distribution of estrogenic steroids in municipal wastewater treatment plantsin Tehran, Iran. J Environ Health Sci Eng. 2014;12(1):97. doi: 10.1186/2052-336x-12-97.
44.Clouzot L, Doumenq P, Roche N, Marrot B. Kinetic parameters for 17alpha-ethinylestradiol removal by nitrifying activated sludge developed in a membrane bioreactor. Bioresour Technol. 2010;101(16):6425-31. doi: 10.1016/j. biortech.2010.03.039.
45.Liu B, Liu X. Direct photolysis of estrogens in aqueous solutions. Sci Total Environ. 2004;320(2-3):269-74. doi: 10.1016/j.scitotenv.2003.08.005.
46.Yoon Y, Westerhoff P, Snyder SA, Esparza M. HPLCfluorescence detection and adsorption of bisphenol A, 17beta-estradiol, and 17alpha-ethynyl estradiol on powdered activated carbon. Water Res. 2003;37(14):3530-7. doi: 10.1016/S0043-1354(03)00239-2.
47.Mai J, Sun W, Xiong L, Liu Y, Ni J. Titanium dioxide mediated photocatalytic degradation of 17beta-estradiol in aqueous solution. Chemosphere. 2008;73(4):600-6. doi: 10.1016/j. chemosphere.2008.05.073.
48.Yaping Z, Jiangyong H. Photo-Fenton degradation of 17betaestradiol in presence of alpha-FeOOHR and H2O2. Appl Catal B. 2008;78(3):250-8. doi: 10.1016/j.apcatb.2007.09.026.
49.Villemur R, Dos Santos SC, Ouellette J, Juteau P, Lepine F, Deziel E. Biodegradation of endocrine disruptors in solidliquid two-phase partitioning systems by enrichment cultures. Appl Environ Microbiol. 2013;79(15):4701-11. doi: 10.1128/ aem.01239-13.
50.San-Valero P, Gabaldon C, Penya-roja JM, Quijano G. Enhanced styrene removal in a two-phase partitioning bioreactor operated as a biotrickling filter: Towards full-scale applications. Chem Eng J. 2017;309:588-95. doi: 10.1016/j. cej.2016.10.054.
51.Moore K, McGuire KI, Gordon R, Woodruff TJ. Birth control hormones in water: separating myth from fact. Contraception. 2011;84(2):115-8. doi: 10.1016/j.contraception.2011.04.014.
)