Phytoestrogens and mycoestrogens in surface waters - Their sources, occurrence, and potential contribution to estrogenic activity

Environment International

Volumn 81, Issue , 2015, Pages 26-44

  Jarošová, Barbora ^a   Javůrek, Jakub ^a   Adamovský, Ondřej ^a   Hilscherová, Klára ^a  

^a MASARYK UNIVERSITY   (Czech Republic)

Author keywords

Estrogenic equivalent; Estrogenicity; Flavonoids; Mycoestrogen; Phytoestrogen; Phytosterols; Relative potency; Sterol; Surface waters

Indexed keywords

ALCOHOLS; CHEMICAL ANALYSIS; FLAVONOIDS; METABOLITES;

ESTROGENIC EQUIVALENT; ESTROGENICITY; MYCOESTROGEN; PHYTOESTROGENES; PHYTOSTEROLS; RELATIVE POTENCIES; STEROL;

SURFACE WATERS;

BIOCHANIN A; DAIDZEIN; EQUOL; ESTRADIOL; ESTROGEN; FRESH WATER; GENISTEIN; MYCOESTROGEN; PHYTOESTROGEN; SITOSTEROL; SURFACE WATER; UNCLASSIFIED DRUG; ZEARALENONE; ISOFLAVONE DERIVATIVE; WATER POLLUTANT;

CONCENTRATION (COMPOSITION); ESTROGENIC COMPOUND; FISH; METABOLITE; STEROL; SURFACE WATER;

CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); ECOTOXICITY; ENVIRONMENTAL EXPOSURE; ESTROGEN ACTIVITY; FISH; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; POLLUTION TRANSPORT; PRIORITY JOURNAL; REVIEW; WATER CONTAMINATION; ANALYSIS; ANIMAL; TOXICITY; WATER POLLUTANT;

ANIMALS; ISOFLAVONES; PHYTOESTROGENS; WATER POLLUTANTS, CHEMICAL;

EID: 84928339035     PISSN: 01604120     EISSN: 18736750     Source Type: Journal    
DOI: 10.1016/j.envint.2015.03.019     Document Type: Review

References (101)

1. Alvarez D.A., Shappell N.W., Billey L.O., Bermudez D.S., Wilson V.S., Kolpin D.W., et al. Bioassay of estrogenicity and chemical analyses of estrogens in streams across the United States associated with livestock operations. Water Res. 2013, 47(10):3347-3363. (Jun 15).
2. Andrade P.B., Barbosa M., Matos R.P., Lopes G., Vinholes J., Mouga T., et al. Valuable compounds in macroalgae extracts. Food Chem. 2013, 138(2-3):1819-1828. (Jun 1).
3. Bacaloni A., Cavaliere C., Faberi A., Foglia P., Samperi R., Laganà A. Determination of isoflavones and coumestrol in river water and domestic wastewater sewage treatment plants. Anal. Chim. Acta 2005, 531(2):229-237. (Feb).
4. Bakos K., Kovács R., Staszny Á., Sipos D.K., Urbányi B., Müller F., et al. Developmental toxicity and estrogenic potency of zearalenone in zebrafish (Danio rerio). Aquat. Toxicol. 2013, 15:136-137. (Jul, 13-21).
5. Basen T., Rothhaupt K.O., Martin-Creuzburg D. Absence of sterols constrains food quality of cyanobacteria for an invasive freshwater bivalve. Oecologia 2012, 170(1):57-64. (Sep).
6. Bennetts H.W., Underwood E.J., Shier F.L. A specific breeding problem of sheep on subterranean clover pastures in Western Australia. Aust. Vet. J. 1946, 22:2-12. (Feb).
7. Bovee T.F.H., Helsdingen R.J.R., Rietjens I.M.C.M., Keijer J., Hoogenboom R.L.A.P. Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. J. Steroid Biochem. Mol. Biol. 2004, 91(3):99-109. (Jul).
8. Bovee T.F.H., Schoonen W.G.E.J., Hamers A.R.M., Bento M.J., Peijnenburg A.A.C.M. Screening of synthetic and plant-derived compounds for (anti)estrogenic and (anti)androgenic activities. Anal. Bioanal. Chem. 2008, 390(4):1111-1119. (Feb).
9. Breinholt V., Larsen J.C. Detection of weak estrogenic flavonoids using a recombinant yeast strain and a modified MCF7 cell proliferation assay. Chem. Res. Toxicol. 1998, 622-629.
10. Bucheli T.D., Wettstein F.E., Hartmann N., Erbs M., Vogelgsang S., Forrer H.-R., et al. Fusarium mycotoxins: overlooked aquatic micropollutants?. J. Agric. Food Chem. Am. Chem. Soc. 2008, 56(3):1029-1034. (Feb 13).
11. Cain T., Kolpin D., Vargo J.D., Wichman M.D. Occurrence of Antibiotics, Pharmaceuticals and Sterols at Select Surface and Wastewater Sites in Iowa 2008, 151-157.
12. Cherdshewasart W., Mahapanichkul T., Boonchird C. Estrogenic and anti-estrogenic activities of the Thai traditional herb, Butea superba Roxb. Biosci. Biotechnol. Biochem. 2010, 74(11):2176-2182.
13. Clotfelter E.D., Gendelman H.K. Exposure to environmentally relevant concentrations of genistein during activation does not affect sperm motility in the fighting fish Betta splendens. Biomed. Res. Int. 2014, 2014:1-5.
14. Clotfelter E.D., Rodriguez A.C. Behavioral changes in fish exposed to phytoestrogens. Environ. Pollut. 2006, 144(3):833-839. (Dec).
15. Coldham N., Dave M., Sivapathasundaram S., McDonnell D., Connor C., Sauerl M. Evaluation of a recombinant yeast cell estrogen screening assay. Environ. Health Perspect. 1997, 105(7):734-742.
16. D'Alessandro T.L., Boersma-Maland B.J., Peterson T.G., Sfakianos J., Prasain J.K., Patel R.P., et al. Metabolism of phytoestrogen conjugates. Methods Enzymol. 2005, 400:316-342. (Jan).
17. Danish Ministry of the Environment Survey of Estrogenic Activity in the Danish Aquatic Environment 2005, 170.
18. Desbrow C., Routledge E., Brighty G., Sumpter J., Waldock M. Identification of estrogenic chemicals in STW effluent. 1. Chemical fractionation and in vitro biological screening. Environ. Sci. Technol. 1998, 97:1549-1558.
19. Dixon R.A. Phytoestrogens. Annu. Rev. Plant Biol. 2004, 55:225-261. (Jan).
20. Dudziak M. Analysis of zearalenone in aqueous environment using GC-MS. Pol. J. Environ. Stud. 2011, 20(1):231-235. (HARD, POST-OFFICE BOX, 10-718 OLSZTYN 5, POLAND).
21. Duong C.N., Ra J.S., Cho J., Kim S.D., Choi H.K., Park J.-H., et al. Estrogenic chemicals and estrogenicity in river waters of South Korea and seven Asian countries. Chemosphere 2010, 78(3):286-293. Elsevier Ltd., (Jan).
22. Erasmuson A.F., Scahill B.G., West D.M. Natural zeranol (a-zearalanol) in the urine of pasture-fed animals. J. Agric. Food Chem. 1994, 42:2721-2725.
23. 13C3-labeled internal standards. J. Agric. Food Chem. 2007, 55(21):8339-8345. (Oct 17).
24. Fernandez M.P., Ikonomou M.G., Buchanan I. An assessment of estrogenic organic contaminants in Canadian wastewaters. Sci. Total Environ. 2007, 250-269.
25. Frizzell C., Ndossi D., Verhaegen S., Dahl E., Eriksen G., Sørlie M., et al. Endocrine disrupting effects of zearalenone, alpha- and beta-zearalenol at the level of nuclear receptor binding and steroidogenesis. Toxicol. Lett. 2011, 206(2):210-217. (Oct 10).
26. Green C.C., Kelly A.M. Effect of the exogenous soyabean phyto-oestrogen genistein on sperm quality, ATP content and fertilization rates in channel catfish Ictalurus punctatus (Rafinesque) and walleye Sander vitreus (Mitchill). J. Fish Biol. 2008, 72(10):2485-2499. (Jun).
27. Gromadzka K., Waśkiewicz A., Goliński P., Swietlik J. Occurrence of estrogenic mycotoxin - zearalenone in aqueous environmental samples with various NOM content. Water Res. 2009, 43(4):1051-1059. (Mar).
28. Gutendorf B., Westendorf J. Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens. Toxicology 2001, 79-89.
29. Hartmann N., Erbs M., Wettstein F.E., Schwarzenbach R.P., Bucheli T.D. Quantification of estrogenic mycotoxins at the ng/L level in aqueous environmental samples using deuterated internal standards. J. Chromatogr. A 2007, 1138(1-2):132-140. (Jan 5).
30. Hartmann N., Erbs M., Wettstein F.E., Hörger C.C., Vogelgsang S., Forrer H.-R., et al. Environmental exposure to estrogenic and other myco- and phytotoxins. Chim. Int. J. Chem. 2008, 62(5):364-367. (May 28).
31. Hoerger C.C., Wettstein F.E., Hungerbühler K., Bucheli T.D. Occurrence and origin of estrogenic isoflavones in Swiss river waters. Environ. Sci. Technol. 2009, 43(16):6151-6157. (Aug 15).
32. Holbech H., Schröder K.D., Nielsen M.L., Brande-Lavridsen N., Holbech B.F., Bjerregaard P. Estrogenic effect of the phytoestrogen biochanin A in zebrafish, Danio rerio, and brown trout, Salmo trutta. Aquat. Toxicol. 2013, 144-145:19-25. (Nov 15).
33. Jarosova B., Blaha L., Vrana B., Randak T., Grabic R., Giesy J.P., et al. Changes in concentrations of hydrophilic organic contaminants and of endocrine-disrupting potential downstream of small communities located adjacent to headwaters. Environ. Int. 2012, 45:22-31. (Sep 15).
34. Jarosova B., Blaha L., Giesy J.P., Hilscherova K. What level of estrogenic activity determined by in vitro assays in municipal waste waters can be considered as safe?. Environ. Int. 2014, 64:98-109. (Dec 30).
35. Jefferson W.N., Patisaul H.B., Williams C.J. Reproductive consequences of developmental phytoestrogen exposure. Reproduction 2012, 143(3):247-260. (Mar).
36. Johns S.M., Denslow N.D., Kane M.D., Watanabe K.H., Orlando E.F., Sepúlveda M.S. Effects of estrogens and antiestrogens on gene expression of fathead minnow (Pimephales promelas) early life stages. Environ. Toxicol. 2011, 26(2):195-206. (Apr).
37. Johnson A.C., Aerni H.R., Gerritsen A., Gibert M., Giger W., Hylland K., et al. Comparing steroid estrogen, and nonylphenol content across a range of European sewage plants with different treatment and management practices. Water Res. 2005, 47-58.
38. Joung K.E., Kim Y.W., Sheen Y.Y. Assessment of the estrogenicity of isoflavonoids, using MCF-7-ERE-Luc cells. Arch. Pharm. Res. 2003, 26(9):756-762. (Sep).
39. Kalita J.C., Milligan S.R. In vitro estrogenic potency of phytoestrogen-glycosides and some plant flavanoids. Indian J. Sci. Technol. 2010, 3(12):1142-1147.
40. Kang J., Price W.E. Occurrence of phytoestrogens in municipal wastewater and surface waters. J. Environ. Monit. 2009, 11(Ml):1477-1483. (Aug).
41. Kang J., Price W.E., Hick L.A. Simultaneous determination of isoflavones and lignans at trace levels in natural waters and wastewater samples using liquid chromatography/electrospray ionization ion trap mass spectrometry. Rapid Commun. Mass Spectrom. 2006, 20(16):2411-2418. (Jan).
42. Kang H.K., Choi Y.-H., Kwon H., Lee S.-B., Kim D.-H., Sung C.K., et al. Estrogenic/antiestrogenic activities of an Epimedium koreanum extract and its major components: in vitro and in vivo studies. Food Chem. Toxicol. 2012, 50(8):2751-2759. (Aug).
43. Kawanishi M., Takamura-Enya T., Ermawati R., Shimohara C., Sakamoto M., Matsukawa K., et al. Detection of genistein as an estrogenic contaminant of river water in Osaka. Environ. Sci. Technol. 2004, 6424-6429.
44. Kazłowska K., Lin H.-T.V., Chang S.-H., Tsai G.-J. In vitro and in vivo anticancer effects of sterol fraction from red algae Porphyra dentata. Evid. Based Complement. Alternat. Med. 2013, 2013:493869. (Jan).
45. Kinnberg K. Evaluation of In Vitro Assays for Determination of Estrogenic Activity in the Environment 2003, Danish Environmental Protection Agency, Danish Ministry of the Environment.
46. Kiparissis Y., Hughes R., Metcalfe C., Ternes T. Identification of the isoflavonoid genistein in bleached Kraft mill effluent. Environ. Sci. Technol. 2001, 2423-2427.
47. Kiparissis Y., Balch G.C., Metcalfe T.L., Metcalfe C.D. Effects of the isoflavones genistein and equol on the gonadal development of Japanese medaka (Oryzias latipes). Environ. Health Perspect. 2003, 111(9):1158-1163. (Feb 5).
48. Kolpin D.W., Hoerger C.C., Meyer M.T., Wettstein F.E., Hubbard L.E., Bucheli T.D. Phytoestrogens and mycotoxins in Iowa streams: an examination of underinvestigated compounds in agricultural basins. J. Environ. Qual. 2010, 39(6):2089-2099.
49. Kolpin D.W., Schenzel J., Meyer M.T., Phillips P.J., Hubbard L.E., Scott T.-M., et al. Mycotoxins: diffuse and point source contributions of natural contaminants of emerging concern to streams. Sci. Total Environ. 2014, 470-471. (Feb 1, 669-76).
50. Kuster M., Azevedo D.A., López de Alda M.J., Aquino Neto F.R., Barceló D. Analysis of phytoestrogens, progestogens and estrogens in environmental waters from Rio de Janeiro (Brazil). Environ Int. 2009, 35(7):997-1003. Elsevier Ltd., (Oct).
51. 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. (Jan).
52. Le Guevel R., Pakdel F. Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. Hum. Reprod. 2001, 16(5):1030-1036. (May).
53. Leffers H., Naesby M., Vendelbo B., Skakkebaek N.E., Jørgensen M. Oestrogenic potencies of zeranol, oestradiol, diethylstilboestrol, bisphenol-A and genistein: implications for exposure assessment of potential endocrine disrupters. Hum. Reprod. 2001, 16(5):1037-1045. (May 1).
54. Lehtinen K.J., Mattsson K., Tana J., Engström C., Lerche O., Hemming J. Effects of wood-related sterols on the reproduction, egg survival, and offspring of brown trout (Salmo trutta lacustris L.). Ecotoxicol. Environ. Saf. 1999, 42(1):40-49. (Jan).
55. Leusch F.D.L., MacLatchy D.L. In vivo implants of β-sitosterol cause reductions of reactive cholesterol pools in mitochondria isolated from gonads of male goldfish (Carassius auratus). Gen. Comp. Endocrinol. 2003, 134(3):255-263. (Dec).
56. Leusch F.D.L., De Jager C., Levi Y., Lim R., Puijker L., Sacher F., et al. Comparison of five in vitro bioassays to measure estrogenic activity in environmental waters. Environ. Sci. Technol. 2010, 3853-3860.
57. Liggins J., Bluck L.J., Runswick S., Atkinson C., Coward W.A., Bingham S.A. Daidzein and genistein contents of vegetables. Br. J. Nutr. 2000, 84(5):717-725. (Nov).
58. Liu Z.H., Kanjo Y., Mizutani S. A review of phytoestrogens: their occurrence and fate in the environment. Water Res. 2010, 44(2):567-577.
59. Lundgren M.S., Novak P.J. Quantification of phytoestrogens in industrial waste streams. Environ. Toxicol. Chem. 2009, 28(11):2318.
60. MacLatchy D., Peters L., Nickle J., van der Kraak G. Exposure to beta-sitosterol alters the endocrine status of goldfish differently than 17beta-estradiol. Environ. Toxicol. Chem. 1997, 16(9):1895-1904. (Sep).
61. Maragos C.M. Zearalenone occurrence in surface waters in central Illinois, USA. Food Addit. Contam. Part B Surveill. 2012, 5(1):55-64. (Jan).
62. Massart F., Saggese G. Oestrogenic mycotoxin exposures and precocious pubertal development. Int. J. Androl. 2010, 369-376.
63. Matsumura A., Ghosh A., Pope G.S., Darbre P.D. Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells. J. Steroid Biochem. Mol. Biol. 2005, 94:431-443.
64. Matthiessen P., Arnold D., Johnson A.C., Pepper T.J. Contamination of headwater streams in the United Kingdom by oestrogenic hormones from livestock farms 2006, 367:616-630.
65. Mattsson K., Tana J., Engström C., Hemming J., Lehtinen K.J. Effects of wood-related sterols on the offspring of the viviparous blenny, Zoarces viviparus L. Ecotoxicol. Environ. Saf. 2001, 49(2):122-130. (Jun).
66. Metzler M., Pfeiffer E., Hildebrand A.A. Zearalenone and its metabolites as endocrine disrupting chemicals. World Mycotoxin J. 2010, 3(4):385-401. (Nov).
67. Minervini F., Giannoccaro A., Cavallini A., Visconti A. Investigations on cellular proliferation induced by zearalenone and its derivatives in relation to the estrogenic parameters. Toxicol. Lett. 2005, 159:272-283.
68. Molina-Molina J.-M., Real M., Jimenez-Diaz I., Belhassen H., Hedhili A., Torné P., et al. Assessment of estrogenic and anti-androgenic activities of the mycotoxin zearalenone and its metabolites using in vitro receptor-specific bioassays. Food Chem. Toxicol. 2014, 74C:233-239. (Oct 16).
69. Munkittrick K.R., McMaster M.E., McCarthy L.H., Servos M.R., Van Der Kraak G.J. An overview of recent studies on the potential of pulp-mill effluents to alter reproductive parameters in fish. J. Toxicol. Environ. Health B Crit. Rev. 1998, 1(4):347-371.
70. Murkies A.L., Wilcox G., Davis S.R. Clinical review 92: phytoestrogens. J. Clin. Endocrinol. Metab. 1998, 83(2):297-303. (Mar).
71. Nadzialek S., Vanparys C., Van der Heiden E., Michaux C., Brose F., Scippo M.-L., et al. Understanding the gap between the estrogenicity of an effluent and its real impact into the wild. Sci Total Environ. 2010, 408(4):812-821. Elsevier B.V., (Jan 15).
72. Newill H., Loske R., Wagner J., Johannes C., Lorenz R.L., Lehmann L. Oxidation products of stigmasterol interfere with the action of the female sex hormone 17beta-estradiol in cultured human breast and endometrium cell lines. Mol. Nutr. Food Res. 2007, 51(7):888-898. (Jul).
73. Panter G.H., Hutchinson T.H., Länge R., Lye C.M., Sumpter J.P., Zerulla M., et al. Utility of a juvenile fathead minnow screening assay for detecting (anti-)estrogenic substances. Environ. Toxicol. Chem. 2002, 21(2):319-326. (Feb).
74. Pawlowski S., Ternes T., Bonerz M., Kluczka T., van der Burg B. Combined in situ and in vitro assessment of the estrogenic activity of sewage and surface water samples. Toxicol. Sci. 2003, 57-65.
75. Pelissero C., Sumpter J.P. Steroids and "steroid-like" substances in fish diets. Aquaculture 1992, 107(4):283-301. (Nov).
76. Rearick D.C., Fleischhacker N.T., Kelly M.M., Arnold W.A., Novak P.J., Schoenfuss H.L. Phytoestrogens in the environment, I: occurrence and exposure effects on fathead minnows. Environ. Toxicol. Chem. 2014, 33(3):553-559. (Mar).
77. Ribeiro C., Pardal M.A.Â., Martinho F., Margalho R., Tiritan M.E., Rocha E., et al. Distribution of endocrine disruptors in the Mondego River estuary, Portugal. Environ. Monit. Assess. 2009, 149(1-4):183-193. (Feb).
78. Ribeiro C., Tiritan M.E., Rocha E., Rocha M.J. Seasonal and spatial distribution of several endocrine-disrupting compounds in the Douro River Estuary, Portugal. Arch. Environ. Contam. Toxicol. 2009, 56(1):1-11. (Jan).
79. Rocha M.J., Cruzeiro C., Rocha E. Development and validation of a GC-MS method for the evaluation of 17 endocrine disruptor compounds, including phytoestrogens and sitosterol, in coastal waters - their spatial and seasonal levels in Porto costal region (Portugal). J. Water Health 2013, 11(2):281-296. (Jun).
80. Rochester J.R., Millam J.R. Phytoestrogens and avian reproduction: exploring the evolution and function of phytoestrogens and possible role of plant compounds in the breeding ecology of wild birds. Comp. Biochem. Physiol. A Mol. Integr. Physiol. 2009, 154(3):279-288. (Nov).
81. Schenzel J., Hungerbühler K., Bucheli T.D. Mycotoxins in the environment: II. Occurrence and origin in Swiss river waters. Environ Sci Technol. 2012, 46(24):13076-13084. American Chemical Society, (Dec 18).
82. Schiller V., Wichmann A., Kriehuber R., Muth-Kohne E., Giesy J.P., Hecker M., et al. Studying the effects of genistein on gene expression of fish embryos as an alternative testing approach for endocrine disruption. Comp. Biochem. Physiol. C: Toxicol. Pharmacol. 2013, 41-53.
83. Schmitt S., Reifferscheid G., Claus E., Schlüsener M., Buchinger S. Effect directed analysis and mixture effects of estrogenic compounds in a sediment of the River Elbe. Environ. Sci. Pollut. Res. Int. 2012, 19(8):3350-3361. (Sep).
84. Scholz B., Liebezeit G. Screening for biological activities and toxicological effects of 63 phytoplankton species isolated from freshwater, marine and brackish water habitats. Harmful Algae 2012, 20:58-70. Elsevier B.V., (Dec).
85. Scholz S., Kordes C., Hamann J., Gutzeit H.O. Induction of vitellogenin in vivo and in vitro in the model teleost medaka (Oryzias latipes): comparison of gene expression and protein levels. Mar. Environ. Res. 2004, 57(3):235-244. (Apr).
86. Schwartz P., Thorpe K.L., Bucheli T.D., Wettstein F.E., Burkhardt-Holm P. Short-term exposure to the environmentally relevant estrogenic mycotoxin zearalenone impairs reproduction in fish. Sci Total Environ. 2010, 409(2):326-333. Elsevier B.V., (Dec 15).
87. Schwartz P., Bucheli T.D., Wettstein F.E., Burkhardt-Holm P. Life-cycle exposure to the estrogenic mycotoxin zearalenone affects zebrafish (Danio rerio) development and reproduction. Environ. Toxicol. 2013, 28(5):276-289. (May).
88. Shappell N.W., Mostrom M.S., Lenneman E.M. E-Screen evaluation of sugar beet feedstuffs in a case of reduced embryo transfer efficiencies in cattle: the role of phytoestrogens and zearalenone. In Vitro Cell. Dev. Biol. Anim. 2012, 48:216-228.
89. Smeds A.I., Willför S.M., Pietarinen S.P., Peltonen-Sainio P., Reunanen M.H.T. Occurrence of "mammalian" lignans in plant and water sources. Planta 2007, 226(3):639-646.
90. Stackelberg P.E., Furlong E.T., Meyer M.T., Zaugg S.D., Henderson A.K., Reissman D.B. Persistence of pharmaceutical compounds and other organic wastewater contaminants in a conventional drinking-water-treatment plant. Sci. Total Environ. 2004, 329(1-3):99-113. (Aug).
91. Stackelberg P.E., Gibs J., Furlong E.T., Meyer M.T., Zaugg S.D., Lippincott R.L. Efficiency of conventional drinking-water-treatment processes in removal of pharmaceuticals and other organic compounds. Sci. Total Environ. 2007, 377(2-3):255-272. (May).
92. Stanford B.D., Snyder S.A., Trenholm R.A., Holady J.C., Vanderford B.J. Estrogenic activity of US drinking waters: a relative exposure comparison. J. Am. Water Work Assoc. 2010, 102(12):55-65.
93. Stevenson L.M., Brown A.C., Montgomery T.M., Clotfelter E.D. Reproductive consequences of exposure to waterborne phytoestrogens in male fighting fish Betta splendens. Arch. Environ. Contam. Toxicol. 2011, 60(3):501-510. (Apr).
94. Sumpter J.P., Johnson A.C. 10th anniversary perspective: reflections on endocrine disruption in the aquatic environment: from known knowns to unknown unknowns (and many things in between). J. Environ. Monit. R. Soc. Chem. 2008, 1476-1485.
95. Sun Q., Deng S., Huang J., Shen G., Yu G. Contributors to estrogenic activity in wastewater from a large wastewater treatment plant in Beijing, China. Environ. Toxicol. Pharmacol. 2008, 25(1):20-26. (Jan).
96. Tremblay L., Van der Kraak G. Comparison between the effects of the phytosterol beta-sitosterol and pulp and paper mill effluents on sexually immature rainbow trout. Environ. Toxicol. Chem. 1999, 329-336.
97. Wang C., Wang L., Zhao Q., Chen J., Zheng L., Zheng M., et al. Cloud point extraction coupled with HPLC-DAD for the determination of genistein and daidzein in river water. Anal. Methods 2013, 5(15):3688.
98. Waśkiewicz A., Gromadzka K., Bocianowski J., Pluta P., Goliński P. Zearalenone contamination of the aquatic environment as a result of its presence in crops. Arh. Hig. Rada Toksikol. 2012, 63(4):429-435. (Dec).
99. Welshons W.V., Rottinghaus G.E., Nonneman D.J., Dolan-Timpe M., Ross P.F. A sensitive bioassay for detection of dietary estrogens in animal feeds. J. Vet. Diagn. Invest. 1990, 2(4):268-273. (Oct).
100. Whitten P.L., Patisaul H.B. Cross-species and interassay comparisons of phytoestrogen action. Environ. Health Perspect. 2001, 109:5-20. (Mar).
101. WHO, UNEP State of the Science of Endocrine Disrupting Chemicals 2012 2013, 1-296.