Phytoestrogens and anthropogenic estrogenic compounds

Environmental Toxicology and Chemistry

Volumn 17, Issue 1, 1998, Pages 119-126

  Safe, Stephen H ^a   Gaido, Kevin ^b  

^a TEXAS A AND M UNIVERSITY   (United States)

^b Institute of Toxicology   (United States)

Author keywords

Induced responses; Phytoestrogens; Xenoestrogens

Indexed keywords

4,4' ISOPROPYLIDENEDIPHENOL; ANDROGEN; AROMATIC HYDROCARBON; ESTROGEN; ESTROGEN DERIVATIVE; FLAVONOID; ORGANOCHLORINE PESTICIDE; PHTHALIC ACID; PHYTOESTROGEN; POLYCHLORINATED BIPHENYL; RETINOIC ACID; RETINOID X RECEPTOR; XENOBIOTIC AGENT;

BINDING AFFINITY; DIET; ESTROGEN ACTIVITY; HORMONE ACTION; HORMONE RELEASE; PRIORITY JOURNAL; RECEPTOR BINDING; REVIEW;

EID: 0031975058     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/1551-5028(1998)017<0119:PAAEC>2.3.CO;2     Document Type: Review

References (117)

1. Bulger WH, Kupfer D. 1985. Estrogenic activity of pesticides and other xenobiotics on the uterus and male reproductive tract. In Thomas JA, Korach KS, McLachlan JA, eds, Endocrine Toxicology. Raven, New York, NY, USA, pp 1-33.
2. Bradbury RB, White DE. 1955. Estrogens and related substances in plants. Vitam Horm 12:207-233.
3. Martin PM, Horwitz KB, Ryan DS, McGuire WL. 1978. Phytoestrogen interaction with estrogen receptors in human breast cancer cells. Endocrinology 103:1860-1867.
4. Cheng E, Yoder L, Story CD, Burroughs W. 1954. Estrogenic activity of some isoflavone derivatives. Science 120:575-577.
5. Kupfer D. 1975. Effects of pesticides and related compounds on steroid metabolism and function. Crit Rev Toxicol 4:83-124.
6. Clarkson TB, Anthony MS, Hughes CL Jr. 1995. Estrogenic soybean isoflavones and chronic disease. Trends Endocrinol Metab 6:11-16.
7. Moule OR, Braden AWH, Lamond DR. 1963. The significance of oestrogens in pasture plants in relation to animal production. Anim Breed Abstr 31:139-157.
8. Morley FHW, Axelsen A, Bennett D. 1964. Effects of grazing red clover (Trifolium pratensel) during the joining season on ewe fertility. Proc Aust Soc Anim Prod 5:58-61.
9. Bennetts HW, Underwood EJ, Shier FL. 1946. A specific breeding problem of sheep on subterranean clover pastures in Western Australia. Aust Vet J 22:2-12.
10. Shutt DA, Braden AWH. 1968. The significance of equol in relation to the oestrogenic responses in sheep ingesting clover with a high formononetin content. Aust J Agric Res 19:545-553.
11. Kaldas RS, Hughes CL Jr. 1989. Reproductive and general metabolic effects of phytoestrogens in mammals. Reprod Toxicol 3:81-89.
12. Shutt DA. 1976. The effects of plant estrogens on animal reproduction. Endeavour (Oxf) 35:110-113.
13. Whitten PL, Naftolin F. 1992. Effects of a phytoestrogen diet on estrogen-dependent reproductive processes in immature female rats. Steroids 57:56-61.
14. Whitten PL, Lewis C, Russell E, Naftolin F. 1995. Phytoestrogen influences on the development of behavior and gonadotropin function. Proc Soc Exp Biol Med 208:82-86.
15. Whitten PL, Lewis C, Naftolin F. 1993. A phytoestrogen diet induces the premature anovulatory syndrome in lactationally exposed female rats. Biol Reprod 49:1117-1121.
16. Jordan VC, Mittal S, Gosden B, Koch R, Lieberman ME. 1985. Structure-activity relationships of estrogens. Environ Health Perspect 61:91-110.
17. Tullner WW. 1961. Uterotrophic action of the insecticide methoxychlor. Science 133:647-648.
18. Bitman J, Cecil HC, Harris SJ, Fries GF. 1968. Estrogenic activity of o,p′-DDT in the mammalian uterus and avian oviduct. Science 162:371-372.
19. Herbst AL, Bern HA. 1981. Developmental Effects of Diethylslilbestrol (DES) in Pregnancy. Thieme-Stratton, New York, NY, USA.
20. Marselos M, Tomatis L. 1992. Diethylstilboestrol: I. Pharmacology, toxicology and carcinogenicity in humans. Eur J Cancer 28A:1182-1189.
21. Rotmensch J, Frey K, Hertst AL. 1988. Effects of female offspring and mothers after exposure to diethylstilbestrol. In Mori T, Nagasawa H, eds, Toxicity of Hormones in Perinatal Life. CRC, Boca Raton, FL, USA, pp 143-149.
22. Newbold RR, McLachlan JA. 1985. Diethylstilbestrol associated defects in murine genital tract development. In McLachlan JA, ed, Estrogens in the Environment. Elsevier, New York, NY, USA, pp 288-318.
23. Newbold R. 1995. Cellular and molecular effects of developmental exposure to diethylstilbestrol: Implications for other environmental estrogens. Environ Health Perspect 103:83-87.
24. Colborn T, Vom Saal FS, Soto AM, 1993. Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ Health Perspect 101:378-384.
25. Carlsen E, Giwercman A, Keiding N, Skakkebaek NE. 1992. Evidence for the decreasing quality of semen during the past 50 years. BMJ 305:609-612.
26. Sharpe RM, Skakkebaek NF. 1993. Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet 341:1392-1395.
27. Kelce WR, Stone CR, Laws SC, Gray LE. 1995. Persistent DDT metabolite p,p′-DDE is a potent androgen receptor antagonist. Nature 375:581-586.
28. Sharpe RM. 1995. Reproductive biology: Another DDT connection. Nature 375:538-539.
29. Auger J, Kuntsmann JM, Czyglik F, Jouannet P. 1985. Decline in semen quality among fertile men in Paris during the past 20 years. N Engl J Med 332:281-285.
30. Bendvold E, Gottlieb C, Bygdeman M, Eneroth P. 1991. Depressed semen quality in Swedish men from barren couples: A study over three decades. Arch Androl 26:189-194.
31. Irvine S, Cawood E, Richardson D, MacDonald E, Aitken J. 1996. Evidence of deteriorating semen quality in the United Kingdom: Birth cohort study in 577 men in Scotland over 11 years. Br Med J 312:467-471.
32. Fisch H, Goluboff ET, Oison JH, Feldshuh J, Broder SJ, Barad DH. 1996. Semen analyses in 1,283 men from the United States over a 25-year period: No decline in quality. Fertil Steril 65:1009-1014.
33. Paulsen CA, Berman NG, Wang C. 1996. Data from men in greater Seattle area reveals no downward trend in semen quality: Further evidence that deterioration of semen quality is not geographically uniform. Fertil Steril 65:1015-1020.
34. Bujan L, Mansat A, Pontonnier F, Mieusset R. 1996. Time series analysis of sperm concentration in fertile men in Toulouse, France between 1977 and 1992. Br Med J 312:471-472.
35. Macleod J, Wang Y. 1979. Male fertility potential in terms of semen quality: A review of the past, a study of the present. Fertil Steril 31:103-116.
36. Davis DL, Bradlow HL, Wolff M, Woodruff T, Hoel DG, Anton-Culver H. 1993. Medical hypothesis: Xenoestrogens as preventable causes of breast cancer. Environ Health Perspect 101:372-377.
37. Davis DL, Bradlow HL. 1995. Can environmental estrogens cause breast cancer? Sci Am 273:166-171.
38. Wolff MS, Toniolo PG, Leel EW, Rivera M, Dubin N. 1993. Blood levels of organochlorine residues and risk of breast cancer. J Natl Cancer Inst 85:648-652.
39. Falck F, Ricci A, Wolff MS, Godbold J, Deckers P. 1992. Pesticides and polychlorinated biphenyl residues in human breast lipids and their relation to breast cancer. Arch Environ Health 47:143-146.
40. Krieger N, Wolff MS, Hiatt RA, Rivera M, Vogelman J, Orentreich N. 1994. Breast cancer and serum organochlorines: A prospective study among white, black, and Asian women. J Natl Cancer Inst 86:589-599.
41. Key T, Reeves G. 1994. Organochlorines in the environment and breast cancer. Br Med J 308:1520-1521.
42. Ahlborg UG, Lipworth L, Titusernstoff L, Hsieh CC, Hanberg A. Baron J. Trichopoulos D, Adami HO. 1995. Organochlorine compounds in relation to breast cancer, endometrial cancer, and endometriosis: An assessment of the biological and epidemiological evidence. Crit Rev Toxicol 25:463-531.
43. Adami HO, Lipworth L, Titusernstoff L, Hsieh CC, Hanberg A, Ahlborg U, Baron J, Trichopoulos D. 1995. Organochlorine compounds and estrogen-related cancers in women. Cancer Causes Control 6:551-566.
44. Safe S. 1995. Environmental and dietary estrogens and human health - Is there a problem? Environ Health Perspect 103:346-351.
45. Verdeal K, Ryan DS. 1979. Naturally-occurring estrogens in plant foodstuffs-A review. J Food Prot 42:577-583.
46. Kuhnau J. 1976. The flavonoids. A class of semi-essential food components: Their role in human nutrition. World Rev Nutr Diet 24:117-191.
47. Herrmann K. 1976. Flavonols and fiavones in food plants: A review. J Food Technol 11:433-448.
48. Adlercreutz H. 1995. Phytoestrogens: Epidemiology and a possible role in cancer protection. Environ Health Perspect 103:103-112.
49. Stitch SR, Toumba JK, Groen MB, Funke CW, Leemhuis J, Vink J, Woods GF. 1980. Excretion, isolation and structure of a new phenolic constituent of female urine. Nature 287:738-740.
50. Axelson M, Kirk DN, Farrant RD, Cooley G, Lawson AM, Setchell KDR. 1982. The identification of the weak oestrogen equol [7-hydroxy-3-(4′-hydroxyphenyl)chroman] in human urine. Biochem J 201:353-357.
51. Adlercreutz H, Fotsis T, Bannwart C, Wähälä K, Mäkelä T, Brunow G, Hase T. 1986. Determination of urinary lignans and phytoestrogen metabolites, potential antiestrogens and anticarcinogens in urine of women on various habitual diets. J Steroid Biochem 25:791-797.
52. Setchell KDR, Adlercreutz H. 1988. Mammalian lignans and phytooestrogens: Recent studies on their formation, metabolism and biological role in health and disease. In Rowland I, ed, Role of the Gut Flora in Toxicity and Cancer. Academic, London, UK, pp 315-345.
53. Lerner LJ, Turkheimer AR, Borman A. 1963. Phloretin, a weak estrogen and estrogen antagonist. Proc Soc Exp Biol Med 114:115-117.
54. Farmakalidis E, Hathcock JN, Murphy PA. 1985. Oestrogenic potency of genistein and daidzin in mice. Food Chem Toxicol 23:741-745.
55. Jordan VC, Mittal S, Gosden B, Koch R, Lieberman ME. 1985. Structure-activity relationships of estrogens. Environ Health Perspect 61:91-110.
56. Miksicek RJ. 1993. Commonly occurring plant flavonoids have estrogenic activity. Mol Endocrinol 44:37-43.
57. Sathyamoorthy N, Wang TTY, Phang JM. 1994. Stimulation of pS2 expression by diet-derived compounds. Cancer Res 54:957-961.
58. Medlock KL, Branham WS, Sheehan DM. 1995. The effects of phytoestrogens on neonatal rat uterine growth and development. Proc Soc Exp Biol Med 208:307-313.
59. Scarlata S, Miksicek R. 1995. Binding properties of coumestrol to expressed human estrogen receptor. Mol Cell Endocrinol 115:65-72.
60. Markaverich BM, Roberts RR, Alejandro MA, Johnson GA, Middleditch BS, Clark JH. 1988. Bioflavonoid interaction with rat uterine type II binding sites and cell growth inhibition. J Steroid Biochem 30:71-78.
61. Markaverich BM, Webb B, Densmore CL, Gregory RR. 1995. Effects of coumestrol on estrogen receptor function and uterine growth in ovariectomized rats. Environ Health Perspect 103:574-581.
62. Mäkelä SI, Davis VL, Tally WC, Korkman J, Salo L, Vihko R, Santti R, Korach KS. 1994. Dietary estrogens act through estrogen receptor-mediated processes and show no antiestrogenicity in cultured breast cancer cells. Environ Health Perspect 102:572-578.
63. Ruh MF, Zacharewski T, Connor K. Howell J, Chen I, Safe S. 1995. Naringenin: A weakly estrogenic bioflavonoid which exhibits antiestrogenic activity. Biochem Pharmacol 50:1485-1493.
64. Setchell KDR, Lawson AM, Mitchell FL, Adlercreutz H, Kirk DN, Axelson M. 1980. Lignans in man and in animal species. Nature 287:740-742.
65. Setchell KDR, et al. 1981. Lignan formation in man - Microbial involvement and possible roles in relation to cancer. Lancet 2:4-7.
66. Bannwart C, Adlercreutz H, Wähälä K, Brunow G, Hase T. 1989. Detection and identification of the plant lignans lariciresinol, isolariciresinol and secoisolariciresinol in human urine. Clin Chim Acta 180:293-301.
67. Mirocha CJ, Christensen CM. 1974. Oestrogenic mycotoxins synthesized by Fusarium. In Purchase IFH, ed, Mycotoxins. Elsevier, Amsterdam, The Netherlands, pp 129-148.
68. Kiang DT, Kennedy BJ, Pathre SV, Mirocha CJ. 1978. Binding characteristics of zearalenone analogs to estrogen receptors. Cancer Res 38:3611-3615.
69. Mellanen P, et al. 1996. Wood-derived estrogens: Studies in vitro with breast cancer cell lines and in vivo in trout. Toxicol Appl Pharmacol 136:381-388.
70. Zacharewski T, Berhane K, Gillesby B. 1995. Detection of estrogen- and dioxin-like activity in pulp and paper mill black liquor effluent using in vitro recombinant receptor/reporter gene assays. Environ Sci Technol 29:2140-2146.
71. McMaster ME, Van der Kraak GJ, Munkittrick KR. 1995. Exposure to bleached kraft pulp mill effluent reduces the steroid biosynthetic capacity of white sucker ovarian follicles. Comp Biochem Physiol C 112:169-178.
72. Munkittrick KR, McMaster ME, Portt CB, Van der Kraak GJ, Smith IR, Dixon DG. 1992. Changes in maturity, plasma sex steroid levels, hepatic mixed-function oxygenase activity, and the presence of external lesions in lake whitefish (Coregonus culpeaformis) exposed to bleached kraft mill effluent. Can J Fish Aquat Sci 49:1560-1569.
73. Van der Kraak GJ, Munkittrick KR, McMaster ME, Portt CB, Chang JP. 1992. Exposure to bleached kraft pulp mill effluent disrupts the pituitary-gonadal axis of white sucker at multiple sites. Toxicol Appl Pharmacol 115:224-233.
74. Mäkelä SI, Pylkkanen LH, Santti RS, Adlercreutz H. 1995. Dietary soybean may be antiestrogenic in male mice. J Nutr 125:437-445.
75. Mousavi Y, Adlercreutz H. 1992. Enterolactone and estradiol inhibit each other's proliferative effect on MCF-7 breast cancer cells in culture. J Steroid Biochem Mol Biol 41:615-617.
76. Soto AM, Lin T, Justicia H, Silvia RM, Sonnenschein C. 1992. An "in culture" bioaassay to assess the estrogenicity of xenobiotics (E-screen). In Colburn T, Clement C, eds, Chemically Induced Alterations in Sexual and Functional Development: The Wildlife/Human Connection. Princeton Scientific, Princeton, NJ, USA, pp 295-309.
77. Krishnan AV, Stathis P, Permuth SF, Tokes L, Feldman D. 1993. Bisphenol-A: An estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 132:2279-2286.
78. Soto AM, Chung KL, Sonnenschein C. 1994. The pesticides endosulfan, toxaphene, and dieldrin have estrogenic effects on human estrogen-sensitive cells. Environ Health Perspect 102:380-383.
79. Jobling S, Reynolds T, White R, Parker MG, Sumpter JP. 1995. A variety of environmentally persistent chemicals, including some phthalate plasticizers, are weakly estrogenic. Environ Health Perspect 103:582-587.
80. Vom Saal FS, Nagel SC, Palanza P, Boechler M, Parmigiani S, Welshons WV. 1995. Estrogenic pesticides: Binding relative to estradiol in MCF-7 cells and effects of exposure during fetal life on subsequent territorial behaviour in male mice. Toxicol Lett 77:343-350.
81. Katzenellenbogen JA. 1995. The structural pervasiveness of estrogenic activity. Environ Health Perspect 103:99-101.
82. Forster MS, Wilder EL, Heinrichs WL. 1975. Estrogenic behavior of 2(o-chlorophenyl)-2-(p-chlorophenyl)-1,1,1 -trichloroethane and its homologues. Biochem Pharmacol 24:1777-1780.
83. Stancel GM, Ireland JS, Mukku VR, Robison AK. 1980. The estrogenic activity of DDT: In vivo and in vitro induction of a specific estrogen inducible uterine protein by o,p′-DDT. Life Sci 27:1111-1117.
84. Kupfer D, Bulger WH. 1977. Interaction of o,p′-DDT with the estrogen-binding protein (EBP) in human mammary and uterine tumors. Res Commun Chem Pathol Pharmacol 16:451-462.
85. Soto AM, Sonnenschein C, Chung KL, Fernandez MF, Olea N, Serrano FO. 1995. The E-screen assay as a tool to identify estrogens - An update on estrogenic environmental pollutants. Environ Health Perspect 103:113-122.
86. Shelby MD, Newbold RR, Tully DB, Chae K, Davis VL. 1996. Assessing environmental chemicals for estrogenicity using a combination of in vitro and in vivo assays. Environ Health Perspect 104:1296-1300.
87. Welch RM, Levin W, Conney AH. 1969. Estrogenic action of DDT and its analogs. Toxicol Appl Pharmacol 14:358-367.
88. Clement JG, Okey AB. 1972. Estrogenic and anti-estrogenic effects of DDT administered in the diet to immature female rats. Can J Physiol Pharmacol 50:971-975.
89. Robison AK, Schmidt WA, Stancel GM. 1985. Estrogenic activity of DDT: Estrogen-receptor profiles and the responses of individual uterine cell types following o,p′-DDT administration. J Toxicol Environ Health 16:493-508.
90. Singhal RL, Valadares JRE, Schwark WS. 1970. Metabolic control mechanisms in mammalian systems IX: Estrogen-like stimulation of uterine enzymes by o,p′-1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane. Biochem Pharmacol 19:2145-2155.
91. Duby RT, Travis HF, Terrill CE. 1971. Uterotropic activity of DDT in rats and mink and its influence on reproduction in the rat. Toxicol Appl Pharmacol 18:348-355.
92. Heinrichs WL, Gellert RJ, Bakke JL, Lawrence NL. 1971. DDT administered to neonatal rats induces persistent estrus syndrome. Science 173:642-643.
93. U.S. Environmental Protection Agency. 1988. Reviews of Environmental Contamination and Toxicology. Springer-Verlag, New York, NY.
94. Bulger WH, Muccitelli RM, Kupfer D. 1978. Studies on the in vivo and in vitro estrogenic activities of methoxychlor and its metabolites: Role of hepatic mono-oxygenase in methoxychlor activation. Biochem Pharmacol 27:2417-2423.
95. Bulger WH, Kupfer D. 1983. Estrogenic action of DDT analogs. Am J Ind Med 4:163-173.
96. Cummings AM, Gray LE Jr. 1989. Antifertility effect of methoxychlor in female rats: Dose- and time-dependent blockade of pregnancy. Toxicol Appl Pharmacol 97:454-462.
97. Gray LE Jr, et al. 1989. A dose-response analysis of methoxychlor-induced alterations of reproductive development and function in the rat. Fundam Appl Toxicol 12:92-108.
98. Cummings AM, Gray LE Jr. 1987. Methoxychlor affects the decidual cell response of the uterus but not other progestational parameters in female rats. Toxicol Appl Pharmacol 90:330-336.
99. Lione A. 1988. Polychlorinated biphenyls and reproduction. Reprod Toxicol 2:83-89.
100. Safe S. 1989. Polyhalogenated aromatics: Uptake, disposition and metabolism. In Kimbrough RD, Jensen AA, eds, Halogenated Biphenyls, Naphthalene, Dibenzodioxins and Related Compounds. Elsevier-North Holland, Amsterdam, The Netherlands, pp 51-69.
101. Korach KS, Sarver P, Chae K, McLachlan JA, McKinney JD. 1988. Estrogen receptor-binding activity of polychlorinated hydroxybiphenyls: Conformationully restricted structural probes. Mol Pharmacol 33:120-126.
102. Bergman Å, Klasson-Wehler E, Kuroki H. 1994. Selective retention of hydroxylated PCB metabolites in blood. Environ Health Perspect 102:464-469.
103. Moore M, Mustain M, Daniel K, Safe S, Zacharewski T, Gillesby B, Joyeux A, Balaguer P. 1997. Antiestrogenicity activity of hydroxylated PCBs identified in human serum. Toxicol Appl Pharmacol 142:160-168.
104. Arnold SF, Klotz DM, Collins BM, Vonier PM, Guillette LJ Jr, McLachlan JA. 1996. Synergistic activation of estrogen receptor with combinations of environmental chemicals. Science 272:1489-1492.
105. McLachlan JA. 1997. Synergistic effect of environmental estrogens - Report withdrawn. Science 227:462-463.
106. Ekelund R, Bergman A, Granmo A, Berggren M. 1990. Bioaccumulation of 4-nonylphenol in marine animals - A re-evaluation. Environ Pollut 64:107-120.
107. Naylor CG, Mieure JP, Adams WJ, Weeks JA, Castaidi FJ, Ogle LD, Romano RR. 1992. Alkylphenol ethoxylates in the environment. J Am Oil Chem Soc 69:695-703.
108. Soto AM, Justicia H, Wray JW, Sonnenschein C. 1991. p-Nonylphenol: An estrogenic xenobiotic released from "modified" polystyrene. Environ Health Perspect 92:167-173.
109. White R, Jobling S, Hoare SA, Sumpter JP, Parker MG. 1994. Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135:175-182.
110. Ren LF, Marquardt MA, Lech JJ. 1997. Estrogenic effects of nonylphenol on pS2, ER and MUC1 gene expression in human breast cancer cells-MCF-7. Chem-Biol Interact 104:55-64.
111. Lee PC, Lee W. 1996. In vivo estrogenic action of nonylphenol in immature female rats. Bull Environ Contam Toxicol 57:341-348.
112. Odum J, Lefevre PA, Tittensor S, Paton D, Routledge EJ, Beresford NA, Sumpter JP, Ashby J. 1997. The rodent uterotrophic assay - Critical protocol features, studies with nonylphenols, and comparison with a yeast estrogenicity assay. Regul Toxicol Pharmacol 25:176-188.
113. Brotons JA, Olea-Serrano MF, Villalobos M, Pedraza V, Olea N. 1995. Xenoestrogens released from lacquer coatings in food cans. Environ Health Perspect 103:608-612.
114. Olea N, et al. 1996. Estrogenicity of resin-based composites and sealants used in dentistry. Environ Health Perspect 104:298-305.
115. Villalobos M, Olea N, Bretons JA, Oleaserrano MF, Dealmodovar JMR, Pedraza V. 1995. The E-screen assay - A comparison of different MCF-7 cell stocks. Environ Health Perspect 103:844-850.
116. McDonnell DP, Clemm DL, Hermann T, Goldman ME, Pike JW. 1995. Analysis of estrogen receptor function in vitro reveals three distinct classes of antiestrogens. Mol Endocrinol 9:659-669.
117. Katzenellenbogen JA, O'Malley BW, Katzenellenbogen BS. 1996. Tripartite steroid hormone receptor pharmacology - interaction with multiple effector sites as a basis for the cell- and promoter-specific action of these hormones. Mol Endocrinol 10:119-131.