Hormonal action of plant derived and anthropogenic non-steroidal estrogenic compounds: Phytoestrogens and xenoestrogens

Current Medicinal Chemistry

Volumn 17, Issue 30, 2010, Pages 3542-3574

  Lorand T ^a   Vigh, E ^a   Garai, J ^a  

^a UNIVERSITY OF PÉCS   (Hungary)

Author keywords

Endocrine disruptors; Estrogen receptors; Persistent organic pollutants; Phytoestrogen; Polyphenols; Serm; Xenoestrogen

Indexed keywords

ALKYLPHENOL; CHALCONE DERIVATIVE; CHLORDECONE; CHLORPHENOTANE; DIOXIN; ENVIRONMENTAL CHEMICAL; ESTROGEN DERIVATIVE; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FLAVONOID; GINSENOSIDE; ISOFLAVONOID; LIGNAN DERIVATIVE; METHOXYCHLOR; PHENOL DERIVATIVE; PHYTOESTROGEN; POLYCHLORINATED BIPHENYL DERIVATIVE; SAPONIN DERIVATIVE; SELECTIVE ESTROGEN RECEPTOR MODULATOR; STILBENE DERIVATIVE; UNCLASSIFIED DRUG; XENOESTROGEN;

ADIPOSE TISSUE; ARTICLE; ESTROGEN ACTIVITY; ESTROGEN METABOLISM; HORMONE STRUCTURE; HUMAN; NONHUMAN; POLLUTION;

EID: 77957958535     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986710792927813     Document Type: Article

References (284)

1. Bennets, 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.
2. IPCS Report. Global assessment of the state-of-the-science of endocrine disruptors. (Damstra, T.; Barlow, s.; Bergman, A.; Kavlock, R.; Van Der Kraak, G., Eds.), IPCS/WHO: Geneva, Switzerland, 2002. (http://whqlibdoc.who.int/hq/2002/WHO_PCS_EDC_ 02.2.pdf)
3. Diamanti-Kandarakis, E.; Bourguignon, J.P.; Giudice, L.C.; Hauser, R.; Prins, G.S.; Soto, A.M.; Zoeller, R.T.; Gore, A.C. Endocrine-disrupting chemicals: an Endocrine Society scientific statement. Endocr. Rev., 2009, 30, 293-342.
4. Adams, N.R. Detection of the effects of phytoestrogens on sheep and cattle. J. Anim. Sci., 1995, 73, 1509-15.
5. Drane, H.M.; Wrathall, A.E.; Patterson, D.S.P.; Hebert, C.N. Possible oestrogenic effects of feeding soyameal to prepubertal gilts. Br. Vet. J., 1981, 137, 283-88.
6. Wright, P.A. Infertility in rabbits induced by feeding ladino clover. Proc. Roy Soc. Exp. Biol. Med., 1960, 105, 428-30.
7. Watanabe, S.; Yamaguchi, M.; Soube, T.; Takahashi, T.; Miura, T.; Arai, Y.; Mazur, W.; Wähälä, K.; Adlercreutz, H. Pharmacokinetics of soybean isoflavones in plasma, urine and feces of men after ingestion of 60g baked soybean powder (Kinako). J. Nutr., 1998, 128, 1710-5.
8. Manach, C.; Donovan, J.L. Pharmacokinetics and metabolism of dietary flavonoids in humans. Free Radic. Res., 2004, 38, 771-85.
9. Zhang, Y.; Wang, G.J.; Song, T.T.; Murphy, P.A.; Hendrich, S. Urinary disposition of the soybean isoflavones daidzein, genistein and glycitein among humans with moderate fecal isoflavone degradation activity. J. Nutr., 1999, 129, 957-62.
10. Coffey, D.S. Similarities of prostate and breast cancer: Evolution, diet, and estrogens. Urology, 2001, 57, suppl. 4a, 31-38.
11. Ramos, S. Effects of dietary flavonoids on apoptotic pathways related to cancer chemoprevention. J. Nutr. Biochem., 2007, 18, 427-42.
12. Siow, R.C.M.; Li, F.Y.L.; Rowlands, D.J.; deWinter, P.; Mann, G.E. Cardiovascular targets for estrogens and phytoestrogens: Transcriptional regulation of nitric oxide synthase and antioxidant defense genes. Free Radic. Biol. Med., 2007, 42, 909-25.
13. Turner, J.V.; Agatonovic-Kustrin, S.; Glass, B.D. Molecular aspects of phytoestrogen selective binding at estrogen receptors. J. Pharm. Sci., 2007, 96, 1879-85.
14. Medjakovic, S.; Jungbauer, A. Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor. J. Steroid Biochem. Molec. Biol., 2008, 108, 171-7.
15. Watson, C.S.; Bulayeva, N.N.; Wozniak, A.L.; Finnerty, C.C. Signaling from the membrane via membrane estrogen receptor-alpha: Estrogens, xenoestrogens, and phytoestrogens. Steroids, 2005, 70, 364-71.
16. Watson, C.S.; Alyea, R.A.; Jeng, Y.J.; Kochukov, M.Y. Nongenomic actions of low concentration estrogens and xenoestrogens on multiple tissues. Mol. Cell Endocrinol., 2007, 274, 1-7.
17. Belcher, S.M.; Zsarnovszky, A. Estrogenic actions in the brain: estrogen, phytoestrogens, and rapid intracellular signaling mechanisms. J. Pharm. Exp. Ther., 2001, 299, 408-41
18. Krazeisen, A.; Breitling, R.; Moller, G.; Adamski, J. Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5. Mol. Cell Endocrinol., 2001, 171, 151-62.
19. Lu, L.J.; Cree, M.; Josyula, S.; Nagamani, M.; Grady, J.J.; Anderson, K.E. Increased urinary excretion of 2-hydroxyestrone but not 16alpha-hydroxyestrone in premenopausal women during a soya diet containing isoflavones. Cancer Res., 2000, 60, 1299-305.
20. Pietta P.G. Flavonoids as antioxidants. J. Nat. Prod., 2000, 63, 1035-42.
21. Castillo, C.; Salazar, V.; Ariznavarreta, C.; Vara, E.; Tresguerres, J.A.F. Effect of isoflavone administration on age-related hepatocyte changes in old ovariectomized femal Wistar rats. Phytomedicine, 2006, 13, 468-76.
22. Prokai, L.; Prokai-Tatrai, K.; Perjesi, P.; Zharikova, A.D.; Perez, E.J.; Liu, R.; Simpkins, J.W. Quinol-based cyclic antioxidant mechanisms in estrogen neuroprotection. Proc. Natl. Acad. Sci. USA, 2003, 100, 11741-6.
23. Prokai-Tatrai, K.; Perjesi, P.; Rivera-Portalatin, N.M.; Simpkins, J.W.; Prokai, L. Mechanistic investigations on the antioxidant action of a neuroprotective estrogen derivative. Steroids, 2008, 73, 280-8.
24. Bradbury, R.B.; White, D.E. In Vitamins and Hormones; Harris, Marian and Thimann, Ed.; Academic Press: New York, 1954, Vol. 12, pp. 207-230.
25. Mazur, W.M.; Duke, J.A.; Wahala, K.; Rasku, S.; Adlercreutz, H. Isoflavonoids and lignans in legumes: Nutritional and health aspects in humans. J. Nutr. Biochem., 1998, 9, 193-200.
26. Cheng, E.; Story, C.D.; Yoder, L.; Hale, W.H.; Burroghs, W. Estrogenic activity of isoflavone derivatives extracted and prepared from soybean oil meal. Science, 1953, 118, 16 4-5.
27. Carter, M.W.; Smart, W.W.G. Jr.; Matrone, G. Estimation of estro-genic activity of genistein obtained from soybean meal. Proc. Soc. Exp. Biol. Med., 1953, 84, 506-7.
28. Dean, P.D.G.; Exley, D.; Goodwin, T.W. Steroid oestrogens in plants: re-estimation of oestrone in pomegranate seeds. Phytochem., 1971, 10, 2215-6.
29. Price, K.R.; Fenwick, G.R. Naturally occurring oestrogens in foods A review. Food Addit. Contam., 1985, 2, 73-106.
30. Lieberman, S. Are the differences between estradiol and other estrogens merely semantical? J. Clin. Endocrinol. Metab., 1996, 81, 850-1.
31. Hughes, C. Are the differences between estradiol and other estrogens merely semantical? J. Clin. Endocrinol. Metab., 1996, 81, 2405.
32. Ise, R.; Han, D.; Takahashi, Y.; Terasaka, S.; Inoue, A.; Tanji, M.; Kiyama, R. Expression profiling of the estrogen responsive genes in response to phytoestrogens using a customized DNA microarray. FEBS Lett., 2005, 579, 1732-40.
33. Naciff, J.M.; Jump, M.L.; Torontali, S.M.; Carr, G.J.; Tiesman, J.P.; Overmann, G.J; Daston, G.P. Gene expression profile induced by 17alpha-ethynyl estradiol, bisphenol A, and genistein in the developing female reproductive system of the rat. Toxicol. Sci., 2002, 68, 184-99.
34. Hwang, C.H.; Kwak, H.S.; Lim, H.J.; Lee, S.H.; Kang, Y.S.; Choe, T.B.; Hur, H.G.; Han, K.O. Isoflavone metabolites and their in vitro dual functions:They can act as an estrogenic agonist or antagonist depending on the estrogen concentration. J. Steroid Biochem. Mol. Biol., 2006, 101, 246-53.
35. Bowers, J.L.; Tyulmenkov, V.V.; Jernigan, S.C.; Klinge, C.M. Resveratrol acts as a mixed agonist/antagonist for estrogen receptors and. Endocrinology., 2000, 141, 3657-67.
36. Jordan, V.C. Selective estrogen receptor modulation: a personal perspective. Cancer Res., 2001, 61, 5683-7.
37. Brzezinski, A.; Debi, A. Phytoestrogens: the "natural" selective estrogen receptor modulators? Eur. J. Obstet. Gynecol. Reprod. Biol., 1999, 85, 47-51.
38. Dai, S.Y.; Burris, T.P.; Dodge, J.A.; Montrose-Rafizadeh, C.; Wang, Y.; Pascal, B.D.; Chalmers, M.J.; Griffin, P.R. Unique ligand binding patterns between estrogen receptor alpha and beta revealed by hydrogen-deuterium exchange. Biochemistry, 2009, 48, 9668-76.
39. Harborne, J.B. The Flavonoids. (Advances in research since 1980), Chapman and Hall Ltd.: London, 1988.
40. Ayres, D.C.; Loike, J.D. Lignans: Chemical, biological and clinical properties, Cambridge University Press: Cambridge, 1990.
41. Green, S.; Walter, P.; Kumar, V.; Krust, A.; Bornert, J.M.; Argos, P.; Chambon, P. Human oestrogen receptor cDNA: sequence, expression and homology to v-erb-A. Nature, 1986, 320, 134-9.
42. Greene, G.L.; Gilna, P.; Waterfield, M.; Baker, A.; Hort, Y.; Shine, J. Sequence and expression of human estrogen receptor complementary DNA. Science, 1986, 231, 1150-4.
43. Kuiper, G.G.J.M.; Enmark, E.; Pelto-Huikko, M.; Nilsson, S.; Gustafsson, J.Å. Cloning of a novel estrogen receptor expressed in rat prostate and ovary. Proc. Natl. Acad. Sci. USA, 1996, 93, 59255930.
44. Brzozowski, A.M.; Pike, A.C.; Dauter, Z.; Hubbard, R.E.; Bonn, T.; Engstrom, O.; Ohman, L.; Greene, G.L.; Gustafsson, J.A.; Carlquist, M. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature, 1997, 389, 753-758.
45. Pike, A.C.; Brzozowski, A.M.; Hubbard, R.E.; Bonn, T.; Thorsell, A.G.; Engstrom, O.; Ljunggren, J.; Gustafsson, J.A., Carlquist, M. Structure of the ligand-binding domain of oestrogen receptor in the presence of a partial agonist and a full antagonist. EMBO J., 1999, 18, 4608-18.
46. Baker, M.E.; Chang, D.J.; Chandsawangbhuwana, C. 3D model of lamprey estrogen receptor with estradiol and 15 -hydroxyestradiol. PLoS ONE, 2009, 4, e6038.
47. Thornton, J.W. Evolution of vertebrate steroid receptors from an ancestral estrogen receptor by ligand exploitation and serial genome expansions. Proc. Natl. Acad. Sci. USA, 2001, 98, 5671-6.
48. McKenna, N.J.; O'Malley, B.W. Combinatorial control of gene expression by nuclear receptors and coregulators. Cell, 2002, 108, 465-74.
49. Katzenellenbogen, J.A.; Muthyala, R.; Katzenellenbogen, B.S. Nature of the ligand-binding pocket of estrogen receptor and the search for subtype-selective ligands and implications for the prediction of estrogenic activity. Pure Appl. Chem., 2003, 75, 2397-403.
50. Harris, H.A.; Bapat, A.R.; Gonder, D.S.; Frail, D.E. The ligand binding profiles of estrogen receptors and are species dependent. Steroids, 2002, 67, 379-84.
51. Nettles, K.W.; Bruning, J.B.; Gil, G.; O'Neill, E.E.; Nowak, J.; Guo, Y.; Kim, Y.; DeSombre, E.R.; Dilis, R.; Hanson, R.N.; Joachimiak, A.; Greene, G.L. Structural plasticity in the oestrogen receptor ligand-binding domain. EMBO Rep., 2007, 8, 563-8.
52. Xu, W.; Powell, E. Intermolecular interactions identify ligandselective activity of estrogen receptor/dimmers. Proc. Natl. Acad. Sci. USA, 2008, 105, 19012-7.
53. Krege, J.H.; Hodgin, J.B.; Couse, J.F.; Enmark, E.; Warner, M.; Mahler, J.F.; Sari, M.; Korach, K.S.; Gustafsson, J.Å.; Smithies, O. Generation and reproductive phenotypes of mice lacking estrogen receptor. Proc. Natl. Acad. Sci. USA, 1998, 95, 15677-82.
54. Korach, K.S.; Emmen, J.M.; Walker, V.R.; Hewitt, S.C.; Yates, M.; Hall, J.M.; Swope, D.L.; Harrell, J.C.; Couse, J.F. Update on animal models developed for analyses of estrogen receptor biological activity. J. Steroid Biochem. Mol. Biol., 2003, 86, 387-91.
55. Koehler, K.F.; Helguero, L.A.; Haldosén, L.A.; Warner, M.; Gustafsson, J.Å. Reflections on the discovery and significance of estrogen receptor. Endocr. Rev., 2005, 26, 465-78.
56. Harris, H.A. Estrogen receptor-: Recent lessons from in vivo studies. Mol. Endocrinol., 2007, 21, 1-13.
57. Weihua, Z.; Saji, S.; Makinen, S.; Cheng, G.; Jensen, E.V.; Warner, M.; Gustafsson, J.Å. Estrogen receptor (ER), a modulator of ERin the uterus. Proc. Natl. Acad. Sci. USA, 2000, 97, 5936-41.
58. Matthews, J.; Gustafsson, J.Å. Estrogen signaling: a subtle balance between ER alpha and ER beta. Mol. Interv., 2003, 3, 281-92.
59. Kuiper, G.G.; Lemmen, J.G.; Carlsson, B.; Corton, J.C.; Safe, S.H.; van der Saag, P.T.; van der Burg, B.; Gustafsson, J.Å. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology, 1998, 139, 4252-63.
60. Kuiper, G.G.; Carlsson, B.; Grandien, K.; Enmark, E.; Haggblad, J.; Nilsson, S.; Gustafsson, J.Å. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors and. Endocrinology, 1997, 138, 863-70.
61. Imamov, O.; Shim, G.J.; Warner, M.; Gustafsson, J.Å. Estrogen receptor beta in health and disease. Biol. Reprod., 2005, 73, 86671.
62. Pearce, S.T.; Jordan, V.C. The biological role of estrogen receptors and in cancer. Crit. Rev. Oncol. Hematol., 2004, 50, 3-22.
63. Currie, L.J.; Harrison, M.B.; Trugman, J.M.; Bennett, J.P.; Wooten, G.F. Postmenopausal estrogen use affects risk for Parkinson disease. Arch. Neurol., 2004, 61, 886-8.
64. Emmerson, E.; Campbell, L.; Ashcroft, G.S.; Hardman, M.J. Unique and synergistic roles for 17beta-estradiol and macrophage migration inhibitory factor during cutaneous wound closure are cell type specific. Endocrinology, 2009, 150, 2749-57.
65. Mäkelä, S.; Savolainen, H.; Aavik, E.; Myllärniemy, M.; Strauss, L.; Taskinen, E.; Gustafsson, J.Å.; Häyry, P. Differentation between vasculoprotective and uterotrophic effects of ligands with different binding affinities to estrogen receptors and. Proc. Natl. Acad. Sci. USA, 1999, 96, 7077-82.
66. Tsuchiya, M.; Miura, T.; Hanaoka, T.; Iwasaki, M.; Sasaki, H. Tanaka, T.; Nakao, H.; Katoh, T.; Ikenoue, T.; Kabuto, M.; Tsugane, S. Effect of soy isoflavones on endometriosis: interaction with estrogen receptor 2 gene polymorphism. Epidemiology, 2007, 18, 402-8.
67. Jeng, Y.J.; Kochukov, M.Y.; Watson, C.S. Membrane estrogen receptor--mediated nongenomic actions of phytoestrogens in GH3/B6/F10 pituitary tumor cells. J. Mol. Signal., 2009, 4, 2.
68. Mazur, W.M.; Adlercreutz, H. Naturally occurring estrogens in food. Pure Appl. Chem., 1998, 70, 1759-76.
69. Mazur, W.M.; Wahala, K.; Rasku, S.; Salakka, A.; Hase, T.; Adlercreutz, H. Lignan and isoflavonoid concentrations in tea and coffee. Br. J. Nutr., 1998, 79, 37-45.
70. Adlercreutz, H.; Mazur, W. Phyto-oestrogens and Western diseases. Ann. Med., 1997, 29, 95-120.
71. Reinli, K.; Block, G. Phytoestrogen content of foods-a compendium of literature values. Nutr. Cancer, 1996, 26, 123-48.
72. Hwang, J.; Sevanian, A.; Hodis, H.N.; Ursini, F. Synergistic inhibition of LDL oxidation by phytoestrogens and ascorbic acid. Free Radic. Biol. Med., 2000, 29, 79-89.
73. Ambra, R.; Rimbach, G.; de Pascual Teresa, S.; Fuchs, D.; Wenzel, U.; Daniel, H.; Virgili, F. Genistein affects the expression of genes involved in blood pressure regulation and angiogenesis in primary human endothelial cells. Nutr. Metab. Cardiovasc. Dis., 2006, 16, 35-43.
74. Peterson, G. Evaluation of the biochemical targets of genistein in tumor cells. J. Nutr., 1995, 125, S784-9.
75. Mazur, W.; Adlercreutz, H. Overview of naturally occurring endocrine-active substances in the human diet in relation to human health. Nutrition, 2000, 16, 654-8.
76. Hughes, C.L.Jr. Phytochemical mimicry of reproductive hormones and modulation of herbivore fertility by phytoestrogens. Envir. Health Perspec., 1998, 78, 171-5.
77. Russell, G.B.; Singh, P.; Fenemore, P.G. Insect-control chemicals from plants. III. Toxic lignans from Libocedrus bidwillii. Aust. J. Biol. Sci., 1976, 29, 99-103.
78. Shimada, N.; Akashi, T.; Aoki, T.; Ayabe, S. Induction of isoflavonoid pathway in the model legume Lotus japonicus: molecular characterization of enzymes involved in phytoalexin biosynthesis. Plant Sci., 2000, 160, 37-47.
79. Mathesius, U. Flavonoids induced in cells undergoing nodule organogenesis in white clover are regulators of auxin breakdown by peroxidase. J. Exp. Bot., 2001, 52, 419-26.
80. Peck, M.C.; Fisher, R.F.; Long, S.R. Diverse flavonoids stimulate NodD1 binding to nod gene promoters in Sinorhizobium meliloti. J. Bacteriol., 2006, 188, 5417-27.
81. Baker, M.E. Human placental 17 -hydroxysteroid dehydrogenase is homologous to NodG protein of Rhizobium meliloti. Mol. Endo crinol., 1989, 3, 881-4.
82. Györgypal, Z.; Kondorosi, A. Homology of the ligand-binding regions of Rhizobium symbiotic regulatory protein NodD and vertebrate nuclear receptors. Mol. Gen. Genet., 1991, 226, 337-40.
83. Baker, M.E. Evolution of regulation of steroid-mediated intercellular communication in vertebrates: insights from flavonoids, signals, that mediate plant-rhizobia symbiosis. J. Steroid Biochem. Molec. Biol., 1992, 41, 301-8.
84. Cheng, W.Y.; Kuo, Y.H.; Huang, C.J. Isolation and identification of novel estrogenic compounds in yam tuber (Dioscorea alata Cv. Tainung No. 2). J. Agric. Food Chem., 2007, 55, 7350-8.
85. Russell, L.; Hicks, G. S.; Low, A. K.; Shepherd, J. M.; Brown, C. A. Phytoestrogens: a viable option? Am. J. Med. Sci., 2002, 324, 185-88.
86. Fang, H.; Tong, W.; Shi, L.M.; Blair, R.; Perkins, R.; Branham, W.; Hass, B.S.; Xie, Q.; Dial, S.L.; Moland, C.L.; Sheehan, D.M. Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. Chem. Res. Toxicol., 2001, 14, 280-94.
87. Patlak, M. A testing deadline for endocrine disrupters. Envir. Sci. Technol., 1996, 30, 540A-4A.
88. Mersereau, J.E.; Levy, N.; Staub, R.E.; Baggett, S.; Zogric, T.; Chow, S.; Ricke, W.A.; Tagliaferri, M.; Cohen, I.; Bjeldanes, L.F.; Leitman, D.C. Liquiritigenin is a plant-derived highly selective estrogen receptor agonist. Mol. Cell Endocrinol., 2008, 283, 49-57.
89. Cvoro, A.; Paruthiyil, S.; Jones, J.O.; Tzagarakis-Foster, C.; Clegg, N.J.; Tatomer, D.; Medina, R.T.; Tagliaferri, M.; Schaufele, F.; Scanlan, T.S.; Diamond, M.I.; Cohen, I.; Leitman, D.C. Selective activation of estrogen receptor-beta transcriptional pathways by an herbal extract. Endocrinology, 2007, 148, 538-47.
90. Kupfer, R.; Swanson, L.; Chow, S.; Staub, R.E.; Zhang, Y.L.; Cohen, I.; Christians, U. Oxidative in vitro metabolism of liquiritigenin, a bioactive compound isolated from the Chinese herbal selective estrogen beta-receptor agonist MF101. Drug Metab. Dis pos., 2008, 36, 2261-9.
91. Maggiolini, M.; Statti, G.; Vivacqua, A.; Gabriele, S.; Rago, V.; Loizzo, M.; Menichini, F.; Amdo, S. Estrogenic and antiproliferative activities of isoliquiritigenin inMCF7 breast cancer cells. J. Steroid Biochem. Mol. Biol., 2002, 82, 315-22.
92. Han, D.H.; Denison, M.S.; Tachibana, H.; Yamada, K. Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. Biosci. Biotechnol. Biochem., 2002, 66, 1479-87.
93. Ciolino, H.P.; Wang, T.T.; Yeh, G.C. Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity. Cancer Res., 1998, 58, 2754-60.
94. Androutsopoulos, A.; Wilsher, N.; Arroo, R.R.J.; Potter, G.A.; Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450. Canc. Lett., 2009, 274, 54-60.
95. Whitman, S.C.; Kurowska, E.M.; Manthey, J.A.; Daugherty, A. Steroid activities comparison of natural and food wrap compounds in human breast cancer cell lines. Atherosclerosis, 2005, 178, 2532.
96. Markaverich, B.M.; Roberts, R.R.; Alejandro, M.A.; Johnson, G.A.; Middleditch, B.S.; Clark, J.H. Bioflavonoid interactions with rat uterine type II binding sites and cell growth inhibition. J. Steroid Biochem., 1988, 29, 71-8.
97. 3H]luteolin. Steroids, 2001, 66, 707-19.
98. Garai, J.; Adlercreutz, H. Estrogen-inducible uterine flavonoid binding sites: is it time to reconsider? J. Steroid Biochem. Mol. Biol., 2004, 88, 377-81.
99. Molnar, V.; Garai, J. Plant-derived anti-inflammatory compounds affect MIF tautomerase activity. Int. Immunopharmacol., 2005, 5, 849-56.
100. Oshima, S.; Onodera, S.; Amizuka, N.; Li, M.; Irie, K.; Watanabe, S.; Koyama, Y.; Nishihira, J.; Yasuda, K.; Minami, A. Macrophage migration inhibitory factor-deficient mice are resistant to ovariectomy-induced bone loss. FEBS Lett., 2006, 580, 1251-6.
101. Albertazzi, P.; Pansini, F.; Bonaccorsi, G.; Zanotti, L.; Forini, E.; De Aloysio, D. The effect of dietary soy supplementation on hot flushes. Obstet. Gynecol., 1998, 91, 6-11.
102. Cassidy, A.; Albertazzi, P.; Lise Nielsen, I.; Hall, W.; Williamson, G.; Tetens, I.; Atkins, S.; Cross, H.; Manios, Y.; Wolk, A.; Steiner, C.; Branca, F. Critical review of health effects of soyabean phytooestrogens in post-menopausal women. Proc. Nutr. Soc., 2006, 65, 76-92.
103. Marini, H.; Bitto, A.; Altavilla, D.; Burnett, B.P.; Polito, F.; Di Stefano, V.; Minutoli, L.; Atteritano, M.; Levy, R.M.; D'Anna, R.; Frisina, N.; Mazzaferro, S.; Cancellieri, F.; Cannata, M.L.; Corrado, F.; Frisina, A.; Adamo, V.; Lubrano, C.; Sansotta, C.; Marini, R.; Adamo, E.B.; Squadrito, F. Breast safety and efficacy of genistein aglycone for postmenopausal bone loss: A follow-up study. J. Clin. Endocrinol. Metab., 2008, 93, 4787-96.
104. Wang, H.J.; Murphy, P.A. Isoflavone content in commercial soybean foods. J. Agric. Food Chem., 1994, 42, 1666-73.
105. Wang, H.J.; Murphy, P.A. Isoflavone composition of American and Japanese soybeans in Iowa: effects of variety, crop year, and location. J. Agric. Food Chem., 1994, 42, 1674-7.
106. Wakai, K.; Egami, I.; Kato, K.; Kawamura, T.; Tamakoshi, A.; Lin, Y.; Nakayama, T.; Wada, M.; Ohno, Y. Dietary intake and sources of isoflavones among Japanese. Nut. Cancer, 1999, 33, 139-45.
107. de Kleijn, M.J.; van der Schouw, Y.T.; Wilson, P.W.; Adlercreutz, H.; Mazur, W.; Grobbee, D.E.; Jacques, P.F. Intake of dietary phytoestrogens is low in postmenopausal women in the United States: the Framingham study. J. Nutr., 2001, 131, 1826-32.
108. Xu, X.; Duncan, A.M.; Merz, B.E.; Kurzer, M.S. Effects of soy isoflavones on estrogen and phytoestrogen metabolism in premenopausal women. Cancer Epidemiol. Biomarkers Prev., 1998, 7, 1101-8.
109. Schuster, D.; Nashev, L.G.; Kirchmair, J.; Laggner, C.; Wolber, G.; Langer, T.; Odermatt, A. Discovery of non-steroidal 17betahydroxysteroid dehydrogenase 1 inhibitors by pharmacophorebased screening of virtual compound libraries. J. Med. Chem., 2008, 51, 4188-99.
110. Vihko, P.; Härkönen, P.; Soronen, P.; Törn, S.; Herrala, A.; Kurkela, R.; Pulkka, A.; Oduwole, O.; Isomaa, V. 17betahydroxysteroid dehydrogenases-their role in pathophysiology. Mol. Cell. Endocrinol., 2004, 215, 83-8.
111. Rice, S.; Mason, H.D.; Whitehead, S.A. Phytoestrogens and their low dose combinations inhibit mRNA expression and activity of aromatase in human granulosa-luteal cells J. Steroid Biochem. Mol. Biol., 2006, 101, 216-25.
112. Li, Y.; Ross-Viola, J.S.; Shay, N.F.; Moore, D.D.; Ricketts, M.L. Human CYP3A4 and murine Cyp3A11 are regulated by equol and genistein via the pregnane X receptor in a species-specific manner. J. Nutr., 2009, 139, 898-904.
113. Adlercreutz, H.; Markkanen, H.; Watanabe, S. Plasma concentrations of phyto-estrogens in Japanese men. Lancet, 1993, 342, 120910.
114. Pfitscher, A.; Reiter, E.; Jungbauer, A. Receptor binding and transactivation activities of red clover isoflavones and their metabolites. J. Steroid Biochem. Mol. Biol., 2008, 112, 87-94.
115. Setchell, K.D. Phytoestrogens: the biochemistry, physiology, and implications for human health of soy isoflavones. Am. J. Clin. Nutr. 1998, 68, 1333S-46S.
116. Setchell, K.D.; Cassidy, A. Dietary isoflavones: biological effects and relevance to human health. J. Nutr. 1999, 129, 758S-67S.
117. Bannwart, C.; Adlercreutz, H.; Fotsis, T.; Wähälä, K.; Hase, T.; Brunow, G. Identification of O-desmethylangolensin, a metabolite of daidzein, and of matairesinol, one likely plant precursor of the animal lignan enterolactone, in human urine. Fin. Chem. Lett., 1984, 4-5, 120-25.
118. Coldham, N.G.; Darby, C.; Hows, M.; King, L.J.; Zhang, A.Q.; Sauer, M.J. Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism. Xenobiotica, 2002, 32, 45-62.
119. Heinonen, S.; Wähälä, K., Adlercreutz, H.; Identification of isoflavone metabolites dihydrodaidzein, dihydrogenistein, 6'-OHO-dma, and cis-4-OH-equol in human urine by gas chromatography-mass spectroscopy using authentic reference compounds. Anal. Biochem., 1999, 274, 211-9.
120. Ibarreta, D.; Daxenberger, A.; Meyer, H.H.D. Possible health impact of phytoestrogens and xenoestrogens in food. APMIS, 2001, 109, 161-84.
121. Heinonen, S.M.; Wähälä, K.; Adlercreutz, H. Identification of urinary metabolites of the red clover isoflavones formononetin and biochanin A in human subjects. J. Agric. Food Chem., 2004, 52, 6802-09.
122. Morito, K.; Hirose, T.; Kinjo, J.; Hirakawa, T.; Okawa, M.; Nohara, T.; Ogawa, S.; Inoue, S.; Muramatsu, M.; Masamune, Y. Interaction of phytoestrogens with estrogen receptors alpha and beta. Biol. Pharm. Bull., 2001, 24, 351-6.
123. Le Bail, J.C.; Champavier, Y.; Chulia, A.J.; Habrioux, G. Effects of phytoestrogens on aromatase, 3 and 17 -hydroxysteroid dehydrogenase activities and human breast cancer cells. Life Sci., 2000, 66, 1281-91.
124. Burow, M.E.; Boué, S.M.; Collins-Burow, B.M.; Melnik, L.I.; Duong, B.N.; Carter-Wientjes, C.H.; Li, S.; Wiese, T.E.; Cleveland, T.E.; McLachlan, J.A. Phytochemical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor and. J. Endocrinol., 2001, 86, 1750-8.
125. Salvo, V.A.; Boué, S.M.; Fonseca, J.P.; Elliott, S.; Corbitt, C.; Collins-Burow, B.M.; Curiel, T.J.; Shih, B.Y.; Carter-Wientjes, C.; Wood, C.E.; Erhardt, P.; Beckman, B.; McLachlan, J.A.; Cleveland, T.E.; Burow, M.E. Antiestrogenic glyceollins suppress human breast and ovarian carcinoma tumorigenesis. Clin. Cancer Res., 2006, 12, 7159-64.
126. Wood, C.E.; Clarkson, T.B.; Appt, S.E.; Franke, A.A.; Boué, S.M.;; Burow, M.E.; McCoy, T.; Cline, J.M. Effects of soybean Glyceollins and estradiol on postmenopausal female monkeys. Nutr. Cancer, 2006, 56, 67-75.
127. Stevens, J.F.; Ivancic, M.; Hsu, V.L.; Deinzer, M.L. Prenylflavonoids from Humulus lupulus. Phytochemistry, 1997, 44, 1575-85.
128. Stevens, J.F.; Taylor, A.W.; Clawson, J.E.; Deinzer, M.L. Fate of xanthohumol and related prenylflavonoids from hops to beer. J. Agric. Food Chem., 1999, 47, 2421-8.
129. Delmulle, L.; Bellahcéne, A.; Dhooge, W.; Comhaire, F.; Roelens, F.; Huvaere, K.; Heyerick, A.; Castronovo, V.; De Keukeleire, D. Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines. Phytomedicine, 2006, 13, 732-4.
130. Yit, C.C.; Das, N.P. Cytotoxic effect of buteinon human colon adenocarcinoma cell proliferation. Cancer Lett., 1994, 82, 65-72.
131. De Vincenzo, R.; Scambia, G.; Benedetti Panici, P.; Ranelletti, F.O.; Bonanno, G.; Ercoli, A.; Delle Monache, F.; Ferrari, F.; Piantelli, M.; Mancuso, S. Effect of synthetic and naturally occurring chalcones on ovarian cancer cell growth:structural-activity relationships. Anticancer Drug Res., 1995, 10, 481-90.
132. Halabalaki, M.; Aligiannis, N.; Papoutsi, Z.; Mitakou, S.; Moutsatsou, P.; Sekeris, C.; Skaltsounis, A.L. Three new arylobenzofurans from Onobrychis ebenoides and evaluation of their binding affinity for the estrogen receptor. J. Nat. Prod., 2000, 63, 1672-74.
133. Katsanou, E.S.; Halabalaki, M.; Aligiannis, N.; Mitakou, S.; Skaltsounis, A-L.; Alexi, X.; Pratsinis, H.; Alexis, M.N. Cytotoxic effects of 2-arylbenzofuran phytoestrogens on human cancer cells: Modulation by adrenal and gonadal steroids. J. Steroid Biochem. Mol. Biol., 2007, 104, 228-36.
134. Markaverich, B.; Mani, S.; Alejandro, M.A.; Markaverich, M.D.; Brown, T.; Velez-Trippe, C.; Murchison, C.; O'Malley, B.; Faith, R. A novel endocrine-disrupting agent in corn with mitogenic activity in human breast and prostatic cancer cells. Environ. Health Perspect., 2002, 110, 169-77.
135. Mani, S.K.; Reyna, A.M.; Alejandro, M.A.; Crowley, J.; Markaverich, B.M. Disruption of male sexual behavior in rats by tetrahydrofurandiols (THF-diols). Steroids, 2005, 70, 750-4.
136. Markaverich, B.M.; Crowley, J.R.; Alejandro, M.A.; Shoulars, K.; Casajuna, N.; Mani, S.; Reyna, A.; Sharp, J.; Leukotoxindiols from ground corncobbedding disrupt estrous cyclicity in rats and stimulate MCF-7 breast cancer cell proliferation. Environ. Health Perspect., 2005, 113, 1698-704.
137. Markaverich, B.M.; Alejandro, M.A.; Markaverich, D.; Zitzow, L.; Casajuna, N.; Camarao, N.; Hill, J.; Bhirdo, K.; Faith, R.; Turk, J.; Crowley, J.R. Identification of an endocrine disrupting agent from corn with mitogenic activity. Biochem. Biophys. Res. Commun., 2002, 291, 692-700.
138. Gillis, C. N. Panax ginseng phamacology: A nitric oxide link? Biochem. Pharmacol., 1997, 54, 1-8.
139. Liu,W.K., Xu, S.X.; Che, C.T. Anti-proliferative effect of ginsengsaponins on human prostate cancer cell line. Life Sci., 2000, 67, 1297-306.
140. Bhattaacharya, S.K.; Mitra, S.K. Anxiolytic activity of Panax ginseng roots: An experimental study. J. Ethnopharma, 1991, 34, 8792.
141. Attele, A.S.; Wu, J.A.; Yuan, C.S. Ginseng pharmacology: Multiple constituents and multiple actions. Biochem. Pharmacol., 1999, 58, 1685-93.
142. Chan, R.Y.K.; Chen, W-F.; Dong, A.; Guo, D.; Wong, M.S. Oestrogen-like activity of ginsenoside Rg1 derived from Panax notoginseng. J. Clin. Endocrinol. Metab., 2002, 87, 3691-5.
143. Lee, Y.; Jin, Y.; Lim, W.; Ji, S.; Choi, S.; Jang, S. A ginsenosideRh1, a component of ginseng saponin, activates oestrogen receptor in human breast carcinoma MCF-7 cells. J. Steroid Biochem. Mol. Biol., 2003, 84, 463-8.
144. Lee, Y.J.; Jin, Y.R.; Lim, W.C.; Park, W.K.; Cho, J.Y.; Jang, S. Ginsenoside-Rb1 acts as a weak phytooestrogen in MCF-7 human breast cancer cells. Arch. Pharm. Res., 2003, 26, 58-63.
145. Dong, S.; Kiyama, R. Characterisation of oestrogenic activity of ginsenosides in MCF-7 cells using a customised DNA microarray. Food Chem., 2009, 113, 672-8.
146. Borriello, S.P.; Setchell, K.D.R.; Axelson, M.; Lawson, A.M. Production and metabolism of lignans by the human faecal flora. J. Appl. Bacteriol., 1985, 58, 37-43.
147. Nilsson, M.; Åman, P.; Härkönen, H.; Bach Knudsen, K.E.; Mazur,W.; Adlercreutz, H. Content of nutrients and lignans in rollermilled fractions of rye. J. Sci. Food Agric., 1997, 73, 143-8.
148. Milder, I.E.; Arts, I.C.; Putte, B.; Venema, D.P.; Hollman, P.C. Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br. J. Nutr., 2005, 93, 393-402.
149. Milder, I.E.J.; Feskens, E.J.M.; Arts, I.C.W.; Bueno de Mesquita, H.B.; Peter, C.H.; Hollman, P.C.H.; Daan Kromhout, D. Intake of the plant lignans secoisolariciresinol, matairesinol, lariciresinol, and pinoresinol in Dutch men and women1. J. Nutr., 2005, 135, 1202-7.
150. Welshons, W.V.; Murphy, C.S.; Koch, R.; Calaf, G.; Jordan, V.C. Stimulation of breast cancer cells in vitro by the environmental estrogen enterolactone and the phytoestrogen equol. Breast Cancer Res. Treat., 1987, 10, 169-75.
151. Raffaelli, B.; Hoikkala, A.; Leppala, E; Wähälä, K. Enterolignans. J. Chromatogr. B. Biomed. Sci. Appl., 2002, 777, 29-43.
152. Arts, I.C.W.; Hollman, P.C.H. Polyphenols and disease risk in epidemiological studies. Am. J. Clin. Nutr., 2005, 81, 317S-25S.
153. Heinonen, S.; Nurmi, T.; Liukkonen, K.; Poutanen,K.; Wähälä, K.; Deyama, T.; Nishibe, S.; Adlercreutz, H. In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. J. Agric. Food Chem., 2001, 49, 3178-86.
154. Penttinen, P.; Jaehrling, J.; Damdimopoulos, A.E.; Inzunza, J.; Lemmen, J.G.; Saag, P.; Pettersson, K.; Gauglitz, G.; Mäkelä, S.; Pongratz, I. Diet-derived polyphenol metabolite enterolactone is a tissue specific estrogen receptor activator. Endocrinology, 2007, 148, 4875-86.
155. McCann, S.E.; Moysich, K.B.; Freudenheim, J.L.; Ambrosone, C.B.; Shields, P.G. The risk of breast cancer associated with dietary lignans differs by CYP17 genotype in women. J. Nutr., 2002, 132, 3036-41.
156. McCann, S.E.; Kulkarni, S.; Trevisan, M.; Vito, D.; Nie, J.; Edge, S.B.; Muti, P.; Freudenheim, J.L. Dietary lignan intakes and risk of breast cancer by tumor estrogen receptor status. Breast Cancer Res. Treat., 2006, 99, 309-11.
157. Sonestedt, E.; Ivarsson, M.I.; Harlid, S.; Ericson, U.; Gullberg, B.; Carlson, J.; Olsson, H.; Adlercreutz, H.; Wirfält, E. The protective association of high plasma enterolactone with breast cancer is reasonably robust in women with polymorphisms in the estrogen receptor alpha and beta genes. J. Nutr., 2009, 139, 993-1001.
158. Kassi, E.; Papoutsi, Z.; Fokialakis, N.; Messari, I.; Mitakou, S.; Moutsatsou, P. Greek plant extracts exhibit selective estrogen receptor modulator (SERM)-like properties. J. Agric. Food Chem., 2004, 52, 6956-61.
159. Türkyilmaz, Z.; Karabulut, R.; Sönmez, K.; Basaklar, A.C. A striking and frequent cause of premature thelarche in children: Foeniculum vulgare. J. Pediatr. Surg., 2008, 43, 2109-11.
160. Nassara, M.I.; Abdel-Razika, A.F.; ElKhrisya, Eel-D.; Dawidar, A.A.; Bystromc, A.; Mabry, T.J. A benzoquinone and flavonoids from Cyperus alopecuroides. Phytochemistry, 2002, 60, 385-7.
161. Nakagawa, Y.; Suzuki, T. Cytotoxic and xenoestrogenic effects via biotransformation of transanethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells. Biochem. Pharmacol., 2003, 66, 63-73.
162. Blair, R.M.; Fang, H.; W Branham, W.S.; Hass, B.S.; Dial, S.L.; Moland, C.L.; Tong, W.; Shi, L.; Perkins, R.; Sheehan, D.M. The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands. Toxicol. Sci., 2000, 54, 138-53.
163. Howes, M.J.R.; Houghton, P.J.; Barlow, D.J.; Pocock, V.J.; Milligan, S.R. Assessment of estrogenic activity in some common essential oil constituents. J. Pharm. Pharmacol., 2002, 54, 1521-8.
164. Kluth, D.; Banning, A.; Paur, I.; Blomhoff, R.; Brigelius-Flohé, R. Modulation of pregnane X receptor-and electrophile responsive element-mediated gene expression by dietary polyphenolic compounds. Free Radic. Biol. Med., 2007, 42, 315-25.
165. Williamson, G.; Plumb, G.W.; Uda, Y.; Price, K.P.; Rhodes, M.J.C. Dietary quercetin glicosides: antioxidant activity and induction of the anticarcinogenic phase II marker enzyme quinone reductase in hepa1c1c7 cells. Carcinogenesis, 1996, 17, 2385-7.
166. Walle, T.; Eaton, E.A.; Walle, U.K. Quercetin, a potent and specific inhibitor of the human P-form phenolsulfotransferase. Bio chem.Pharmacol., 1995, 50, 731-4.
167. Chun, Y.J.; Kim, M.Y.; Guengerich, F.P. Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochem. Biophys. Res. Commun., 1999, 262, 20-4.
168. Chan, W.K.; Delucchi, A.B. Resveratrol, a red wine constituent, is a mechanism-based inactivator of cytochrome P450 3A4. Life Sci., 2000, 67, 3103-12.
169. Hodek, P.; Krízková, J.; Burdová, K.; Sulc, M.; Kizek, R.; Hudecek, J.; Stiborová, M. Chemopreventive compounds--View from the other side. Chem. Biol. Interact., 2009, 180, 1-9.
170. Paolini, M.; Nestle, M. Pitfalls of enzyme-based molecular anticancer dietary manipulations: food for thought. Mutat. Res., 2003, 543, 181-9.
171. Mateescu, C.; Barbulescu, D. Enhanced nutritive, functional and therapeutic action of combined beeproducts in complex food supplements. Roum. Biotechnol. Lett., 1999, 4, 163-72.
172. Suzuki, K.M.; Isohama, Y.; Maruyama, H.; Yamada, Y.; Narita, Y.; Ohta, S.; Araki, Y.; Miyata, T.; Mishima, S. Estrogenic activities of Fatty acids and a sterol isolated from royal jelly. Evid. Based Complement. Alternat. Med., 2008, 5, 295-302.
173. nd ed. Eagan Press: St. Paul, MN, 1997.
174. Bennett, J.W.; Klich, M. Mycotoxins. Clin. Microbiol. Rev., 2003, 16, 497-516.
175. van Egmond, H. Worldwide regulations for mycotoxins. Adv. Exp. Med. Biol., 2002, 504, 257-69.
176. Takemura, H.; Shim, J.Y.; Sayama, K.; Tsubura, A.; TingZhu, B.; Shimoi, K. Characterization of the estrogenic activities of zearalenone and zeranol in vivo and in vitro. J. Steroid Biochem. Mol. Biol., 2007, 103, 170-7.
177. Lerner, L.J.; Jordan, V.C. Development of antiestrogens and their use in breast cancer: eighth Cain memorial award lecture. Cancer Res., 1990, 50, 4177-89.
178. Smith, C.L.; O'Malley, B.W. Coregulator function: a key to understanding tissue specificity of selective receptor modulators. Endocr. Rev., 2004, 25, 45-71.
179. Bolego, C.; Vegeto, E.; Pinna, C., Maggi, A.; Cignarella, A. Selective agonists of estrogen receptor isoforms: new perspectives for cardiovascular disease. Arterioscler. Thromb. Vasc. Biol., 2006, 26,:2192-2199.
180. Courrier, R.; Horeau, A.; Jacques, J. Sur un nouvel oestrogene artificiel de grande activite. Compt. Rend. Soc. De Biol., 1948, 141, 159-61.
181. Herbai, G. Separation of growth inhibiting potency from oestrogenicity in different weak oestrogenic drugs of various chemical structures. Acta Endocrinol., 1971, 68, 249-63.
182. Crawley, G.C. Hormones-Nonsteroidal Estrogens. In Kirk-Othmer Encyclopedia of Chemical Technology, 3rd Ed.; Grayson, M., Eckroth, D., Eds.; Wiley: New York, 1980; Vol. 12, p.670.
183. Soto, A.M.; Meyers, C.Y.; Sonnenschein, C. The Endocrine Society, 70th Annual Meeting, New Orleans, Abstract 1988.
184. ®). ARKIVOC, 2000, (ii), 95-102.
185. Miescher, K. On doisynolic acids, a new class of estrogens. Chem. Rev., 1948, 43, 367-84.
186. Meyers, C.Y.; Kolb, V.M.; Gass, G.H.; Rao, B.R.; Roos, C.F.; Dandliker, W.B. Doisynolic-type acids-uterotropically potent estrogens which compete poorly with estradiol for cytosolic estradiol receptors. J. Steroid. Biochem., 1988, 31, 393-404.
187. Meyers, C.Y.; Hou, Y.; Winters, T.A.; Banz, W.J.; Adler, S. Activities of a non-classical estrogen, Z-bis-dehydrodoisynolic acid, with ER and ER. J. Steroid Biochem. Mol. Biol., 2002, 82, 3344.
188. Adler, M.; Hou, Y.; Sandrock, P.; Meyers, C.Y.; Winters, T.A.; Banz, W.J.; Adler, S. Derivatives of Z-bisdehydrodoisynolic acid provide a new description of the binding-activity paradox and selective estrogen receptor modulator activity. Endocrinology, 2006, 147, 3952-60.
189. Takaoka, M. Of the phenolic substances of white hellebore (Veratrum grandiflorum Loes.fil.). J. Fac. Sci. Hokkaido Imp. Univ. Ser.III., 1940, 3, 1-16.
190. Siemann, E.H.; Creasy, L.L. Concentration of the phytoalexin resveratrol in wine. Am. J. Enol. Vitic., 1992, 43, 49-52.
191. Signorelli, P.; Ghidoni, R. Resveratrol as an anticancer nutrient: molecular basis, open questions and promises. J. Nutr. Biochem., 2005, 16, 449-66.
192. Langcake, P.; Pryce, R.J. The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection or injury. Physiol. Plant Pathol., 1976, 9, 77-86.
193. Pace-Asciak, C.R.; Hahn, S.; Diamandis, E.P.; Soleas, G.; Goldberg, D.M. The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease. Clin.Chim. Acta, 1995, 235, 207-19.
194. Frankel, E.N.; Waterhouse, A.L.; Kinsella, J.E. Inhibition of human LDL oxidation by resveratrol. Lancet, 1993, 341, 1103-4.
195. Gehm, B.D.; Mcandrews, J.M.; Chien, P-Y.; Jameson. L.J. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc. Natl. Acad. Sci. USA Physiol., 1997, 94, 14138-43.
196. Le Corre, L.; Chalabi, N.; Delort, L.; Bignon, Y.J.; Bernard-Gallon, D.J. Resveratrol and breast cancer chemoprevention: molecular mechanisms. Mol. Nutr. Food Res., 2005, 49, 462-71.
197. Gehm, B.D.; Levenson, A.S.; Liu, H.; Lee, E-J.; Amundsen, B.M.; Cushman, M.; Jordan, V.C.; Jameson, J.L.; Shiau, A.K.; Barstad, D.; Loria, P.M.; Cheng, L.; Kushner, P. Estrogenic effects of resveratrol in breast cancer cells expressing mutant and wild-type estrogen receptors: role of AF-1 and AF-2. J. Steroid Biochem. Mol. Biol., 2004, 88, 223-34.
198. Bhat, K.P.L.; Lantvit, D.; Christov, K.; Mehta, R.G.; Moon, R.C.; Pezzuto, J.M. Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models. Cancer Res., 2001, 61, 7456-63.
199. Mueller, S.O.; Simon, S.; Chae, K.; Metzler, M.; Korach, K.S. Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor (ER) and ER in human cells. Toxicol. Sci., 2004, 80, 14-25.
200. Potter, G.A.; Patterson, L.H.; Wanogho, E.; Perry, P.J.; Butler, P.C.; Ijaz, T.; Ruparelia, K.C.; Lamb, J.H.; Farmer, P.B.; Stanley, l.A.; Burke, M.D. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochromes P450 enzyme CYP1B1. Br. J. Cancer, 2002, 86, 774-8.
201. Wolter, F.; Clausnitzer, A.; Akoglu, B.; Stein, J. Piceatannol, a natural analog of resveratrol, inhibits progression through the S phase of the cell cycle in colorectal cancer cell lines. J. Nutr., 2002, 132, 298-302.
202. Vo, T.P.; Madlener, S.; Bago-Horvath, Z.; Herbacek, I.; Stark, N.; Gridling, M.; Probst, P.; Giessrigl, B.; Bauer, S.; Vonach, C.; Saiko, P.; Grusch, M.; Szekeres, T.; Fritzer-Szekeres, M.; Jäger, W.; Krupitza, G.; Soleiman, A. Proand anti-carcinogenic mechanisms of piceatannol are activated dose-dependently in MCF-7 breast cancer cells. Carcinogenesis, 2009 Aug 20.
203. [Epub ahead of print]
204. Shiau, A.K.; Barstad, D.; Loria, P.M.; Cheng, L.; Kushner, P.J.; Agard, D.A.; Greene, G.L. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell, 1998, 95, 927-37.
205. Waibel, M.; De Angelis, M.; Stossi, F.; Kieser, K.J.; Carlson, K.E.; Katzenellenbogen, B.S.; Katzenellenbogen, J.A. Bibenzyland stilbene-core compounds with non-polar linker atom substituents as selective ligands for estrogen receptor beta. Eur. J. Med. Chem., 2009, 44, 3412-24.
206. De Angelis, M.; Katzenellenbogen, J.A. Ringnitrogen-substituted non-steroidal estrogens: pyridine and pyrimidine analogs of the phenol in deoxyhexestrole xperience resonance constraints on preferred ligand conformation. Bioorg. Med. Chem. Lett., 2004, 14, 5835-9.
207. Meyers, M.J.; Sun, J.; Carlson, K.E.; Marriner, G.A.; Katzenellenbogen, B.S.; Katzenellenbogen, J.A. Estrogen receptorpotencyselective ligands: structure activity relationship studies of diarylpropionitriles and their acetylene and polar analogues. J. Med. Chem., 2001, 44, 4230-51.
208. Weiser, M.J.; Wu, T.J.; Handa, R.J. Estrogen receptor beta (ER) agonist diarylpropionitrile (DPN): biological activities of Rand Senantiomers on behavior and hormonal response to stress. Endocrinology, 2009, 150, 1817-25.
209. Lerner, L.J.; Holthaus, J.F.; Thompson, C.R. A non-steroidal estrogenantagonist1-(p-2-diethylaminoethoxyphenyl)-1-phenyl-2-pmethoxyphenylethanol. Endocrinology, 1958, 63, 295-318.
210. Harper, M.J.; Walpole, A.L. A new derivative of triphenylethylene: effect on implantation and mode of action in rats. J. Reprod. Fertil., 1967, 13, 101-19.
211. Jordan, V.C. The development of tamoxifen for breast cancer therapy: atribute to the late Arthur L.Walpole. Breast Cancer Res. Treat., 1988, 11, 197-209.
212. Jordan, V.C. Tamoxifen: a most unlikely pioneering medicine. Nat. Rev. Drug Discov., 2003, 2, 205-13.
213. Jordan, V.C.; Collins, M.M.; Rowsby, L.; Prestwich, G. A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity. J. Endocrinol., 1977, 75, 305-16.
214. Lerner, L.J.; Jordan, V.C. Development of antiestrogens and their use in breast cancer: Eighth Cain memorial award lecture. Cancer Res., 1990, 50, 4177-89.
215. Gust, R.; Lubczyk, V.J. Investigations on the influence of terminal groups at the C2-propyl side chain of 1,1-bis(4-hydroxyphenyl)-2phenylpent-1-ene and 1,1,2-tris(4-hydroxyphenyl)pent-1-ene on the estrogen receptor binding and the estrogenic/anti-estrogenic properties. Steroid Biochem. Mol. Biol., 2003, 86, 57-70.
216. Kim, S.H.; Katzenellenbogen, J.A. Triarylethylene bisphenols with a novel cycle are ligands for the estrogen receptor. Bioorg. Med. Chem., 2000, 8, 785-93.
217. Watanabe, O.; Ikeno, A.; Minato, H.; Nakagawa, H.; Kohayakawa, C.; Tsuji, J. Discovery and preclinical characterization of (+)-3[4(1-piperidinoethoxy)phenyl]spiro [indene-1,1 -indane]-5,5 -dio-lhydrochloride: A promising nonsteroidal estrogen receptor agonist for hot flush. J. Med. Chem., 2003, 46, 3961-4.
218. Roelens, F.; Heldring, N.; Dhooge, W.; Bengtsson, M.; Comhaire, F.; Gustafsson, J.; Treuter, E.; De Keukeleire, D. Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors and. J. Med. Chem., 2006, 49, 7357-65.
219. Norman, B.H.; Dodge, J.A.; Richardson, T.I.; Borromeo, P.S.; Lugar, C.W.; Jones, S.A.; Chen, K.; Wang, Y.; Durst, G.L.; Barr, R.J.; Montrose-Rafizadeh, C.; Osborne, H.E.; Amos, R.M.; Guo, S.; Boodhoo, A. Venkatesh krishnan benzopyrans are selective estrogen receptor agonists with novel activity in models of benign prostatic hyperplasia. J. Med. Chem., 2006, 49, 6155-7.
220. Richardson, T.I.; Norman, B.H.; Lugar, C.W.; Jones, S.A.; Wang, Y.; Durbin, J.D.; Krishnan, V.; Dodge, J.A. Benzopyrans as selective estrogen receptor agonists (SERBAs). Part 2: Structureactivity relationship studies on the benzopyran scaffold. Bioorg. Med. Chem. Lett., 2007, 17, 3570-4.
221. Richardson, T.I.; Dodge, J.A.; Durst, G.L.; Pfeifer, L.A.; Shah, J.; Wang, Y.; Durbin, J.D.; Krishnan, V.; Norman, B.H. Benzopyrans as selective estrogen receptor agonists (SERBAs). Part 3: Synthesis of cyclopentanone and cyclohexanone intermediates for C-ring modification. Bioorg. Med. Chem. Lett., 2007, 17, 4824-8.
222. Malamas, M.S.; Manas, E.S.; McDevitt, R.E.; Gunawan, I.; Xu, Z.B.; Collini, M.D.; Miller, C.P.; Dinh, T.; Henderson, R.A.; Keith Jr. J.C.; Harris, H.A. Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor-ligands. J. Med. Chem., 2004, 47, 5021-40.
223. Hughes, Z.A.; Liu, F.; Platt, B.J.; Dwyer, J.M.; Pulicicchio, C.M.; Zhang, G.; Schechter, L.E.; Rosenzweig-Lipson, S.; Day, M. WAY-200070, a selective agonist of estrogen receptor beta as a potential novel anxiolytic/antidepressant agent. Neuropharmacol., 2008, 54, 1136-42.
224. Stauffer, S.R.; Coletta, C.J.; Tedesco, R.; Nishiguchi, G.; Carlson, K.; Sun, J.; Katzenellenbogen, B.S.; Katzenellenbogen, J.A. Pyrazole ligands:structure-affinity/ activity relationships and estrogen receptor-selective agonists. J. Med. Chem., 2000, 43, 4934-47.
225. Thammacharoen, S.; Geary, N.; Lutz, T.A.; Ogawa, S.; Asarian, L. Divergent effects of estradiol and the estrogen receptor-alpha agonist PPT on eating and activation of PVN CRH neurons in ovariectomized rats and mice. Brain Res., 2009, 1268, 88-96.
226. Lundholm, L.; Bryzgalova, G.; Gao, H.; Portwood, N.; Fält, S.; Berndt, K.D.; Dicker, A.; Galuska, D.; Zierath, J.R.; Gustafsson, J.A.; Efendic, S.; Dahlman-Wright, K.; Khan, A. The estrogen receptor {alpha}-selective agonist propyl pyrazole triol improves glucose tolerance in ob/ob mice; potential molecular mechanisms. J. Endocrinol., 2008, 199, 275-86.
227. Cignarella, A.; Bolego, C.; Pelosi, V.; Meda, C.; Krust, A.; Pinna, C.; Gaion, R.M.; Vegeto, E.; Maggi, A. Distinct roles of estrogen receptor-alpha and beta in the modulation of vascular inducible nitric-oxide synthase in diabetes. J. Pharmacol. Exp. Ther., 2009, 328, 174-82.
228. Alda, J.O.; Valero, M.S.; Pereboom, D.; Gros, P.; Garay, R.P. Endothelium-independent vasorelaxation by the selective alpha estrogen receptor agonist propyl pyrazole triol in rat aortic smooth muscle. J. Pharm. Pharmacol., 2009, 61, 641-6.
229. Steffan, R.J.; Matelan, E.; Ashwell, M.A.; Moore, W.J.; Solvibile, W.R.; Trybulski, E.; Chadwick, C.C.; Chippari, S.; Kenney, T.; Eckert, A.; Borges-Marcucci, L.; Keith, J.C.; Xu, Z.; Mosyak, L.; Harnish, D.C. Synthesis and activity of substituted 4-(indazol-3yl)phenols as pathway-selective estrogen receptor ligands useful in the treatment of rheumatoid arthritis. J. Med. Chem., 2004, 47, 26.
230. Booth, E.A.; Marchesi, M.; Knittel, A.K.; Kilbourne, E.J.; Lucchesi, B.R. The pathway-selective estrogen receptor ligand WAY169916 reduces infarct size after myocardial ischemia and reperfusion by an estrogen receptor dependent mechanism. J. Cardiovasc. Pharmacol., 2007, 49, 401-7.
231. Chen, W.; Lin, Z.; Ning, M.; Yang, C.; Yan, X.; Xie, Y.; Shena, X.; Wang, M-W. Aza analogues of equol: Novel ligands for estrogen receptor. Bioorg. Med. Chem., 2007, 15, 5828-36.
232. Zhou, H.B.; Nettles, K.W.; Bruning, J.B.; Kim, Y.; Joachimiak, A.; Sharma, S.; Carlson, K.E.; Stossi, F.; Katzenellenbogen, B.S.; Greene, G.L.; Katzenellenbogen, J.A. Elemental isomerism: A boron-nitrogen surrogate for a carbon-carbon double bond increases the chemical diversity of estrogen receptor ligands. Chem. Biol., 2007, 14, 659-69.
233. Simonich, S.L.; Hites, R.A. Global distribution of persistent organochlorine compounds. Science, 1995, 269, 1851-4.
234. Giusti, M.; Iwamoto, K.; Hatch, E.E. Diethylstilbestrol revisited: a review of the long-term health effects. Ann. Intern. Med., 1995, 122, 778-88.
235. McLachlan, J.A. Environmental signaling: what embryos and evolution teach us about endocrine disrupting chemicals. Endocrine Rev., 2001, 22, 319-41.
236. Fisher, B.E. Most unwanted. Persistent organic pollutants. Environ. Health Perspect., 1999, 107, A18-23.
237. Sonnenschein, C.; Soto, A.M. An updated review of environmental estrogen and androgen mimics and antagonists. J. Steroid Biochem. Mol. Biol., 1998, 65, 143-50.
238. Moore, M.; Mustain, M.; Daniel, K., Chen, I.; Safe, S.; Zacharewski, T.; Gillesby, B.; Joyeux, A.; Balaguer, P. Antiestrogenic activity of hydroxylated polychlorinated biphenyl congeners identified in human serum. Toxicol. Appl. Pharmacol., 1997, 142, 160-8.
239. Shekhar, P.V.; Werdell, J.; Basrur, V.S. Environmental estrogen stimulation of growth and estrogen receptor function in preneoplastic and cancerous human breastcelllines. J. Natl. Cancer Inst., 1997, 89, 1774-82.
240. Gaido, K.W.; Maness, S.C.; McDonnell, D.P.; Dehal, S.S.; Kupfer, D.; Safe, S. Interaction of methoxychlor and related compounds with estrogen receptor alpha and beta, and androgen receptor: structure-activity studies. Mol. Pharmacol., 2000, 58, 852-8.
241. Paris, F.; Balaguer, P.; Terouanne, B.; Servant, N.; Lacoste, C.; Cravedi, J.P.; Nicolas, J.C.; Sultan, C. Phenylphenols biphenols, bisphenol-A and 4-tert-octylphenol exhibit alpha and beta estrogen activities and antiandrogen activity in reporter cell lines. Mol. Cell. Endocrinol., 2002, 193, 43-9.
242. Nimrod, A.C.; Benson, W.H. Environmental estrogenic effects of alkylphenol ethoxylates. Crit. Rev. Toxicol., 1996, 26, 335-64.
243. Gomez, E.; Pillon, A.; Fenet, H.; Rosain, D.; Duchesne, M.J.; Nicolas, J.C.; Balaguer, P.; Casellas, C. Estrogenic activity of cosmetic components in reporter cell lines:parabens, UV screens, and musks. J. Toxicol. Environ. Health Part A, 2005, 68, 239-51.
244. Welshons,W.V.; Thayer, K.A.; Judy, B.M.; Taylor, J.A.; Curran, E.M.; vom-Saal, F.S.; Large effects from small exposures. I. Mechanisms for endocrine-disrupting chemicals with estrogenic activity. Environ. Health Perspect., 2003, 111, 994-1006.
245. Fox, J.E.; Starcevic, M.; Jones, P.E.; Burow, M.E.; McLachlan, J.A. Phytoestrogen signaling and symbiotic gene activation are disrupted by endocrine-disrupting chemicals. Environ. Health Perspect., 2004, 112, 672-7.
246. Mackay, D.; Fraser, A. Kenneth Mellanby Review Award. Bioaccumulation of persistent organic chemicals: mechanisms and models. Environ. Pollut., 2000, 110, 375-91.
247. Soto, A.; Sonnenschein, C.; Chung, K.L.; Fernandez, M.F.; Olea, N.; Olea-Serrano, M.F. The E-Screen as a tool to identify estrogens: an update on oestrogenic environment pollutants. Environ. Health Perspect., 1995, 103, 113-22.
248. Fernandez, M.F.; Molina-Molina, J.M.; Lopez-Espinosa, M.J.; Freire, C.; Campoy, C.; Ibarluzea, J.; Torne, P.; Pedraza, V.; Olea N. Biomonitoring of environmental estrogens in human tissues. Int. J. Hyg. Environ. Health, 2007, 210, 429-32.
249. Lemaire, G.; Mnif, W.; Mauvais, P.; Balaguer, P.; Rahmani, R. Activation of and -estrogen receptors by persistent pesticides in reporter cell lines. Life Sci., 2006, 79, 1160-9.
250. Bentrem, D.; Fox, J.E.; Pearce, S.T.; Liu, H.; Pappas, S.; Kupfer, D.; Zapf, J.W.; Jordan, V.C. Distinct molecular conformations of the estrogen receptor complex exploited by environmental estrogens. Cancer Res., 2003, 63, 7490-6.
251. Gulledge, C.C.; Burow, M.E.; McLachlan, J.A. Endocrine disruption in sexual differentiation and puberty. What do pseudohermaphroditic polar bears have to do with the practice of pediatrics? Pediatr. Clin. N. Am., 2001, 48, 1223-40.
252. Tyler, C.R.; Jobling, S.; Sumpter, J.P. Endocrine disruption in wildlife: a critical review of the evidence. Crit. Rev. Toxicol., 1998, 28, 319-61.
253. Ahlborg, U.G.; Lipworth, L.; Titus-Ernstoff, L.; Hsieh, C.C.; Hanberg, A.; Baron, J.; Trichopoulos, D.; Adami, H.O. Organochlorine compounds in relation to breast cancer, endometrial cancer, and endometriosis: an assessment of the biological and epidemiological evidence. Crit. Rev. Toxicol., 1995, 25, 463-531.
254. Cocco, P.; Kazerouni, N.; Zahm, S.H. Cancer mortality and environmental exposure to DDE in the United States. Environ. Health Perspect., 2000, 108, 1-4.
255. Korrick, S.A.; Chen, C.; Damokosh, A.I.; Ni, J.; Liu,X.; Cho, S.I.; Altshul, L.; Ryan, L.; Xu, X. Association of DDT with spontaneous abortion: a case-control study. Ann. Epidemiol., 2001, 11, 491-6.
256. Beard, J.; Marshall, S.; Jong, K.; Newton, R.; Triplett-McBride, T.; Humphries, B.; Bronks, R. 1,1,1-trichloro-2,2-bis (pchlorophenyl)ethane (DDT) and reduced bone mineral density. Arch. Environ. Health, 2000, 55, 177-80.
257. Skakkebaek, N.E.; Rajpert-De Meyts, E.; Jorgensen, N.; Carlsen, E.; Petersen, P.M.; Giwercman, A.; Andersen, A.G.; Jensen, T.K.; Andersson, A.M.; Muller, J. Germ cell cancer and disorders of spermatogenesis: an environmental connection? APMIS, 1998, 106, 3-11.
258. Watson, C.S.; Bulayeva, N.N.; Wozniak, A.L.; Alyea, R.A. Xenoestrogens are potent activators of nongenomic estrogenic responses. Steroids, 2007, 72, 124-34.
259. Frigo, D.E.; Burow, M.E.; Mitchell, K.A.; Chiang, T.C.; McLachlan, J.A. DDT and its metabolites alter gene expression in human uterine cell lines through estrogen receptor-independent mechanisms. Environ. Health Perspect., 2002, 110, 1239-45.
260. Akahori, Y.; Nakai, M.; Yamasaki, K.; Takatsuki, M.; Shimohigashi, Y.; Ohtaki, M. Relationship between the results of in vitro receptor binding assay to human estrogen receptor a and in vivo uterotrophic assay: Comparative study with 65 selected chemicals. Toxicol. In Vitro, 2008, 22, 225-31.
261. Wu, F.; Khan, S.; Wu, Q.; Barhoumi, R.; Burghardt, R.; Safe, S. Ligand structure-dependent activation of estrogen receptor alpha/Sp by estrogens and xenoestrogens. J. Steroid Biochem. Mol. Biol., 2008, 110, 104-15.
262. Das, S.K.; Taylor, J.A.; Korach, K.S.; Paria, B.C.; Dey, S.K.; Lubahn, D.B. Estrogenic responses in estrogen receptordeficient mice reveal a distinct estrogen signaling pathway. Proc. Natl. Acad. Sci. USA, 1997, 94, 12786-91.
263. Li, J.; Li, N.; Ma, M.; Giesy, J.P.; Wang, Z. In vitro profiling of the endocrine disrupting potency of organochlorine pesticides. Toxicol. Lett., 2008, 183, 65-71.
264. Kester, M.H.; Bulduk, S.; Tibboel, D.; Meinl, W.; Glatt, H.; Falany, C.N.; Coughtrie, M.W.; Bergman, A.; Safe, S.H.; Kuiper, G.G.; Schuur, A.G.; Brouwer, A.; Visser, T.J. Potent inhibition of estrogen sulfotransferase by hydroxylated PCB metabolites: a novel pathway explaining the estrogenic activity of PCBs. Endocrinology, 2000, 141, 1897-900.
265. Krishnan, A.V.; Stathis, P.; Permuth, S.F.; Tokes, L.; Feldman, D. Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology, 1993, 132, 2279-86.
266. Staples, C.A.; Dorn, P.B.; Klecka, G.M.; O'Block, S.T.; Harris, L.R. A review of the environmental fate, effects, and exposures of bisphenol A. Chemosphere, 1998, 36, 2149-73.
267. Muncke, J. Exposure to endocrine disrupting compounds via the food chain: Is packaging a relevant source? Sci. Total Environ., 2009, 407, 4549-59.
268. Lee, S.Y.; Greener, E.H.; Menis, D.L. Detection of leached moieties from dental composites in fluids simulating food and saliva. Dent Mater., 1995, 11, 348-53.
269. Rivas, A.; Lacroix, M.; Olea-Serrano, F.; Laios, I.; Leclercq, G.; Olea, N. Estrogenic effect of a series of bisphenol analogues on gene and protein expression in MCF-7 breast cancer cells. J. Steroid Biochem. Mol. Biol., 2002, 82, 45-53.
270. Fukazawa, H.; Hoshino, K.; Shiozawa, T.; Matsushita, H.; Terao, Y. Identification and quantification of chlorinated bisphenol A in wastewater from wastepaper recycling plants. Chemosphere, 2001, 44, 973-9.
271. Rivas, A.; Fernandez, M.F.; Cerrillo, I.; Ibarluzea, J.; Olea-Serrano, M.F.; Pedraza, V.; Olea, N. Human exposure to endocrine disrupters: standardisation of a marker of estrogenic exposure in adipose tissue. APMIS, 2001, 103, 189-201.
272. Muhlhauser, A.; Susiarjo, M.; Rubio, C.; Griswold, J.; Gorence, G.; Hassold, T.; Hunt, P.A. Bisphenol A effects on the growing mouse oocyte are influenced by diet. Biol. Reprod., 2009, 80, 1066-71.
273. van Lipzig, M.M.H.; Laak, A.M.; Jongejan, A.; Vermeulen, N.P.E.; Wamelink, M.; Geerke, D.; Meerman, J.H.N. Prediction of ligand binding affinity and orientation of xenoestrogens to the estrogen receptor by molecular dynamics simulations and the linear interaction energy method. J. Med. Chem., 2004, 47, 1018-30.
274. Whitlock, J.P. Genetic and molecular aspects of 2,3,7,8tetrachlorodibenzo-p-dioxin action. Ann. Rev. Pharmacol., 1990, 30, 251-77.
275. Safe, S.; Wormke, M.; Samudio, I. Mechanisms of inhibitory aryl hydrocarbon receptor-estrogen receptor crosstalk in human breast cancer cells. J. Mammary Gland Biol. Neopl., 2000, 5, 295-306.
276. Swedenborg, E.; Pongratz, I. AhR and ARNT modulate ER signaling. Toxicology, 2010, 268, 132-8.
277. Boverhof, D.R.; Burgoon, L.D.; Williams, K.J.; Zacharewski, T.R. Inhibition of estrogen-mediated uterine gene expression responses by dioxin. Mol. Pharmacol., 2008, 73, 82-93.
278. Rüegg, J.; Swedenborg, E.; Wahlström, D.; Escande, A.; Balaguer, P.; Pettersson, K.; Pongratz, I. The transcription factor aryl hydrocarbon receptor nuclear translocator functions as an estrogen receptor -selective coactivator, and its recruitment to alternative pathways mediates antiestrogenic effects of dioxin. Mol. Endocrinol., 2008, 22, 304-16.
279. Kitajima, M.; Khan, K.N.; Fujishita, A.; Masuzaki, H.; Ishimaru, T. Histomorphometric alteration and cell-type specific modulation of arylhydrocarbon receptor and estrogen receptor expression by 2,3,7,8-tetrachlorodibenzopdioxin and 17 beta-estradiol in mouse experimental model of endometriosis. Reprod. Toxicol., 2004, 18, 793-801.
280. Yu, J.; Wang, Y.; Zhou, W.H.; Wang, L.; He, Y.Y.; Li, D.J. Combination of estrogen and dioxin is involved in the pathogenesis of endometriosis by promoting chemokine secretion and invasion of endometrial stromal cells. Hum. Reprod., 2008, 23, 1614-26.
281. Stoica, A.; Katzenellenbogen, B.S.; Martin, M.B. Activation of estrogen receptorby the heavy metal cadmium. Mol. Endocri nol., 2000, 14, 545-53.
282. Nesatyy, V.J.; Rutishauser, B.V.; Eggen, R.I.; Suter, M.J. Identification of the estrogen receptor Cd-binding sites by chemical modification. Analyst, 2005, 130, 1087-97.
283. Silva, E.; Lopez-Espinosa, M.J.; Molina-Molina, J.M.; Fernández, M.; Olea, N.; Kortenkamp, A. Lack of activity of cadmium in in vitro estrogenicity assays. Toxicol. Appl. Pharmacol., 2006, 216, 208.
284. Höfer, N.; Diel, P.; Wittsiepe, J.; Wilhelm, M.; Degen, G.H. Doseand route-dependent hormonal activity of the metalloestrogen cad mium in the rat uterus. Toxicol. Lett., 2009, 191, 123-31.