The relation between the chemical structure of flavonoids and their estrogen-like activities

Current Medicinal Chemistry

Volumn 11, Issue 10, 2004, Pages 1333-1343

  Vaya, Jacob ^a,b   Tamir, Snait ^a,b  

^a MIGAL GALILEE TECHNOLOGY CENTER   (Israel)

^b TEL HAI COLLEGE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

1,1,2 TRIPHENYLETHYLENE DERIVATIVE; APIGENIN; CHALCONE DERIVATIVE; CHOLESTEROL; COUMESTROL; DAIDZEIN; ENTEROLACTONE; EQUOL; ESTRADIOL; ESTROGEN; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FLAVONOID; FORMONONETIN; GENISTEIN; GLYCOSIDE; ISOFLAVONE DERIVATIVE; ISOFLAVONOID; ISOLIQUIRITIGENIN; LOW DENSITY LIPOPROTEIN CHOLESTEROL; MACROLIDE; NARINGENIN; PHYTOESTROGEN; RESVERATROL; STEROID HORMONE; STILBENE DERIVATIVE; TAMOXIFEN; TRIACYLGLYCEROL; UNINDEXED DRUG; ZERANOL;

BONE DENSITY; BREAST CANCER; CANCER GROWTH; CARCINOGENESIS; CARDIOVASCULAR DISEASE; CLINICAL TRIAL; CORRELATION ANALYSIS; DIETARY INTAKE; DRUG ABSORPTION; DRUG METABOLISM; ENDOMETRIAL DISEASE; ESTROGEN ACTIVITY; ESTROGEN DEFICIENCY; GEOGRAPHIC DISTRIBUTION; HEART PROTECTION; HOMEOSTASIS; HORMONE SUBSTITUTION; HUMAN; INCIDENCE; MENOPAUSAL SYNDROME; NONHUMAN; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REVIEW; UTERUS CANCER; VAGINA BLEEDING;

EID: 2342567855     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867043365251     Document Type: Review

References (78)

1. Iafrati, M.D.; Karas, R.H.; Aronovitz, M.; Kim, S.; Sullivan, T.R., Jr.; Lubahn, D.B.; O'Donnell, T.F., Jr.; Korach, K.S.; Mendelsohn, M.E. Nat. Med. 1997, 3, 545.
2. Korach, K.S. Science. 1994, 266, 1524.
3. Bachmann, G.A. Am. J. Obstet. Gynecol. 1999, 180, S312.
4. Barton, D.; Loprinzi, C.; Wahner-Roedler, D. Drugs Aging. 2001, 18, 597.
5. Limouzin-Lamothe, M.A.; Mairon, N.; Joyce, C.R.; Le Gal, M. Am. J. Obstet. Gynecol. 1994, 170, 618.
6. Ettinger, B.; Genant, H.K.; Cann, C.E. Ann Intern Med. 1985, 102, 319.
7. Manolagas, S.C.; Kousteni, S.; Jilka, R.L. Recent Prog Horm Res. 2002, 57, 385.
8. Seed, M. Atherosclerosis. 1991, 90, 1.
9. Sourander, L.; Rajala, T.; Raiha, I.; Makinen, J.; Erkkola, R.; Helenius, H. Lancet. 1998, 352, 1965.
10. Stampfer, M.J.; Colditz, G.A.; Willett, W.C.; Manson, J.E.; Rosner, B.; Speizer, F.E.; Hennekens, C.H. N. Engl. J. Med. 1991, 325, 756.
11. Shewmon, D.A.; Stock, J.L.; Rosen, C.J.; Heiniluoma, K.M.; Hogue, M.M.; Morrison, A.; Doyle, E.M.; Ukena, T.; Weale, V.; Baker, S. Arterioscler. Thromb. 1994, 14, 1586.
12. Herrington, D.M.; Reboussin, D.M.; Brosnihan, K.B.; Sharp, P.C.; Shumaker, S.A.; Snyder, T.E.; Furberg, C.D.; Kowalchuk, G.J.; Stuckey, T.D.; Rogers, W.J.; Givens, D.H.; Waters, D. N. Engl. J. Med. 2000, 343, 522.
13. Rossouw, J.E.; Anderson, G.L.; Prentice, R.L.; LaCroix, A.Z.; Kooperberg, C.; Stefanick, M.L.; Jackson, R.D.; Beresford, S.A.; Howard, B.V.; Johnson, K.C.; Kotchen, J.M.; Ockene, J. Jama. 2002, 288, 321.
14. Russo, I.H.; Russo, J. J. Mammary. Gland. Biol. Neoplasia. 1998, 3, 49.
15. Rodriguez, C.; Patel, A.V.; Calle, E.E.; Jacob, E.J.; Thun, M.J. Jama. 2001, 28-5, 1460.
16. Tham, D.M.; Gardner, C.D.; Haskell, W.L. J. Clin. Endocrinol. Metab. 1998, 83, 2223.
17. Cassidy, A.; Bingham, S.;Carson, J. FASEB J., 1993, 7(3 pt II), 5000.
18. Spencer, J.P.; Chowrimootoo, G.; Choudhury, R.; Debnam, E.S.; Srai, S.K.; Rice-Evans, C. F. E. B. S Lett. 1999, 458, 224.
19. Setchell, K.D. J. Nutr. 2000, 130, 654S.
20. Lee, H.P.; Gourley, L.; Duffy, S.W.; Esteve, J.; Lee, J.; Day, N.E. Lancet. 1991, 337, 1197.
21. Fournier, D.B.; Erdman, J.W., Jr.; Gordon, G.B. Cancer Epidemiol Biomarkers Prev. 1998, 7, 1055.
22. Adlercreutz, H.; Markkanen, H.; Watanabe, S. Lancet. 1993, 342, 1209.
23. Baird, D.D.; Umbach, D.M.; Lansdell, L.; Hughes, C.L.; Setchell, K.D.; Weinberg, C.R.; Haney, A.F.; Wilcox, A.J.; McLachlan, J.A. J. Clin. Endocrinol. Metab. 1995, 80, 1685.
24. Duncan, A.M.; Underhill, K.E.; Xu, X.; Lavalleur, J.; Phipps, W.R.; Kurzer, M.S. J. Clin. Endocrinol. Metab. 1999, 84, 3479.
25. Cassidy, A.; Bingham, S.; Setchell, K.D. Am. J. Clin. Nutr. 1994, 60, 333.
26. Knight, D.C.; Eden, J.A. Obstet. Gynecol. 1996, 87, 897.
27. Potter, S.M.; Baum, J.A.; Teng, H.; Stillman, R.J.; Shay, N.F.; Erdman, J.W., Jr. Am. J. Clin. Nutr. 1998, 68, 1375S.
28. Gambacciani, M.; Ciaponi, M.; Cappagli, B.; Piaggesi, L.; Genazzani, A.R. Maturitas. 1997, 28, 75.
29. Valente, M.; Bufalino, L.; Castiglione, G.N.; D'Angelo, R.; Mancuso, A.; Galoppi, P.; Zichella, L. Calcif. Tissue. Int. 1994, 54, 377.
30. Anderson, J.W.; Johnstone, B.M.; Cook-Newell, M.E. N. Engl. J. Med. 1995, 333, 276.
31. Murkies, A.L.; Lombard, C.; Strauss, B.J.; Wilcox, G.; Burger, H.G.; Morton, M.S. Maturitas. 1995, 21, 189.
32. Albertazzi, P.; Pansini, F.; Bonaccorsi, G.; Zanotti, L.; Forini, E.; De Aloysio, D. Obstet. Gynecol. 1998, 91, 6.
33. Wiseman, H. Expert Opin Investig Drugs. 2000, 9, 1829.
34. Bryant, H.U. Rev. Endocr. Metab. Disord. 2002, 3, 231.
35. Katzenellenbogen, J.A.; Katzenellenbogen, B.S. Chem. Biol. 1996, 3, 529.
36. Mangelsdorf, D.J.; Thummel, C.; Beato, M.; Herrlich, P.; Schutz, G.; Umesono, K.; Blumberg, B.; Kastner, P.; Mark, M.; Chambon, P.; et al. Cell. 1995, 83, 835.
37. McKenna, N.J.; Lanz, R.B.; O'Malley, B.W. Endocr. Rev. 1999, 20, 321.
38. Shibata, H.; Spencer, T.E.; Onate, S.A.; Jenster, G.; Tsai, S.Y.; Tsai, M.J.; O'Malley, B.W. Recent. Prog. Horm. Res. 1997, 52, 141.
39. Nilsson, S.; Makela, S.; Treuter, E.; Tujague, M.; Thomsen, J.; Andersson, G.; Enmark, E.; Pettersson, K.; Warner, M.; Gustafsson, J.A. Physiol. Rev. 2001, 81, 1535.
40. Eriksson, M.A.; Hard, T.; Nilsson, L. Biophys. J. 1995, 68, 402.
41. Enmark, E.; Pelto-Huikko, M.; Grandien, K.; Lagercrantz, S.; Lagercrantz, J.; Fried, G.; Nordenskjold, M.; Gustafsson, J.A. J. Clin. Endocrinol. Metab. 1997, 82, 4258.
42. Vanacker, J.M.; Pettersson, K.; Gustafsson, J.A.; Laudet, V. Embo. J. 1999, 18, 4270.
43. Shiau, A.K.; Barstad, D.; Loria, P.M.; Cheng, L.; Kushner, P.J.; Agard, D.A.; Greene, G.L. Cell. 1998, 95, 927.
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. Nature. 1997, 389, 753.
45. Pike, A.C.; Brzozowski, A.M.; Hubbard, R.E.; Bonn, T.; Thorsell, A.G.; Engstrom, O.; Ljunggren, J.; Gustafsson, J.A.: Carlquist, M. Embo. J. 1999, 18, 4608.
46. Paech, K.; Webb, P.; Kuiper, G.G.; Nilsson, S.; Gustafsson, J.; Kushner, P.J.; Scanlan, T.S. Science. 1997, 277, 1508.
47. 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.A. Endocrinology. 1998, 139, 4252.
48. Barkhem, T.; Carlsson, B.; Nilsson, Y.; Enmark, E.; Gustafsson, J.; Nilsson, S. Mol. Pharmacol. 1998, 54, 105.
49. Meyers, M.J.; Sun, J.; Carlson, K.E., Katzenellenbogen, B.S.; Katzenellenbogen, J.A. J. Med. Chem. 1999, 42, 2456.
50. Sun, J.; Meyers, M.J.; Fink, B.E.; Rajendran, R.; Katzenellenbogen, J.A.; Katzenellenbogen, B.S. Endocrinology. 1999, 140, 800.
51. Santell, R.C.; Chang, Y.C.; Nair, M.G.; Helferich, W.G. J. Nutr. 1997, 127, 263.
52. Glazier, M.G.; Bowman, M.A. Arch. Intern. Med. 2001, 161, 1161.
53. Shiau, A.K.; Barstad, D.; Radek, J.T.; Meyers, M.J.; Nettles, K.W.; Katzenellenbogen, B.S.; Katzenellenbogen, J.A.; Agard, D.A.; Greene, G.L. Nat. Struct. Biol. 2002, 9, 359.
54. Zand, R.S.; Jenkins, D.J.; Diamandis, E.P. Breast. Cancer. Res. Treat. 2000, 62, 35.
55. Stahl, S.; Chun, T.Y.; Gray, W.G. Toxicol. Appl. Pharmacol. 1998, 152, 41.
56. Collins, B.M.; McLachlan, J.A.; Arnold, S.F. Steroids. 1997, 62, 365.
57. Miksicek, R.J. Proc. Soc. Exp. Biol. Med. 1995, 208, 44.
58. Le Bail, J.C.; Varnat, F.; Nicolas, J.C.; Habrioux, G. Cancer. Lett. 1998, 130, 209.
59. Tamir, S.; Eizenberg, M.; Somjen, D.; Stern, N.; Shelach, R., Kaye, A.; Vaya, J. Cancer. Res. 2000, 60, 5704.
60. 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. Chem. Res. Toxicol. 2001, 14, 280.
61. Branham, W.S.; Dial, S.L.; Moland, C.L.; Hass, B.S.; Blair, R.M.; Fang, H.; Shi, L.; Tong, W.; Perkins, R.G.; Sheehan, D.M. J. Nutr. 2002, 132, 658.
62. Blair, R.M.; Fang, H.; Branham, W.S.; Hass, B.S.; Dial, S.L.; Moland, C.L.; Tong, W.; Shi, L.; Perkins, R.; Sheehan, D.M. Toxicol. Sci. 2000, 54, 138.
63. Fang, H.; Tong, W.; Perkins, R.; Soto, A.M.; Prechtl, N.V.; Sheehan, D.M. Environ. Health. Perspect. 2000, 108, 723.
64. Wiese, T.E.; Polin, L.A.: Palomino, E.; Brooks, S.C. J. Med Chem. 1997, 40, 3659.
65. Tamir, S.; Eizenberg, M.; Somjen, D.; Izrael, S.; Vaya, J. J Steroid. Biochem. Mol. Biol. 2001, 78, 291.
66. Shi, L.M.; Fang, H.; Tong, W.; Wu, J.; Perkins, R.; Blair, R.M.; Branham, W.S.; Dial, S.L.; Moland, C.L.; Sheehan, D.M. J. Chem. Inf. Comput. Sci. 2001, 41, 186.
67. Singh, A.K. Cancer. Invest. 2001, 19, 201.
68. Zacharewski, T. Environ. Health. Perspect. 1998, 106, 577.
69. Offir, R.; Tamir, S.; Khatib, S.; Vaya, J. J. of. Molecular. Neuroscience. 2003, 20, 135.
70. Anstead, G.M.; Carlson, K.E.; Katzenellenbogen, J.A. Steroids. 1997, 62, 268.
71. Egner, U.; Heinrich, N.; Ruff, M.; Gangloff, M.; Mueller-Fahrnow, A.; Wurtz, J.M. Med. Res. Rev. 2001, 21, 523.
72. Paige, L.A.; Christensen, D.J.; Gron, H.; Norris, J.D.; Gottlin, E.B.; Padilla, K.M.; Chang, C.Y.; Ballas, L.M.; Hamilton, P.T.; McDonnell, D.P.; Fowlkes, D.M. Proc. Natl. Acad. Sci. USA. 1999, 96, 3999.
73. Vaya, J.; Belinky, P.A.; Aviram, M. Free Radic Biol Med. 1997, 23, 302.
74. Belinky, P.A.; Aviram, M.; Mahmood, S.; Vaya, J. Free. Radic. Biol. Med. 1998, 24, 1419.
75. Kitaoka, M.; Kadokawa, H.; Sugano, M.; Ichikawa, K.; Taki, M.; Takaishi, S.; Iijima, Y.; Tsutsumi, S.; Boriboon, M.; Akiyama, T. Planta. Med. 1998, 64, 511.
76. Somjen, D.; Amir-Zaltsman, Y.; Gayer, B.; Kulik, T.; Knoll, E.; Stern, N.; Lu, L.J.; Toldo, L.; Kohen, F. J. Endocrinol. 2002, 173, 415.
77. Kohen, F.; Gayer, B.; Amir-Zaltsman, Y.; Ben-Hur, H.; Thomas, E.; Lu, L.J. Nutr. Cancer. 1999, 35, 96.
78. Bradbury S, Kamenska V, Schmieder P, Ankley G, Mekenyan O. A Toxicol. Sci. 2000, 58, 253.