Soy Isoflavones

Nutritional Oncology, Second Edition

Volumn , Issue , 2006, Pages 559-571

  Barnes, Stephen ^a   Prasain, Jeevan ^a   D'Alessandro, Tracy ^a   Wang, Chao Cheng ^a   Zhang, Huang Ge ^a   Kim, Helen ^a  

^a University of Alabama at Birmingham   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34247381305     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-012088393-6/50088-9     Document Type: Chapter

References (84)

1. T. Akiyama, J. Ishida, S. Nakagawa, H. Ogawara, S. Watanabe, N. Itoh, M. Shibuya and Y. Fukami (1987) Genistein, a specific inhibitor of tyrosine-specific protein kinases. J Biol Chem 262 5592-5595.
2. T. Akiyama and H. Ogawara (1991) Use and specificity of genistein as inhibitor of protein-tyrosine kinases. Meth Enzymol 201 362-370.
3. C.D. Allred, K.F. Allred, Y.H. Ju, S.M. Virant and W.G. Helferich (2001) Soy diets containing varying amounts of genistein stimulate growth of oestrogen-dependent (MCF-7) tumors in a dose-dependent manner. Cancer Res 61 5045-5050.
4. C.D. Allred, Y.H. Ju, K.F. Allred, J. Chang and W.G. Helferich (2001) Dietary genistein stimulates growth of oestrogen-dependent breast cancer tumors similar to that observed with genistein. Carcinogenesis 22 1667-1673.
5. J.W. Anderson, B.M. Johnstone and M.E. Cook-Newell (1995) Meta-analysis of the effects of soy protein intake on serum lipids. N Engl J Med 333 276-282.
6. A.B. Awad, A. Downie, C.S. Fink and U. Kim (2000) Dietary phytosterol inhibits the growth and metastasis of MDA-MB-231 human breast cancer cells grown in SCID mice. Anticancer Res 20 821-824.
7. S. Barnes, C. Grubbs, K.D.R. Setchell and J. Carlson (1990) Soybeans inhibit mammary tumors in models of breast cancer. Prog Clin Biol Res 347 239-253.
8. S. Barnes, T.G. Peterson, C. Grubbs and K.D.R. Setchell (1994) Potential role of dietary isoflavones in the prevention of cancer. Adv Exp Med Biol 354 135-147.
9. S. Barnes, M. Kirk and L. Coward (1994) Isoflavones and their conjugates in soy foods: extraction conditions and analysis by HPLC-mass spectrometry. J Agric Food Chem 42 2466-2474.
10. S. Barnes, J. Xu, M. Smith and M. Kirk (2001) Lack of evidence for the intestinal absorption of isoflavone β-glucosides in the intact rat. Paper presented at the 221st National Meeting of the American Chemical Society San Diego, CA
11. S. Barnes, C-C. Wang, M. Kirk, M. Smith-Johnson, L. Coward, N.C. Barnes, G. Vance and B. Boersma (2002) HPLC-mass spectrometry of isoflavonoids in soy and the American groundnut, Apios americana. Adv Exp Med Biol 505 77-88.
12. S. Barnes, H.G. Zhang, C.R. Liu, P. Liu, S.H. Yu and J.K. Prasain (2005) Polyphenols inhibit breast cancer cell exosome regulation of T cell and natural killer cell response. FASEB J 19 A1461.
13. S. Barnes and J.K. Prasain (2005) Current progress in the use of traditional medicines and nutraceuticals. Current Opin Plant Biol 8 324-328.
14. T. Bayer, T. Colnot and W. Dekant (2001) Disposition and biotransformation of the estrogenic isoflavone daidzein in rats. Toxicol Sci 62 205-211.
15. B.J. Boersma, R.P. Patel, M. Kirk, V.M. Darley-Usmar and S. Barnes (1999) Chlorination and nitration of soy isoflavones. Arch Biochem Biophys 368 265-275.
16. B.J. Boersma, T. D'Alessandro, M.R. Benton, M. Kirk, L.S. Wilson, J. Prasain, N.P. Botting, S. Barnes, V.M. Darley-Usmar and R.P. Patel (2003) Neutrophil myeloperoxidase chlorinates soy isoflavones and enhances their antioxidant properties. Free Radic Biol Med 35 1417-1430.
17. F. Cheng, D. Gabrilovich and E.M. Sotomayor (2004) Immune tolerance in breast cancer. Breast Dis 20 93-103.
18. N.G. Coldham, L.C. Howells, A. Santi, C. Montesissa, C. Langlais, L.J. King, D.D. Macpherson and M.J. Sauer (1999) Biotransformation of genistein in the rat: elucidation of metabolite structure by product ion mass fragmentology. J Steroid Biochem Mol Biol 70 169-184.
19. L. Coward, N.C. Barnes, K.D.R. Setchell and S. Barnes (1993) The antitumor isoflavones, genistein and daidzein, in soybean foods of American and Asian diets. J Agric Food Chem 41 1961-1967.
20. T. D'Alessandro, J. Prasain, N.P. Botting, R. Moore, V.M. Darley-Usmar, R.P. Patel and S. Barnes (2003) Polyphenols, inflammatory response, and cancer prevention: chlorination of isoflavones by human neutrophils. J Nutr 133 3773S-3777S.
21. T.L. D'Alessandro, R. Moore, N. Botting and S. Barnes (2005) In vivo glucuronidation of daidzein and its chlorinated isomers. FASEB J 19 A449.
22. J.N. Davis, O. Kucuk and F.H. Sarkar (1999) Genistein inhibits NF-kappa B activation in prostate cancer cells. Nutr Cancer 35 167-174.
23. J.N. Davis, O. Kucuk, Z. Djuric and F.H. Sarkar (2001) Soy isoflavone supplementation in healthy men prevents NF-kappa B activation by TNF-alpha in blood lymphocytes. Free Radic Biol Med 30 1293-1302.
24. A.J. Day, F.J. Canada, J.C. Diaz, P.A. Kroon, R. McLauchlan, C.B. Faulds, G.W. Plumb, M.R. Morgan and G. Williamson (2000) Dietary flavonoid and isoflavone glycosides are hydrolyzed by the lactase site of lactase phlorizin hydrolase. FEBS Lett 468 166-170.
25. D. Dimitrakoudis, M. Vranic and A. Klip (1992) Effects of hyperglycemia on glucose transporters of the muscle: use of the renal glucose reabsorption inhibitor phlorizin to control glycemia. J Am Soc Nephrol 3 1078-1091.
26. R. Doll and R. Peto (1981) The causes of cancer: quantitative estimates of avoidable risks of cancer in the United States today. J Natl Cancer Inst 66 1291-1308.
27. H. Esaki, S. Kawakishi, Y. Morimitsu and T. Osawa (1999) New potent antioxidative o-dihydroxyisoflavones in fermented Japanese soybean products. Biosci Biotechnol Biochem 63 1637-1639.
28. S. Foster (1994) Kudzu root monograph. Q Rev Nat Med Winter 303-308.
29. W.A. Fritz, L. Coward, J. Wang and C.A. Lamartiniere (1998) Dietary genistein: perinatal mammary cancer prevention, bioavailability and toxicity testing in the rat. Carcinogenesis 19 2151-2158.
30. A.F. Galvez, N. Chen, J. Macasieb and B.O. de Lumen (2001) Chemopreventive property of a soybean peptide (lunasin) that binds to deacetylated histones and inhibits acetylation. Cancer Res 61 7473-7478.
31. C.J. Grubbs, D.R. Farnell, D.L. Hill and K.C. McDonough (1985) Chemoprevention of N-nitroso-N-methylurea-induced mammary cancers by pretreatment with 17β-estradiol and progesterone. J Natl Cancer Inst 74 927-931.
32. R.M. Hamilton and K.K. Carroll (1976) Plasma cholesterol levels in rabbits fed low fat, low cholesterol diets: effects of dietary protein, carbohydrates and fibre from different sources. Atherosclerosis 24 47-62.
33. A.S. Hamilton and T.M. Mack (2003) Puberty and genetic susceptibility to breast cancer in a case-control study in twins. N Engl J Med 348 2313-2322.
34. E.J. Hawrylewicz, J. Zapata and W.H. Blair (1995) Soy and experimental cancer: animal studies. J Nutr 125(3 Suppl), 698S-708S.
35. S.L. Hazen and J.W. Heinecke (1997) 3-Chlorotyrosine, a specific marker of myeloperoxidase-catalyzed oxidation, is markedly elevated in low-density lipoprotein isolated from human atherosclerotic intima. J Clin Invest 99 2075-2081.
36. T.E. Hedlund, P.D. Maroni, P.G. Ferucci, R. Dayton, S. Barnes, R. Jones, D.R. Moore, L.G. Ogden, K. Wähälä, H.M. Sackett and K.J. Gray (2005) Long-term dietary habits influence soy isoflavone metabolism in Caucasian men: selective accumulation of isoflavonoids within prostatic fluid. J Nutr 135 1400-1406.
37. L. Hilakivi-Clarke, E. Cho, I. Onojafe, M. Raygada and R. Clarke (1999) Maternal exposure to genistein during pregnancy increases carcinogen-induced mammary tumorigenesis in female rat offspring. Oncol Rep 6 1089-1095.
38. L. Hilakivi-Clarke, E. Cho, S. deAssis, S. Olivo, E. Ealley, K.B. Bouker, J.N. Welch, G. Khan, R. Clarke and A. Cabanes (2001) Maternal and prepubertal diet, mammary development and breast cancer risk. J Nutr 131 154S-157S.
39. P.L. Horn-Ross, S. Barnes, M. Kirk, L. Coward, J. Parsonnet and R.A. Hiatt (1997) Urinary phytoestrogen levels in young women from a multiethnic population. Cancer Epidemiol Biomark Prev 6 339-345.
40. P.L. Horn-Ross, S. Barnes, M. Lee, L. Coward, E. Mandel, J. Koo, E.M. John and M. Smith (2000) Assessing phytoestrogen exposure in epidemiologic studies: development of a database (United States). Cancer Causes Control 11 289-298.
41. C.Y. Hsieh, R.C. Santell, S.Z. Haslam and W.G. Helferich (1998) Oestrogenic effects of genistein on the growth of oestrogen receptor-positive human breast cancer (MCF-7) cells in vitro and in vivo. Cancer Res 58 3833-3838.
42. T. Hymowitz (1990) Soybeans: The success story. J. Janick, J.E. Simon (Eds) Advances in New Crops Portland, OR: Timber Press 159-163.
43. H. Ischiropoulos, L. Zhu, J. Chen, M. Tsai, J.C. Martin, C.D. Smith and J.S. Beckman (1992) Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Arch Biochem Biophys 298 431-437.
44. Y.H. Ju, C.D. Allred, K.F. Allred, K.L. Karko, D.R. Doerge and W.G. Helferich (2001) Physiological concentrations of dietary genistein dose-dependently stimulate growth of oestrogen-dependent human breast cancer (MCF-7) tumors implanted in athymic nude mice. J Nutr 131 2957-2962.
45. Y.H. Ju, D.R. Doerge, K.F. Allred, C.D. Allred and W.G. Helferich (2002) Dietary genistein negates the inhibitory effect of tamoxifen on the growth of estrogen-dependent human breast cancer (MCF-7) cells implanted in athymic mice. Cancer Res 62 2474-2477.
46. Y.H. Ju, L.M. Clausen, K.F. Allred, A.L. Almada and W.G. Helferich (2004) Beta-sitosterol, beta-sitosterol glucoside, and a mixture of betasitosterol and beta-sitosterol glucose modulate the growth of estrogen-responsive breast cancer cells in vitro and in ovariectomized athymic mice. J Nutr 134 1145-1151.
47. G.E. Kelly, G.E. Joannou, A.Y. Reeder, C. Nelson and M.A. Waring (1995) The variable metabolic response to dietary isoflavones in humans. Proc Soc Exp Biol Med 208 40-43.
48. A.R. Kennedy (1998) The Bowman-Birk inhibitor from soybeans as an anticarcinogenic agent. Am J Clin Nutr 68(6 Suppl), 1406S-1412S.
49. H. Kim, T.G. Peterson and S. Barnes (1998) Mechanism of action of the soy isoflavone genistein: emerging role of its effects through transforming growth factor beta signaling pathways. Am J Clin Nutr 68 1418S-1425S.
50. H. Kim, P. Hall, M. Smith, M. Kirk, J.K. Prasain, S. Barnes and C. Grubbs (2004) Chemoprevention by grape seed extract and genistein in carcinogen-induced mammary cancer in rats is diet-dependent. J Nutr 134 3445S-3552S.
51. C.J. Kirk, R.M. Harris, D.M. Wood, R.H. Waring and P.J. Hughes (2001) Do dietary phytoestrogens influence susceptibility to hormone-dependent cancer by disrupting the metabolism of endogenous oestrogens? Biochem Soc Trans 29 209-216.
52. S. Kudou, Y. Fleury, D. Welti, D. Magnolato, T. Uchida, K. Kitamura and K. Okubo (1991) Malonyl isoflavone glycosides in soybean seeds (Glycine max Merrill). Agric Biol Chem 55 2227-2233.
53. S.E. Kulling, D.M. Honig, T.J. Simat and M. Metzler (2000) Oxidative in vitro metabolism of the soy phytoestrogens daidzein and genistein. J Agric Food Chem 48 4963-4972.
54. S.E. Kulling and L. Lehmann (2002) Metzler M. Oxidative metabolism and genotoxic potential of major isoflavone phytoesrrogens. J Chromatogr B Anal Technol Biomed Life Sci 777 211-218.
55. C.A. Lamartiniere, J. Moore, M. Holland and S. Barnes (1995) Genistein and chemoprevention of breast cancer. Proc Soc Exp Biol Med 208 120-123.
56. C.A. Lamartiniere, J.B. Moore, N.A. Brown, R. Thompson, M.J. Hardin and S. Barnes (1995) Genistein suppresses mammary cancer in rats. Carcinogenesis 16 2833-2840.
57. C.A. Lamartiniere, M.S. Cotroneo, W.A. Fritz, J. Wang, R. Mentor-Marcel and A. Elgavish (2002) Genistein chemoprevention: timing and mechanisms of action in murine mammary and prostate. J Nutr 132 552S-558S.
58. C.R. Liu, S.H. Yu, W.E. Grizzle, R.P. Kimberly, J.H. Wang, P. Liu, L.M. Zhang, H.C. Hsu, S. Barnes, J.D. Mountz and H.G. Zhang (2005) Breast tumor exosomes promote tumor growth by immune suppression of NK cells. FASEB J 19 A39-A40.
59. S. Makela, M. Poutanen, J. Lehtimaki, M.L. Kostian, R. Santti and R. Vihko (1995) Estrogen-specific 17 beta-hydroxysteroid oxidoreductase type 1 (E.C. 1.1.1.62) as a possible target for the action of phytoestrogens. Proc Soc Exp Biol Med 208 51-59.
60. J. Markovits, C. Linassier, P. Fosse, J. Couprie, J. Pierre, A. Jacquemin-Sablon, J.M. Saucier, J.B. Le Pecq and A.K. Larsen (1989) Inhibitory effects of the tyrosine kinase inhibitor genistein on mammalian DNA topoisomerase II. Cancer Res 49 5111-5117.
61. M.C. Pagliacci, M. Smacchia, G. Migliorati, F. Grignani, C. Riccardi and I. Nicoletti (1994) Growth-inhibitory effects of the natural phytooestrogen genistein in MCF-7 human breast cancer cells. Eur J Cancer 30A 1675-1682.
62. T.G. Peterson, L. Coward, M. Kirk, C.N. Falany and S. Barnes (1996) Isoflavones and breast epithelial cell growth: the importance of genistein and biochanin A metabolism in the breast. Carcinogenesis 17 1861-1869.
63. T.G. Peterson, G-P. Ji, M. Kirk, L. Coward, C.N. Falany and S. Barnes (1998) Metabolism of the isoflavones genistein and biochanin A in human breast cancer cell lines. Am J Clin Nutr 68 1505-1511.
64. J.K. Prasain, K. Jones, M. Kirk, L. Wilson, M. Smith-Johnson, C.M. Weaver and S. Barnes (2003) Identification and quantitation of isoflavonoids in Kudzu dietary supplements by HPLC and electrospray ionization tanden mass spectrometry. J Agric Food Chem 51 4213-4218.
65. J.K. Prasain, K. Jones, N. Brissie, D.R. Moore II, J.M. Wyss and S. Barnes (2004) Identification of puerarin and its metabolites in rats by liquid chromatography-tanden mass spectrometry. J Agric Food Chem 52 3708-3712.
66. G. Schultz (1965) Isoflavone glucoside formononetin-7-glucoside and biochanin A-7-glucoside in Trifolium pratense L. Naturwissenschaften 52 517.
67. P.M. Schwartsburd (2004) Age-promoted creation of a pro-cancer microenvironment by inflammation: pathogenesis of dyscoordinated feedback control. Mech Age Develop 125 581-590.
68. J. Sfakianos, L. Coward, M. Kirk and S. Barnes (1997) Intestinal uptake and biliary excretion of the isoflavone genistein in the rat. J Nutr 127 1260-1268.
69. A.M. Shamsuddin, I. Vucenik and K.E. Cole (1997) IP6: a novel anticancer agent. Life Sci 61 343-354.
70. Z.M. Shao, J. Wu, Z.Z. Shen and S.H. Barsky (1998) Genistein exerts multiple suppressive effects on human breast carcinoma cells. Cancer Res 58 4851-4857.
71. Z.M. Shao, Z.Z. Shen, J.A. Fontana and S.H. Barsky (2000) Genistein's “ER-dependent and independent” action are mediated through ER pathways in ER-positive breast carcinoma cell lines. Anticancer Res 20 2409-2416.
72. S.R. Shelnutt, C.O. Cimino, P.A. Wiggins, M.J. Ronis and T.M. Badger (2002) Pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein in men and women after consumption of a soy beverage. Am J Clin Nutr 76 588-594.
73. X.O. Shu, F. Jin, Q. Dai, W. Wen, J.D. Potter, L.H. Kushi, Z. Ruan, Y.T. Gao and W. Zheng (2001) Soyfood intake during adolescence and subsequent risk of breast cancer among Chinese women. Cancer Epidemiol Biomark Prev 10 483-488.
74. F.J. Simoons (1978) The geographic hypothesis and lactose malabsorption: a weighing of the evidence. Am J Dig Dis 23 963-980.
75. C.R. Sirtori, E. Agradi, F. Conti, O. Mantero and E. Gatti (1977) Soybean-protein diet in the treatment of type-II hyperlipoproteinaemia. Lancet 1(8006), 275-277.
76. Y.J. Surh (2003) Cancer chemoprevention with dietary phytochemicals. Nature Rev Cancer 3 768-780.
77. W. Troll, R. Wiesner, C.J. Shellabarger, S. Holtzman and J.P. Stone (1980) Soybean diet lowers breast tumor incidence in irradiated rats. Carcinogenesis 1 469-472.
78. U.S. Department of Agriculture, Agricultural Research Service (2002) USDA-Iowa State University Database on the Isoflavone Content of Foods, Release 1.3-2002 http://www.nal.usda.gov/fnic/foodcomp/Data/isoflav/isoflav.html Available at the Nutrient Data Laboratory web site
79. D. Urban, W. Irwin, M. Kirk, M.A. Markiewicz, R. Myers, M. Smith, H. Weiss, W.E. Grizzle and S. Barnes (2001) The effect of isolated soy protein on plasma biomarkers in elderly men with elevated serum prostate specific antigen. J Urol 165 294-300.
80. H. Wei, L. Wei, K. Frankel, R. Bowen and S. Barnes (1993) Inhibition of tumor promoter induced hydrogen peroxide formation in vitro and in vivo by genistein. Nutr Cancer 20 1-12.
81. W.C. Willett, M.J. Stampfer, G.A. Colditz, B.A. Rosner, C.H. Hennekens and F.E. Speizer (1987) Dietary fat and the risk of breast cancer. N Engl J Med 316 22-28.
82. A.H. Wu, P. Wan, J. Hankin, C-C. Tseng, M.C. Yu and M.C. Pike (2002) Adolescent and adult soy intake and risk of breast cancer in Asian-Americans. Carcinogenesis 23 1491-1496.
83. X. Xu, H.J. Wang, P.A. Murphy, L. Cook and S. Hendrich (1994) Daidzein is a more bioavailable soymilk isoflavone than is genistein in adult women. J Nutr 124 825-832.
84. D.T. Zava and G. Duwe (1997) Estrogenic and antiproliferative properties of genistein and other flavonoids in human breast cancer cells in vitro. Nutr Cancer 27 31-40.