Isoflavones from soybeans and soy foods

Functional Foods: Biochemical and Processing Aspects

Volumn 2, Issue , 2016, Pages 39-69

  Chang, Sam K C ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOFLAVONES; SOY FOODS;

FLAVONOIDS;

EID: 85051311032     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (142)

1. Akiyama, T., Ishida, J., Nakagawa, S., Ogawara, H., Watanabe, S., Itoh, N., Shibuya, M. and Fukami, Y. 1987. Genistein: a specific inhibitor of tyrosine-specific protein kinase. J. Biol. Chem. 262:5592-5595.
2. Aldercreutz, H. 1998. Epidemiology of phytoestrogens. Baillieres Clin. Endocrinol. Metab. 12:605-623.
3. Aldercreutz, H. and Mazur, W. 1997. Phyto-oestrogens and western diseases. Ann. Med.29:95-120.
4. Aldercreutz, H., Honjo, H., Higashi, A., Fotsis, T., Hamalainen, E., Hasegawa, T. and Okadia, H. 1991. Urinary excretion of lignans and isoflavonoid phytoestrogens in Japanese men and women consuming a traditional Japanese diet. Am. J. Clin. Nutr. 54:1093-1100.
5. Anderson, J.J.B. and Carner, S.C. 1997. The effects of phytoestrogens on bone. Nutr. Res.17:1617-1632.
6. Anderson J.W., Diwadkar, V.A. and Bridges, S.R. 1998. Selective effects of different antioxidants on oxidation of lipoproteins from rats. Proc. Soc. Exp. Biol. Med.218:376-381.
7. Anthony, M.S., Clarkson, T.B. and Williams, J.K. 1998. Effects of soy isoflavones on atherosclerosis: potential mechanisms. Am J. Clin. Nutr. 68(suppl):1390S-1393S.
8. Aussenac, T., Lacombe, S., and Dayde, J. 1998. Quantification of isoflavones by capillary zone electrophoresis in soybean seeds: effects of variety and environment. Am. J. Clin. Nutr. 68(suppl):1480S-1485S.
9. Barnes, S., Kirk, M., and Coward, L. 1994. Isoflavones and their conjugates in soy foods: extraction conditions and analysis by HPLC-mass spectrometry. J. Agric. Food Chem.42:2466-2474.
10. Barnes, S., Coward, L., Kirk, M., and Sfakianos, J. 1998. HPLC-mass spectrometry analysis of isoflavones. Proc. Soc. Exp. Biol. Med. 217:254-262.
11. Bennetts, A.W., Underwood, E.J., and Shier, F.L. 1946. A specific breeding problem of sheep on subterranean clover pastures in Western Australia. Aust. J. Agric. Res. 22:131-138.
12. Bingham, S.A., Atkinson, C., Liggins, J., Bluck, L., and Coward, A. 1998. Phytoestrogens: Where are we now? Br. J. Nutr. 79:393-406.
13. Bryan, B.A. and Allred, M.C. 1998. Aglycone isoflavone enriched vegetable protein extract and protein material and high genistein and daidzein content materials and process for producing the same. US patent 5,726,034. March 10, 1998.
14. Bryan, B.A. and Guevara, B.F. 1999. Isoflavone-rich protein isolate and process for producing. US patent 5,994,508. November 30, 1999.
15. Bryan, B.A., Allred, M.C., and Roussey, M.A. 1998. Two-step conversion of vegetable protein isoflavone conjugates to aglycones. US patent 5,827,682. October 27, 1998.
16. Cai, Q. and Wei, H. 1996. Effect of dietary genistein on antioxidant enzyme activities in SENCAR mice. Nutr. Cancer. 25:1-7.
17. Chaihorsky, A. 1997. Process for obtaining an isoflavone concentrate from a soybean extract. US patent 5,670,632. September 23, 1997.
18. Chandra, A. and Nair, M. 1996. Supercritical carbon dioxide extraction of daidzein and genistein from soybean products. Phytochem. Anal. 7:259-262.
19. Clarkson, T.B., Jr., Anthony, M.S., Pan, Y., Adams, M.R., and Waggle, D.H. 1999. Method for inhibiting the development of Alzheimer's disease and related dementias and for preserving cognitive function. US patent 5,952,374. September 14, 1999.
20. Cline, J.M. and Hughes, C.L. Jr., 1998. Phytochemicals for the prevention of breast and endometrial cancer. In Biological and Hormonal Therapies of Cancer. Eds. K.A. Foon and H.B. Muss. Boston, MA: Kluwer Academic Publishers.
21. Coward, L., Barnes, N.C., Setchell, K.D.R., and Barnes, S. 1993. Genistein, daidzein, and their B-glycoside conjugates: antitumor isoflavones in soybean foods from American and Asian diets. J. Agric. Food. Chem. 41:1961-1967.
22. Coward, L., Smith, M., Kirk, M., and Barnes, S. 1998a. Chemical modification of isflavones in soy foods during cooking and processing. Am. J. Clin. Nutr. 68(suppl):1486S-1491S.
23. Coward, L., Smith, M., Kirk, M., Barnes, S., Messina, M., and Erdman, J.W. 1998b. The role of soy in preventing and treating chronic disease. Am. J. Clin. Nutr. 68(suppl):1486-1491.
24. Crank, D.L. and Kerr, P.S. 1999. Isoflavone-enriched soy product and method for its manufacture. US patent 5,858,449. January 12, 1999.
25. Day, C.E. 1999. Genistin-enriched fraction from soy meal. US patent 5,932,221. August 3, 1999.
26. Dewick, P.M. 1994. Isoflavonoids. In The Flavonoids: Advances since 1986. Ed. J.B. Harborne, New York, NY: Chapman-Hall, pp. 117-238.
27. Eldridge, A.C. 1982a. Determination of isoflavones in soybean flours, protein concentrate and isolates. J. Agric. Food Chem. 30:353-355.
28. Eldridge, A.C. 1982b. High performance liquid chromatography separation of soybean isoflavones and their glycosides. J. Chromatogr. 234:494-496.
29. Eldridge, A.C. and Kwolek, F. 1983. Soybean isoflavones: effect of environment and variety on composition. J. Agric. Food Chem.331:394-396.
30. Eldridge, A.C., Kalbrener, J.E., Moser, H.A., Honig, D.H., Rackis, J.J., and Wolf, W.J. 1971. Laboratory evaluation of hexane:alcohol azeotrope-extracted soybean flakes as a source for bland protein isolates. Cereal Chem.48:644-646.
31. Esaki, H., Onozaki, H., Kawakishi, S., and Osawa, T. 1996. New antioxidant isolated from tempeh. J. Agric. Food Chem.44:696-700.
32. Esaki, H., Watanabe, R., Onozaki, H., Kawakishi, S., and Osawa, T. 1999. Formation mechanism for potent antioxidative o-dihydroxyisoflavones in soybeans fermented with Aspergillus saitoi . Biosci. Biotech. Biochem.63:851-858.
33. Farmakalidis, E. and Murphy, P. 1985. Isolation of 6 ″-O-acetylgenistin and 6 ″-O-acetyldaidzin from toasted defatted soy flakes. J. Agric. Food Chem.33:385-389.
34. Federal Register. October 26, 1999. 64SR 57699: 21CFR Part 101. Food labeling: Health Claims; Soy Protein and Coronary Heart Disease; Final Rule.
35. Fenner, G.P. 1996. Low-temperature treatment of soybean (Glycine max) isoflavonoid aglycone extracts improves gas chromatographic resolution. J. Agric. Food Chem.44:3727-3729.
36. Fleiszig, S.M.J. and Evans, D.J. 1999. Methods for inhibiting bacterial cytotoxicity. US patent 5,948,815. September 7, 1999.
37. Fleury, Y., Welti, D.H., Philippossian, G., and Magnolato, D. 1992. Soybean (malonyl) isoflavones: characterization and antioxidant properties. ACS Symp. Ser.507:98-113.
38. Fotsis, T., Pepper, M., Adlercreutz, H., Fleischman, G., Hase, T., Montesano, R., and Schweigerer, L. 1993. Genistein, a dietary-derived inhibitor of in vitro angiogensis. Proc. Natl. Acad. Sci. USA90:2690-2694.
39. Franke, A.A., Custer, L.J., Cerna, C.M., and Narala, K.K. 1994. Quantitation of phytoestrogens in legumes by HPLC. J. Agric. Food Chem.42:1905-1913.
40. Franke, A.A., Custer, L.J., Cerna, C.M., and Narala, K.K. 1995. Rapid HPLC analysis of dietary phytoestrogens from legumes and from human urine. Proc. Soc. Exp. Biol. Med.208:18-26.
41. Franke, A.A., Custer, L.J., Wang, W., and Shi, C.Y. 1998. HPLC analysis of isoflavonoids and other phenolic agents from foods and human fluids. Proc. Soc. Exp. Biol. Med.217:263-273.
42. Fukutake, M., Takahashi, M., Ishida, K., Kawamura, H., Sugimura, T., and Wakabayashi, K. 1996. Quantification of genistein and genistin in soybeans and soybean products. Food Chem. Toxicol. 34: 457-461.
43. Griffiths, K., Denis, L., Turkes, A., and Morton, M.S. 1998. Phytoestrogens and diseases of the prostate gland. Bailliere Clin. Endocrinol. Metab. 12:625-647.
44. Gugger, E.T. and Dueppen, D.G. 1997. Production of isoflavone enriched fractions from soy protein extracts. US patent 5,702,752. December 30, 1997.
45. Gugger, E.T. and Dueppen, D.G. 1998. Production of isoflavone enriched fractions from soy protein extracts. US patent 5,792,503. August 11, 1998.
46. Gyorgy, P., Murata, K., and Ikehata, H. 1964. Antioxidants isolated from fermented soybeans (tempeh). Nature. 203:870-871.
47. Ha, E.Y.W., Morr, C.V., and Seo, A. 1992. Isoflavone aglycone and volatile organic compounds in soybeans: effects of soaking treatments. J. Food Sci. 57:414-417, 426.
48. Hahlbrock, K. and Grisebach, H. 1975. Biosynthesis of flavonoids. Chapter 16. In The Flavonoids. Eds. J.B. Harborne, T.J. Mabry, and H. Mabry, London, UK: Chapman & Hall, pp. 866-915.
49. Heller, W. and Forkmann, G. 1988. Biosynthesis. Chapter 11. In The Flavonoids: Advances in Research since 1980. Ed. J.B. Harborne, New York, NY: Chapman & Hall, pp. 399-425.
50. Hessler, P.E., Larsen, P.E., Constantinou, A.I., Schram, K.H., and Weber, J.M. 1997. Isolation of isoflavones from soy-based fermentations of the erythromycin-producing bacterium Saccharopolyspora erythraea. Applied Microbiol. Biotech. 47:398-404.
51. Hoeck, J.A., Fehr, W.R., Murphy, P.A., and Welke, G.A. 2000. Influence of genotype and environment on isoflavone contents of soybean. Crop Sci. 40:48-51.
52. Humfrey, C.D.N. 1998. Phytoestrogens and human health effects: weighing up the current evidence. Nat. Toxins. 6:51-59.
53. Hwang, T.C., Smith, A.L., Konig, P., Clarke, L.L., Price, E.M., and Cohn, L.A. 1999. Genistein for the treatment of cystic fibrosis. US patent 5,948,814. September 7, 1999.
54. Iwamura, J. 1984. Process for isolating saponins and flavonoids from leguminous plants. US patent 4,428,876. January 31, 1984.
55. Jenks, B.H. 1999. Method for inhibiting or reducing the risk of macular degeneration. US patent 6,001,368. December 14, 1999.
56. Johns, P.W., Suh, J.D., Daab-Krzykowski, A., Mazer, T.B., and Mei, F.I. 2000. Process for isolating phytoestrogens from plant protein. US patent 6, 202,471. February 1, 2000.
57. Jones, A.E., Price, K.R., and Fenwick, G.R. 1989. Development and application of a highperformance liquid chromatographic method for the analysis of phytoestrogens. J. Sci. Food. Agric. 46(3):357-364.
58. Kanaoka, S., Uesugi, T., Hirai, K., Toda, T., and Okuhira, T. 1998. Clathrate of isoflavone derivatives and edible composition comprising the same. US patent 5,847,108. December 8, 1998.
59. Kaufman, P.B., Duke, J.A., Brielmann, H., Boik, J., and Hoyt, J.E. 1997. A comprehensive survey of leguminous plants as sources of the isoflavones, genistein and daidzein: implications for human nutrition and health. J. Alternate Complementary Med. 3:7-22.
60. Klus, K. and Barz, W. 1995. Formation of polyhydroxylated isoflavones from the soybean seed isoflavones daizein and glycitein by bacteria isolated from tempe. Arch. Microbiol.164:428-434.
61. Klus, K. and Barz, W. 1998. Formation of polyhydroxylated isoflavones from isoflavones genistein and biochanin A by bacteria isolated from tempe. Phytochemistry47:1045-1048.
62. Klus, K., Boerger-Paperndorf, G., and Barz, W. 1993. Formation of 6,7,4'-trihydroxyisoflavone (factor 2) from soybean seed isoflavones by bacteria isolated from tempe. Phytochemistry 34:979-981.
63. Knight, D.C. and Eden, J.A. 1996. A review of the clinical effects of phytoestrogens. Obstet. Gynecol. 87:897-904.
64. Knight, D.C., Wall, P.L., and Eden, J.A. 1996. A review of phytoestrogens and their effects in relation to menopausal symptoms. Aust. J. Nutr. Diet. 53:5-11.
65. Kudou, S., Fleury, Y., Weiti, D., Magnotato, D., Uchida, T., Kitamura, K. and Okubo, K., 1991. Malonylisoflavone glycosides in soybean seeds. Agric. Biol. Chem. 55:2227-2233.
66. Kurzer, M.S. and Xu, X. 1997. Dietary phytoestrogens. Annu. Rev. Nutr. 17:353-381.
67. Lanzendorfer, G., Stab, F., and Untiedt, S. 1999. Agents acting against hyperactive and hypoactive, deficient skin conditions and manifest dermatitides. US patent 5,952,373. September 14, 1999.
68. Liggins, J., Bluck, L.J., Coward, A., and Bingham, S.A. 1998. Extraction and quantification of daidzein and genistein in food. Anal. Biochem. 264:1-7.
69. Liu, K.S. 1997. Soybeans: Chemistry, Technology and Utilization. New York, NY: Chapman & Hall.
70. Matsuda, S., Miyazaki, T., Matsumoto, Y., Ohba, R., Termoto, Y., Ohta, N., and Ueda, S. 1992. Hydrolysis of isoflavones in soybean cooked syrup by Lactobacillus casei subsp. Rhamnosus IFO 3425. J. Fermentation Bioeng. 74:301-304.
71. Matsuo, M. 1997. In vivo antioxidant activity of okara Koji, a fermented okara, by Aspergillus oryzae. Biosci. Biotech. Biochem. 61:1968-1972.
72. Matsuura, M., Obata, A., and Fukushima, D. 1989. Objectionable flavor of soymilk developed during the soaking of soybeans and its control. J. Food Sci. 54:602-605
73. Matsuura, M., Obata, A., Tobe, K., and Yamaji, N. 1998. Process for obtaining malonyl isoflavone glycosides and obtaining isoflavone glycosides or isoflavone aglycones from malonyl isoflavone glycosides. US patent 5,789,581. August 4, 1998.
74. Mazur, W.M., Duke, J.A., Wahala, K., Rasku, S., and Adlercreutz, H. 1998. Isofalvonoids and lignans in legumes: nutritional and health aspects in humans. Nutr. Biochem.9:193-200.
75. Messina, M. 1997. Soy foods: their role in disease prevention and treatment. In Soybeans: Chemistry, Technology and Utilization. Ed. K.S. Liu, New York, NY: Chapman & Hall, pp. 442-477
76. Messina, M. and Bennink, M. 1998. Soy foods, isoflavones and risk of colonic cancer: a review of the in vitro and in vivo data. Bailliere Clin. Endocrinol. Metab. 12:707-728.
77. Messina, M.J., Persky, V., Setchell, K.D.R., and Barnes, S. 1994. Soy intake and cancer risk: a review of the in vitro and in vivo data. Nutr. Cancer. 21:113-131.
78. Messina, M., Barnes, S., and Setchell, K.D. 1997. Phytoestrogens and breast cancer. Lancet. 350:971-972.
79. Molteni, A., Brizo Molteni, L., and Persky, V. 1995. In vitro hormonal effects of soybean isoflavones. J. Nutr. 125:751S-756S.
80. Murakami, H., Asakawa, T., Tero, J., and Matsushita, S. 1984. Antioxidant stability of tempeh and liberation of isoflavones by fermentation. Agric. Biol. Chem. 48:2971-2975.
81. Murphy, P.A. 1981. Separation of genistin, daidzin, and their aglycones and coumestrol by gradient high-performance liquid chromatogrphy. J. Chromatogr. 211:166-169.
82. Murphy, P.A., Song, T., Buseman, G., Baru, K., Beecher, G.R., Trainer, D., and Holden, J. 1999. Isoflavones in retail and institutional soy foods. J. Agric. Food Chem.47:2697-2704.
83. Naim, M., Gestetner, B., Zilkah, S., Birk, Y., Bondi, A. 1974. Soybean isoflavones. Characterization, determination and antifungal activity. J. Agric. Food Chem. 22:806-810.
84. Naim, M., Gestetner, B., Bondi, A., and Birk, Y. 1976. Antioxidative and antihemolytic activities of soybean isoflavones. J. Agric. Food Chem. 24:1174-1177.
85. Ohta, N., Kuwata, G., Atkhori, H., and Watanabe, T. 1979. Isoflavonoid constituents of soybeans and isolation of a new acetyldaidzin. Agric. Biol. Chem. 43:1415-1418.
86. Okubo, K., Iijima, M., Kobayashi, Y., Yoshikoshi, M., Uchida, T., and Kudou, S. 1992. Components responsible for the undesirable taste of soybean seeds. Biosci. Biotech. Biochem. 56:99-103.
87. Parthasarathi, G. and Fenner, G.P. 1999. Improved method for gas chromatographic analysis of genistein and daizein from soybean (Glycine max) seeds. J. Agric. Food Chem.47:3455-3456.
88. Peterson, G. and Barnes, S. 1991. Genistein inhibition of the growth of human breast cancer cells: independence from estrogen receptors and multi-drug resistance gene. Biochem. Biophys. Res. Commun. 179:661-667.
89. Pettersson, H. and Kiessling, K.H. 1984. Liquid chromatography determination of the plant estrogens coumestrol and isoflavones in animal feed. J. Assoc. Off. Anal. Chem.67:503-506.
90. Potter, S.M., Henley, E.C., and Waggle, D.H. 1999. Method for decreasing LDL-cholesterol concentration and increasing HDL-cholesterol concentration in the blood to reduce the risk of atherosclerosis and vascular disease. US patent 5,855,892. January 5, 1999.
91. Reinli, K. and Block, G. 1996. Phytoestrogen content of foods-a compendium of literature values. Nutr. Cancer. 26(2):123-148.
92. Segelman, A.B. 2000. Use of isoflavones to prevent hair loss and preserve the integrity of existing hair. US patent 6,017,893. January 25, 2000.
93. Setchell, K.D.R. 1998. Phytoestrogens: the biochemistry, physiology, and implications for human health of soy isoflavones. Am. J. Clin. Nutr. 68(suppl):1333S-1346S.
94. Setchell, K.D.R. and Cassidy, A. 1999. Dietary isoflavones: biological effects and relevance to human health. J. Nutr. 129:758S-767S.
95. Setchell, K.D.R. and Welsh, M.B. 1987. High-performance liquid chromatographic analysis of phytoestrogens in soy protein preparations with ultraviolet, electrochemical and thermospray mass spectrometric detection. J. Chromatogr. 386:315-323.
96. Setchell, K.D.R., Hulme, P., Kirk, D.N., and Axelson, M. 1984. Nonsteroidal estrogens of dietary origin: possible roles in hormone-dependent disease. Am. J. Clin. Nutr.40:567-578.
97. Setchell, K.D.R., Welsh, M.B., and Lim, C.K. 1987. HPLC analysis of phytoestrogens in soy protein preparations with ultraviolet, electrochemical, and thermospray mass spectrometric detection. J. Chromatogr. 368: 315-323.
98. Setchell, K.D.R., Zimmer-Nechemisa, L., Cai, J., and Heubi, J.E. 1997. Exposure of infants to phytoestrogens from soy-based infant formula. Lancet. 350:23-27.
99. Shen, J.L. 1994a. Aglycone isoflavone-enriched vegetable protein fiber. US patent 5,350,949. June 14, 1994.
100. Shen, J.L. 1994b. Aglycone isoflavone-enriched vegetable protein fiber. US patent 5,352,384. October 4, 1994.
101. Shen, J.L. and Bryan, B.A. 1995a. An aglycone isoflavone-enriched vegetable protein concentrate and process for producing. International Patent WO 95/10529. April 20, 1995.
102. Shen, J.L. and Bryan, B.A. 1995b. An aglycone isoflavone enriched vegetable protein extract and isolate and process for producing. International Patent WO 95/105230. April 20, 1995.
103. Shen, J.L. and Bryan, B.A. 1995c. An aglycone isoflavone enriched vegetable whey, whey protein and process for producing. International Patent WO 95/10512. April 20, 1995.
104. Shen, J.L. and Bryan, B.A. 1997a. Aglycone isoflavone enriched vegetable protein concentrate and process for producing. US patent 5,637,562. June 10, 1997.
105. Shen, J.L. and Bryan, B.A. 1997b. Aglycone isoflavone enriched vegetable protein whey, and whey protein and process for producing. US patent 5,637,561. June 10, 1997.
106. Shen, J.L. and Bryan, B.A. 1998. Aglycone isoflavone enriched vegetable protein extract and isolate and process for producing. US patent 5,763,389. June 9, 1998.
107. Shen, J.L and Bryan, B.A. 2000. Aglycone isoflavone-enriched vegetable protein extract and isolate and process for producing. US patent 6,015,785. January 18, 2000.
108. Shen, J.L., Roussey, M.A., Bryan, B.A., and Allred, M.C. 1998. Aglycone isoflavone enriched vegetable protein whey, whey protein material aglycone isoflavone material high genistein material and high daidzein content material and process for producing the same from a vegetable protein whey. US patent 5,851,792. December 22, 1998.
109. Shen, J.L., Guevara, B.F., Spadafora, F.E., and Bryan, B.A. 2000. Isoflavone rich protein isolate and process for producing. US patent 6,013,771. January 11, 2000.
110. Song, T., Barua, K., Buseman, G., and Murphy, P.A. 1998. Soy isoflavone analysis: quality control and new internal standard. Am. J. Clin. Nutr. 68(suppl):1474S-1479S.
111. Stephens, F.O. 1999. The rising incidence of breast cancer in women and prostate cancer in men. Dietary influences: a possible preventive role for nature's sex hormone modifiers-the phytoestrogens (review). Oncol. Reports. 6:865-870.
112. Takebe, M., Ando, Y., and Kikushima, S. 1999. Process for preparing a product from a pulse crop as a starting material and a food containing the product prepared from a pulse crop as a starting material. US patent 5,885,632. March 23, 1999.
113. Thurn, M.J. and Juang, L.J. 1999. Methods for treating cancer with legume plant extracts. US patent 6,004,558. December 21, 1999.
114. Tsukamoto, C., Shimada, S., Igita, K., Kudou, S., Kokubun, M., Okubo, K., and Kitamura, K. 1995. Factors affecting isoflavone content in soybean seeds: changes in isoflavones, saponins, and composition of fatty acids at different temperatures during seed development. 43:1184-1192.
115. Vanttinen, K. and Moravcova, J. 1999. Phytoestrogens in soy foods: determination of daidzein and genistein by capillary electrophoresis. Czech. J. Food Sci. 17:61-67.
116. Waggle, D.H. and Bryan, B.A. 1998. Recovery of isoflavones from soy molasses. US patent 5,821,361. October 13, 1998.
117. Waggle, D.H. and Bryan, B.A. 1999a. Recovery of isoflavones from soy molasses. US patent 5,919,921. July 6, 1999.
118. Waggle, D.H. and Bryan, B.A. 1999b. Recovery of isoflavones from soy molasses. US patent 5,990,291. November 23, 1999.
119. Walter, E.D. 1941. Genistin (an isoflavone glucoside) and its aglycone, genistein, from soybeans. J. Am. Chem. Soc. 63:3273-3276.
120. Wang, G., Kuan, S.S., Francis, O.J., Ware, G.M., and Carman, A.S. 1990. A simplified HPLC method for the determination of phytoestrogens in soybean and its processed products. J. Agric. Food Chem. 38:185-190.
121. Wang, C., Ma, Q., Pagadala, S., Sherrard, M.S., and Krishnan, P.G. 1998. Changes of isoflavones during processing of soy protein isolates. J. Am. Oil. Chem. Soc.75:337-341.
122. Wang, H. and Murphy, P.A. 1994a. Isoflavone content in commercial soybean foods. J. Agric. Food. Chem. 42:1666-1673.
123. Wang, H. and Murphy, P.A. 1994b. Isoflavone composition of American and Japanese soybeans in Iowa: effects of variety, crop year, and location. J. Agric. Food Chem.42:1674-1677.
124. Wang, H. and Murphy, P.A. 1996. Mass balance study of isoflavones during soybean processing. J. Agric. Food Chem. 44:2377-2383.
125. Weber, J.M., Cinstantinou, A., and Hessler, P.E. 1996. Process for preparing genistein. US patent 5,554,519. September 10, 1996.
126. Wei, H. and Frenkel, K. 1993. Relationship of oxidative events and DNA oxidation in SENCAR mice to in vivo promoting activity of phorbol ester-type tumor promoters. Carcinogenesis. 14:1195-201
127. Wei, H., Wei, L.H., Frenkel, K., Bowen, R., and Barnes, S. 1993. Inhibition of tumor promoter induced hydrogen peroxide formation in vitro and in vivo by genistein. Nutr Cancer. 20:1-12.
128. Wei, H., Bowen, R., Cai, Q., Barnes, S., and Wang, Y. 1995. Antioxidant and antipromotional effects of the soybean isoflavone genistein. Proc. Soc. Exp. Biol. 208:124-130.
129. Wei, H., Cai, Q.Y., and Rahn, R.O. 1996. Inhibition of UV light and Fenton reaction induced oxidative DNA damage by the soybean isoflavone genistein. Carcinogenesis. 17(1):73-77.
130. Whitten, P.L. and Naftolin, F. 1998. Reproductive actions of phytoestrogens. Baillieres Clin. Endocrinol Metab. 12:667-690.
131. Whitten, P.L., Lewis, C., Russell, E., and Naftolin, F. 1995. Potential adverse effects of phytoestrogens. J. Nutr. 125:771S-776S.
132. Wu, A.H., Horn-Ross, P.L., Nomura, A.M., West, D.W., Kolonel, L.N., Rosenthal, J.F., Hoover, R.N., and Pike, M.C. 1996. Tofu and risk of breast cancer in Asian-Americans. Cancer Epidemiol., Biomarkers Prevent. 5:901-906.
133. Xu, X., Harris, K.S., Wang, H.J., Murphy, P.A., and Hendrich, S. 1995. Bioavailability of soybean isoflavones depends upon gut microflora in women, J. Nutr. 125:2307-2315.
134. Yamashita, Y., Kawada, S., and Nakano, H. 1990. Induction of mammalian topoisomerase II dependent DNA cleavage by antitumor antibiotic streptonigrin. Cancer Res. 50(18):5841-5844.
135. Zhang, Y., Song, T.T., Cunnick, J.E., and Murphy, P.A. 1999. Daidzein and genistein glucuronides in vitro are weakly estrogenic and activate human natural killer cells at nutritionally relevent concentrations. J. Nutr. 129:399-405.
136. Zheng, B.L., Yegge, J.A., Bailey, D.T., and Sullivan, J.L. 1997. Process for isolation and purification of isoflaovnes. US patent 5,679,806. October 21, 1997.
137. Zilliken, F.W. 1980a. Antioxidants, antioxidant compositions and methods of preparing and using same. US patent 4,218,489. August 19, 1980.
138. Zilliken, F.W. 1980b. Antioxidants, antioxidant compositions and methods of preparing and using same. US patent 4,232,122. November 4, 1980.
139. Zilliken, F.W. 1981. Isoflavones and related compounds, methods of preparing and using and antioxidant compositions containing the same. US patent 4,264,509. April 28, 1981.
140. Zilliken, F.W. 1982a. Isoflavones and related compounds, methods of preparing and using and antioxidant compositions containing same. US patent 4,366,082. December 28, 1982.
141. Zilliken, F.W. 1982b. Fermentation method of preparing antioxidants. US patent 4,366,2248. December 28,1982.
142. Zilliken, F.W. 1983. Isoflavones and related compounds, methods of preparing and using and antioxidant compositions containing same. US patent 4,390,559. June 28, 1983.