Quantitative determination of isoflavones in soy based nutritional supplements by high-performance liquid chromatography

Journal fur Verbraucherschutz und Lebensmittelsicherheit

Volumn 3, Issue 2, 2008, Pages 127-136

  Sturtz M ^a   Lander, V ^b   Schmid, W ^b   Winterhalter, Peter ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b BAVARIAN HEALTH AND FOOD SAFETY AUTHORITY   (Germany)

Author keywords

Isoflavones; Nutritional supplement; Quantitative determination; Soy

Indexed keywords

EID: 46749116804     PISSN: 16615751     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00003-008-0340-x     Document Type: Article

References (55)

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 kinases. J Biol Chem 262:5592-5595.
2. Arai, J., Watanabe, S., Kimira, M., Shimoi, K., Mochizuki, R., and Kinae, N. (2000) Dietary intakes of flavonols, flavones and isoflavones by Japanese women and the inverse correlation between quercetin intake and plasma LDL cholesterol concentration. J Nutr 130:2243-50.
3. Bingham S. A., Atkinson, C., Liggins, J., Bluck, L., and Coward, A. (1998) Phyto-oestrogens: where are we now? Br J Nutr 79:393-406.
4. Brouns, F. (2002) Soya isoflavones: a new and promising ingredient for the health foods sector. Food Res Int 35:187-193.
5. Cassidy, A., Hanley, B., and Lamuela-Raventos, R. M. (2000) Isoflavones, lignans and stilbenes - origins, metabolism and potential importance to human health. J Sci Food Agric 80:1044-1062.
6. Cheftel, J. C. (2005) Food and nutrition labelling in the European Union. Food Chem 93:531-550.
7. Chua, R., Anderson, K., Chen, J., and Hu, M. (2004) Quality, labelling accuracy, cost comparison of purified soy isoflavonoid products. J Altern Complement Med 10:1053-1060
8. COT (2003) Committee on Toxicity (COT) of the Food, Consumer Products and the Environment. Phytoestrogens and Health, Report 2003.
9. Coward, L., Barnes, N. C., Setchell, K. D. R., and Barnes, S. (1993) Genistein, daidzein, and their β-glycoside conjugates: antitumor isoflavones in soy bean foods from American and Asian diets. J Agric Food Chem 41:1961-1967.
10. da Costa César, I., Braga, F. C., Soares, C. D. V., de Aguiar Nunan, E., Pianetti, G. A., Condessa, F. A., Barbosa, T. A. F., and Campos, L. M. M. (2006) Development and validation of a RP-HPLC method for quantification of isoflavone aglycones in hydrolyzed soy dry extracts. J Chromatogr B 836:74-78.
11. Degenhardt, A., and Winterhalter, P. (2001) Isolation and purification of isoflavones from soy flour by high-speed countercurrent chromatography. Eur Food Res Technol 213:277-280.
12. Delmonte, P. Perry, J., and Jeanne I. Rader, J. I. (2006) Determination of isoflavones in dietary supplements containing soy, Red Clover and kudzu: Extraction followed by basic or acid hydrolysis. J Chromatogr B 1107:59-69.
13. Divi, R. L., Chang, H. C., and Doerge, D. R. (1997) Anti-thyroid isoflavones from soybean. Biochem Pharmacol 54:1087-1096.
14. Di Virgilio, A. L., Iwami, K., Wätjen, W., Kahl, R., and Degen, G. H. (2004) Genotoxicity of the isoflavones genistein, daidzein and equol in V79 cells: Festschrift dedicated to Christian Hodel. Toxicol Lett 151:151-162.
15. Dixon, R. A. (2004) Phytoestrogens. Annu Rev Plant Bio 55:225-261.
16. Doerge, D. R., and Chang, H. C. (2002) Inactivation of thyroid peroxidase by soy isoflavones, in vitro and in vivo. J Chromatogr 777:269-279.
17. Eldridge, A., and Kwolek, W. F. (1983) Soybean isoflavones: effect of environment and variety on composition. J Agric Food Chem 31:394-396.
18. Galati, G., and O'Brien, P. J. (2004) Potential toxicity of flavonoids and other dietary phenolics: significance for their chemopreventive and anticancer properties. Free Radic Biol Med 37:287-303.
19. Gulati, Om P., and Berry Ottaway, P. (2006) Legislation relating to nutraceuticals in the European Union with a particular focus on botanical-sourced products. Toxicology 221:75-87.
20. Howes, L. G., Howes, J. B., and Knight, D. C. (2006) Isoflavone therapy for menopausal flushes: A systematic review and meta-analysis. Maturitas 55:203-211.
21. Ito, Y., and Conway, W. D. (eds.) (1996) High-Speed Countercurrent Chromatography. Wiley-Interscience, New York.
22. Kinjo, J., Tsuchihashi, R., Morito, K., Hirose, T., Aomori, T., Nagao, T., Okabe, H., Nohara, T., and Masamune, P. (2004) Interactions of pytoestrogens with estrogen receptors α and β (III). Estrogenic activities of soy isoflavone aglycones and their metabolites isolated from human urine. Biol Pharm Bull 27:185-188.
23. Knight, D. C., and Eden, J. A. (1995) Phytoestrogens - a short review. Maturitas 22:167-175.
24. Krebs, E. E., Ensrud, K. E., MacDonald, R., and Wilt, T. J. (2004) Phytoestrogens for treatment of menopausal symptoms: a systematic review. Obstet Gynecol 104:824-836.
25. Kudou, S., Fleury, Y., Welti, D., Magnolato, D., Uchida, T., Kitamura, K., and Okubo, K. (1991) Malonyl isoflavone glycosides in soybean seeds (Glycine max Merrill). Agric. Biol. Chem. 55:2227-2233.
26. Kuiper, G., Nilsson, S., and Gustafson, J.-A. (1998) Characteristics and function of the novel estrogen receptors b. In: O'Malley B. W. (ed.) Hormones and Signaling. Academic Press, New York, 1:89-112.
27. Kulling, S. E., Rosenberg, B., Jacobs, E., and Metzler, M. (1999) The phytoestrogens coumestrol and genistein induce structural chromosomal aberrations in cultured human peripheral blood lymphocytes. Arch Toxicol 73:50-54.
28. Kulling, S. E., Lehmann, L., and Metzler, M. (2002) Oxidative metabolism and genotoxic potential of major isoflavone phytoestrogens. J Chromatogr B 777:211-218.
29. Liggins, J., Bluck, L. J. C., Runswick, S., Atkinson, C., Coward, W. A., and Bingham, S. A. (2000) Daidzein and genistein content of fruit and nuts. J Nutr Biochem 11:326-331.
30. Mathias, K., Ismail, B., Corvalan, C. M., and Hayes, K. D. (2006) Heat and ph effects on the conjugated forms of genistin and daidzin isoflavones. J Agric Food Chem 54:7465-7502.
31. McClain, R. M., Wolz, E., Davidovich, A. and Bausch, J. (2006) Genetic toxicity studies with genistein. Food Chem Toxicol 44:42-55.
32. McClain, R. M., Wolz, E., Davidovich, A., Edwards, J., and Bausch, J. (2007) Reproductive safety studies with genistein in rats. Food Chem Toxicol 45:1319-1332.
33. Mei J., Yeung, S. S., and Kung, A. W. (2001) High dietary phytoestrogen intake is associated with higher bone mineral density in postmenopausal but not premenopausal women. J Clin Endocrinol Metab 86:5217-5221.
34. Morito, K., Hirose, T., Jinjo, J., Hirakawa, T., Okawa, M., Nohara, T., Ogawa, S., Inoue, S. Muramatsu, M., and Masamune, Y. (2001) Interaction of phytoestrogens with estrogen receptors α and β. Biol Pharm Bull 24:351-356.
35. Nahas, E. P., Nahás Neto, J., de Luca, L., Traiman, P., Pontes, A., and Dalben, I. (2004) Benefits of soy germ isoflavones in postmenopausal woman with containdication for conventional hormone replacement therapy. Maturitas 48:372-380.
36. Nakamura, Y., Tsuji, S., and Tonogai, Y. (2000) Determination of the levels of isoflavonoids in soybeans and soy-derived foods and estimation of isoflavonoids in the Japanese daily intake. J AOAC Int 83:635-650.
37. Nelson, H. D., Vesco, K. K., Haney, E., Fu, R., Nedrow, A., Miller, J., Nicolaidis, C., Walker, M., and Humphrey, L. (2006) Nonhormonal therapies for menopausal hot flashes: systematic review and meta-analysis. JAMA - J Am Med Assoc 295:2057-2071.
38. Newbold, R. R., Banks, E. P., Bullock, B., and Jefferson, W. N. (2001) Uterine adenocarcinoma in mice treated neonatally with genistein. Cancer Res 61:4325-4328.
39. Nurmi, T., Mazur, W., Heinonen, S., Kokkonen, J. and Adlercreutz, H. (2002) Isoflavone content of the soy based supplements. J Pharm Biomed Anal 28:1-11.
40. Ribeiro, M. L. L., Mandarino, J. M. G., Carrão-Panizzi, M. C., de Oliveira, M. C. N., Campo, C. B. H., Nepomuceno, A. L., and Ida, E. I. (2007) Isoflavone content and β-glucosidase activity in soybean cultivars of different maturity groups. J Food Composition and Analysis 20:19-24.
41. Rüfer, C.E., Bub, A., Möseneder, J., Winterhalter, P., M. Stürtz, M., and Kulling, S. E. (2008) Pharmacokinetics of the soybean isoflavone daidzein in its aglycone and glucoside form: a randomized, double-blind, cross-over study. Am J Clin Nutr (submitted).
42. Setchell, K.D., Brown, N. M., Desai, P., Zimmer-Nechemias, L., Wolfe, B. E., Brashear, W. T., Kirschner, A. S., Cassidy, A., and Heubi, J. E. (2001) Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements. J Nutr 131:1362S-75S.
43. Schmitt, E., Metzler, M., Jonas, R., Dekant, W., and Stopper, H. (2003) Genotoxic activity of four metabolites of the soy isoflavone daidzein. Mutat Res 542:43-48.
44. SKLM (2007) DFG - Senate Commission on Food Safety (May 2007) Isoflavones as phytoestrogens in food supplements and dietary foods for special medical purposes http://www.dfg.de/sklm.
45. Song, T., Barua, K., Buseman, G., and PA Murphy, P. A. (1998) Soy isoflavone analysis: quality control and a new internal standard. Am J Clin Nutr 68:1474S-1479S.
46. Stürtz, M., Lander, V., Schmid, W., and Winterhalter, P. (2006) Preparative isolation of isoflavones from soy and red clover. Mol Nutr Food Res 50:356-361.
47. Tikkanen, M. J., and Adlercreutz, H. (2000) Dietary soy-derived isoflavone phytoestrogens, could they have a role in coronary heart disease prevention? Biochem Pharmacol 60:1-5.
48. Tsai, H.-S., Huang, L.-J., Lai, Y.-H., Chang, J.-C., Lee, R.-S., and Chiou, R. Y.-Y. (2007) Solvent effects on extraction and HPLC analysis of soybean isoflavones and variations of isoflavone compositions as affected by crop season. J Agric Food Chem 55:7712-7715.
49. Unfer, V., Casini, M. L., Costabile, L., Mignosa, M., Gerli, S., and di Renzo, G. C. (2004) Endometrial effects of long-term treatment with phytoestrogens: a randomized, double-blind, placebocontrolled study. Fertil Steril 82:145-148.
50. Usui, T. (2006) Pharmaceutical Prospects of Phytoestrogens. Endocr J 53:7-20.
51. Wakai, K., Egami, I., Kato, K., Kawamura, T., Tamakoshi, A., Lin, Y., Nakayama, T., Wada, M., and Ohno, Y. (1999) Dietary intake and sources of isoflavones among Japanese. Nutr Cancer 33:139-45.
52. Wang, H. and Murphy, P. A. (1994) Isoflavone content in commercial soybean foods. J Agric Food Chem 42:1666-1673.
53. Wiseman, H., Karen Casey, K., Clarke, D. B., Barnes, K. A., and Bowey, E. (2002) Isoflavone aglycon and glucoconjugate content of high- and low-soy U.K. foods used in nutritional studies. J Agric Food Chem 50:1404-1410.
54. Wuttke, W., Jarry, H., Westphalen, S., Christoffel, V., and Seidlova-Wuttke, D. (2002) Phytoestrogens for hormone replacement therapy? J Steroid Biochem Mol Biol 83:133-147.
55. Yamashita, Y., Kawada, S., and Nakano, H. (1990) Induction of mammalian topoisomerase II dependent DNA cleavage by nonintercalative flavonoids, genistein and orobol. Biochem Pharmacol 39:737-744.