Isoflavones and Coumestrol in Soybeans and Soybean Products from Australia and Indonesia

Journal of Food Composition and Analysis

Volumn 14, Issue 1, 2001, Pages 43-58

  Hutabarat, L S ^a   Greenfield, H ^a   Mulholland, M ^b  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

^b UNIVERSITY OF TECHNOLOGY SYDNEY   (Australia)

Author keywords

HPLC; soybean; daidzein; genistein; formononetin; biochanin A; coumestrol.

Indexed keywords

EID: 0035743417     PISSN: 08891575     EISSN: None     Source Type: Journal    
DOI: 10.1006/jfca.2000.0948     Document Type: Article

References (53)

1. Adlercreutz H., Fotsis T., Heikkinen R., Dwyer J. T., Goldin B. R., Gorbach S. L., Lawson A. M., Setchell K. D. R. Diet and urinary excretion of lignans in female subjects. Med. Biol. 59:1981;259-261.
2. Adlercreutz H., Fotsis T., Heikkinen R., Dwyer J. T., Woods M., Goldin B. R., Gorbach S. L. Excretion of the lignans enterolactone and enterodiol and of equol in omnivorous and vegetarian postmenopausal women and in women with breast cancer. Lancet. 2:1982;1295-1299.
3. Adlercreutz H., Fotsis T., Bannwart C., Wahala K., Makela T., Brunow G., Hase T. Determination of urinary lignans and phytoestrogens metabolites, potential antiestrogens and anticarcinogens, in urine of women on various habitual diets. J. Steroid Biochem. Mol. Biol. 25:1986;791-797.
4. Adlercreutz H., Fotsis T., Lampe J., Wahala K., Makela T., Brunow G., Hase T. Quantitative determination of lignans and isoflavonoids in plasma of omnivorous and vegetarian women by isotope dilution gas chromatography-mass spectrometry. Scan. J. Clin. Lab. Invest. 53:1993;5-18.
5. Adlercreutz H., Honjo H., Higashi A., Fotsis T., Hamalainen E., Hasegawa T., Okada H. Urinary excretion of lignans and isoflavonoid phytoestrogens in Japanese men and women consuming a traditional Japanese diet. Am. J. Clin. Nutr. 54:1991;1093-1100.
6. Adlercreutz H., Maosavi Y., Clark J., Kockerstedt K., Hamalainen E., Wahala K., Makela T., Hase T. Dietary phytoestrogens and cancer: in vitro and in vivo studies. J. Steroid Biochem. Mol. Biol. 41:1992;3-8.
7. Anderson R. L., Wolf W. J. Compositional changes in trypsin inhibitors, phytic acid, saponins and isoflavones related to soybean processing. J. Nutr. 125:1995;581S-588S.
8. Barnes S., Kirk M., Coward L. Isoflavones and their conjugates in soy foods: extraction conditions and analysis by HPLC-Mass spectrometry. J. Agric. Food Chem. 42:1994;2466-2474.
9. Bickoff E. M., Livingstone A. L., Hendrickson A. P., Booth A. N. Relative potencies of several oestrogen-like compounds found in forages. J. Agric. Food Chem. 10:1962;410-412.
10. Bradbury R. B., White D. E. Estrogens and related substances in plants. Vitamin Hormones. 12:1954;207-233.
11. Coward L., Barnes N. C., Setchell K. D. R., Barnes S. Genistein, daidzein, and their β -glycoside conjugates: anti tumor isoflavones in soybean foods from American and Asian diets. J. Agric. Food Chem. 41:1993;1961-1967.
12. Dalais F. M., Wahlqvist M. L., Rice G. E. Variation in isoflavonoid phytoestrogen content in soybeans grown in Australia. Proc. Nutr. Soc. Aust. 21:1997;161.
13. Dwyer J. T., Goldin B. R., Saul N., Gualtieri L., Barakat S., Adlercreutz H. Tofu and soy drinks contain phytoestrogens. J. Am. Diet. Assoc. 94:1994;739-743.
14. Eldridge A. C. Determination of isoflavones in soybean flours, protein concentrates, and isolates. J. Agric. Food Chem. 30:1982;353-355.
15. Eldridge A. C., Kwolek W. F. Soybean isoflavones: effect of environment and variety on composition. J. Agric. Food Chem. 31:1983;394-396.
16. FAO Food Balance Sheet, 1997, http://apps.fao.org/lim500/nph-wrap.pl/FoodBalanceSheet and Domain=FoodBalanceSheet.
17. Farnsworth N. R., Bingel A. S., Cordell G. A., Crane F. A., Fong H. H. S. Potential value of plants as sources of new antifertility agents II. J. Pharm. Sci. 64:1975;717-754.
18. Fotsis T., Adlercreutz H. The multi component analysis of estrogens in urine by ion exchange chromatography and GC-MS-I. Quantitation of estrogens after initial hydrolysis of conjugates. J. Steroid Biochem. 28:1987;203-213.
19. Franke A. A., Custer L. J., Cerna C. M., Narala K. K. Quantitation of phytoestrogens in legumes by HPLC. J. Agric. Food Chem. 42:1994;1905-1913.
20. Franke A. A., Custer L. J., Cerna C. M., Narala K. K. Rapid HPLC analysis of dietary phytoestrogens from legumes and from human urines. Proc. Soc. Exp. Biol. Med. 208:1995;18-26.
21. Franke A. A., Hankin J. H., Yu M. C., Maskarinec G., Low S., Custer L. J. Isoflavones levels in soy foods consumed by multiethnic populations in Singapore and Hawaii. J. Agric. Food Chem. 47:1999;977-986.
22. Hutabarat L. S., Greenfield H., Mulholland M. Quantitative determination of isoflavones and coumestrol in soybean by column liquid chromatography. J. Chromatogr. A. 886:2000;55-63.
23. Hutchins A. M., Lampe J. W., Martini M. C., Campbell D. R., Slavin J. L. Vegetables, fruits, and legumes: effect on urinary isoflavonoid phytoestrogen and lignan excretion. J. Am. Diet. Assoc. 95:1995;769-774.
24. Ikeda R., Ohta N., Watanabe T. Changes of isoflavones at various stages of fermentation in defatted soybeans. Nippon Shokuhin Kagaku Kogaku Kaishi. 42:1995;322-327.
25. Ingram D., Sanders K., Kolybaba M., Lopez D. Case-control study of phyto-oestrogens and breast cancer. Lancet. 350:1997;990-994.
26. James C. S. Analytical Chemistry of Foods. 1995;Blackie Academic and Professional, London.
27. King R. A., Bignell C. M. Concentrations of isoflavone phytoestrogens and their glucosides in Australian soya beans and soya foods. Aust. J. Nutr. Dietet. 57:2000;70-78.
28. Knight D. C., Eden J. A., Huang J. L., Waring M. A. Isoflavone content of infant foods and formulas. J. Paediatr. Child Health. 34:1998;135-138.
29. Knuckles B. E., deFremery D., Kohler G. O. Coumestrol content of fractions obtained during wet processing of alfalfa. J. Agric. Food Chem. 24:1976;1177-1180.
30. Kudou S., Fleury Y., Welti D., Magnolato D., Uchida T., Kitamura K., Okubo K. Malonyl isoflavone glycosides in soybean seeds (Glycine max Merrill). Agric. Biol. Chem. 55:1991;2227-2233.
31. Kuzer M. S., Lampe J. W., Martini M. C., Adlercreutz H. Fecal lignan and isoflavonoid excretion in premenopausal women consuming flaxseed powder. Cancer Epidemiol. Biomark. Prev. 4:1995;353-358.
32. Lampe J. W., Martini M. C., Kurzer M. S., Adlercreutz H., Slavin J. L. Urinary lignan and isoflavonoid excretion in premenopausal women consuming flaxseed powder. Am. J. Clin. Nutr. 60:1994;122-128.
33. Lee H. P., Gourley L., Duffy S. W., Esteve J., Lee J., Day N. E. Dietary effects on breast-cancer risk in Singapore. Lancet. 337:1991;1197-1200.
34. Liu K. Soybeans. 1997;Chapman and Hall, New York.
35. Lookhart G. L., Jones B. L., Finney K. F. Determination of coumestrol in soybeans by high-performance liquid and thin-layer chromatography. Am. Assoc. Cereal Chem. 55:1978;967-972.
36. Matsuura M., Obata A. β -glucosidases from soybeans hydrolyze daidzin and genistin. J. Food Sci. 58:1993;144-146.
37. Mazur W., Fotsis T., Wahala K., Ojala S., Salakka A., Adlercreutz H. Isotope dilution gas chromatographic-mass spectrometric method for the determination of isoflavonoids, coumestrol, and lignans in food samples. Anal. Biochem. 233:1996;169-180.
38. Murakami H., Asakawa T., Terao J., Matsushita S. Antioxidative stability of tempeh and liberation of isoflavones by fermentation. Agric. Biol. Chem. 48:1984;2971-2975.
39. Murphy P. A. Phytoestrogen content of processed soybean products. Food Technol. 36:1982;60-64.
40. Murphy P. A., Song T., Buseman G., Barua K. Isoflavones in soy-based infant formulas. J. Agric. Food Chem. 45:1997;4635-4638.
41. Murphy P. A., Song T., Buseman G., Barua K., Beecher G. R., Trainer D., Holden J. Isoflavones in retail and institutional soy foods. J. Agric. Food Chem. 47:1999;2697-2704.
42. Naim M., Gestetner B., Zilkah S., Birk Y., Bondi A. Soybean isoflavones. Characterisation, determination, and antifungal activity. J. Agric. Food Chem. 22:1974;806-810.
43. Reinli K., Block G. Phytoestrogen content of foods - a compendium of literature values. Nutr. Cancer. 26:1996;123-148.
44. Seo A., Morr C. V. Improved high-performance liquid chromatographic analysis of phenolic acid and isoflavonoids from soybean protein products. J. Agric. Food Chem. 32:1984;530-533.
45. Setchell K. D. R., Lawson A. M., Conway E., Taylor N. F., Kirk D. N., Cooley G., Farrant R. D., Wynn S., Axelson M. The definitive identification of the lignans trans-2,3-bis (3-hydroxybenzyl)-g-butyrolactone and 2,3-bis (3-hydroxybenzyl) butane-1,4-diol in human and animal urine. Biochem. J. 197:1981;447-458.
46. Shihabi Z. K., Kute T., Garcia L. L., Hinsdale M. Analysis of isoflavones by capillary electrophoresis. J. Chromatogr. A. 680:1994;181-185.
47. Smith G. R., Randel R. D., Bradshaw C. Influence of harvest date, cultivar, and sample storage method on concentration of isoflavones in subterranean clover. Crop Sci. 26:1986;1013-1016.
48. USDA-Iowa State University database on the isoflavone content of foods, release 1.1, 1999, http://www.nal.usda.gov/fnic/foodcomp/Data/isoflav/isoflav.html.
49. Wang G., Kuan S. S., Francis O. J., Ware G. M., Carman A. S. A simplified HPLC method for the determination of phytoestrogens in soybean and its processed products. J. Agric. Food Chem. 38:1990;185-190.
50. Wang H., Murphy P. A. Isoflavone composition of American and Japanese soybeans in Iowa: effects of variety, crop year, and location. J. Agric. Food Chem. 42:1994a;1674-1677.
51. Wang H., Murphy P. A. Isoflavone content in commercial soybean foods. J. Agric. Food Chem. 42:1994b;1666-1673.
52. Wang H., Murphy P. A. Mass balance study of isoflavones during soybean processing. J. Agric. Food Chem. 44:1996;2377-2383.
53. West L. G., Birac P. M., Pratt D. E. Separation of the isomeric isoflavones from soybeans by high-performance liquid chromatography. J. Chromatogr. 150:1978;266-268.