Formation mechanism for potent antioxidative O-dihydroxyisoflavones in soybeans fermented with aspergillu

Bioscience, Biotechnology and Biochemistry

Volumn 63, Issue 5, 1999, Pages 851-858

  Esaki, Hideo ^a   Watanabe, Ryoko ^a   Onozaki, Hiromichi ^a   Kawakishi, Shunro ^a  

^a SUGIYAMA JOGAKUEN UNIVERSITY   (Japan)

Author keywords

8 hydroxydaidzein; 8 hydroxygenistein; Antioxidant; Aspergillus saitoi; Sporulation

Indexed keywords

EID: 0011458097     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.63.851     Document Type: Article

References (33)

1. Pratt, D. E. and Birac, P. M., Source of antioxidant activity of soybeans and soy products. J. Food Sci., 44, 1720-1722 (1979).
2. Tsuda, T., Watanabe, M., Ohshima, K., Yamamoto, A., Kawakishi, S., and Osawa, T., Anti oxidative components isolated from the seed of tamarind (Tamarindus indica L.). J. Agric. Food Chem., 42, 2671-2674 (1994).
3. Fukuda, Y., Food chemical studies on the antioxidants in sesame seed. Nippon Shokuhin Kogyo Gakkaishi (in Japanese), 37, 484-492 (1990).
4. Tada, M., Matsumoto, R., Yamaguchi, H., and Chiba, K., Novel antioxidants isolated from Perilla frutescens Briton var. crispa (Thunb.). Biosci. Biotechnol. Biochem., 60, 1093-1095 (1996).
5. Gyorgy, P., Murata, K., and Ikehata, H., Antioxidants isolated from fermented soybeans (tempeh). Nature, 203, 870-872 (1964).
6. Nakatani, N., Recent advances in the study on natural antioxidants. Nippon Shokuhin Kogyo Gakkaishi (in Japanese), 37, 569-576 (1990).
7. Matsuzaki, T. and Hara, Y., Antioxidative activity of tea leaf catechins. Nippon Nogeikagaku Kaishi (in Japanese), 59, 129-134 (1985).
8. Hertog, M. G. L., Hollman, P. C. H., and Van de Putte, B., Content of potentially anticarcinogenic flavonoids of tea infusions, wines, and fruit juices. J. Agric. Food Chem., 41, 1242-1246 (1993).
9. Ames, B. N., Dietary carcinogens and anticarcinogens: Oxygen radicals and degenerative disease. Science, 221, 1256-1264 (1983).
10. Osawa, T., Namiki, M., and Kawakishi, S., Role of dietary antioxidants in protection against oxidative damage. In “Antimutagenesis and Anticarcinogenesis Mechanisms II,” ed. by Kuroda, Y., Shankel, D. M., and Waters, M. D., Plenum Press, New York pp. 139-153 (1990).
11. Stampfer, M. J., Hennekens, C. H., Manson, J., Colditz, G. A., Rosner, B., and Willet, W. C., Vitamin E consumption and the risk of coronary diseases in women. New Engl. J. Med., 328, 1444-1449 (1993).
12. Rimm, E. B., Stampfer, M. J., Ascherio, A., Giovannucci, E., Colditz, G. A., and Willet, W. C., Vitamin E consumption and the risk of coronary diseases in men. New Engl. J. Med., 328, 1450-1456 (1993).
13. 3in liver, lung, kidney heart, and spleen. J. Agric. Food Chem., 44, 854-858 (1996).
14. Hertog, G. L., Feskens, E. J. M., Hollman, P. C. H., Katan, M. B., and Kromhout, D., Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly study. Lancet, 342, 1007-1011 (1993).
15. Okubo, K., DMF (dry mouth feel, undesirable) components of soybeans and behavior of the components on soybean food processing. Nippon Shokuhin Kogyo Gakkaishi (in Japanese), 35, 866-874 (1988).
16. Ikehata, H., Wakaizumi, M., and Murata, K., Antioxidant and antihemolytic activity of a new isoflavone, “Factor 2” isolated from tempeh. Agric. Biol. Chem., 32, 740-746 (1968).
17. Esaki, H., Onozaki, H., and Osawa, T., Antioxidative activity of fermented soybean products. In “Food Phytochemicals for Cancer Prevention I,” ed. by Fluang, M.-T., Osawa, T., Flo, C.-T., and Rosen, R. T., American Chemical Society, Washington DC pp. 353-360 (1994).
18. Berghofer, E., Grzeskowiak, B., and Mundigler, N., Int. J. Food Sci. Nutr., 49, 45-54 (1998).
19. Esaki, H., Onozaki, H., Kawakishi, S., and Osawa, T., New antioxidant isolated from tempeh. J. Agric. Food Chem., 44, 696-700 (1996).
20. Esaki, H., Onozaki, H., Morimitsu, Y., Kawakishi, S., and Osawa, T., Potent antioxidative isoflavones isolated from soybeans fermented with Aspergillus saitoi. Biosci. Biotechnol. Biochem., 62, 740-746 (1998).
21. Chang, W. H., Luu, H. X., and Cheng, A. C., A TLC-fluores-cent method of detecting and evaluating individual antioxidative components. J. Food Sci., 48, 658-659 (1983).
22. Mohri, K., Dohmoto, C., Ikesu, FL, and Igarashi, O., A simple elimination method of vitamin E from vegetable and fish oils for the preparation of vitamin E deficient diet. Nippon Eiyo Shokuryo Gakkaishi (in Japanese), 36, 122-124 (1983).
23. Matsuura, M., Sasaki, J., and Murao, S., Studies on /J-glucosi-dase from soybeans that hydrolyze daidzin and genistin: Isola-tion and characterization of an isozyme. Biosci. Biotechnol. Biochem., 59, 1623-1627 (1995).
24. Cheynier, V. and Moutounet, M., Oxidative reactions of caffeic acid in model systems containing polyphenol oxidase. J. Agric. Food Chem., 40, 2038-2044 (1992).
25. Ebata, J., Fukuda, Y., Hirai, K. and Murata, K., yS-Glucosidase involved in the antioxidant formation in tempeh, fermented soybeans. Nippon Nougeikagaku Kaishi (in Japanese), 46, 323-329 (1972).
26. Matsuda, S., Norimoto, F., Matsumoto, Y., Ohba, R., Teramoto, Y., Ohta, N., and Ueda, S., Solubilization of a novel isoflavone glycoside-hydrolyzing /Fglucosidase from Lactobacillus casei subsp. rhamnosus. J. Ferment. Bioeng., 11, 439-441 (1993).
27. Workman, W. E. and Day, D. F., Purification and properties of /?-glucosidase from Aspergillus terreus. Appl. Environ. Microbiol., 44, 1289-1295 (1982).
28. Kwon, K.-S., Kang, H. G., and Hah, Y. C., Purification and characterization of two extracellular /?-glucosidases from Aspergillus nidulans. FEMS Microbiol. Lett., 97, 149-154 (1992).
29. Peterson, D. H. and Murray, H. C., Microbial oxygenation of steroids at carbon 11. J. Am. Chem. Soc., 74, 1871-1872 (1952).
30. Noma, Y. and Tatsumi, C., Conversion of (—)-carvone by Pseudomonas ovalis, strain 6-1 (1): Microbial conversion of terpenes, part XIII. Nippon Nougeikagaku Kaishi (in Japanese), 47, 705-711 (1973).
31. Pan, S. C. and Weisenborn, F. L., Microbiological transformation of rauwolfia alkaloids. J. Am. Chem. Soc., 80, 4749 (1958).
32. Jeffrey, A. M., Knight, M., and Evans, W. C., The bacterial degradation of flavonoids: Hydroxylation of the A-ring of taxifo-lin by a soil pseudomonad. Biochem. J., 130, 373-381 (1972).
33. Klus, K. and Barz, W., Formation of polyhydroxylated isoflavones from the isoflavones genistein and biochanin A by bacteria isolated from tempe. Phytochemistry, 47, 1045-1048 (1998)