Changes in Isoflavone Content of Soybeans during Heating Process

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1 1 Nippon Shokuhin Kagaku Kogaku Kaishi Vol. /-, No.1, -0/ -1, (,0) 365 Changes in Isoflavone Content of Soybeans during Heating Process Atsuko Kasuga, Eiko Ogiwara, Yasuo Aoyagi and Hiroko Kimura Junior College of Kagawa Nutrition University, -,. - Komagome, Toshima-ku, Tokyo Kagawa Vocational College of Nutrition, -,. - Komagome, Toshima-ku, Tokyo Kagawa Nutrition University, - 3, Chiyoda, Sakado-shi -/,22 In order to examine the bioavailability of soybean isoflavone and to obtain basic nutritional data, we measured separately the quantities of each of twelve kinds of isoflavone contained in soybeans: malonyl glucosides, acetyl glucosides, glucosyl glucosides and aglycon. First, we analyzed six types of soybean generally seen in the market. Di#erences in total isoflavone content, some greater than, were observed depending on the type of bean. Second, we analyzed the compositional changes of isoflavone, using a heating method that reflected the domestic cooking process, with soybeans of known quantities. Isoflavones were not eluted to a significant extent by immersion in water, but after boiling for - min, 2 3 of the isoflavones dissolved in water, which was drained o#. By boiling for - min and 0 min,,. and -, respectively, of the total isoflavone contents in soybean broth were dissolved. Upon heating, the content of glucosyl glucosides decreased and that of malonyl glucosides increased; this tendency became more marked as the heating time was extended. Although heating time was shorter when a pressure cooker was used, elution of isoflavone was no greater than when the broth was boiled normally. When a steamer was used for heating, only small amounts of isoflavones could be eluted. (Received Dec. 1,,/; Accepted Apr. 2,,0) Sirtori, -. / 0 Liggin 1 2 3, Nakamura,1.2 mg day,., mg, Glycitein,.- mg, -..2 mg Kimura , ,. - -/,22-3, Corresponding author kasuga@eiyo.ac.jp mg 0., mg,-.,1 mg,, mg day - Kimura

2 366 /- 1,0 1 2 Barnes. Hutchins / Izumi 0 0,,, - kg,.1 kg.,, 0 -/ g. - A, B, C, D, E /, Glycitein,, SIGMA,,,,,,, LC Laboratories, g ml., g / / g / NIR-,/,, /,. cm -, / NK-C,3-0 / -,, cm,../ l T-FAL NEW CLISPO, /,. cm, 1.- cm, cm ml - 0 ml

3 3 : 367 / g,0 cm, g 23 g, ml / ml,,2 g - 1, g ml,. mol/l, ml, No. - ADVANTEC - 2 HPLC - 2 HPLC, WANG 2 HPLC : 22- PU :. ml min, :UV,0 nm 0// : TSK-GEL..0 mm ID / cm :.1 : A. / B. -/ A:B 3/ : /, A:B 3/ : / 0/ : -/, 0 A:B 0/ : -/ g,33 mg,,-0 mg,,/ mg, mg,.- mg, 1, Wang and Murphy Toda, / - 1, Kudou 1, Tsukamoto, mg g Glycitein /40,40,4, -41,41 /, ,,43,4.,.4 /4. 04/,.4, 4/ 4 4, /43,4,, ,/41, / 142 / /42 4, --40,43 2,4, 4/ 142.4/ / , 41 4, 14/ Total,334-,040,-/42,/4. -/41,4-.,43

4 368 /- 1,0 1 4 : / / : -, :. 3,,,, , Franke,- - Glylcitein././ 0 Toda,. 3/ 0 1, 0./ - Glycitein : : Frake,- 1/ 3,2 00 Toda,.

5 5 : 369, : : Toda,. bo /, bo, / 1,2 / - 0 Francis,/ Matsuura,0 Kudou , 3/.0 g 03./..- g -../, g 0

6 370 /- 1,0 1 6, mg gor 0 A B C A B Glycitein.4/ 4,,41, / ,,42 40, , 40, / /4/ 4 4,, /.42 4., / 4, 14 4/ , ,34, , /4-4, ,, , - 4/ 4,42 4-, , /,4.40,4, 40,4-4, Total 204/ /04. -4, 0241,-42 / /-4 14 / g g 0 mg 0 B B B. - g 0, /,.

7 7 : 371 2, Wang,1, Toda,. 2/ /, 0 Caward,2,3 Toda - Bucillus subtilis natto g,33 mg,,, 1 - -,. 0-0 g 0 mg 0 2, Sirtori, C.R., Agradi, E., Conti, F., Mantero, O. and Gatti, E., Soybean-protein diet in the treatment of type-ii hyperlipoproteinaemia. Lancet, -3,,1/,11 311, Kuiper, G., Lemmen, J.G., Carlsson, B., Corton, J.C., Safe, S.H., VanderSaag, O.T., VanderBurg, P. and Gustafsson, J.A., Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta., Endocrinology, -3,.,/,., Barkhem, T., Carlsson, B., Nilsson, Y., Enmark, E., Gustafsson, J.A. and Nilsson, S., Di#erential response of estrogen receptor alpha and estrogen receptor beta to partial estrogen agonists/antagonists, Molecular Pharmacology, /., /, 332. Adlercreutz, H., Fotsis, T., Bannwart, C., Wahala, K., Makela, T., Brunow, G. and Hase, T., Determination of urinary lignans and phytoestrogen metabolites, potential antiestrogens and anticarcinogens, in urine of women on various habitual diets, J. Steroid Biochem.,,/, / Akiyama, T., Ishida, J., Nakagawa, S., Ogawara, H., Watanabe, S., Itoh, N., Shibuya, M. and Fukami, Y.,, a specific inhibitor of Tyroshine-specific protein kinases, J. of Biolog. Chem.,,0,, //3, //3/ Bingham, S.A., Atkinson, C., Liggins, J., Bluck, L. and Coward, A., Plant oestrogens : where are we now?, Br. J. Nutr. 13, Liggins, J., Bluck, L. J.C., Runswick, S., Atkinson, C.M., Coward, W.A. and Bingham, S.A., and genistein content of vegetables, Br. J. Nutr., 2., 11 1,/, 2 Liggins, J., Bluck, L. J.C., Runswick, S., Atkinson, C., Coward, W.A. and Bingham, S.A., and genistein content of fruit and nuts, J. Nutr. Biochem.,, -,0 --, 3 Liggins, J., Mulligan, A., Runswick, S. and Bingham, S. A., and genistein content of cereals, European J. of Clinical Nutrition, /0, ,,

8 372 /- 1,0 1 8 Nakamura, Y., Tsuji, S. and Tonogai, Y., Determination of the levels of isoflabonoids in soybeans and soyderived foods and estimation of isoflvonoids in the Japanese daily intake, J. of AOAC International, 2-, 0-/ 0/, Kimura, M., Arai, Y., Shimoi, K. and Watanabe, S., Japanese Intake of Flavonoids and Isoflavonoids from Foods, J. of Epidem., 2, 02 1/ 332, FFI No. 1, Munro, I.C., Harywood, M., Hlywka, J., Stephen, A.M., Doull, J., Flamm, W.G. and Adlercreutz, H., Soy Isoflavones : A safety review, Nutrition Reviews, 0, --,-. Barnes, S. and Kirk, M., Isoflavones and their conjugates in soy foods : extraction conditions and analysis by HPLC-mass spectrometry, J. Agric. Food Chem.,.,,,.00, / Hutchins, A.M., Slabin, J.L. and Lampe, J.W., Urinary isoflavonoid phytoestrogen and lignan excretion after consumption of fermented and unfermented soy products, J. Am. Diet. Assoc., 3/, /./ // 33/ 0 Izumi, T., Piskula, M.K., Osawa, S., Obata, A., Tobe, K., Saito, M., Kataoka, S., Kubota, Y. and Kiuchi, M., Soy isoflavone aglycones are absorbed faster and in higher amounts than their glucosides in humans, J. Nutr., -, 03/ 033, 1 Kudou, S., Fluery, Y., Welti, D., Magnolata, D., Uchida, T., Kitamura, K. and Okubo, M., Malonyl isoflavone glycosides in soybean seeds, Agric. Biol. Chem., //,,,,1,, Wang, H. and Murphy, P.A., Isoflavone content in commercial soybean foods, J. Agric. food Chem.,.,, Wang, H. and Murphy, P.A., Isoflavone composition of American and Japanese soybeans in Iowa : E#ects of variety, crop iear, and location, J. Agric. food Chem.,.,, , Tsukamoto, C., Shimada, S., Igita, K., Kudou, S., Kokubun, M., Okubo, K. and Kitamura, K., Factors a#ecting isoflavone content in soybean seeds : changes in isoflavones, saponins, and composition of fatty acids at di#erent temperatures during seed development, J. Agric. Food Chem.,.-, 2. 3, 33/, Coward, L, Barnes, N.C., Setchell, K.D.R. and Barnes, S., The antitumor isoflavones, genistein and daidzein, in soybean foods of American and Asian diets, J. Agric. Food Chem.,., ,, 1. /,-,- Franke, A.A., Hankin, J.H., Yu, M.C., Maskarinec, G., Low, S.H. and Custer, L. J., Isoflavone levels in soy foods consumed by multiethnic populations in Singapore and Hawaii, J. Agric Food Chem.,.1, ,. Toda, T., Sakamoto, A., Takayanagi, T. and Yokotsuka, K., Changes in isoflabone compositions of soybean foods during cooking process, Food Sci. Technol. Res., 0, -. -3,,/ Francis, J.M., The influence of isoflavone glycosides on the taste of subterranean clover leabes, J. Sci. Food Agric.,,.,,-/,. 31-,0 Matsuura, M., Obata, A. and Fukushima, D., Objectionable flavor of soy milk developed during the soaking of soybeans and its control, J. Food Sci., /., 0, 0/ 323,1 Wang, H., Murphy, P.A., Mass Balance Study of Isoflavones during soybean Processing, J. Agric. Food Chem.,..,,-11,-2-330,2 Coward, L., Smith, M., Kirk, M. and Barnes, S., Chemical modification of isoflavones in soyfoods during cooking and processing, Am. J. Clin. Nutr., 02, ,3., -,, -,1 33/ - Toda, T., Uesugi, T., Hirai, K., Nukaya, H., Tsuji, K. and Ishida, H., New 0-O-acyl isoflavone glycosides from soybeans fermented with Bacillus subtilis (natto). I. 0- O-succinylated isoflavone glycosides and their preventive e#ects on bone loss in ovariectomized rats fed a calcium-deficient diet, Biol. Pharm. Bull.,,,, 3-, 333 1,