Composition and Content of Soyasaponins and Their Interaction with Chemical Components in Different Seed-Size Soybeans

  • Kim Sun-Lim (National Institute of Crop Science, R.D.A.) ;
  • Berhow Mark A. (USDA-ARS, National Center of Agricultural Utilization Research) ;
  • Kim Jung-Tae (Department of Applied Life Science, College of Life and Environment Science, Konkuk University) ;
  • Chung Ill-Min (Department of Applied Life Science, College of Life and Environment Science, Konkuk University) ;
  • Chi Hee-Youn (National Institute of Crop Science, R.D.A.) ;
  • Song Jin (National Institute of Crop Science, R.D.A.) ;
  • Park Nam-Kyu (National Institute of Crop Science, R.D.A.) ;
  • Son Jong-Rok (National Institute of Crop Science, R.D.A.)
  • Published : 2006.09.01

Abstract

Soyasaponins $A_1$, DDMP-conjugated group B soyasaponins ${\alpha}g\;and\;{\beta}g$, non-DDMP counterpart soyasaponin I, II+III, and DDMP moiety were quantified in the large-, midium-, and small-seed soybean varieties. Protein contents were ranged from 38.1% to 41.8%, and oil contents were ranged from 15.5% to 18.9%, respectively. Oil contents in the large-seed varieties were significantly higher than those of medium- and small-seed varieties. Among detected soyasaponin peaks, ${\beta}g$ was a major soyasaponin in DDMP-conjugated group B soyasaponins followed by soyasaponin I, DDMP moiety and $A_1$. Soyasaponin concentration among different seed size soybean varieties. The soyasaponin concentration of mediumseed ($4014.5{\mu}g/g$) was slightly higher than those of largeseed ($3755.0{\mu}g/g$) and small-seed varieties ($3620.3{\mu}g/g$), however, the differences was statistically not significant. The composition rates of soyasaponins in the large-size seeds were 9.4% of soyasaponin $A_1$, 26.5% of DDMP-conjugated soyasaponins, 49.9% of non-DDMP counterpart soyasaponins, and 14.2% of DDMP moiety, respectively. Similar results were observed in the composition ratios of middle- and small-size seeds. Oil content and C:N ratio showed the significant positive correlations with total soyasaponin concentration, while the 100-seed weight, fiber, and ash contents showed the negative correlations with total soyasaponin but statistically not significant. It was noted that protein contents didn't have any relationship with group A, group B, DDMP moiety, and total soyasaponin. This fact suggested that protein contents are not affects the variation of soyasaponin concentration.

Keywords

References

  1. Berhow, M. A., E. D. Wagner, S. F. Vaughn, and M. J. Plewa. 2000. Characterization and antimutagenic activity of soybean saponins. Mutat. Res. 448 : 11-22 https://doi.org/10.1016/S0027-5107(99)00225-0
  2. Berhow, M. A., S. B. Kong, K. E. Vermillion, and S. M. Duval. 2006. Complete quantification of group A and group B soyasaponins in soybeans. J. Agric. Food Chem. 54 : 2035-2044 https://doi.org/10.1021/jf053072o
  3. Burrows, J. C., R. P. Keith, and G.R. Fenwick. 1987. Soyasaponin IV an additional monodesmosidic saponin isolated from soyabean. Phytochemistry 26(4) : 1214-1215 https://doi.org/10.1016/S0031-9422(00)82387-0
  4. Daveby, Y. D.; P. Aman, J. M. Betz, and S. M. Musser. 1998. Effect of storage and extraction on ratio of soyasaponin I to 2,3-dihydro- 2,5-dihydroxy-6-methyl-4-pyrone-conjugated soyasaponin I in dehulled peas (Pisum sativum L). J. Sci. Food Agric. 78 : 141-146 https://doi.org/10.1002/(SICI)1097-0010(199809)78:1<141::AID-JSFA169>3.0.CO;2-6
  5. Fang, N. B., S. G. Yu, and T. M. Badger. 2004. Comprehensive phytochemical profile of soy protein isolate. J. Agric. Food Chem. 2004, 52 : 4012-4020 https://doi.org/10.1021/jf049842y
  6. Fenwick, D. E. and D. Oakenfull, D. 1983. Saponin content of food plants and some prepared foods. J. Sci. Food Agric. 34 : 186-191 https://doi.org/10.1002/jsfa.2740340212
  7. Hu, J., S. O. Lee, S. Hendrich, and P. A. Murphy. 2002. Quantification of the group B soyasaponins by high-performance liquid chromatography. J. Agric. Food Chem. 50 : 2587-2594 https://doi.org/10.1021/jf0114740
  8. Hubert, J., M. Berger, and J. Dayde. 2005. Use of a Simplified HPLC-UV Analysis for Soyasaponin B Determination: Study of Saponin and Isoflavone Variability in Soybean Cultivars and Soy-Based Health Food Products. J. Agric. Food Chem. 53 : 3923-3930 https://doi.org/10.1021/jf047828f
  9. Kim, Y. H. 2003. Biological Activities of Soyasaponins and Their Genetic and Environmental Variations in Soybean. Korean J. Crop Sci. 48(S) : 49-57
  10. Kinjo, J., M. Imagire, M. Udayama, T. Arao, and T. Nohara. 1998. Struture- hepatoprotective relationships study of soyasaponins I-IV having soyasapogenogenol B as aglycone. Planta Med. 64 : 233-236 https://doi.org/10.1055/s-2006-957416
  11. Kitagawa, I., T. Taniyama, Y. Nagahama, K. Okubo, F. Yamauchi, M. and Yoshikawa. 1988. Saponin and sapogenol. XLII. Structures of acetyl-soyasaponins A1, A2, and A3, astringent partially acetylated bisdesmosides of soyasapogenol A, from American soybean, the seeds of Glycine max Merrill. Chem. Pharm. Bull. 36 : 2819-2828 https://doi.org/10.1248/cpb.36.2819
  12. Kurosawa, Y., H. Takahara, and M. Shiraiwa. 2002. UDP-glucuronic acid: soyasapogenol glucuronosyltransferase involved in saponin biosynthesis in germinating soybean seeds. Planta 215(4) : 620-629 https://doi.org/10.1007/s00425-002-0781-x
  13. Miyao, H., T. Arao, M. Udayama, J. Kinjo, and T. N. T. Kaika. 1998. Saponin III and Soyasaponin I, major triterpene saponins of abrus cantoneiensis act on GOT and GPT: influence of transaminase elevation of rat liver cells concomitantly exposed to CCI4 for one hour. Planta Med. 64 : 5-7 https://doi.org/10.1055/s-2006-957355
  14. Oakenfull, D. G. and G. S. Sidhu. 1990. Could saponins be a useful treatment for hypercholesterolemia? Eur. J. Clin. Nutr. 44 : 79-88
  15. Okubo, K. and Y. Yoshiki. 1996. Oxygen-radical-scarvenging activity of DDMP-conjugated saponins and physiological role in leguminous plant. In Saponins Used in Food and Agriculture Waller, G. R., Yamasaki, K., Eds.; Plenum Press: New York, pp.141-154
  16. Okubo, K., M. Iijima, Y. Kobayashi, M. Yoshikoshi, T. Uchida, and S. Kudou. 1992. Components responsible for the undesirable taste of soybean seeds. Biosci., Biotechnol., Biochem. 56 : 99-103 https://doi.org/10.1271/bbb.56.99
  17. Okubo, K., S. Kudou, T. Uchida, Y. Yoshiki, M. Yoshikoshi, and M. Tonomura. 1994. Soybean saponin and isoflavonoids, structure and antiviral activity against human immunodeficiency virus in vitro. ACS Symp. 547 : 332-339
  18. Porter, S. M. 1996. Overview of proposed mechanisms for the hypocholesterolemic effect of soy. J. Nutr. 125: 717S-724S
  19. Rao, A. V. and M. K. Sung. 1995. Saponins as anticarcinogens. J. Nutr. 125 : 171S-174S
  20. Rupasinghe, H. P. V., C. J. C. Jackson, V. Poysa, V.; C. Di Berardo, J. D. Bewley, and J. Jenkinson. 2003. Soyasapogenol A and B distribution in soybean (Glycine max L. Merr.) in relation to seed physiology, genetic variability, and growing location. J. Agric. Food Chem. 51 : 5888-5894 https://doi.org/10.1021/jf0343736
  21. Ruzicka L. 1953. The isoprene rule and the biogenesis of terpenic compounds. Experientia. 9 : 357-367 https://doi.org/10.1007/BF02167631
  22. Shiraiwa, M., S. Kudo, M. Shimoyamada, K. Harada, and K. Okubo. 1991. Composition and structure of group A saponin in soybean seed. Agric. Biol. Chem. 55 : 315-322 https://doi.org/10.1271/bbb1961.55.315
  23. Shiraiwa, M.; K. Harada, and K. Okubo. 1991. Composition and structure of 'Group B Saponin' in soybean seed. Agric. Biol. Chem. 55 : 911-917 https://doi.org/10.1271/bbb1961.55.911
  24. Tsukamoto, C., A. Kikuchi, S. Kudou, K. Harada, K. Kitamura, and K. Okubo. 1992. Group a acetyl saponin-deficient mutant from the wild soybean. Phytochemistry, 31(12) : 4139-4142 https://doi.org/10.1016/0031-9422(92)80429-I
  25. Tsukamoto, C., S. Shimada, K. Igita, S. Kudou, M. Kokubun, K. Okubo, and K. Kitamura. 1995. Factors affecting isoflavone content in soybean seeds: Changes in isoflavones, saponins, and composition of fatty acids at different temperatures during seed development. J. Agric. Food Chem. 43 : 1184-1192 https://doi.org/10.1021/jf00053a012
  26. Van Soest, P.J., J.B. Robertson, and B.A. Lewis. 1991. Methods for dietary fiber, neutral detergent fiber, and nonstarch polysaccharides in relation to animal nutrition. J. Dairy Sci. 74 : 3583-3597 https://doi.org/10.3168/jds.S0022-0302(91)78551-2
  27. Yoshiki, Y., S. Takagi, M. Watanabe, and K. Okubo. 2005. Fractionation of soybean functional glycosides from soy-waste based on the chemical reaction of soyasaponin ${\beta}g$. Food Chem. 93 : 591-597 https://doi.org/10.1016/j.foodchem.2004.10.042