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Soyasaponins from Soybean Flour Medium for the Liquid Culture of Ganoderma applanatum

  • Lee, So-Young (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Kim, Ju-Sun (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Shim, Sang-Hee (School of Biotechnology, Yeungnam University) ;
  • Kang, Sam-Sik (Natural Products Research Institute and College of Pharmacy, Seoul National University)
  • Received : 2011.07.11
  • Accepted : 2011.08.12
  • Published : 2011.10.20

Abstract

Two new unusual soyasaponins named 6"-O-methyldehydrosoyasaponin I(7) and desglucosylsoyasaponin $A_1$ (10) along with eight known saponins, dehydrosoyasaponin IV (1), dehydrosoyasaponin III (= impatienoside A) (2), soyasaponin III (3), dehydrosoyasaponin II (= soyasaponin Bg) (4), soyasaponin II (5), dehydrosoyasaponin I (= soyasaponin Be) (6), soyasaponin I (8), and kudzusaponin $SA_3$ (9), were isolated as their methyl esters and identified from the liquid culture of G. applanatum. Their structures were determined by chemical and spectroscopic analyses including 1D- and 2D-NMR as well as by comparison of their spectroscopic data with those of the reported in literatures. Although dehydrosoyasaponin IV was identified by LC-MS/MS method from soy protein isolate, this is the first report of the isolation of this compound. Dehydrosoyasaponin III (2) and kudzusaponin $SA_3$ (9) were also isolated for the first time from soybean. The presence of soyasaponins in Ganoderma species seems to be unusual feature. Thus, we presumed that compounds 1-10 might all be derived from the defatted soybean flour which was added to the culture medium as a nitrogen source.

Keywords

References

  1. Lee, S. Y.; Kim, J. S.; Lee, S.-H.; Kang, S. S. Nat. Prod. Res. 2011, 25, 1304. https://doi.org/10.1080/14786419.2010.503190
  2. Dinda, B.; Debnath, S.; Mohanta, B. C.; Harigaya, Y. Chem. Biodiv. 2010, 7, 2327. https://doi.org/10.1002/cbdv.200800070
  3. Kang, S. S. Triterpenoid Saponins; Seoul National University Press: Seoul, 1996.
  4. Li, W.; Bi, X. Y.; Wang, K.; Li, D. X.; Satou, T.; Koike, K. Phytochemistry 2009, 70, 816. https://doi.org/10.1016/j.phytochem.2009.03.022
  5. Kitagawa, I.; Wang, H. K.; Taniyama, T.; Yoshikawa, M. Chem. Pharm. Bull. 1988, 36, 153. https://doi.org/10.1248/cpb.36.153
  6. Park, S. Y.; Kim, J. S.; Lee, S. Y.; Bae, K. H.; Kang, S. S. Nat. Prod. Sci. 2008, 14, 281.
  7. Kitagawa, I.; Taniyama, T.; Murakami, T.; Yoshihara, M.; Yoshikawa, M. Yakugaku Zasshi 1988, 108, 547.
  8. Shiraiwa, M.; Harada, K.; Okubo, K. Agric. Biol. Chem. 1991, 55, 911. https://doi.org/10.1271/bbb1961.55.911
  9. Byun, J. H.; Kim, J. S.; Kang, S. S.; Son, K. H.; Chang, H. W.; Kim, H. P. Chem. Pharm. Bull. 2004, 52, 870. https://doi.org/10.1248/cpb.52.870
  10. Arao, T.; Kinjo, J.; Nohara, T.; Isobe, R. Chem. Pharm. Bull. 1995, 43, 1176. https://doi.org/10.1248/cpb.43.1176
  11. Iorizzi, M.; Bifulco, G.; de Riccardis, F.; Minale, L.; Riccio, R.; Zollo, F. J. Nat. Prod. 1995, 58, 10. https://doi.org/10.1021/np50115a002
  12. Voelter, W.; Breitmaier, E.; Rathbone, E. B.; Stephen, A. M. Tetrahedron 1973, 29, 3845. https://doi.org/10.1016/0040-4020(73)80204-2
  13. Fang, J.-M.; Wang, K.-C.; Cheng, Y.-S. Phytochemistry 1991, 30, 3383. https://doi.org/10.1016/0031-9422(91)83214-6
  14. Wang, B.-G.; Jia, Z.-J. Phytochemistry 1998, 49, 185. https://doi.org/10.1016/S0031-9422(97)01057-1
  15. Chludil, H. D.; Murray, A. P.; Seldes, A. M.; Maier, M. S. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, 2003; vol. 28, p 587.
  16. Seo, S.; Tomita, Y.; Tori, K.; Yoshimura, Y. J. Am. Chem. Soc. 1978, 100, 3331. https://doi.org/10.1021/ja00479a014
  17. Kang, J.; Badger, T. M.; Ronis, M. J. J.; Wu, X. J. Agric. Food Chem. 2010, 58, 8119. https://doi.org/10.1021/jf100901b
  18. Decroos, K.; Vincken, J.-P.; Heng, L.; Bakker, R.; Gruppen, H.; Verstraete, W. J. Chromatogr. A 2005, 1072, 185. https://doi.org/10.1016/j.chroma.2005.03.021
  19. Hu, J.; Lee, S.-O.; Hendrich, S.; Murphy, P. A. J. Agric. Food Chem. 2002, 50, 2587. https://doi.org/10.1021/jf0114740
  20. Fang, N.; Yu, S. G.; Badger, T. M. J. Agric. Food Chem. 2004, 52, 4012. https://doi.org/10.1021/jf049842y

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