Bulletin of the Korean Chemical Society

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Antioxidant Polyphenol Glycosides from the Plant Draba nemorosa

  • Published : 2007.05.20
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Abstract

Bioassay-directed fractionation of Draba nemorosa led to the isolation of two new phenolic glycosides, 1-O- (sinapoyl)-glucitol (2) and 1,3-disinapoylgentiobiose (5) along with five known phenolic glycosides (1, 3, 4, 6, and 7). Their structures were characterized based on spectroscopic methods (2D NMR, HRTOFMS, IR, and UV). The isolated compounds showed antioxidant activities (IC50) in the range of 14-98 mM which were estimated by DPPH radical-scavenging assay.

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References

  1. Sun, Y. Free Radic. Biol. Med. 1990, 8, 583 https://doi.org/10.1016/0891-5849(90)90156-D
  2. Henning, B.; Chow, C. K. Free Radic. Biol. Med. 1988, 4, 99 https://doi.org/10.1016/0891-5849(88)90070-6
  3. Buettner, R. G. Arch. Biochem. Biophys. 1993, 300, 535 https://doi.org/10.1006/abbi.1993.1074
  4. Dinis, T. C. P.; Maderia, V. M.; Almeida, L. M. Arch. Biochem. Biophys. 1994, 315, 161 https://doi.org/10.1006/abbi.1994.1485
  5. Ogata, M.; Hoshi, M.; Shimotohno, K.; Urano, S.; Endo, T. J. Am. Oil Chem. Soc. 1997, 74, 557 https://doi.org/10.1007/s11746-997-0180-3
  6. Hou, W. C.; Lin, R. D.; Cheng, K. T.; Hung, Y. T.; Cho, C. H.; Chen, C. H.; Hwang, S. Y.; Lee, M. H. Phytomedicine 2003, 10, 170 https://doi.org/10.1078/094471103321659898
  7. Chang, S. T.; Wu, J. H.; Wang, S. Y.; Kang, P. L.; Yang, N. S.; Shyur, L. F. J. Agric. Food Chem. 2001, 49, 3420 https://doi.org/10.1021/jf0100907
  8. Kahkonen, M. P.; Hopia, A. I.; Vuorela, H. J.; Rauha, J. P.; Pihlaja, K.; Kujala, T. S.; Heinonen, M. J. Agric. Food Chem. 1999, 47, 3954 https://doi.org/10.1021/jf990146l
  9. Grundt, H. H.; Elven, R.; Brochmann, C. Flora 2005, 200, 321 https://doi.org/10.1016/j.flora.2004.10.001
  10. Kim, K. W.; Shin, J. H.; Moon, J.; Kim, M.; Lee, J.; Park, M. C.; Lee, I. Mol. Cells. 2003, 16, 136
  11. Guil, J. L.; Rodriguez, G. I.; Torija, E. Plant Foods Hum. Nutr. 1997, 51, 99 https://doi.org/10.1023/A:1007988815888
  12. Kung, H. P.; Huang, W. Y. J. Am. Chem. Soc. 1949, 71, 1836 https://doi.org/10.1021/ja01173a089
  13. Regenbrecht, J.; Strack, D. Phytochemistry 1985, 24, 407 https://doi.org/10.1016/S0031-9422(00)80736-0
  14. Hosoya, T.; Yun, Y. S.; Kunugi, A. Tetrahedron 2005, 61, 7037 https://doi.org/10.1016/j.tet.2005.04.061
  15. Ikeya, Y.; Sugama, K.; Okada, M.; Mitsuhashi, H. Chem. Pharm. Bull. 1991, 39, 2600 https://doi.org/10.1248/cpb.39.2600
  16. Francisco, A.; Barberan, T.; Gil, M. I.; Ferreres, F.; Lorente, F. T. Phytochemistry 1992, 31, 3097 https://doi.org/10.1016/0031-9422(92)83452-5
  17. Dietz, H.; Winterhalter, P. Phytochemistry 1996, 42, 1005 https://doi.org/10.1016/0031-9422(96)00020-9
  18. Takaya, Y.; Kondo, Y.; Furukawa, T.; Niwa, M. J. Agric. Food Chem. 2003, 51, 8061 https://doi.org/10.1021/jf0346206
  19. Keith, R.; Casuscelli, F.; Colquhoun, I. J.; Rhodes, M. J. C. Phytochemistry 1997, 45, 1683 https://doi.org/10.1016/S0031-9422(97)00246-X
  20. Hase, T.; Hasegawa, K. Phytochemistry 1982, 21, 1021 https://doi.org/10.1016/S0031-9422(00)82408-5
  21. Sakushima, A.; Coskunt, M.; Maoka, T. Phytochemistry 1995, 40, 483 https://doi.org/10.1016/0031-9422(95)00276-D
  22. Blois, M. S. Nature 1958, 181, 1199 https://doi.org/10.1038/1811199a0

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