Triterpenoids from Acanthopanax koreanum Root and Their Inhibitory Activities on NFAT Transcription

  • Cai, Xing-Fu (College of Pharmacy, Chungnam National University) ;
  • Lee, Im-Seon (College of Pharmacy, Chungnam National University) ;
  • Shen, Guanghai (College of Pharmacy, Chungnam National University) ;
  • Dat, Nguyen-Tien (College of Pharmacy, Chungnam National University) ;
  • Lee, Jung-Joon (College of Pharmacy, Chungnam National University) ;
  • Kim, Young-Ho (College of Pharmacy, Chungnam National University)
  • Published : 2004.08.01

Abstract

Two triterpenoids (1,4) and two triterpenoid glycosides (2,3) were isolated from the root of Acanthopanax koreanum (Araliaceae). Their structures were identified as impressic acid (1), acankoreoside A (2), 3-epi-betulinic acid 28-O-[(${\alpha}-L-rhamnopyranosyl(1{\rightarrow}4)-{\beta}-D-glucopyrano-syl(1{\rightarrow}6)]-{\beta}-D-glucopyranosyl]$ ester (3), and ursolic acid (4) by physicochemical and spectro-scopic methods. Of these compounds, impressic acid (1) exhibited a potent inhibitory activity against NFAT transcription factor ($IC_{50}:{\;}12.65{\;}{\mu\textrm{m}}$).

Keywords

References

  1. Bensky, D. and Gamble, A., Materia medica. Eastland press, Washington, pp. 161-162 (1986)
  2. Cai, X. F., Shen, G. H., Nguyen, T. D., Kang, O. H., Lee, Y. M., Lee, J. J., and Kim, Y. H., Inhibitory effect of kaurane type diterpenoids from Acanthopanax koreanum on TNF-${\alpha}$ secretion from trypsin-stimulated HMC-1 cells. Arch. Pharm. Res., 26, 731-734 (2003a) https://doi.org/10.1007/BF02976683
  3. Cai, X. F., Shen, G. H., Nguyen, T. D., Kang, O. H., Kim, J. A., Lee, Y. M., Lee, J. J., and Kim, Y. H., Inhibitory effectof TNF-${\alpha}$ and IL-8 secretion by pimarane-type diterpenoids from Acanthopanax koreanum. Chem. Pharm. Bull., 51, 605-607 (2003b) https://doi.org/10.1248/cpb.51.605
  4. Chang, S. Y., Yook, C. S., and Nohara, T., Two new lupane-triterpene glycosides from leaves of Acanthopanax koreanum. Chem. Pharm. Bull., 46, 163-165 (1998) https://doi.org/10.1248/cpb.46.163
  5. Han, S. B., Park, S. K., Ahn, H. J., Yoon, Y. D., Kim, Y. H., Lee, J. J., Lee, K. H., Moon, J. S., Kim, H. C., and Kim, H. M., Characterization of B cell membrane receptors of polysaccharide isolated from the root of Acanthopanax koreanum. Int. Immunopharmacol., 3, 683-691 (2003) https://doi.org/10.1016/S1567-5769(03)00056-0
  6. Jain, J., Loh, C., and Rao, A., Transcriptional regulation of the IL-2gene. Curr. Opin. Immunol., 7, 333-342 (1995) https://doi.org/10.1016/0952-7915(95)80107-3
  7. Jeong, T. S., Hwang, E. I., Lee, H. B., Lee, E. S., Kim,Y. K., Min, B. S., Bae, K. H., Bok, S. H., and Kim, S. U., Chitin synthase II inhibitory activity of ursolic acid, isolated from Crataegus pinnatifida. Planta Med., 65, 261-263 (1999) https://doi.org/10.1055/s-2006-960474
  8. Kim, J. Y. and Yang, K. S., Screening of antioxidant activity of Acanthopanax species in vitro. Yakhak Hoeji, 47, 361-364 (2003)
  9. Kim, Y. H., Chung, B. S., and Sankawa, U., Pimaradiene diterpenes from Acanthopanax koreanum. J. Nat. Prod., 51, 1080-1083 (1988) https://doi.org/10.1021/np50060a005
  10. Kim, Y. H., Ryu, J. H., and Chung, B. S., Diterpene glycoside from Acanthopanax koreanum. Kor. J. Pharmacogn., 21, 49-51 (1990)
  11. Lee, I. S., Dang, T. L. H., Lee, M. S., Kim, J. W., Na, D. S., and Kim, Y. H., NFAT transcription factor inhibitory constituents from Cnidium officinale. Nat. Prod. Sci., 8, 94-96 (2002)
  12. Lee, I. S., Lee, H. K., Nguyen, T D., Lee, M. S., Kim, J. W., Na, D. S., and Kim,Y. H., Lignans with inhibitory activity against NFAT transcription from Schisandra chinensis. Planta Med., 69, 63-64 (2003) https://doi.org/10.1055/s-2003-37024
  13. Lee, Y. N., Flora of Korea. Kyohaksa, Seoul, p. 544 (1996)
  14. Min, B. S., Kim, Y. H., Lee, S. M., Jung, J. H., Lee, S. J., Na, M. K., Lee, C. O., Lee, J. P., and Bae, K. H., Cytotoxic triterpenes from Crataegus pinnatifida. Arch. Pharm. Res., 23, 155-158 (2000) https://doi.org/10.1007/BF02975505
  15. Shin, K. H. and Lee, S., The chemistry of secondary products from Acanthopanax species and their pharmacological activities. Nat. Prod. Sci., 8, 111-126 (2002)
  16. Sung, T. V, Steglich, W., and Adam, G., Triterpene glycosides from Schefflera octophylla. Phylochem., 30, 2349-2356 (1991) https://doi.org/10.1016/0031-9422(91)83647-4
  17. Ty, P. D., Lischewski, M., Phiet, H. V., Preiss, A., Sung, T. V., Schmidt, J., and Adam, G., Two triterpenoid carboxylic acids from Acanthopanax trifoliatus. Phylochem., 23, 2889-2891 (1984) https://doi.org/10.1016/0031-9422(84)83035-6
  18. Yang, T. T., Sinai, P., Kitts, P. A., and Kain, S. R., Quantification of gene expression with a secreted alkaline phosphatase reporter system. Biotechniques, 23, 1110-1114 (1997).