Cytotoxic Sesquiterpene Lactones from Saussurea calcicola

  • Choi, Sang-Zin (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University) ;
  • Choi, Sang-Un (Korea Research Institute of Chemical Technology) ;
  • Lee, Kang-Ro (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University)
  • Published : 2005.10.01

Abstract

Seven sesquiterpene lactones were isolated by the chromatographic separation of the MeOH extract of the aerial parts of Saussurea calcicola (Compositae). Their structures were determined spectroscopically to be cynaropicrin (1), arguerin B (2), cebellin F (3), 8${\alpha}$-hydroxy-11${\alpha}$, 13-dihydrozaluzanin C (4), desacylcynaropicrin (5), 3${\beta}$-hydroxy-8${\alpha}$-epoxymethylacriloiloxy-4(15), 10(14), 11(13)-trien-guaian-6, 12-olide (6), and kandavanolide (7). Compounds 1 and 2 showed significant cytotoxicity against five cultured human tumor cell lines with $ED_{50}$ values ranging from $0.23{\~}1.72\;{\mu}g/mL$.

Keywords

References

  1. Bensky, D. and Gamble, A., 'Chinese herbal medicine (Material medica)', Eastland Press, Seattle, pp. 339-340 (1986)
  2. Bohlmann, F. and Gupta, R. K., Further ineupatorolide like germacranolides from Inula cuspidate. Phytochemistry, 21, 157-160 (1982) https://doi.org/10.1016/0031-9422(82)80034-4
  3. Chhabra, B. R., Gupta, S., Jain, M., and Kalsi, P. S., Sesquiterpene lactones from Saussurea lappa. Phytochemistry, 49, 801-804 (1998) https://doi.org/10.1016/S0031-9422(97)00906-0
  4. Cho, J. Y., Baik, K. U., Jung, J. H., and Park, M. H., In vitro antiinflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappa. Eur. J. Pharm., 398, 399-407 (2000) https://doi.org/10.1016/S0014-2999(00)00337-X
  5. Dai, J., Zhao, C., Zhang, Q., Liu, Z. L., Zheng, R., and Yang, L., Taraxastane type triterpenoids from Saussurea petrovii. Phytochemistry, 58, 1107-1111 (2001) https://doi.org/10.1016/S0031-9422(01)00397-1
  6. Fernandez, I., Garcia, B., Grancha, F. J., and Pedro, J. R., Two guaianolides from Centaurea collina. Phytochemistry, 26, 2403-2405 (1987) https://doi.org/10.1016/S0031-9422(00)84731-7
  7. Fernandez, I., Garcia, B., Grancha, F. J., and Pedro, J. R., Sesquiterpene lactones, f1avonoids and coumarins from Centaurea collina. Phytochemistry, 28, 2405-2407 (1989) https://doi.org/10.1016/S0031-9422(00)97993-7
  8. Gonzalez, A. G., Amaro, J., Fraga, B. M., and Luis, J., 3-Oxo-6B-hydroxyolean-18-enoic acid from Orthopterygium huancuy. Phytochemistry, 22, 1828-1830 (1983) https://doi.org/10.1016/S0031-9422(00)80284-8
  9. Ha, T. J., Jang, D. S., Lee, J. R., Lee, K. D., Hwang, S. W., Jung, H. J., Nam, S. H., Park, K. H., and Yang, M. S., Cytotoxic effects of Sesquiterpene lactones from the flowers of Hemisteptia lyrata B. Arch. Pherm. Res., 26, 925-928 (2003) https://doi.org/10.1007/BF02980201
  10. Helal, A. M., Nakamura, N., Meselhy, M. R., EI-Fishawy, A.M., Hattori, M., and Mahran, G. H., Guaianolides from Centaurea scoparia. Phytochemistry, 45, 551-554 (1997) https://doi.org/10.1016/S0031-9422(96)00844-8
  11. Kisiel, W., 8-Epidesacylcynaropicrin from Crepis capillaris. Planta Med., 49, 246-247 (1983) https://doi.org/10.1055/s-2007-969861
  12. Li, Y. and Jia, Z. J., Guaianolides from Saussurea involucrate. Phytochemistry, 28, 3395-3397 (1989) https://doi.org/10.1016/0031-9422(89)80354-1
  13. Marco, J. A., Sanz, J. F., Albiach, R., Rustaiyan, A., and Habibi, Z., Bisabolene derivatives and sesquiterpene lactones from Cousinia species. Phytochemistry, 32, 395-400 (1993) https://doi.org/10.1016/S0031-9422(00)95002-7
  14. Marco, J. A., Sanz-Cervera, J. F., Yuste, A., and Oriola, M. C., Sesquiterpene lactones and dihydroflavonols from Andryala and Urospermum species. Phytochemistry, 36, 725-729 (1994) https://doi.org/10.1016/S0031-9422(00)89805-2
  15. Marco, J. A., Sanz-cervera, J. F., Garcia-liiso, V., Susanna, A., and Garcia-Jacas, N., Sesquiterpene lactones, lignans, and aromatic esters from Cheirolophus species. Phytochemistry, 37, 1101-1107 (1994) https://doi.org/10.1016/S0031-9422(00)89537-0
  16. Matsuda, H., Kageura, T., Inoue, Y., Morikawa, T., and Yoshikawa, M., Absolute stereostructures and syntheses of Saussureamines A, S, C, D, and E, amino acid-sesquiterpene conjugates with gastroprotective effect, from the roots of Saussurea lappa. Tetrahedron, 56, 7763-7777 (2000) https://doi.org/10.1016/S0040-4020(00)00696-7
  17. Rustaiyan, A., Niknejad, A., Zdero, C., and Bohlmann, F., A guaianolide from Centaurea benen. Phytochemistry, 20, 2427-2429 (1981) https://doi.org/10.1016/S0031-9422(00)82682-5
  18. Singhal, A. K., Chowdhury, P. K., and Sharma, R. P., Guaianolides from Tricholepis glaberrima. Phytochemistry, 21, 462-463 (1982) https://doi.org/10.1016/S0031-9422(00)95292-0
  19. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer lnst., 82, 1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107
  20. Youssef, D. and Frahm, A. W., Circular dichroism of C-7, C-6 trans-fused Gualanolides of Centaurea scoparia. Phtyochemistry, 41, 1107-1111 (1993)
  21. Zdero, C., Bohlmann, F., and Wasshausen, D. C., Guaianolides from Brachylaena species. Phtyohemistry, 30, 3810-3811 (1991) https://doi.org/10.1016/0031-9422(91)80119-L