Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Cytotoxic Effects of Sesquiterpene Lactones from the Flowers of Hemisteptia Iyrata B.

  • Ha, Tae-Joung (Institute of Agriculture and Life Science, Gyeongsang National University) ;
  • Jang, Dae-Sik (Graduate School of Molecular Life Sciences, Ewha Womans University) ;
  • Lee, Jong-Rok (Department of Agricultural Chemistry, Division of Applied Life Science, Gyeongsang National University) ;
  • Lee, Kyung-Dong (Institute of Agriculture and Life Science, Gyeongsang National University) ;
  • Lee, Jun (Department of Agricultural Chemistry, Division of Applied Life Science, Gyeongsang National University) ;
  • Hwang, Seon-Woo (Department of Agricultural Chemistry, Division of Applied Life Science, Gyeongsang National University) ;
  • Jung, Hwa-Jin (Department of Agricultural Chemistry, Division of Applied Life Science, Gyeongsang National University) ;
  • Nam, Sang-Hae (Department of Food Processing, Chinju National University) ;
  • Park, Ki-Hun (Department of Agricultural Chemistry, Division of Applied Life Science, Gyeongsang National University) ;
  • Yang, Min-Suk (Institute of Agriculture and Life Science, Gyeongsang National University)
  • Published : 2003.11.01
Download PDF
⟨ Previous Next ⟩

Abstract

Four guaia-12,6-olide type sesquiterpene lactones, aguerin B (1), 8$\alpha$-acetoxyzaluzanin C (2), cynaropicrin (3), and deacylcynaropicrin (4), were isolated from the flowers of Hemisteptia Iyrata Bunge. It is the first report on the isolation of compounds 1-4 from Hemisteptia species. All the isolates (1-4) were examined for their cytotoxic activity against SK-OV-3, LOX-IMVI, A549, MCF-7, PC-3, and HCT-15 human cancer cell lines.

Keywords

References

  1. Asakawa, Y. and Takemoto, T., Sesquiterpene lactones of Conocephalum conicum. Phytochemistry, 18, 285-288 (1979) https://doi.org/10.1016/0031-9422(79)80072-2
  2. Gonzalez, A. G., Bermejo, J., Cabrera, I., Massanet, G. M., Mansilla, H., and Galindo, A., Two sesquiterpene lactones from Centaurea canariensis. Phytochemistry, 17, 955-956 (1978) https://doi.org/10.1016/S0031-9422(00)88655-0
  3. Grippo, A. A., Hall, I. H., Kiyokawa, H. Muraoka, O., Shen, Y. C., and Lee, K. H., The cytotoxicity of helenalin, its mono and difunctional esters, and related sesquiterpene lactones in murine and human tumor cells. Drug Design Discovery, 8, 191-206 (1992)
  4. Ha, T. J., Hwang, S. W., Jung, H. J., Park, K. H., and Yang, M. S., Apigenin, tyrosinase inhibitor from the flowers of Hemisteptia lyrata Bunge. Agric. Chem. Biotechnol., 45, 170-172 (2002a)
  5. Ha, T. J., Jang, D. S., Lee, K. D., Lee, J. R., Park, K. H., and Yang, M. S., Studies on the constituents from the flowers of Hemisteptia lyrata Bunge II. Kor. J. Pharmacogn., 33, 92-95 (2002b)
  6. Ha, T. J., Yang, M. S., Pak, Y. B., Lee, J. R., Lee, K. D., Kim, H. M., and Park, K. H., New guaiane-type sesquiterpene lactones from Hemisteptia lyrata Bunge. Heterocycles, 57, 151-155 (2002c) https://doi.org/10.3987/COM-01-9387
  7. Ha, T. J., Park, K. H., Jang, D. S., Lee, J. R., Park, K. M., and Yang, M. S., New sesquiterpene lactones from Hemisteptia lyrata bunge. Heterocycles, 60, 623-629 (2003) https://doi.org/10.3987/COM-02-9669
  8. Hall, I. H., Grippo, A. A., Lee, K. H., Chaney, S. G., and Holbrook, D. J., Effect of helenalin and bis(helenalinyl) malonate on nucleic acid protein synthesis in human KB carcinoma cells. Pharmaceu. Sci., 4, 509-514 (1987)
  9. Hall, I. H., Lee, K. H., and Eigebaly, S. A., Antitumor agents XXVII: Effects of helenalin on anaerobic and aerobic metabolism of ehrlich ascites cells. J. Pharm. Sci., 67, 552-554 (1978) https://doi.org/10.1002/jps.2600670430
  10. Hall, I. H., Lee, K. H. Starnes, C. O., Eigebaly, S. A., Ibka, T., Wu Y. S., Kimura, T., and Haruna, M., Antitumor agents XXX: Evaluation of alpha-methylene-gamma-lactone containing agents for inhibition of tumor qrowth, respiration, and nucleic acid synthesis. J. Pharm. Sci., 67, 1235-1239 (1978) https://doi.org/10.1002/jps.2600670912
  11. Hoffmann, H. M. R. and Rabe, J., Synthesis and biological activity of $\alpha$-methylene-$\gamma$-butyrolactones. Angew. Chem. Int. Ed. Engl., 24, 94-110 (1985) https://doi.org/10.1002/anie.198500941
  12. Jang, D. S., Yang, M. S., and Park, K. H., Sesquiterpen lactone from Hemisteptia lyrata. Planta Med., 64, 289-290 (1998) https://doi.org/10.1055/s-2006-957436
  13. Jang, D. S., Yang, M. S., Ha, T. J., and Park, K. H., Hemistepsins with cytotoxic activity from Hemisteptia lyrata, Planta Med., 65, 765-766 (1999) https://doi.org/10.1055/s-2006-960863
  14. Lee, K. H., Hall, I. H., Mar, E. C., Starnes, C. O., Elgebaly, S. A., Waddell, T. G., Hadgraft, R. I., Ruffner, C. G., and Weidner, I., Sesquiterpene antitumor agents: Inhibitors of cellula metabolism. Science, 196, 533-536 (1977) https://doi.org/10.1126/science.191909
  15. Merrill, G. B. and Stevens, K. L., Sesquiterpene lactones from Centaurea solstitialis. Phytochemstry, 24, 2013-2018 (1985) https://doi.org/10.1016/S0031-9422(00)83113-1
  16. Peoples Press. In Encyclopedia of the Traditional Chinese Materia Medica. p. 1458-1459. Shanghai, P. R. China (1977)
  17. Shehan, P., Storeng, R., Scudiero, D., Monks, A., Mcmahon, J., Vistica, D., Warren, J. T., Bokesh, H., Kenny, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107