Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
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Cytotoxity of Sesquiterpene Lactones from Leaves of Helianthus tuberosus L.

돼지감자로부터 분리된 Sesquiterpene Lactone의 세포독성

  • Received : 2011.12.12
  • Accepted : 2012.03.06
  • Published : 2012.03.31
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Abstract

The $CH_2Cl_2$ soluble part of the leaves of Helianthus tuberosus L. (Compositae) exhibited a potent cytotoxic activity against the cultured human tumor cell lines including A-549, SK-OV-3, SK-MEL-2, XF498 and HCT-15 in vitro. Bioassaydirected fractionation of the $CH_2Cl_2$ soluble part of this plant led to the isolation of four cytotoxic sesquiterpene lactones having ${\alpha}$-methylene-${\gamma}$-lactone ring in the molecule. On the basis of physical and spectral evidences, their structures were characterized as ${\Delta}^{4,15}$-isoatripliciolide tiglate (1), ${\Delta}^{4,15}$-isoatripliciolide methacrylate (2), budlein A isobutylate (3) and budlein A tiglate (4). The ${\Delta}^{4,15}$-isoatripliciolide tiglate (1) showed the most potent cytotoxic activity ($0.26{\mu}M<ED_{50}<2.16{\mu}M$) against all of the cell lines tested.

Keywords

References

  1. Oriental Healing Arts Institute (1985) Structure activity relationship analysis of chinese anticancer drugs and related plants, 10. Keats publing, Taiwan, R.O.C.
  2. Spring, O. (1991) Sesquiterpene lactones from Helianthus tuberosus. Phytochemistry 2: 519-522.
  3. Morimoto, H., Sanno, Y. and Oshio, H. (1966) The X-ray analysis of dihydroheliangine monochloroacetate. Tetrahedron 22: 3173-3179. https://doi.org/10.1016/S0040-4020(01)82296-1
  4. Gershenzon, J. and Mabry, T. J. (1984) Furanoheliangolides from Helianthus schweinitzii. Phytochemistry 23: 2557-2559. https://doi.org/10.1016/S0031-9422(00)84098-4
  5. Delgado, G., Vivar, A. R. and Herz, W. (1982) Sesquiterpene lactones from Viguiera species. Phytochemistry 21: 1305- 1308. https://doi.org/10.1016/0031-9422(82)80130-1
  6. Herz, W. and Kuma, N. (1980) Sesquiterpene lactones of Calea zacatechichi and C. urticifolia. Phytochemistry 19: 593-597. https://doi.org/10.1016/0031-9422(80)87022-1
  7. Skehan, P., Streng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenny, S. and Boyd, M. R. (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 82: 1107- 1112. https://doi.org/10.1093/jnci/82.13.1107
  8. Ryu, S. Y., Choi, S. U., Lee, C. O. and Zee, O. P. (1992) Antitumor activity of Psoralea corylifolia, Arch. Pharm. Res. 4: 356-359.
  9. Doskotch, R. W., Hufford, C. D. and Ei-Feraley, F. S. (1972) Further studies on the sesquiterpene lactones Tulipinolide and Epitulipinolide from Liriodendron tulipifera. J. Org. Chem. 37: 2740-2744. https://doi.org/10.1021/jo00982a025
  10. Kupchan, S. M., Eakin, M. A. and Thomas, A. M. (1971) Tumor inhibitors. 69. Structure-cytotoxicity relations among the sesquiterpene lactones. J. Med. Chem. 12: 1147-1152.
  11. Woerdenberg, H., Edwards, A., Bude, E. J., Malingre, T. M. and Koningst, A. W. T. (1987) Eupatoriopicrin-induced lipid peroxidation in liver and tumor tissue of the mouse. Biochem. Pharmacol. 38: 3115-3118.