Cytotoxic Constituents of the Leaves of Ixeris sonchifolia

  • Suh, Ji-Young (College of Pharmacy, Pusan National University) ;
  • Jo, Young-Mi (College of Pharmacy, Pusan National University) ;
  • Kim, Nam-Deuk (College of Pharmacy, Pusan National University) ;
  • Bae, Song-Ja (Department of Food and Nutrition, Silla University) ;
  • Jung, Jee-H. (College of Pharmacy, Pusan National University) ;
  • Im, Kwang-Sik (College of Pharmacy, Pusan National University)
  • Published : 2002.06.01

Abstract

The ethyl acetate extract of the leaves of Ixeris sonchifolia afforded two new and two known sesquiterpene lactone glucosides of the guaiane-type, together with a known alkenol glucoside. The known compounds were identified as ixerin Z (1), ixerin Z-6'-p-hydroxyphenylace-tate (2), and (Z)-3-hexen-1-ol-$\beta$-D-glucopyranoside (3), respectively. The structures of the new compounds were elucidated as 11, 13a-dihydroixerin Z [4, 3-hydroxy-2-oxo-guaia-1 (10), $3-dien-5{\alpha},6{\beta},7{\alpha},11{\beta}H-12,6-olide-3-O-{\beta}-D-glucopyranoside],{\;}and{\;}3,10{\$beta}-dihydroxy-2-oxo-guaia-3,11(13)-dien-1{\alpha},5{\alpha},6{\alpha},7aH-12,6-olide-10-O-{\beta}-D-glucopyranoside$ (5), respectively. The cytotoxicity of these compounds against human hepatocellular carcinoma cell (HepG2) and human melanoma cell (SK-MEL-2) was evaluated.

Keywords

References

  1. Feng, X.-Z., Xu, S.-X., and Dong, M., A New sesquiterpene lactone glucoside from Ixeris sonchifolia. J. Asian Nat. Prod. Res., 3, 247-251 (2001) https://doi.org/10.1080/10286020108040363
  2. Herz, W. and Govindan, S. V., Glycosidic Disecoeudesmanolides and Other Secosesquiterpene Lactones from Picradeniopsis Species. X-ray Analysis of Bahial, J. Org. Chem., 45, 3163-3172(1980) https://doi.org/10.1021/jo01304a005
  3. Isman, M. B., and Rodriguez, E., Larval Growth Inhibitors from Species of Parthenium. Phytochemistry, 22, 2709-2713(1983) https://doi.org/10.1016/S0031-9422(00)97677-5
  4. Ma, J.-Y., Wang, Z.-T., Xu, L.-S., Xu, G.-J, Kadota, S., and Namba, T., Sesquiterpene Lactones From Ixeris sonchifolia. Phytochemistry, 48, 201-203(1998) https://doi.org/10.1016/S0031-9422(97)01104-7
  5. Mizutani, K., Yuda, M., Tanaka, O., Saruwatari, Y-I., Fuwa, T., Jia, M.-R., Ling, Y-K., and Pu, X.-F., Chemical Studies on Chinese Traditional Medicine, Dangshen. I. Isolation of (Z)-3and(E)-2-Hexenyl-$\beta$-D-Glucosides. Chem. Pharm. Bull., 36,2689-2690 (1988) https://doi.org/10.1248/cpb.36.2689
  6. Mosmann, T., Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol. Methods, 65, 55-66 (1983) https://doi.org/10.1016/0022-1759(83)90303-4
  7. Nishimura, K., Miyase, T., Ueno, A., Noro, T., Kuroyanagi, M., and Fukushima, S., Sesquiterpene Lactones From Lactuca laciniata. Phytochemistry, 25, 2375-2379(1986) https://doi.org/10.1016/S0031-9422(00)81699-4
  8. Okunade, A. L., and Wiemer, D. F., Ant-Repellent Sesquiterpene Lactones from Eupatorium Quadrangularae. Phytochemistry, 24,1199-1201 (1985) https://doi.org/10.1016/S0031-9422(00)81100-0
  9. Seto, M., Miyase, T., and Fukushima, S., Sesquiterpene Lactones from Ixeris dentata NAKAI. Chem. Pharm. Bull., 34, 4170-4176(1986) https://doi.org/10.1248/cpb.34.4170
  10. Seto, M., Miyase, T., Umehara, K., Ueno, A., Hirano, Y., and Otani, N., Sesquiterpene Lactones from Cichorium endivia L. and C. intybus L., and Cytotoxic Activity. Chem. Pharm. Bull., 36, 2423-2429 (1988) https://doi.org/10.1248/cpb.36.2423
  11. Srivastava, R., Proksch, P., and Wray, V., Toxicity and Antifeedant Activity of a Sesquiterpene Lactone from Encelia against Spodoptera Littoralis. Phytochemistry, 29, 3445-3448 (1990) https://doi.org/10.1016/0031-9422(90)85254-D
  12. Stocklin, W., Waddell, T. G., and Geissman, T. A., Circular Dichroism and Optical Rotatory Dispersion of Sesquiterpene Lactones. Tetrahedron, 26, 2397-2410(1970) https://doi.org/10.1016/S0040-4020(01)92818-2