Guaiane Sesquiterpenoids from Torilis japonica and Their Cytotoxic Effects on Human Cancer Cell Lines

  • Park Hye Won (College of Pharmacy, Woosuk University) ;
  • Choi Sang-Un (Korea Research Institute of Chemical Technology) ;
  • Baek Nam-In (Graduate School of Biotechnology & Plant Metabolism Research Center) ;
  • Kim Sung-Hoon (Graduate School of East-West Medical Science, KyungHee University) ;
  • Eun Jae Soon (College of Pharmacy, Woosuk University) ;
  • Yang Jae Heon (College of Pharmacy, Woosuk University) ;
  • Kim Dae Keun (College of Pharmacy, Woosuk University)
  • Published : 2006.02.01

Abstract

A new compound 2 and two known guaiane-type sesquiterpenoids were isolated from the methylene chloride-soluble fraction of the methanolic extract of the fruits of Torilis japonica (Umbelliferae) through repeated silica gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as torilin (1), 11-acetoxy-8-angeloyloxy-$1{\beta}$-hydroxy-4-guaien-3-one ($1{\beta}$-hydroxytorilin, 2), and 11-acetoxy-8-angeloyloxy-$1{\alpha}$-hydroxy-4-guaien-3-one ($1{\alpha}$-hydroxytorilin, 3) by spectroscopic analysis. Compounds 1-3 exhibited cytotoxicity against human A549, SK-OV-3, SK-MEL-2, and HCT15 tumor cells.

Keywords

References

  1. Itokawa, H., Matsumoto, H., and Mihashi, S., Constituents of Torilis japonica D. C. I. Isolation and optical purity of germacra-4(15), 5(E), $10(14)-trien-1{\beta}-ol$. Chem. Pharm. Bull., 31, 1743-1745 (1983a) https://doi.org/10.1248/cpb.31.1743
  2. Itokawa, H., Matsumoto, H., and Mihashi, S., Isolation of oppositane- and cycloeudesmane-type sesquiterpenoids from Torilis japonica D. C. Chem. Lett., 1253-1256 (1983b)
  3. Itokawa, H., Matsumoto, H., Mizuno, K., Watanabe, K., and Morita, H., Structures of torilolide and oxytorilolide; novel germacranolides from Trilis japonica (Houtt.) D. C. Chem. Pharm. Bull., 34, 4682-4686 (1986) https://doi.org/10.1248/cpb.34.4682
  4. Kang, S. S., Lee, E. B., Kim, T. H., Kim, K. R., and Jung, J. H., The NMR assignment of Torilin from Torilis japonica. Arch. Pharm. Res., 17, 284-286 (1994) https://doi.org/10.1007/BF02980463
  5. Kim, S. E., Kim, Y. H., Kim, Y. C., and Lee, J. J., Torilin, a sesquiterpene from Torilis japonica, reverses multidrugresistance in cancer cells. Planta Med., 64, 332-334 (1998) https://doi.org/10.1055/s-2006-957445
  6. Kim, M. S., Lee, Y. M., Moon, E-J., Kim, S. E., Lee, J. J., and Kim, K. W., Anti-angiogenic activity of torilin, a sesquiterpene compound isolated from Torilis japonica. Int. J. Cancer, 87, 269-275 (2000) https://doi.org/10.1002/1097-0215(20000715)87:2<269::AID-IJC19>3.0.CO;2-W
  7. Kitajima, J., Suzuki, N., Satoh, N., and Watanabe, M., Sesquiterpenoids of Torilis japonica fruit. Phytochemistry, 59, 811- 815 (2002) https://doi.org/10.1016/S0031-9422(02)00025-0
  8. Kitajima, J., Suzuki, N., and Tanaka, Y., Guaiane-type sesquiterpenoid glycosides from Torilis japonica. Chem. Pharm. Bull., 46, 1743-1747 (1998) https://doi.org/10.1248/cpb.46.1743
  9. Lee, E. B., Cho, S. I., Kang, S. S., Kim, K. R., and Kim, T. H., Isolation of torilin from Torilis japonica fruit and its analgesic and anti-inflammatory activities. Kor. J. Pharmacogn., 30, 137-144 (1999)
  10. Lee, W. T., Coloured standard illustrations of Korean plants: Academy, Seoul, p. 263, (1996)
  11. Oh, H., Kim, J. S., Song, E. K., Cho, H., Kim, D. H., Park, S. E., and Kim, Y. C., Sesquiterpenes with hepatoprotective activity from Cnidium monnieri on tacrine-induced cytotoxicity in Hep G2 cells. Planta Med., 68, 748-749 (2002) https://doi.org/10.1055/s-2002-33796
  12. Park, W. S., Son, E. D., Nam, G. W., Kim, S. H., Noh, M. S., Lee, B. G., Jang, J. S., Kim, S. E., Lee, J. J., and Lee, C. H., Torilin from Torilis japonica, as a new inhibitor of testosterone $5{\alpha}$-reductase. Planta Med., 69, 459-461 (2003) https://doi.org/10.1055/s-2003-39717
  13. Ryu, J. H. and Jeong, Y. S., A new guaine type sesquiterpene from Torilis japonica. Arch. Pharm. Res., 24, 532-535 (2001) https://doi.org/10.1007/BF02975160
  14. 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 Inst., 82, 1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107
  15. Sung, C. K., Kimura, T., But, Paul, P. H., and Guo, J. X., International collation of traditional and folk medicine: Vol. 3. World scientific, Singapore, pp. 101-102, (1998)