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Archives of Pharmacal Research

, Volume 26, Issue 7, pp 521–525 | Cite as

A new sesquiterpene hydroperoxide from the aerial parts ofAster oharai

  • Sang Zin Choi
  • Sung Ok Lee
  • Sang Un Choi
  • Kang Ro Lee
Article

Abstract

Phytochemical works on the aerial parts ofAster oharai (Compositae) led to the isolation of a new sesquiterpene hydroperoxide, 7α-hydroperoxy-3, 11-eudesmadiene (2) and seven known compounds, teucdiol B (1), α-spinasterol (3), oleanolic acid (4), α-spinasterol 3-O-β-D-glucopyranoside (5), methyl 3,5-di-O-caffeoyl quinate (6), 3,5-di-O-caffeoylquinic acid (7), 3,4-di-O-caffeoylquinic acid (8). The chemical structures of1–8 were established by chemical and spectroscopic methods. Compound2 showed cytotoxicity against cultured human tumor cell linesin vitro, SK-OV-3 (ovarian), SK-MEL-2 (skin melanoma), and HCT15 (colon) with ED50 values ranging from 3.86-17.21 ug/mL.

Keywords

Aster oharai Compositae Sesquiterpene hydroperoxide Quinic Acid Cytotoxicity 

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References

  1. Ahmad, V. U. and Rahman, A. U., Handbook of natural products data; Pentacyclic triterpenoids.Elsevier Science, 2, 111 (1994).Google Scholar
  2. Basnet, P., Matsushige, K., Hase, K., Kadota, S., and Namba, T., Four di-O-caffeoyl quinic acid derivatives from Propolis. Potent hepatoprotective activity in experimental liver injury models.Biol. Pharm. Bull., 19, 1479–1484 (1996).PubMedGoogle Scholar
  3. Bohlmann, F., Zeisberg, R., and Klien, E., Naturally occurring terpene derivatives. L. Carbon-13 NMR spectra of monoterpenes.Org. Mag. Res., 7, 426–432 (1975).CrossRefGoogle Scholar
  4. Choi, S. Z., Kwon, H. C., Choi, S. U., and Lee, K. R., Five New Labdane Diterpenes fromAster oharai.J. Nat. Prod., 65, 1102–1106 (2002).PubMedCrossRefGoogle Scholar
  5. Fraga, B. M., Hernandez, M. G., Mestres, T., Arteaga, J. M., and Perales, A., Eudesmane sesquiterpenes fromTeucrium heterophyllum. The X-ray structure of teucdiol A.Phytochemistry, 34, 1083–1086 (1993).CrossRefGoogle Scholar
  6. Fraga, B. M., Hernandez, M. G., Mestres, T., Terrero, D., and Arteaga, J. M., Nor-sesquiterpenes fromTeucrium heterophyllum.Phytochemistry, 39, 617–619 (1995).CrossRefGoogle Scholar
  7. Goad, L. J., Analysis of sterols. Blackie academic & professional, London, pp. 388 (1997).Google Scholar
  8. Iida, T., Ishikawa, T., Tamura, T., and Matumoto, T., Carbon-13 nuclear magnetic resonance spectroscopic evidence of chondrillasterol isolated from ground seed oil.Yukagaku, 29, 345–346 (1980).Google Scholar
  9. Iwahashi, H., Morishita, H., Osaka, N., and Kido, R., 3-O-Feruloyl-4-O-caffeoylquinic acid fromcoffee beans.Phytochemistry, 24, 630–632 (1985).CrossRefGoogle Scholar
  10. Kim, T. J., Wild flowers of Korea. Seoul, Korea, Kugilmedia, p. 232, (1996).Google Scholar
  11. Lee, K. R., Peroxide constituents in the natural product research.Kor. J. Pharmacogn., 22, 145–155 (1991).Google Scholar
  12. Lin, L. C., Kuo, Y. C., and Chou, C. J., Immunomodulatory principles ofDichrocephala bicolor.J. Nat. Prod., 62, 405–408 (1999).PubMedCrossRefGoogle Scholar
  13. Lu, T., Vargas, D., and Fischer, N. H., Sesquiterpenes fromBrintonia discoidea.Phytochemistry, 34, 737–742 (1993).CrossRefGoogle Scholar
  14. Mahato, S. B. and Kundu, A. P.,13C-NMR spectra of pentacyclic triterpenoids-a complilation and some salient features.Phytochemistry, 37, 1517–1575 (1994).CrossRefGoogle Scholar
  15. Oliveira, F. C., Ferreira, M. J. P., Nunez, C. V., Rodriguez, G. V., and Emerenciano, V. P.,13C-NMR spectroscopy of eudesmane sesquiterpenes.Prog. Nucl. Mag. Res. Sp., 7, 145 (2000).Google Scholar
  16. 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).PubMedCrossRefGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea 2003

Authors and Affiliations

  • Sang Zin Choi
    • 1
  • Sung Ok Lee
    • 1
  • Sang Un Choi
    • 1
    • 2
  • Kang Ro Lee
    • 1
  1. 1.Natural Products Laboratory, College of PharmacySungKyunKwan UniversitySuwonKorea
  2. 2.Korea Research Institute of Chemical TechnologyTaejeonKorea

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