Skip to main content
Log in

Cytotoxic triterpenes fromCrataegus pinnatifida

  • Research Articles
  • Medicinal Chemistry & Natural Products
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Bioassay-guided fractionation ofCrataegus pinnatifida (Rosaceae) gave two cytotoxic ursane-type triterpenes which were identified as uvaol (1) and ursolic acid (2) by physicochemical and spectroscopic methods. 3-Oxo-ursolic acid (3) was synthesized from ursolic acid (2) by Jones method. The cytotoxic activities of these compounds were tested against murine L1210 and human cancer cell lines (A549, SK-OV-3, SK-MEL-2, XF498, and HCT15)in vitro. Compounds1 and2 showed moderate cytotoxicities against L1210, whereas they showed weak activities against human cancer cell lines. However, compound3 exhibited potent cytotoxic activities both in murine and in human cancer cell lines.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Ahn, K. S., Hahm, M. S., Park, E. J., Lee, H. K. and Kim, I. H., Corosolic acid, isolated from the fruit ofCrataegus pinnatifida var.psilosa is a protein kinase C inhibitors as well as a cytotoxic agent.Planta Med., 64, 468–470 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Fieser, L. F. and Fieser, M., Reagent for organic synthesis, John Wiley and Sons, INC., Vol. 1, p. 142 (1967).

    Google Scholar 

  • Jeong, T. S., Hwang, E. I., Lee, H. B., Lee, E. S., Kim, Y. K., Min, B. S., Bae, K. H., Bok, S. H. and Kim, S. U., Chitin synthase II inhibitory activity of ursolic acid, isolated fromCrataegus pinnatifida, Planta Med., 65, 261–263 (1999).

    Article  PubMed  CAS  Google Scholar 

  • Kashiwada, Y., Wang, H. K., Nagao, T., Kitanaka, S., Yasuda, I., Fyjioka, T., Yamagishi, T., Cosentino, L. M., Kozuka, M., Okabe, H., Ikeshiro, Y., Hu, C. Q., Yeh, E. and Lee, K. H., Anti-HIV Activity of oleanolic acid, pomolic acid, and structurally related triterpenoids.J. Nat. Prod., 61, 1090–1095 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Kim, J. S. and Kim, I. H., Pharmaco-constituents ofCrataegus pinnatifida var.pubescens leaves.Yakhak Hoeji, 37, 193–197 (1993).

    CAS  Google Scholar 

  • Kwon, B. M., Lee, S. H., Choi, S. U., Park, S. H., Lee, C. O., Cho, Y. K., Sing, N. D., and Bok, S. H., Synthesis and in vitro cytotoxicity of cinnamaldehydes to human solid tumor cells. Arch. Pharm. Res., 21, 147–152 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Kwon, H. C., Lee, K. R. and Zee, O. P., Cytotoxic constituents ofPilea mongolica.Arch. Pharm. Res., 20, 180–183 (1997).

    Article  CAS  PubMed  Google Scholar 

  • Min, B. S., Jung, H. J., Lee, J. S., Kim, Y. H., Bok, S. H., Ma, C. M., Nakamura, N., Hattori, M. and Bae, K. H., Inhibitory effect of triterpenes fromCrataegus innatifida on HIV-1 Protease.Planta Med., 65, 374–375 (1999).

    Article  PubMed  CAS  Google Scholar 

  • Nakanishi, K., Goto, T., Ito, S., Natori, S., Nozoe, S.,Natural Products Chemistry Vol. 3, Kodansa, Tokyo, (1983).

    Google Scholar 

  • Oh, I. S. and Kim, I. H., Pharmaco-constituents ofCraetagus pinnatifida var.psilosa leaves (I).Yakhak Heoji, 37, 476–482 (1993).

    CAS  Google Scholar 

  • Oh, I. S., Whang, W. K. and Kim, I. H., Constituents ofCrataegus pinnatifida var.psilosa leaves (II).Arch. Pharm. Res., 17, 314–317 (1994).

    Article  CAS  Google Scholar 

  • Park, S. W., Yook, C. S. and Lee, H. K., Chemical components from the fruits ofCrataeguss pinnatifida var.psilosa.Kor. J. Pharmacog. 25, 328–335 (1994).

    CAS  Google Scholar 

  • Perry, L. M.,Medicinal Plants of East & Southeast Asia: Attributed Properties and Uses. The MIT Press, Massachusetts, pp 342 (1980).

    Google Scholar 

  • Skehan, P., Storeng, R., Schudiero, D. A., Monks, A., McMahan, J., Vistica, D., Warren, J. T., Bokesch, H., Kenny, S. and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer drug screening.J. Natl. Cancer Inst., 82, 1107–1112 (1990).

    Article  PubMed  CAS  Google Scholar 

  • Sohn, K. H., Lee, H. Y., Chung, H. Y., Young, H. S., Yi, S. Y. and Kim, K. W., Anti-angiogenic activity of triterpene acids.Cancer Letters, 94, 213–218 (1995).

    Article  PubMed  CAS  Google Scholar 

  • Tommasi, N. D., Simone, F. D., Pizza, C., Mahmood, N., Moore, P. S., Conti, C., Orsi, N. and Srein, M. L., Constituents ofEriobotrya japonica. A study of their antiviral properties.J. Nat. Prod., 55, 1067–1073 (1992).

    Article  PubMed  Google Scholar 

  • Trumbull, E. R., Bianchi, E., Eckert, D. J., Wiedhopf, R. M. and Cole, J. R., Tumor inhibitory agents fromVauquelinia corymbosa.J. Pharm. Sci., 65, 1407–1408 (1976).

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to KiHwan Bae.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Min, B.S., Kim, Y.H., Lee, S.M. et al. Cytotoxic triterpenes fromCrataegus pinnatifida . Arch Pharm Res 23, 155–158 (2000). https://doi.org/10.1007/BF02975505

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02975505

Key words

Navigation