Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Chemical Modification of Alisol B 23-acetate and Their Cytotoxic Activity

  • Lee, Sang-Myung (Korea Research Institute of Bioscience and Biotechnology) ;
  • Min, Byung-Sun (Korea Research Institute of Bioscience and Biotechnology) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University)
  • Published : 2002.10.01
Download PDF
⟨ Previous Next ⟩

Abstract

The twelve-protostane analogues were synthesized from alisol B 23-acetate and assessed for their in vitro antitumor activity against six different human and murine tumor cell lines. Of the compounds synthesized, 23S-acetoxy-24R(25)-epoxy-11$\beta$,23S-dihydroxyprotost-13(17)-en-3-hy-droxyimine (12) exhibited significant cytotoxic activities against A549, SK-OV3, B16-F10, and HT1080 tumor cells with $ED_{50}/$ values of 10.0, 8.7 ,5.2, and 3.1 ${\mu}g$/ml, respectively. Furthermore, 23S-acetoxy-13(17),24R(25)-diepoxy-11$\beta$-hydroxyprotost-3-one (5), 13(17),24R(25)-diepoxy-11$\beta$, 23S-dihydroxyprotostan-3-one (6), 24R,25-epoxy-11$\beta$,23S-dihydroxyprotost-13(17)-en-3-one (7), and 11$\beta$,23S,24R,25-tetrahydroxyprotost-13(17)-en-3-one (9) showed moderate cytotoxic activities against 816-F10 and HT1080 tumor cells. These results mean that a hydroxyimino group at C-3 position in the protostane-type terpene enhances cytotoxic activity.

Keywords

References

  1. Chen H. W., Hsu M. J., Chien C. T., Huang H. C., Effect of alisol B acetate, a plant triterpene, on apoptosis in vascular smooth muscle cell and lymphocytes. Eur. J. Pharmacol., 419, 127-138 (2001) https://doi.org/10.1016/S0014-2999(01)00983-9
  2. Kwon B. M., Lee S. H., Choi S. U., Park S. H., Lee C. O., Cho Y. K., Sing N. D., Bok S. H., Synthesis and in vitro cytotoxicity of cinnamaldehydes to human solid tumor cells. Arch. Pharm. Res., 21, 147-152 (1988) https://doi.org/10.1007/BF02974019
  3. Lee S. M., Kho Y. H., Min B. S., Kim J. H., Na M. K., Kang S. J., Maeng H. Y., Bae K. H., Cytotoxic triterpenoides from Alismatis Rhizoma. Arch. Pharm. Res., 24, 524-526 (2001) https://doi.org/10.1007/BF02975158
  4. Matsuda H., Kageura T., Toguchida I., Murakami T., Kishi A., Yoshikawa M., Effect of sesquiterpenes and triterpenes from the Rhizome of Alisma oriental on nitric oxid production in lipopolysaccharide-activated macrophages. Bioorg. Med. Chem. Lett., 9, 3081-3086(1999) https://doi.org/10.1016/S0960-894X(99)00536-3
  5. Murata T., Shinohara M., Miyamoto M., Biological-active triterpenes of Alismatis Rhizoma. Chem. Pharm. Bull., 18, 1369-1384 (1970) https://doi.org/10.1248/cpb.18.1369
  6. Skehan P., Storeng S., Studiero D., Monke A., McMahon J., Vistica D., Waren J. 1., Bodesh H., Kenny, S., Boyd M. R., New colorimetric cytotoxity assay for anticancer-drug screening.Natl. Cancer Inst., 82, 1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107