Synthesis of spirolactone-type diterpenoid derivatives from kaurene-type oridonin with improved antiproliferative effects and their apoptosis-inducing activity in human hepatoma Bel-7402 cells

Eur J Med Chem. 2013 Jan:59:322-8. doi: 10.1016/j.ejmech.2012.11.002. Epub 2012 Nov 21.

Abstract

A series of novel spirolactone-type diterpenoid derivatives of oridonin (12a-j) were designed and synthesized. All the target compounds showed improved anti-proliferative activity against a panel of human cancer cell lines and the most effective compound 12j was more potent than positive control Taxol in K562 and Bel-7402 cells with IC(50) values of 0.39 μM and 1.39 μM, respectively. The cellular mechanisms showed that compound 12j induced apoptosis at low micromolar concentrations in human hepatoma Bel-7402 cells. These results demonstrate that the spirolactone-type diterpenoid derivatives of oridonin have optimized growth inhibitory activity against cancer cells and interesting apoptosis-inducing ability.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects*
  • Cell Cycle / drug effects
  • Cell Line, Tumor
  • Diterpenes / chemical synthesis
  • Diterpenes / chemistry
  • Diterpenes / pharmacology
  • Diterpenes, Kaurane* / chemical synthesis
  • Diterpenes, Kaurane* / chemistry
  • Diterpenes, Kaurane* / pharmacology
  • Flow Cytometry
  • Humans
  • Inhibitory Concentration 50
  • Liver Neoplasms / drug therapy*
  • Models, Molecular
  • Paclitaxel / therapeutic use
  • Spironolactone / chemical synthesis
  • Spironolactone / chemistry
  • Spironolactone / pharmacology

Substances

  • Antineoplastic Agents
  • Diterpenes
  • Diterpenes, Kaurane
  • oridonin
  • Spironolactone
  • kaurene
  • Paclitaxel