Glycosylation of ent-kaurene derivatives and an evaluation of their cytotoxic activities

Chin J Nat Med. 2013 May;11(3):289-95. doi: 10.1016/S1875-5364(13)60031-X.

Abstract

Aim: To discover more active and water-soluble derivatives of tetracyclic diterpenoids containing an exo-methylene cyclopentanone or an α-methylenelactone moiety.

Methods: All of the key intermediates were synthesized from stevioside, and the target compounds were obtained through glycosylation of the 4-carboxyl group. The cytotoxicity of the target compounds against six human cancer cell lines, HepG2, Bel-7402, A549, U251, MCF-7 and MDA-MB-231, were evaluated by the MTT assay.

Results: Compound 1b was more effective than the positive control adriamycin against the HepG2, Bel-7402, A549, MCF-7, and MDA-MB-231 cell lines with IC50 values of 0.12, 0.91, 0.35, 0.08, and 0.07 μmol·L(-1), respectively. Moreover, compound 3c exhibited the most potent and selective cytotoxic activity against the HepG2 cell line (IC50, 0.01 μmol·L(-1)).

Conclusion: Compounds 1b and 3c could be considered as potential anticancer candidates for further study.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / toxicity*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Diterpenes, Kaurane / chemistry
  • Diterpenes, Kaurane / toxicity*
  • Drug Evaluation, Preclinical
  • Glycosylation
  • Humans
  • Molecular Structure

Substances

  • Antineoplastic Agents
  • Diterpenes, Kaurane
  • kaurene