Synthesis and cytotoxic activity of new betulin and betulinic acid esters with conjugated linoleic acid (CLA)

Nat Prod Commun. 2013 Apr;8(4):435-8.

Abstract

The synthesis of new ester derivatives of betulin (3a-c) and betulinic acid (4) with conjugated linoleic acid isomers (CLA; in a mixture of 43.4% 9c, 11t; 49.5% 10t, 12c; 7.1% other isomers) is presented. Esterification was carried out with N,N'-dicyclohexylcarbodiimide (DCC) as the coupling agent in the presence of 4-dimethylamino-pyridine (DMAP) in dichloromethane (or pyridine). The in vitro cytotoxic effect of betulin (1), betulinic acid (2), a mixture of CLA isomers and their derivatives (3a-c, 4) was examined using the MTT assay against four cancer cell lines (P388, CEM/C2, CCRF/CEM and HL-60) and the SRB assay on the HT-29 cell line. Ester 4 was the most active among the esters synthesized against the CEM/C2 cell line with an ID50 value 16.9 +/- 6.5 microg/mL. Betulin (1), betulinic acid (2) and CLA were the most active agents against the cancer cell lines studied.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Betulinic Acid
  • Cell Line, Tumor
  • Humans
  • Linoleic Acids, Conjugated / chemical synthesis*
  • Linoleic Acids, Conjugated / chemistry
  • Linoleic Acids, Conjugated / pharmacology
  • Mice
  • Pentacyclic Triterpenes
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry
  • Triterpenes / pharmacology

Substances

  • Antineoplastic Agents
  • Linoleic Acids, Conjugated
  • Pentacyclic Triterpenes
  • Triterpenes
  • betulin
  • Betulinic Acid