Cassane- and norcassane-type diterpenes from Caesalpinia crista of Indonesia and their antimalarial activity against the growth of Plasmodium falciparum

J Nat Prod. 2005 May;68(5):706-10. doi: 10.1021/np0401720.

Abstract

The CH2Cl2 extract of the seed kernels of Caesalpinia crista, which exhibited promising antimalarial activity against Plasmodium berghei-infected mice in vivo, was examined and resulted in the isolation of seven new furanocassane-type diterpenes [caesalpinins C-G (1-5) and norcaesalpinins D and E (6, 7)] together with norcaesalpinins A-C (8-10) and 11 known compounds (norcaesalpinins A-C, 2-acetoxy-3-deacetoxycaesaldekarin e, caesalmin B, caesaldekarin e, caesalpin F, 14(17)-dehydrocaesalpin F, 2-acetoxycaesaldekarin e, 7-acetoxybonducellpin C, and caesalmin G). Their structures were determined on the basis of spectroscopic analysis. The isolated diterpenes showed significant dose-dependent inhibitory effects on Plasmodium falciparum FCR-3/A2 growth in vitro. Their IC50 values ranged from 90 nM to 6.5 microM, and norcaesalpinin E (7) showed the most potent inhibitory activity (IC50, 90 nM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology
  • Caesalpinia / chemistry*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Indonesia
  • Inhibitory Concentration 50
  • Mice
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Plasmodium berghei / drug effects
  • Plasmodium falciparum / drug effects
  • Seeds / chemistry

Substances

  • Antimalarials
  • Diterpenes