New antimycobacterial and antimalarial 8,9-secokaurane diterpenes from Croton kongensis

J Nat Prod. 2003 Jun;66(6):868-70. doi: 10.1021/np030067a.

Abstract

Two new 8,9-secokaurane diterpenes, ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione (1) and ent-8,9-seco-8,14-epoxy-7alpha-hydroxy-11beta-acetoxy-16-kauren-9,15-dione (2), together with two known compounds, ent-8,9-seco-7alpha-hydroxy-11beta-acetoxykaura-8(14),16-dien-9,15-dione (3) and ent-7beta-hydroxy-15-oxokaur-16-en-18-yl acetate, were isolated from Croton kongensis. This is the first report on the presence of 8,9-secokauranes in the plant genus Croton. Diterpenes 1-3 exhibited antimycobacterial activity with minimum inhibitory concentrations (MICs) of 25.0, 6.25, and 6.25 microg/mL, respectively, and possessed antimalarial activity with IC(50) ranges of 1.0-2.8 microg/mL. They also demonstrated comparable cytotoxicity toward the Vero (IC(50) ranged from 0.9 to 3.2 microg/mL), KB (IC(50) from 1.2 to 13.8 microg/mL), and BC cell lines (IC(50) from 1.1 to 2.2 microg/mL, except for compound 1, which was inactive against BC cells).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology
  • Croton / chemistry*
  • Diterpenes, Kaurane / chemistry
  • Diterpenes, Kaurane / isolation & purification*
  • Diterpenes, Kaurane / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • KB Cells
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Plasmodium falciparum / drug effects
  • Stereoisomerism
  • Thailand
  • Tumor Cells, Cultured / drug effects

Substances

  • Antimalarials
  • Diterpenes, Kaurane
  • ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione
  • ent-8,9-seco-8,14-epoxy-7alpha-hydroxy-11beta-acetoxy-16-kauren-9,15-dione