Di- and sesqui-terpenoids isolated from the pods of Sindora sumatrana and their potential to inhibit lipopolysaccharide-induced nitric oxide production

Arch Pharm Res. 2004 Mar;27(3):291-4. doi: 10.1007/BF02980062.

Abstract

Activity-guided fractionation of the n-hexane and CHCl3-soluble fractions of Sindora sumatrana using a bioassay based on the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production by inducible nitric oxide synthase (iNOS) in murine macrophage RAW 264.7 cells led to the isolation of the known compound, (+)-7beta-acetoxy-15,16-epoxy-3,13(16),14-clerodatriene-18-oic acid (2) as an active constituent. In addition, a new trans-clerodane diterpenoid, (+)-2-oxokolavenic acid (1), together with six known compounds, (+)-3,13-clerodadiene-16,15-olide-18-oic acid (3), (+)-7beta-acetoxy-3,13-clerodadiene-16,15-olide-18-oic acid (4), (+)-7beta-acetoxy-16-hydroxy-3,13-clerodadiene-16,15-olide-18-oic acid (5), beta-caryophyllene oxide (6), clovane-2beta,9beta-diol (7), and caryolane-1,9beta-diol (8) were isolated and found to be inactive. The structure of compound 1 was determined using physical and spectroscopic methods such as 1D and 2D-NMR experiments. The known compounds 2-8 were identified by the spectroscopic data and by comparison with the published values. Of eight isolates (1-8), only compound 2 exhibited an iNOS inhibitory activity with IC50 value of 51.6 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology
  • Fabaceae*
  • Fruit
  • Lipopolysaccharides / pharmacology
  • Mice
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Nitric Oxide Synthase / antagonists & inhibitors
  • Nitric Oxide Synthase / metabolism
  • Nitric Oxide Synthase Type II
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Terpenes / chemistry
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology*

Substances

  • Enzyme Inhibitors
  • Lipopolysaccharides
  • Plant Extracts
  • Terpenes
  • Nitric Oxide
  • Nitric Oxide Synthase
  • Nitric Oxide Synthase Type II
  • Nos2 protein, mouse