Siphonols A-E: novel nitric oxide inhibitors from Orthosiphon stamineus of Indonesia

Bioorg Med Chem Lett. 2003 Jan 6;13(1):31-5. doi: 10.1016/s0960-894x(02)00854-5.

Abstract

From the methanolic extract of Orthosiphon stamineus, four novel highly oxygenated isopimarane-type diterpenes named siphonols A-D (1-4) and a novel biogenetically interesting norisopimarane-type diterpene named siphonol E (5) were isolated. The new compounds 1-3 and 5 showed more potent inhibitory effects on the nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophage-like J774.1 cells than a positive control N(G)-monomethyl-L-arginine (L-NMMA). Siphonols A-E (1-5) represent the first examples of isopimaranes oxygenated at C-20.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Cell Line
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Indonesia
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors*
  • Nuclear Magnetic Resonance, Biomolecular
  • Orthosiphon / chemistry*

Substances

  • Anti-Inflammatory Agents
  • Diterpenes
  • Lipopolysaccharides
  • siphonol A
  • siphonol E
  • Nitric Oxide