Highly-oxygenated isopimarane-type diterpenes from Orthosiphon stamineus of Indonesia and their nitric oxide inhibitory activity

Chem Pharm Bull (Tokyo). 2003 Mar;51(3):268-75. doi: 10.1248/cpb.51.268.

Abstract

From the methanolic extract of Indonesian Orthosiphon stamineus, nine new highly-oxygenated isopimarane-type diterpenes [7-O-deacetylorthosiphol B (1), 6-hydroxyorthosiphol B (2), 3-O-deacetylorthosiphol I (3), 2-O-deacetylorthosiphol J (4), siphonols A-E (5-9)] have been isolated together with nine known diterpenes [orthosiphols H (10), K (11), M (12) and N (13); staminols A (14) and B (15); neoorthosiphols A (16) and B (17); norstaminol A (18)]. Their structures were determined based on the spectroscopic data. The isolated diterpenes inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophage-like J774.1 cells. Compounds 4-7, 9, 10, 14, and 17 showed inhibitory activities more potent (IC(50), 10.8-25.5 microM) than a positive control N(G)-monomethyl-L-arginine (L-NMMA; IC(50), 26.0 microM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / isolation & purification
  • Carboxylic Acids / pharmacology*
  • Cell Line
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Indonesia
  • Macrophages / cytology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / metabolism
  • Orthosiphon*
  • Oxygen / metabolism*
  • Phenanthrenes / chemistry
  • Phenanthrenes / isolation & purification
  • Phenanthrenes / pharmacology*
  • Plant Components, Aerial
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology

Substances

  • Carboxylic Acids
  • Diterpenes
  • Phenanthrenes
  • Plant Extracts
  • isopimaric acid
  • Nitric Oxide
  • Oxygen