New ursane-type triterpene with NO production suppressing activity from Nauclea officinalis

J Asian Nat Prod Res. 2012;14(2):97-104. doi: 10.1080/10286020.2011.628839.

Abstract

Two new ursane-type triterpenes, named as 3β, 19α, 23, 24-tetrahydroxyurs-12-en-28-oic acid (1) and 2β, 3β, 19α, 24-tetrahydroxyurs-12-en-28-oic acid (2), together with two known triterpenoids, 3-oxo-urs-12-ene-27, 28-dioic acid (3) and quinovic acid-3-β-rhamnopyranoside (4), were isolated from the stems (with barks) of Nauclea officinalis. The structures of 1 and 2 were determined by the combined use of single-crystal X-ray diffraction and spectroscopic data analysis. The inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells were examined, and compound 1 was found to inhibit NO production, with the IC(50) value of 4.8 μM.

MeSH terms

  • Animals
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis*
  • Pentacyclic Triterpenes / chemistry
  • Pentacyclic Triterpenes / isolation & purification*
  • Pentacyclic Triterpenes / pharmacology*
  • Plant Bark / chemistry
  • Rubiaceae / chemistry*

Substances

  • 2beta,3beta,19alpha,24-tetrahydroxyurs-12-en-28-oic acid
  • Drugs, Chinese Herbal
  • Lipopolysaccharides
  • Pentacyclic Triterpenes
  • Nitric Oxide