Exploring the Bioactive Terpenoid Content of an Algerian Plant of the Genus Pulicaria: The ent-Series of Asteriscunolides

J Nat Prod. 2017 Jan 27;80(1):82-89. doi: 10.1021/acs.jnatprod.6b00717. Epub 2016 Dec 29.

Abstract

Chemical analysis of the chloroform extract of the aerial parts of the Algerian plant Pulicaria undulata exhibiting anti-inflammatory activity resulted in the isolation of 10 new humulene sesquiterpenoids, 1-10, belonging to the asteriscunolide family of compounds. The structure and relative configuration have been defined by NMR data, whereas the absolute configuration has been established by ECD analysis. Compounds 1-10 include enantiomers of the known asteriscunolides A-D and tetrahydroasteriscunolide previously reported from the genera Asteriscus and Nauplius. Compounds 1 and 10 showed in vitro anti-inflammatory activity by inhibiting heat-induced albumin denaturation with IC50 values of 23.76 and 220.42 μM.

MeSH terms

  • Asteraceae / chemistry*
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Molecular Structure
  • Monocyclic Sesquiterpenes
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification*
  • Pulicaria / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Terpenes / analysis
  • Terpenes / chemistry
  • Terpenes / isolation & purification*

Substances

  • Lactones
  • Monocyclic Sesquiterpenes
  • Plant Extracts
  • Sesquiterpenes
  • Terpenes
  • asteriscunolide D
  • humulene