Sesquiterpenoids and diarylheptanoids from Nidus vespae and their inhibitory effects on nitric oxide production

Chem Biodivers. 2011 Dec;8(12):2270-6. doi: 10.1002/cbdv.201000366.

Abstract

Two coriamyrtin-type sesquiterpenes, fengfangin A (1) and tutin (2), and six diarylheptanoids, namely alnusone (3), centrolobol (4), muricarpone B (5), 1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptan-3-one (6), (3S)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptan-3-ol (7), and (3S)-1-(4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)heptan-3-ol (8), were isolated from the 95% EtOH extract of nidus vespae, the nest of Polistes species. Their structures were identified by spectroscopic methods. Compounds 1 and 8 are new products. The absolute configuration of 1 was determined by single-crystal X-ray diffraction analysis using Flack parameter. The biological tests showed that compounds 5, 6, and 8 could inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells with IC(50) values in the range of 13-17 μM, whereas the sesquiterpenes were inactive in this assay (>25 μM). In addition, the ecological significance of the presence of neurotoxic sesquiterpene lactones in nidus vespae is briefly discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Cell Line
  • Diarylheptanoids / chemistry
  • Diarylheptanoids / isolation & purification*
  • Diarylheptanoids / pharmacology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Medicine, Chinese Traditional
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Nitric Oxide / adverse effects*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Wasps / chemistry*
  • Wasps / growth & development

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Diarylheptanoids
  • Sesquiterpenes
  • Nitric Oxide