Dimeric Cadinane Sesquiterpenoid Derivatives from Artemisia annua

Org Lett. 2018 Jan 19;20(2):453-456. doi: 10.1021/acs.orglett.7b03796. Epub 2018 Jan 4.

Abstract

Arteannoide A (1), an unusual cadinane dimer featuring a rare fused 6,8-dioxabicyclo[3.2.l]octan-7-one ring system, arteannoides B and C (2 and 3), two novel heterodimers incorporating a rearranged cadinene sesquiterpenoid and a phenylpropanoid, together with two new rearranged cadinene sesquiterpenoids 4 and 5, were isolated from Artemisia annua L. Their structures were determined by a combination of NMR spectroscopy, electronic circular dichroism calculations, and X-ray diffraction analyses. Compounds 2 and 3 showed inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 mouse macrophage cell lines with IC50 values of 4.5 and 2.9 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Artemisia annua*
  • Cell Line
  • Lipopolysaccharides
  • Mice
  • Molecular Structure
  • Nitric Oxide
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes

Substances

  • Lipopolysaccharides
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • cadinane
  • Nitric Oxide