LC-MS guided isolation of gracilistones A and B, a pair of diastereomeric sesquiterpenoids with an unusual tetrahydrofuran-fused tricyclic skeleton from Acanthopanax gracilistylus and their potential anti-inflammatory activities

Fitoterapia. 2018 Oct:130:265-271. doi: 10.1016/j.fitote.2018.09.012. Epub 2018 Sep 20.

Abstract

Gracilistones A (1) and B (2), two new eudesmane-type sesquiterpenoids with an unusual tetrahydrofuran-fused 6/6/5 tricyclic ring system, were obtained from Acanthopanax gracilistylus under the guidance of LC-MS investigation. Their structures and absolute configurations were assigned by extensive spectroscopic analyses and quantum calculation methods. Compounds 1 and 2 showed potent inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages, compared with the positive control L-NMMA. In addition, compounds 1 and 2 were also evaluated for their antioxidant (DPPH and ABTS•+) and xanthine oxidase (XO) inhibitory activities, and they exhibited weak inhibitory effects at 100 μM.

Keywords: Acanthopanax gracilistylus; Anti-inflammation; Anti-oxidant; Eudesmane-type sesquiterpenoid; LC-MS; Xanthine oxidase.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology*
  • China
  • Chromatography, Liquid
  • Eleutherococcus / chemistry*
  • Furans
  • Mass Spectrometry
  • Mice
  • Molecular Structure
  • Nitric Oxide / metabolism
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Roots / chemistry
  • RAW 264.7 Cells
  • Sesquiterpenes, Eudesmane / isolation & purification
  • Sesquiterpenes, Eudesmane / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Antioxidants
  • Furans
  • Phytochemicals
  • Sesquiterpenes, Eudesmane
  • Nitric Oxide
  • tetrahydrofuran