Pseudoguaianelactones A-C: three unusual sesquiterpenoids from Lindera glauca with anti-inflammatory activities by inhibiting the LPS-induced expression of iNOS and COX-2

Chem Commun (Camb). 2020 Feb 4;56(10):1517-1520. doi: 10.1039/c9cc09159a. Epub 2020 Jan 10.

Abstract

The pseudoguaianelactones A (1) and B (2), two novel sesquiterpene lactones with an unprecedented [5,7,7] ring system featuring an α-methylene-γ-lactone moiety, together with a new pseudoguaianelactone C (3) were isolated from the roots of Lindera glauca. Pseudoguaianelactones A-C (1-3) inhibited nitric oxide (NO) production, with IC50 values ranging from 1.38 to 4.00 μM. Moreover, all compounds significantly suppressed the production of pro-inflammatory mediators (TNF-α, IL-6, IL-1β and PGE2) and the protein expression of the enzymes iNOS and COX-2.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology
  • Crystallography, X-Ray
  • Cyclooxygenase 2 / metabolism*
  • Cytokines / metabolism
  • Lindera / chemistry*
  • Lindera / metabolism
  • Lipopolysaccharides / pharmacology
  • Macrophages / cytology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Molecular Conformation
  • Nitric Oxide / metabolism
  • Nitric Oxide Synthase Type II / metabolism*
  • Plant Roots / chemistry
  • Plant Roots / metabolism
  • RAW 264.7 Cells
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Cytokines
  • Lipopolysaccharides
  • Sesquiterpenes
  • Nitric Oxide
  • Nitric Oxide Synthase Type II
  • Cyclooxygenase 2