Anti-inflammatory Meroterpenoids from Baeckea frutescens

J Nat Prod. 2017 Aug 25;80(8):2204-2214. doi: 10.1021/acs.jnatprod.7b00042. Epub 2017 Jul 28.

Abstract

Frutescones H-R (1-11), new sesqui- or monoterpene-based meroterpenoids, were isolated from the aerial parts of Baeckea frutescens. Their structures and absolute configurations were established by means of spectroscopic analyses (HRESIMS, 1D and 2D NMR, and ECD), as well as single-crystal X-ray crystallography of 1, (-)-7, and 9. The anti-inflammatory activities of all isolates were evaluated by measuring their inhibitory effects on NO production in LPS-stimulated RAW 264.7 macrophages, and the structure-activity relationships of 1-11 are also discussed. Compound 8 exhibited anti-inflammatory activity with an IC50 value of 0.36 μM, which might be related to the regulation of the NF-κB signaling pathway via the suppression of p65 nuclear translocation and the consequent decrease of IL-6 and TNF-α.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology*
  • Crystallography, X-Ray
  • Interleukin-6 / chemistry
  • Interleukin-6 / metabolism*
  • Lipopolysaccharides / chemistry
  • Lipopolysaccharides / pharmacology*
  • Macrophages / chemistry
  • Macrophages / drug effects*
  • Molecular Structure
  • Myrtaceae / chemistry*
  • NF-kappa B / antagonists & inhibitors*
  • NF-kappa B / chemistry
  • Plant Components, Aerial / chemistry*
  • Signal Transduction / drug effects*
  • Structure-Activity Relationship
  • Terpenes / chemistry
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology*
  • Tumor Necrosis Factor-alpha / chemistry
  • Tumor Necrosis Factor-alpha / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Interleukin-6
  • Lipopolysaccharides
  • NF-kappa B
  • Terpenes
  • Tumor Necrosis Factor-alpha
  • frutescone