Uprolides N, O and P from the Panamanian Octocoral Eunicea succinea

Molecules. 2016 Jun 22;21(6):819. doi: 10.3390/molecules21060819.

Abstract

Three new diterpenes, uprolide N (1), uprolide O (2), uprolide P (3) and a known one, dolabellane (4), were isolated from the CH₂Cl₂-MeOH extract of the gorgonian octocoral Eunicea succinea, collected from Bocas del Toro, on the Caribbean coast of Panama. Their structures were determined using spectroscopic analyses, including 1D and 2D NMR and high-resolution mass spectrometry (HRMS) together with molecular modeling studies. Compounds 1-3 displayed anti-inflammatory properties by inhibiting production of Tumor Necrosis Factor (TNF) and Interleukin (IL)-6 induced by lipopolysaccharide (LPS) in murine macrophages.

Keywords: Eunicea succinea; anti-inflammatory; cembranolide diterpenes; uprolides.

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Diterpenes / administration & dosage
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Gene Expression Regulation / drug effects
  • Inflammation / chemically induced
  • Inflammation / drug therapy*
  • Inflammation / genetics
  • Interleukin-6 / biosynthesis
  • Interleukin-6 / genetics
  • Macrophages / drug effects*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Models, Molecular
  • Panama
  • Plant Extracts / chemistry
  • Tumor Cells, Cultured
  • Tumor Necrosis Factor-alpha / biosynthesis
  • Tumor Necrosis Factor-alpha / genetics

Substances

  • Diterpenes
  • Interleukin-6
  • Plant Extracts
  • Tumor Necrosis Factor-alpha
  • dolabellane