Uncommon terpenoids with anti-inflammatory activity from the Hainan soft coral Sinularia tumulosa

Bioorg Chem. 2020 Nov:104:104167. doi: 10.1016/j.bioorg.2020.104167. Epub 2020 Aug 25.

Abstract

One novel sesquiterpenoid containing an unprecedented eight-membered cyclic peroxide motif, sinulatumolin A (1), along with four new related terpenoids, namely sinulatumolins B-E (2-4 and 6), were isolated from South China Sea soft coral Sinularia tumulosa. The structures of all the isolates were elucidated by detailed spectroscopic analysis, chemical transformations, and single X-ray diffraction analysis. Compound 1 represents the first example of sesquiterpene bearing an eight-membered cyclic peroxide ring from soft coral. All the new compounds isolated were evaluated for their anti-inflammatory activity. Compounds 1, 3, 4 and 6 displayed significant TNF-α inhibitory activity being comparable with that of the positive control dexamethasone (IC50 = 8.7 μM), with IC50 values of 7.5, 2.6, 5.5, and 3.6 μM, respectively.

Keywords: Anti-inflammatory activity; Peroxide; Sinularia tumulosa; Terpenoids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Cell Line, Tumor
  • China
  • Dose-Response Relationship, Drug
  • Humans
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Structure
  • RAW 264.7 Cells
  • Structure-Activity Relationship
  • Terpenes / chemistry
  • Terpenes / isolation & purification
  • Terpenes / pharmacology*
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors*
  • Tumor Necrosis Factor-alpha / biosynthesis

Substances

  • Anti-Inflammatory Agents
  • Lipopolysaccharides
  • Terpenes
  • Tumor Necrosis Factor-alpha