Macrocyclic anti-inflammatory diterpenes from the South China Sea soft coral Sinularia erecta and their isolation by combined column chromatography

J Chromatogr A. 2024 Nov 8:1736:465416. doi: 10.1016/j.chroma.2024.465416. Epub 2024 Oct 8.

Abstract

Eleven new macrocyclic casbane-type diterpenes, namely sinueracasbanones E-O (1-11), have been isolated from the South China Sea soft coral Sinularia erecta using combined column chromatography. The structures of new compounds were elucidated by extensive spectroscopic data analysis, the modified Mosher's method, X-ray diffraction analysis and quantum mechanical calculation methods. In bioassay, compounds 2, 5, 10 and 11 displayed interesting anti-inflammatory activities by the inhibition of lipopolysaccharide (LPS)-induced tumor necrosis factor (TNF)-α protein release with half maximal inhibitory concentration (IC50) values of 15.6, 7.1, 13.7 and 6.6 µM, respectively.

Keywords: Anti-inflammatory; Column chromatography; Marine natural products; Quantum mechanical calculation; Sinularia erecta; Soft coral.

MeSH terms

  • Animals
  • Anthozoa* / chemistry
  • Anti-Inflammatory Agents* / chemistry
  • Anti-Inflammatory Agents* / isolation & purification
  • Anti-Inflammatory Agents* / pharmacology
  • China
  • Diterpenes* / chemistry
  • Diterpenes* / isolation & purification
  • Diterpenes* / pharmacology
  • Lipopolysaccharides* / pharmacology
  • Macrocyclic Compounds / chemistry
  • Macrocyclic Compounds / isolation & purification
  • Macrocyclic Compounds / pharmacology
  • Mice
  • RAW 264.7 Cells
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Diterpenes
  • Anti-Inflammatory Agents
  • Lipopolysaccharides
  • Tumor Necrosis Factor-alpha
  • Macrocyclic Compounds