Ximaoornatins A-C, Polyoxygenated Diterpenoids from the Hainan Soft Coral Sinularia ornata

Mar Drugs. 2022 Mar 20;20(3):218. doi: 10.3390/md20030218.

Abstract

Three complex polyoxygenated diterpenoids possessing uncommon tetradecahydro-2,13:6,9-diepoxybenzo[10]annulene scaffold, namely ximaoornatins A-C (1-3), one new eunicellin-type diterpene, litophynin K (4), and a related known compound, litophynol B (5) were isolated from the South China Sea soft coral Sinularia ornata. The structures and absolute configurations of 1-4 were established by extensive spectroscopic analysis, X-ray diffraction analysis, and/or modified Mosher's method. A plausible biosynthetic relationship of 1 and its potential precursor 4 was proposed. In a bioassay, none of the isolated compounds showed obvious anti-inflammatory activity on LPS-induced TNF-α release in RAW264.7 macrophages and PTP1B inhibitory effects.

Keywords: Sinularia ornata; activity; polyoxygenated diterpenoid; soft coral; stereochemistry.

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Anthozoa / metabolism
  • Biological Products* / chemistry
  • Biological Products* / isolation & purification
  • Biological Products* / metabolism
  • Diterpenes* / chemistry
  • Diterpenes* / isolation & purification
  • Diterpenes* / metabolism
  • Lipopolysaccharides / pharmacology
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / chemistry
  • RAW 264.7 Cells
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Biological Products
  • Diterpenes
  • Lipopolysaccharides
  • Tnf protein, mouse
  • Tumor Necrosis Factor-alpha
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1