New 8-Hydroxybriaranes from the Gorgonian Coral Junceella fragilis (Ellisellidae)

Mar Drugs. 2019 Sep 14;17(9):534. doi: 10.3390/md17090534.

Abstract

Three new 8-hydroxybriaranes-fragilides R-T (1-3) were obtained from a sea whip gorgonian coral Junceella fragilis. The structures of briaranes 1-3 were elucidated by using spectroscopic methods, including 1D (1H and 13C NMR), 2D (COSY, HSQC, HMBC, and NOESY experiments) NMR studies, and (+)-HRESIMS. Fragilides S and T (2 and 3) are the only briaranes known to possess 8α-hydroxy and 17β-methyl groups, respectively. Briarane 2 exerted an inhibition effect on iNOS release from RAW264.7; a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides.

Keywords: Junceella fragilis; anti-inflammatory; briarane; fragilide; iNOS.

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Mice
  • Molecular Structure
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Nitric Oxide Synthase Type II / metabolism
  • Proton Magnetic Resonance Spectroscopy
  • RAW 264.7 Cells
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Diterpenes
  • Nitric Oxide Synthase Type II
  • Nos2 protein, mouse