Acylphloroglucinol Derivatives from Garcinia multiflora with Anti-Inflammatory Effect in LPS-Induced RAW264.7 Macrophages

Molecules. 2018 Oct 10;23(10):2587. doi: 10.3390/molecules23102587.

Abstract

Two new acylphloroglucinol derivatives, 13,14-didehydroxygarcicowin C (1) and 13,14-didehydroxyisoxanthochymol (2), have been isolated from the stems of Garcinia multiflora, together with seven known compounds (39). The structures of new compounds 1 and 2 were elucidated by MS and extensive 1D/2D NMR spectroscopic analyses. Among the isolates, 13,14-didehydroxy-isoxanthochymol (2) and sampsonione B (3) exhibited inhibition against lipopolysaccharide (LPS)-induced NF-κB activation in macrophages at 30 μM with relative luciferase activity values (inhibitory %) of 0.75 ± 0.03 (24 ± 4%) and 0.12 ± 0.03 (88 ± 4%), respectively. Additionally, sampsonione B (3) reduced LPS-induced nitric oxide (NO) production in murine RAW264.7 macrophages and did not induce cytotoxicity against RAW 264.7 cells after 24 h treatment. Compound 3 is worth further investigation and may be expectantly developed as an anti-inflammatory drug candidate.

Keywords: Garcinia multiflora; Guttiferae; anti-inflammatory activity; nitric oxide; nuclear factor κB; structure elucidation.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology*
  • Benzophenones / chemistry
  • Benzophenones / pharmacology
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Garcinia / chemistry*
  • Lipopolysaccharides
  • Mice
  • NF-kappa B / metabolism
  • Nitric Oxide / biosynthesis
  • Phloroglucinol / chemistry
  • Phloroglucinol / pharmacology*
  • Proton Magnetic Resonance Spectroscopy
  • RAW 264.7 Cells

Substances

  • Anti-Inflammatory Agents
  • Benzophenones
  • Lipopolysaccharides
  • NF-kappa B
  • isoxanthochymol
  • Nitric Oxide
  • Phloroglucinol