Resveratrol-based cinnamic ester hybrids: synthesis, characterization, and anti-inflammatory activity

J Enzyme Inhib Med Chem. 2017 Dec;32(1):1282-1290. doi: 10.1080/14756366.2017.1381090.

Abstract

Twenty-three novel resveratrol-based cinnamic ester hybrids were designed and synthesized. All the compounds were evaluated for their anti-inflammatory activity using RAW264.7 cells. Among them, compound D15 was found to be the most potent one in inhibiting NO production in LPS-stimulated RAW264.7 cells. The further study indicated that compound D15 could suppress expression of proteins iNOS, COX-2, p-p65, and p-IκB LPS-induced. Immunofluorescence further revealed compound D15 could reduce activation p65 in nuclei. All the results indicated that the anti-inflammatory activity of title compound may partly due to its inhibitory effect on the NF-κB signaling pathway.

Keywords: NF-κB signaling pathway; Resveratrol derivatives; anti-inflammatory; cinnamic ester; molecular docking.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Blotting, Western
  • Cells, Cultured
  • Cinnamates / chemical synthesis*
  • Cinnamates / chemistry
  • Cinnamates / pharmacology*
  • Crystallography, X-Ray
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Esters / pharmacology*
  • Macrophages / drug effects*
  • Macrophages / immunology
  • Mice
  • Molecular Docking Simulation
  • Molecular Structure
  • NF-kappa B p50 Subunit / antagonists & inhibitors
  • RAW 264.7 Cells
  • Resveratrol
  • Signal Transduction / drug effects
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry
  • Stilbenes / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Cinnamates
  • Esters
  • NF-kappa B p50 Subunit
  • Stilbenes
  • cinnamic acid
  • Nfkb1 protein, mouse
  • Resveratrol

Grants and funding

We gratefully acknowledge financial support from the National Natural Science Foundation of China (21602042, 21572003), Anhui Provincial Natural Science Foundation (1508085MB33), the Fundamental Research Funds for the Central Universities, and the Key Scientific and Technological Project of Anhui Provincial Tobacco Company (No. 20150551007).