Synthesis and Biological Properties of Pyranocoumarin Derivatives as Potent Anti-Inflammatory Agents

Int J Mol Sci. 2023 Jun 12;24(12):10026. doi: 10.3390/ijms241210026.

Abstract

This study aimed to synthesize 23 coumarin derivatives and analyze their anti-inflammatory effects on lipopolysaccharide (LPS)-induced inflammation in RAW264.7 macrophages. A cytotoxicity test performed on LPS-induced RAW264.7 macrophages revealed that none of the 23 coumarin derivatives were cytotoxic. Among the 23 coumarin derivatives, coumarin derivative 2 showed the highest anti-inflammatory activity by significantly reducing nitric oxide production in a concentration-dependent manner. Coumarin derivative 2 inhibited the production of proinflammatory cytokines, including tumor necrosis factor alpha and interleukin-6, and decreased the expression level of each mRNA. In addition, it inhibited the phosphorylation of extracellular signal-regulated kinase, p38, c-Jun NH2-terminal kinase, nuclear factor kappa-B p65 (NF-κB p65), and inducible nitric oxide synthase. These results indicated that coumarin derivative 2 inhibited LPS-induced mitogen-activated protein kinase and NF-κB p65 signal transduction pathways in RAW264.7 cells, as well as proinflammatory cytokines and enzymes related to inflammatory responses, to exert anti-inflammatory effects. Coumarin derivative 2 showed potential for further development as an anti-inflammatory drug for the treatment of acute and chronic inflammatory diseases.

Keywords: Coumarins; RAW264.7 macrophages; lipopolysaccharide.

MeSH terms

  • Anti-Inflammatory Agents / therapeutic use
  • Cytokines / metabolism
  • Extracellular Signal-Regulated MAP Kinases / metabolism
  • Humans
  • Inflammation / metabolism
  • Lipopolysaccharides / pharmacology
  • NF-kappa B* / metabolism
  • Nitric Oxide / metabolism
  • Nitric Oxide Synthase Type II / metabolism
  • Pyranocoumarins* / therapeutic use

Substances

  • NF-kappa B
  • Pyranocoumarins
  • Lipopolysaccharides
  • Anti-Inflammatory Agents
  • Cytokines
  • Extracellular Signal-Regulated MAP Kinases
  • Nitric Oxide
  • Nitric Oxide Synthase Type II

Grants and funding

This work was funded by the National Research Foundation of Korea (NRF, 2021R1F1A1063787 and 2019K1A3A1A82113697) grants supported by the Korean government (MSIP) and KIST intramural grant.