Synthesis of novel derivatives of murrayafoline A and their inhibitory effect on LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells

Arch Pharm Res. 2013 Jul;36(7):832-9. doi: 10.1007/s12272-013-0100-z. Epub 2013 Apr 6.

Abstract

A series of N-substituted-1,2,3-triazole murrayafoline A derivatives were successfully synthesized using click azide-alkyne Huisgen cycloaddition reaction between 1-methoxy-3-methyl-9-(3-azido)-propyl-9H-carbazole and substituted alkynes. Their chemical structures were confirmed by (1)H, (13)C NMR and HR-ESI-MS spectral data. In addition, the interested effects on LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells of synthetic murrayafoline A derivatives were also investigated. Our results indicated that murrayafoline A derivatives containing 1,2,3-triazole nucleus potentially possessed anti-inflammatory action through inhibiting production of IL-6, IL-12 p40 and TNF-α.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / pharmacology
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Bone Marrow Cells / drug effects*
  • Bone Marrow Cells / metabolism
  • Carbazoles / chemical synthesis*
  • Carbazoles / pharmacology
  • Cells, Cultured
  • Cytokines / antagonists & inhibitors*
  • Cytokines / biosynthesis
  • Dendritic Cells / drug effects*
  • Dendritic Cells / metabolism
  • Dose-Response Relationship, Drug
  • Inflammation Mediators / antagonists & inhibitors*
  • Inflammation Mediators / physiology
  • Lipopolysaccharides / toxicity
  • Mice
  • Mice, Inbred C57BL
  • Plant Roots
  • Rutaceae

Substances

  • Alkaloids
  • Anti-Inflammatory Agents, Non-Steroidal
  • Carbazoles
  • Cytokines
  • Inflammation Mediators
  • Lipopolysaccharides
  • murrayafoline A