Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells

Bioorg Med Chem Lett. 2011 Dec 1;21(23):6960-3. doi: 10.1016/j.bmcl.2011.09.128. Epub 2011 Oct 7.

Abstract

A new alkaloid, methyl 2'-(7,8-dihydrosanguinarine-8-yl)acetate (1), together with six known alkaloids, stylopine (2), protopine (3), norchelidonine (4), chelidonine (5), berberine (6), and 8-hydroxydihydrosanguinarine (7), were isolated from Chelidonium majus. Their chemical structures were primarily established using 1D and 2D NMR techniques and mass spectrometry. The anti-inflammatory activity of the isolates was examined for their inhibitory effects on LPS-induced NO production in macrophage RAW264.7 cells. Among them, compounds 5 and 7 showed strong inhibitory activities toward the LPS-induced NO production in macrophage RAW264.7 cells with IC(50) values of 7.3 and 4.5 μM, respectively. In addition, compounds 5 and 7 inhibited the inductions of COX-2 and iNOS mRNA in dose-dependent manners, indicating that these compounds attenuated the syntheses of these transcripts at the transcriptional level.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / pharmacology*
  • Animals
  • Benzophenanthridines / chemical synthesis*
  • Benzophenanthridines / chemistry
  • Benzophenanthridines / pharmacology
  • Cell Line
  • Chelidonium / chemistry*
  • Cyclooxygenase 2 / metabolism
  • Inhibitory Concentration 50
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Isoquinolines / pharmacology
  • Lipopolysaccharides* / pharmacology
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / metabolism*
  • Plant Extracts / pharmacology

Substances

  • Alkaloids
  • Benzophenanthridines
  • Isoquinolines
  • Lipopolysaccharides
  • Plant Extracts
  • methyl 2'-(7,8-dihydrosanguinarine-8-yl)acetate
  • Nitric Oxide
  • Cyclooxygenase 2