Carapanosins A-C from Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production

Molecules. 2017 Mar 22;22(3):502. doi: 10.3390/molecules22030502.

Abstract

Two new phragmalin-type limonoids, Carapanosins A and B (1 and 2), and a new gedunin-type limonoid, Carapansin C (3), together with five known limonoids (4-8) were isolated from the oil of Carapa guianensis AUBLET (Meliaceae) seeds, a traditional medicine in Brazil and Latin American countries. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and HRFABMS. Compounds 1-8 were evaluated for their effects on the production of NO in LPS-activated mouse peritoneal macrophages. The NO inhibitory assay suggested that Compounds 3, 6, and 8 may be valuable as potential inhibitors of macrophage activation.

Keywords: Carapa guianensis; Carapanosins A–C; Meliaceae; limonoid; seed oil.

MeSH terms

  • Animals
  • Cell Line
  • Limonins / chemistry*
  • Limonins / pharmacology*
  • Lipopolysaccharides / immunology
  • Macrophage Activation / drug effects
  • Macrophage Activation / immunology
  • Macrophages / drug effects*
  • Macrophages / immunology
  • Macrophages / metabolism*
  • Magnetic Resonance Spectroscopy
  • Meliaceae / chemistry*
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nitric Oxide / metabolism*
  • Plant Oils / chemistry
  • Plant Oils / pharmacology
  • Seeds / chemistry*

Substances

  • Limonins
  • Lipopolysaccharides
  • Plant Oils
  • Nitric Oxide