New benzamide derivatives and NO production inhibitory compounds from Limonia acidissima

Planta Med. 2009 Aug;75(10):1146-51. doi: 10.1055/s-0029-1185512. Epub 2009 Apr 2.

Abstract

Three new benzamide derivatives, N-{[ P-(3,7-dimethyl-6 R,7-dihydroxy-4 R-octadecanoyloxy-2-octenyloxy)phenyl]ethyl} benzamide (1), N-{[ P-(3,7-dimethyl-6 R,7-dihydroxy-4 R-9'''( E)-octadecenoyloxy-2-octenyloxy)phenyl]ethyl} benzamide (2), and N-{[ P-(3,7-dimethyl-6 R,7-epoxy-4 R-9'''( E)-octadecenoyloxy-2-octenyloxy)phenyl]ethyl} benzamide (3), together with 10 known compounds (4-13), were isolated from the bark of Limonia acidissima. The structures of these new compounds were determined through spectral analyses, including extensive 2D NMR data. Among the isolates, 13 alpha,14 beta,17 alpha-lanosta-7,9,24-triene-3 beta,16 alpha-diol (8), 4-methoxy-1-methyl-2(1 H)-quinolinone (10), and 13 alpha,14 beta,17 alpha-lanosta-7,24-diene-3 beta,11 beta,16 alpha-triol (13) potently inhibited nitric oxide (NO) production in microglia cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzamides / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Microglia / drug effects
  • Microglia / metabolism
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Plant Extracts / pharmacology*
  • Rutaceae / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Ultraviolet

Substances

  • Benzamides
  • Plant Extracts
  • Nitric Oxide