Insecticidal amides from fruits of Piper nigrum Linn

Nat Prod Res. 2005 Feb;19(2):143-50. doi: 10.1080/14786410410001704750.

Abstract

The petroleum ether and ethyl acetate fractions of dried ground seeds of Piper nigrum Linn. afforded sixteen compounds (1-16) including one new insecticidal amide, pipwaqarine (1) and six constituents (3,4,6,7,11,15) previously unreported from this plant. The structure of (1) has been elucidated through extensive 1D-, 2D-NMR spectral studies as, 1-[13-(3',4'-methylenedioxyphenyl)-2E,4E,12E-tridecatrienoyl]-N-isopentylamide, while those of known constituents through comparison of spectral data. 1 exhibited toxicity of 30ppm against fourth instar larvae of Aedes aegypti Liston determined by WHO method. A portion of petroleum ether fraction was also subjected to GC and GC-MS analysis resulting in the identification of three compounds (17-19) using the NIST Mass spectral search program 1998 and Kovat's retention indices. Two of these compounds, 17 and 18, are reported for the first time from this plant.

MeSH terms

  • Aedes
  • Alkenes / chemistry
  • Alkenes / isolation & purification*
  • Alkenes / pharmacology
  • Amides / chemistry
  • Amides / isolation & purification*
  • Amides / pharmacology
  • Animals
  • Fruit / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Insecticides / chemistry
  • Insecticides / isolation & purification*
  • Insecticides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Piper nigrum / chemistry*

Substances

  • 1-(13-(3',4'-methylenedioxyphenyl)-2E,4E,12E-tridecatrienoyl)-N-isopentylamide
  • Alkenes
  • Amides
  • Insecticides