Insecticidal amides from fruits of Piper nigrum Linn.
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.
Siddiqui
Bina S
BS
HEJ Research Institute of Chemistry, International Centre for Chemical Sciences, University of Karachi, Karachi - 75270, Pakistan. bina@khi.comsats.net.pk
Gulzar
Tahsin
T
Begum
Sabira
S
Afshan
Farhana
F
Sattar
Fouzia A
FA
D000330:Aedes; D000475:Alkenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000577:Amides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D005638:Fruit / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D029222:Piper nigrum / Q000737:chemistry*
C497373:1-(13-(3',4'-methylenedioxyphenyl)-2E,4E,12E-tridecatrienoyl)-N-isopentylamide; D000475:Alkenes; D000577:Amides; D007306:Insecticides