A cyanoallyl glucoside from Alliaria petiolata, as a feeding deterrent for larvae of Pieris napi oleracea.
Alliarinoside, a feeding inhibitor against early instar larvae of Pieris napi oleracea, was isolated from the foliage of Alliaria petiolata and characterized as (2Z)-4-(beta-D-glucopyranosyloxy)-2-butenenitrile (1) by spectroscopic methods. The structural assignment was confirmed by synthesis of peracetylated alliarinoside (2) and its 2E isomer (3). A sample of synthetic 1 was isolated by preparative HPLC from the hydrolysis of the 2Z acetate. Feeding inhibition assays showed comparable activity for the synthetic and natural glycosides.
Haribal
M
M
Boyce Thompson Institute, Tower Road, Ithaca, New York 14853, USA. mmh3@cornell.edu
Yang
Z
Z
Attygalle
A B
AB
Renwick
J A
JA
Meinwald
J
J
D000818:Animals; D019607:Brassicaceae / Q000737:chemistry*; D005247:Feeding Behavior / Q000187:drug effects*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007313:Insecta / Q000254:growth & development; D007814:Larva / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization
D005960:Glucosides; D009570:Nitriles; C430148:alliarinoside