A cyanoallyl glucoside from Alliaria petiolata, as a feeding deterrent forlarvae of Pieris napi oleracea

Alliarinoside, a feeding inhibitor against early instar larvae of Pieris na pi oleracea, was isolated from the foliage of Alliaria petiolata and charac terized as (2Z)-4-(beta -D-glucopyranosyloxy)-2-butenenitrile (1) by spectr oscopic methods. The structural assignment was confirmed by synthesis of pe racetylated alliarinoside (2) and its 2E isomer (3). A sample of synthetic 1 was isolated by preparative HPLC from the hydrolysis of the 2Z acetate. F eeding inhibition assays showed comparable activity for the synthetic and n atural glycosides.