A Cyanoallyl Glucoside from Alliaria petiolata, as a Feeding Deterrent for Larvae of Pieris napi oleracea

• Published in: Journal of natural products (Washington, D.C.) Vol. 64; no. 4; pp. 440 - 443
• Main Authors: HARIBAL, Meena, YANG, Zhicai, ATTYGALLE, Athula B., RENWICK, J. Alan A., MEINWALD, Jerrold
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.2001; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Alliaria petiolata; Analytical, structural and metabolic biochemistry; Animals; Biological and medical sciences; Brassicaceae - chemistry; Carbohydrates; Chemical control; Chemistry, Medicinal; Control; Feeding Behavior - drug effects; Fundamental and applied biological sciences. Psychology; Glucosides - chemistry; Glucosides - isolation & purification; Glucosides - pharmacology; glycosides; Insecta - growth & development; Larva - drug effects; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Molecular Structure; Nitriles - chemistry; Nitriles - isolation & purification; Nitriles - pharmacology; Oses; Other biological molecules; Pharmacology & Pharmacy; Phytopathology. Animal pests. Plant and forest protection; Pieridae; Pieris napi; Plant Sciences; Protozoa. Invertebrates; Science & Technology; Spectrometry, Mass, Electrospray Ionization; United States; North America; America; POTASSIUM LESPEDEZATE; CYANOGLUCOSIDE; SUBSTANCES; Insecticide; Nitrile; Insecta; Pesticide crop; Cruciferae; Dicotyledones; Angiospermae; Vinylic compound; Antifeedant; Pieridae; Glycoside; Pieris napi; Aldose; Aliphatic compound; Pesticides; Glucoside; Plant leaf; Biological activity; Larva; Arthropoda; Lepidoptera; Plant origin; Isolation; Spermatophyta; Invertebrata; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np000534d

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.