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

Meena Haribal; Zhicai Yang; Athula B. Attygalle; J. Alan A. Renwick; Jerrold Meinwald

doi:10.1021/np000534d

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

Meena Haribal, Zhicai Yang, Athula B. Attygalle, J. Alan A. Renwick, Jerrold Meinwald

Department of Chemistry and Chemical Biology

Cornell University

Research output: Contribution to journal › Article › peer-review

47 Scopus citations

Abstract

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-(β-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.

Original language	English
Pages (from-to)	440-443
Number of pages	4
Journal	Journal of Natural Products
Volume	64
Issue number	4
DOIs	https://doi.org/10.1021/np000534d
State	Published - Apr 2001

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title = "A cyanoallyl glucoside from Alliaria petiolata, as a feeding deterrent for larvae of Pieris napi oleracea",

abstract = "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-(β-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.",

author = "Meena Haribal and Zhicai Yang and Attygalle, \{Athula B.\} and Renwick, \{J. Alan A.\} and Jerrold Meinwald",

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doi = "10.1021/np000534d",

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AU - Haribal, Meena

AU - Yang, Zhicai

AU - Attygalle, Athula B.

AU - Renwick, J. Alan A.

AU - Meinwald, Jerrold

PY - 2001/4

Y1 - 2001/4

N2 - 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-(β-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.

AB - 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-(β-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.

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JF - Journal of Natural Products

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ER -

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

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