Literature DB >> 11325224

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

M Haribal1, Z Yang, A B Attygalle, J A Renwick, J Meinwald.   

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-(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.

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Year:  2001        PMID: 11325224     DOI: 10.1021/np000534d

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  17 in total

Review 1.  Variable diets and changing taste in plant-insect relationships.

Authors:  J A Renwick
Journal:  J Chem Ecol       Date:  2001-06       Impact factor: 2.626

2.  Exotic plant invasion in the context of plant defense against herbivores.

Authors: 
Journal:  Plant Physiol       Date:  2012-01-18       Impact factor: 8.340

3.  How Does Garlic Mustard Lure and Kill the West Virginia White Butterfly?

Authors:  Samantha L Davis; Tina Frisch; Nanna Bjarnholt; Don Cipollini
Journal:  J Chem Ecol       Date:  2015-09-23       Impact factor: 2.626

4.  Cyanide in the chemical arsenal of garlic mustard, Alliaria petiolata.

Authors:  Don Cipollini; Bill Gruner
Journal:  J Chem Ecol       Date:  2007-01       Impact factor: 2.626

5.  Dual chemical barriers protect a plant against different larval stages of an insect.

Authors:  J A Renwick; W Zhang; M Haribal; A B Attygalle; K D Lopez
Journal:  J Chem Ecol       Date:  2001-08       Impact factor: 2.626

6.  Seasonal and population variation in flavonoid and alliarinoside content of Alliaria petiolata.

Authors:  M Haribal; J A Renwick
Journal:  J Chem Ecol       Date:  2001-08       Impact factor: 2.626

7.  Arbuscular mycorrhizal fungi protect a native plant from allelopathic effects of an invader.

Authors:  Kathryn Barto; Carl Friese; Don Cipollini
Journal:  J Chem Ecol       Date:  2010-03-13       Impact factor: 2.626

8.  Evolutionary limits ameliorate the negative impact of an invasive plant.

Authors:  Richard A Lankau; Victoria Nuzzo; Greg Spyreas; Adam S Davis
Journal:  Proc Natl Acad Sci U S A       Date:  2009-08-21       Impact factor: 11.205

9.  Density-dependent phytotoxicity of impatiens pallida plants exposed to extracts of Alliaria petiolata.

Authors:  E Kathryn Barto; Don Cipollini
Journal:  J Chem Ecol       Date:  2009-04-21       Impact factor: 2.626

10.  The invasive species Alliaria petiolata (garlic mustard) increases soil nutrient availability in northern hardwood-conifer forests.

Authors:  Vikki L Rodgers; Benjamin E Wolfe; Leland K Werden; Adrien C Finzi
Journal:  Oecologia       Date:  2008-07-09       Impact factor: 3.225

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