title: Synthesis of new dicinnamoyl 4-deoxy quinic acid and methyl ester derivatives and evaluation of the toxicity against the pea aphid Acyrthosiphon pisum.
abstract: New dicinnamoyl (caffeoyl, feruloyl, ortho and para-coumaroyl) 4-deoxyquinic acid and esters were synthesized by using a new 4-deoxy quinic acid triol intermediate. The optimisation of both coupling and deprotection steps allowed the preparation in good yields of the target products either as the carboxylic acid or the methyl ester form. Eight new compounds were evaluated for their ability to influence the feeding behaviour of the pea aphid Acyrthosiphon pisum. Artificial diet bioassays showed that two compounds are toxic (mortality and growth inhibition) at lower concentrations than the reference 3,5-dicaffeoyl quinic acid.
authors.affiliation: Université de Lyon, INSA Lyon, ICBMS, Equipe Chimie organique et Bioorganique, UMR 5246 CNRS, Université Lyon1, INSA Lyon, CPE Lyon, Bâtiment Jules Verne, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France. sylvie.moebs@insa-lyon.fr.
authors.forename: Xiubin
authors.initials: X
authors.lastname: Li
authors.affiliation: Université de Lyon, INSA Lyon, ICBMS, Equipe Chimie organique et Bioorganique, UMR 5246 CNRS, Université Lyon1, INSA Lyon, CPE Lyon, Bâtiment Jules Verne, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France. sylvie.moebs@insa-lyon.fr.
authors.forename: Lucie
authors.initials: L
authors.lastname: Grand
authors.affiliation: Université de Lyon, INSA Lyon, ICBMS, Equipe Chimie organique et Bioorganique, UMR 5246 CNRS, Université Lyon1, INSA Lyon, CPE Lyon, Bâtiment Jules Verne, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France. sylvie.moebs@insa-lyon.fr.
authors.forename: Thomas
authors.initials: T
authors.lastname: Pouleriguen
authors.affiliation: Université de Lyon, INSA Lyon, ICBMS, Equipe Chimie organique et Bioorganique, UMR 5246 CNRS, Université Lyon1, INSA Lyon, CPE Lyon, Bâtiment Jules Verne, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France. sylvie.moebs@insa-lyon.fr.
authors.forename: Yves
authors.initials: Y
authors.lastname: Queneau
authors.affiliation: INSA Lyon, INRA BF2I UMR0203, Biologie Fonctionnelle Insectes et Interaction, Bâtiment Louis Pasteur, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France. pedro.da-silva@insa-lyon.fr.
authors.forename: Pedro
authors.initials: P
authors.lastname: da Silva
authors.affiliation: INSA Lyon, INRA BF2I UMR0203, Biologie Fonctionnelle Insectes et Interaction, Bâtiment Louis Pasteur, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France. pedro.da-silva@insa-lyon.fr.
authors.forename: Yvan
authors.initials: Y
authors.lastname: Rahbé
authors.affiliation: INRA Avignon, GAFL, URA 1052, Domaine St Maurice, 84143 Montfavet Cedex, France. jean-luc.poessel@avignon.inra.fr.
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Poëssel
authors.affiliation: Université de Lyon, INSA Lyon, ICBMS, Equipe Chimie organique et Bioorganique, UMR 5246 CNRS, Université Lyon1, INSA Lyon, CPE Lyon, Bâtiment Jules Verne, 20 Avenue Albert Einstein, F-69621 Villeurbanne Cedex, France. sylvie.moebs@insa-lyon.fr.
authors.forename: Sylvie
authors.initials: S
authors.lastname: Moebs-Sanchez
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects* / Q000254:growth & development; D002934:Cinnamates / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D004305:Dose-Response Relationship, Drug; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D005247:Feeding Behavior / Q000187:drug effects; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D015394:Molecular Structure; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*
chemical_list: D002934:Cinnamates; D004952:Esters; D007306:Insecticides; D011801:Quinic Acid