Synthesis of new dicinnamoyl 4-deoxy quinic acid and methyl ester derivatives and evaluation of the toxicity against the pea aphid Acyrthosiphon pisum

被引：5

作者：

Li, Xiubin ^{[1
]}

Grand, Lucie ^{[1
]}

Pouleriguen, Thomas ^{[1
]}

Queneau, Yves ^{[1
]}

da Silva, Pedro ^{[2
]}

Rahbe, Yvan ^{[2
]}

Poessel, Jean-Luc ^{[3
]}

Moebs-Sanchez, Sylvie ^{[1
]}

机构：

[1] Univ Lyon 1, INSA Lyon, CPE Lyon,CNRS, Univ Lyon,ICBMS,Equipe Chim Organ & Bioorgan,UMR, Batiment Jules Verne,20 Ave Albert Einstein, F-69621 Villeurbanne, France

[2] INSA Lyon, INRA BF2I UMR0203, Biol Fonct Insectes & Interact, Batiment Louis Pasteur,20 Ave Albert Einstein, F-69621 Villeurbanne, France

[3] INRA, GAFL, URA 1052, Domaine St Maurice, F-84143 Montfavet, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 08期

关键词：

CHLOROGENIC ACIDS; MYZUS-PERSICAE; DICAFFEOYLQUINIC ACIDS; COFFEE BEANS; LC-MSN; RESISTANCE; EFFICIENT; CAFFEOYL; ROOTS; MONO;

D O I：

10.1039/c5ob02483h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2487 / 2497

页数：11

共 15 条

[1] Design and synthesis of 3, 5-hetero diesters of 4-deoxy quinic acid and their aphicidal activity against Acyrthosiphon pisum
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Sivignon, Catherine
da Silva, Pedro
Rahbe, Yvan
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TETRAHEDRON, 2021, 83
[2] SYNTHESIS AND USE OF A NEW SYNTHON - 4-BROMO-4-DEOXY-L-THREONIC ACID METHYL-ESTER
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AHOND, A
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Zhuang, SX
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JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2003, 50 (06) : 1209 - 1213
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