PoplarV1, Main, Exploration, bibRecord, 001066

Acylated Quinic Acids Are the Main Salicortin Metabolites in the Lepidopteran Specialist Herbivore Cerura vinula.

Identifieur interne : 001066 ( Main/Exploration ); précédent : 001065; suivant : 001067

Acylated Quinic Acids Are the Main Salicortin Metabolites in the Lepidopteran Specialist Herbivore Cerura vinula.

Auteurs : Felix Feistel [Allemagne] ; Christian Paetz [Allemagne] ; Riya C. Menezes [Allemagne] ; Daniel Veit [Allemagne] ; Bernd Schneider [Allemagne]

Source :

Journal of chemical ecology [ 1573-1561 ] ; 2018.

RBID : pubmed:29549572

Descripteurs français

KwdFr :
- Acide quinique (analyse), Acide quinique (métabolisme), Acylation (MeSH), Animaux (MeSH), Feuilles de plante (composition chimique), Feuilles de plante (physiologie), Glucosides (analyse), Glucosides (métabolisme), Herbivorie (MeSH), Hydrolyse (MeSH), Larve (composition chimique), Larve (physiologie), Lepidoptera (composition chimique), Lepidoptera (physiologie), Oxydoréduction (MeSH), Populus (composition chimique), Populus (physiologie).
MESH :
- analyse : Acide quinique, Glucosides.
- composition chimique : Feuilles de plante, Larve, Lepidoptera, Populus.
- métabolisme : Acide quinique, Glucosides.
- physiologie : Feuilles de plante, Larve, Lepidoptera, Populus.
- Acylation, Animaux, Herbivorie, Hydrolyse, Oxydoréduction.

English descriptors

KwdEn :
- Acylation (MeSH), Animals (MeSH), Glucosides (analysis), Glucosides (metabolism), Herbivory (MeSH), Hydrolysis (MeSH), Larva (chemistry), Larva (physiology), Lepidoptera (chemistry), Lepidoptera (physiology), Oxidation-Reduction (MeSH), Plant Leaves (chemistry), Plant Leaves (physiology), Populus (chemistry), Populus (physiology), Quinic Acid (analysis), Quinic Acid (metabolism).
MESH :
- chemical , analysis : Glucosides, Quinic Acid.
- chemical , metabolism : Glucosides, Quinic Acid.
- chemistry : Larva, Lepidoptera, Plant Leaves, Populus.
- physiology : Larva, Lepidoptera, Plant Leaves, Populus.
- Acylation, Animals, Herbivory, Hydrolysis, Oxidation-Reduction.

Abstract

Salicortin is a phenolic glucoside produced in Salicaceae as a chemical defense against herbivory. The specialist lepidopteran herbivorous larvae of Cerura vinula are able to overcome this defense. We examined the main frass constituents of C. vinula fed on Populus nigra leaves, and identified 11 quinic acid derivatives with benzoate and/or salicylate substitution. We asked whether the compounds are a result of salicortin breakdown and sought answers by carrying out feeding experiments with highly ¹³C-enriched salicortin. Using HRMS and NMR analyses, we were able to confirm that salicortin metabolism in C. vinula proceeds through deglucosylation and ester hydrolysis, after which saligenin is oxidatively transformed into salicylic acid and, eventually, conjugated to quinic acid. To the best of our knowledge, this is the first report of a detoxification pathway based on conjugation with quinic acid.

DOI: 10.1007/s10886-018-0945-1
PubMed: 29549572

Affiliations:

Allemagne

Links toward previous steps (curation, corpus...)

to stream Main, to step Corpus: 000F19
to stream Main, to step Curation: 000F19

Le document en format XML

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<term>Animals (MeSH)</term>
<term>Glucosides (analysis)</term>
<term>Glucosides (metabolism)</term>
<term>Herbivory (MeSH)</term>
<term>Hydrolysis (MeSH)</term>
<term>Larva (chemistry)</term>
<term>Larva (physiology)</term>
<term>Lepidoptera (chemistry)</term>
<term>Lepidoptera (physiology)</term>
<term>Oxidation-Reduction (MeSH)</term>
<term>Plant Leaves (chemistry)</term>
<term>Plant Leaves (physiology)</term>
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<term>Populus (physiology)</term>
<term>Quinic Acid (analysis)</term>
<term>Quinic Acid (metabolism)</term>
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<term>Acide quinique (métabolisme)</term>
<term>Acylation (MeSH)</term>
<term>Animaux (MeSH)</term>
<term>Feuilles de plante (composition chimique)</term>
<term>Feuilles de plante (physiologie)</term>
<term>Glucosides (analyse)</term>
<term>Glucosides (métabolisme)</term>
<term>Herbivorie (MeSH)</term>
<term>Hydrolyse (MeSH)</term>
<term>Larve (composition chimique)</term>
<term>Larve (physiologie)</term>
<term>Lepidoptera (composition chimique)</term>
<term>Lepidoptera (physiologie)</term>
<term>Oxydoréduction (MeSH)</term>
<term>Populus (composition chimique)</term>
<term>Populus (physiologie)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="analysis" xml:lang="en"><term>Glucosides</term>
<term>Quinic Acid</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Glucosides</term>
<term>Quinic Acid</term>
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<term>Glucosides</term>
</keywords>
<keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Larva</term>
<term>Lepidoptera</term>
<term>Plant Leaves</term>
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<keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Feuilles de plante</term>
<term>Larve</term>
<term>Lepidoptera</term>
<term>Populus</term>
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<term>Lepidoptera</term>
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<term>Herbivorie</term>
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<front><div type="abstract" xml:lang="en">Salicortin is a phenolic glucoside produced in Salicaceae as a chemical defense against herbivory. The specialist lepidopteran herbivorous larvae of Cerura vinula are able to overcome this defense. We examined the main frass constituents of C. vinula fed on Populus nigra leaves, and identified 11 quinic acid derivatives with benzoate and/or salicylate substitution. We asked whether the compounds are a result of salicortin breakdown and sought answers by carrying out feeding experiments with highly <sup>13</sup>
C-enriched salicortin. Using HRMS and NMR analyses, we were able to confirm that salicortin metabolism in C. vinula proceeds through deglucosylation and ester hydrolysis, after which saligenin is oxidatively transformed into salicylic acid and, eventually, conjugated to quinic acid. To the best of our knowledge, this is the first report of a detoxification pathway based on conjugation with quinic acid.</div>
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<ArticleTitle>Acylated Quinic Acids Are the Main Salicortin Metabolites in the Lepidopteran Specialist Herbivore Cerura vinula.</ArticleTitle>
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<Abstract><AbstractText>Salicortin is a phenolic glucoside produced in Salicaceae as a chemical defense against herbivory. The specialist lepidopteran herbivorous larvae of Cerura vinula are able to overcome this defense. We examined the main frass constituents of C. vinula fed on Populus nigra leaves, and identified 11 quinic acid derivatives with benzoate and/or salicylate substitution. We asked whether the compounds are a result of salicortin breakdown and sought answers by carrying out feeding experiments with highly <sup>13</sup>
C-enriched salicortin. Using HRMS and NMR analyses, we were able to confirm that salicortin metabolism in C. vinula proceeds through deglucosylation and ester hydrolysis, after which saligenin is oxidatively transformed into salicylic acid and, eventually, conjugated to quinic acid. To the best of our knowledge, this is the first report of a detoxification pathway based on conjugation with quinic acid.</AbstractText>
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<MeshHeading><DescriptorName UI="D011801" MajorTopicYN="N">Quinic Acid</DescriptorName>
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<Keyword MajorTopicYN="N">Salicaceae</Keyword>
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<Keyword MajorTopicYN="N">Stable isotope labeling</Keyword>
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Acylated Quinic Acids Are the Main Salicortin Metabolites in the Lepidopteran Specialist Herbivore Cerura vinula.

Acylated Quinic Acids Are the Main Salicortin Metabolites in the Lepidopteran Specialist Herbivore Cerura vinula.

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