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Characterization, Diversity, and Structure-Activity Relationship Study of Lipoamino Acids from Pantoea sp. and Synthetic Analogues

A biological evaluation of a library of extracts from entomopathogen strains showed that Pantoea sp. extract has significant antimicrobial and insecticidal activities. Three hydroxyacyl-phenylalanine derivatives were isolated from this strain. Their structures were elucidated by a comprehensive anal...

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Autores principales: Touré, Seindé, Desrat, Sandy, Pellissier, Léonie, Allard, Pierre-Marie, Wolfender, Jean-Luc, Dusfour, Isabelle, Stien, Didier, Eparvier, Véronique
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6429151/
https://www.ncbi.nlm.nih.gov/pubmed/30832353
http://dx.doi.org/10.3390/ijms20051083
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author Touré, Seindé
Desrat, Sandy
Pellissier, Léonie
Allard, Pierre-Marie
Wolfender, Jean-Luc
Dusfour, Isabelle
Stien, Didier
Eparvier, Véronique
author_facet Touré, Seindé
Desrat, Sandy
Pellissier, Léonie
Allard, Pierre-Marie
Wolfender, Jean-Luc
Dusfour, Isabelle
Stien, Didier
Eparvier, Véronique
author_sort Touré, Seindé
collection PubMed
description A biological evaluation of a library of extracts from entomopathogen strains showed that Pantoea sp. extract has significant antimicrobial and insecticidal activities. Three hydroxyacyl-phenylalanine derivatives were isolated from this strain. Their structures were elucidated by a comprehensive analysis of their NMR and MS spectroscopic data. The antimicrobial and insecticidal potencies of these compounds were evaluated, and compound 3 showed 67% mortality against Aedes aegypti larvae at a concentration of 100 ppm, and a minimum inhibitory concentration (MIC) of 16 µg/mL against methicillin-resistant Staphylococcus aureus. Subsequently, hydroxyacyl-phenylalanine analogues were synthesized to better understand the structure-activity relationships within this class of compounds. Bioassays highlighted the antimicrobial potential of analogues containing saturated medium-chain fatty acids (12 or 14 carbons), whereas an unsaturated long-chain fatty acid (16 carbons) imparted larvicidal activity. Finally, using a molecular networking-based approach, several close analogues of the isolated and newly synthesized lipoamino acids were discovered in the Pantoea sp. extract.
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spelling pubmed-64291512019-04-10 Characterization, Diversity, and Structure-Activity Relationship Study of Lipoamino Acids from Pantoea sp. and Synthetic Analogues Touré, Seindé Desrat, Sandy Pellissier, Léonie Allard, Pierre-Marie Wolfender, Jean-Luc Dusfour, Isabelle Stien, Didier Eparvier, Véronique Int J Mol Sci Article A biological evaluation of a library of extracts from entomopathogen strains showed that Pantoea sp. extract has significant antimicrobial and insecticidal activities. Three hydroxyacyl-phenylalanine derivatives were isolated from this strain. Their structures were elucidated by a comprehensive analysis of their NMR and MS spectroscopic data. The antimicrobial and insecticidal potencies of these compounds were evaluated, and compound 3 showed 67% mortality against Aedes aegypti larvae at a concentration of 100 ppm, and a minimum inhibitory concentration (MIC) of 16 µg/mL against methicillin-resistant Staphylococcus aureus. Subsequently, hydroxyacyl-phenylalanine analogues were synthesized to better understand the structure-activity relationships within this class of compounds. Bioassays highlighted the antimicrobial potential of analogues containing saturated medium-chain fatty acids (12 or 14 carbons), whereas an unsaturated long-chain fatty acid (16 carbons) imparted larvicidal activity. Finally, using a molecular networking-based approach, several close analogues of the isolated and newly synthesized lipoamino acids were discovered in the Pantoea sp. extract. MDPI 2019-03-02 /pmc/articles/PMC6429151/ /pubmed/30832353 http://dx.doi.org/10.3390/ijms20051083 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Touré, Seindé
Desrat, Sandy
Pellissier, Léonie
Allard, Pierre-Marie
Wolfender, Jean-Luc
Dusfour, Isabelle
Stien, Didier
Eparvier, Véronique
Characterization, Diversity, and Structure-Activity Relationship Study of Lipoamino Acids from Pantoea sp. and Synthetic Analogues
title Characterization, Diversity, and Structure-Activity Relationship Study of Lipoamino Acids from Pantoea sp. and Synthetic Analogues
title_full Characterization, Diversity, and Structure-Activity Relationship Study of Lipoamino Acids from Pantoea sp. and Synthetic Analogues
title_fullStr Characterization, Diversity, and Structure-Activity Relationship Study of Lipoamino Acids from Pantoea sp. and Synthetic Analogues
title_full_unstemmed Characterization, Diversity, and Structure-Activity Relationship Study of Lipoamino Acids from Pantoea sp. and Synthetic Analogues
title_short Characterization, Diversity, and Structure-Activity Relationship Study of Lipoamino Acids from Pantoea sp. and Synthetic Analogues
title_sort characterization, diversity, and structure-activity relationship study of lipoamino acids from pantoea sp. and synthetic analogues
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6429151/
https://www.ncbi.nlm.nih.gov/pubmed/30832353
http://dx.doi.org/10.3390/ijms20051083
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