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 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...

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Bibliographic Details
Published in:International journal of molecular sciences 2019-03, Vol.20 (5), p.1083
Main Authors: Touré, Seindé, Desrat, Sandy, Pellissier, Léonie, Allard, Pierre-Marie, Wolfender, Jean-Luc, Dusfour, Isabelle, Stien, Didier, Eparvier, Véronique
Format: Article
Language:English
Subjects:
Abuse
Amino acids
Antibiotics
Antimicrobial agents
Chemical Sciences
Chemicals
Esters
Fatty acids
Lithium
Lithium hydroxides
Medicinal Chemistry
Metabolites
Microorganisms
Mosquitoes
Pathogens
Pesticides
Phenylalanine
Public health
Staphylococcus infections
Structural analysis
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Summary:A biological evaluation of a library of extracts from entomopathogen strains showed that 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 showed 67% mortality against larvae at a concentration of 100 ppm, and a minimum inhibitory concentration (MIC) of 16 µg/mL against methicillin-resistant . 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 sp. extract.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms20051083