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Synthesis of N-Alkyl-beta-D-glucosylamines and Their Antimicrobial Activity against Fusarium proliferatum, Salmonella typhimurium, and Listeria innocua

dc.rights.licenseopen
hal.structure.identifierUnité des Sciences du bois et des biopolymères [Us2b]
dc.contributor.authorMUHIZI, Theoneste
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 2 LCPO : Biopolymers & Bio-sourced Polymers
dc.contributor.authorGRELIER, Stéphane
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 2 LCPO : Biopolymers & Bio-sourced Polymers
dc.contributor.authorCOMA, Veronique
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2009
dc.identifier.issn0021-8561
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20383
dc.description.abstractEnIn this study, different N-alkyl-beta-D-glucosylamines were evaluated for both antifungal and antibacterial activity against Fusarium proliferatum (INRA, MUCL 1807.7), Listeria innocua (ISTAB, Universite Bordeaux 1), and Salmonella typhimurium (Institut Pasteur 5858). The tested glucosylamines were beta-D-glucosylamine (GPA), N-ethyl-beta-D-glucosylamine (EtGPA), N-butyl-beta-D-glucosylamine (BuGPA), N-hexyl-beta-D-glucosylamine (HeGPA), N-octyl-beta-D-glucosylamine (OcGPA), N-dodecyl-beta-D-glucosylamine (DoGPA), N-(2-hydroxyethyl)-beta-D-glucosylamine (HEtGPA), N,N-di(2-hydroxyethyl)-beta-D-glucosylamine (DHEtGPA) and N,N-diethyl-beta-D-glucosylamine (DEtGPA). The effectiveness of N-alkyl length, N-substitution, and N-hydroxyalkyl groups on both antibacterial and antifungal activity were evaluated. Results indicated that these compounds exhibited different biological activities and their effectiveness was highly increased from short to long N-alkyl chains. DoGPA exhibited more potent biological activity against all target strains than other N-alkyl glucosylamines tested. Using a radial growth method, we demonstrated that this compound completely inhibited fungal growth at 0.5 x 10(-4) mol mL(-1), while OcGPA and HeGPA lead to 71% and 43% fungal inhibition, respectively. Using the coating method, we demonstrated that DoGPA completely inhibited bacterial growth at 0.025 x 10(-4) and 0.05 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively, while at the same concentrations, OcGPA exhibited weaker antibacterial activity of 12% and 27%, respectively, for L. innocua and S. typhimurium. The hole plate method enabled us to estimate the minimum inhibitory concentration (MIC) of DoGPA found to be 0.02 x 10(-4) and 0.025 x 10(-4) mol mL(-1) for L. innocua and S. typhimurium, respectively. Glucosylamines with N-hydroxyalkyl and short N-alkyl chains varying from C-2 to C-4 exhibited weaker antimicrobial activity.
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.subject.enSalmonella typhimurium
dc.subject.enListeria Innocua
dc.subject.enAntifungal activity
dc.subject.enantibacterial activity
dc.subject.englucosylamines
dc.subject.enFusarium proliferatum
dc.title.enSynthesis of N-Alkyl-beta-D-glucosylamines and Their Antimicrobial Activity against Fusarium proliferatum, Salmonella typhimurium, and Listeria innocua
dc.typeArticle de revue
dc.identifier.doi10.1021/jf9016114
dc.subject.halChimie/Polymères
bordeaux.journalJournal of Agricultural and Food Chemistry
bordeaux.page11092-11099
bordeaux.volume57
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue23
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-00944898
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-00944898v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Journal%20of%20Agricultural%20and%20Food%20Chemistry&rft.date=2009&rft.volume=57&rft.issue=23&rft.spage=11092-11099&rft.epage=11092-11099&rft.eissn=0021-8561&rft.issn=0021-8561&rft.au=MUHIZI,%20Theoneste&GRELIER,%20St%C3%A9phane&COMA,%20Veronique&rft.genre=article


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