Synthesis ofN-Alkyl-β-d-glucosylamines and Their Antimicrobial Activity againstFusarium proliferatum,Salmonellatyphimurium, andListeria innocua

Abstract

In 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, Université 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.

Influence of the Variation of the Alkyl Chain Length of N-Alkyl-β-d-glycosylamine Derivatives on Antifungal Properties

“…Results are detailed in Figure for N -alkylglucosylamines and in Figure for galactose-based derivatives. The antifungal activity of the glucosylamines increased with the alkyl chain length, from 6 to 16 carbons, which is in accordance with the literature. , At the tested concentrations ((1.5–2.5) × 10 –5 mol·mL –1 ), there was no significant difference between the antifungal activities of hexyl- and octylglucosylamines and the DMSO control. For the hexadecyl compound 5 , at each concentration, a complete inhibition of the mycelium growth of A.…”

“…Recent studies have shown that amino-containing carbohydrate compounds exhibit antifungal activities and have indicated promising results. , In addition, aminopolysaccharides such as chitosan and its glucosamine constitutive monomer are well-known to present antifungal and antibacterial activities. − Carbohydrates and their derivatives are important synthesis targets because of their wide range of functions in living organisms . Derivatives bearing an amino substituent in different ring positions on the sugar skeleton are called aminosugars and are known constituents of several bioactive compounds such as antibiotics , and biopolymers .…”

Inhibitory Activities of Griseofulvin and Its Analogues against Phytopathogenic Fungi

“…Mycelial growth assay: The antifungal activity of compounds was evaluated by the mycelial growth assay [20][21][22] , conducted on PDA medium. Prior to the fungal inoculation, 100 µL of different concentrations of the tested compounds were poured and spread on the surface of the agar medium.…”

Polysaccharide-based Biomaterials with Antimicrobial and Antioxidant Properties

“…A very interesting review summarizes the chitosan MIC values according to recent data found in the literature [68] , indicating that the effectiveness of this aminopolysaccharide is dependent on microbial species. Our group has been published several papers dealing with the bioactive properties of chitosan-based matrices [69][70][71][72] and with the bioactivity of glucosamine derivatives [73][74][75] .…”

“…These antioxidant properties of chitosan-based Figure 10. Shiff's base obtained from the reaction between free amino groups of chitosan and aldehydes and the synthesis of N,N,N-trimethylchitosan according to Belalia et al [74] films resulted from the progressive release of THCs, due to interactions between chitosan and the antioxidative agent.…”