UMR 5103 US2B, Unité des Sciences du Bois et des Biopolymères, Université Bordeaux 1, INRA, CNRS, Talence, France.
J Agric Food Chem. 2009 Dec 9;57(23):11092-9. doi: 10.1021/jf9016114.
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.
在这项研究中，评估了不同的 N-烷基-β-D-葡糖胺对扩展青霉（INRA，MUCL 1807.7）、无害李斯特菌（ISTAB，波尔多第一大学）和鼠伤寒沙门氏菌（巴斯德研究所 5858）的抗真菌和抗菌活性。测试的葡糖胺有β-D-葡糖胺（GPA）、N-乙基-β-D-葡糖胺（EtGPA）、N-丁基-β-D-葡糖胺（BuGPA）、N-己基-β-D-葡糖胺（HeGPA）、N-辛基-β-D-葡糖胺（OcGPA）、N-十二烷基-β-D-葡糖胺（DoGPA）、N-（2-羟乙基）-β-D-葡糖胺（HEtGPA）、N,N-二（2-羟乙基）-β-D-葡糖胺（DHEtGPA）和 N,N-二乙基-β-D-葡糖胺（DEtGPA）。评估了 N-烷基长度、N-取代基和 N-羟烷基对抗菌和抗真菌活性的影响。结果表明，这些化合物表现出不同的生物活性，其有效性从短到长的 N-烷基链显著增加。与测试的其他 N-烷基葡糖胺相比，DoGPA 对所有目标菌株表现出更强的生物活性。使用放射状生长法，我们证明该化合物在 0.5 x 10(-4) mol mL(-1) 时完全抑制真菌生长，而 OcGPA 和 HeGPA 分别导致 71%和 43%的真菌抑制。使用涂层法，我们证明 DoGPA 在 0.025 x 10(-4) 和 0.05 x 10(-4) mol mL(-1) 时完全抑制了无害李斯特菌和鼠伤寒沙门氏菌的细菌生长，而在相同浓度下，OcGPA 对无害李斯特菌和鼠伤寒沙门氏菌的抗菌活性分别较弱，为 12%和 27%。微孔板法使我们能够估计出 DoGPA 的最小抑菌浓度（MIC），对无害李斯特菌和鼠伤寒沙门氏菌的 MIC 分别为 0.02 x 10(-4) 和 0.025 x 10(-4) mol mL(-1)。具有 N-羟烷基和 C-2 至 C-4 之间变化的短 N-烷基链的葡糖胺表现出较弱的抗菌活性。
