College of Sciences, Henan Agricultural University, Zhengzhou, 450002, PR China.
College of Sciences, Henan Agricultural University, Zhengzhou, 450002, PR China.
Carbohydr Res. 2024 Oct;544:109238. doi: 10.1016/j.carres.2024.109238. Epub 2024 Aug 15.
Five novel imidazole-functionalized chitosan derivatives 3a-3e were synthesized via addition reactions of chitosan with imidazole derivatives. The partial incorporation of imidazole moiety in chitosan were confirmed by FTIR, UV, H NMR, XRD, SEM and GPC. Meanwhile, the antifungal activity against three common plant pathogenic fungi: Phytophthora nicotianae (P. nicotianae), Fusarium graminearum (F. graminearum) and Rhizoctonia solani (R. solani), was assayed in vitro at 0.5 and 1.0 mg/mL by hyphal measurement, and the introduction of imidazole group can influence the antifungal activity. At 0.5 mg/mL, 3e inhibited P. nicotianae growth by 42 % and had an inhibitory index against R. solani of 50 %. Derivative 3e was more effective than unmodified chitosan whose antifungal index was 17 % against P. nicotianae and 22 % against R. solani. To our surprise, at 1.0 mg/mL, the inhibition rate of 3e against R. solani can reach 99 %, while the inhibition rate of chitosan is only 38 %. These results indicated that some imidazole chitosan derivatives with enhanced antifungal activities could serve as potential biomaterial for antifungal application.
通过壳聚糖与咪唑衍生物的加成反应，合成了 5 种新型咪唑功能化壳聚糖衍生物 3a-3e。FTIR、UV、1H NMR、XRD、SEM 和 GPC 证实了壳聚糖中咪唑部分的部分掺入。同时，在 0.5 和 1.0 mg/mL 下通过菌丝测量法测定了它们对三种常见植物病原真菌：烟草疫霉（P. nicotianae）、禾谷镰刀菌（F. graminearum）和立枯丝核菌（R. solani）的体外抗真菌活性，引入咪唑基团会影响抗真菌活性。在 0.5 mg/mL 时，3e 抑制了烟草疫霉的生长，抑制率为 42%，对立枯丝核菌的抑制指数为 50%。衍生物 3e 比未修饰的壳聚糖更有效，其对烟草疫霉的抗真菌指数为 17%，对立枯丝核菌的抗真菌指数为 22%。令我们惊讶的是，在 1.0 mg/mL 时，3e 对立枯丝核菌的抑制率可达 99%，而壳聚糖的抑制率仅为 38%。这些结果表明，一些具有增强抗真菌活性的咪唑壳聚糖衍生物可以作为潜在的抗真菌生物材料。
