Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China; University of Chinese Academy of Sciences, Beijing 100049, China.
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China.
Carbohydr Polym. 2017 Mar 15;160:163-171. doi: 10.1016/j.carbpol.2016.12.060. Epub 2016 Dec 26.
Four novel 1,2,3-triazolium-functionalized starch derivatives were synthesized by N-alkylating the precursor starch derivatives with 1,2,3-triazole with iodomethane based on cuprous-catalyzed azide-alkyne cycloaddition (CuAAC). The detailed structural characterization was investigated by means of FTIR, UV-vis, H NMR, and C NMR spectra. The antifungal activities of starch derivatives against Colletotrichum lagenarium, Fusarium oxysporum, and Watermelon fusarium, were then assayed by hypha measurement in vitro. The fungicidal assessment revealed that compared with starch and starch derivatives with 1,2,3-triazole, 1,2,3-triazolium-functionalized starch derivatives displayed tremendously enhanced antifungal activity. Especially, the inhibitory indices of 6-(4-hydroxymethyl-3-methyl-1,2,3-triazolium-1-yl)-6-deoxy starch iodine (2a) with against the tested plant threatening fungi attained 70% above at 1.0mg/mL. It was also found that their antifungal activity profiles were dependent on the variation in alkyl chain length. As novel 1,2,3-triazolium-functionalized starch derivatives could be prepared efficiently and exhibited superduper antifungal activity, this synthetic strategy might provide an effective way and notion to prepare novel antifungal biomaterials.
四种新型的 1,2,3-三唑鎓功能化淀粉衍生物是通过以碘甲烷为基础的铜催化叠氮-炔环加成（CuAAC），将前体淀粉衍生物与 1,2,3-三唑进行 N-烷基化合成的。通过傅里叶变换红外光谱（FTIR）、紫外可见光谱（UV-vis）、核磁共振氢谱（H NMR）和核磁共振碳谱（C NMR）对其详细结构进行了表征。然后通过体外菌丝测量法测定了淀粉衍生物对胶孢炭疽菌、尖孢镰刀菌和西瓜枯萎病菌的抗真菌活性。杀菌评估表明，与淀粉和含 1,2,3-三唑的淀粉衍生物相比，1,2,3-三唑鎓功能化淀粉衍生物显示出极强的抗真菌活性。特别是，6-（4-羟甲基-3-甲基-1,2,3-三唑-1-基）-6-去氧淀粉碘（2a）对测试的植物致病真菌的抑制指数在 1.0mg/mL 时达到了 70%以上。还发现，它们的抗真菌活性谱取决于烷基链长度的变化。由于新型 1,2,3-三唑鎓功能化淀粉衍生物可以高效制备并表现出超强的抗真菌活性，这种合成策略可能为制备新型抗真菌生物材料提供了一种有效途径和思路。
