Synthesis, characterization and antifungal activity of imidazole chitosan derivatives

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY Carbohydrate Research Pub Date : 2024-08-15 DOI:10.1016/j.carres.2024.109238

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Abstract

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, ¹H 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.

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咪唑壳聚糖衍生物的合成、表征和抗真菌活性

通过壳聚糖与咪唑衍生物的加成反应，合成了五种新型咪唑官能化壳聚糖衍生物 3a-3e。傅立叶变换红外光谱（FTIR）、紫外光谱（UV）、1H NMR、XRD、扫描电镜（SEM）和气相色谱（GPC）证实了壳聚糖中部分咪唑分子的结合。同时，该化合物对三种常见植物病原真菌具有抗真菌活性：在 0.5 和 1.0 mg/mL 的浓度下，通过菌丝测定法对三种常见植物病原真菌：烟曲霉（Phytophthora nicotianae）、禾谷镰刀菌（Fusarium graminearum）和茄根霉（Rhizoctonia solani）进行了体外试验，结果表明咪唑基团的引入会影响抗真菌活性。在 0.5 毫克/毫升的浓度下，3e 可抑制 42% 的尼古丁虫生长，对索拉尼菌的抑制指数为 50%。衍生物 3e 比未经改性的壳聚糖更有效，后者对烟碱蚁的抗真菌指数为 17%，对索拉尼菌的抗真菌指数为 22%。令我们惊讶的是，在 1.0 毫克/毫升的浓度下，3e 对 R. solani 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作为潜在的生物材料用于抗真菌应用。

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".