Zhang Jingjing, Tan Wenqiang, Luan Fang, Yin Xiuli, Dong Fang, Li Qing, Guo Zhanyong
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.
Polymers (Basel). 2018 May 15;10(5):530. doi: 10.3390/polym10050530.
In this paper, quaternary ammonium salts of chitosan bearing halogenated acetate, including ,,-trimethyl chitosan chloroacetate (TMCSC), ,,-trimethyl chitosan dichloroacetate (TMCSDC), ,,-trimethyl chitosan trichloroacetate (TMCSTC), and ,,-trimethyl chitosan trifluoroacetate (TMCSTF), were prepared via ,,-trimethyl chitosan iodide (TMCSI). The obtained chitosan derivatives were characterized by FT-IR, ¹H NMR spectra, C NMR spectra, and elemental analysis. Their antifungal property against f. sp. cucumebrium Owen ( f. sp. cucumebrium Owen), (), and () were evaluated by hyphal measurement method at concentrations ranging from 0.08 mg/mL to 0.8 mg/mL. Meanwhile, two common bacteria, () and (), were selected as the model Gram-negative and Gram-positive bacteria to evaluate the antibacterial property of the chitosan derivatives by agar well diffusion method. The results showed that TMCSC, TMCSDC, TMCSTC, and TMCSTF had better antifungal and antibacterial activities than chitosan and TMCSI. In particular, a rule showed that the inhibitory activity decreased in the order: TMCSTF > TMCSTC > TMCSDC > TMCSC > TMCSI > chitosan, which was consistent with the electron-withdrawing property of different halogenated acetate. Apparently, the quaternary ammonium salts of chitosan with stronger electron withdrawing ability possessed relatively greater antifungal and antibacterial activities. This experiment provides a potentially feasible method for the further utilization of chitosan in fields of antifungal and antibacterial biomaterials.
本文通过碘化三甲基壳聚糖（TMCSI）制备了含卤代乙酸的壳聚糖季铵盐，包括三甲基壳聚糖氯乙酸盐（TMCSC）、三甲基壳聚糖二氯乙酸盐（TMCSDC）、三甲基壳聚糖三氯乙酸盐（TMCSTC）和三甲基壳聚糖三氟乙酸盐（TMCSTF）。通过傅里叶变换红外光谱（FT-IR）、¹H核磁共振谱、¹³C核磁共振谱和元素分析对所得壳聚糖衍生物进行了表征。采用菌丝测量法，在0.08 mg/mL至0.8 mg/mL的浓度范围内评估了它们对黄瓜疫霉（Phytophthora capsici Leonian）、尖孢镰刀菌（Fusarium oxysporum (Schlecht.) f. sp. cucumebrium Owen）和立枯丝核菌（Rhizoctonia solani Kühn）的抗真菌性能。同时，选择两种常见细菌，大肠杆菌（Escherichia coli）和金黄色葡萄球菌（Staphylococcus aureus）作为革兰氏阴性菌和革兰氏阳性菌的模型，通过琼脂孔扩散法评估壳聚糖衍生物的抗菌性能。结果表明，TMCSC、TMCSDC、TMCSTC和TMCSTF比壳聚糖和TMCSI具有更好的抗真菌和抗菌活性。特别是，有规律显示抑制活性顺序为：TMCSTF > TMCSTC > TMCSDC > TMCSC > TMCSI >壳聚糖，这与不同卤代乙酸的吸电子性能一致。显然，吸电子能力较强的壳聚糖季铵盐具有相对较强的抗真菌和抗菌活性。该实验为壳聚糖在抗真菌和抗菌生物材料领域的进一步利用提供了一种潜在可行的方法。
