Tan Wenqiang, Zhang Jingjing, Luan Fang, Wei Lijie, Chen Yuan, 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.
School of Ocean, Yantai University, Yantai 264005, China.
Int J Biol Macromol. 2017 Sep;102:704-711. doi: 10.1016/j.ijbiomac.2017.04.073. Epub 2017 Apr 23.
Two novel chitosan derivatives modified with quaternary phosphonium salts were successfully synthesized, including tricyclohexylphosphonium acetyl chitosan chloride (TCPACSC) and triphenylphosphonium acetyl chitosan chloride (TPPACSC), and characterized by FTIR, H NMR, and C NMR spectra. The degree of substitution was also calculated by elemental analysis results. Their antifungal activities against Colletotrichum lagenarium, Watermelon fusarium, and Fusarium oxysporum were investigated in vitro using the radial growth assay, minimal inhibitory concentration, and minimum bactericidal concentration assay. The fungicidal assessment revealed that the synthesized chitosan derivatives had superior antifungal activity compared with chitosan. Especially, TPPACSC exhibited the best antifungal property with inhibitory indices of over 75% at 1.0mg/mL. The results obviously showed that quaternary phosphonium groups could effectively enhance antifungal activity of the synthesized chitosan derivatives. Meanwhile, it was also found that their antifungal activity was influenced by electron-withdrawing ability of the quaternary phosphonium salts. The synthetic strategy described here could be utilized for the development of chitosan as antifungal biomaterials.
成功合成了两种用季鏻盐修饰的新型壳聚糖衍生物，包括氯化三环己基鏻乙酰壳聚糖（TCPACSC）和氯化三苯基鏻乙酰壳聚糖（TPPACSC），并通过傅里叶变换红外光谱（FTIR）、氢核磁共振谱（¹H NMR）和碳核磁共振谱（¹³C NMR）对其进行了表征。还通过元素分析结果计算了取代度。使用径向生长测定法、最低抑菌浓度和最低杀菌浓度测定法，在体外研究了它们对葫芦炭疽菌、西瓜枯萎病菌和尖孢镰刀菌的抗真菌活性。杀菌评估表明，与壳聚糖相比，合成的壳聚糖衍生物具有优异的抗真菌活性。特别是，TPPACSC表现出最佳的抗真菌性能，在1.0mg/mL时抑制率超过75%。结果明显表明，季鏻基团可有效增强合成的壳聚糖衍生物的抗真菌活性。同时，还发现它们的抗真菌活性受季鏻盐吸电子能力的影响。本文所述的合成策略可用于开发壳聚糖作为抗真菌生物材料。
