School of Food Science and Biotechnology, Zhejiang Gongshang University, Xiasha, Hangzhou, Zhejiang 310018, PR China.
Department of Food Science, Faculty of Hospitality Management, Shanghai Business School, Shanghai 200235, PR China.
Carbohydr Polym. 2022 Sep 1;291:119608. doi: 10.1016/j.carbpol.2022.119608. Epub 2022 May 12.
A novel thioether chitosan oligosaccharide (COS-All-Tio) was prepared by the reaction of chitosan oligosaccharide (COS) with 3-bromopropene, followed by the coupling with tiopronin (Tio) using a thiol-ene reaction. The degree of substitution of COS-All-Tio reached 1.48. The structure of COS-All-Tio was identified by IR, NMR spectra. It was found that COS-All-Tio possessed more potent antioxidant activities than COS. The IC values of COS-All-Tio for scavenging DPPH, ABTS and OH were 0.31, 0.39 and 0.73 mg/mL, respectively, while the corresponding values for COS were 0.66, 2.89 and 1.41 mg/mL, respectively. COS-All-Tio was also found to possess much stronger antibacterial effect than COS against five bacteria strains (Staphylococcus aureus, Bacillus subtilis, Listeria monocytogenes, Escherichia coli and Pseudomonas aeruginosa). Further, COS-All-Tio was found to be non-toxic to RAW264.7 macrophages and MRC-5 human lung cells. This work provides a convenient way to improve the antioxidant and antibacterial activities of COS.
一种新型硫醚壳聚糖寡糖（COS-All-Tio）通过壳聚糖寡糖（COS）与 3-溴丙烯反应，然后通过硫醇-烯反应与硫普罗宁（Tio）偶联制备。COS-All-Tio 的取代度达到 1.48。COS-All-Tio 的结构通过红外光谱（IR）、核磁共振光谱（NMR）确定。结果表明，COS-All-Tio 比 COS 具有更强的抗氧化活性。COS-All-Tio 清除 DPPH、ABTS 和 OH 的 IC 值分别为 0.31、0.39 和 0.73mg/mL，而 COS 的相应值分别为 0.66、2.89 和 1.41mg/mL。与 COS 相比，COS-All-Tio 对五种细菌（金黄色葡萄球菌、枯草芽孢杆菌、单核细胞增生李斯特菌、大肠杆菌和铜绿假单胞菌）也具有更强的抗菌作用。此外，COS-All-Tio 对 RAW264.7 巨噬细胞和 MRC-5 人肺细胞无毒性。这项工作为提高 COS 的抗氧化和抗菌活性提供了一种简便的方法。
