Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China.
School of Chemical and Materials Science, Ludong University, Yantai 264025, China.
Carbohydr Polym. 2022 Nov 15;296:119943. doi: 10.1016/j.carbpol.2022.119943. Epub 2022 Aug 1.
In present study, several chitosan derivatives grafted with rosmarinic acid，including chitosan-rosmarinic acid conjugate (CS-RA), chitosan rosmarinic acid salt (CSRA), N,N,N-trimethylated chitosan rosmarinic acid salt (TMCRA), and N-[(2-hydroxy-3-trimethylammonium)propyl]chitosan rosmarinic acid salt (HACRA), were prepared and the effects of different grafting methods on bioactivity of these derivatives were investigated. The structural characterization was identified by FTIR and H NMR spectroscopy. The chitosan derivatives were also evaluated biologically for antioxidant, cytotoxic, and anti-inflammatory activities. Derivatives CSRA, TMCRA, and HACRA prepared through ion exchange method exhibited significant antioxidant ability. All derivatives remarkably inhibited lipopolysaccharide-induced nitric oxide and TNF-α production in RAW 264.7 cells without cytotoxicity, especially derivative TMCRA, whose inhibition rate was >50 % at only 250 μg/mL. The results suggested that chitosan quaternary ammonium derivatives grafted with rosmarinic acid possessed better antioxidant and anti-inflammatory properties than chitosan, which could be used as drug materials against oxidative and inflammation-related pathological processes.
在本研究中，制备了几种接枝迷迭香酸的壳聚糖衍生物，包括壳聚糖-迷迭香酸缀合物（CS-RA）、壳聚糖迷迭香酸盐（CSRA）、N,N,N-三甲基壳聚糖迷迭香酸盐（TMCRA）和 N-[(2-羟基-3-三甲铵基)丙基]壳聚糖迷迭香酸盐（HACRA），并研究了不同接枝方法对这些衍生物生物活性的影响。通过傅里叶变换红外光谱（FTIR）和核磁共振光谱（H NMR）对结构进行了表征。还对壳聚糖衍生物进行了抗氧化、细胞毒性和抗炎活性评价。通过离子交换法制备的 CSRA、TMCRA 和 HACRA 衍生物具有显著的抗氧化能力。所有衍生物均能显著抑制脂多糖诱导的 RAW 264.7 细胞中一氧化氮和 TNF-α的产生，且无细胞毒性，特别是 TMCRA 衍生物，在仅 250μg/mL 时的抑制率>50%。结果表明，接枝迷迭香酸的壳聚糖季铵盐衍生物具有比壳聚糖更好的抗氧化和抗炎特性，可作为治疗与氧化和炎症相关的病理过程的药物。
