Department of Packaging and Materials Technology, Faculty of Agro-Industry, Kasetsart University, Bangkok 10900, Thailand.
Carbohydr Polym. 2013 Jul 25;96(2):495-502. doi: 10.1016/j.carbpol.2013.04.006. Epub 2013 Apr 12.
The objective of the present work was to improve the antioxidant activity and water solubility of chitosan by grafting with ferulic acid through a carbodiimide-mediated coupling reaction. UV-vis spectrophotometry, FTIR, (1)H NMR and ninhydrin assay confirmed the grafting of ferulic acid onto chitosan at the C-2 position. Ferulic acid grafted chitosan - prepared using a mole ratio of chitosan to ferulic acid of 1:1, reaction temperature of 60°C, and reaction time of 3h - possessed the highest ferulic acid substitution degree, i.e. 0.37. Although ferulic acid grafted chitosan showed reduced crystallinity (∼10%) and decreased decomposition temperature (∼55°C) as compared to chitosan, it exhibited greater radical scavenging activity (∼55%) and was soluble in water (up to 1.3mg/mL). The improved antioxidant property and water solubility of this chitosan derivative could open a wide range of applications, particularly its use as an antioxidant in food, food packaging, biomedical, pharmaceutical and cosmetics industries.
本工作旨在通过碳二亚胺介导的偶联反应将阿魏酸接枝到壳聚糖上,以提高壳聚糖的抗氧化活性和水溶性。紫外可见分光光度法、傅里叶变换红外光谱、(1)H 核磁共振和茚三酮试验证实了阿魏酸在壳聚糖的 C-2 位接枝。采用壳聚糖与阿魏酸摩尔比为 1:1、反应温度为 60°C、反应时间为 3h 的条件制备的阿魏酸接枝壳聚糖具有最高的阿魏酸取代度(即 0.37)。虽然与壳聚糖相比,阿魏酸接枝壳聚糖的结晶度降低(约 10%),分解温度降低(约 55°C),但其自由基清除活性(约 55%)增强,且水溶性提高(可达 1.3mg/mL)。这种壳聚糖衍生物抗氧化性能和水溶性的提高为其在食品、食品包装、生物医学、制药和化妆品等行业作为抗氧化剂的广泛应用开辟了道路。