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Rui, Liyun; Xie, Minhao; Hu, Bing; Zhou, Li; Saeeduddin, Muhammad; Zeng, Xiaoxiong
Carbohydrate polymers, 08/2017, Volume: 170Journal Article
•Chlorogenic acid (CGA) and high deacetylation degree of chitosan was conjugated.•The substitution degree of CGA reached up to 144.8mg CGA equivalent/g complex.•The solubility of conjugate was greatly enhanced due to conjugation.•The conjugate exhibited higher inhibitory effect on lipid peroxidation than CGA.•The conjugate had higher inhibition on β-carotene-linoleic acid bleaching than CGA. Chlorogenic acid-chitosan conjugate was synthesized by introducing of chlorogenic acid onto chitosan with the aid of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide and hydroxybenzotriazole. The data of UV–vis, FT-IR and NMR for chlorogenic acid-chitosan conjugates demonstrated the successful conjugation of chlorogenic acid with chitosan. Compared to chitosan, chlorogenic acid-chitosan conjugates exhibited increased solubility in distilled water, 1% acetic acid solution (v/v) or 50% ethanol solution (v/v) containing 0.5% acetic acid. Moreover, chlorogenic acid-chitosan conjugates showed dramatic enhancements in metal ion chelating activity, total antioxidant capacity, scavenging activities on 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulphonic acid) and superoxide radicals, inhibitory effects on lipid peroxidation and β-carotene-linoleic acid bleaching, and protective effect on H2O2-induced oxidative injury of PC12 cells. Particularly, chlorogenic acid-chitosan conjugate exhibited higher inhibitory effects on lipid peroxidation and β-carotene-linoleic acid bleaching than chlorogenic acid. The results suggested that chlorogenic acid-chitosan conjugates could serve as food supplements to enhance the function of foods in future.
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