Modification of Hydroxypropyltrimethyl Ammonium Chitosan with Organic Acid: Synthesis, Characterization, and Antioxidant Activity

Abstract

A novel and green method for the preparation of chitosan derivatives bearing organic acids was reported in this paper. In order to improve the antioxidant activity of chitosan, eight different hydroxypropyltrimethyl ammonium chitosan derivatives were successfully designed and synthesized via introducing of organic acids onto chitosan by mild and non-toxic ion exchange. The data of Fourier Transform Infrared (FTIR), 13C Nuclear Magnetic Resonance (NMR), 1H NMR, and elemental analysis for chitosan derivatives indicated the successful conjugation of organic acid salt with hydroxypropyltrimethyl ammonium chloride chitosan (HACC). Meanwhile, the antioxidant activity of the chitosan derivatives was evaluated in vitro. The results indicated that the chitosan derivatives possessed dramatic enhancements in DPPH-radical scavenging activity, superoxide-radical scavenging activity, hydroxyl radical scavenging ability, and reducing power. Furthermore, the cytotoxicity of the synthesized compounds was investigated in vitro on L929 cells and showed low cytotoxicity. Thus, the enhanced antioxidant property of all novel chitosan products might be a great advantage, while applied in a wide range of applications in the form of antioxidant in biomedical, food, and cosmetic industry.