Synthesis, Characterization, and the Antioxidant Activity of Double Quaternized Chitosan Derivatives.
With the specialty of improving the water solubility of chitosan, quaternary ammonium salts have broadened the application of this polysaccharide in food, medicine and pesticides. To identify the effect of quaternary ammonium salts' quantity, single quaternized chitosanN-phenmethyl-N,N-dimethyl chitosan (PDCS), double quaternized chitosanN-(1-pyridylmethyl-2-ylmethyl)-N,N-dimethyl chitosan (MP2MDCS),N-(1-pyridylmethyl-3-ylmethyl)-N,N-dimethyl chitosan (MP3MDCS), andN-(1-pyridylmethyl-4-ylmethyl)-N,N-dimethyl chitosan (MP4MDCS) were designed and synthesized successfully through chemical modification of chitosan. Besides, three kinds of antioxidant activities, including hydroxyl radicals, superoxide radicals, and 1,1-Diphenyl-2-picrylhydrazyl (DPPH) radicals were tested in vitro. As shown in this paper, the scavenging ability was ranking in order of MP3MDC > MP4MDCS > MP2MDCS > PDCS > chitosan at 1.6 mg/mL in all assays. All double quaternary ammonium salts were better than chitosan or the single quaternary ammonium salt. In addition, MP3MDCS could scavenge hydroxyl radicals totally at 1.6 mg/mL. MP2MDCS and MP4MDCS with more than 90% scavenging indices both had great scavenging ability on hydroxyl radicals or DPPH radicals. Furthermore, these data demonstrated that the increasing number of the positive charge would improve the antioxidant property of chitosan derivatives, and theN-pyridinium position would influence the scavenging radical ability.
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. ljwei@yic.ac.cn.|University of Chinese Academy of Sciences, Beijing 100049, China. ljwei@yic.ac.cn.
Lijie
L
Wei
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. qli@yic.ac.cn.
Qing
Q
Li
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. wqtan@yic.ac.cn.|University of Chinese Academy of Sciences, Beijing 100049, China. wqtan@yic.ac.cn.
Wenqiang
W
Tan
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. fdong@yic.ac.cn.
Fang
F
Dong
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. fluan@yic.ac.cn.|University of Chinese Academy of Sciences, Beijing 100049, China. fluan@yic.ac.cn.
Fang
F
Luan
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China. zhanyongguo@hotmail.com.|University of Chinese Academy of Sciences, Beijing 100049, China. zhanyongguo@hotmail.com.
Zhanyong
Z
Guo
D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D048271:Chitosan / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017550:Spectroscopy, Fourier Transform Infrared
D000975:Antioxidants; D016166:Free Radical Scavengers; D048271:Chitosan
antioxidant activity; chemical modification; double quaternized chitosan; single quaternized chitosan