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J Agric Food Chem. 2015 Mar 11;63(9):2464-71. doi: 10.1021/jf505581n. Epub 2015 Feb 25.

Preparation, characterization, and biochemical activities of N-(2-Carboxyethyl)chitosan from squid pens.

Author information

1
Key Laboratory of Agricultural Products Chemical and Biological Processing Technology of Zhejiang Province, School of Biological and Chemical Engineering, Zhejiang University of Science and Technology , Hangzhou, Zhejiang 310023, People's Republic of China.

Abstract

Chitosan was prepared by alkaline N-deacetylation of β-chitin from squid pens, and N-carboxyethylated derivatives (N-CECS) with different degrees of substitution (DS) were synthesized. The carboxyethylation of the polysaccharide was identified by Fourier transform infrared, (1)H and (13)C nuclear magnetic resonance (NMR), and X-ray diffraction analyses. The DS of the derivatives was calculated by (1)H NMR and elemental analysis. All three N-CECS samples showed good water solubility at pH > 6.5. The antioxidant properties and bile acid binding capacity of the derivatives were studied in vitro. The highest bile acid binding capacity of all N-CECS reached 36.9 mg/g, which was 2.6-fold higher than that of chitosan. N-CECS showed a stronger scavenging effect on 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical ability, and EC50 values were below 2 mg/mL. The scavenging ability of N-CECS against superoxide radicals correlated well with the DS and concentration of N-CECS. These results indicated that N-carboxyethylation is a possible approach to prepare chitosan derivatives with desirable in vitro biochemical properties.

KEYWORDS:

N-(2-carboxyethyl)chitosan; antioxidant; bile acid capacity; characterization; chitosan; β-chitin

PMID:
25688444
DOI:
10.1021/jf505581n
[Indexed for MEDLINE]

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