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Preparation and in vitro antioxidant activities of 6‐amino‐6‐deoxychitosan and its sulfonated derivatives
Author(s) -
Yang Jianhong,
Xie Qinyue,
Zhu Jianfeng,
Zou Chang,
Chen Lingyun,
Du Yumin,
Li Dinglong
Publication year - 2015
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.22656
Subject(s) - chemistry , superoxide , antioxidant , scavenging , radical , gel permeation chromatography , hydroxyl radical , azide , organic chemistry , medicinal chemistry , polymer chemistry , polymer , enzyme
ABSTRACT The 6‐amino‐6‐deoxychitosan (NC) and their 2, 6‐di‐N‐sulfonated derivatives were prepared via N‐phthaloylation, tosylation, azidation, hydrazinolysis, reduction of azide groups and N‐sulfonation, and their structures were systematically characterized by FT‐IR, 2D HSQC NMR, XRD, gel permeation chromatography (GPC), and elemental analysis. The 6‐amino‐6‐deoxychitosan showed effect in three selected antioxidant essays, including reducing power, superoxide anion radical scavenging ability, and hydroxyl radical scavenging effect. But the factors affecting each activity were different. The reducing power and the superoxide anion radical scavenging ability of NC were strong and closely related to the amino groups in the molecular chains. Both introducing N‐sulfonated groups into NC and the concentration reduction of NC and its sulfonated derivatives decreased these activities. For the superoxide anion radical, the molecular charge property was also a significant influence factor. For the hydroxyl radical, NC only showed weak scavenging activity in a special inverse concentration‐dependent manner. However, the incorporation of N‐sulfonated groups significantly improved the scavenging activity, and the more N‐sulfonated groups, the higher the concentrations, the stronger the activity was. The results could be due to the different conformations of NC and its sulfonated derivatives in aqueous solution. © 2015 Wiley Periodicals, Inc. Biopolymers 103: 539–549, 2015.