Synthesis and antioxidant property of novel 1,2,3-triazole-linked starch derivatives via ‘click chemistry’

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• 作者：Wenqiang Tan^a ; ^b ; Qing Li^a ; Wancong Li^a ; ^b ; Fang Dong^a ; Zhanyong Guo^a ; ^{zhanyongguo@hotmail.com" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Starch derivatives ; Click chemistry ; Antioxidant activity
• 刊名：International Journal of Biological Macromolecules
• 出版年：2016
• 出版时间：January 2016
• 年：2016
• 卷：82
• 期：Complete
• 页码：404-410
• 全文大小：1565 K

文摘

Based on the copper (I) catalyzed Huisgen azide-alkyne cycloaddition (click chemistry), the novel synthesis of a variety of 1,2,3-triazole-linked starch derivatives was developed, including 6-hydroxymethyltriazole-6-deoxy starch (HMTST), 6-hydroxyethyltriazole-6-deoxy starch (HETST), 6-hydroxypropyltriazole-6-deoxy starch (HPTST), and 6-hydroxybutyltriazole-6-deoxy starch (HBTST). Their antioxidant properties against hydroxyl-radical, DPPH-radical, and superoxide-radical were evaluated in vitro, respectively. The antioxidant activity of the obtained novel amphiprotic starch derivatives via ‘click reaction’ exhibited remarkable improvement over starch. And the scavenging effect indices of most of the products were higher than 60% at 1.6 mg/mL against hydroxyl-radical and DPPH-radical. Moreover, the scavenging effect of the products against superoxide-radical attained 90% above at 0.1 mg/mL. Generally, the antioxidant activity decreased in the order: HBTST > HPTST > HETST > HMTST > starch. Furthermore, the order of their antioxidant activity was consistent with the electron-donating ability of different substituted groups of the 1,2,3-triazoles. The substituted groups with stronger electron supplying capacity provided more electrons to the various radicals, which relatively enhanced the capacity for scavenging free radicals.