Page 206 - 《精细化工》2023年第6期

第 40 卷第 6 期 精 细 化 工 Vol.40, No.6
20 23 年 6 月 FINE CHEMICALS June 2023

食品与饲料用化学品
酚酸结构对酚酸-g-聚甘露糖醛酸抗氧化性能的影响

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唐裕芳，杨雨欣，艾世杰，严 玥，李玉芹 ，周 蓉，王 唯
（湘潭大学 化工学院，湖南 湘潭 411105）

摘要：海藻酸钠水解产物聚甘露糖醛酸（PM）的羧基与乙二胺（EDA）的一个氨基反应制得了中间体 PM-EDA，
PM-EDA 分别与 8 种酚酸（PA）接枝共聚，制得了 8 种接枝共聚物酚酸-g-聚甘露糖醛酸（PA-g-PM）。对 PM-EDA
的制备条件进行了优化，探究了 PA 结构对 PA-g-PM 抗氧化活性的影响。结果表明，在 n(PM)∶n(EDA)=1∶1.5，
n(PM)∶n（碳二亚胺）∶n（N-羟基琥珀酰亚胺）=1∶2∶1，pH 8.0 条件下反应 24 h，获得最高取代度（17.27%）
的 PM-EDA。8 种 PA-g-PM 的接枝率在（4.171±0.16）~（8.880±0.32） mg 没食子酸/g 之间。UV-Vis、FTIR、
XRD 表征证实酚酸已成功接枝到 PM 上。相比于 PM，8 种 PA-g-PM 对 1,1-二苯基-2-三硝基苯肼（DPPH）自由
基的清除率和对铁的还原力均显著提升。PA-g-PM 的抗氧化性能与其中的酚羟基个数呈正相关关系，含有对位
酚羟基的 PA-g-PM 的抗氧化性能优于含有邻位酚羟基的 PA-g-PM 的抗氧化性能，PA-g-PM 中的酚羟基被甲氧基
取代后抗氧化性能减弱。
关键词：海藻酸钠；聚甘露糖醛酸；酚酸；抗氧化性能；食品化学品
中图分类号：TS202.3；TQ658 文献标识码：A 文章编号：1003-5214 (2023) 06-1356-10

Effect of phenolic acid structure on antioxidant activity of
phenolic acid-g-polymanturonic acid

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TANG Yufang, YANG Yuxin, AI Shijie, YAN Yue, LI Yuqin , ZHOU Rong, WANG Wei
（School of Chemical Engineering, Xiangtan University, Xiangtan 411105, Hunan, China）

Abstract: Eight kinds of graft copolymers phenolic acid-g-polymanturonic acid (PA-g-PM) were prepared
by graft copolymerization of eight phenolic acids (PA) and intermediate PM-EDA, which was synthesized
from the reaction between the carboxy group of polymanuronic acid (PM), a hydrolysate of sodium alginate,
and the amino group of ethylenediamine (EDA). The preparation conditions of PM-EDA were optimized，
and the influence of PA structure on the antioxidant activities of PA-g-PM were investigated. The results
showed that under the conditions of n(PM) ∶ n(EDA) =1 ∶ 1.5, n(PM) ∶ n(carbodiimide) ∶
n(N-hydroxysuccinimide)= 1∶2∶1, pH 8.0, and reaction time of 24 h, PM-EDA with the highest
substitution degree of 17.27% was obtained. Data from UV-Vis, FTIR and XRD analyses showed that
phenolic acids were successfully graft onto PM, with grafting rates ranging from (4.171±0.16) to
(8.880±0.32) mg gallic acid/g for the eight copolymers. Compared with PM, all eight PA-g-PM copolymers
exhibited significantly enhanced 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging rate and iron reducing
power. The antioxidant performance of PA-g-PM was positively correlated with the number of phenolic
hydroxyl groups contained, with that of PA-g-PM possessing para-phenolic hydroxyl group superior to that
of possessing ortho-phenolic hydroxyl group. Meanwhile, PA-g-PM with methoxy group in replacement of
phenolic hydroxyl group showed weakened antioxidant activity.
Key words: sodium alginate; ploymannuronic acid; phenolic acid; antioxidation; food chemicals

收稿日期：2022-09-04; 定用日期：2023-01-06; DOI: 10.13550/j.jxhg.20220827
基金项目：湖南省教育厅重点项目（20A472）；湖南省自然科学基金面上项目（2021JJ30660）；湖南省大学生创新创业基
金（S202010530046）；湘潭大学 2021 年度大学生创新创业训练计划项目
作者简介：唐裕芳（1970—），女，副教授，E-mail：tyfchky@xtu.edu.cn。联系人：李玉芹（1979—），女，教授，E-mail：
yuqinli2004@xtu.edu.cn。