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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湘潭大学 化工学院,湖南 湘潭 411105

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Effect of phenolic acid structure on antioxidant activity of phenolic acid-g-polymanturonic acid
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School of Chemical Engineering, Xiangtan University, Xiangtan 411105, Hunan, China

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    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。

    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.

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唐裕芳,艾世杰,严玥,李玉芹,周蓉,王唯.酚酸结构对酚酸-g-聚甘露糖醛酸抗氧化性能的影响[J].精细化工,2023,40(6):

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  • 收稿日期:2022-09-04
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  • 在线发布日期: 2023-06-28
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