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漆酚低聚物的制备及其抗菌、抗氧化和热稳定性评估。

Urushiol oligomer preparation and evaluations of their antibacterial, antioxidant, and thermal stability.

作者信息

Chen Hongxia, Zhou Hao, Qi Zhiwen, Xue Xingying, Wang Chengzhang

机构信息

Institute of Chemical Industry of Forest Products, CAF, Nanjing, China.

National Engineering Laboratory for Biomass Chemical Utilization, Key and Open Laboratory of Forest Chemical Engineering, SFA, Nanjing, China.

出版信息

J Biomater Sci Polym Ed. 2025 Mar;36(4):481-494. doi: 10.1080/09205063.2024.2409483. Epub 2024 Oct 8.

Abstract

There have been studies published on the composition and coating uses of raw lacquers following enzymatic oxidative polymerization. The change of urushiol' thermal stability and biological activity following polymerization to create oligomer, however, has received little attention. This work using silica gel column chromatography to separate urushiol and urushiol oligomer from polymerized raw lacquer and assessed its antibacterial, antioxidant, and thermal stability in an effort to decrease the allergenicity of urushiol and increase its application. By using gel chromatography, the urushiol oligomer were discovered to be polymers with 2-5 degrees of polymerization. According to characterization results from techniques like UV, FT-IR, and H NMR, urushiol was converted into urushiol oligomer by addition reactions, and C-C coupling. The findings demonstrated that the urushiol oligomer' IC values for scavenging DPPH and ABTS free radicals were 40.8 and 27.4 μg/mL, respectively, and that their minimum inhibitory concentrations against and were 250 and 125 μg/mL. The urushiol oligomer's thermogravimetric differential curve peak temperature (461.8 °C) was higher than urushiol's (239.5 °C), indicating that urushiol undergoes polymerization with enhanced thermal stability. The study's findings establish a foundation for the use of polymerized urushiol and urushiol oligomer in applications including functional materials and additives.

摘要

关于酶促氧化聚合后生漆的成分及涂层用途已有研究发表。然而,漆酚聚合形成低聚物后其热稳定性和生物活性的变化却很少受到关注。这项工作采用硅胶柱色谱法从聚合生漆中分离漆酚和漆酚低聚物,并评估其抗菌、抗氧化和热稳定性,以降低漆酚的致敏性并扩大其应用范围。通过凝胶色谱法发现,漆酚低聚物是聚合度为2至5的聚合物。根据紫外光谱、傅里叶变换红外光谱和核磁共振氢谱等技术的表征结果,漆酚通过加成反应和碳 - 碳偶联转化为漆酚低聚物。研究结果表明,漆酚低聚物清除DPPH和ABTS自由基的IC值分别为40.8和27.4μg/mL,它们对大肠杆菌和金黄色葡萄球菌的最低抑菌浓度分别为250和125μg/mL。漆酚低聚物的热重差示曲线峰值温度(461.8°C)高于漆酚的(239.5°C),表明漆酚聚合后热稳定性增强。该研究结果为聚合漆酚和漆酚低聚物在功能材料和添加剂等应用方面奠定了基础。

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