含辣素衍生结构单体及其聚合物的合成、抑菌与抑藻性能

doi:10.11896/j.issn.1005-023X.2018.02.007

《材料导报》期刊社

2018, Vol. 32

Issue (2): 193-197 https://doi.org/10.11896/j.issn.1005-023X.2018.02.007

物理材料研究｜材料

含辣素衍生结构单体及其聚合物的合成、抑菌与抑藻性能

张晓春,于良民,姜晓辉

中国海洋大学海洋化学理论与工程技术教育部重点实验室,青岛 266100

Synthesis, Bacteriostatic and Anti-alga Capability of Monomers and Polymers Containing Capsaicin

Xiaochun ZHANG,Liangmin YU,Xiaohui JIANG

Key Laboratory of Marine Chemistry Theory and Technology of Ministry of Education, Ocean University of China,Qingdao 266100

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摘要

以取代芳烃和N-羟甲基丙烯酰胺为原料,采用傅克烷基化反应合成了四种含辣素衍生结构单体:4-羟基-2-甲基-5-甲硫基苄基丙烯酰胺(A)、2-羟基-4-丙烯酰胺甲基-5-甲硫基-6-甲基苄基丙烯酰胺(B)、3-丙烯酰胺甲基-2-羟基苯甲酰胺(C)和1-丙烯酰胺甲基-2-萘酚(D),并通过红外光谱(IR)和核磁氢谱( ¹H NMR)对其结构进行了表征。抑菌实验结果表明化合物D对两种受试菌(金黄色葡萄球菌和大肠杆菌)的抑制活性最高,最小抑菌浓度均可达到0.187 5 mg/mL,且D对两种受试藻(三角褐指藻和新月菱形藻)的抑制活性也最高。以四种化合物为功能单体合成出树脂,树脂对受试藻均具有较高的抑制活性,含化合物D的树脂的抑制活性最高,72 h后抑制率均可达到50%以上。

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	张晓春
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关键词: 辣素衍生物树脂合成抑菌性能抑藻性能

Abstract:

Four compounds (4-hydroxy-2-methyl-5-methylthio benzyl acrylamide (A), 2-hydroxy-4-acrylamide methyl-5-methylthio-6-methyl benzyl acrylamide (B), 3-acrylamide methyl-2-hydroxy benzamide (C), 1-acrylamide methyl-2-naphthol (D)) containing capsaicin moieties were synthesized with substituted aromatic and N-methylol acrylamide by Friedel-Crafts alkylation reaction, and their structures were characterized by infrared spectroscopy (IR) and hydrogen nuclear magnetic spectra ( ¹H NMR). The results of antibacterial test showed that the best inhibitory activity can be observed on Staphylococcus aureus and Escherichia coli with compound D, reaching the minimum inhibitory concentration (MIC) of 0.187 5 mg/mL. Moreover, the inhibitory activity of D on the two tested algae performed the best. The resins synthesized with four compounds as functional monomers were verified to have great inhibitory activity on tested algae. Besides, the best inhibitory activity is obtained on resin comprised of compound D, which has the inhibition rate of over 50% after 72 h.

Key words: capsaicin derivatives resin synthesis antibacterial activity anti-alga capability

出版日期: 2018-01-25 发布日期: 2018-01-25

ZTFLH:

O621.3

基金资助: 中央高校基本科研业务费专项资金(201562026;201413024);国家科技支撑计划(2012BAB15B02);教育部博士点专项基金(20130132130001)

引用本文:

张晓春,于良民,姜晓辉. 含辣素衍生结构单体及其聚合物的合成、抑菌与抑藻性能[J]. 《材料导报》期刊社, 2018, 32(2): 193-197.
Xiaochun ZHANG,Liangmin YU,Xiaohui JIANG. Synthesis, Bacteriostatic and Anti-alga Capability of Monomers and Polymers Containing Capsaicin. Materials Reports, 2018, 32(2): 193-197.

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https://www.mater-rep.com/CN/10.11896/j.issn.1005-023X.2018.02.007 或 https://www.mater-rep.com/CN/Y2018/V32/I2/193

图1 目标物的结构式

表1 含不同辣素衍生结构丙烯酸树脂的合成

图2 A的红外谱和核磁氢谱

图3 树脂的红外光谱

表2 受试化合物的MIC值(单位:mg/mL)

图4 受试化合物对大肠杆菌的抑制作用

图5 受试化合物对金黄色葡萄球菌的抑制作用

图6 受试物对三角褐指藻生长曲线的影响

图7 受试物对新月菱形藻生长曲线的影响

表3 树脂对藻的抑制率(%)

图8 (a)三角褐指藻和(b)新月菱形藻的工作曲线

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