硅胶表面高良姜素分子印迹聚合物的制备及其吸附性能
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摘要
目的利用表面分子印迹技术制备硅胶表面高良姜素分子印迹聚合物(MIP)。方法采用(3-氨丙基)三甲氧基硅烷对硅胶进行改性,并以改性硅胶为载体,高良姜素为模板分子,甲基丙烯酸(MAA)为功能单体,N,N′-亚甲基二丙烯酰胺(MBA)为交联剂,在优化实验条件下利用表面接枝聚合法合成高良姜素表面分子印迹聚合物(MIP)。采用红外光谱、扫描电镜对聚合物进行表征,静态吸附及竞争性吸附研究聚合物的吸附性能。结果最佳制备条件为高良姜素与MAA的物质的量比为1∶4,MAA与MBA的物质的量比为1∶7,反应温度40℃,反应时间12 h。红外光谱和扫描电镜结果显示,印迹聚合物成功接枝到硅胶表面上并出现了对高良姜素分子产生选择性识别的孔穴和位点。吸附实验表明,该MIP对高良姜素分子具有特异的识别性和较好的亲和性,相对于对照物灯盏花素和木犀草素,MIP对高良姜素的选择性系数分别为11.2和5.3。结论 MIP对高良姜素识别性好、选择性强,为中药中黄酮类化合物的分离、提取提供了一种新方法。
Objective To prepare surface molecular imprinted polymers(MIP) of galangin by using surface molecular imprinting technique.Methods Galangin MIP was prepared by surface polymerization method at the surface of silica gel,which was modified with(3-aminopropyl) trimethoxysilane,by using galangin as the template molecule,methacrylic acid(MAA) as the functional monomer,and N,N′-methylenebisacrylamide(MBA) as crosslinking agent.The polymer was characterized by infrared spectroscopy and scanning electron microscopy.And its adsorption properties were studied by static and competitive adsorption method.ResultsThe experimental research showed that the optimal preparation condition was that the molar ration of galangin to MAA was 1∶4,with molar ration of MAA to MBA 1∶7,reaction temperature 40 ℃ and reaction time 12 h.Infrared spectrum and scanning electron microscopy showed that MIP was successfully grafted on the surface of silica gel,and recognition holes and sites selectively appeared for galangin molecules.Adsorption experiments exhibited that MIP had specific recognition and good affinity for galangin molecules.Compared to the controls of breviscapine and luteolin,the selectivity coefficients of MIP to galangin were 11.2 and 5.3,respectively.Conclusion MIP has good recognition and high selectivity for galangin,which provides a new method for the separation and extraction of flavonoids from Chinese medicine.
Objective To prepare surface molecular imprinted polymers(MIP) of galangin by using surface molecular imprinting technique.Methods Galangin MIP was prepared by surface polymerization method at the surface of silica gel,which was modified with(3-aminopropyl) trimethoxysilane,by using galangin as the template molecule,methacrylic acid(MAA) as the functional monomer,and N,N′-methylenebisacrylamide(MBA) as crosslinking agent.The polymer was characterized by infrared spectroscopy and scanning electron microscopy.And its adsorption properties were studied by static and competitive adsorption method.ResultsThe experimental research showed that the optimal preparation condition was that the molar ration of galangin to MAA was 1∶4,with molar ration of MAA to MBA 1∶7,reaction temperature 40 ℃ and reaction time 12 h.Infrared spectrum and scanning electron microscopy showed that MIP was successfully grafted on the surface of silica gel,and recognition holes and sites selectively appeared for galangin molecules.Adsorption experiments exhibited that MIP had specific recognition and good affinity for galangin molecules.Compared to the controls of breviscapine and luteolin,the selectivity coefficients of MIP to galangin were 11.2 and 5.3,respectively.Conclusion MIP has good recognition and high selectivity for galangin,which provides a new method for the separation and extraction of flavonoids from Chinese medicine.
引文
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[12]廖辉,金晨,何玉琴,等.槲皮素分子印迹聚合物的合成及表征[J].中草药,2017,48(8):1537-1543.
[13]刘洋,金晨,廖辉,等.分子印迹聚合物在黄酮类化合物研究中的应用进展[J].江西中医药,2017,48(417):66-70.
[14]左振宇,张光辉,雷福厚,等.分子印迹聚合物在中药活性成分分离中的应用进展[J].中草药,2017,48(23):5019-5031.
[15]姚杰,乔华,吕俊杰,等.高良姜素分子印迹聚合物分子识别性研究[J].中草药,2014,45(18):2614-2618.
[16]Wang X,Huang P,Ma X,et al.Preparation and evaluation of magnetic core-shell mesoporous molecularly imprinted polymers for selective adsorption of tetrabromobisphenol S[J].Talanta,2017,166:300-305.
[17]李绍丽,陈芳艳,杨占,等.硅胶表面分子印迹聚合物对DEHP的选择性吸附[J].环境工程学报,2016,10(7):3694-3700.
[18]苏立强,李继姣,高源.槲皮素表面分子印迹聚合物的制备及其应用研究[J].化学通报,2016,79(4):349-354.
[19]曹林交,高保娇,胡伟民.生物碱分子表面印迹聚合物材料的设计与制备及其分子识别特性[J].应用化学,2014,31(12):1390-1398.
[20]Zhang Y Y,Gao B J,Xu Z Q.Adsorption properties of polyvinyl-alcohol-grafted particles toward genistein driven by hydrogen-bond interaction[J].J Phys Chem B,2013,117(18):5730-5736.
[2]张旭光,尹航,陈峰,等.高良姜素药理活性的研究进展[J].中国现代中药,2016,18(11):1532-1536.
[3]陈淑梅.高良姜素诱导人乳头瘤病毒阳性的宫颈癌细胞凋亡实验研究[J].中草药,2017,48(5):941-945.
[4]Kim Y R,Kim M A,Cho H J,et al.Galangin prevents aminoglycoside-induced ototoxicity by decreasing mitochondrial production of reactive oxygen species in mouse cochlear cultures[J].Toxicol Lett,2016,245:78-85.
[5]高莉,霍仕霞,彭晓明,等.高良姜素对氢醌诱导的白癜风小鼠模型的影响[J].中草药,2014,45(16):2358-2363.
[6]Huang H Z,Chen A Y,Rojanasakul Y,et al.Dietary compounds galangin and myricetin suppress ovarian cancer cell angiogenesis[J].J Funct Foods,2015,15:464-475.
[7]许奕夫,姚鑫.高良姜素抑制乳腺癌转移作用机制研究[J].中草药,2016,47(10):1731-1738.
[8]张竟,李振国.高效液相色谱法测定蜂胶片中白杨素和高良姜素的含量[J].中医研究,2015,28(6):70-72.
[9]傅力明,吕俊杰,乔华,等.荧光光度法测定中药高良姜中高良姜素的含量[J].中国药物与临床,2014,14(11):1531-1532.
[10]徐静,曹学丽,尹鹭,等.逆流色谱与硅胶柱色谱相结合分离纯化高良姜中高良姜素[J].食品科学,2013,34(4):55-58.
[11]黄浩锐,黎大瑞,罗木城,等.超临界CO2流体萃取技术提取高良姜素的应用进展[J].中国医药导刊,2009,11(3):501-502.
[12]廖辉,金晨,何玉琴,等.槲皮素分子印迹聚合物的合成及表征[J].中草药,2017,48(8):1537-1543.
[13]刘洋,金晨,廖辉,等.分子印迹聚合物在黄酮类化合物研究中的应用进展[J].江西中医药,2017,48(417):66-70.
[14]左振宇,张光辉,雷福厚,等.分子印迹聚合物在中药活性成分分离中的应用进展[J].中草药,2017,48(23):5019-5031.
[15]姚杰,乔华,吕俊杰,等.高良姜素分子印迹聚合物分子识别性研究[J].中草药,2014,45(18):2614-2618.
[16]Wang X,Huang P,Ma X,et al.Preparation and evaluation of magnetic core-shell mesoporous molecularly imprinted polymers for selective adsorption of tetrabromobisphenol S[J].Talanta,2017,166:300-305.
[17]李绍丽,陈芳艳,杨占,等.硅胶表面分子印迹聚合物对DEHP的选择性吸附[J].环境工程学报,2016,10(7):3694-3700.
[18]苏立强,李继姣,高源.槲皮素表面分子印迹聚合物的制备及其应用研究[J].化学通报,2016,79(4):349-354.
[19]曹林交,高保娇,胡伟民.生物碱分子表面印迹聚合物材料的设计与制备及其分子识别特性[J].应用化学,2014,31(12):1390-1398.
[20]Zhang Y Y,Gao B J,Xu Z Q.Adsorption properties of polyvinyl-alcohol-grafted particles toward genistein driven by hydrogen-bond interaction[J].J Phys Chem B,2013,117(18):5730-5736.
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