基于ATRP技术制备姜黄素分子印迹复合膜及应用
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摘要
目的利用原子转移自由基聚合(ATRP)技术制备姜黄素分子印迹复合膜(MIM),并建立一种实际样品中姜黄素分离富集的方法。方法以姜黄素为模板分子,甲基丙烯酸为功能单体,氯化亚铜为催化剂,五甲基二乙烯三胺为配体,聚偏氟乙烯微孔滤膜为基膜,采用热聚合法制备姜黄素MIM;通过扫描电镜(SEM)考察了MIM的微观结构;采用静态和动态吸附实验对MIM的最大吸附量和吸附平衡时间进行考察,并对选择性渗透能力进行研究;以MIM为渗透装置中的膜材料,结合HPLC法对样品中的姜黄素进行分离、富集、检测。结果制备的MIM孔穴分布规则且大小均匀;最大吸附量达3.81 mg/g,且15 min即可达到吸附平衡;在阿魏酸、槲皮素和姜黄素的选择性渗透过程中,MIM对姜黄素具有较高的选择渗透能力;对生姜、姜黄、咖喱中的姜黄素进行加标回收试验,其平均回收率分别为(94.100±3.952)%、(98.300±3.637)%、(97.900±3.133)%,RSD均小于4.2%,检出限为1.76μg/kg。结论制备的姜黄素MIM吸附速度快、选择性强,为姜黄素的分离、富集提供一种新的材料,同时也为其他中药化学成分的研究提供借鉴。
Objective To prepare the molecularly imprinted composite membrane of curcumin by the atom transfer radical polymerization(ATRP) technique and develop a method for the separation and enrichment of curcumin in actual samples. Methods Curcumin MIM were prepared by thermal polymerization method using curcumin as template molecule, methylacrylic acid as functional monmers, cuprous chloride as catalyst, pentamethyldiethylenetriamine as ligand, and polyvinylidene fluoride as base membrane. The microstructure of MIM was investigated by SEM. The maximum adsorption and adsorption equilibrium time of MIM were investigated by static and dynamic adsorption experiment, and the selective penetration capacity was studied. The MIM as membrane material of osmotic device combined with HPLC was used for separation, enrichment and determination of curcumin in samples. Results The results showed that the prepared curcumin MIM had a regular distribution of pores and a uniform size. The maximum adsorption capacity was 3.81 mg/g, and the adsorption equilibrium could be achieved in 15 min. In the selective permeation process of ferulic acid, quercetin and curcumin, MIM had a high selective permeability to curcumin. The average recovery rates of curcumin in ginger, turmeric and curry were(94.100 ± 3.952)%,(98.300 ± 3.637)%, and(97.900 ± 3.133)%, respectively. The RSD was less than 4.2%. The limit of detection was 1.76 μg/kg. Conclusion The prepared MIM is a new material for strong selectivity,separation and enrichment of Chinese medicine curcumin with fast adsorption speed. At the same time, it also provides reference for chemical composition research of other Chinese materia medica.
Objective To prepare the molecularly imprinted composite membrane of curcumin by the atom transfer radical polymerization(ATRP) technique and develop a method for the separation and enrichment of curcumin in actual samples. Methods Curcumin MIM were prepared by thermal polymerization method using curcumin as template molecule, methylacrylic acid as functional monmers, cuprous chloride as catalyst, pentamethyldiethylenetriamine as ligand, and polyvinylidene fluoride as base membrane. The microstructure of MIM was investigated by SEM. The maximum adsorption and adsorption equilibrium time of MIM were investigated by static and dynamic adsorption experiment, and the selective penetration capacity was studied. The MIM as membrane material of osmotic device combined with HPLC was used for separation, enrichment and determination of curcumin in samples. Results The results showed that the prepared curcumin MIM had a regular distribution of pores and a uniform size. The maximum adsorption capacity was 3.81 mg/g, and the adsorption equilibrium could be achieved in 15 min. In the selective permeation process of ferulic acid, quercetin and curcumin, MIM had a high selective permeability to curcumin. The average recovery rates of curcumin in ginger, turmeric and curry were(94.100 ± 3.952)%,(98.300 ± 3.637)%, and(97.900 ± 3.133)%, respectively. The RSD was less than 4.2%. The limit of detection was 1.76 μg/kg. Conclusion The prepared MIM is a new material for strong selectivity,separation and enrichment of Chinese medicine curcumin with fast adsorption speed. At the same time, it also provides reference for chemical composition research of other Chinese materia medica.
引文
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[18]李鸣芳,王兵.氯霉素印迹聚合物膜的制备及其吸附性能研究[J].天津工业大学学报,2012,31(2):10-14.
[19]马秀玲,陈日耀,郑曦,等.柚皮苷分子印迹膜的水相制备与识别[J].高分子学报,2010,1(4):416-422.
[20]蔡良根,徐小艳,庞杰,等.苏丹红多孔分子印迹复合膜的制备及其性能研究[J].食品科学,2013,34(18):70-74.
[21]Wu X,Wu Y,Dong H,et al.Accelerating the design of molecularly imprinted nanocomposite membranes modified by Au@polyaniline for selective enrichment and separation of ibuprofen[J].Appl Surf Sci,2018,428:555-565.
[22]Sunil K,Paramita K,Rashmi M,et al.Designing of fluorescent and magnetic imprinted polymer for rapid,selective and sensitive detection of imidacloprid via activators regenerated by the electron transfer-atom transfer radical polymerization(ARGET-ATRP)technique[J].J Phys Chem Solids,2018,116:222-233.
[23]王靖宇.分子印迹膜制备及其膜色谱的应用研究[D].上海:华东理工大学,2010.
[24]刘春叶,张剑,尤静,等.生姜中姜黄素的高效液相色谱-质谱法检测[J].时珍国医国药,2011,22(7):1637-1639.
[2]刘芳,张倩,李锐,等.表面活性剂对姜黄素类成分水溶性与抗肝纤维化作用的影响[J].中草药,2018,49(8):1809-1815.
[3]韩伟,雷勇胜.姜黄素治疗泌尿生殖系统癌症的作用机制研究进展[J].现代药物与临床,2016,31(2):260-264.
[4]张红果,曹军平,树俊莲,等.姜黄素对小鼠皮肤移植排斥反应的影响[J].药物评价研究,2017,40(8):1082-1085.
[5]杨雪梅,邱红梅,田蜜,等.姜黄素对人过氧化物酶体增殖物激活受体γ1激活作用的研究[J].中草药,2017,48(15):3122-3126.
[6]郝东明,张丽.姜黄素联合伊立替康对结肠癌SW620细胞的体外抑制作用[J].现代药物与临床,2016,31(6):731-735.
[7]郭诗雨.姜黄素的分离纯化及药物抗肿瘤作用的研究进展[J].科技经济导刊,2016(21):101.
[8]黄容,陆昕怡,韩加伟,等.姜黄素-胡椒碱固体分散体的制备与生物利用度研究[J].中草药,2018,49(19):4528-4534.
[9]Mahmood K,Zia K M,Zuber M,et al.Recent developments in curcumin and curcumin based polymeric materials for biomedical applications:A review[J].Int JBiol Macromol,2015,81:877-890.
[10]孙永,彭明利.姜黄素及其衍生物在肝脏相关疾病中防治作用的研究进展[J].药学学报,2014(11):1483-1490.
[11]Zhang L,Qi Z,Huang Q,et al.Imprinted-like biopolymeric micelles as efficient nanovehicles for curcumin delivery[J].Colloid Surf B,2014,123:15-22.
[12]刘玉楠,张朝晖,黄小花,等.姜黄素磁性印迹固相萃取材料的制备及其应用研究[J].林产化学与工业,2014,34(6):37-43.
[13]You Q P,Zhang Y P,Zhang Q W,et al.High-capacity thermo-responsive magnetic molecularly imprinted polymers for selective extraction of curcuminoids[J].JChromatogr A,2014,1354:1-8.
[14]Thongchai W,Fukngoen P.Synthesis of curcuminoidimprinted polymers applied to the solid-phase extraction of curcuminoids from turmeric samples[J].J Pharm Anal,2018,8(1):61-70.
[15]袁波,付廷明,阚春.姜黄素分子印迹聚合物的制备与表征及其吸附性能的研究[J].华西药学杂志,2017,32(1):5-8.
[16]Liu X,Zhu L,Gao X,et al.Magnetic molecularly imprinted polymers for spectrophotometric quantification of curcumin in food[J].Food Chem,2016,202:309-315.
[17]吕俊杰,薛燕斌,乔华,等.硅胶表面高良姜素分子印迹聚合物的制备及其吸附性能[J].中草药,2018,49(21):5093-5099.
[18]李鸣芳,王兵.氯霉素印迹聚合物膜的制备及其吸附性能研究[J].天津工业大学学报,2012,31(2):10-14.
[19]马秀玲,陈日耀,郑曦,等.柚皮苷分子印迹膜的水相制备与识别[J].高分子学报,2010,1(4):416-422.
[20]蔡良根,徐小艳,庞杰,等.苏丹红多孔分子印迹复合膜的制备及其性能研究[J].食品科学,2013,34(18):70-74.
[21]Wu X,Wu Y,Dong H,et al.Accelerating the design of molecularly imprinted nanocomposite membranes modified by Au@polyaniline for selective enrichment and separation of ibuprofen[J].Appl Surf Sci,2018,428:555-565.
[22]Sunil K,Paramita K,Rashmi M,et al.Designing of fluorescent and magnetic imprinted polymer for rapid,selective and sensitive detection of imidacloprid via activators regenerated by the electron transfer-atom transfer radical polymerization(ARGET-ATRP)technique[J].J Phys Chem Solids,2018,116:222-233.
[23]王靖宇.分子印迹膜制备及其膜色谱的应用研究[D].上海:华东理工大学,2010.
[24]刘春叶,张剑,尤静,等.生姜中姜黄素的高效液相色谱-质谱法检测[J].时珍国医国药,2011,22(7):1637-1639.
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