Zn2+配位双模板印迹聚合物的制备表征及同时萃取升麻中的阿魏酸和咖啡酸

doi:10.16085/j.issn.1000-6613.2016.04.026

化工进展 ›› 2016, Vol. 35 ›› Issue (04): 1132-1139.DOI: 10.16085/j.issn.1000-6613.2016.04.026

Zn²⁺配位双模板印迹聚合物的制备表征及同时萃取升麻中的阿魏酸和咖啡酸

王素素¹, 张月¹, 李辉^1,2

1. 吉首大学化学化工学院, 湖南吉首 416000;
2. 植物资源保护与利用湖南省高校重点实验室, 湖南吉首 416000

收稿日期:2015-09-14 修回日期:2015-10-27 出版日期:2016-04-05 发布日期:2016-04-05
通讯作者: 李辉,教授,研究方向为生命科学中的分离分析新方法.E-mail:lihuijsdx@163.com.
作者简介:王素素(1988-),女,研究生,研究方向为生命科学中的分离分析新方法.E-mail:545197163@qq.com.
基金资助:
国家自然科学基金面上项目(21077042)、湖南省高校科技创新团队支持计划、吉首大学研究生培养创新基地开放项目(2014KFXM02)及吉首大学研究生专项(37).

Preparation and characterization of Zn²⁺-bi-templates imprinted polymers for the simultaneous extraction of ferulic acid and caffeic acid in Rhizoma Cimicifugae

WANG Susu¹, ZHANG Yue¹, LI Hui^1,2

1. College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, Hunan, China;
2. Key Laboratory of Plant Resource Conservation and Utilization, Jishou University, Jishou 416000, Hunan, China

Received:2015-09-14 Revised:2015-10-27 Online:2016-04-05 Published:2016-04-05

摘要/Abstract

摘要： 以Zn²⁺-阿魏酸-咖啡酸配合物为模板制备了双分子印迹聚合物,优化了制备条件,用傅里叶红外光谱和扫描电镜对分子印迹聚合物进行结构表征,测试了分子印迹聚合物的吸附特性,探讨了分子印迹聚合物固相萃取应用效能并对萃取条件进行了优化.结果表明,当预反应混合液中金属离子、模板总量(阿魏酸-咖啡酸摩尔比为2:3)、功能单体及交联剂用量比为1:1:3:30(摩尔比)时,所得印迹聚合物对两种模板(阿魏酸和咖啡酸)均具有最好的吸附性能,吸附量分别达51.12mg/g和70.26mg/g.吸附动力学测试表明吸附3h,分子印迹聚合物可达到吸附平衡.用分子印迹聚合物进行固相萃取时,优化的淋洗过程为1.00mL H₂O、1.00mL甲醇-H₂O (3/7,体积比)及1.00mL甲醇-H₂O-ACN (4/4/2,体积比),洗脱溶剂为2.00mL甲醇.在优化条件下,分子印迹聚合物可同时选择富集升麻初提液中的阿魏酸和咖啡酸,二者回收率分别为92.67%和95.42%,而且产品中杂质少于用硅胶萃取所得产品.

关键词: 阿魏酸, 咖啡酸, 复合模板, 分子印迹聚合物, 固相萃取

Abstract: A group of bi-templates imprinted polymers (MIPs) was synthesized using Zn²⁺-ferulic acid-caffeic acid complex as the template. The preparation conditions were optimized. Structural characterizations were performed using FTIR and SEM and the adsorption capacity was tested. Also, the applicability of this MIP in the solid phase extraction was explored after the washing and elution conditions were optimized. Results indicated that when the molar ratio of Zn²⁺-two templates (the molar ratio of ferulic acid to caffeic acid was 2:3)-functional monomer-cross linker was 1:1:3:30 in the pre-polymerization mixture, the obtained imprinted polymer possessed the highest adsorption capacity toward two templates, with a value of 51.12mg/g for ferulic acid and 70.26mg/g for caffeic acid. The adsorption equilibrium can be reached within 3h. The optimized conditions for this MIPs phase extraction were 1.00mL H₂O, 1.00mL methanol-H₂O mixture (3/7, volume ratio) and 1.00 mL methanol-H₂O-acetonitrile mixture(4/4/2, volume ratio) for the washing procedure and 2.00 mL methanol for the elution one. This MIP revealed selective enrichment capability toward ferulic acid and caffeic acid in the crude extract of Rhizoma Cimicifugae, with recovery rates of 92.67% and 95.42% respectively under the optimized conditions. The product contains less impurities than that obtained by silica solid phase extraction.

Key words: ferulic acid, caffeic acid, mixed-templates, molecularly imprinted polymers, solid phase extraction

中图分类号:

TQ31

王素素, 张月, 李辉. Zn²⁺配位双模板印迹聚合物的制备表征及同时萃取升麻中的阿魏酸和咖啡酸[J]. 化工进展, 2016, 35(04): 1132-1139.

WANG Susu, ZHANG Yue, LI Hui. Preparation and characterization of Zn²⁺-bi-templates imprinted polymers for the simultaneous extraction of ferulic acid and caffeic acid in Rhizoma Cimicifugae[J]. Chemical Industry and Engineering Progree, 2016, 35(04): 1132-1139.

参考文献

[1] CHAPUIS F,PICHON V,LANZA F,et al. Retention mechanism of analytes in the solid-phase extraction process using molecularly imprinted polymers:application to the extraction of triazines from complex matrices[J]. J. Chromatogr. B,2004,804:93-101.
[2] YAN C,ZHANG B B,LIU W Y,et al. Rapid determination of sixteen sulfonylurea herbicides in surface water by solid phase extraction cleanup and ultra-high-pressure liquid chromatography coupled with tandem mass spectrometry[J]. J. Chromatogr. B,2011,879:3484-3489.
[3] AHMADI F,AHMADI J,RAHIMI-NASRABADI M. Computational approaches to design a molecular imprinted polymer for high selective extraction of 3,4-methylenedioxymethamphetamine from plasma[J]. J. Chromatogr. A,2011,1218:7739-7747.
[4] ALIZADEH T,GANJALI M R,ZARE M,et al. Selective determination of chloramphenicol at trace level in milk samples by the electrode modified with molecularly imprinted polymer[J]. Food Chem.,2012,130:1108-1114.
[5] XIAO D B,ZHEN L. Facile preparation of glycoprotein-imprinted 96-well microplates for enzyme-linked immunosorbent assay by boronate affinity-based oriented surface imprinting[J]. Anal. Chem.,2014,86:959-966.
[6] TAN-PHAT H,PIOTR P,FRANCIS D,et al. Molecularly imprinted polymer for recognition of 5-fluorouracil by RNA-type nucleobase pairing[J]. Anal. Chem.,2013,85:8304-8312.
[7] 谭先周,李辉,逯翠梅,等. 纳米TiO₂ 基绿原酸印迹聚合物的制备及其吸附研究[J]. 化工进展,2013,32(2):388-393.
[8] LIU C M,LIANG R P,WANG X N,et al. A versatile polydopamine platform for facile preparation of protein stationary phase for chip-based opentubular capillary electrochromatography enantioseparation[J]. J. Chromatogr. A,2013,1294:145-151.
[9] WENG X X,BI H Y,LIU B H,et al. On-chip chiral separation based onbovine serum albumin-conjugated carbon nanotubes as stationary phase ina microchanne[J]. Electrophoresis,2006,27:3129-3235.
[10] QU P,LEI J P,SHENG J,et al. Simultaneous multiple enantiosepa-ration with a one-pot imprinted microfluidic channel by microchip capillary electrochromatography[J]. Analyst,2011,136:920-926.
[11] WANG Y X,WANG S H,NIU H Y,et al. Preparationof polydopamine packed Fe₃O₄nanoparticles and their application for enrich-ment of polycyclic aromatic hydrocarbons from environmental water samples[J]. J. Chromatogr. A,2013,1283:20-26.
[12] YOU Q P,PENG M J,ZHANG Y P,et al. Preparation of magnetic dummy molecularly imprinted polymers for selective extraction and analysis of salicylic acid in Actinidia chinensis[J]. Anal. Bioanal. Chem.,2014,406(3):831-839.
[13] HU J H,FENG T,LI W L,et al. Surface molecularly imprinted polymers with synthetic dummy template for simultaneously selective recognition of nine phthalate esters[J]. J. Chromatogr. A,2014,1330:6-13.
[14] 张路,赵燕萍,张闪闪,等. 双模板分子印迹聚合物在奶粉检验中的应用研究[J]. 化学试剂,2015,37(6):495-499.
[15] 王丽敏,李英华. 铅离子双印迹吸附剂的制备及其在原子吸收光谱法测定水中痕量铅中的应用[J]. 理化检验:化学分册,2014,50(5):589-593.
[16] TAO J,YAN W,QING D,et al. Preparation of mixed-templates molecularly imprinted polymers and investigation of the recognition ability for tetracycline antibiotics[J]. Biosens. Bioelectron.,2010,25:2218-2224.
[17] 王晓明,张帆,刘莹,等. LC-MS/MS法测定升麻中咖啡酸、阿魏酸、异阿魏酸含量的研究[J]. 天津中医药,2014,31(11):686-689.
[18] SHIYI O,KIN-CHOR K. Ferulic acid:pharmaceutical functions,preparation and applications in foods[J]. Sci. Food Agric.,2004,84(11): 1261-1269.
[19] 乔福斌,张建芳,李成田,等. 灯盏花素、阿魏酸钠联合贝那普利治疗早期糖尿病肾病的疗效观察[J]. 天津中医药,2010,27(6): 458-459.
[20] 胡益勇,徐晓玉. 阿魏酸的化学和药理研究进展[J]. 中成药,2006,28(2):253-255.
[21] 许高燕,刘莹雯,银董红,等. 高效液相色谱串联质谱法测定水溶性迷迭香提取物中迷迭香酸、阿魏酸和咖啡酸的含量[J]. 分析科学学报,2006,22(5):567-569.
[22] 刘芃岩,申杰,刘磊. 复合模板印迹聚合物净化液相色谱-质谱联用法测定鱼肉中氟喹诺酮类残留[J]. 分析化学,2012,40(5): 693-698.
[23] 韦寿莲,刘玲,黎京华,等. 双分子印迹聚合物微球选择固相萃取环境和食品样品中壬基酚和双酚A[J]. 分析化学,2015,43(1):105-109.
[24] 李鸣芳,王兵. 合成引发方式对槲皮素-钴(II)配位印迹聚合物结构与性能的影响[J]. 化学学报,2012,70(7):921-928.
[25] CHITOSE M,HUI L,HISAMI M,et al. Molecularly imprinted polymer for chlorogenic acid by modified precipitation polymerization and its application to extraction of chlorogenic acid from Eucommia ulmodies leaves[J]. J. Pharmaceu. Biomed. Anal.,2015,114:139-144.
[26] LIU W F,LIU X G,YANG Y Z,et al. Selective removal of benzothiophene and dibenzothiophene from gasoline using double template molecularly imprinted polymers on the surface of carbon microspheres[J]. Fuel,2014,117:184-190.

Zn²⁺配位双模板印迹聚合物的制备表征及同时萃取升麻中的阿魏酸和咖啡酸

Preparation and characterization of Zn²⁺-bi-templates imprinted polymers for the simultaneous extraction of ferulic acid and caffeic acid in Rhizoma Cimicifugae

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	景联鹏, 顾丽莉, 师君丽, 李增良, 杨发容, 李国栋. 戊唑醇-三唑酮双模板分子印迹聚合物在烟叶农残检测中的应用[J]. 化工进展, 2022, 41(11): 6029-6037.
[2]	耿佳琦, 门园丽, 刘晨, 袁才登. 磁性石墨烯复合材料制备与应用研究进展[J]. 化工进展, 2022, 41(1): 277-285.
[3]	毛琳, 许国强, 罗晓玥, 田海希, 李辉. 温敏印迹硅胶微球对薯蓣皂素的吸附及控制释放[J]. 化工进展, 2022, 41(1): 365-372.
[4]	李子怡, 李志君, 顾丽莉, 师君丽, 陈昱安, 韩毅, 佟振浩, 孔光辉. 三唑酮分子印迹纳米球的制备及应用[J]. 化工进展, 2020, 39(7): 2706-2714.
[5]	唐录华,秦思楠,高林,高文惠. 基于对巯基苯胺膜的高灵敏己烯雌酚印迹传感器的制备及应用[J]. 化工进展, 2019, 38(11): 5074-5083.
[6]	刘军, 任汝全, 张燕如, 王冰新, 秦磊, 樊永明. 五种黄酮类分子印迹分离技术研究及应用进展[J]. 化工进展, 2019, 38(07): 3365-3376.
[7]	杨道秀1，许文江2，王林林1，蔡婀娜 1，李夏兰1. 阿魏酸酯酶的制备及在肉鸡饲料中的应用[J]. 化工进展, 2013, 32(11): 2685-2690.
[8]	谭先周1，李辉1，2，逯翠梅2，李贵1. 纳米TiO2基绿原酸印迹聚合物的制备及其吸附研究[J]. 化工进展, 2013, 32(02): 388-393.
[9]	李夏兰1，程珊影1，杨道秀1，方柏山1，2. 阿魏酸酯酶和木聚糖酶协同降解麦糟[J]. 化工进展, 2012, 31(05): 1096-1102.
[10]	牟怀燕，高云玲，付坤，姚克俭. 离子印迹聚合物研究进展[J]. 化工进展, 2011, 30(11): 2467-.
[11]	肖淑娟1，李红霞2，于守武3. 分子印迹固相萃取法提取花生壳中木犀草素 [J]. 化工进展, 2010, 29(2): 293-.
[12]	王颖，李楠. 分子印迹技术及其应用 [J]. 化工进展, 2010, 29(12): 2315-.
[13]	李辉，符再德，石慧，张朝晖，李志平，杨朝霞，石爱华. 沉淀聚合法制备高三尖杉酯碱印迹聚合物 [J]. 化工进展, 2009, 28(10): 1787-.
[14]	姚伟，高志贤，房彦军，程义勇. 沉淀聚合法制备咖啡因分子印迹聚合物微球 [J]. 化工进展, 2007, 26(6): 869-.
[15]	周庆祥，肖军平，汪卫东，周建国. 碳纳米管应用研究进展 [J]. 化工进展, 2006, 25(7): 750-.