梁宇岚;杨鑫;潘玲玲;吴亚芬;李斐;万娜;周翔;刘波;李斌;
LIANG Yu-lan;YANG Xin;PAN Ling-ling;WU Ya-fen;LI Fei;WAN Na;ZHOU Xiang;LIU Bo;LI Bin;Pharmacy College,Jiangxi University of Traditional Chinese Medicine;School of Chemical and Technology,Harbin Institute of Technology;

• 1:江西中医药大学药学院
• 2:哈尔滨工业大学化工与化学学院

摘要(Abstract)：

分子印迹技术以其高选择性、特异识别性等特点,在黄酮、生物碱、多酚类等化合物的分离分析中广泛应用,但是其在萜类化合物中的应用研究较少。该文通过文献调研统计,系统探讨功能单体、交联剂和致孔剂等常见合成元素对聚合物性能的影响,重点对萜类分子印迹技术在固相萃取、传感器、膜分离、色谱分离等方面的研究进行了总结,并分析目前该技术存在的缺点和改进方向,为更好将分子印迹技术应用于萜类化合物分离分析提供参考。
Molecular imprinting technology is widely used in the separation and analysis of compounds such as flavonoids,alkaloids and polyphenols,due to its high selectivity and specific recognition and so on. However,no much of attention has been paid to the terpenoids. This paper is aimed to not only review the effects of common synthetic elements such as functional monomers,cross-linking agents and porogens on the polymer properties,but also highlight the application of terpene molecular imprinting in solid phase extraction,sensor,membrane separation and chromatographic separation by means of statistical analysis of literature. Furthermore,the shortcomings and improvement directions are discussed. We believed that this paper could provide references for better applications of molecular imprinting techniques to the analysis of terpenoid compounds.

关键词(KeyWords)： 分子印迹技术;萜类化合物;应用
molecular imprinting technology;terpenoids;application

Abstract:

Keywords:

基金项目(Foundation): 国家自然科学基金项目(81760708);; 江西省主要学科学术和技术带头人资助计划项目(20162BCB22016);; 江西省教育厅重点项目(GJJ160809)

作者(Authors): 梁宇岚;杨鑫;潘玲玲;吴亚芬;李斐;万娜;周翔;刘波;李斌;
LIANG Yu-lan;YANG Xin;PAN Ling-ling;WU Ya-fen;LI Fei;WAN Na;ZHOU Xiang;LIU Bo;LI Bin;Pharmacy College,Jiangxi University of Traditional Chinese Medicine;School of Chemical and Technology,Harbin Institute of Technology;

DOI: 10.19540/j.cnki.cjcmm.20171027.002

参考文献(References)：

• [1]Chen L,Xu S,Li J.Recent advances in molecular imprinting technology:current status,challenges and highlighted applications[J].Chem Soc Rev,2011,40(5):2922.
• [2]Whitcombe M J,Kirsch N,Nicholls I A.Molecular imprinting science and technology:a survey of the literature for the years2004-2011[J].J Mol Recognit,2014,27(6):297.
• [3]谭天伟.分子印迹技术及应用[M].北京:化学工业出版社,2006:6.
• [4]孙宝维,杨敏莉,李元宗,等.模板结构与分子印迹效果间关系的研究[J].化学学报,2003,61(6):878.
• [5]袁琼辉,汤又文.新型功能单体分子印迹聚合物的研究进展[J].化学通报,2009(8):707.
• [6]Sibrian-Vazquez M,Spivak D A.Enhanced enantioselectivity of molecularly imprinted polymers formulated with novel cross-linking monomers[J].Macromolecules,2003,36(14):5105.
• [7]Sibrian-Vazquez M,Spivak D A.Molecular imprinting made easy[J].J Am Chem Soc,2004,126(25):7827.
• [8]夏赞韶,贺福元,邓凯文,等.中药分子印迹技术对中医药理论的特殊影响[J].中国中药杂志,2013(8):1266.
• [9]Piletsky S A,Piletska E V,Karim K,et al.Polymer cookery:influence of polymerization conditions on the performance of molecularly imprinted polymers[J].Macromolecules,2002,35(19):7499.
• [10]范宁伟,赵文生,翦英红.溶剂对香兰素分子印迹聚合物制备的影响[J].化学研究与应用,2009,21(3):327.
• [11]董文国,闫明,吴国是,等.溶剂对分子印迹聚合物分子识别能力的影响:实验研究与计算量子化学分析[J].化工学报,2005,56(7):1247.
• [12]Xie J,Cai C,Yang H,et al.Synthesis and application of molecularly imprinted polymer on selective solid-phase extraction for the determination of artemisinin in Artemisia annua L[J].Anal Lett,2013,46(1):107.
• [13]Chen B,Liu C,Ge L,et al.Localized surface plasmon resonance gas sensor of Au nano-islands coated with molecularly imprinted polymer:influence of polymer thickness on sensitivity and selectivity[J].Sens Actuators B Chem,2016,231:787.
• [14]Chen B,Liu C,Hayashi K.Selective terpene vapor detection using molecularly imprinted polymer coated Au nanoparticle LSPRsensor[J].IEEE Sens J,2014,14(10):3458.
• [15]Chen B,Liu C,Xie Y,et al.Localized surface plasmon resonance gas sensor based on molecularly imprinted polymer coated Au nano-island films:influence of nanostructure on sensing characteristics[J].IEEE Sens J,2016,16(10):3532.
• [16]Chen B,Liu C,Sun X,et al.Molecularly imprinted polymer coated Au nanoparticle sensor forα-pinene vapor detection[C].Kagawa:2013 IEEE.ICMA,2013.
• [17]Hawari H F,Samsudin N M,Shakaff A Y M,et al.Development of interdigitated electrode molecular imprinted polymer sensor for monitoring alpha pinene emissions from mango fruit[J].Procedia Engineering,2013,53:197.
• [18]Lieberzeit P A,Rehman A,Iqbal N,et al.QCM sensor array for monitoring terpene emissions from odoriferous plants[J].Monatsh Chem,2009,140(8):947.
• [19]Iqbal N,Mustafa G,Rehman A,et al.QCM-arrays for sensing terpenes in fresh and dried herbs via bio-mimetic MIP layers[J].Sensors,2010,10(7):6361.
• [20]Masoumi M,Jahanshahi M.Synthesis and recognition of nano pore molecularly imprinted polymers of thymol on the surface of modified silica nanoparticles[J].Adv Polym Tech,2016,35(2):221.
• [21]Motherwell W B,Bingham M J,Pothier J,et al.A study of some molecularly imprinted polymers as protic catalysts for the isomerisation ofα-pinene oxide to trans-carveol[J].Tetrahedron,2004,60(14):3231.
• [22]Hedin-Dahlstr9m J,Shoravi S,Wikman S,et al.Stereoselective reduction of menthone by molecularly imprinted polymers[J].Tetrahedron-Asymmetr,2004,15(15):2431.
• [23]Ji W,Zhang M,Gao Q,et al.Preparation of hydrophilic molecularly imprinted polymers via bulk polymerization combined with hydrolysis of ester groups for selective recognition of iridoid glycosides[J].Anal Bioanal Chem,2016,408(19):5319.
• [24]Ji W,Wang T,Liu W,et al.Water-compatible micron-sized monodisperse molecularly imprinted beads for selective extraction of five iridoid glycosides from Cornus officinalis fructus[J].J Chromatogr A,2017,1504:1.
• [25]Ji W,Zhang M,Liu W,et al.Development of hydrophilic magnetic molecularly imprinted polymers by directly coating onto Fe3O4with a water-miscible functional monomer and application in a solid-phase extraction procedure for iridoid glycosides[J].RSCAdv,2016,6(56):50487.
• [26]Huang H,Wang X,Ge H,et al.Multifunctional magnetic cellulose surface-imprinted microspheres for highly selective adsorption of artesunate[J].ACS Sustainable Chem Eng,2016,4(6):3334.
• [27]Gong X Y,Cao X J.Preparation of molecularly imprinted polymers for artemisinin based on the surfaces of silica gel[J].J Biotechnol,2011,153(1):8.
• [28]Yang B,Cao X.Synthesis of the artemisinin-imprinting polymers on silica surface and its adsorption behavior in supercritical CO2fluid[J].AICh E J,2011,57(12):3514.
• [29]Wu Y,Yan M,Yan Y,et al.Fabrication and evaluation of artemisinin-imprinted composite membranes by developing a surface functional monomer-directing prepolymerization system[J].Langmuir,2014,30(49):14789.
• [30]Wu Y L,Meng M J,Liu X,et al.Efficient one-pot synthesis of artemisinin-imprinted membrane by direct surface-initiated AGET-ATRP[J].Sep Purif Technol,2014,131:117.
• [31]Cui J,Wu Y,Meng M,et al.Bio-inspired synthesis of molecularly imprinted nanocomposite membrane for selective recognition and separation of artemisinin[J].J Appl Polym Sci,2016,133(19):9.
• [32]Zhou J,Sun X,Wang K.Sensitive artemisinin electrochemical sensor based on polymerized molecularly imprinted membranes[J].Int J Electrochem Sc,2016,11(4):3114.
• [33]Bai H,Wang C,Chen J,et al.A novel sensitive electrochemical sensor based on in-situ polymerized molecularly imprinted membranes at graphene modified electrode for artemisinin determination[J].Biosens Bioelectron,2015,64:352.
• [34]Fan J P,Xu X K,Xu R,et al.Preparation and characterization of molecular imprinted polymer functionalized with core/shell magnetic particles(Fe3O4@Si O2@MIP)for the simultaneous recognition and enrichment of four taxoids in Taxus×media[J].Chem Eng J,2015,279:567.
• [35]Yin X,Liu Q,Jiang Y,et al.Development of andrographolide molecularly imprinted polymer for solid-phase extraction[J].Spectrochim Acta A,2011,79(1):191.
• [36]Chen F F,Wang R,Shi Y P.Molecularly imprinted polymer for the specific solid-phase extraction of kirenol from Siegesbeckia pubescens herbal extract[J].Talanta,2012,89:505.
• [37]Claude B,Viron-Lamy C,Haupt K,et al.Synthesis of a molecularly imprinted polymer for the solid-phase extraction of betulin and betulinic acid from plane bark[J].Phytochem Anal,2010,21(2):180.
• [38]Claude B,Morin P,Lafosse M,et al.Selective solid-phase extraction of a triterpene acid from a plant extract by molecularly imprinted polymer[J].Talanta,2008,75(2):344.
• [39]Liu H,Liu C,Yang X,et al.Solid-phase extraction of ursolic acid from herb usingβ-cyclodextrin-based molecularly imprinted microspheres[J].J Sep Sci,2008,31(20):3573.
• [40]Chen X,Zhang Z,Yang X,et al.Molecularly imprinted polymers based on multi-walled carbon nanotubes for selective solid-phase extraction of oleanolic acid from the roots of kiwi fruit samples[J].Talanta,2012,99:959.
• [41]Cirillo G,Curcio M,Parisi O I,et al.Molecularly imprinted polymers for the selective extraction of glycyrrhizic acid from liquorice roots[J].Food Chem,2011,125(3):1058.
• [42]张佳慧.磁性分子印迹微球定向富集苦瓜藤三萜类化合物[D].南昌:南昌大学,2016
• [43]马雄辉,李建平,王超,等.生物大分子印迹传感器研究进展[J].分析化学,2016,44(1):152.
• [44]Jung J H,Lee S P.Biomimetic MIP terpene sensors adding conductive polymers[J].J Sens Sci Technol,2012,21(5):345.
• [45]Cormack P A G,Elorza A Z.Molecularly imprinted polymers:synthesis and characterisation[J].J Chromatogr B,2004,804(1):173.
• [46]杨座国,许振良,邴乃慈.分子印迹膜的研究进展[J].化工进展,2006,25(2):131.
• [47]张培斌,唐安琪,路景驭,等.基于贻贝仿生化学的分离功能材料[J].功能高分子学报,2017,30(1):1.
• [48]Yoshikawa M,Murakoshi K,Kogita T,et al.Chiral separation membranes from modified polysulfone having myrtenal-derived terpenoid side groups[J].Eur Polym J,2006,42(10):2532.
• [49]Wulff G,Gross T,Sch9nfeld R.Enzyme models based on molecularly imprinted polymers with strong esterase activity[J].Angew Chem Int Edit,1997,36(18):1962.
• [50]Alexander C,Smith C R,Whitcombe M J,et al.Imprinted polymers as protecting groups for regioselective modification of polyfunctional substrates[J].J Am Chem Soc,1999,121(28):6640.
• [51]Damen J,Neckers D C.Stereoselective syntheses via a photochemical template effect[J].J Am Chem Soc,1980,102(9):3265.
• [52]Chen L,Wang X,Lu W,et al.Molecular imprinting:perspectives and applications[J].Chem Soc Rev,2016,45(8):2137.