Application of Molecularly Imprinted Polymers Towards Efficient Extraction and Chromatographic Detection of Natural Products
Main Article Content
Abstract
The expanding use of phytopharmaceuticals, as a more safe and efficient remedies for different pharmacological activities and as dietary and nutritional supplements has created the need to have a more eco-friendly, and selective extraction techniques to enhance the economic and environmental greenness of the applied traditional extraction methods. Recently, the application of molecularly imprinted polymers (MIPs), has grasped the attention in the field of natural products due to their ease of design and preparation with specific recognition cavities that can selectively bind to a target analyte. The present review aims not only to discuss the application of MIPs with the past ten years in the field solid phase extraction of different classes of natural products (NPs) but also their impact on the effectiveness of chromatographic separation and detection will be elaborated. Based on their performance, MIPs represent a promising class of artificial adsorbents that can be commercialized for beneficiary extraction of natural products with much less consumption of solvents and higher selectivity when compared to the traditional types of chromatographic adsorbents besides the possibility of their 3D printing to create more optimized and uniform manifolds to match the different types of extraction and detection applications of natural products (NPs).
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References
Hatfield G. Healing Threads: Traditional Medicines of the highlands and islands. Folklore. 1997;108:136.
Duke JA. Duke’s Handbook of Medicinal Plants of Latin America. CRC press; 2008.
Metwaly AM, Ghoneim MM, Eissa IH, Elsehemy IA, Mostafa AE, Hegazy MM, Afifi WM, Dou D. Traditional ancient Egyptian medicine: A review. Saudi J Biol Sci. 2021;28(10):5823-5832. doi:10.1016/j.sjbs.2021.06.044
Ali SK, Hamed AR, Soltan MM, Hegazy UM, Elgorashi EE, El-Garf IA, Hussein AA. In-vitro evaluation of selected Egyptian traditional herbal medicines for treatment of alzheimer disease. BMC Complement Altern Med. 2013;13(1):121. doi:10.1186/1472-6882-13-121
Laganà P, Anastasi G, Marano F, Piccione S, Singla RK, Dubey AK, Delia S, Coniglio MA, Facciolà A, Di Pietro A. Phenolic substances in foods: Health effects as anti-inflammatory and antimicrobial agents. J AOAC Int. 2019;102(5):1378-1387.
Dong-Chen X, Yong C, Yang X, Chen-Yu S, Li-Hua P. Signaling pathways in Parkinson’s disease: molecular mechanisms and therapeutic interventions. Signal Transduct Target Ther. 2023;8(1):73.
Din SRU, Saeed S, Khan SU, Zhong M. Bioactive Compounds (BACs): A Novel Approach to Treat and Prevent Cardiovascular Diseases. Curr Probl Cardiol. Published online 2023:101664.
Garg M, Sharma A, Bansal S, Grover R, Sharma T, Kumari S, Goyal A, Bhatia S, Vaid L, Deswal G. Role of Medicinal Plants in the Management of Inflammatory Disorders: An Overview. Recent Adv Inflamm Allergy Drug Discov. Published online 2023.
Li Y, Li S, Meng X, Gan RY, Zhang JJ, Li HB. Dietary natural products for prevention and treatment of breast cancer. Nutrients. 2017;9(7):728.
Yeung AWK, Aggarwal BB, Barreca D, Battino M, Belwal T, Horbanczuk OK, Berindan-Neagoe I, Bishayee A, Daglia M, Devkota HP. Dietary natural products and their potential to influence health and disease including animal model studies. Anim Sci Pap Reports. 2018;36(4):345-358.
Chemat F, Rombaut N, Sicaire AG, Meullemiestre A, Fabiano-Tixier AS, Abert-Vian M. Ultrasound assisted extraction of food and natural products. Mechanisms, techniques, combinations, protocols and applications. A review. Ultrason Sonochem. 2017;34:540-560.
Barba FJ, Zhu Z, Koubaa M, Sant’Ana AS, Orlien V. Green alternative methods for the extraction of antioxidant bioactive compounds from winery wastes and by-products: A review. Trends Food Sci Technol. 2016;49:96-109.
Chemat F, Abert-Vian M, Fernandez X. Microwave-assisted extraction of essential oils and aromas. Microwave-assisted Extr Bioact Compd theory Pract. Published online 2013:53-68.
Rodriguez Garcia SL, Raghavan V. Green extraction techniques from fruit and vegetable waste to obtain bioactive compounds—A review. Crit Rev Food Sci Nutr. 2022;62(23):6446-6466.
Conde-Hernández LA, Espinosa-Victoria JR, Trejo A, Guerrero-Beltrán JÁ. CO2-supercritical extraction, hydrodistillation and steam distillation of essential oil of rosemary (Rosmarinus officinalis). J Food Eng. 2017;200:81-86.
Ersoy ŞK, Tütem E, Başkan KS, Apak R. Valorization of Red Onion Peels for Quercetin Recovery Using Quercetin-Imprinted Polymer. J Chromatogr Sci. 2020;58(2):163-170.
Wan Y, Wang M, Fu Q, Wang L, Wang D, Zhang K, Xia Z, Gao D. Novel dual functional monomers based molecularly imprinted polymers for selective extraction of myricetin from herbal medicines. J Chromatogr B. 2018;1097:1-9.
Kamaruzaman S, Nasir NM, Faudzi SMM, Yahaya N, Hanapi NSM, Ibrahim WNW. Solid-phase extraction of active compounds from natural products by molecularly imprinted polymers: Synthesis and extraction parameters. Polymers (Basel). 2021;13(21):1-32. doi:10.3390/polym13213780
Ashley J, Shahbazi MA, Kant K, Chidambara VA, Wolff A, Bang DD, Sun Y. Molecularly imprinted polymers for sample preparation and biosensing in food analysis: Progress and perspectives. Biosens Bioelectron. 2017;91:606-615.
Zhao Y, Tang Y, He J, Xu Y, Gao R, Zhang J, Chong T, Wang L, Tang X. Surface imprinted polymers based on amino-hyperbranched magnetic nanoparticles for selective extraction and detection of chlorogenic acid in Honeysuckle tea. Talanta. 2018;181:271-277.
Komiyama M, Takeuchi T, Mukawa T, Asanuma H. Molecular Imprinting: From Fundamentals to Applications.; 2003.
Bart H jörg, Pilz S. Related Titles Sustainable Growth and Concepts in Biotechnology History , Science and Business A Textbook for Engineers , Green Chemistry in the Pharmaceutical Industry.
Zhang QW, Lin LG, Ye WC. Techniques for extraction and isolation of natural products: A comprehensive review. Chin Med. 2018;13:1-26.
Kasprowiak A, Cazier-Dennin F, Danjou PE. Flash Chromatography System: A Practical Tool for Demonstrating the Influence of Column Characteristics on Chromatographic Resolution. J Chem Educ. 2020;97(4):1145-1150.
Gonçalves L, Cravo S, Fernandes C, Tiritan ME. Development and evaluation of Pirkle-type chiral stationary phase for flash chromatography. J Chromatogr A. 2022;1675. doi:10.1016/j.chroma.2022.463156
Tao J, Yan R, Zhao L, Wang D, Xu X. Separation and purification of two taxanes and one xylosyl-containing taxane from Taxus wallichiana Zucc.: A comparison between high-speed countercurrent chromatography and reversed-phase flash chromatography. J
Sep Sci. 2017;40(6):1273-1282. doi:10.1002/jssc.201601066
Sieniawska E, Skalicka-Woźniak K. Isolation of chlorogenic acid from Mutellina purpurea L. herb using high-performance counter-current chromatography. Nat Prod Res. 2014;28(21):1936-1939. doi:10.1080/14786419.2014.955494
Ma X, Lin H, He Y, She Y, Wang M, Abd El-Aty AM, Afifi NA, Han J, Zhou X, Wang J, Zhang J. Magnetic molecularly imprinted polymers doped with graphene oxide for the selective recognition and extraction of four flavonoids from Rhododendron species. J Chromatogr A. 2019;1598:39-48. doi:10.1016/j.chroma.2019.03.053
Li W, Jiang ZF, Tan L, Wang SX, Wang CZ, Zhang JW, Zhou L Di, Zhang QH, Yuan CS. Rapid measurements of curcumin from complex samples coupled with magnetic biocompatibility molecularly imprinted polymer using electrochemical detection. J Sep Sci. 2020;43(6):1173-1182. doi:10.1002/jssc.201900884
Camel V. Solid phase extraction of trace elements. Spectrochim Acta - Part B At Spectrosc. 2003;58(7):1177-1233. doi:10.1016/S0584-8547(03)00072-7
Zwir-Ferenc A, Biziuk M. Solid phase extraction technique - Trends, opportunities and applications. Polish J Environ Stud. 2006;15(5):677-690.
Qiao F, Sun H, Yan H, Row KH. Molecularly imprinted polymers for solid phase extraction. Chromatographia. 2006;64(11-12):625-634. doi:10.1365/s10337-006-0097-2
Jiao P, Li B, Zhang F, Tang C. Chitosan-based matrix solid-phase dispersion extraction assisted cell membrane magnetic bead ligand-affinity assay for screening active compounds from Fructus Cnidii. J Sep Sci. 2022;45(19):3725-3734. doi:10.1002/jssc.202200286
Hussain S, Schönbichler SA, Güzel Y, Sonderegger H, Abel G, Rainer M, Huck CW, Bonn GK. Solid-phase extraction of galloyl- and caffeoylquinic acids from natural sources (Galphimia glauca and Arnicae flos) using pure zirconium silicate and bismuth citrate powders as sorbents inside micro spin columns. J Pharm Biomed Anal. 2013;84:148-158. doi:10.1016/j.jpba.2013.05.029
Jiang Z fei, Zhou L di, Tan L, Wang S xian, Wang C zhi, Zhang J wei. SEPARATION. 2020;43(6). doi:10.1002/jssc.201900884
Zuo J, Ma P, Li Z, Zhang Y, Xiao D, Wu H, Dong A. Application of Molecularly Imprinted Polymers in Plant Natural Products: Current Progress and Future Perspectives. Macromol Mater Eng. 2022;2200499. doi:10.1002/mame.202200499
Chen L, Xu S, Li J. Recent advances in molecular imprinting technology: Current status, challenges and highlighted applications. Chem Soc Rev. 2011;40(5):2922-2942. doi:10.1039/c0cs00084a
Xu S, Mo R, Jin C, Cui X, Bai R, Ji Y. Mesoporous silica nanoparticles incorporated hybrid monolithic stationary phase immobilized with pepsin for enantioseparation by capillary electrochromatography. J Pharm Biomed Anal. 2017;140:190-198. doi:10.1016/j.jpba.2017.03.013
Marć M, Kupka T, Wieczorek PP, Namieśnik J. Computational modeling of molecularly imprinted polymers as a green approach to the development of novel analytical sorbents. TrAC Trends Anal Chem. 2018;98:64-78.
Azimi A, Javanbakht M. Computational prediction and experimental selectivity coefficients for hydroxyzine and cetirizine molecularly imprinted polymer based potentiometric sensors. Anal Chim Acta. 2014;812:184-190.
Cowen T, Karim K, Piletsky S. Computational approaches in the design of synthetic receptors – A review. Anal Chim Acta. 2016;936. doi:10.1016/j.aca.2016.07.027
Abdel Ghani NT, Mohamed El Nashar R, Abdel‐Haleem FM, Madbouly A. Computational design, synthesis and application of a new selective molecularly imprinted polymer for electrochemical detection. Electroanalysis. 2016;28(7):1530-1538.
Sajini T, Mathew B. A brief overview of molecularly imprinted polymers: Highlighting computational design, nano and photo-responsive imprinting. Talanta Open. 2021;4:100072.
Saad EM, El Gohary NA, Abdel-Halim M, Handoussa H, Mohamed El Nashar R, Mizaikoff B. Molecularly imprinted polymers for selective extraction of rosmarinic acid from Rosmarinus officinalis L. Food Chem. 2021;335(June 2020). doi:10.1016/j.foodchem.2020.127644
Pardeshi S, Patrikar R, Dhodapkar R, Kumar A. Validation of computational approach to study monomer selectivity toward the template Gallic acid for rational molecularly imprinted polymer design. J Mol Model. 2012;18:4797-4810.
Wu L, Sun B, Li Y, Chang W. Study properties of molecular imprinting polymer using a computational approach. Analyst. 2003;128(7):944-949. doi:10.1039/b212731h
Zahara S, Minhas MA, Shaikh H, Ali MS, Bhanger MI, Malik MI. Molecular imprinting-based extraction of rosmarinic acid from Salvia hypoleuca extract. React Funct Polym. 2021;166(July). doi:10.1016/j.reactfunctpolym.2021.104984
Megahed SH, Abdel-Halim M, Hefnawy A, Handoussa H, Mizaikoff B, El Gohary NA. Molecularly Imprinted Solid Phase Extraction Strategy for Quinic Acid. Polymers (Basel). 2022;14(16). doi:10.3390/polym14163339
Ma X, Ji W, Chen L, Wang X, Liu J, Wang X. Molecularly imprinted polymers with synthetic dummy templates for the preparation of capsaicin and dihydrocapsaicin from chili peppers. J Sep Sci. 2015;38(1):100-107. doi:10.1002/jssc.201400911
Ji W, Zhang M, Yan H, Zhao H, Mu Y, Guo L, Wang X. Selective extraction and determination of chlorogenic acids as combined quality markers in herbal medicines using molecularly imprinted polymers based on a mimic template. Anal Bioanal Chem. 2017;409(30):7087-7096. doi:10.1007/s00216-017-0667-1
Hosny H, El Gohary N, Saad E, Handoussa H, El Nashar RM. Isolation of sinapic acid from broccoli using molecularly imprinted polymers. J Sep Sci. 2018;41(5):1164-1172.
Saad EM, Madbouly A, Ayoub N, Mohamed El Nashar R. Preparation and application of molecularly imprinted polymer for isolation of chicoric acid from Chicorium intybus L. medicinal plant. Anal Chim Acta. 2015;877. doi:10.1016/j.aca.2015.03.047
Ersoy ÅK, Tütem E, Başkan KS, Apak R. Valorization of Red Onion Peels for Quercetin Recovery Using Quercetin-Imprinted Polymer. J Chromatogr Sci. 2020;58(2):163-170. doi:10.1093/chromsci/bmz079
Alara OR, Abdurahman NH, Ukaegbu CI. Extraction of phenolic compounds: A review. Curr Res Food Sci. 2021;4(December 2020):200-214. doi:10.1016/j.crfs.2021.03.011
Beltran A, Marcé RM, Cormack PAG, Borrull F. Synthesis by precipitation polymerisation of molecularly imprinted polymer microspheres for the selective extraction of carbamazepine and oxcarbazepine from human urine. J Chromatogr A. 2009;1216(12):2248-2253.
Mostafa AM, Barton SJ, Wren SP, Barker J. Review on molecularly imprinted polymers with a focus on their application to the analysis of protein biomarkers. TrAC Trends Anal Chem. 2021;144:116431.
Criscenti G, De Maria C, Longoni A, Van Blitterswijk CA, Fernandes HAM, Vozzi G, Moroni L. Soft-molecular imprinted electrospun scaffolds to mimic specific biological tissues. Biofabrication. 2018;10(4):45005.
Huang H, Zhang C, Liu L, Wang Z. Synthesis and characterization of a novel quercetin magnetic molecularly imprinted polymer via reversible addition fragmentation chain transfer strategy. J Macromol Sci Part A Pure Appl Chem. 2017;54(7):446-451. doi:10.1080/10601325.2017.1320748
Ma X, Zhang X, Lin H, Abd El-Aty AM, Rabah T, Liu X, Yu Z, Yong Y, Ju X, She Y. Magnetic molecularly imprinted specific solid-phase extraction for determination of dihydroquercetin from Larix griffithiana using HPLC. J Sep Sci. 2020;43(12):2301-2310. doi:10.1002/jssc.201901086
Peng M, Li H, Long R, Shi S, Zhou H, Yang S. Magnetic porous molecularly imprinted polymers based on surface precipitation polymerization and mesoporous SiO2 layer as sacrificial support for efficient and selective extraction and determination of chlorogenic acid in duzhong brick tea. Molecules. 2018;23(7):1-11. doi:10.3390/molecules23071554
Ertürk G, Mattiasson B. Molecular imprinting techniques used for the preparation of biosensors. Sensors. 2017;17(2):288.
Crapnell RD, Hudson A, Foster CW, Eersels K, Grinsven B van, Cleij TJ, Banks CE, Peeters M. Recent advances in electrosynthesized molecularly imprinted polymer sensing platforms for bioanalyte detection. Sensors. 2019;19(5):1204.
Di R, Zhang Y, Wu Z, Liu W, Yang C. Foam fractionation for the recovery of proanthocyanidin from Camellia seed shells using molecular imprinting chitosan nanoparticles as collector. J Mol Liq. 2020;302. doi:10.1016/j.molliq.2020.112523
Zhang H, Zhao S, Zhang L, Han B, Yao X, Chen W, Hu Y. Preparation of ellagic acid molecularly imprinted polymeric microspheres based on distillation-precipitation polymerization for the efficient purification of a crude extract. J Sep Sci. 2016;39(16):3098-3104. doi:10.1002/jssc.201600355
Ma X, Lin H, Zhang J, Zhou X, Han J, She Y, Qiu C, He Q, Wang J, Rabah T. Preparation and characterization of dummy molecularly imprinted polymers for separation and determination of farrerol from Rhododendron aganniphum using HPLC. Green Chem Lett Rev. 2018;11(4):513-522. doi:10.1080/17518253.2018.1541481
Wang T, Li P, Sun Y, Song X, Li H, Qin L, Zhou J, Huang Q, Lei F. Camptothecin-imprinted polymer microspheres with rosin-based cross-linker for separation of camptothecin from Camptotheca acuminata fruit. Sep Purif Technol. 2020;234(February 2019). doi:10.1016/j.seppur.2019.116085
Sun Y, Zhang Y, Ju Z, Niu L, Gong Z, Xu Z. Molecularly imprinted polymers fabricated by Pickering emulsion polymerization for the selective adsorption and separation of quercetin from Spina Gleditsiae. New J Chem. 2019;43(37):14747-14755.
Zhao G, Liu J, Liu M, Han X, Peng Y, Tian X, Liu J, Zhang S. Synthesis of molecularly imprinted polymer via emulsion polymerization for application in solanesol separation. Appl Sci. 2020;10(8):2868.
Sun Y, Zhang Y, Ju Z, Niu L, Gong Z, Xu Z. Molecularly imprinted polymers fabricated by Pickering emulsion polymerization for the selective adsorption and separation of quercetin from Spina Gleditsiae. New J Chem. 2019;43(37):14747-14755. doi:10.1039/c9nj03559a
Chromatography M, Biomedicine EA. SEPARATION. 2021;44(7). doi:10.1002/jssc.202001094
Mohammadinejad A, Kamrani Rad SZ, Karimi G, Motamedshariaty VS, Mohajeri SA. Preparation, evaluation, and application of dummy molecularly imprinted polymer for analysis of hesperidin in lime juice. J Sep Sci. 2021;44(7):1490-1500. doi:10.1002/jssc.202001094
Alipour S, Azar PA, Husain SW, Rajabi HR. Determination of Rosmarinic acid in plant extracts using a modified sensor based on magnetic imprinted polymeric nanostructures. Sensors Actuators, B Chem. 2020;323(April):128668. doi:10.1016/j.snb.2020.128668
Wu Q, Naeem A, Zou J, Yu C, Wang Y, Chen J, Ping Y. Isolation of Phenolic Compounds from Raspberry Based on Molecular Imprinting Techniques and Investigation of Their Anti-Alzheimer ’ s Disease Properties. Published online 2022.
SHENG JY, WANG SQ, LIU KH, ZHU B, ZHANG QY, QIN LP, WU JJ. Rubus chingii Hu: an overview of botany, traditional uses, phytochemistry, and pharmacology. Chin J Nat Med. 2020;18(6):401-416. doi:10.1016/S1875-5364(20)30048-0
Cao J, Shen C, Wang X, Zhu Y, Bao S, Wu X, Fu Y. A porous cellulose-based molecular imprinted polymer for specific recognition and enrichment of resveratrol. Carbohydr Polym. 2021;251:117026.
Risuleo G, La Mesa C. Resveratrol: biological activities and potential use in health and disease. Nutraceuticals Vet Med. Published online 2019:215-226.
Anfossi L, Giovannoli C, Di Nardo F, Cavalera S, Chiarello M, Trotta F, Baggiani C. Selective enrichment of ailanthone from leaves of ailanthus altissima by tandem reverse phase/molecularly imprinted solid phase extraction. Microchem J. 2020;158(April):105198. doi:10.1016/j.microc.2020.105198
Azimi M, Ahmadi Golsefidi M, Varasteh Moradi A, Ebadi M, Zafar Mehrabian R. Separation and Purification of Effective Ingredient of Galegine from Galega officinalis L. by Column Chromatography Tandemed with Molecularly Imprinted Polymer Enforced by Graphene Oxide (GO-MIP) Technique. J Med plants By-product. Published online 2020.
Ji W, Wang T, Liu W, Liu F, Guo L, Geng Y, Wang X. Water-compatible micron-sized monodisperse molecularly imprinted beads for selective extraction of five iridoid glycosides from Cornus officinalis fructus. J Chromatogr A. 2017;1504:1-8. doi:10.1016/j.chroma.2017.05.003
Li L, Li L, Cheng G, Wei S, Wang Y, Huang Q, Wu W, Liu X, Chen G. Study of the Preparation and Properties of Chrysin Binary Functional Monomer Molecularly Imprinted Polymers. Polymers (Basel). 2022;14(14):1-16. doi:10.3390/polym14142771
Wang Y, Li L, Cheng G, Li L, Liu X, Huang Q. Preparation and Recognition Properties of Molecularly Imprinted Nanofiber Membrane of Chrysin. Polymers (Basel). 2022;14(12). doi:10.3390/polym14122398
Zhong X, Liu D, Jiang Z, Li C, Chen L, Xia Y, Liu D, Yao Q, Wang D. Chrysin induced cell apoptosis and inhibited invasion through regulation of TET1 expression in gastric cancer cells. Onco Targets Ther. 2020;13:3277-3287. doi:10.2147/OTT.S246031
Wang J, Wang H, Sun K, Wang X, Pan H, Zhu J, Ji X, Li X. Chrysin suppresses proliferation, migration, and invasion in glioblastoma cell lines via mediating the ERK/Nrf2 signaling pathway. Drug Des Devel Ther. 2018;12:721-733. doi:10.2147/DDDT.S160020
Płotka-Wasylka J, Szczepańska N, de la Guardia M, Namieśnik J. Modern trends in solid phase extraction: New sorbent media. TrAC - Trends Anal Chem. 2016;77:23-43. doi:10.1016/j.trac.2015.10.010
Hosny H, El Gohary N, Saad E, Handoussa H, El Nashar RM. Isolation of sinapic acid from broccoli using molecularly imprinted polymers. J Sep Sci. 2018;41(5). doi:10.1002/jssc.201701120
Badawy MEI, El-Nouby MAM, Kimani PK, Lim LW, Rabea EI. A Review of the Modern Principles and Applications of Solid-Phase Extraction Techniques in Chromatographic Analysis. Vol 38. Springer Nature Singapore; 2022. doi:10.1007/s44211-022-00190-8
Saad EM, Madbouly A, Ayoub N, El Nashar RM. Preparation and application of molecularly imprinted polymer for isolation of chicoric acid from Chicorium intybus L. medicinal plant. Anal Chim Acta. 2015;877:80-89.
Hefnawy M, El-Gendy M, Al-Salem H, Marenga H, El-Azab A, Abdel-Aziz A, El Gamal A, Alanazi M, Obaidullah A, Al-Hossaini A. Trends in monoliths: Packings, stationary phases and nanoparticles. J Chromatogr A. Published online 2023:463819.
Piacham T, Isarankura-Na-Ayudhya C, Prachayasittikul V. Quercetin-imprinted polymer for anthocyanin extraction from mangosteen pericarp. Mater Sci Eng C Mater Biol Appl. 2015;51:127-131. doi:10.1016/j.msec.2015.02.051
Long J, Liang B, Li S, Chen zhenbin. Preparation and characterization of a novel molecularly imprinted polymer for the separation of glycyrrhizic acid. J Sep Sci. 2017;40(24):4847-4856. doi:10.1002/jssc.201700791
Eidi S, Iranshahi M, Mohammadinejad A, Mohsenzadeh MS, Farhadi F, Mohajeri SA. Selective isolation of sesquiterpene coumarins from asafoetida using dummy molecularly imprinted solid phase extraction method. J Chromatogr B Anal Technol Biomed Life Sci. 2020;1138(May 2019):121943. doi:10.1016/j.jchromb.2019.121943
Ariani MD, Zuhrotun A, Manesiotis P, Hasanah AN. Magnetic Molecularly Imprinted Polymers: An Update on Their Use in the Separation of Active Compounds from Natural Products. Polymers (Basel). 2022;14(7). doi:10.3390/polym14071389
Regal P, Díaz-Bao M, Barreiro R, Fente C, Cepeda A. Design of a molecularly imprinted stir-bar for isolation of patulin in apple and LC-MS/MS detection. Separations. 2017;4(2). doi:10.3390/separations4020011
Sun GY, Wang C, Luo YQ, Zhao YX, Yang J, Liu ZS, Aisa HA. Cost-effective imprinting combining macromolecular crowding and a dummy template for the fast purification of punicalagin from pomegranate husk extract. J Sep Sci. 2016;39(10):1963-1970. doi:10.1002/jssc.201600165
Ma W, Tang B, Row KH. Exploration of a ternary deep eutectic solvent of methyltriphenylphosphonium bromide/chalcone/formic acid for the selective recognition of rutin and quercetin in Herba Artemisiae Scopariae. J Sep Sci. 2017;40(16):3248-3256.
Yu H, He Y, She Y, Wang M, Yan Z, Ren JH, Cao Z, Shao Y, Wang S, Abd El-Aty AM, Hacımüftüoğlu A, Wang J. Preparation of molecularly imprinted polymers coupled with high-performance liquid chromatography for the selective extraction of salidroside from Rhodiola crenulata. J Chromatogr B, Anal Technol Biomed life Sci. 2019;1118-1119:180-186. doi:10.1016/j.jchromb.2019.04.004
Lv Y, Qu Q, Li C, Zhu T. Acrylamide-modified 3-aminopropyltriethoxysilanes hybrid monomer for highly selective imprinting recognition of theophylline. J Chromatogr Sci. 2020;58(1):75-82. doi:10.1093/chromsci/bmz106
Zhao QY, Zhao HT, Yang X, Zhang H, Dong AJ, Wang J, Li B. Selective recognition and fast enrichment of anthocyanins by dummy molecularly imprinted magnetic nanoparticles. J Chromatogr A. 2018;1572:9-19. doi:10.1016/j.chroma.2018.08.029
Ma W, Row KH. Solid-Phase Extraction of Catechins from Green Tea with Deep Eutectic Solvent Immobilized Magnetic Molybdenum Disulfide Molecularly Imprinted Polymer. Molecules. 2020;25(2). doi:10.3390/molecules25020280
Shi S, Fan D, Xiang H, Li H. Effective synthesis of magnetic porous molecularly imprinted polymers for efficient and selective extraction of cinnamic acid from apple juices. Food Chem. 2017;237:198-204. doi:10.1016/j.foodchem.2017.05.086
Li G, Wang X, Row KH. Magnetic molecularly imprinted polymers based on silica modified by deep eutectic solvents for the rapid simultaneous magnetic-based solid-phase extraction of Salvia miltiorrhiza bunge, Glycine max (Linn.) Merr and green tea. Electrophoresis. 2018;39(8):1111-1118. doi:10.1002/elps.201700474
Zhang J, Li B, Yue H, Wang J, Zheng Y. Highly selective and efficient imprinted polymers based on carboxyl-functionalized magnetic nanoparticles for the extraction of gallic acid from pomegranate rind. J Sep Sci. 2018;41(2):540-547. doi:10.1002/jssc.201700822
Wang DD, Gao D, Xu WJ, Li F, Yin MN, Fu QF, Xia ZN. Magnetic molecularly imprinted polymer for the selective extraction of hesperetin from the dried pericarp of Citrus reticulata Blanco. Talanta. 2018;184:307-315. doi:10.1016/j.talanta.2018.03.010
Cheng Y, Nie J, Liu H, Kuang L, Xu G. Synthesis and characterization of magnetic molecularly imprinted polymers for effective extraction and determination of kaempferol from apple samples. J Chromatogr A. 2020;1630:461531. doi:10.1016/j.chroma.2020.461531
Guo B, Tong Y, Zhang B, Tian M. Double affinity based molecularly imprinted polymers for selective extraction of luteolin: A combination of synergistic metal chelating and boronate affinity. Microchem J. 2021;160(PB):105670. doi:10.1016/j.microc.2020.105670
He G, Tang Y, Hao Y, Shi J, Gao R. Preparation and application of magnetic molecularly imprinted nanoparticles for the selective extraction of osthole in Libanotis Buchtomensis herbal extract. J Sep Sci. 2016;39(12):2313-2320. doi:10.1002/jssc.201600266
Cao J, Shen C, Wang X, Zhu Y, Bao S, Wu X, Fu Y. A porous cellulose-based molecular imprinted polymer for specific recognition and enrichment of resveratrol. Carbohydr Polym. 2021;251(August 2020). doi:10.1016/j.carbpol.2020.117026
Chen Z, Liu H, Chen J, Zhu W, Liu Y, Min J, Chen X, Li B, Yang X. Separation and enrichment of sibiskoside from Sibiraea angustat with magnetic surface dummy template molecularly imprinted polymers. J Chromatogr B, Anal Technol Biomed life Sci. 2021;1178:122767. doi:10.1016/j.jchromb.2021.122767