Research Progress of Magnetic Molecularly Imprinted Polymers in Separation and Purification of Natural Active Substances

WANG Yanhui; ZHENG Guangyao; YAN Linlin

doi:10.13386/j.issn1002-0306.2022070368

Volume 44 Issue 11

May 2023

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Science and Technology of Food Industry > 2023 > 44(11): 442-450. > DOI: 10.13386/j.issn1002-0306.2022070368

WANG Yanhui, ZHENG Guangyao, YAN Linlin. Research Progress of Magnetic Molecularly Imprinted Polymers in Separation and Purification of Natural Active Substances[J]. Science and Technology of Food Industry, 2023, 44(11): 442−450. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022070368.

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Research Progress of Magnetic Molecularly Imprinted Polymers in Separation and Purification of Natural Active Substances

Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; Key Lab. of Biomass Energy and Material, Jiangsu Province; Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing 210042, China

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Received Date: August 01, 2022
Available Online: March 24, 2023

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Abstract

Abstract

Magnetic molecularly imprinted polymers are novel separation materials assembled by magnetic nanoparticles and molecularly imprinted polymers, with specific selectivity, easy separation and regeneration, which can be used in the preliminary treatment of food and drugs, and the separation and purification of natural active substances. Herein, the preparation principle and method of magnetic molecular imprinting technology are elucidated, and the research progress (2017~2022) of magnetic molecular imprinting polymers in the separation and purification of natural active substances, such as polyphenols, alkaloids, organic acids, terpenoids, and macromolecules are reviewed. Meanwhile, the difficulties in the field of separation and purification are discussed. This review will provide reference for the enrichment, purification, analysis and detection of natural active substances.
- magnetic,
- molecular imprinted polymers,
- separation and purification,
- natural active substances

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[1]	周佳儒, 李久明, 徐宁, 等. 天然植物中有效成分的提取、分离技术研究进展[J]. 内蒙古民族大学学报(自然科学版),2018,33(1):14−18. [ZHOU J R, LI J M, XU N, et al. Progress in extraction and separation of effective components from natural plants[J]. Journal of Inner Mongolia Minzu University (Natural Sciences),2018,33(1):14−18.
[2]	刘春秀. 植物活性成分的提取技术研究进展[J]. 安徽农业科学,2011,39(3):1273−1274, 1277. [LIU C X. Research progress on extracting methods of effective constituent from plants[J]. Journal of Anhui Agricultural Sciences,2011,39(3):1273−1274, 1277. doi: 10.3969/j.issn.0517-6611.2011.03.007
[3]	王聪慧, 任娜, 魏微, 等. 天然产物分离纯化新技术[J]. 应用化工,2019,48(8):1940−1943. [WANG C H, REN N, WEI W, et al. New technology for separation and purification of natural products[J]. Applied Chemical Industry,2019,48(8):1940−1943. doi: 10.3969/j.issn.1671-3206.2019.08.039
[4]	杨敏, 张天锡, 史磊, 等. 大孔吸附树脂分离纯化中药成分影响因素探讨[J]. 中草药,2020,51(15):4050−4058. [YANG M, ZHANG T C, SHI L, et al. Review on factors influencing separation and purification of Chinese materia medica components by microporous adsorption resin[J]. Chinese Traditional and Herbal Drugs,2020,51(15):4050−4058.
[5]	张志宏, 邢娜, 彭东辉, 等. 黄瓜子多糖的分离、纯化和体外抗氧化活性研究[J]. 中国药房,2021,32(4):432−438. [ZHANG Z H, XING N, PENG D H, et al. Study on isolation, purification and in vitro antioxidant activity of the polysaccharides from Cucumis satiuus[J]. China Pharmacy,2021,32(4):432−438.
[6]	邓利, 孙猛, 谭天伟, 等. β-环糊精键合固定相分离纯化银杏叶提取物和银杏黄酮[J]. 中草药,2004,35(10):1105−1109. [DENG L, SUN M, TAN T W, et al. Purification of Ginkgo biloba leaf extract and flavone on β-cyclodextrin-Superose 12 pg[J]. Chinese Traditional and Herbal Drugs,2004,35(10):1105−1109.
[7]	孙一焱, 王菲, 臧彩娟, 等. 聚酰胺分离纯化金花葵花总黄酮的工艺研究[J]. 辽宁石油化工大学学报,2019,39(1):15−18. [SUN Y Y, WANG F, ZANG C J, et al. Separation and purification of total flavonoids from Flos Lonicerae by polyamide[J]. Journal of Liaoning Petrochemical University,2019,39(1):15−18.
[8]	许苗苗, 王素素, 李辉, 等. 沉淀聚合法制备葛根素印迹微球及其固相萃取葛根粉[J]. 食品科学,2015(10):11−15. [XU M M, WANG S S, LI H, et al. Reparation of puerarin-imprinted polymer microspheres by precipitation polymerization technique for use in solid phase extraction of flavonoids from Pueraria root powder[J]. Food Science,2015(10):11−15.
[9]	李秀凉, 杨涵冰, 吕莹, 等. 杏鲍菇多糖组分的分离纯化及结构鉴定[J]. 食品安全质量检测学报,2022,13(7):2097−2104. [LI X L, YANG H B, LÜ Y, et al. Isolation, purification and structural identification of Pleurotus eryngii polysaccharides[J]. Journal of Food Safety & Quality,2022,13(7):2097−2104.
[10]	刘克建, 屈琦超. 分子印迹技术在天然活性成分分离纯化中的研究进展[J]. 食品工业科技,2018,39(22):328−333, 340. [LIU K J, QU Q C. Research progress of separation and purification of the active ingredient of natural products based on molecular imprinted technology[J]. Science and Technology of Food Industry,2018,39(22):328−333, 340.
[11]	KASIRI E, HADDADI H, JAVADIAN H, et al. Highly effective pre-concentration of thymol and carvacrol using nano-sized magnetic molecularly imprinted polymer based on experimental design optimization and their trace determination in summer savoury, Origanum majorana and Origanum vulgare extracts[J]. Journal of Chromatography B,2021,1182:122941. doi: 10.1016/j.jchromb.2021.122941
[12]	曹玉天, 盛万里, 齐小花, 等. 聚乙二醇修饰的槲皮素磁性分子印迹聚合物合成及其应用[J]. 分析科学学报,2021,37(6):719−725. [CAO Y T, SHENG W L, QI X H, et al. Synthesis and application of magnetic molecularly imprinted polymers od PEG modified quercetin[J]. Journal of Analytical Science,2021,37(6):719−725.
[13]	周晏曲, 方诗佩, 江如蓝, 等. 穿心莲内酯磁性分子印迹聚合物的制备及吸附性能考察[J]. 华西药学杂志,2022,37(2):126−129. [ZHOU Y Q, FANG S P, JIANG R L, et al. Preparation of andrographolide magnetic molecularly imprinted polymer and investigation of its absorption properties[J]. West China Journal of Pharmaceutical Sciences,2022,37(2):126−129.
[14]	MIRZAPOUR F, SADEGHI M. Magnetic molecular imprinted polymers for in vitro controlled release and solid-phase extraction of dextromethorphan: Synthesize, characterization, and application[J]. Iranian Polymer Journal,2022,31(5):553−571. doi: 10.1007/s13726-021-01003-x
[15]	GUO T, WANG C, ZHOU H, et al. A multifunctional near-infrared fluorescent sensing material based on core-shell upconversion nanoparticles @ magnetic nanoparticles and molecularly imprinted polymers for detection of deltamethrin[J]. Microchimica Acta,2021,188(5):1−8.
[16]	马洁, 黄静, 曾延波, 等. 苏丹红 Ⅰ 磁性分子印迹聚合物的制备及其分离分析应用[J]. 分析测试学报,2013,32(6):726−731. [MA J, HUANG J, ZENG Y B, et al. Preparation of a kind of magnetic molecularly imprinted polymer toward Sudan I and its application in separation of Sudan I[J]. Journal of Instrumental Analysis,2013,32(6):726−731.
[17]	孙治安, 祁玉霞, 王霞, 等. 三聚氰胺磁性表面分子印迹聚合物的制备及其在牛奶样品中的应用[J]. 色谱,2018,36(8):716. [SUN Z A, QI Y X, WANG X, et al. Preparation of magnetic surface molecularly imprinted polymers for melamine and its application in milk samples[J]. Chinese Journal of Chromatography,2018,36(8):716. doi: 10.3724/SP.J.1123.2018.03033
[18]	李随心, 霍云雷, 吴云鹏, 等. 亲水性丁香菌酯分子印迹微球的制备、表征与吸附性能的研究[J]. 食品工业科技,2021,42(5):72−77, 92. [LI S X, HUO Y L, WU Y P, et al. Preparation, characterization and absorption properties of hydrophilic syringostrobin molecularly imprinted microspheres[J]. Science and Technology of Food Industry,2021,42(5):72−77, 92.
[19]	彭胜, 李奂, 施树云. 绿原酸亲水性磁性分子印迹树脂的合成及其固相萃取性能评价[J]. 色谱,2019,37(3):293−298. [PENG S, LI H, SHI S Y. Preparation of hydrophilic, magnetic molecularly imprinted resins of chlorogenic acid and evaluation of its solid-phase extraction performance[J]. Chinese Journal of Chromatography,2019,37(3):293−298. doi: 10.3724/SP.J.1123.2018.11026
[20]	张明明. 亲水印迹材料的制备及对天麻素和环烯醚萜苷的识别研究[D]. 济南: 山东师范大学, 2017 ZHANG M M. Hydrophilic molecularly imprinted polymers for the recognition of gastrodin and iridoid glycosides[D]. Jinan: Shandong Normal University, 2017.
[21]	ANSELL R J, MOSBACH K. Magnetic molecularly imprinted polymer beads for drug radioligand binding assay[J]. Analyst,1998,123(7):1611−1616. doi: 10.1039/a801903g
[22]	李凯, 孙蕊, 彭羽, 等. Fe₃O₄ 磁性分子印迹聚合物的研究进展[J]. 化学研究与应用,2015,27(12):1790−1795. [LI K, SUN R, PENG Y, et al. Research progress of Fe₃O₄ magnetic molecularly imprinted polymers[J]. Chemical Research and Application,2015,27(12):1790−1795.
[23]	CARUSO F. Nanoengineering of particle surfaces[J]. Advanced Materials,2001,13(1):11−22. doi: 10.1002/1521-4095(200101)13:1<11::AID-ADMA11>3.0.CO;2-N
[24]	陈振羽, 郭亚甜, 张仪恒, 等. 磁性分子印迹技术在药物分析学创新实验中的应用[J]. 广州化工,2022,50(14):189−192, 203. [CHEN Z Y, GUO Y T, ZHANG Y H, et al. Application of magnetic molecular imprinting technique in innovative experiments of pharmaceutical analysis[J]. Guangzhou Chemical Industry,2022,50(14):189−192, 203.
[25]	邓芳, 李越湘, 罗旭彪, 等. 磁性分子印迹聚合物的制备与研究进展[J]. 高分子材料科学与工程,2011,27(4):171−174. [DENG F, LI Y X, LUO X B, et al. Preparation and research progress of magnetic molecularly imprinted polymer[J]. Polymer Materials Science & Engineering,2011,27(4):171−174.
[26]	CHENG Y, NIE J, LIU H, et al. Synthesis and characterization of magnetic molecularly imprinted polymers for effective extraction and determination of kaempferol from apple samples[J]. Journal of Chromatography A,2020,1630:461531. doi: 10.1016/j.chroma.2020.461531
[27]	CHENG Y, NIE J, LI J, et al. Synthesis and characterization of core–shell magnetic molecularly imprinted polymers for selective recognition and determination of quercetin in apple samples[J]. Food Chemistry,2019,287:100−106. doi: 10.1016/j.foodchem.2019.02.069
[28]	CHEN F F, XIE X Y, SHI Y P. Preparation of magnetic molecularly imprinted polymer for selective recognition of resveratrol in wine[J]. Journal of Chromatography A,2013,1300:112−118. doi: 10.1016/j.chroma.2013.02.018
[29]	DUAN F, CHEN C, ZHAO X, et al. Water-compatible surface molecularly imprinted polymers with synergy of bi-functional monomers for enhanced selective adsorption of bisphenol A from aqueous solution[J]. Environmental Science: Nano,2016,3(1):213−222. doi: 10.1039/C5EN00198F
[30]	HUANG J, TONG J, LUO J, et al. Green synthesis of water-compatible fluorescent molecularly imprinted polymeric nanoparticles for efficient detection of paracetamol[J]. ACS Sustainable Chemistry & Engineering,2018,6(8):9760−9770.
[31]	LI H, LONG R, TONG C, et al. Shell thickness controlled hydrophilic magnetic molecularly imprinted resins for high-efficient extraction of benzoic acids in aqueous samples[J]. Talanta,2019,194:969−976. doi: 10.1016/j.talanta.2018.10.099
[32]	胡颖. 磁性分子印迹材料的应用研究进展[J]. 浙江化工,2015,46(12):12−17. [HU Y. Advance in application of magnetic molecularly imprinted materials[J]. Zhejiang Chemical Industry,2015,46(12):12−17. doi: 10.3969/j.issn.1006-4184.2015.12.004
[33]	陆彦蓉, 杨娅林, 殷晓阳, 等. 磁性纳米材料在兽药残留检测应用中的研究进展[J]. 中国兽药杂志,2022,56(2):88−93. [LU Y R, YANG Y L, YIN X Y, et al. Research progress of magnetic nanomaterials in veterinary drug residue detection[J]. Chinese Journal of Veterinary Drug,2022,56(2):88−93.
[34]	杨卫海, 吴瑶, 张轶, 等. 磁性分子印迹聚合物核壳微球的制备及应用[J]. 化学进展,2010,22(9):1819−1825. [YANG W H, WU Y, ZHANG Y, et al. Preparation and application of core-shell magnetic molecularly imprinted polymer microspheres[J]. Progress in Chemistry,2010,22(9):1819−1825.
[35]	黄莹. 溶剂热法制备高比表面积氮化碳及其对盐酸四环素的光降解性能研究[D]. 南宁: 广西大学, 2021 HUANG Y. Preparation of carbon nitride with high specific surface area bu solvothermal method and study on the photodegradation of tetracycline hydrochloride[D]. Nanning: Guangxi University, 2021.
[36]	刘锋. 微乳法合成二氧化钛及其光催化去除一氧化氮性能研究[D]. 武汉: 华中师范大学, 2019 LIU F. Titanium dioxide prepared by microemulsion method and its photocatalytic removal of NO[D]. Wuhan: Central China Normal University, 2019.
[37]	DODI G, HRITCU D, DRAGANESCU D, et al. Iron oxide nanoparticles for magnetically assisted patterned coatings[J]. Journal of Magnetism and Magnetic Materials,2015,388:49−58. doi: 10.1016/j.jmmm.2015.04.011
[38]	SU X, LI X, LI J, et al. Synthesis and characterization of core–shell magnetic molecularly imprinted polymers for solid-phase extraction and determination of Rhodamine B in food[J]. Food Chemistry,2015,171:292−297. doi: 10.1016/j.foodchem.2014.09.024
[39]	FAROOQ S, NIE J, CHENG Y, et al. Synthesis of core-shell magnetic molecularly imprinted polymer for the selective determination of imidacloprid in apple samples[J]. Journal of Separation Science,2019,42(14):2455−2465. doi: 10.1002/jssc.201900221
[40]	WANG D D, GAO D, XU W J, et al. Magnetic molecularly imprinted polymer for the selective extraction of hesperetin from the dried pericarp of Citrus reticulata Blanco[J]. Talanta,2018,184:307−315. doi: 10.1016/j.talanta.2018.03.010
[41]	彭飞. 核壳型磁性分子印迹聚合物的制备表征及其对两种抗生素的吸附性能研究[D]. 乌鲁木齐: 新疆师范大学, 2022 PENG F. Preparation characterization of core shell magnetic molecularly imprinted polymers and their adsorption properties toward two antibiotics[D]. Wulumuqi: Xinjiang Normal University, 2022.
[42]	孙涛, 李媛媛, 张华承, 等. 基于环糊精的分子印迹技术[J]. 化学进展,2010,22(5):888. [SU T, LI Y Y, ZHANG H C, et al. Molecular imprinting technology based on cyclodextrins[J]. Progress in Chemistry,2010,22(5):888.
[43]	OLWILL A, HUGHES H, O’RIORDAIN M, et al. The use of molecularly imprinted sol-gels in pharmaceutical separations[J]. Biosensors and Bioelectronics,2004,20(6):1045−1050. doi: 10.1016/j.bios.2004.04.029
[44]	YANG D H, JU M J, MAEDA A, et al. Design of highly efficient receptor sites by combination of cyclodextrin units and molecular cavity in TiO₂ ultrathin layer[J]. Biosensors and Bioelectronics,2006,22(3):388−392. doi: 10.1016/j.bios.2006.06.013
[45]	SUN H W, QIAO F X. Recognition mechanism of water-compatible molecularly imprinted solid-phase extraction and determination of nine quinolones in urine by high performance liquid chromatography[J]. Journal of Chromatography A,2008,1212(1−2):1−9. doi: 10.1016/j.chroma.2008.09.107
[46]	YAN H, QIAO F, ROW K H. Molecularly imprinted-matrix solid-phase dispersion for selective extraction of five fluoroquinolones in eggs and tissue[J]. Analytical Chemistry,2007,79(21):8242−8248. doi: 10.1021/ac070644q
[47]	GAO B, WANG J, YANG Y. Studies of imprinting conditions and application performance of pirimicarb molecule-imprinted material prepared using a novel surface-imprinting technique[J]. Chromatographia,2009,69(11):1353−1361.
[48]	陈志萍, 高保娇, 杨晓峰, 等. 表面印迹法制备胆红素分子印迹材料及其识别性能[J]. 过程工程学报,2009,9(2):387−392. [CHEN Z P, GAO B J, YANG X F, et al. Preparation of molecular surface imprinting material and its identification properties for bilirubin[J]. The Chinese Journal of Process Engineering,2009,9(2):387−392. doi: 10.3321/j.issn:1009-606X.2009.02.032
[49]	LI Y, YANG H H, YOU Q H, et al. Protein recognition via surface molecularly imprinted polymer nanowires[J]. Analytical Chemistry,2006,78(1):317−320. doi: 10.1021/ac050802i
[50]	TIAN X, SONG H, WANG Y, et al. Hydrophilic magnetic molecularly imprinted nanobeads for efficient enrichment and high performance liquid chromatographic detection of 17beta-estradiol in environmental water samples[J]. Talanta,2020,220:121367. doi: 10.1016/j.talanta.2020.121367
[51]	ZHOU T, WANG Y, LI T, et al. Fabricating magnetic hydrophilic molecularly imprinted resin with enhanced adsorption and recognition performance for targeted detecting chlorophenols in environmental water[J]. Chemical Engineering Journal,2021,420:129904. doi: 10.1016/j.cej.2021.129904
[52]	YE L. Synthetic strategies in molecular imprinting[J]. Molecularly Imprinted Polymers in Biotechnology,2015,150:1−24.
[53]	HUANG C, WANG H, MA S, et al. Recent application of molecular imprinting technique in food safety[J]. Journal of Chromatography A,2021,1657:462579. doi: 10.1016/j.chroma.2021.462579
[54]	WANG Z, ZHANG Z, YAN R, et al. Facile fabrication of snowman-like magnetic molecularly imprinted polymer microspheres for bisphenol A via one-step Pickering emulsion polymerization[J]. Reactive and Functional Polymers,2021,164:104911. doi: 10.1016/j.reactfunctpolym.2021.104911
[55]	PAN J, ZHU W, DAI X, et al. Magnetic molecularly imprinted microcapsules derived from Pickering emulsion polymerization and their novel adsorption characteristics for λ-cyhalothrin[J]. RSC Advances,2014,4(9):4435−4443. doi: 10.1039/C3RA43178A
[56]	LI G, ZHA J, NIU M, et al. Bifunctional monomer molecularly imprinted sol-gel polymers based on the surface of magnetic halloysite nanotubes as an effective extraction approach for norfloxacin[J]. Applied Clay Science,2018,162:409−417. doi: 10.1016/j.clay.2018.06.003
[57]	WANG B, DUAN A, XIE S, et al. The molecular imprinting of magnetic nanoparticles with boric acid affinity for the selective recognition and isolation of glycoproteins[J]. RSC Advances,2021,11(41):25524−25529. doi: 10.1039/D1RA00716E
[58]	WEI Q, CAO F, ZHANG Y, et al. Preparation of surface molecularly imprinted poly (dopamine) film for 4-hydroxybenzoic acid (4-BA) recognition by one-step method[J]. Analytical Letters,2011,44(10):1796−1806. doi: 10.1080/00032719.2010.526270
[59]	LI H, JIANG B, LI J. Recent advances in dopamine-based materials constructed via one-pot co-assembly strategy[J]. Advances in Colloid and Interface Science,2021,295:102489. doi: 10.1016/j.cis.2021.102489
[60]	LI X, PAN J, DAI J, et al. Surface molecular imprinting onto magnetic yeast composites via atom transfer radical polymerization for selective recognition of cefalexin[J]. Chemical Engineering Journal,2012,198:503−511.
[61]	KONG X J, ZHENG C, LAN Y H, et al. Synthesis of multirecognition magnetic molecularly imprinted polymer by atom transfer radical polymerization and its application in magnetic solid-phase extraction[J]. Analytical and Bioanalytical Chemistry,2018,410(1):247−257. doi: 10.1007/s00216-017-0716-9
[62]	LI Y, LI X, CHU J, et al. Synthesis of core-shell magnetic molecular imprinted polymer by the surface RAFT polymerization for the fast and selective removal of endocrine disrupting chemicals from aqueous solutions[J]. Environmental Pollution,2010,158(6):2317−2323. doi: 10.1016/j.envpol.2010.02.007
[63]	刘昕皓, 魏粉菊, 王学顺, 等. 多酚类化合物的生物活性研究进展[J]. 中国医药工业杂志,2021,52(4):471−483. [LIU X H, WEI F J, WANG X S, et al. Progress on biological activities of polyphenol[J]. Chinese Journal of Pharmaceuticals,2021,52(4):471−483.
[64]	刘军, 任汝全, 张燕如, 等. 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(7):3365−3376. [LIU J, REN R Q, ZHANG Y R, et al. Progress in research and application of five kinds of flavonoids molecular imprinting separation technique[J]. Chemical Industry and Engineering Progress,2019,38(7):3365−3376.
[65]	陈亮, 李医明, 陈凯先, 等. 植物多酚类成分提取分离研究进展[J]. 中草药,2013,44(11):1501−1507. [CHEN L, LI Y M, CHENG K X, et al. Research progress in extraction and isolation of plant polyphenols[J]. Chinese Traditional and Herbal Drugs,2013,44(11):1501−1507. doi: 10.7501/j.issn.0253-2670.2013.11.027
[66]	MA W, DAI Y, ROW K H. Molecular imprinted polymers based on magnetic chitosan with different deep eutectic solvent monomers for the selective separation of catechins in black tea[J]. Electrophoresis,2018,39(15):2039−2046. doi: 10.1002/elps.201800034
[67]	WANG F, NI X, ZHANG J, et al. Novel composite nanomaterials based on magnetic molecularly imprinted polymers for selective extraction and determination of rutin in fruit juice[J]. Food Chemistry,2022,381:132275. doi: 10.1016/j.foodchem.2022.132275
[68]	LI X, DAI Y, ROW K H. Preparation of two-dimensional magnetic molecularly imprinted polymers based on boron nitride and a deep eutectic solvent for the selective recognition of flavonoids[J]. Analyst,2019,144(5):1777−1788. doi: 10.1039/C8AN02258E
[69]	刘志刚, 郭庆功, 陈景涛. 刺山柑总生物碱干预椎间盘退变模型大鼠髓核细胞的增殖与凋亡[J]. 中国组织工程研究,2021,25(11):1699. [LIU Z G, GUO Q G, CHEN J T. Effect of Capparis spinosa total alkaloid on proliferation and apoptosis of nucleus pulposus cells in an intervertebral disc degeneration rat model[J]. Chinese Journal of Tissue Engineering Research,2021,25(11):1699.
[70]	刘文成, 李琰, 常冰. 吡咯生物碱相关肝窦阻塞综合征发病机制的研究进展[J]. 临床肝胆病杂志,2021,37(4):962−964. [LIU W C, LI Y, CHANG B. Research advances in the pathogenesis of pyrrole alkaloid-associated hepatic sinus obstruction syndrome[J]. Journal of Clinical Hepatology,2021,37(4):962−964.
[71]	周贤春, 何春霞, 苏力坦, 等. 生物碱的研究进展[J]. 生物技术通讯,2006,17(3):476−479. [ZHOU X C, HE C X, SU L T, et al. Research progress on alkaloids[J]. Letters in Biotechnology,2006,17(3):476−479.
[72]	张德华, 黄仁术, 左露, 等. 生物碱的提取方法研究进展[J]. 中国野生植物资源,2010,29(5):15−20. [ZHANG D H, HUANG R S, ZUO L, et al. Progress on the method of extraction of alkaloids[J]. Chinese Wild Plant Resources,2010,29(5):15−20. doi: 10.3969/j.issn.1006-9690.2010.05.004
[73]	NEMATI N, AHMADI S H, TABAR HEYDAR K. Simultaneous determination of five opium alkaloids in underground waters using molecularly imprinted polymer-modified magnetic nanoparticle based dispersive micro-solid phase extraction followed by high performance liquid chromatography[J]. International Journal of Environmental Analytical Chemistry,2021,101(1):1−17. doi: 10.1080/03067319.2019.1659253
[74]	SADEGH N, ASFARAM A, JAVADIAN H, et al. Ultrasound-assisted solid phase microextraction-HPLC method based on Fe₃O₄@SiO₂-NH₂-molecularly imprinted polymer magnetic nano-sorbent for rapid and efficient extraction of harmaline from Peganum harmala extract[J]. Journal of Chromatography B,2021,1171:122640. doi: 10.1016/j.jchromb.2021.122640
[75]	WANG Y, YIN S, ZHAO C, et al. Preparation of a zirconium terephthalate metal-organic framework coated magnetic nanoparticle for the extraction of berberine prior to high-performance liquid chromatography analysis[J]. Journal of Separation Science,2021,44(6):1220−1230. doi: 10.1002/jssc.202001026
[76]	王兰兰, 宋晓卉, 杨笛, 等. 环境条件对植物有机酸影响研究进展[J]. 沈阳师范大学学报: 自然科学版,2019,37(3):236−239. [WANG L L, SONG X H, YANG D, et al. Progress of the effects of environmental conditions on organic acids in plants[J]. Journal of Shenyang Normal University (Natural Science Edition),2019,37(3):236−239.
[77]	鄢凌, 傅宏鑫, 王旭东, 等. 生物基有机酸提取分离技术研究进展[J]. 过程工程学报,2018,18(1):1−10. [YAN L, FU H X, WANG X D, et al. Recent advances on recovery and separation of biomass-based organic acids[J]. The Chinese Journal of Process Engineering,2018,18(1):1−10.
[78]	DAN W, HAO C, JIANG L, et al. Efficient separation of butyric acid by an aqueous two-phase system with calcium chloride[J]. Chinese Journal of Chemical Engineering,2010,18(4):533−537. doi: 10.1016/S1004-9541(10)60255-8
[79]	GAO M T, SHIMAMURA T, ISHIDA N, et al. Extractive lactic acid fermentation with tri-n-decylamine as the extractant[J]. Enzyme and Microbial Technology,2009,44(5):350−354. doi: 10.1016/j.enzmictec.2008.12.001
[80]	LIN S K C, DU C, BLAGA A C, et al. Novel resin-based vacuum distillation-crystallisation method for recovery of succinic acid crystals from fermentation broths[J]. Green Chemistry,2010,12(4):666−671. doi: 10.1039/b913021g
[81]	WANG B, DENG H, WU M, et al. Magnetic surface molecularly imprinted polymeric microspheres using gallic acid as a segment template for excellent recognition of ester catechins[J]. Analytical Methods,2018,10(27):3317−3324. doi: 10.1039/C8AY00903A
[82]	ZHANG Z, NIU D, LI Y, et al. Magnetic, core-shell structured and surface molecularly imprinted polymers for the rapid and selective recognition of salicylic acid from aqueous solutions[J]. Applied Surface Science,2018,435:178−186. doi: 10.1016/j.apsusc.2017.11.033
[83]	LI Y J, HE J Y, LI Q Y, et al. An edible molecularly imprinted material prepared by a new environmentally friendly deep eutectic solvent for removing oxalic acid from vegetables and human blood[J]. Analytical and Bioanalytical Chemistry,2022,414(7):2481−2491. doi: 10.1007/s00216-022-03889-9
[84]	杜亚朋, 王美, 李璐遥, 等. 基于化合物稳定性探讨炮制对含环烯醚萜类成分中药药性及功效影响的研究进展[J]. 中草药,2021,52(16):5039−5051. [DU Y P, WANG M, LI L Y, et al. Research progress on effect of processing on properties and efficacy of traditional Chinese medicine containing iridoid terpenoids based on stability of compound[J]. Chinese Traditional and Herbal Drugs,2021,52(16):5039−5051.
[85]	徐瑶, 徐树来, 刘志彬, 等. 灵芝三萜类化合物提取纯化及生物活性研究进展[J]. 食品工业科技,2022,43(11):458−464. [XU Y, XU S L, LIU Z B, et al. Research progress on the extraction, purification and biological activity of triterpenoids from the Ganoderma lucidum[J]. Science and Technology of Food Industry,2022,43(11):458−464.
[86]	WANG J, YE Q, YU N, et al. Preparation of multiresponsive hydrophilic molecularly imprinted microspheres for rapid separation of gardenia yellow and geniposide from gardenia fruit[J]. Food Chemistry,2022,374:131610. doi: 10.1016/j.foodchem.2021.131610
[87]	LI F, LI X, SU J, et al. A strategy of utilizing Cu²⁺-mediating interaction to prepare magnetic imprinted polymers for the selective detection of celastrol in traditional Chinese medicines[J]. Talanta,2021,231:122339. doi: 10.1016/j.talanta.2021.122339
[88]	ZHENG C, GAO R, ZHANG Y. Separation and recognition of biomacromolecule by molecular imprinting technique[J]. Se Pu= Chinese Journal of Chromatography,2006,24(3):309−314.
[89]	ANDAÇ M, GALAEV I Y, DENIZLI A. Affinity based and molecularly imprinted cryogels: Applications in biomacromolecule purification[J]. Journal of Chromatography B,2016,1021:69−80. doi: 10.1016/j.jchromb.2015.09.034
[90]	孟姣姣. 低共熔溶剂绿色萃取技术用于生物大分子的分离分析研究[D]. 长沙: 湖南大学, 2020 MENG J J. The research on deep eutectic solvent-based green extraction technology for the separation and analysis of biomacromolecules[D]. Changsha: Hunan University, 2020.
[91]	WANG C, GAO X, CHEN Z, et al. Preparation, characterization and application of polysaccharide-based metallic nanoparticles: A review[J]. Polymers,2017,9(12):689. doi: 10.3390/polym9120689
[92]	CHANG B, ZHANG M, QING G, et al. Dynamic biointerfaces: From recognition to function[J]. Small,2015,11(9-10):1097−1112. doi: 10.1002/smll.201402038
[93]	黄微薇, 赵倩玉, 杨鑫, 等. 乙烯基功能化磁性分子印迹聚合物的制备和识别性能研究[J]. 功能材料,2019,50(1):1018−1025. [HUANG W W, ZHAO Q Y, YANG X, et al. Preparation and identification of viny functionalized magnetic molecularly imprinted polymers[J]. Journal of Functional Materials,2019,50(1):1018−1025. doi: 10.3969/j.issn.1001-9731.2019.01.003
[94]	黄微薇, 赵倩玉, 杨鑫, 等. 环氧功能化双功能磁性分子印迹聚合物的合成及其在多糖吸附中的应用[J]. 色谱,2019,37(7):673−682. [HUANG W W, ZHAO Q Y, YANG X, et al. Synthesis and applications of epoxy-functionalized bi-functional magnetic molecularly imprinted polymer for polysaccharide absorption[J]. Chinese Journal of Chromatography,2019,37(7):673−682. doi: 10.3724/SP.J.1123.2019.01018
[95]	ALI T H, MANDAL A M, HEIDELBERG T, et al. Sugar based cationic magnetic core-shell silica nanoparticles for nucleic acid extraction[J]. RSC Advances,2022,12(22):13566−13579. doi: 10.1039/D2RA01139E
[96]	ALI T H, MANDAL A M, HEIDELBERG T, et al. Ionic magnetic core-shell nanoparticles for DNA extraction[J]. RSC Advances,2020,10(64):38818−38830. doi: 10.1039/D0RA05933A
[97]	GHEYBALIZADEH H, HEJAZI P. Influence of hydrophilic and hydrophobic functional monomers on the performance of magnetic molecularly imprinted polymers for selective recognition of human insulin[J]. Reactive and Functional Polymers,2022,171:105152. doi: 10.1016/j.reactfunctpolym.2021.105152
[98]	CHEN F, MAO M, WANG J, et al. A dual-step immobilization/imprinting approach to prepare magnetic molecular imprinted polymers for selective removal of human serum albumin[J]. Talanta,2020,209:120509. doi: 10.1016/j.talanta.2019.120509
[99]	FANG X, WANG Z, SUN N, et al. Magnetic metal oxide affinity chromatography-based molecularly imprinted approach for effective separation of serous and urinary phosphoprotein biomarker[J]. Talanta,2021,226:122143. doi: 10.1016/j.talanta.2021.122143