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Analytical and Bioanalytical Chemistry

, Volume 408, Issue 19, pp 5319–5328 | Cite as

Preparation of hydrophilic molecularly imprinted polymers via bulk polymerization combined with hydrolysis of ester groups for selective recognition of iridoid glycosides

  • Wenhua Ji
  • Mingming Zhang
  • Qianshan Gao
  • Li Cui
  • Lizong Chen
  • Xiao WangEmail author
Research Paper

Abstract

Hydrophilic molecularly imprinted polymers (H-MIP) with molecular recognition ability for iridoid glycosides (IGs) have been obtained via bulk polymerization combined with hydrolysis of ester groups. H-MIP were characterized by Fourier transform infrared spectroscopy (FT-IR). The hydrophilcity was measured by the contact angle measurement and the water dispersion stability. The obtained H-MIP demonstrated high selectivity and specific binding ability to five IGs in aqueous media. The group extraction efficiency of molecular imprinted solid-phase extraction (MISPE) for five IGs was investigated, including loading sample, breakthrough volume, washing solvent, and elution solvent. Compared with non-imprinted solid-phase extraction (NISPE), the higher average recovery (95.5 %) of five IGs with lower relative standard deviations values (below 6.1 %) using MISPE combined with high-performance liquid chromatography (HPLC) were achieved at three spiked levels in three blank samples. Under the optimum MISPE conditions, the wide linear range with the correlation coefficient of R 2  ≥ 0.9950 for five IGs with low limits of detection (LOD) and quantification (LOQ) (0.01–0.08 and 0.03–0.27 μg mL−1, respectively) were obtained. Chromatograms obtained using MISPE columns demonstrated that the matrix interference has been minimized and great interferences around IGs were also eliminated efficiently. These results indicated that the developed MISPE-HPLC method was selective, accurate, and applicable for the determination of IGs in water media.

Graphical Abstract

Preparation of hydrophilic molecularly imprinted polymers via bulk polymerization combined with hydrolysis of ester groups

Keywords

Molecularly imprinted polymers HPLC Natural products Solid phase extraction Iridoid glycosides 

Notes

Acknowledgments

This study was financially supported by the Natural Science Foundation of Shandong (ZR2015BQ005) and a research grant from Shandong Analysis and Test Center.

Compliance with ethical standards

Conflicts of interest

The authors declare that they have no conflict of interests.

Supplementary material

216_2016_9625_MOESM1_ESM.pdf (260 kb)
ESM 1 (PDF 260 kb)

References

  1. 1.
    Cheong WJ, Yang SH, Ali F. Molecularly imprinted polymers for separation science: a review of reviews. J Sep Sci. 2013;36:609–28.CrossRefGoogle Scholar
  2. 2.
    Martin-Esteban A. Molecularly-imprinted polymers as a versatile, highly selective tool in sample preparation. Trac-Trend Anal Chem. 2013;45:169–81.CrossRefGoogle Scholar
  3. 3.
    Ye L, Mosbach K. Molecular imprinting: synthetic materials as substitutes for biological antibodies and receptors. Chem Mater. 2008;20:859–68.CrossRefGoogle Scholar
  4. 4.
    Ji W, Ma X, Zhang J, Xie H, Liu F, Wang X. Preparation of the high purity gingerols from ginger by dummy molecularly imprinted polymers. J Chromatogr A. 2015;1387:24–31.CrossRefGoogle Scholar
  5. 5.
    Fan W, Gao M, He M, Chen B, Hu B. Cyromazine imprinted polymers for selective stir bar sorptive extraction of melamine in animal feed and milk samples. Analyst. 2015;140:4057–67.CrossRefGoogle Scholar
  6. 6.
    Ye L. Molecularly imprinted polymers with multi-functionality. Anal Bioanal Chem. 2016;408:1727–33.CrossRefGoogle Scholar
  7. 7.
    Wei W, Liang R, Wang Z, Qin W. Hydrophilic molecularly imprinted polymers for selective recognition of polycyclic aromatic hydrocarbons in aqueous media. RSC Adv. 2015;5:2659–62.CrossRefGoogle Scholar
  8. 8.
    You QP, Peng MJ, Zhang YP, Guo JF, Shi SY. Preparation of magnetic dummy molecularly imprinted polymers for selective extraction and analysis of salicylic acid in Actinidia chinensis. Anal Bioanal Chem. 2014;406:831–9.CrossRefGoogle Scholar
  9. 9.
    Chen L, Xu S, Li J. Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev. 2011;40:2922–42.CrossRefGoogle Scholar
  10. 10.
    Zhao M, Zhang C, Zhang Y, Guo X, Yan H, Zhang H. Efficient synthesis of narrowly dispersed hydrophilic and magnetic molecularly imprinted polymer microspheres with excellent molecular recognition ability in a real biological sample. Chem Commun. 2014;50:2208–10.CrossRefGoogle Scholar
  11. 11.
    Hao Y, Gao R, Shi L, Liu D, Tang Y, Guo Z. Water-compatible magnetic imprinted nanoparticles served as solid-phase extraction sorbents for selective determination of trace 17beta-estradiol in environmental water samples by liquid chromatography. J Chromatogr A. 2015;1396:7–16.CrossRefGoogle Scholar
  12. 12.
    Zhang H. Water-compatible molecularly imprinted polymers: promising synthetic substitutes for biological receptors. Polymer. 2014;55:699–714.CrossRefGoogle Scholar
  13. 13.
    Adali-Kaya Z, Bui BTS, Falcimaigne-Cordin A, Haupt K. Molecularly imprinted polymer nanomaterials and nanocomposites: atom-transfer radical polymerization with acidic monomers. Angew Chem Int Ed. 2015;54:5192–5.CrossRefGoogle Scholar
  14. 14.
    Yan H, Row KH, Yang G. Water-compatible molecularly imprinted polymers for selective extraction of ciprofloxacin from human urine. Talanta. 2008;75:227–32.Google Scholar
  15. 15.
    Benito-Pena E, Martins S, Orellana G, Moreno-Bondi MC. Water-compatible molecularly imprinted polymer for the selective recognition of fluoroquinolone antibiotics in biological samples. Anal Bioanal Chem. 2009;393:235–45.CrossRefGoogle Scholar
  16. 16.
    Yang Y, Long Y, Cao Q, Li K, Liu F. Molecularly imprinted polymer using β-cyclodextrin as functional monomer for the efficient recognition of bilirubin. Anal Chim Acta. 2008;606:92–7.CrossRefGoogle Scholar
  17. 17.
    Kyaas GZ, Bikiaris DN, Lazaridis NK. Selective separation of basic and reactive dyes by molecularly imprinted polymers (MIPs). Chem Eng J. 2009;149:263–72.CrossRefGoogle Scholar
  18. 18.
    Yang K, Berg MM, Zhao C, Ye L. One-pot synthesis of hydrophilic molecularly imprinted nanoparticles. Macromolecules. 2009;42:8739–46.CrossRefGoogle Scholar
  19. 19.
    Puoci F, Lemma F, Cirillo G, Curcio M, Parisi OI, Spizzirri UG, et al. New restricted access materials combined to molecularly imprinted polymers for selective recognition/release in water media. Eur Polym J. 2009;45:1634–40.CrossRefGoogle Scholar
  20. 20.
    Ji W, Chen L, Ma X, Wang X, Gao Q, Geng Y, et al. Molecularly imprinted polymers with novel functional monomer for selective solid-phase extraction of gastrodin from the aqueous extract of Gastrodia elata. J Chromatogr A. 2014;1342:1–7.CrossRefGoogle Scholar
  21. 21.
    Ji W, Zhang M, Wang D, Wang X, Liu J, Huang L. Superhydrophilic molecularly imprinted polymers based on a water-soluble functional monomer for the recognition of gastrodin in water media. J Chromatogr A. 2015;1425:88–96.CrossRefGoogle Scholar
  22. 22.
    Boros CA, Stemrmitz FR. Iridoids. An updated review. Part I. J Nat Prod. 1990;53:1055–147.CrossRefGoogle Scholar
  23. 23.
    Boros CA, Stemrmitz FR. Iridoids. An updated review. Part II. J Nat Prod. 1991;54:1173–246.CrossRefGoogle Scholar
  24. 24.
    Chinese Pharmacopoeia Commission, editor. Chinese pharmacopoeia, vol. I. Beijing: People’s Medical Publishing House; 2010. p. 26.Google Scholar
  25. 25.
    Chinese Pharmacopoeia Commission, editor. Chinese pharmacopoeia, vol. I. Beijing: People’s Medical Publishing House; 2010. p. 597.Google Scholar
  26. 26.
    Song Y, Li SL, Wu MH, Li HJ, Li P. Qualitative and quantitative analysis of iridoid glycosides in the flower buds of Lonicera species by capillary high performance liquid chromatography coupled with mass spectrometric detector. Anal Chim Acta. 2006;564:211–8.CrossRefGoogle Scholar
  27. 27.
    Cao XY, Wang ZZ. Simultaneous determination of four iridoid and secoiridoid glycosides and comparative analysis of Radix Gentianae macrophyllae and their related substitutes by HPLC. Phytochem Anal. 2010;21:348–54.CrossRefGoogle Scholar
  28. 28.
    Yang L, Wang Y, Wang L, Xiao H, Wang Z, Hu Z. Rapid quantification of iridoid glycosides analogues in the formulated Chinese medicine Longdan Xiegan Decoction using high-performance liquid chromatography coupled with mass spectromentry. J Chromatogr A. 2009;1216:2098–103.CrossRefGoogle Scholar
  29. 29.
    He ML, Cheng XW, Chen JK, Zhou TS. Simultaneous determination of five major biologically active ingredients in different parts of Gardenia jasminoides fruits by HPLC with diode-array detection. Chromatographia. 2006;64:713–7.CrossRefGoogle Scholar
  30. 30.
    Bergonzi MC, Righeschi C, Isacchi B, Bilia AR. Identification and quantification of constituents of Gardenia jasminoides Ellis (Zhizi) by HPLC-DAD-ESI-MS. Food Chem. 2012;134:1199–204.CrossRefGoogle Scholar
  31. 31.
    Coran SA, Mulas S, Vasconi A. Profiling of components and validated determination of iridoids in Gardenia jasminoides Ellis fruit by a high-performance-thin-layer-chromatography/mass spectrometry approach. J Chromatogr A. 2014;1325:221–6.CrossRefGoogle Scholar
  32. 32.
    Han Y, Wen J, Zhou T, Fan G. Chemical fingerprinting of Gardenia jasminoides Ellis by HPLC-DAD-ESI-MS combined with chemometrics methods. Food Chem. 2015;188:648–57.CrossRefGoogle Scholar
  33. 33.
    Ji W, Xie H, Zhou J, Wang X, Ma X, Huang L. Water-compatible molecularly imprinted polymers for selective solid phase extraction of dencichine from the aqueous extract of Panax notoginseng. J Chromatogr B. 2016;1008:225–33.CrossRefGoogle Scholar
  34. 34.
    Ji W, Ma X, Xie H, Chen L, Wang X, Zhao H, et al. Molecularly imprinted polymers with synthetic dummy template for simultaneously selective removal and enrichment of ginkgolic acids from Ginkgo biloba L. leaves extracts. J Chromatogr A. 2014;1368:44–51.CrossRefGoogle Scholar
  35. 35.
    Zengina A, Yildirima E, Tamerb U, Caykara T. Molecularly imprinted superparamagnetic iron oxide nanoparticles for rapid enrichment and separation of cholesterol. Analyst. 2013;138:7238–45.CrossRefGoogle Scholar
  36. 36.
    Zhang L, Wu J, Wang Y, Long Y, Zhao N, Xu J. Combination of bioinspiration: a general route to superhydrophobic particles. J Am Chem Soc. 2012;134:9879–81.CrossRefGoogle Scholar
  37. 37.
    Lenain P, Mavungu JDD, Dubruel P, Robbens J, Saeger SD. Development of suspension polymerized molecularly imprinted beads with metergoline as template and application in a solid-phase extraction procedure toward ergot alkaloids. Anal Chem. 2012;84:10411–8.CrossRefGoogle Scholar
  38. 38.
    Software calculated value from SciFinder Scholar database 2008. http://www.cas.org/products/sfacad/.

Copyright information

© Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  • Wenhua Ji
    • 1
  • Mingming Zhang
    • 2
  • Qianshan Gao
    • 1
  • Li Cui
    • 1
  • Lizong Chen
    • 1
  • Xiao Wang
    • 1
    • 2
    Email author
  1. 1.Shandong Key Laboratory of TCM Quality Control Technology, Shandong Analysis and Test CenterShandong Academy of SciencesJinanChina
  2. 2.School of Life SciencesShandong Normal UniversityJinanChina

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