Sorption Preconcentration of Quercetin Using Molecularly Imprinted Phloroglucinol–Melamine–Formaldehyde Resins

Yu. Yu. Petrova; Петрова Ю. Ю.; E. V. Bulatova; Булатова Е. В.; E. V. Kukhtenko; Кухтенко Е. В.

doi:10.31857/S0044450223120137

Sorption Preconcentration of Quercetin Using Molecularly Imprinted Phloroglucinol–Melamine–Formaldehyde Resins

Authors: Petrova Y.Y.¹, Bulatova E.V.¹, Kukhtenko E.V.²
Affiliations:
1. Surgut State University, 628412, Surgut, Russia
2. ITMO University, 197101, St. Petersburg, Russia
Issue: Vol 78, No 12 (2023)
Pages: 1096-1105
Section: ORIGINAL ARTICLES
Submitted: 31.01.2025
URL: https://ruspoj.com/0044-4502/article/view/650267
DOI: https://doi.org/10.31857/S0044450223120137
EDN: https://elibrary.ru/YWUKXG
ID: 650267

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract

Hydrophilic quercetin-imprinted phloroglucinol–melamine–formaldehyde resins are obtained. The obtained samples are studied by Fourier-transform IR spectroscopy and laser diffraction. The phloroglucinol–melamine ratio (3 : 1) is optimized at the sorption capacity of the molecularly imprinted resin (1.7 μmol/g) with respect to quercetin 2.6 times higher than that of the non-imprinted resin. It is shown that the kinetics of quercetin rebinding by both molecularly imprinted and non-imprinted resins obeys the pseudo-second order model, and the isotherms follow the Freundlich model, which indicates the inhomogeneity of the resin surface. The resin imprinted with quercetin demonstrated high selectivity to morine (a structural analogue of quercetin of the flavonol class) and caffeine. At that it is shown that quercetin can be used as a pseudotemplate for the separation and preconcentration of naringenin (a representative of flavanones) and rutin (a representative of flavonols).

Keywords

molecular imprinting, rebinding, morin, naringenin, rutin, caffeine

References

Pichon V., Delaunay N., Combès A. Sample preparation using molecularly imprinted polymers // Anal. Chem. 2020. V. 92. P. 16. https://doi.org/10.1021/acs.analchem.9b04816
Kaya S.I., Cetinkaya A., Ozkan S.A. Molecularly imprinted polymers as highly selective sorbents in sample preparation techniques and their applications in environmental water analysis // Trends Environ. Anal. Chem. 2023. V. 37. Article e00193. https://doi.org/10.1016/j.teac.2022.e00193
Villa C.C., S’anchez L.T., Valencia G.A., Ahmed S., Guti’errez T.J. Molecularly imprinted polymers for food applications: A review // Trends Food Sci. Technol. 2021. V. 111. P. 642. https://doi.org/10.1016/j.tifs.2021.03.003
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. Article 2200499. https://doi.org/10.1002/mame.202200499
Zhang W., Zhang Y., Wang R., Zhang P., Zhang Y., Randell E., Zhang M., Jia Q. A review: Development and application of surface molecularly imprinted polymers toward amino acids, peptides, and proteins // Anal. Chim. Acta. 2022. V. 1234. Article 340319. https://doi.org/10.1016/j.aca.2022.340319
Zhou T., Ding L., Che G., Jiang W., Sang L. Recent advances and trends of molecularly imprinted polymers for specific recognition in aqueous matrix: Preparation and application in sample pretreatment // Trends Anal. Chem. 2019. V. 114. P. 11. https://doi.org/10.1016/j.trac.2019.02.028
Han Y., Wang Z., Jia J., Bai L., Liu H., Shen S., Yan H. Newly designed molecularly imprinted 3-aminophenol-glyoxal-urea resin as hydrophilic solid-phase extraction sorbent for specific simultaneous determination of three plant growth regulators in green bell peppers // Food Chem. 2020. V. 311. Article 125999. https://doi.org/10.1016/j.foodchem.2019.125999
Zou D., Li P., Yang C., Han D., Yan H. Rapid determination of perfluorinated compounds in pork samples using a molecularly imprinted phenolic resin adsorbent in dispersive solid phase extraction-liquid chromatography tandem mass spectrometry // Anal. Chim. Acta. 2022. V. 1226. Article 340271. https://doi.org/10.1016/j.aca.2022.340271
Wang M., Qiao F., Yan H. A simple and benign protocol for the synthesis of a deep eutectic solvent-based hydrophilic molecularly imprinted resin in water for excellent selective molecular recognition in aqueous phase // Green Chem. 2021. V. 23. Article 5179. https://doi.org/10.1039/d1gc00789k
Alhawiti A.S., Monier M., Elsayed N.H. Designing of amino functionalized imprinted polymeric resin for enantio-separation of (±)-mandelic acid racemate // React. Funct. Polym. 2021. V. 160. Article 104828. https://doi.org/10.1016/j.reactfunctpolym.2021.104828
Wang Y., Zhao W., Tian X., Song H., Gao R., Tang X., Zhang X., Hao Y., Tang Y. High-efficiency recognition and detection of sulindac in sewage using hydrophilic imprinted resorcinol-formaldehyde resin magnetic nano-spheres as SPE adsorbents combined with HPLC // Chem. Eng. J. 2020. V. 392. Article 123716. https://doi.org/10.1016/j.cej.2019.123716
Jahankhah S., Sabzehmeidani M.M., Ghaedi M., Dashtian K., Abbasi-Asl H. Hydrophilic magnetic molecularly imprinted resin in PVDF membrane for efficient selective removal of dye // J. Environ. Manage. 2021. V. 300. Article 113707. https://doi.org/10.1016/j.jenvman.2021.113707
Zhou T., Wang Y., Li T., Li H., Yang C., Sun D., Wang D., Liu C., Che G. Fabricating magnetic hydrophilic molecularly imprinted resin with enhanced adsorption and recognition performance for targeted detecting chlorophenols in environmental water // Chem. Eng. J. 2021. V. 420. Article 129904. https://doi.org/10.1016/j.cej.2021.129904
Liang S., Yan H., Cao J., Han Y., Shen S., Bai L. Molecularly imprinted phloroglucinol-formaldehyde-melamine resin prepared in a deep eutectic solvent for selective recognition of clorprenaline and bambuterol in urine // Anal. Chim. Acta. 2016. V. 951. P. 68. https://doi.org/10.1016/j.aca.2016.11.009
Ansell R.J. Characterization of the binding properties of molecularly imprinted polymers / Advances in Biochemical Engineering/Biotechnology. V. 150. Molecularly Imprinted Polymers in Biotechnology / Eds. Mattiasson B., Ye L. Springer, 2015. P. 51. https://doi.org/10.1007/10_2015_316
Liu M., Tran T.M., Elhaj A.A.A., Torsetnes S.B., Jensen O.N., Sellergren B., Irgum K. Molecularly imprinted porous monolithic materials from melamine-formaldehyde for selective trapping of phosphopeptides // Anal. Chem. 2017. V. 89. № 17. P. 9491. https://doi.org/10.1021/acs.analchem.7b02470
Socrates G. Infrared and Raman Characteristic Group Frequencies. Table and Charts. John Wiley & Sons, 2001. 347 p.
Petrova Yu.Yu., Bulatova E.V., Sevast’yanova E.V., Mateyshina Yu.G. Quercetin-imprinted monolithic polymer // Mater. Today Proc. 2020. V. 31. Part 3. P. 555. https://doi.org/10.1016/j.matpr.2020.06.213
Zhi K., Li Z., Luo H., Ding Y., Chen F., Tan Y., Liu H. Selective adsorption of quercetin by the sol-gel surface molecularly imprinted polymer // Polymers. 2023. V. 15. № 4. Article 905. https://doi.org/10.3390/polym15040905