Abstract
Extraction and purification of α- and β-amanitins from mushroom samples are still challenges. Surface-imprinted core–shell microspheres were synthesized combining target recognition determinant imprinting and thiol-ene click reaction, and applied to the extraction of α- and β-amanitins in mushroom samples. The highly efficient thiol-ene click reaction method offers a simple condition during the crosslinking process of molecularly imprinted polymers (MIP), and the functional monomer using could be successfully introduced onto the silica microspheres. The synthesized SiO2@MIP were characterized by scanning electron microscopy (SEM), Fourier transform infrared (FTIR), and thermogravimetric analysis (TGA). The measurement of SiO2@MIP resultants using high-performance liquid chromatography (HPLC) clearly demonstrates that SiO2@MIP not only display excellent affinity, but also show good selective recognition to α- and β-amanitins. The imprinted microspheres were successfully applied as sorbents for the extraction of α- and β-amanitins from mushrooms, attaining recoveries of 76.8–79.2%. Furthermore, the samples were effectively purified according to the chromatogram.
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Kaya E, Yilmaz I, Admis O, Oktay M, Bayram R, Bakirci S, Yaykasli KO, Kandis H, Saritas A, Katirci Y (2016) Toxin Rev 35:4–9
Kaplan CD, Larsson KM, Kornberg RD (2008) Mol Cell 30:547–556
Moldenhauer G, Salnikov AV, Lüttgau S, Herr I, Anderl J, Faulstich H (2012) J Natl Cancer I 104:622–634
Kaya E, Bayram R, Yaykasli KO, Yilmaz I, Bayram S, Yaykasli E, Yavuz MZ, Gepdiremen A (2013) Turk J Med Sci 24:S105
Golbus MS, Calarco PG, Epstein CJ (2010) J Exp Zool Part A 186:207–216
Magdalan J, Ostrowska A, Piotrowska A, Izykowska I, Nowak M, Gomułkiewicz A, Podhorskaokołów M, Szelag A, Dziegiel P (2010) Folia Histochem Cyto 48:58–62
Bakirci S, Bayram R, Yilmaz I, Yaykasli KO, Bayram S, Kaya E (2015) Toxin Rev 34:200–205
Hataminia F, Farhadian N, Karimi M, Ebrahimi M (2018) J Taiwan Inst Chem E 91:1–9
Passos H, Freire MG, Coutinho JAP (2014) Green Chem 16:4786–4815
Soria AC, Villamiel M (2010) Trends Food Sci Tech 21:323–331
Hokanson GC, Matyunas NJ (2010) J Pharm Sci 70:329–331
Zhang L, Wang Y, Guo X, Wu S (2017) J Chromatogr A 1491:108–116
Chen WB, Li SQ, Chen LJ, Fang MJ, Chen QC, Wu Z, Wu YL, Qiu YK (2015) J Chromatogr B 997:179–186
Berton P, Lana NB, Ríos JM, García-Reyes JF, Altamirano JC (2016) Anal Chim Acta 905:24–41
Chen L, Wang X, Lu W, Wu X, Li J (2016) Chem Soc Rev 45:2137–2211
Yin J, Cui Y, Yang G, Wang H (2010) Chem Commun 46:7688–7690
Wang XN, Liang RP, Meng XY, Qiu JD (2014) J Chromatogr A 1362:301–308
Tan J, Guo M, Tan L, Geng Y, Huang S, Tang Y, Su C, Lin CC, Liang Y (2018) Sensor Actuat B: Chem 274:627–635
Saadati F, Ghahramani F, Shayani-jam H, Piri F, Yaftian MR (2018) J Taiwan Inst Chem E 86:213–221
Li G, Row KH (2018) Chromatographia 81:73–88
Combes A, Kadhirvel P, Bordron L, Pichon V (2019) Chromatographia 82:287–295
Yu H, Koide H, Urakami T, Kanazawa H, Kodama T, Oku N, Shea KJ (2010) J Am Chem Soc 132:6644–6645
Shoghi E, Mirahmadi-Zare SZ, Ghasemi R, Asghari M, Poorebrahim M, Nasr-Esfahani M-H (2018) Microchim Acta 185:241
Verheyen E, Schillemans JP, Van WM, Demeniex MA, Hennink WE, van Nostrum CF (2011) Biomaterials 32:3008–3020
Feng L, Tan L, Li H, Xu Z, Shen G, Tang Y (2015) Biosens Bioelectron 69:265–271
Li Y, Tan L, Li H, Xu Z, Zuo X, Tang Y (2014) J Chromatogr A 1324:190–197
Bhairamadgi NS, Gangarapu S, Campos MAC, Paulusse JMJ, Rijn CJMV, Han Z (2013) Langmuir 29:4535–4542
Christian S, Susann N, Roland F, Bart Jan R (2012) Small 8:569–577
Xue C-H, Guo X-J, Zhang M-M, Ma J-Z, Jia S-T (2015) J Mater Chem A 3:21797–21804
Shen A, Guo Z, Yu L, Cao L, Liang X (2011) Chem Commun 47:4550–4552
Chen L, Ou J, Liu Z, Lin H, Wang H, Dong J, Zou H (2015) J Chromatogr A 1394:103–110
Shah J, Pinnavaia TJ (2005) Chem Commun 12:1598–1600
Wei S, Jakusch M, Mizaikoff B (2006) Anal Chim Acta 578:50–58
Boulanouar S, Combès A, Mezzache S, Pichon V (2017) J Chromatogr A 1513:59–68
Acknowledgements
This work was financially supported by a grant from the Natural Science Foundation of China (21275057), the Scientific and Technological Innovation Foundation of Foshan Gaoming (2014F08), and Project of Education Science Planning in Guangdong Province (2017GXJK186).
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Xu, S., Tan, J., Chen, X. et al. Preparation of Synthetic Amanitin Epitope Imprinted Polymers via Thiol-ene Click Reaction for Recognition and Extraction α- and β-Amanitins from Mushrooms. Chromatographia 82, 1355–1363 (2019). https://doi.org/10.1007/s10337-019-03751-8
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DOI: https://doi.org/10.1007/s10337-019-03751-8