Abstract
In this study, a novel molecularly imprinted polymer (MIL@MIP) that could selectively recognize the trichlorfon and monocrotophos was synthesized using metal-organic framework MIL-101 as support material. The prepared MIL@MIP was characterized by Fourier transform infrared, thermogravimetric analysis, scanning electron microscope, static adsorption, kinetic adsorption, and competitive adsorption analyses. Using this material as sorbent, a new method of molecularly imprinted solid-phase extraction coupled with high performance liquid chromatography for simultaneous determination of trichlorfon and monocrotophos was established. Under optimal conditions, the limit of detection (LOD) of this method for trichlorfon and monocrotophos detection was 0.011 and 0.015 mg/kg, respectively. The relative standard deviation (RSD) for five replicates of 0.05 mg/L trichlorfon and monocrotophos mixed solutions was within the range of 1.8 to 3.7 %. Apple and pear samples spiked with the two kinds of organophosphate pesticides were extracted and determined by using this method with good recoveries ranging from 86.5 to 91.7 %. Moreover, this method was successfully applied for the detection of the two organophosphate pesticides in strawberry samples.
Similar content being viewed by others
References
Baldim IM, Figueiredo EC, Martins I (2012) Application of the molecularly imprinted solid-phase extraction to the organophosphate residues determination in strawberries. Anal Bioanal Chem 404(6–7):1959–1966
Cai CP, Liang M, Wen RR (1995) Rapid multi-residue screening method for organophosphate pesticides in vegetables. Chromatographia 40:417–420
Capitan F, Capitan-Vallvey LF, Fernandez MD (1996) Determination of colorant matters mixtures in foods by solid-phase spectrophotometry. Anal Chim Acta 331:141–148
Casida JE, Quistad GB (2004) Organophosphate toxicology: safety aspects of nonacetylcholinesterase secondary targets. Chem Res Toxicol 17:983–998
Chen Q, Fung Y (2010) Capillary electrophoresis with immobilized quantum dot fluorescence detection for rapid determination of organophosphorus pesticides in vegetables. Electrophoresis 31(18):3107–3114
Chen H, Chen RW, Feng R, Li SQ (2009) Simultaneous analysis of carbamate and organophosphorus pesticides in water by single-drop microextraction coupled with GC-MS. Chromatographia 70(1):165–172
Cuong LP, Evgen’ev MI, Gumerov FM (2012) Determination of pesticides in the hair of Vietnamese by means of supercritical CO2 extraction and GC–MS analysis. J Supercrit Fluid 61:86–91
Ferey G, Mellot-Draznieks C, Serre C, Millange F, Dutour J, Surble SI, Margiolaki I (2005) A chromium terephthalate-based solid with unusually large pore volumes and surface area. Sci 309:2040–2042
Lee HS, Ah Kim Y, Ae Cho Y (2002) Oxidation of organophosphorus pesticides for the sensitive detection by a cholinesterase-based biosensor. Chemosphere 46:571–576
Liang Y, Liu XJ, Yu XY, Fan MT (2008) Synthesis of three haptens for the class-specific immunoassay of O,O-dimethyl organophosphorus pesticides and effect of hapten heterology on immunoassay sensitivity. Anal Chim Acta 615(2):174–183
Liu HM, Kong WJ, Qi Y, Gong B, Miao Q, Wei JH, Yang MH (2014) Streamlined pretreatment and GC–FPD analysis of multi-pesticide residues in perennial Morinda roots: a tropical or subtropical plant. Chemosphere 95:33–40
Meng L, Qiao XG, Song JM, Xu ZX, Xin JH, Zhang Y (2011) Study of an online molecularly imprinted solid phase extraction coupled to chemiluminescence sensor for the determination of trichlorfon in vegetables. J Agric Food Chem 59:12745–12751
Mol H, Dam RV, Steijger OM (2003) Determination of polar organophosphorus pesticides in vegetables and fruits using liquid chromatography with tandem mass spectrometry: selection of extraction solvent. J Chromatogr A 1015:119–127
Mulchandani A, Chen W, Mulchandani P (2001) Biosensors for direct determination of organophosphate pesticides. Biosens Bioelectron 16:225–230
Perret D, Gentili A, Marchese S (2002) Validation of a method for the determination of multiclass pesticide residues in fruit juices by liquid chromatography/tandem mass spectrometry after extraction by matrix solid-phase dispersion. J AOAC Int 85:724–730
Pirsaheb M, Fattahi N, Shamsipur M (2013) Determination of organophosphorous pesticides in summer crops using ultrasound-assisted solvent extraction followed by dispersive liquid-liquid microextraction based on the solidification of floating organic drop. Food Control 34:378–385
Qian K, Fang GZ, Wang S (2011) A novel core-shell molecularly imprinted polymer based on metal-organic frameworks as a matrix. Chem Commun 47:10118–10120
Razieh F, Hamid A, Majid M, Mona M (2013) Nano-rod catalysts: building MOF bottles (MIL-101 family as heterogeneous single-site catalysts) around vanadium oxide ships. J Mol Catal A-Chem 374–375:46–52
Rial-Otero R, Gaspar EM, Moura I (2007) Chromatographic-based methods for pesticide determination in honey: an overview. Talanta 71:503–514
Seebunrueng K, Santaladchaiyakit Y, Srijaranai S (2014) Vortex-assisted low density solvent based demulsified dispersive liquid-liquid microextraction and high-performance liquid chromatography for the determination of organophosphorus pesticides in water samples. Chemosphere 103:51–58
Soleimani M, Ghaderi S, Afshar MG (2012) Synthesis of molecularly imprinted polymer as a sorbent for solid phase extraction of bovine albumin from whey, milk, urine and serum. Microchem J 100:1–7
Stafiej A, Pyrzynska K, Regan F (2007) Determination of antiinflammatory drugs and estrogens in water by HPLC with UV detection. J Sep Sci 30:985–991
Theodoridis G, Lasáková M, Škeříková V, Tegou A, Giantsiou N, Jandera P (2006) Molecular imprinting of natural flavonoid antioxidants: application in solid-phase extraction for the sample pretreatment of natural products prior to HPLC analysis. J Sep Sci 29:2310–2321
Tian F, Liu WJ, Fang HS, An M, Duan SS (2014) Determination of six organophosphorus pesticides in water by single-drop microextraction coupled with GC-NPD. Chromatographia 77:487–492
Wang S, Xu ZX, Fang GZ, Duan ZJ, Zhang Y, Chen S (2007) Synthesis and characterization of a molecularly imprinted silica gel sorbent for the on-line determination of trace Sudan I in chilli powder through high-performance liquid chromatography. J Agric Food Chem 55:3869–3876
Wang XL, Qiao XG, Ma Y, Zhao T, Xu ZX (2013) Simultaneous determination of trace nine organophosphorous pesticide residues in fruit samples using molecularly imprinted matrix solid-phase dispersion followed by gas chromatography. J Agric Food Chem 61:3821–3827
Xin JH, Qiao XG, Xu ZX, Zhou J (2013) Molecularly imprinted polymer as sorbent for solid-phase extraction coupling to gas chromatography for the simultaneous determination of trichlorfon and monocrotophos residues in vegetables. Food Anal Method 6:274–281
Xu ZX, Fang GZ, Wang S (2010) Molecularly imprinted solid phase extraction coupled to high-performance liquid chromatography for determination of trace dichlorvos residues in vegetables. Food Chem 119:845–850
Xue M, Shen JY, Wang D, Yin L, Zhuang XL, Meng ZH (2015) Determination of trichlorfon in samples of spicy vegetables using a molecularly imprinted solid phase extraction technique. Anal Method 7:2420–2424
Yang HH, Zhang SQ, Tan F, Zhuang ZX, Wang XR (2005) Surface molecularly imprinted nanowires for biorecognition. J Am Chem Soc 127:1378–1379
You XW, Xing ZK, Liu FM, Jiang NW (2013) Air-assisted liquid–liquid microextraction used for the rapid determination of organophosphorus pesticides in juice samples. J Chromatogr A 1311:41–47
Zhang X, Zhang LM, Yang YL, Xu ZX (2016) Preparation and characterization of a molecularly imprinted polymer for selective recognition of trichlorfon and monocrotophos. J Macromol Sci Phys 55:382–392
Zhao T, Gao HJ, Wang XL, Zhang LM, Qiao XG, Xu ZX (2014) Study on a molecularly imprinted solid-phase extraction coupled to capillary electrophoresis method for the determination of trace trichlorfon in vegetables. Food Anal Method 7:1159–1165
Acknowledgments
This work was supported by the National Natural Science Foundation of China (project no. 31471649 and 31171699) and Western Economic Uplift and Poverty Alleviation Development Projects of Shandong (project no. 49).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Funding
Dr. Zhixiang Xu has received research grants from the National Natural Science Foundation of China and Western Economic Uplift and Poverty Alleviation Development Projects of Shandong.
Conflict of Interest
Deqing Li declares that she has no conflict of interest. Xin Zhang declares that she has no conflict of interest. Feifan kong declares that he has no conflict of interest. Xuguang Qiao declares that he has no conflict of interest. Zhixiang Xu declares that he has no conflict of interest.
Ethical Approval
This article does not contain any studies with animals performed by any of the authors.
Informed Consent
Informed consent was obtained from all individual participants included in the study.
Additional information
Xin Zhang and Deqing Li contributed equally to this work.
Rights and permissions
About this article
Cite this article
Li, D., Zhang, X., Kong, F. et al. Molecularly Imprinted Solid-Phase Extraction Coupled with High-Performance Liquid Chromatography for the Determination of Trace Trichlorfon and Monocrotophos Residues in Fruits. Food Anal. Methods 10, 1284–1292 (2017). https://doi.org/10.1007/s12161-016-0687-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12161-016-0687-z