Abstract
The present study reports a simple and quick sample extraction method to determine bisphenol A (BPA) and 4-nonylphenol (4-NP) in fish samples. The method is based on the complete dissolution of the analytes in a deep eutectic solvent (DES), while retaining most of the biological matrices in the pretreated solids. The pretreatment was performed for 15 min using a DES composed of choline chloride–urea (ChCl–Ur), at 1:2 molar ratio, in a closed vessel at atmospheric pressure. The target analytes were extracted with low volumes of an organic solvent, purified, concentrated, and then determined by a high-performance liquid chromatography–fluorescence detector. The average extraction efficiency of the analytes reached 95% after optimizing the critical variables. The matrix-matched calibration curves were obtained in the range of 0.07–6.50 µg g−1 for BPA and 0.30–6.50 µg g−1 4-NP with R2 greater than 0.996. Limits of detection were 0.021 and 0.015 µg g−1 for BPA and 4-NP, respectively. Limits of quantifications were below 0.1 µg g−1 for the 0.15 g sample. For both analytes, the maximum intra-day and inter-day precisions did not exceed 5.5 and 12.5%, respectively. The proposed method was applied to analyze canned tuna and fresh fish tissues. The accuracy of the method was evaluated by spiking the standard analytes to real samples, and excellent results were achieved.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ademollo N, Patrolecco L, Rauseo J, Nielsen J, Corsolini S (2018) Bioaccumulation of nonylphenols and bisphenol A in the Greenland shark Somniosus microcephalus from the Greenland seawaters. Microchem J 136:106–112. https://doi.org/10.1016/j.microc.2016.11.009
Aristiawan Y, Aryana N, Putri D, Styarini D (2015) Analytical method development for bisphenol A in tuna by using high performance liquid chromatography-UV. Procedia Chem 16:202–208. https://doi.org/10.1016/j.proche.2015.12.042
Aydin F, Yilmaz E, Soylak M (2017) A simple and novel deep eutectic solvent based ultrasound-assisted emulsification liquid phase microextraction method for malachite green in farmed and ornamental aquarium fish water samples. Microchem J 132:280–285. https://doi.org/10.1016/j.microc.2017.02.014
Cunha SC, Fernandes JO (2018) Extraction techniques with deep eutectic solvents TrAC. Trends Anal Chem 105:225–239. https://doi.org/10.1016/j.trac.2018.05.001
Cunha SC, Cunha C, Ferreira AR, Fernandes JO (2012) Determination of bisphenol A and bisphenol B in canned seafood combining QuEChERS extraction with dispersive liquid–liquid microextraction followed by gas chromatography–mass spectrometry. Anal Bioanal Chem 404:2453–2463. https://doi.org/10.1007/s00216-012-6389-5
Cunha SC, Oliveira C, Fernandes JO (2017) Development of QuEChERS-based extraction and liquid chromatography-tandem mass spectrometry method for simultaneous quantification of bisphenol A and tetrabromobisphenol A in seafood: fish, bivalves, and seaweeds. Anal Bioanal Chem 409:151–160. https://doi.org/10.1007/s00216-016-9980-3
David A, Fenet H, Gomez E (2009) Alkylphenols in marine environments: distribution monitoring strategies and detection considerations. Mar Pollut Bull 58:953–960. https://doi.org/10.1016/j.marpolbul.2009.04.021
Endres F, MacFarlane D, Abbott A (2008) Electrodeposition from ionic liquids. John Wiley & Sons, Hoboken
Ferrara F, Ademollo N, Delise M, Fabietti F, Funari E (2008) Alkylphenols and their ethoxylates in seafood from the Tyrrhenian Sea. Chemosphere 72:1279–1285. https://doi.org/10.1016/j.chemosphere.2008.04.060
Florindo C, Romero L, Rintoul I, Branco LC, Marrucho IM (2018) From phase change materials to green solvents: hydrophobic low viscous fatty acid-based deep eutectic solvents. ACS Sustain Chem Eng 6:3888–3895. https://doi.org/10.1021/acssuschemeng.7b04235
Habibi E, Ghanemi K, Fallah-Mehrjardi M, Dadolahi-Sohrab A (2013) A novel digestion method based on a choline chloride–oxalic acid deep eutectic solvent for determining Cu, Fe, and Zn in fish samples. Anal Chim Acta 762:61–67
Handy S, Lavender K (2013) Organic synthesis in deep eutectic solvents: Paal-Knorr reactions. Tetrahedron Lett 54:4377–4379. https://doi.org/10.1016/j.tetlet.2013.05.122
Hayyan A, Mjalli FS, AlNashef IM, Al-Wahaibi YM, Al-Wahaibi T, Hashim MA (2013) Glucose-based deep eutectic solvents: physical properties. J Mol Liq 178:137–141. https://doi.org/10.1016/j.molliq.2012.11.025
Kang J-H, Kondo F (2005) Bisphenol A degradation in seawater is different from that in river water. Chemosphere 60:1288–1292. https://doi.org/10.1016/j.chemosphere.2005.01.058
Kim KH, Dutta T, Sun J, Simmons B, Singh S (2018) Biomass pretreatment using deep eutectic solvents from lignin derived phenols. Green Chem 20:809–815. https://doi.org/10.1039/C7GC03029K
Liao H-G, Jiang Y-X, Zhou Z-Y, Chen S-P, Sun S-G (2008) Shape-controlled synthesis of gold nanoparticles in deep eutectic solvents for studies of structure-functionality relationships in electrocatalysis. Angew Chem 120:9240–9243. https://doi.org/10.1002/ange.200803202
Morrison HG, Sun CC, Neervannan S (2009) Characterization of thermal behavior of deep eutectic solvents and their potential as drug solubilization vehicles. Int J Pharm 378:136–139
Munguía-López EM, Gerardo-Lugo S, Peralta E, Bolumen S, Soto-Valdez H (2005) Migration of bisphenol A (BPA) from can coatings into a fatty-food simulant and tuna fish. Food Addit Contam 22:892–898. https://doi.org/10.1080/02652030500163674
Pérez Bendito MD, Rubio Bravo S, Lunar Reyes ML, García Prieto A (2009) Determination of bisphenol A in canned fatty foods by coacervative microextraction, liquid chromatography and fluorimetry. Food Addit Contam Part A 26:265–274. https://doi.org/10.1080/02652030802368740
Pérez-Palacios D, Fernández-Recio MÁ, Moreta C, Tena MT (2012) Determination of bisphenol-type endocrine disrupting compounds in food-contact recycled-paper materials by focused ultrasonic solid–liquid extraction and ultra performance liquid chromatography-high resolution mass spectrometry. Talanta 99:167–174. https://doi.org/10.1016/j.talanta.2012.05.035
Ruesgas-Ramón M, Figueroa-Espinoza MC, Durand E (2017) Application of deep eutectic solvents (DES) for phenolic compounds extraction: overview, challenges, and opportunities. J Agric Food Chem 65:3591–3601. https://doi.org/10.1021/acs.jafc.7b01054
Salgueiro-González N, Turnes-Carou I, Muniategui-Lorenzo S, López-Mahía P, Prada-Rodríguez D (2012) Fast and selective pressurized liquid extraction with simultaneous in cell clean up for the analysis of alkylphenols and bisphenol A in bivalve molluscs. J Chromatogr A 1270:80–87. https://doi.org/10.1016/j.chroma.2012.11.014
Shahbaz K, Mjalli FS, Hashim MA, AlNashef IM (2011) Prediction of deep eutectic solvents densities at different temperatures. Thermochim Acta 515:67–72. https://doi.org/10.1016/j.tca.2010.12.022
Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114:11060–11082. https://doi.org/10.1021/cr300162p
Soares A, Guieysse B, Jefferson B, Cartmell E, Lester JN (2008) Nonylphenol in the environment: a critical review on occurrence, fate, toxicity and treatment in wastewaters. Environ Int 34:1033–1049. https://doi.org/10.1016/j.envint.2008.01.004
Sun F et al (2016) Recent advances and progress in the detection of bisphenol A. Anal Bioanal Chem 408:6913–6927. https://doi.org/10.1007/s00216-016-9791-6
Yilmaz E, Soylak M (2015) Ultrasound assisted-deep eutectic solvent extraction of iron from sheep, bovine and chicken liver samples. This study is a part of PhD thesis of Erkan Yilmaz Talanta 136:170–173 https://doi.org/10.1016/j.talanta.2014.12.034
Ying G-G (2006) Fate, behavior and effects of surfactants and their degradation products in the environment. Environ Int 32:417–431. https://doi.org/10.1016/j.envint.2005.07.004
Zhang Q, De Oliveira Vigier K, Royer S, Jerome F (2012) Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev 41:7108–7146. https://doi.org/10.1039/C2CS35178A
Zhou Q, Gao Y, Xie G (2011) Determination of bisphenol A, 4-n-nonylphenol, and 4-tert-octylphenol by temperature-controlled ionic liquid dispersive liquid-phase microextraction combined with high performance liquid chromatography–fluorescence detector. Talanta 85:1598–1602. https://doi.org/10.1016/j.talanta.2011.06.050
Acknowledgements
The financial and technical support provided by Khorramshahr University of Marine Science and Technology through a grant (2016) to conduct this study is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
There are no conflicts of interest to declare.
Rights and permissions
About this article
Cite this article
Noori, L., Ghanemi, K. Selective extraction of bisphenol A and 4-nonylphenol from canned tuna and marine fish tissues using choline-based deep eutectic solvents. Chem. Pap. 73, 301–308 (2019). https://doi.org/10.1007/s11696-018-0579-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-018-0579-3