Abstract
A precise analytical method based on QuEChERS has been proposed for the concurrent determination of 11 polyhalogenated carbazoles (PHCZs), benzocarbazole (BZCZ), and 9H-carbazoles (CZ). The quantification was confirmed by gas chromatography using triple quadrupole tandem mass spectrometry (Shimadzu GC–MS/MS-TQ8040) and gas chromatography coupled mass spectrometry (Agilent 7890A-5973 GC–MS). The developed method was validated by testing the following parameters: linearity, instrument limit of detection (LOD), instrument limit of quantification (LOQ), method limit of detection (MLD), method limit of quantification (MLQ), matrix effect (ME), accuracy, and precision. All compounds showed good linearity in the range of 0.005–0.2 μg/mL with correlation coefficients higher than 0.992. The method demonstrated satisfactory recoveries (ranging from 71.21 to 105.04%) for most of the compounds with relative standard deviation precision (RSD) < 10.46%, except 3-BCZ (Recovery = 67.53%, RSD = 2.83%). The values of LOD and LOQ varied from 0.05 to 0.24 ng and 0.14 to 0.92 ng, respectively, while those of MLD and MLQ ranged from 0.02 to 0.12 ng/g wet weight (ww) and 0.07 to 0.45 ng/g ww, respectively. The developed method represents a reliable tool for the routine analysis of PHCZ congeners in invertebrate animals.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Data availability
The datasets analyzed during the current study are available from the corresponding author on reasonable request.
References
Anastassiades M, Lehotay SJ, Štajnbaher D, Schenck FJ (2003) Fast and easy multiresidue method employing acetonitrile extraction/partitioning and “dispersive solid-phase extraction” for the determination of pesticide residues in produce. J AOAC Int 86(2):412–431. https://doi.org/10.1093/jaoac/86.2.412
Castillo M, González C, Miralles A (2011) An evaluation method for determination of non-polar pesticide residues in animal fat samples by using dispersive solid-phase extraction clean-up and GC-MS. Anal Bioanal Chem 400(5):1315–1328. https://doi.org/10.1007/s00216-011-4656-5
Chamkasem N, Lee S, Harmon T (2016) Analysis of 19 PCB congeners in catfish tissue using a modified QuEChERS method with GC-MS/MS. Food Chem 192:900–906. https://doi.org/10.1016/j.foodchem.2015.07.088
Chen WL, Xie Z, Wolschke H, Gandrass J, Kötke D, Winkelmann M, Ebinghaus R (2016) Quantitative determination of ultra-trace carbazoles in sediments in the coastal environment. Chemosphere 150:586–595. https://doi.org/10.1016/j.chemosphere.2016.02.051
Cunha SC, Lehotay SJ, Mastocska K, Fernandes JO, Beatriz M, Oliveira PP (2007) Evaluation of the QuEChERS sample preparation approach for the analysis of pesticide residues in olives. J Sep Sci 30:620–632. https://doi.org/10.1002/jssc.200600410
Deng Z, Hu S, Tang L, Jiang L, He J, Shen K, Xu Y, Jiang R, Li T, Chen C, Chen B, Zhou H, Zhang D, Chen J (2023) Zhang C (2023) Carbazole and polyhalogenated carbazoles in the marine environment around the Zhoushan Archipelago: distribution characteristics, environmental behavior, and sources. J Hazard Mater 442:129999. https://doi.org/10.1016/j.jhazmat.2022.129999
Fang L, Qiu F, Li Y, Wang S, DeGuzman J, Wang J (2019) She J (2019) Determination of carbazole and halogenated carbazoles in human serum samples using GC-MS/MS. Ecotoxicol Environ Safe 184:109609. https://doi.org/10.1016/j.ecoenv.2019.109609
Grigoriadou A, Schwarzbauer J (2011) Non-target screening of organic contaminants in sediments from the industrial coastal area of Kavala city (NE Greece). Water Air Soil Poll 214:623–643. https://doi.org/10.1007/s11270-010-0451-8
Guo J, Chen D, Potter D, Rockne KJ, Sturchio NC, Giesy JP, Li A (2014) Polyhalogenated carbazoles in sediments of Lake Michigan: a new discovery. Environ Sci Technol 48(21):12807–12815. https://doi.org/10.1021/es503936u
Guo C, Wang M, Xiao H, Huai B, Wang F, Pan G, Liao X, Liu Y (2016) Development of a modified QuEChERS method for the determination of veterinary antibiotics in swine manure by liquid chromatography tandem mass spectrometry. J Chromatogr B 1027:110–118. https://doi.org/10.1016/j.jchromb.2016.05.034
Hu H, Zhao M, Guo Y, Zhou Y, Li T, Zhu W, Jin H (2022) Occurrence, bioaccumulation and potential risk of polyhalogenated carbazoles in marine organisms from the East China Sea. Sci Total Environ 807:150643. https://doi.org/10.1016/j.scitotenv.2021.150643
Jones KC, Voogt P (1999) Persistent organic pollutants (POPs): state of the science. Environ Pollut 100(1–3):209–221. https://doi.org/10.1016/S0269-7491(99)00098-6
Kim L, Lee D, Cho HK, Choi SD (2019) Review of the QuEChERS method for the analysis of organic pollutants: persistent organic pollutants, polycyclic aromatic hydrocarbons, and pharmaceuticals. Trends Environ Anal Chem 22:e00063. https://doi.org/10.1016/j.teac.2019.e00063
Koesukwiwat U, Lehotay SJ, Mastovska K, Dorweiler KJ, Leepipatpiboon N (2010) Extension of the QuEChERS method for pesticide residues in cereals to flaxseeds, peanuts, and doughs. J Agric Food Chem 58(10):5950–5958. https://doi.org/10.1021/jf902988b
Lehotay SJ, Maštovská K, Yun SJ (2005) Evaluation of two fast and easy methods for pesticide residue analysis in fatty food matrixes. J AOAC Int 88(2):630–638. https://doi.org/10.1093/jaoac/88.2.630
Li H, Yin J, Liu Y, Shang J (2012) Effect of protein on the detection of fluoroquinolone residues in fish meat. Agric Food Chem 60(7):1722–1727. https://doi.org/10.1021/jf2034658
Lin KD, Chen YQ, Yuan DX (2016) Environmental behaviors and ecotoxicology of the emerging contaminants polyhalogenated carbazoles. J Environ Sci 37(4):1576–1583. https://doi.org/10.13227/j.hjkx.2016.04.050
Lu T, Chen FW (2012) Multiwfn: a multifunctional wavefunction analyzer. J Comput Chem 33:580–592. https://doi.org/10.1002/jcc.22885
Luzardo OP, Ruiz-Suárez N, Almeida-González M, Henríquez-Hernández LA, Zumbado M, Boada LD (2013) Multi-residue method for the determination of 57 persistent organic pollutants in human milk and colostrum using a QuEChERS-based extraction procedure. Anal Bioanal Chem 405(29):9523–9536. https://doi.org/10.1007/s00216-013-7377-0
Mantzos N, Karakitsou A, Zioris I, Leneti E, Konstantinou I (2013) QuEChERS and solid phase extraction methods for the determination of energy crop pesticides in soil, plant and runoff water matrices. Int J Environ Anal Chem 93(15):1566–1584. https://doi.org/10.1080/03067319.2013.803282
Mocak J, Bond AM, Mitchell S, Scollary G (1997) A statistical overview of standard (IUPAC and ACS) and new procedures for determining the limits of detection and quantification: application and voltametric and stripping techniques. Pure Appl Chem 69(2):297–328. https://doi.org/10.1351/pac199769020297
Monbaliu S, Van Poucke C, Van Peteghem C, Van Poucke K, Heungens K, De Saeger S (2009) Development of a multi-mycotoxin liquid chromatography/tandem mass spectrometry method for sweet pepper analysis. Rapid Commun Mass Sp 23(1):3–11. https://doi.org/10.1002/rcm.3833
Musyoka SN, Liti DM, Ogello F, Waidbacher H (2019) Utilization of the earthworm, Eisenia fetida (Savigny, 1826) as an alternative protein source in fish deeds processing: a review. Aquac Res 50:2301–2315. https://doi.org/10.1111/are.14091
Peng H, Chen C, Cantin J, Saunders DMV, Sun J, Tang S, Codling G, Hecker M, Wiseman S, Jones PD, Li A, Rockne KJ, Sturchio NC, Cai M, Giesy JP (2016) Untargeted screening and distribution of organo-iodine compounds in sediments from Lake Michigan and the Arctic Ocean. Environ Sci Technol 50(18):10097–10105. https://doi.org/10.1021/acs.est.6b03221
Perestrelo R, Silva P, Porto-Figueira P, Pereira JAM, Silva C, Medina S, Câmara JS (2019) QuEChERS - Fundamentals, relevant improvements, applications and future trends. Anal Chim Acta 1070:1–28. https://doi.org/10.1016/j.aca.2019.02.036
Reid BJ, Jones KC, Semple KT (2000) Bioavailability of persistent organic pollutants in soils and sediments—a perspective on mechanisms, consequences and assessment. Environ Pollut 108(1):103–112. https://doi.org/10.1016/S0269-7491(99)00206-7
Reischl A, Joneck M, Dumler-Gradl R (2005) Chlorocarbazoles in soils. Umweltwiss Schadst-Forsch 17(4):197–200. https://doi.org/10.1065/uwsf2005.10.105
Riddell N, Jin UH, Safe S, Cheng Y, Chittim B, Konstantinov A, Parette R, Pena-Abaurrea M, Reiner EJ, Poirier D, Stefanac T, McAlees AJ, McCrindle R (2015) Characterization and biological potency of mono- to tetra-halogenated carbazoles. Environ Sci Technol 49(17):10658–10666. https://doi.org/10.1021/acs.est.5b02751
Rutkowska M, Falandysz J, Saba M, Szefer P, Misztal-Szkudlińska M, Konieczka P (2022) A method for the ananlysis of methylmercury and total Hg in fungal matrices. Appl Microbiol Biot 106:5261–5272. https://doi.org/10.1007/s00253-022-12043-5
Smith WL, College C, Maine W (1977) Selective solubility: “Like disolves like.” J Chem Edu 54(4):228–229. https://doi.org/10.1021/ed054p228.2
Socas-Rodríguez B, González-Sálamo J, Herrera-Herrera AV, Hernández-Borges J, Rodríguez-Delgado M (2017) Recent advances and developments in the QuEChERS method. Compr Anal Chem 76:319–374. https://doi.org/10.1016/bs.coac.2017.01.008
Su Q, Li CJ, Dong MF, Liu XC, Zhong D, Zhou SS (2023) Soil to earthworm bioaccumulation of polyhalogenated carbazoles and related compounds: Lab and field tests. Environ Pollut 316(1):120475. https://doi.org/10.1016/j.envpol.2022.120475
Sun Y, Zheng M, Yang L, Jin R, Lin B, Li C, Liu G (2022) Progress of congener specific analysis of polyhalogenated carbazoles in the environment. Trends Anal Chem 157:116755. https://doi.org/10.1016/j.trac.2022.116755
Sun Y, Yang L, Zheng M, Weber R, Falandysz J, Lammel G, Zhao C, Chen C, Yang Q, Liu GR (2023) Industrial source identification of polyhalogenated carbazoles and preliminary assessment of their global emissions. Nat Commun 14:3740. https://doi.org/10.1038/s41467-023-39491-5
Vázquez PP, Lozano A, Uclés S, Ramos MMG, Fernández-Alba AR (2015) A sensitive and efficient method for routine pesticide multiresidue analysis in bee pollen samples using gas and liquid chromatography coupled to tandem mass spectrometry. J Chromatogr A 1426:161–173. https://doi.org/10.1016/j.chroma.2015.11.081
Vudathala D, Cummings M, Murphy L (2010) Analysis of multiple anticoagulant rodenticides in animal blood and liver tissue using principles of QuEChERS method. J Anal Toxicol 34(5):273–279. https://doi.org/10.1093/jat/34.5.273
Walorczyk S (2014) Validation and use of a QuEChERS-based gas chrogatographic-tandem mass sepectrometric method for multiresidure pesticide analysis in blackcurrants including stidues of matrix effects and estimation of measurement uncertainty. Talanta 120:106–113. https://doi.org/10.1016/j.talanta.2013.11.087
Wang PC, Lee RJ, Chen CY, Chou CC, Lee MR (2012) Determination of cyromazine and melamine in chicken eggs using quick, easy, cheap, effective, rugged and safe (QuEChERS) extraction coupled with liquid chromatographyetandem mass spectrometry. Anal Chim Acta 752:78–86. https://doi.org/10.1016/j.aca.2012.09.029
Wu Y, Tan H, Sutton R, Chen D (2017) From sediment to top predators: broad exposure of polyhalogenated carbazoles in San Francisco Bay (U.S.A.). Environ Sci Technol 51(4):2038–2046. https://doi.org/10.1021/acs.est.6b05733
Wu Y, Tan H, Zhou C, Crimmins BS, Holsen TM, Chen D (2018) Bioaccumulation and spatiotemporal trends of polyhalogenated carbazoles in Great Lakes Fish from 2004 to 2016. Environ Sci Technol 52(8):4536–4545. https://doi.org/10.1021/acs.est.8b00427
Yogendrarajah P, Van Poucke C, De Meulenaer B, De Saeger S (2013) Development and validation of a QuEChERS based liquid chromatography tandem mass spectrometry method for the determination of multiple mycotoxins in spices. J Chromatogr A 1297:1–11. https://doi.org/10.1016/j.chroma.2013.04.075
Zhou W, Huang X, Lin K (2019) Analysis of polyhalogenated carbazoles in sediment using liquid chromatography–tandem mass spectrometry. Ecotox Environ Safe 170:148–155. https://doi.org/10.1016/j.ecoenv.2018.11.131
Funding
This work was supported by the National Natural Foundation of China (Nos. 42207458 and 41877494).
Author information
Authors and Affiliations
Contributions
Chaojie Li designed the experiment and collected the dataset. Qi Su did all of the theoretical calculation and response to the reviewers’ comments. Chaojie Li and Qi Su contributed equally to this work. Juan Wu helped review and edit the manuscript. Xinmei Zhou, Dan Zhong, and Xincheng Liu did part of the experiment. Shanshan Zhou is the supervisor and wrote the original draft.
Corresponding author
Ethics declarations
Ethical approval
Not applicable.
Consent to participate
Not applicable.
Consent for publication
Written consent was sought from each author to publish the manuscript.
Competing interests
The authors declare no competing interests.
Additional information
Responsible Editor: Ester Heath
Publisher's note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Li, C., Su, Q., Wu, J. et al. Analysis of polyhalogenated carbazoles and two related compounds in earthworms using a modified QuEChERS method with GC/MS and GC/MS/MS. Environ Sci Pollut Res 30, 86255–86267 (2023). https://doi.org/10.1007/s11356-023-28535-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11356-023-28535-4