Skip to main content
SpringerLink
Log in

A novel high-performance liquid chromatography-fluorescence analysis coupled with in situ degradation-derivatization technique for quantitation of organophosphorus thioester pesticide residues in tea

  • Research Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

A novel high-performance liquid chromatography–fluorescence analysis in combination with in situ degradation–derivatization (ISD-D) technique was developed for simultaneous determination of seven organophosphorus thioester pesticides (OPTPs) in tea. The ISD-D technique was based on degradation of OPTPs by a nucleophilic substitution reaction between phenylbutane-1,2,3-trione-2-oxime and OPTPs, which can give thiol degradation products (DPs). The thiol DPs obtained were derivatized with the novel derivatization reagent N-(4-(carbazole-9-yl)-phenyl)-N-maleimide (NCPM) in a syringe. Attractively, NCPM itself did not fluoresce, whereas the derivatives of the thiol DPs fluoresced intensely, with excitation and emission maxima at 290 nm and 368 nm, respectively, which extraordinary reduced the background interference and increased the detection sensitivity for thiol DPs. Excellent linearity (R2 > 0.995) for all OPTPs was achieved, with limits of detection and limits of quantitation ranging from 0.23 to 0.45 μg/kg and from 0.75 to 1.43 μg/kg, respectively. Satisfactory recoveries ranging from 90.5% to 96.0% were obtained for all OPTPs. The ISD-D technique provided a novel and sensitive strategy for quantitation of trace amounts of OPTPs in real samples.

ᅟ

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Chen H, Gao G, Chai Y, Ma G, Hao Z, Wang C, et al. Multiresidue method for the rapid determination of pesticide residues in tea using ultra performance liquid chromatography Orbitrap high resolution mass spectrometry and in-syringe dispersive solid phase extraction. ACS Omega. 2017;2(9):5917–27.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Lu C, Liu X, Dong F, Xu J, Song W, Zhang C, et al. Simultaneous determination of pyrethrins residues in teas by ultra-performance liquid chromatography/tandem mass spectrometry. Anal Chim Acta. 2010;678(1):56–62.

    Article  CAS  PubMed  Google Scholar 

  3. Xu X-M, Yu C, Han J-L, Li J-P, El-Sepai F, Zhu A, Huang B-F, Cai Z-X, Wu H-W, Ren Y-P. Multi-residue analysis of pesticides in tea by online SEC-GC/MS. J Sep Sci. 2011;34(2):210-6.

  4. Raal A, Orav A, Püssa T, Valner C, Malmiste B, Arak E. Content of essential oil, terpenoids and polyphenols in commercial chamomile (Chamomilla recutita L. Rauschert) teas from different countries. Food Chem. 2012;131(2):632–8.

    Article  CAS  Google Scholar 

  5. Steele VE, Kelloff GJ, Balentine D, Boone CW, Mehta R, Bagheri D, Sigman CC, Zhu S, Sharma S. Comparative chemopreventive mechanisms of green tea, black tea and selected polyphenol extracts measured by in vitro bioassays. Carcinogenesis. 2000;21(1):63-7.

  6. Hamer M. The beneficial effects of tea on immune function and inflammation: a review of evidence from in vitro, animal, and human research. Nutr Res. 2007;27(7):373-9.

  7. Sharangi AB. Medicinal and therapeutic potentialities of tea (Camellia sinensis L.) – a review. Food Res Int. 2009;42(5):529–35.

    Article  CAS  Google Scholar 

  8. Shamsipur M, Yazdanfar N, Ghambarian M. Combination of solid-phase extraction with dispersive liquid–liquid microextraction followed by GC–MS for determination of pesticide residues from water, milk, honey and fruit juice. Food Chem. 2016;204:289–97.

    Article  CAS  PubMed  Google Scholar 

  9. Kamel F, Hoppin JA. Association of pesticide exposure with neurologic dysfunction and disease. Environ Health Perspect. 2004;112(9):950–8.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Pope CN. Organophosphorus pesticides: do they all have the same mechanism of toxicity? J. Toxicol Environ Health Part B. 1999;2(2):161–81.

    Article  CAS  Google Scholar 

  11. L. K. Organophosphorus poisoning and anaesthesia. Anaesthesia. 1999;54(11):1073–88.

    Article  Google Scholar 

  12. Eskenazi B, Bradman A, Castorina R. Exposures of children to organophosphate pesticides and their potential adverse health effects. Environ Health Perspect. 1999;107(Suppl 3):409–19.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Campillo N, Peñalver R, Hernández-Córdoba M. Pesticide analysis in herbal infusions by solid-phase microextraction and gas chromatography with atomic emission detection. Talanta. 2007;71(3):1417–23.

    Article  CAS  PubMed  Google Scholar 

  14. Abd El-Aty AM, Choi J-H, Rahman MM, Kim S-W, Tosun A, Shim J-H. Residues and contaminants in tea and tea infusions: a review. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2014;31(11):1794–804.

    Article  CAS  PubMed  Google Scholar 

  15. Cortés JM, Sanchez R, Díaz-Plaza EM, Villén J, Vázquez A. Large volume GC injection for the analysis of organophosphorus pesticides in vegetables using the through oven transfer adsorption desorption (TOTAD) interface. J Agric Food Chem. 2006;54(6):1997–2002.

    Article  CAS  PubMed  Google Scholar 

  16. Liu W, Hu Y, Zhao J, Xu Y, Guan Y. Determination of organophosphorus pesticides in cucumber and potato by stir bar sorptive extraction. J Chromatogr A. 2005;1095(1):1–7.

    Article  CAS  PubMed  Google Scholar 

  17. Kim N, Park I-S, Kim D-K. High-sensitivity detection for model organophosphorus and carbamate pesticide with quartz crystal microbalance-precipitation sensor. Biosens. Bioelectron. 2007;22(8):1593-9.

  18. Kuśmierek K, Chwatko G, Głowacki R, Kubalczyk P. Bald E Ultraviolet derivatization of low-molecular-mass thiols for high performance liquid chromatography and capillary electrophoresis analysis. J Chromatogr B, 307. 2011;879:1290.

  19. Cao L-W, Tan X-F, Li C, Wu C, Zhang Z-D, Deng T, et al. Capillary electrophoresis-laser induced fluorescence detection of GABA and its analogs in human serum with solid-phase extraction and fluorescein-based probes. Anal Methods. 2013;5(21):6000–8.

    Article  CAS  Google Scholar 

  20. Kumar V, Raviraju G, Rana H, Rao VK, Gupta AK. Highly selective and sensitive chromogenic detection of nerve agents (sarin, tabun and VX): a multianalyte detection approach. Chem Commun. 2017;53(96):12954–7.

    Article  CAS  Google Scholar 

  21. Chassaing C, Gonin J, Wilcox CS, Wainer IW. Determination of reduced and oxidized homocysteine and related thiols in plasma by thiol-specific pre-column derivatization and capillary electrophoresis with laser-induced fluorescence detection. J Chromatogr B. 1999;735(2):219–27.

    Article  CAS  Google Scholar 

  22. Chen X, Zhou Y, Peng X, Yoon J. Fluorescent and colorimetric probes for detection of thiols. Chem Soc Rev. 2010;39(6):2120–35.

    Article  CAS  PubMed  Google Scholar 

  23. Lv Z, Sun Z, Song C, Lu S, Chen G, You J. Sensitive and background-free determination of thiols from wastewater samples by MOF-5 extraction coupled with high-performance liquid chromatography with fluorescence detection using a novel fluorescence probe of carbazole-9-ethyl-2-maleimide. Talanta. 2016;161:228–37.

    Article  CAS  PubMed  Google Scholar 

  24. Suzukida M, Le HP SF, AR MP, Birnbaum ER, Darnall DW. Resonance energy transfer between cysteine-34 and tryptophan-214 in human serum albumin. distance measurements as a function of pH. Biochemistry. 1983;22:2415–20.

    Article  CAS  PubMed  Google Scholar 

  25. Bidari A, Ganjali MR, Norouzi P, Hosseini MR, Assadi Y. Sample preparation method for the analysis of some organophosphorus pesticides residues in tomato by ultrasound-assisted solvent extraction followed by dispersive liquid-liquid microextraction. Food Chem. 126(4):1840–4.

  26. Moinfar S, Hosseini MR. Development of dispersive liquid-liquid microextraction method for the analysis of organophosphorus pesticides in tea. J Hazard Mater. 169(1-3):907–11.

  27. Cheng Z, Dong F, Xu J, Liu X, Wu X, Chen Z, et al. Simultaneous determination of organophosphorus pesticides in fruits and vegetables using atmospheric pressure gas chromatography quadrupole-time-of-flight mass spectrometry. Food Chem. 231:365–73.

  28. Wang Q, Zhang X, Xu Z, Gao H. Simultaneous determination of three trace organophosphorus pesticide residues in vegetables using molecularly imprinted solid-phase extraction coupled with high-performance liquid chromatography. Food Anal Methods. 2015;8(8):2044–51.

    Article  Google Scholar 

  29. Seebunrueng K, Santaladchaiyakit Y, Srijaranai S. Vortex-assisted low density solvent liquid-liquid microextraction and salt-induced demulsification coupled to high performance liquid chromatography for the determination of five organophosphorus pesticide residues in fruits. Talanta. 132:769–74.

Download references

Acknowledgements

We gratefully acknowledge the financial support from the National Natural Science Foundation of China (no. 21475075) and the National Natural Science Foundation of Shandong Province (nos ZR2015CM040 and ZR2018MC031).

Author information

Authors and Affiliations

  1. Key Laboratory of Life-Organic Analysis of Shandong Province, Qufu Normal University, Qufu, 273165, Shandong, China

    Yanxin Yu, Xianzhu Luo, Xu Wang, Zhiwei Sun, Cuihua Song & Jinmao You

  2. Key Laboratory of Tibetan Medicine Research & Qinghai Key Laboratory of Qinghai-Tibet Plateau Biological Resources, Northwest Institute of Plateau Biology, Chinese Academy of Science, Xining, 810001, Qinghai, China

    Jinmao You

Authors
  1. Yanxin Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xianzhu Luo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xu Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zhiwei Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Cuihua Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jinmao You
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Cuihua Song or Jinmao You.

Ethics declarations

Conflict of interest

The authors declare that they have no competing interests.

Ethics approval

This article does not contain any studies with humans or animals performed by any of the authors.

Electronic supplementary material

ESM 1

(PDF 173 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yu, Y., Luo, X., Wang, X. et al. A novel high-performance liquid chromatography-fluorescence analysis coupled with in situ degradation-derivatization technique for quantitation of organophosphorus thioester pesticide residues in tea. Anal Bioanal Chem 410, 6911–6922 (2018). https://doi.org/10.1007/s00216-018-1294-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-018-1294-1

Keywords

Search

Navigation