Skip to main content
SpringerLink
Log in

Automated online solid-phase extraction of albendazole and its metabolites in Chinese mitten crabs followed by stable isotope dilution UPLC–MS/MS analysis

  • Original Paper
  • Published:
European Food Research and Technology Aims and scope Submit manuscript

Abstract

The determination of albendazole (ABZ) and its metabolites, albendazole sulfoxide, albendazole sulfone, and albendazole 2-aminosulfone in crab tissue is a complex analysis involving the extraction of trace levels of potentially unstable analytes from a solid matrix. Here, we report on an online solid-phase extraction (SPE) for automated trapping of ABZ and its metabolites in Chinese mitten crab, Eriocheir sinensis H. Milne Edwards (E. sinensis), followed by stable isotope dilution UPLC–MS/MS analysis. The performance of online SPE was fully validated. Good linearity was obtained with correlation coefficients >0.99. In the analytical range, the intra-day and inter-day precision and accuracies (RSD %) were 1.44–4.62 and 3.28–6.93 %, respectively. The mean recoveries were in the range of 78.2–109.3 %. All these demonstrated that the online SPE is an excellent technique for trapping and purification of ABZ and its metabolites in crab tissue samples. Finally, this online SPE–UPLC–MS/MS strategy was successfully applied to analyze the crude extracts from several crab tissue samples.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Hymanson Z, Wang J, Sasaki T (1999) Lessons from the home of the Chinese mitten crab. IEP Newsl 12:25–32

    Google Scholar 

  2. Chen DW, Zhang M, Shrestha S (2007) Compositional characteristics and nutritional quality of Chinese mitten crab (Eriocheir sinensis). Food Chem 103:1343–1349

    Article  CAS  Google Scholar 

  3. Yang WL, Zhang GH (2005) Current trends of aquaculture production and sustainable development of Chinese mitten crab, Eriocheir sinensis. Chin J Freshw Fish 35:62–64

    Google Scholar 

  4. Takayanagui OM (2004) Therapy for neurocysticercosis. Expert Rev Neurother 4:129–139

    Article  CAS  Google Scholar 

  5. Code of Federal Regulations, Title 21; Food and Drugs; U.S. Government Printing Office: Washington, DC, 2010; part 520, sections 1192–1195; parts 522.1192 and 556.344

  6. Bueno MJM, Hernando MD, Agüera A, Fernández-Alba AR (2009) Application of passive sampling devices for screening of micro-pollutants in marine aquaculture using LC–MS/MS. Talanta 77:1518–1527

    Article  Google Scholar 

  7. Wolstenholme AJ, Fairweather I, Prichard R, Samson-Himmelstjerna G, Sangstere NC (2004) Drug resistance in veterinary helminthes. Trends Parasitol 20:469–476

    Article  CAS  Google Scholar 

  8. Albonico M, Engels D, Savioli L (2004) Monitoring drug efficacy and early detection of drug resistance in human soil-transmitted nematodes: a pressing public health agenda for helminth control. Int J Parasitol 34:1205–1210

    Article  CAS  Google Scholar 

  9. Fletouris DJ, Papapanagiotou EP, Nakos DS, Psomas IE (2008) Highly sensitive ion pair liquid chromatographic determination of albendazole marker residue in animal tissues. J Agric Food Chem 53:893–898

    Article  Google Scholar 

  10. Belaz KRA, Denadai M, Almeida AP, Lima RT, Vasconcelos MH, Pinto MM, Cass QB, Oliveira RV (2012) Enantiomeric resolution of albendazole sulfoxide by semipreparative HPLC and in vitro study of growth inhibitory effects on human cancer cell lines. J Pharm Biomed Anal 66:100–108

    Article  CAS  Google Scholar 

  11. Shaikh B, Rummel N, Reimschuessel R (2003) Determination of albendazole and its major metabolites in the muscle tissues of atlantic salmon, tilapia, and rainbow trout by high performance liquid chromatography with fluorometric detection. J Agric Food Chem 51:3254–3259

    Article  CAS  Google Scholar 

  12. Hu X, Wang J, Feng Y (2010) Determination of benzimidazole residues in edible animal food by polymer monolith microextraction combined with liquid chromatography–mass spectrometry. J Agric Food Chem 58:112–119

    Article  CAS  Google Scholar 

  13. Shaikh B, Rummel N, Yu D, Gieseker C, Evans E, Hasbrouck N, Reimschuessel R (2012) Marker residue determination of tritium-labeled ivermectin in the muscle of aquacultured largemouth bass, hybrid striped bass, and yellow perch following oral treatment. J Agric Food Chem 60:4465–4470

    Article  CAS  Google Scholar 

  14. Guo L, Deng Q, Fang G, Gao W, Wang S (2011) Preparation and evaluation of molecularly imprinted ionic liquids polymer as sorbent for on-line solid-phase extraction of chlorsulfuron in environmental water samples. J Chromatogr A 1218:6271–6277

    Article  CAS  Google Scholar 

  15. Llorca M, Farré M, Picó Y, Barceló D (2011) Analysis of perfluorinated compounds in sewage sludge by pressurized solvent extraction followed by liquid chromatography–mass spectrometry. J Chromatogr A 1218:4840–4846

    Article  CAS  Google Scholar 

  16. Blasco C, Vazquez-Roig P, Onghena M, Masia A, Picó Y (2011) Analysis of insecticides in honey by liquid chromatography–ion trap-mass spectrometry: comparison of different extraction procedures. J Chromatogr A 1218:4892–4901

    Article  CAS  Google Scholar 

  17. Vazquez-Roig P, Andreu V, Onghena M, Blasco C, Picó Y (2011) Assessment of the occurrence and distribution of pharmaceuticals in a Mediterranean wetland (L’Albufera, Valencia, Spain) by LC-MS/MS. Anal Bioanal Chem 400:1287–1301

    Article  CAS  Google Scholar 

  18. de Jong WHA, Smit R, Bakker SJL, de Vries EGE, Kema IP (2009) Plasma tryptophan, kynurenine and 3-hydroxykynurenine measurement using automated on-line solid-phase extraction HPLC–tandem mass spectrometry. J Chromatogr B 877:603–609

    Article  Google Scholar 

  19. Kinsella B, Lehotay SJ, Mastovska K, Lightfield AR, Furey A, Danaher M (2009) New method for the analysis of flukicide and other anthelmintic residues in bovine milk and liver using liquid chromatography–tandem mass spectrometry. Anal Chim Acta 637:196–207

    Article  CAS  Google Scholar 

  20. Rychlik M, Asam S (2008) Stable isotope dilution assays in mycotoxin analysis. Anal Bioanal Chem 390:617–628

    Article  CAS  Google Scholar 

  21. Ciccimaro E, Blair IA (2010) Stable-isotope dilution LC–MS for quantitative biomarker analysis. Bioanalysis 2:311–341

    Article  CAS  Google Scholar 

  22. He J, Wang S, Fang G, Zhu H, Zhang Y (2008) Molecularly imprinted polymer online solid-phase extraction coupled with high-performance liquid chromatography–UV for the determination of three sulfonamides in pork and chicken. J Agric Food Chem 56:2919–2925

    Article  CAS  Google Scholar 

  23. Dai B, Cao M, Fang G, Liu B, Dong X, Pan M, Wang S (2012) Schiff base-chitosan grafted multiwalled carbon nanotubes as a novel solid-phase extraction adsorbent for determination of heavy metal by ICP-MS. J Hazard Mater 219–220:103–110

    Article  Google Scholar 

  24. Fang G, Chen W, Yao Y, Wang J, Qin J, Wang S (2012) Multi-residue determination of organophosphorus and organochlorine pesticides in environmental samples using solid-phase extraction with cigarette filter followed by gas chromatography–mass spectrometry. J Sep Sci 35:534–540

    Article  CAS  Google Scholar 

  25. Wang S, Xu Z, Fang G, Duan Z, 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

    Article  CAS  Google Scholar 

  26. Duan Z, Fang G, Pan M, Yi J, Fan L, Liu W, Wang S (2011) Simultaneous determination of five quinoxaline-1,4-dioxides and two major metabolites in surface water by on-line solid phase extraction coupled to high-performance liquid chromatography. Anal Methods 3:1821–1827

    Article  CAS  Google Scholar 

  27. Niu Y, Zhang J, Wu Y, Shao B (2012) Analysis of bisphenol A and alkylphenols in cereals by automated on-line solid-phase extraction and liquid chromatography tandem mass spectrometry. J Agric Food Chem 60:6116–6122

    Article  CAS  Google Scholar 

  28. Zhang X, Xu H, Zhang H, Guo Y, Dai Z, Chen X (2011) Simultaneous determination of albendazole and its metabolites in fish muscle tissue by stable isotope dilution ultra-performance liquid chromatography tandem mass spectrometry. Anal Bioanal Chem 401:727–734

    Article  CAS  Google Scholar 

  29. Regueiro J, Martín-Morales E, Álvarez G, Blanco J (2011) Sensitive determination of domoic acid in shellfish by on-line coupling of weak anion exchange solid-phase extraction and liquid chromatography–diode array detection–tandem mass spectrometry. Food Chem 129:672–678

    Article  CAS  Google Scholar 

  30. Regueiro J, Rossignoli AE, Álvarez G, Blanco J (2011) Automated on-line solid-phase extraction coupled to liquid chromatography–tandem mass spectrometry for determination of lipophilic marine toxins in shellfish. Food Chem 129:533–540

    Article  CAS  Google Scholar 

  31. Xie R, Wen J, Wei H, Fan G, Zhang D (2010) High-throughput determination of faropenem in human plasma and urine by on-line solid-phase extraction coupled to high-performance liquid chromatography with UV detection and its application to the pharmacokinetic study. J Pharm Biomed Anal 52:114–121

    Article  CAS  Google Scholar 

  32. Liu L, Liu K, Wen Y, Zhang H, Lu Y, Yin Z (2012) Development of a fully automated on-line solid phase extraction and high-performance liquid chromatography with diode array detection method for the pharmacokinetic evaluation of bavachinin: a study on absolute bioavailability and dose proportionality. J Chromatogr B 893–894:21–28

    Google Scholar 

  33. Kantiani L, Farre M, Sibum M, Postigo C, de Alda ML, Barcelo D (2009) Fully automated analysis of β-lactams in bovine milk by online solid phase extraction-liquid chromatography-electrospray-tandem mass spectrometry. Anal Chem 81:4285–4429

    Article  CAS  Google Scholar 

  34. Shen Q, Lu Y, Dai Z (2010) Rapid determination of caffeoylquinic acid derivatives in Cynara scolymus L. by ultra-fast liquid chromatography/tandem mass spectrometry based on a fused core C18 column. J Sep Sci 33:3152–3158

    Article  CAS  Google Scholar 

  35. Kantiania L, Farréa M, Barceló D (2011) Rapid residue analysis of fluoroquinolones in raw bovine milk by online solid phase extraction followed by liquid chromatography coupled to tandem mass spectrometry. J Chromatogr A 1218:9019–9027

    Article  Google Scholar 

  36. García-Galán MJ, Garrido T, Fraile J, Ginebreda A, Díaz-Cruz MS, Barcel D (2011) Application of fully automated online solid phase extraction-liquid chromatography-electrospray-tandem mass spectrometry for the determination of sulfonamides and their acetylated metabolites in groundwater. Anal Bioanal Chem 399:795–806

    Article  Google Scholar 

  37. Gomez MJ, Petrovic M, Fernandez-Alba AR, Barceló D (2006) Determination of pharmaceuticals of various therapeutic classes by solid-phase extraction and liquid chromatography–tandem mass spectrometry analysis in hospital effluent wastewaters. J Chromatogr A 1114:224–233

    Article  CAS  Google Scholar 

  38. Blonk MI, van der Nagel BC, Smit LS, Mathot RAA (2010) Quantification of levetiracetam in plasma of neonates by ultra performance liquid chromatography–tandem mass spectrometry. J Chromatogr B 878:675–681

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This study was supported by Major Scientific and Technological Specialized Project of Zhejiang Province (2009C02002) and Key Innovation Team Support Project of Zhejiang Province (2009R50031). Both Qing Shen and Wei Dong thank the SGS committee of City University of Hong Kong for granting them a PhD studentship and partial financial supports from a RGC grant (Grant No. 7002872) for the purchase of consumable materials.

Conflict of interest

None.

Compliance with Ethics Requirements

This article does not contain any studies with human or animal subjects.

Author information

Authors and Affiliations

  1. Department of Biology and Chemistry, City University of Hong Kong, Tat Chee Avenue, Kowloon, Hong Kong SAR, China

    Qing Shen, Wei Dong, Yixuan Wang & Hon-Yeung Cheung

  2. Institute of Aquatic Products Processing, Zhejiang Gongshang University, Hangzhou, 310000, China

    Qing Shen, Yixuan Wang, Zitong Zhu, Like Gong, Zhiyuan Dai & Hong Zhang

  3. The Entry-Exit Inspection and Quarantine Bureau of Quzhou, Quzhou, 324000, China

    Zitong Zhu

  4. Hangzhou Center for Disease Control and Prevention, Hangzhou, 310000, China

    Like Gong

Authors
  1. Qing Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wei Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yixuan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zitong Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Like Gong
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Zhiyuan Dai
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Hong Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Hon-Yeung Cheung
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hon-Yeung Cheung.

Additional information

Qing Shen and Wei Dong contributed equally to this work.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shen, Q., Dong, W., Wang, Y. et al. Automated online solid-phase extraction of albendazole and its metabolites in Chinese mitten crabs followed by stable isotope dilution UPLC–MS/MS analysis. Eur Food Res Technol 236, 919–929 (2013). https://doi.org/10.1007/s00217-013-1952-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00217-013-1952-7

Keywords

Search

Navigation