Skip to main content
Log in

Stability of a calibrant as certified reference material for determination of trans-zearalenone by high performance liquid chromatography-diode array detection-triple quadrupole tandem mass spectrometry

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

Abstract

In this study, a trans-zearalenone (trans-ZEN) calibrant in acetonitrile as certified reference material (CRM) was prepared and intensively investigated the stability by high performance liquid chromatography coupled diode array detection and triple quadrupole tandem mass spectrometry (HPLC–DAD-MS/MS). The photoisomerization and degradation of main component and related impurities in trans-ZEN calibrant CRM was studied in detail under different light conditions such as UV light (254 nm), sunlight, and visible light. Trans-ZEN in acetonitrile was confirmed a significant shift toward cis-ZEN up to a 52% cis-isomerization rate after exposing to UV light (254 nm) in transparent ampule for 1 day. The unsaturated double bond photosensitive groups of trans-ZEN and cis-ZEN will further undergo photoreaction to generate more isomers and related products with the increase of UV irradiation time. The calibrant in amber ampules was relatively stable after exposing to sunlight for 28 days, with only 0.35% cis-isomer observed. The results indicated that trans-ZEN solution calibrant should be packed in amber ampules to avoid UV rays. Thermal stability test exhibited this calibrant was stable over 6 weeks even at 60 °C. Trans-ZEN was found to be more stable in acetonitrile than in methanol since an unknown impurity was observed in methanol after 6 weeks placed at 25 °C. The stability study of trans-ZEN calibrant provided a basis for the usage, storage, and transportation of the CRM. A concentration and expanded uncertainty of the trans-ZEN calibrant CRM of 11.01 ± 0.18 µg/mL was developed.

Graphical abstract

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

Access this article

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

Data availability

All data and material are available.

Code availability

Not applicable.

References

  1. Binder EM, Tan LM, Chin L, Handl J, Richard J. Worldwide occurrence of mycotoxins in commodities, feeds and feed ingredients. Anim Feed Sci Tech. 2007;137:265–82.

    Article  CAS  Google Scholar 

  2. Nesic K, Ivanovic S, Nesic V. Fusarial toxins: secondary metabolites of Fusarium fungi. Rev Environ Contam Toxicol. 2014;228:101–20.

    CAS  PubMed  Google Scholar 

  3. Iqbal SZ, Selamat J. Mycotoxins in food and food products: current status. Food Safety. 2016 ;113–23.

  4. Alshannaq A, Yu JH. Occurrence, toxicity, and analysis of major mycotoxins in food. Int J Environ Res Public Health. 2017;14(6):632.

    Article  Google Scholar 

  5. National Health Commission of the PRC, GB2761–2017 of 17 March 2017 China National Food Safety Standard: maximum limit of mycotoxins in food. CFSA Data. 2017. 4.6 : 4.

  6. Commission Regulation (EC) No 1881/2006 of 19 December 2006 setting maximum levels for certain contaminants in foodstuffs. Off J Eur Union. 2006. L364 :17.

  7. Amelin VG, Karaseva NM, Tretyakov AV. Simultaneous determination of trichothecene micotoxins, ochratoxin A, and zearalenone in grain and products of its processing, feed premixes, and meat by gas chromatography. J Anal Chem. 2013;68(1):61–7.

    Article  CAS  Google Scholar 

  8. Qian M, Zhang H, Wu L, Jin N, Wang J, Jiang K. Simultaneous determination of zearalenone and its derivatives in edible vegetable oil by gel permeation chromatography and gas chromatography-triple quadrupole mass spectrometry. Food Chem. 2015;166:23–8.

    Article  CAS  Google Scholar 

  9. Rodríguez-Carrasco Y, Moltó JC, Mañes J, Berrada H. Development of microextraction techniques in combination with GC–MS/MS for the determination of mycotoxins and metabolites in human urine. J Sep Sci. 2017;40(7):1572–82.

    Article  Google Scholar 

  10. Rodríguez-Carrasco Y, Berrada H, Font G, Mañes J. Multi-mycotoxin analysis in wheat semolina using an acetonitrile-based extraction procedure and gas chromatography-tandem mass spectrometry. J Chromatogr A. 2012;1270:28–40.

    Article  Google Scholar 

  11. Wang YK, Yan YX, Mao ZW. Highly sensitive electrochemical immunoassay for zearalenone in grain and grain-based food. Microchim Acta. 2013;180(3–4):187–93.

    Article  CAS  Google Scholar 

  12. Jiang X, Li X, Yang Z, Eremin SA, Zhang X. Evaluation and optimization of three different immunoassays for rapid detection zearalenone in fodders. Food Anal Methods. 2017;10(1):256–62.

    Article  Google Scholar 

  13. Man Y, Liang G, Jia F, Li A, Fu H, Wang M, Pan L. Development of an immunochromatographic strip test for the rapid detection of alternariol monomethyl ether in fruit. Toxins. 2017;9(5):152.

    Article  Google Scholar 

  14. Li X, Li P, Zhang Q. Multi-component immunochromatographic assay for simultaneous detection of aflatoxin B1, ochratoxin A and zearalenone in agro-food. Biosens Bioelectron. 2013;49:426–32.

    Article  CAS  Google Scholar 

  15. Wu Z, Xu E, Chughtai MFJ, Jin Z, Irudayaraj J. Highly sensitive fluorescence sensing of zearalenone using a novel aptasensor based on upconverting nanoparticles. Food Chem. 2017;230:673–80.

    Article  CAS  Google Scholar 

  16. Orlov AV, Burenin AG, Massarskaya NG, Betin AV, Nikitin MP, Nikitin PI. Highly reproducible and sensitive detection of mycotoxins by label-free biosensors. Sensors and Actuators B Chem. 2016;246:1080–4.

    Article  Google Scholar 

  17. Lauren DR, Ringrose MA. Determination of the fate of three Fusarium mycotoxins through wet-milling of maize using an improved HPLC analytical technique. Food Addit Contam. 1997;14:435–43.

    Article  CAS  Google Scholar 

  18. Smyth MR, Georg C, Frischkorn B. Simultaneous determination of the trans and cis forms of zearalenone in cereal products by high performance liquid chromatography with voltametric detection. Anal Chim Acta. 1980;115:293–300.

    Article  CAS  Google Scholar 

  19. Drzymala SS, Weiz S, Heinze J. Automated solid-phase extraction coupled online with HPLC-FLD for the quantification of zearalenone in edible oil. Anal Bioanal Chem. 2015;407(12):3489–97.

    Article  CAS  Google Scholar 

  20. Tóth SB, Jolankai R, Muranyi Z, Dallos A. Analysis of deoxynivalenol, nivalenol, zearalenone in food by LC-APCI-MS. Chromatographia. 2011;73:171–4.

    Article  Google Scholar 

  21. Schuhmacher R, Berthiller F, Buttinger G, Krska R. Simultaneous determination of type A-& B-trichothecenes and zearalenone in cereals by high performance liquid chromatography-tandem mass spectrometry. Mycotoxin Res. 2005;21(4):237–40.

    Article  CAS  Google Scholar 

  22. Habler K, Gotthardt M, Schüler J, Rychlik M. Multi-mycotoxin stable isotope dilution LC–MS/MS method for Fusarium toxins in beer. Food Chem. 2017;218:447–54.

    Article  CAS  Google Scholar 

  23. Fernandes PJ, Barros N, Santo JL, Câmara JS. High-throughput analytical strategy based on modified quechers extraction and dispersive solid-phase extraction clean-up followed by liquid chromatography-triple-quadrupole tandem mass spectrometry for quantification of multiclass mycotoxins in cereals. Food Anal Methods. 2015;8(4):841–56.

    Article  Google Scholar 

  24. Zhao H, Chen X, Shen C, Qu B. Determination of 16 mycotoxins in vegetable oils using a QuEChERS method combined with high-performance liquid chromatography-tandem mass spectrometry. Food Addit ContamFig-Part A Chem Anal Control Expo Risk Assess. 2017;34(2):255–64.

    Google Scholar 

  25. Jung S-Y, Choe B-C, Choi E-J. Survey of mycotoxins in commonly consumed Korean grain products using an LC-MS/MS multimycotoxin method in combination with immunoaffinity clean-up. Food Sci Biotechnol. 2015;24(4):1193–9.

    Article  CAS  Google Scholar 

  26. Sharmili K, Jinap S, Sukor R. Development, optimization and validation of QuEChERS based liquid chromatography tandem mass spectrometry method for determination of multimycotoxin in vegetable oil. Food Control. 2016;70:152–60.

    Article  CAS  Google Scholar 

  27. Soleimany F, Jinap S, Faridah A, Khatib A. A UPLC-MS/MS for simultaneous determination of aflatoxins, ochratoxin A, zearalenone, deoxynivalenol, fumonisins, T-2 toxin and HT-2 toxin, in cereals. Food Control. 2012;25:647–53.

    Article  CAS  Google Scholar 

  28. Richardson KE, Hagler WM, Mirocha CJ. Production of zearalenone, α- and β-zearalenol, and α- and β-zearalanol by Fusarium spp. in rice culture. J Agric Food Chem. 1985;33:862–6.

    Article  CAS  Google Scholar 

  29. Muñoz L, Castro JL, Cardelle M, Castedo L, Riguera R. Acetylated mycotoxins from Fusarium graminearum. Phytochemistry. 1989;28:83–5.

    Article  Google Scholar 

  30. Peters CA. Photochemistry of zearalenone and its derivatives. J Med Chem. 1972;15(8):867–8.

    Article  CAS  Google Scholar 

  31. Miles CO, Erasmuson AF, Wilkins AL, Towers NR, Smith BL, Garthwaite I, Scahill BG, Hansen RP. Ovine metabolism of zearalenone to α-zearalanol (zeranol). J Agric Food Chem. 1996;44:3244–50.

    Article  CAS  Google Scholar 

  32. Köppen R, Riedel J, Proske M. Photochemical\trans-\cis-isomerization and quantitation of zearalenone in edible oils. J Agric Food Chem. 2012;60(47):11733–40.

    Article  Google Scholar 

  33. Ulrike B, Susane K, Hana V, Peter S, Juliane R, Sven D. UV-induced cis-trans isomerization of zearalenone in contaminated maize. Mycotoxin Res. 2013;9:221–7.

    Google Scholar 

  34. Drzymala S, Riedel J, Köppen R, Garbe LA, Koch M. Preparation of C-labelled cis-zearalenone and its application as internal standard in stable isotope dilution analysis. World Mycotoxin Journal. 2014;7(1):45–52.

    Article  CAS  Google Scholar 

  35. Josephs RD, Krska R, Macdonald S, Wilson P, Pettersson H. Production of a calibrant certified reference material for determination of the estrogenic mycotoxin zearalenone. Anal Bioanal Chem. 2004;378:1182–9.

    Article  CAS  Google Scholar 

  36. Josephs RD, Krska R, MacDonald S, Wilson P, Pettersson H. Preparation of a calibrant as certified reference material for determination of the fusarium mycotoxin zearalenone. J AOAC Int. 2003;86(1):50–60.

    CAS  PubMed  Google Scholar 

  37. International Organization for Standardization, General requirements for the competence of reference material producers. ISO 17034. ISO: Geneva; 2016.

  38. International Organization for Standardization, Reference materials guidance for characterization and assessment of homogeneity and stability. ISO Guide35.Geneva:ISO;2017.

  39. Ralf DJ, Adeline D, Magali B, Xiuqin L, Xiaomin L, Zhen G, Tiphaine C, Gustavo M, Steven W, Robert W, Hongmei L. Final report of CCQM-154a and CCOM-154a.1 key comparison study—organic solvent calibration solution gravimetric preparation and value assignment of trans-zearalenone (trans-ZEN) in acetonitrile (ACN). Metrologia. 2020;57:08019.

    Article  Google Scholar 

Download references

Acknowledgements

The authors are grateful for financial support from National Key R&D Program of China (2016YFF0201106) and thank BIPM MMCBKT project and colleagues. The authors also thank Dr Lei Zhang of Alta Scientific Co., Ltd. for the preparation of cis-ZEN pure material.

Author information

Authors and Affiliations

Authors

Contributions

Study design, data analysis, and preparation of the draft manuscript: Xiuqin Li, Shuan Liu; material procurement and conditioning: Zhen Guo, Xiaomin Li; experimental measurement: Shuan Liu, Zhen Guo, Xiaomin Li, Xianjiang Li; review of the manuscript: Qinghe Zhang, Xianjiang Li, Hui Jiao. All authors read and approved the final manuscript.

Corresponding authors

Correspondence to Xiuqin Li or Qinghe Zhang.

Ethics declarations

Ethics approval

Not applicable.

Source of biological material

Not applicable.

Statement on animal welfare

Not applicable.

Conflict of interest

The authors declare no competing interests.

Additional information

Publisher's note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 258 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, X., Liu, S., Guo, Z. et al. Stability of a calibrant as certified reference material for determination of trans-zearalenone by high performance liquid chromatography-diode array detection-triple quadrupole tandem mass spectrometry. Anal Bioanal Chem 414, 3631–3641 (2022). https://doi.org/10.1007/s00216-022-04002-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-022-04002-w

Keywords

Navigation