Chemical synthesis of deoxynivalenol-3-β-D-[13 C6 ]-glucoside and application in stable isotope dilution assays

Katharina Habler, Oliver Frank, Michael Rychlik

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Modified mycotoxins have been gaining importance in recent years and present a certain challenge in LC-MS/MS analysis. Due to the previous lack of a labeled isotopologue of the modified mycotoxin deoxynivalenol-3-glucoside, in our study we synthesized the first 13C-labeled internal standard. Therefore, we used the Königs-Knorr method to synthesize deoxynivalenol-3-β-D-[13 C6 ]-glucoside originated from unlabeled deoxynivalenol and [13 C6 ]-labeled glucose. Using the synthesized isotopically-labeled standard deoxynivalenol-3-β-D-[13 C6 ]-glucoside and the purchased labeled standard [13 C15 ]-deoxynivalenol, a stable isotope dilution LC-MS/MS method was firstly developed for deoxynivalenol-3-glucoside and deoxynivalenol in beer. The preparation and purification of beer samples was based on a solid phase extraction. The validation data of the newly developed method gave satisfying results. Intra- and interday precision studies revealed relative standard deviations below 0.5% and 7%, respectively. The recoveries ranged for both analytes between 97% and 112%. The stable isotope dilution assay was applied to various beer samples from four different countries. In summary, deoxynivalenol-3-glucoside and deoxynivalenol mostly appeared together in varying molar ratios but were quantified in rather low contents in the investigated beers.

Original languageEnglish
Article number838
JournalMolecules
Volume21
Issue number7
DOIs
StatePublished - Jul 2016

Keywords

  • Beer
  • Deoxynivalenol-3-glucoside
  • LC-MS/MS
  • Labeled standard
  • Modified mycotoxin
  • Stable isotope dilution assay
  • Synthesis

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