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Molecules 2016, 21(7), 838; doi:10.3390/molecules21070838

Chemical Synthesis of Deoxynivalenol-3-β-d-[13C6]-glucoside and Application in Stable Isotope Dilution Assays

1
Analytical Food Chemistry, Technische Universität München, Alte Akademie 10, D-85354 Freising, Germany
2
Food Chemistry and Molecular Sensory Science, Technische Universität München, Lise-Meitner-Straße 34, D-85354 Freising, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Mary Fletcher
Received: 30 May 2016 / Revised: 14 June 2016 / Accepted: 20 June 2016 / Published: 27 June 2016
(This article belongs to the Special Issue Natural Toxins)
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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-[13C6]-glucoside originated from unlabeled deoxynivalenol and [13C6]-labeled glucose. Using the synthesized isotopically-labeled standard deoxynivalenol-3-β-d-[13C6]-glucoside and the purchased labeled standard [13C15]-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. View Full-Text
Keywords: modified mycotoxin; deoxynivalenol-3-glucoside; stable isotope dilution assay; LC-MS/MS; beer; labeled standard; synthesis modified mycotoxin; deoxynivalenol-3-glucoside; stable isotope dilution assay; LC-MS/MS; beer; labeled standard; synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Habler, K.; Frank, O.; Rychlik, M. Chemical Synthesis of Deoxynivalenol-3-β-d-[13C6]-glucoside and Application in Stable Isotope Dilution Assays. Molecules 2016, 21, 838.

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