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Open AccessArticle

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

AMA 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(7):838.

Chicago/Turabian Style

Habler, Katharina; Frank, Oliver; Rychlik, Michael. 2016. "Chemical Synthesis of Deoxynivalenol-3-β-d-[13C6]-glucoside and Application in Stable Isotope Dilution Assays" Molecules 21, no. 7: 838.

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