Analysis of glutathione adducts of patulin by means of liquid chromatography (HPLC) with biochemical detection (BCD) and electrospray ionization tandem mass spectrometry (ESI-MS/MS) |
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Authors: | Nils Helge Schebb Helene Faber Ronald Maul Ferry Heus Jeroen Kool Hubertus Irth Uwe Karst |
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Affiliation: | 1. Institut für Anorganische und Analytische Chemie, Westf?lische Wilhelms-Universit?t Münster, Corrensstra?e 30, 48149, Münster, Germany 2. Center for Cardiovascular Research (CCR), Institut für Pharmakologie, Charité-Universit?tsmedizin Berlin, Hessische Stra?e 3-4, 10115, Berlin, Germany 3. Department of Chemistry and Pharmaceutical Sciences, Section Analytical Chemistry & Applied Spectroscopy, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV, Amsterdam, The Netherlands
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Abstract: | Abstract A novel method for the identification of glutathione/electrophile adducts that are inhibiting glutathione-S-transferase (GST) activity was developed and applied for the analysis of the mycotoxin patulin. The method is based on high-performance liquid chromatography (HPLC) coupled to a continuous-flow enzyme reactor serving as biochemical detector (BCD) in parallel to electrospray mass spectrometric detection (ESI-MS). This HPLC-BCD technique combines a separation step and the detection of the inhibition and is therefore ideally suited for the analysis of the activity of single patulin/glutathione adducts within a complex mixture of adducts. Two out of at least 15 detected patulin–glutathione adducts showed strong GST inhibition. In ESI-MS, the inhibitory active adducts were characterized by [M + H]+ ions with m/z 462.1138 and m/z 741.2011, respectively. They could be identified as a dihydropyranone adduct containing one molecule glutathione and a ketohexanoic acid bearing two glutathione molecules. Graphical Abstract OnlineAbstractFigure Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users. |
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Keywords: | HPLC-BCD Patulin– glutathione adducts Glutathione-S-transferase inhibition ESI(+)-MS/MS Fragmentation reactions |
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