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Degradation and epimerization of ergot alkaloids after baking and in vitro digestion

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Abstract

The degradation and epimerization of ergot alkaloids (EAs) in rye flour were investigated after baking cookies and subsequently subjecting them to an in vitro digestion model. Different steps of digestion were analyzed using salivary, gastric, and duodenal juices. The degradation and bidirectional conversion of the toxicologically relevant (R)-epimers and the biologically inactive (S)-epimers for seven pairs of EAs were determined by a HPLC method coupled with fluorescence detection. Baking cookies resulted in degradation of EAs (2–30 %) and a shift in the epimeric ratio toward the (S)-epimer for all EAs. The applied digestion model led to a selective toxification of ergotamine and ergosine, two ergotamine-type EAs. The initial percentage of the toxic (R)-epimer in relation to the total toxin content was considerably increased after digestion of cookies. Ergotamine and ergosine increased from 32 to 51 % and 35 to 55 %, respectively. In contrast, EAs of the ergotoxine type (ergocornine, α- and β-ergocryptine, and ergocristine) showed an epimeric shift toward their biologically inactive (S)-epimers. Further experiments indicated that the selective epimerization of ergotamine EAs occurs in the duodenal juice only. These results demonstrate that toxification of EAs in the intestinal tract should be taken into consideration.

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Source of funding

All work was financed by BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Str. 11, 12489 Berlin, Germany. There was no external financial support.

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There are no conflicts of interest.

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Authors and Affiliations

  1. Federal Institute for Materials Research and Testing, Richard-Willstätter-Str. 11, 12489, Berlin, Germany

    Stefan Merkel, Ronald Maul, Robert Köppen, Matthias Koch & Irene Nehls

  2. Department of Biology, Chemistry and Pharmacy, Freie Universität Berlin, Takustr. 3, 14195, Berlin, Germany

    Baha Dib

Authors
  1. Stefan Merkel
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  2. Baha Dib
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  3. Ronald Maul
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  4. Robert Köppen
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  5. Matthias Koch
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  6. Irene Nehls
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Correspondence to Stefan Merkel.

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Merkel, S., Dib, B., Maul, R. et al. Degradation and epimerization of ergot alkaloids after baking and in vitro digestion. Anal Bioanal Chem 404, 2489–2497 (2012). https://doi.org/10.1007/s00216-012-6386-8

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  • DOI: https://doi.org/10.1007/s00216-012-6386-8

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