Cleaving Ergot Alkaloids by Hydrazinolysis—A Promising Approach for a Sum Parameter Screening Method
Ergot alkaloids are mycotoxins formed by fungi of the <i>Claviceps</i> genus, which are some of the most common contaminants of food and feed worldwide. These toxins are a structurally heterogeneous group of compounds, sharing an ergoline backbone. Six structures and their corresponding...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-05-01
|
| Series: | Toxins |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2072-6651/13/5/342 |
| _version_ | 1797534619857321984 |
|---|---|
| author | Maximilian Kuner Susanne Kühn Hajo Haase Klas Meyer Matthias Koch |
| author_facet | Maximilian Kuner Susanne Kühn Hajo Haase Klas Meyer Matthias Koch |
| author_sort | Maximilian Kuner |
| collection | DOAJ |
| description | Ergot alkaloids are mycotoxins formed by fungi of the <i>Claviceps</i> genus, which are some of the most common contaminants of food and feed worldwide. These toxins are a structurally heterogeneous group of compounds, sharing an ergoline backbone. Six structures and their corresponding stereoisomers are typically quantified by either HPLC-FLD or HPLC-MS/MS and the values subsequently summed up to determine the total ergot alkaloid content. For the development of a screening method targeting all ergot alkaloids simultaneously, the alkaloids need to be transferred to one homogeneous structure: a lysergic acid derivative. In this study, two promising cleaving methods—acidic esterification and hydrazinolysis—are compared, using dihydroergocristine as a model compound. While the acidic esterification proved to be unsuitable, due to long reaction times and oxidation sensitivity, hydrazinolysis reached a quantitative yield in 40‒60 min. Parallel workup of several samples is possible. An increasing effect on the reaction rate by the addition of ammonium iodide was demonstrated. Application of hydrazinolysis to a major ergot alkaloid mix solution showed that all ergopeptines were cleaved, but ergometrine/-inine was barely affected. Still, hydrazinolysis is a suitable tool for the development of a sum parameter screening method for ergot alkaloids in food and feed. |
| first_indexed | 2024-03-10T11:33:05Z |
| format | Article |
| id | doaj.art-c69ffb18eaa64d15b6f34eca01043273 |
| institution | Directory Open Access Journal |
| issn | 2072-6651 |
| language | English |
| last_indexed | 2024-03-10T11:33:05Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Toxins |
| spelling | doaj.art-c69ffb18eaa64d15b6f34eca010432732023-11-21T19:09:26ZengMDPI AGToxins2072-66512021-05-0113534210.3390/toxins13050342Cleaving Ergot Alkaloids by Hydrazinolysis—A Promising Approach for a Sum Parameter Screening MethodMaximilian Kuner0Susanne Kühn1Hajo Haase2Klas Meyer3Matthias Koch4Bundesanstalt für Materialforschung und-prüfung (BAM), 12205 Berlin, GermanyInstitut Kirchhoff Berlin GmbH, 13347 Berlin, GermanyDepartment of Food Chemistry and Toxicology, Technische Universität Berlin, 10623 Berlin, GermanyBundesanstalt für Materialforschung und-prüfung (BAM), 12205 Berlin, GermanyBundesanstalt für Materialforschung und-prüfung (BAM), 12205 Berlin, GermanyErgot alkaloids are mycotoxins formed by fungi of the <i>Claviceps</i> genus, which are some of the most common contaminants of food and feed worldwide. These toxins are a structurally heterogeneous group of compounds, sharing an ergoline backbone. Six structures and their corresponding stereoisomers are typically quantified by either HPLC-FLD or HPLC-MS/MS and the values subsequently summed up to determine the total ergot alkaloid content. For the development of a screening method targeting all ergot alkaloids simultaneously, the alkaloids need to be transferred to one homogeneous structure: a lysergic acid derivative. In this study, two promising cleaving methods—acidic esterification and hydrazinolysis—are compared, using dihydroergocristine as a model compound. While the acidic esterification proved to be unsuitable, due to long reaction times and oxidation sensitivity, hydrazinolysis reached a quantitative yield in 40‒60 min. Parallel workup of several samples is possible. An increasing effect on the reaction rate by the addition of ammonium iodide was demonstrated. Application of hydrazinolysis to a major ergot alkaloid mix solution showed that all ergopeptines were cleaved, but ergometrine/-inine was barely affected. Still, hydrazinolysis is a suitable tool for the development of a sum parameter screening method for ergot alkaloids in food and feed.https://www.mdpi.com/2072-6651/13/5/342ergot alkaloidssum parameter methodhydrazinolysisesterification |
| spellingShingle | Maximilian Kuner Susanne Kühn Hajo Haase Klas Meyer Matthias Koch Cleaving Ergot Alkaloids by Hydrazinolysis—A Promising Approach for a Sum Parameter Screening Method Toxins ergot alkaloids sum parameter method hydrazinolysis esterification |
| title | Cleaving Ergot Alkaloids by Hydrazinolysis—A Promising Approach for a Sum Parameter Screening Method |
| title_full | Cleaving Ergot Alkaloids by Hydrazinolysis—A Promising Approach for a Sum Parameter Screening Method |
| title_fullStr | Cleaving Ergot Alkaloids by Hydrazinolysis—A Promising Approach for a Sum Parameter Screening Method |
| title_full_unstemmed | Cleaving Ergot Alkaloids by Hydrazinolysis—A Promising Approach for a Sum Parameter Screening Method |
| title_short | Cleaving Ergot Alkaloids by Hydrazinolysis—A Promising Approach for a Sum Parameter Screening Method |
| title_sort | cleaving ergot alkaloids by hydrazinolysis a promising approach for a sum parameter screening method |
| topic | ergot alkaloids sum parameter method hydrazinolysis esterification |
| url | https://www.mdpi.com/2072-6651/13/5/342 |
| work_keys_str_mv | AT maximiliankuner cleavingergotalkaloidsbyhydrazinolysisapromisingapproachforasumparameterscreeningmethod AT susannekuhn cleavingergotalkaloidsbyhydrazinolysisapromisingapproachforasumparameterscreeningmethod AT hajohaase cleavingergotalkaloidsbyhydrazinolysisapromisingapproachforasumparameterscreeningmethod AT klasmeyer cleavingergotalkaloidsbyhydrazinolysisapromisingapproachforasumparameterscreeningmethod AT matthiaskoch cleavingergotalkaloidsbyhydrazinolysisapromisingapproachforasumparameterscreeningmethod |