Der gehörnte Roggen. Ein chemischer Blick auf den Isenheimer Altar

Streller, Sabine

doi:10.1002/ciuz.200900511

Cited by 10 publications

(2 citation statements)

References 22 publications

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“…Mycotoxins-toxic compounds formed by fungi in food and feed-have been a menace to mankind since the beginning of human sedentism and the associated agricultural crop cultivation and storage [1]. Among the various mycotoxins, ergot alkaloids play a special role, as they have been responsible for several thousands of death cases in the Middle Ages [2][3][4]. Even though the danger has been known since the 17th century [1], mass poisonings with ergot alkaloids in Europe were reported until the middle of the 20th century [5].…”

Section: Introductionmentioning

confidence: 99%

Quantification of Ergot Alkaloids via Lysergic Acid Hydrazide—Development and Comparison of a Sum Parameter Screening Method

et al. 2023

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Ergot alkaloids are a group of mycotoxins occurring in products derived from various grasses (e.g., rye) and have been regulated in the EU recently. The new maximum levels refer to the sum of the six most common ergot alkaloids in their two stereoisomeric forms in different food matrices. Typically, these twelve compounds are individually quantified via HPLC-MS/MS or -FLD and subsequently summed up to evaluate food safety in a time-consuming process. Since all these structures share the same ergoline backbone, we developed a novel sum parameter method (SPM) targeting all ergot alkaloids simultaneously via lysergic acid hydrazide. After extraction and clean-up, in analogy to the current European standard method EN 17425 (ESM) for ergot alkaloid quantitation, the samples were derivatized by an optimized hydrazinolysis protocol, which allowed quantitative conversion after 20 min at 100 °C. The new SPM was evaluated against another established HPLC-FLD-based method (LFGB) and the HPLC-MS/MS-based ESM using six naturally contaminated rye and wheat matrix reference materials. While the SPM provided comparable values to the ESM, LFGB showed deviating results. Determined recovery rates, limits of detection and quantification of all three employed methods confirm that the new SPM is a promising alternative to the classical approaches for ergot alkaloid screening in food.

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Section: Introductionmentioning

confidence: 99%

Quantification of Ergot Alkaloids via Lysergic Acid Hydrazide—Development and Comparison of a Sum Parameter Screening Method

et al. 2023

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“…During the infestation, sclerotia—the wintering body of the fungus—are formed, which contain the toxic ergot alkaloids in varying concentrations [ 3 ]. Claviceps fungi and the corresponding alkaloids have played an important role since the Middle Ages, leading to tens of thousands of deaths [ 4 , 5 ]. When ingested continuously, ergot alkaloids can cause two types of disease: the gangrenous or the convulsive type of ergotism, either one eventually resulting in death [ 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

Cleaving Ergot Alkaloids by Hydrazinolysis—A Promising Approach for a Sum Parameter Screening Method

Kuner

Kühn

Haase

et al. 2021

Toxins

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Ergot alkaloids are mycotoxins formed by fungi of the Claviceps 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.

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Der Rote Keulenkopf

Petersen

2023

Chemie in nserer Zeit

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Zusammenfassung1935 isolierten der englische Chemiker Harold Ward Dudley und der schottische Frauenarzt John Chassar Moir das hochpotente, uterotone Ergometrin aus den Sklerotien des Roten Keulenkopfs. Forscherteams in England und den USA zeigten, dass alle damals bekannten Ergotalkaloide einen identischen Baustein besitzen, die Lysergsäure. Die neuen Erkenntnisse motivierten den Schweizer Naturstoffforscher Albert Hofmann dazu, die medizinalchemische und pharmakologische Lysergsäureforschung bei der Sandoz AG zu beginnen. Er arbeitete erstmalig eine synthetische Route von der Lysergsäure zum Ergometrin aus und entdeckte dabei das Methylergometrin. 1946 erhielt der neue Wirkstoff die Zulassung als Uterotonikum und für die Behandlung der Nachgeburtsblutungen. Auf der Suche nach einem Kreislaufstimulans synthetisierte Hofmann das Lysergsäurediethylamid (LSD), dessen psychotrope Eigenschaften er zufällig entdeckte. LSD belebte die Diskussion in der Psychiatrie aufs Neue, ob nicht körpereigene „Giftstoffe“ die Ursache einer Schizophrenie sein könnten. Der Nachweis des 5‐Hydroxytryptamins im Gehirn von Wirbeltieren und dessen Fähigkeit, die psychotogene Aktivität des LSD zu antagonisieren, deckten die chemischen Grundlagen der Psyche und ihrer Erkrankungen auf. Dieser Zusammenhang eröffnete die neuartige therapeutische Option, niedermolekulare Verbindungen zur Behandlung psychischer Störungen zu entwickeln. Als am Weizmann‐Institut in Israel die Hemmung der Prolaktinsekretion durch Ergotoxin entdeckt wurde, entschieden sich die Sandoz AG in Basel, das italienische Pharmaunternehmen Farmitalia und eine tschechische Arbeitsgruppe zu Wirkstoffentwicklungsprogrammen, aus denen die neue Arzneimittelklasse der spezifischen Dopamin‐D2‐Rezeptoragonisten hervorging. 1975 erhielt die Sandoz AG die Zulassung für 2‐Bromo‐α‐Ergokryptin zur Behandlung der Parkinson‐Krankheit sowie der weiblichen Infertilität, der Akromegalie und weiterer Erkrankungen, die durch Prolaktin‐ beziehungsweise Wachstumshormon‐sezernierende Hypophysenadenome hervorgerufen werden.

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Der gehörnte Roggen. Ein chemischer Blick auf den Isenheimer Altar

Cited by 10 publications

References 22 publications

Quantification of Ergot Alkaloids via Lysergic Acid Hydrazide—Development and Comparison of a Sum Parameter Screening Method

Quantification of Ergot Alkaloids via Lysergic Acid Hydrazide—Development and Comparison of a Sum Parameter Screening Method

Cleaving Ergot Alkaloids by Hydrazinolysis—A Promising Approach for a Sum Parameter Screening Method

Der Rote Keulenkopf

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