Charge-solvated versus protonated salt forms of cyclodepsipeptide toxins in electrospray: Dissociation of alkali-cationized forms enables straightforward sequencing of cereulide.

Autor: Liuu S; Staphylococcus, Bacillus & Clostridium (SBCL) unit, Laboratory for Food Safety, French Agency for Food, Environmental and Occupational Health & Safety (ANSES), Université Paris-Est, Maisons-Alfort, France., Trinh KE; Pesticides and Marine Biotoxins (PBM) unit, Laboratory for Food Safety, French Agency for Food, Environmental and Occupational Health & Safety (ANSES), Université Paris-Est, Maisons-Alfort, France., Darii E; Génomique Métabolique, Genoscope, Institut François Jacob, CEA, CNRS, Univ Evry, Université Paris-Saclay, Evry, France., Cao C; Université Paris Saclay, CEA-INRAE, Laboratoire Innovations en Spectrométrie de Masse pour la Santé (LI-MS), DRF/Institut Joliot/DMTS/SPI, MetaboHUB, CEA Saclay, Gif-sur-Yvette, France., Damont A; Université Paris Saclay, CEA-INRAE, Laboratoire Innovations en Spectrométrie de Masse pour la Santé (LI-MS), DRF/Institut Joliot/DMTS/SPI, MetaboHUB, CEA Saclay, Gif-sur-Yvette, France., Gimbert Y; Faculté des Sciences et de l'Ingénierie, Institut Parisien de Chimie Moléculaire (IPCM), Sorbonne Université, Paris, France.; Département de Chimie Moléculaire, UMR CNRS 5250, Université Grenoble Alpes, Grenoble, France., Fenaille F; Université Paris Saclay, CEA-INRAE, Laboratoire Innovations en Spectrométrie de Masse pour la Santé (LI-MS), DRF/Institut Joliot/DMTS/SPI, MetaboHUB, CEA Saclay, Gif-sur-Yvette, France., Makni Y; Pesticides and Marine Biotoxins (PBM) unit, Laboratory for Food Safety, French Agency for Food, Environmental and Occupational Health & Safety (ANSES), Université Paris-Est, Maisons-Alfort, France., Inthavong C; Pesticides and Marine Biotoxins (PBM) unit, Laboratory for Food Safety, French Agency for Food, Environmental and Occupational Health & Safety (ANSES), Université Paris-Est, Maisons-Alfort, France., Lavison-Bompard G; Pesticides and Marine Biotoxins (PBM) unit, Laboratory for Food Safety, French Agency for Food, Environmental and Occupational Health & Safety (ANSES), Université Paris-Est, Maisons-Alfort, France., Hennekinne JA; Staphylococcus, Bacillus & Clostridium (SBCL) unit, Laboratory for Food Safety, French Agency for Food, Environmental and Occupational Health & Safety (ANSES), Université Paris-Est, Maisons-Alfort, France., Firmesse O; Staphylococcus, Bacillus & Clostridium (SBCL) unit, Laboratory for Food Safety, French Agency for Food, Environmental and Occupational Health & Safety (ANSES), Université Paris-Est, Maisons-Alfort, France., Tabet JC; Université Paris Saclay, CEA-INRAE, Laboratoire Innovations en Spectrométrie de Masse pour la Santé (LI-MS), DRF/Institut Joliot/DMTS/SPI, MetaboHUB, CEA Saclay, Gif-sur-Yvette, France.; Faculté des Sciences et de l'Ingénierie, Institut Parisien de Chimie Moléculaire (IPCM), Sorbonne Université, Paris, France.
Jazyk: angličtina
Zdroj: Journal of mass spectrometry : JMS [J Mass Spectrom] 2024 Jun; Vol. 59 (6), pp. e5037.
DOI: 10.1002/jms.5037
Abstrakt: Bacillus cereus is responsible for foodborne outbreaks worldwide. Among the produced toxins, cereulide induces nausea and vomiting after 30 min to 6 h following the consumption of contaminated foods. Cereulide, a cyclodepsipeptide, is an ionophore selective to K + in solution. In electrospray, the selectivity is reduced as [M + Li] + ; [M + Na] + and [M + NH 4 ] + can also be detected without adding corresponding salts. Two forms are possible for alkali-cationized ions: charge-solvated (CS) that exclusively dissociates by releasing a bare alkali ion and protonated salt (PS), yielding alkali product ions by covalent bond cleavages (CBC) promoted by mobile proton. Based on a modified peptide cleavage nomenclature, the PS product ion series (b, a, [b + H 2 O] and [b + C n H 2n O] [n = 4, 5]) are produced by Na + /Li + /K + -cationized cereulide species that specifically open at ester linkages followed by proton mobilization promoting competitive ester CBC as evidenced under resonant collision activation. What is more, unlike the sodiated or lithiated cereulide, which regenerates little or no alkali cation, the potassiated forms lead to an abundant K + regeneration. This occurs by splitting of (i) the potassiated CS forms with an appearance threshold close to that of the PS first fragment ion generation and (ii) eight to four potassiated residue product ions from the PS forms. Since from Na + /Li + -cationized cereulide, (i) the negligible Na + /Li + regeneration results in a higher sensibility than that of potassiated forms that abundantly releasing K + , and (ii) a better sequence recovering, the use of Na + (or Li + ) should be more pertinent to sequence isocereulides and other cyclodepsipeptides.
(© 2024 The Authors. Journal of Mass Spectrometry published by John Wiley & Sons Ltd.)
Databáze: MEDLINE
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