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Open AccessArticle

Structure Revision of Isocereulide A, an Isoform of the Food Poisoning Emetic Bacillus cereus Toxin Cereulide

1
Food Chemistry and Molecular Sensory Science, Technical University of Munich, Lise-Meitner-Str. 34, 85354 Freising, Germany
2
Institute of Microbiology, Department of Pathobiology, University of Veterinary Medicine Vienna, Veterinärplatz 1, 1210 Vienna, Austria
*
Author to whom correspondence should be addressed.
Academic Editors: Elisa Ovidi and Antonio Tiezzi
Molecules 2021, 26(5), 1360; https://doi.org/10.3390/molecules26051360
Received: 11 February 2021 / Revised: 25 February 2021 / Accepted: 26 February 2021 / Published: 4 March 2021
The emetic Bacillus cereus toxin cereulide presents an enormous safety hazard in the food industry, inducing emesis and nausea after the consumption of contaminated foods. Additional to cereulide itself, seven structurally related isoforms, namely the isocereulides A–G, have already been elucidated in their chemical structure and could further be identified in B. cereus contaminated food samples. The newly performed isolation of isocereulide A allowed, for the first time, 1D- and 2D-NMR spectroscopy of a biosynthetically produced isocereulide, revealing results that contradict previous assumptions of an l-O-Leu moiety within its chemical structure. By furthermore applying posthydrolytical dipeptide analysis, amino acid and α-hydroxy acid analysis by means of UPLC-ESI-TOF-MS, as well as MSn sequencing, the structure of previously reported isocereulide A could be corrected. Instead of the l-O-Leu as assumed to date, one l-O-Ile unit could be verified in the cyclic dodecadepsipeptide, revising the structure of isocereulide A to [(d-O-Leu-d-Ala-l-O-Val-l-Val)2(d-O-Leu-d-Ala-l-O-Ile-l-Val)]. View Full-Text
Keywords: B. cereus; isocereulide(s); structure elucidation; UPLC-MS; NMR spectroscopy; MSn sequencing B. cereus; isocereulide(s); structure elucidation; UPLC-MS; NMR spectroscopy; MSn sequencing
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MDPI and ACS Style

Walser, V.; Kranzler, M.; Ehling-Schulz, M.; Stark, T.D.; Hofmann, T.F. Structure Revision of Isocereulide A, an Isoform of the Food Poisoning Emetic Bacillus cereus Toxin Cereulide. Molecules 2021, 26, 1360. https://doi.org/10.3390/molecules26051360

AMA Style

Walser V, Kranzler M, Ehling-Schulz M, Stark TD, Hofmann TF. Structure Revision of Isocereulide A, an Isoform of the Food Poisoning Emetic Bacillus cereus Toxin Cereulide. Molecules. 2021; 26(5):1360. https://doi.org/10.3390/molecules26051360

Chicago/Turabian Style

Walser, Veronika; Kranzler, Markus; Ehling-Schulz, Monika; Stark, Timo D.; Hofmann, Thomas F. 2021. "Structure Revision of Isocereulide A, an Isoform of the Food Poisoning Emetic Bacillus cereus Toxin Cereulide" Molecules 26, no. 5: 1360. https://doi.org/10.3390/molecules26051360

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