Solvent and water mediated structural variations in deoxynivalenol and their potential implications on the disruption of ribosomal function

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dc.contributor.authorForoud, Nora Afsaneh
dc.contributor.authorShank, Roxanne A.
dc.contributor.authorKiss, Douglas
dc.contributor.authorEudes, François
dc.contributor.authorHazendonk, Paul
dc.date.accessioned2016-12-01T00:30:18Z
dc.date.available2016-12-01T00:30:18Z
dc.date.issued2016
dc.descriptionSherpa Romeo green journal: open accessen_US
dc.description.abstractFusarium head blight (FHB) is a disease of cereal crops caused by trichothecene producing Fusarium species. Trichothecenes, macrocylicic fungal metabolites composed of three fused rings (A–C) with one epoxidef unctionality, area class of mycotoxins known to inhibit protein synthesis in eukaryotic ribosomes. These toxins accumulate in the kernels of infected plants rendering them unsuitable for human and animal consumption. Among the four classes of trichothecenes (A–D) A and B are associated with FHB, where the type B trichothecene deoxynivalenol (DON) is most relevant. While it is known that these toxins inhibit protein synthesis by disrupting peptidyl transferase activity, the exact mechanism of this inhibition is poorly understood. The three-dimensional structures and H-bonding behavior of DON were evaluated using one-and two-dimensional nuclear magnetic resonance (NMR) spectroscopy techniques. Comparisons of the NMR structure presented here with the recently reported crystal structure of DON bound in the yeast ribosome reveal insights into the possible toxicity mechanism of this compound. The work described herein identifies a waterbinding pocket in the core structure of DON, where the 3OH plays an important role in this interaction. These results provide preliminary insights into how substitution at C3 reduces trichothecene toxicity. Further investigations along these lines will provide opportunities to develop trichothecene remediation strategies based on the disruption of water binding interactions with 3OH.en_US
dc.description.peer-reviewYesen_US
dc.identifier.citationForoud, N. A., Shank, R. A., Kiss, D., Eudes, F., & Hazendonk, P. (2016). Solvent and water mediated structural variations in deoxynivalenol and their potential implicaitons on the disruption of ribosomal function. Frontiers in Microbiology, 7(1239). doi:10.3389/fmicb.2016.01239en_US
dc.identifier.urihttps://hdl.handle.net/10133/4734
dc.language.isoen_CAen_US
dc.publisherFrontiers Mediaen_US
dc.publisher.departmentDepartment of Chemistry and Biochemistryen_US
dc.publisher.facultyArts and Scienceen_US
dc.publisher.institutionLethbridge Research and Development Centreen_US
dc.publisher.institutionUniversity of Lethbridgeen_US
dc.subjectDeoxynivalenoi (DON)en_US
dc.subjectFusarium head blighten_US
dc.subjectFusarium graminearumen_US
dc.subjectNMR spectroscopyen_US
dc.subjectMycotoxinsen_US
dc.subjectChemical structureen_US
dc.titleSolvent and water mediated structural variations in deoxynivalenol and their potential implications on the disruption of ribosomal functionen_US
dc.typeArticleen_US
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