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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Mycotoxin Prevention and Applied Microbiology Research » Research » Publications at this Location » Publication #308870
Title: Assessment of the electronic structure and properties of trichothecene toxins using density functional theory

Author
item Appell, Michael
item BOSMA, WAYNE - Bradley University

Submitted to: Journal of Hazardous Materials
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 1/21/2015
Publication Date: 5/15/2015
Publication URL: http://handle.nal.usda.gov/10113/60529
Citation: Appell, M., Bosma, W.B. 2015. Assessment of the electronic structure and properties of trichothecene toxins using density functional theory. Journal of Hazardous Materials. 288:113-123.

Interpretive Summary: Trichothecenes are structurally related natural products that include toxins produced by various molds, and are of concern due to potential contamination of agricultural commodities and associated food safety risks. In this research, we identified important properties of deoxynivalenol, nivalenol, T-2 toxin, and 31 other related trichothecenes using state of the art computation chemistry methods that help explain trichothecene toxicity and detection. In addition, molecular properties distinguishing type B from type A trichothecenes were identified and provide information on their mechanism of toxicity. Several computer generated structure-activity models from this study possess excellent descriptive ability and serve as inexpensive tools to evaluate potential trichothecene toxicity and false-positive detection outcomes. The results of this study are helpful to food safety scientists, toxicologists, and regulators concerned with trichothecene exposure.

Technical Abstract: A comprehensive quantum chemical study was carried out on 34 type A and type B trichothecenes, including selected derivatives and biosynthetic precursors of deoxynivalenol, nivalenol, and T-2 toxin. Quantum parameters, Natural Bond Orbital (NBO) analysis, and molecular properties were calculated on structures geometry optimized at the B3LYP/6-311+G** level. Type B trichothecenes possessed significantly larger electrophilicity index compared to the type A trichothecenes studied. Certain hydroxyls of nivalenol exhibited considerable rotation during a molecular dynamics simulation (5 picoseconds) at the B3LYP/6-31G** level in implicit aqueous solvent. Nine quantitative structure activity relationship (QSAR) models for toxicity and detection were developed using genetic algorithm, principal component, and multilinear analyses. The models suggest several 2-dimensional topological descriptors contain important information related to trichothecene cyctotoxicity, phytotoxicity, immunochemical detection, and cross-reactivity.