Occasionally, agricultural commodities are contaminated with molds capable of producing structurally related trichothecene metabolites at levels associated with food safety risks. A comprehensive study on 34 trichothecene mycotoxins and biosynthetic precursors was conducted using density functional theory and Quantitative Structure-Activity Relationships (QSAR) to develop economical tools to evaluate toxicity and false-positive detection results. Distinct differences between Type A and B trichothecenes are observed in frontier orbital properties obtained at the B3LYP/6-311+G(d,p) level with Type B trichothecenes possessing significantly larger electrophilicity index compared to type A trichothecenes. B3LYP/6-31G(d,p) density functional molecular dynamics simulations on deoxynivalenol, nivalenol, and T-2 toxin using the COSMO implicit water solvent suggest intramolecular interactions remain significant in water. QSAR models were developed using 1- and 2-dimensional descriptors to describe cytotoxicity, phytotoxicity, and detection cross-reactivity. Important descriptors of toxicity and immunochemical detection models include spatial autocorrelation indices (Moran and Geary) and Burden matrices.

QSAR and density functional approaches to evaluate trichothecene toxicity and detection

249th National Meeting (2015)

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