title: Assessment of the electronic structure and properties of trichothecene toxins using density functional theory.
abstract: A comprehensive quantum chemical study was carried out on 35 type A and B trichothecenes and biosynthetic precursors, including selected derivatives of deoxynivalenol and T-2 toxin. Quantum chemical properties, Natural Bond Orbital (NBO) analysis, and molecular parameters 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 hydroxyl groups of deoxynivalenol, nivalenol, and T-2 toxin exhibited considerable rotation during molecular dynamics simulations (5 ps) at the B3LYP/6-31G** level in implicit aqueous solvent. Quantitative structure activity relationship (QSAR) models were developed to evaluate toxicity and detection using genetic algorithm, principal component, and multilinear analyses. The models suggest electronegativity and several 2-dimensional topological descriptors contain important information related to trichothecene cytotoxicity, phytotoxicity, immunochemical detection, and cross-reactivity.
authors.affiliation: Bacterial Foodborne Pathogens and Mycology Research USDA, ARS, National Center for Agricultural Utilization Research 1815 N. University St., Peoria, IL 61604, USA. Electronic address: michael.appell@ars.usda.gov.
authors.forename: Michael
authors.initials: M
authors.lastname: Appell
authors.affiliation: Mund-Lagowski Department of Chemistry and Biochemistry Bradley University 1501 W. Bradley Ave., Peoria, IL 61625, USA. Electronic address: bosma@bumail.bradley.edu.
authors.forename: Wayne B
authors.initials: WB
authors.lastname: Bosma
mesh_terms: D004583:Electrons; D007120:Immunochemistry; D008958:Models, Molecular; D021281:Quantitative Structure-Activity Relationship; D011789:Quantum Theory; D013605:T-2 Toxin / Q000737:chemistry; D014118:Toxins, Biological / Q000737:chemistry*; D014255:Trichothecenes / Q000737:chemistry*
chemical_list: D014118:Toxins, Biological; D014255:Trichothecenes; C038405:nivalenol; D013605:T-2 Toxin; C007262:deoxynivalenol
keywords: Descriptors; Food safety; Molecular modeling; Mycotoxins; Toxicity