Isolation, chemical characterization and hydrolysis of the trichothecene 7α-hydroxy, 15-deacetylcalonectrin (3ANX) from Fusarium graminearum DAOMC 242077
Fusarium graminearum and related species produce regulated mycotoxins that contaminate important food commodities resulting in serious agricultural and animal productivity losses. F. graminearum DAOMC 242077 was isolated from soft wheat in Eastern Canada and an investigation of this strains secondary metabolites confirmed it produced the recently discovered type-A trichothecene 7α-hydroxy, 15-deacetylcalonectrin (3ANX; 1). In an effort to prepare large amounts of its deacetylated product 7α-hydroxy, 3, 15-dideacetylcalonectrin (NX; 2), F. graminearum DAOMC 242077 was grown using conditions favoring the biosynthesis of trichothecenes to enable large amounts of 3ANX (1) to be purified. The structure of 3ANX (1) was confirmed by interpretation of spectroscopic data, physical properties and LC-HRMS. A simple hydrolysis scheme was developed to convert 3ANX (1), to NX (2). The objective of this study was to generate and chemically characterize 3ANX (1) and NX (2) reference materials for the scientific community for toxicology studies, analytical method development and exposure assessments.
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Aitken, A. (Alex), Miller, JD, & McMullin, D. (2019). Isolation, chemical characterization and hydrolysis of the trichothecene 7α-hydroxy, 15-deacetylcalonectrin (3ANX) from Fusarium graminearum DAOMC 242077. Tetrahedron Letters. doi:10.1016/j.tetlet.2019.02.025