New tricks for old dogs: Two new macrocyclic trichothecene epimers and absolute configuration of 16-hydroxyverrucarin B.

Two new compounds, 3'-epi-16-hydroxyverrucarin A and 3'-epiverrucarin X, have been isolated and identified, and the characterization data of a series of known trichothecenes have been refined. The interesting structure and potent biological activities of macrocyclic trichothecenes have been of interest to the scientific community for several decades. However, some of the characterization data for the older analogues of this class are not well documented, either because of a lack of absolute configuration or a lack of clarity in the NMR data, largely due to technological limitations at the time they were discovered. NMR techniques, application of Mosher's esters analysis, and electronic circular dichroism were used here both to refine the characterization of known trichothecenes, as well as to uncover new structures. These studies demonstrate strategies that can be used to interrogate the characterization data of well-known secondary metabolites, thereby gaining greater insight into methods that can be used to refine previous literature.