Hydrogen bondings in deoxynivalenol (DON) conformations-a density functional study

Deoxynivalenol (DON) or Vomitoxin is the dominant toxin produced by Fusarium fungi, and is a tetracyclic sesquiterpenoid compound (C15H20O6). The structure of DON, containing seven stereo centers, is fully characterized. The molecule contains six oxygen atoms consisting of three alcoholic OH groups, a carbonyl, a cyclic ether and an epoxide which would allow for multiple hydrogen bondings. These possibilities were investigated quantum mechanically at the Density Functional [B3LYP/6-31G(d)] level of theory. Two functional groups of DON, a conjugated carbonyl and an epoxide may be related to its toxic effects.