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

A theoretical study on vomitoxin and its tautomers

“…Vomitoxin possesses two secondary and one primary alcoholic OH groups, in addition to the presence of two chemically reactive functional groups, namely a conjugated ketone and an epoxide ring. At least one, but maybe both of these functionalities can be associated with the toxic activity of deoxynivalenol [4]. As a B-type trichothecene, deoxynivalenol is soluble even in water and in polar solvents such as aqueous methanol, aqueous acetonitrile, and ethyl acetate.…”

“…As a B-type trichothecene, deoxynivalenol is soluble even in water and in polar solvents such as aqueous methanol, aqueous acetonitrile, and ethyl acetate. The 12,13-epoxy group is extremely stable to nucleophilic attack, and deoxynivalenol is stable at 120 • C and is not decomposed under mildly acidic conditions [3,4].…”

“…The occurrence of vomitoxin is associated primarily with F. graminearum (Gibberella zeae) and Fusarium culmorum, both of which are important plant pathogens which cause Fusarium head blight in wheat and Gibberella ear rot in maize [4,5]. A direct relationship between the incidence of Fusarium head blight and contamination of wheat with deoxynivalenol has been established.…”

A review of the presence of some food contaminants on the territory of the Republic of Serbia

“…It is a polar organic compound of the type B trichothecenes [66]. It is usually produced by Fusarium culmorum and Fusarium graminearum [67].The contamination of economically important cereals represents a great problem in Europe, Asia and America since it occurs in the field more frequently than in the warehouse [68].…”

Assessment of the electronic structure and properties of trichothecene toxins using density functional theory

“…DFT studies at the B3LYP/6-31G(d,p) level of theory on the tautomers of deoxynivalenol and nivalenol gave additional structural insight into tautomer preferences and the interpretation of experimental IR and physical data [16,17]. Hydrogen bonding schemes of deoxynivalenol were investigated at the B3LYP/6-31G(d) level and it was reported that the toxic effects are associated with the conjugated carbonyl and epoxide moieties [18]. Recently, pentahydroxyscirpene was isolated and the configuration of this trichothecene was determined experimentally with the support of B3LYP/6-311+G** calculations [19].…”