A theoretical study on vomitoxin and its tautomers

Türker, Lemi; Gümüş, Selçuk

doi:10.1016/j.jhazmat.2008.06.087

Cited by 21 publications

(10 citation statements)

References 26 publications

(31 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This reaction occurred nonenzymatically, especially at high pH, which does not exclude the possibility that GSH conjugate formation is enzyme catalyzed in vivo. Putative structures of adducts formed with DON and its tautomers (Türker and Gümüs 2009) (e.g., iso-DON) consistent with the NMR results are shown in Figure 7. Potentially, the products with two GSH added may exist.…”

Section: The Potential Role Of Gsh In Don Resistancesupporting

confidence: 76%

Transcriptome Analysis of the Barley–Deoxynivalenol Interaction: Evidence for a Role of Glutathione in Deoxynivalenol Detoxification

Gardiner¹,

Boddu²,

Berthiller³

et al. 2010

MPMI

145

135

View full text Add to dashboard Cite

Trichothecenes are a major group of toxins produced by phytopathogenic fungi, including Fusarium graminearum. Trichothecenes inhibit protein synthesis in eukaryotic cells and are toxicologically relevant mycotoxins for humans and animals. Because they promote plant disease, the role of host responses to trichothecene accumulation is considered to be an important aspect of plant defense and resistance to fungal infection. Our overall objective was to examine the barley response to application of the type B trichothecene deoxynivalenol (DON). We found that DON is diluted by movement from the application site to acropetal and basipetal florets. A susceptible barley genotype converted DON to DON-3-O-glucoside, indicating that UDP-glucosyltransferases capable of detoxifying DON must exist in barley. RNA profiling of DON-treated barley spikes revealed strong upregulation of gene transcripts encoding ABC transporters, UDP-glucosyltransferases, cytochrome P450s, and glutathione-S-transferases. We noted that transcripts encoding cysteine synthases were dramatically induced by DON, and that toxin-sensitive yeast on glutathione- or cysteine-supplemented media or carrying a gene that encodes a cysteine biosynthetic enzyme exhibit DON resistance, suggesting that preventing glutathione depletion by increasing cysteine supply could play a role in ameliorating the impact of DON. Evidence for nonenzymatic formation of DON-glutathione adducts in vitro was found using both liquid chromatography-mass spectrometry and nuclear magnetic resonance analysis, indicating that the formation of DON-glutathione conjugates in vivo may reduce the impact of trichothecenes. Our results indicate that barley exhibits multiple defense mechanisms against trichothecenes.

show abstract

Section: The Potential Role Of Gsh In Don Resistancesupporting

confidence: 76%

Transcriptome Analysis of the Barley–Deoxynivalenol Interaction: Evidence for a Role of Glutathione in Deoxynivalenol Detoxification

Gardiner¹,

Boddu²,

Berthiller³

et al. 2010

MPMI

145

135

View full text Add to dashboard Cite

show abstract

“…Type B trichothecenes possess a carbonyl in the R5 position and include compounds 1-10, and 29. This study also includes the type A trichothecene T-2 toxin and related compounds (11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28). T-2 toxin is associated with a variety of harmful effects, including alimentary toxic aleukia, and is a possible war agent [1].…”

Section: General Considerationsmentioning

confidence: 99%

“…Density functional studies have provided important information on toxin structures [10][11][12][13][14][15]; however, these methods have only been applied to a few trichothecene toxins. 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].…”

Section: Introductionmentioning

confidence: 99%

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

Appell

Bosma

2015

Journal of Hazardous Materials

View full text Add to dashboard Cite

“…B3LYP density functional methods have provided insight into the structures patulin and related mycotoxins, and we applied this hybrid functional for the single molecule studies of patulin and proposed patulin-propylthiol adducts at the 6-31G(d,p) level [24][25][26]. Geometry optimization was performed in the gas phase using B3LYP/6-31G(d,p) level of theory on delocalized internal coordinates using the Eigenvector Following Algorithm with the convergence criteria set at 1 × 10 −6 Hartree and a gradient of less than 3 × 10 −4 a.u.…”

Section: Molecular Modelingmentioning

confidence: 99%