Production of high quantities of 3-acetyldeoxynivalenol and deoxynivalenol

Altpeter, Fredy; Posselt, U. K.

doi:10.1007/bf00212246

Cited by 25 publications

(21 citation statements)

References 11 publications

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“…Water was purified by reverse osmosis using an ELGA Purelab Ultra-AN-MK2 system (Veolia Water, Vienna, Austria). DON (purity >98 %) was produced and purified according to Altpeter and Posselt ( 1994 ). Internal standards ( 2 H 8 -valine, 2 H 4 -succinic acid, 13 C 6 -glucose, nonadecanoic acid methylester (NONA)), as well as formic acid (MS grade), chloroform, pyridine and methoxyamine hydrochloride (MOX) were purchased from Sigma Aldrich (Vienna, Austria), N-methyl-N-trimethylsilyl trifluoroacetamide (MSTFA) from Wagner Munz (Vienna, Austria).…”

Section: Methodsmentioning

confidence: 99%

GC–MS based targeted metabolic profiling identifies changes in the wheat metabolome following deoxynivalenol treatment

et al. 2014

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Fusariumgraminearum and related species commonly infest grains causing the devastating plant disease Fusarium head blight (FHB) and the formation of trichothecene mycotoxins. The most relevant toxin is deoxynivalenol (DON), which acts as a virulence factor of the pathogen. FHB is difficult to control and resistance to this disease is a polygenic trait, mainly mediated by the quantitative trait loci (QTL) Fhb1 and Qfhs.ifa-5A. In this study we established a targeted GC–MS based metabolomics workflow comprising a standardized experimental setup for growth, treatment and sampling of wheat ears and subsequent GC–MS analysis followed by data processing and evaluation of QC measures using tailored statistical and bioinformatics tools. This workflow was applied to wheat samples of six genotypes with varying levels of Fusarium resistance, treated with either DON or water, and harvested 0, 12, 24, 48 and 96 h after treatment. The results suggest that the primary carbohydrate metabolism and transport, the citric acid cycle and the primary nitrogen metabolism of wheat are clearly affected by DON treatment. Most importantly significantly elevated levels of amino acids and derived amines were observed. In particular, the concentrations of the three aromatic amino acids phenylalanine, tyrosine, and tryptophan increased. No clear QTL specific difference in the response could be observed except a generally faster increase in shikimate pathway intermediates in genotypes containing Fhb1. The overall workflow proved to be feasible and facilitated to obtain a more comprehensive picture on the effect of DON on the central metabolism of wheat.Electronic supplementary materialThe online version of this article (doi:10.1007/s11306-014-0731-1) contains supplementary material, which is available to authorized users.

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Section: Methodsmentioning

confidence: 99%

GC–MS based targeted metabolic profiling identifies changes in the wheat metabolome following deoxynivalenol treatment

et al. 2014

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“…For the animal trials, DON was produced in vitro from cultures of F. graminearum in accordance to the protocol described by Altpeter et al [31] (Romer Labs, Tulln, Austria), and was mixed into the experimental feed.…”

Section: Methodsmentioning

confidence: 99%

The Mycotoxin Deoxynivalenol Predisposes for the Development of Clostridium perfringens-Induced Necrotic Enteritis in Broiler Chickens

et al. 2014

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Both mycotoxin contamination of feed and Clostridium perfringens-induced necrotic enteritis have an increasing global economic impact on poultry production. Especially the Fusarium mycotoxin deoxynivalenol (DON) is a common feed contaminant. This study aimed at examining the predisposing effect of DON on the development of necrotic enteritis in broiler chickens. An experimental Clostridium perfringens infection study revealed that DON, at a contamination level of 3,000 to 4,000 µg/kg feed, increased the percentage of birds with subclinical necrotic enteritis from 20±2.6% to 47±3.0% (P<0.001). DON significantly reduced the transepithelial electrical resistance in duodenal segments (P<0.001) and decreased duodenal villus height (P = 0.014) indicating intestinal barrier disruption and intestinal epithelial damage, respectively. This may lead to an increased permeability of the intestinal epithelium and decreased absorption of dietary proteins. Protein analysis of duodenal content indeed showed that DON contamination resulted in a significant increase in total protein concentration (P = 0.023). Furthermore, DON had no effect on in vitro growth, alpha toxin production and netB toxin transcription of Clostridium perfringens. In conclusion, feed contamination with DON at concentrations below the European maximum guidance level of 5,000 µg/kg feed, is a predisposing factor for the development of necrotic enteritis in broilers. These results are associated with a negative effect of DON on the intestinal barrier function and increased intestinal protein availability, which may stimulate growth and toxin production of Clostridium perfringens.

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“…1 ) were synthesized using a sulfuryl imidazolium salt as described by Fruhmann et al [ 16 ]. D3G and DON for analytical purpose were purchased from Romer Labs Diagnostic GmbH (Tulln, Austria), whereas DON for the treatment of plants was produced and purified according to Altpeter and Posselt [ 17 ]. Solid substances were dissolved in pure methanol (D3S, D15S) or acetonitrile (DON, D3G) and stored at −20 °C.…”

Section: Methodsmentioning

confidence: 99%

Deoxynivalenol-sulfates: identification and quantification of novel conjugated (masked) mycotoxins in wheat

et al. 2014

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We report the identification of deoxynivalenol-3-sulfate and deoxynivalenol-15-sulfate as two novel metabolites of the trichothecene mycotoxin deoxynivalenol in wheat. Wheat ears which were either artificially infected with Fusarium graminearum or directly treated with the major Fusarium toxin deoxynivalenol (DON) were sampled 96 h after treatment. Reference standards, which have been chemically synthesized and confirmed by NMR, were used to establish a liquid chromatography-electrospray ionization (LC-ESI)-MS/MS-based “dilute and shoot” method for the detection, unambiguous identification, and quantification of both sulfate conjugates in wheat extracts. Using this approach, detection limits of 0.003 mg/kg for deoxynivalenol-3-sulfate and 0.002 mg/kg for deoxynivalenol-15-sulfate were achieved. Matrix-matched calibration was used for the quantification of DON-sulfates in the investigated samples. In DON-treated samples, DON-3-sulfate was detected in the range of 0.29–1.4 mg/kg fresh weight while DON-15-sulfate concentrations were significantly lower (range 0.015–0.061 mg/kg fresh weight). In Fusarium-infected wheat samples, DON-3-sulfate was the only detected sulfate conjugate (range 0.022–0.059 mg/kg fresh weight). These results clearly demonstrate the potential of wheat to form sulfate conjugates of DON. In order to test whether sulfation is a detoxification reaction in planta, we determined the ability of the sulfated DON derivatives to inhibit in vitro protein synthesis of wheat ribosomes. The results demonstrate that both DON-sulfates can be regarded as detoxification products. DON-15-sulfate was about 44× less inhibitory than the native toxin, and no toxicity was observed for DON-3-sulfate in the tested range.Graphical abstractᅟElectronic supplementary materialThe online version of this article (doi:10.1007/s00216-014-8340-4) contains supplementary material, which is available to authorized users.

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Production of high quantities of 3-acetyldeoxynivalenol and deoxynivalenol

Cited by 25 publications

References 11 publications

GC–MS based targeted metabolic profiling identifies changes in the wheat metabolome following deoxynivalenol treatment

GC–MS based targeted metabolic profiling identifies changes in the wheat metabolome following deoxynivalenol treatment

The Mycotoxin Deoxynivalenol Predisposes for the Development of Clostridium perfringens-Induced Necrotic Enteritis in Broiler Chickens

Deoxynivalenol-sulfates: identification and quantification of novel conjugated (masked) mycotoxins in wheat

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