deoxynivalenol-3-glucoside and 15-acetyldeoxynivalenol

This study was aimed to evaluate the fate of D3G, 3-ADON, and 15-ADON during various processing steps (milling, fermentation, baking and cooking with water) of different cereal-based products, as well as the co-occurrence of culmorin (CUL) and its derivatives (15-Hydroxy-CUL and 5-Hydroxy-CUL. Some databases such as Science Direct, PubMed, Scopus, and Embase were screened to collect the relevant published papers between January 1983 to October 2018, and 23 articles with 319 data were included. The baking resulted in reductions in the concentration of all types of investigated masked mycotoxins, i.e., 15-ADON (-25%) > 3-ADON (-15%) > D3G (-6%). Also, rank order of CUL and its derivatives based on occurrence was CUL (70%) > 15-Hydroxy-CUL (47%) > 5-Hydroxy-CUL (15%) and their rank based on their concentration was 5-Hydroxy-CUL (99.21 µg/kg) > CUL (48.84 µg/kg) > 15-Hydroxy-CUL (9.39 µg/kg) > Hydroxy -CUL (0.06 µg/kg) > 12-Hydroxy-CUL (0.05 µg/kg) > 14-Hydroxy-CUL (0.01 µg/kg).

Topics: Chromatography, High Pressure Liquid; Cooking; Databases, Factual; Edible Grain; Food Contamination; Glucosides; Mycotoxins; Sesquiterpenes; Trichothecenes

Topics: Animal Feed; Biotransformation; Chromatography, Liquid; Food Microbiology; Fusarium; Germany; Glucosides; Mass Spectrometry; Risk Assessment; Trichothecenes; Zea mays; Zearalenone; Zeranol

Contamination of wheat grains with Fusarium mycotoxins and their modified forms is an important issue in wheat industry. The objective of this study was to analyse the deoxynivalenol (DON) and deoxynivalenol-3-glucosides (D3G) content in Canadian spring wheat cultivars grown in two locations, inoculated with a mixture of 3-acetyldeoxynivalenol (3-ADON)-producing Fusarium graminearum strains and a mixture of 15-acetlyldeoxynivalenol (15-ADON)-producing F. graminearum strains. According to the analysis of variance, significant differences were observed among the cultivars for Fusarium head blight (FHB) disease index, Fusarium-damaged kernel percentage (%FDK), DON content and D3G content. When the effect of chemotype was considered, significant differences were observed for FHB disease index, FDK percentage and DON content. The D3G content and D3G/DON ratio were not significantly different between the chemotypes, except for D3G content at the Winnipeg location. The Pearson correlation coefficient between DON and D3G was 0.84 and 0.77 at Winnipeg and Carman respectively. The highest D3G/DON ratio was observed in cultivars Carberry (44%) in Carman and CDC Kernen (63.8%) in Winnipeg. The susceptible cultivars showed lower D3G/DON ratio compared with the cultivars rated as moderately resistant and intermediate. The current study indicated that Canadian spring cultivars produce D3G upon Fusarium infection.

Topics: Canada; Disease Resistance; Edible Grain; Food Contamination; Fusarium; Glucosides; Mycotoxins; Plant Diseases; Seasons; Trichothecenes; Triticum

The gastrointestinal tract is the first target after ingestion of the mycotoxin deoxynivalenol (DON) via feed and food. Deoxynivalenol is known to affect the proliferation and viability of animal and human intestinal epithelial cells. In addition to DON, feed and food is often co-contaminated with modified forms of DON, such as 3-acetyldeoxynivalenol (3ADON), 15-acetyl-deoxynivalenol (15ADON) and deoxynivalenol-3-β-D-glucoside (DON3G). The goal of this study was to determine the in vitro intrinsic cytotoxicity of these modified forms towards differentiated and proliferative porcine intestinal epithelial cells by means of flow cytometry. Cell death was assessed by dual staining with Annexin-V-fluorescein isothiocyanate (FITC) and propidium iodide (PI), which allows the discrimination of viable (FITC-/PI-), apoptotic (FITC+/PI-) and necrotic cells (FITC+/PI+). Based on the data from the presented pilot in vitro study, it is concluded that cytotoxicity for proliferative cells can be ranked as follows: DON3G ≪ 3ADON < DON≈15ADON.

Topics: Animals; Animals, Newborn; Apoptosis; Chromatography, Liquid; Epithelial Cells; Flow Cytometry; Food Contamination; Glucosides; Humans; In Vitro Techniques; Intestines; Magnetic Resonance Spectroscopy; Swine; Tandem Mass Spectrometry; Trichothecenes

A critical assessment of three previously published indirect methods based on acidic hydrolysis using superacids for the determination of "free" and "total" deoxynivalenol (DON) was carried out. The modified mycotoxins DON-3-glucoside (D3G), 3-acetyl-DON (3ADON), and 15-acetyl-DON (15ADON) were chosen as model analytes. The initial experiments focused on the stability/degradation of DON under hydrolytic conditions and the ability to release DON from the modified forms. Acidic conditions that were capable of cleaving D3G, 3ADON, and 15ADON to DON were not found, raising doubts over the efficacy of previously published indirect methods for total DON determination. Validation of these indirect methods for wheat, maize, and barley using UHPLC-MS/MS was performed in order to test the accuracy of the generated results. Validation data for DON, D3G, 3ADON, and 15ADON in nonhydrolyzed and hydrolyzed matrices were obtained. Under the tested conditions, DON was not released from D3G, 3ADON, or 15ADON after hydrolysis and thus none of the published methods were able to cleave the modified forms of DON. In addition to acids, alkaline hydrolysis with KOH for an extended time and at elevated temperatures was also tested. 3ADON and 15ADON were cleaved under the alkaline pH caused by the addition of KOH or aqueous K2CO3 to "neutralize" the acidic sample extracts in the published studies. The published additional DON increase after hydrolysis may have been caused by huge differences in matrix effects and the recovery of DON in nonhydrolyzed and hydrolyzed matrices as well as by the alkaline cleavage of 3ADON or 15ADON after the neutralization of hydrolyzed extracts.

Topics: Chromatography, Liquid; Edible Grain; Glucosides; Hordeum; Hydrolysis; Mycotoxins; Tandem Mass Spectrometry; Trichothecenes; Triticum; Zea mays

We developed a purification method based on liquid chromatography-tandem mass spectrometry for the identification of deoxynivalenol (DON), its acetylated derivatives (3-acetyl-deoxynivalenol and 15-acetyl-deoxynivalenol), and a glycosylated derivative (deoxynivalenol-3-glucoside [D3G]) in corn-based products. The analytes were extracted from samples with acetonitrile-water (85:15, vol/vol) and then purified with multifunctional columns. Evaluation of five kinds of multifunctional columns revealed that DON and its acetylated derivatives were recovered well (96 to 120%) by all columns, but D3G was recovered adequately (93.5%) by only one column, InertSep VRA-3. Samples of corn grits and corn flour were analyzed using the purification method with InertSep VRA-3. DON, D3G, and 15-acetyl-deoxynivalenol were the major contaminants in the samples harvested in 2009, but only DON was detected in the samples harvested in 2010. These results suggest that the purification method using InertSep VRA-3 is effective for identification of DON and its derivatives in corn-based products.

Topics: Acetylation; Chromatography, Liquid; Consumer Product Safety; Edible Grain; Flour; Food Contamination; Glucosides; Glycosylation; Humans; Tandem Mass Spectrometry; Trichothecenes; Zea mays

Fusarium graminearum is the most important pathogen causing Fusarium head blight (FHB) of small cereal grains worldwide responsible for quantitative and qualitative yield losses. The presence in crops is often associated with mycotoxin contamination of foodstuff limiting its use for human and animal consumption. A collection of isolates of F. graminearum from Germany was characterized genetically and chemically for their potential to produce the B trichothecenes deoxynivalenol (DON) and nivalenol (NIV). Molecular methods with eight PCR assays were implemented based on functional Tri7 and Tri13 genes and on the tri5-tri6 intergenic region to differentiate between chemotaxonomic groups DON and NIV, resulting in a marked majority (61/63) of DON chemotypes. Mycotoxins produced on rice kernels were quantified by means of LC-MSMS including DON, NIV, 3-acetyl-DON (3-ADON), 15-acetyl-DON (15-ADON), DON-3-glucoside, fusarenon X, as well as zearalenone; all of them proving to be present in high concentration among the isolates. All DON-chemotype isolates also produced lower amounts of NIV with the amount being positively correlated (R²=0.89) to the DON amount. 15-ADON and 3-ADON are reported to be produced simultaneously by the isolates, the former dominating over the latter in all but one isolate. Fungal biomass, was quantified via ergosterol amount on rice. It was used to calculate specific mycotoxin production per biomass of isolates, ranging from 0.104 to 1.815mg DON mg-1 ergosterol, presenting a Gaussian distribution. Genotype and phenotype characterization revealed discrepancies with respect to mycotoxin production potential of the fungi, i.e. isolates from one chemotype were able to produce mycotoxins from other chemotypes in considerable amounts.

Topics: DNA, Fungal; Ergosterol; Fusarium; Genotype; Germany; Glucosides; Oryza; Phenotype; Polymerase Chain Reaction; Trichothecenes; Zearalenone