deoxynivalenol-3-glucoside and deepoxy-deoxynivalenol

Deoxynivalenol (DON) is one of the most frequently occurring mycotoxins in wheat crops worldwide and poses a risk to human and animal health due to its wide range of adverse effects. Deoxynivalenol-3-glucoside (DON-3-glucoside) is a DON plant conjugate that is widely found in cereal products. As DON accumulation in the field seems unavoidable, it is important to investigate all of the conditions that affect its stability during food processing. One of the most consumed cereal product around the world is bread, however the published information about DON stability in bread shows a large variability of results because a huge amount of factors affect DON and its modified forms. So, the aim of this research was to study the fate of DON and its modified forms through the breadmaking process with the addition of xylanase and α-amylase at different fermentation temperatures. Moreover, different α-amylase and xylanase concentrations were added to the dough to be fermented. To quantify DON and its derived forms in the samples, liquid chromatography with double mass spectrophotometer was used. DON was reduced during fermentation and baking; however, the reduction at each step was related to the fermentation temperature. The presence of α-amylase and xylanase caused increases in DON during fermentation and during early baking. DON-3-glucoside was slightly reduced after fermentation and was widely increased (>80%) after baking. Deepoxy-deoxynivalenol (DOM-1) increased during the breadmaking process. Breadmaking process can reduce DON concentration, however xylanase and α-amylase presence cause increases of DON.

Topics: alpha-Amylases; Bread; Cooking; Edible Grain; Fermentation; Flour; Food Contamination; Food Handling; Food Technology; Glucosides; Hot Temperature; Mycotoxins; Trichothecenes; Triticum; Xylosidases

Deoxynivalenol (DON) is a potent mycotoxin produced by Fusarium molds and affects intestinal nutrient absorption and barrier function in experimental and farm animals. Free DON and the plant metabolite DON-3-β-d-glucoside (D3G) are frequently found in wheat and maize. D3G is stable in the upper human gut, but some human intestinal bacteria release DON from D3G in vitro. Furthermore, some bacteria derived from animal digestive systems degrade DON to a less toxic metabolite, deepoxy-deoxynivalenol (DOM-1). The metabolism of D3G and DON by the human microbiota has not been fully assessed. We therefore conducted in vitro batch culture experiments assessing the activity of the human fecal microbiota to release DON from D3G. We also studied detoxification of DON to DOM-1 by the microbiota and its potential effect on urinary DON excretion in humans. Fecal slurry from five volunteers was spiked with DON or D3G and incubated anaerobically (from 1 h to 7 days), and mycotoxins were extracted into acetonitrile. Mycotoxins were detected in fecal extracts and urine by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The fecal microbiota released DON from D3G very efficiently, with hydrolysis peaking after 4 to 6 h. The fecal microbiota from one volunteer transformed DON to DOM-1. Urine from the same volunteer also contained DOM-1 (4.7% of DON), whereas DOM-1 was not detectable in urine from other volunteers. Our results confirm that the fecal microbiota releases DON from its glycosylated form, hence increasing the toxic burden in exposed individuals. Furthermore, this is first evidence that the human fecal microbiota of one volunteer detoxifies DON, resulting in the appearance of DOM-1 in urine.

Topics: Bacteria; Chromatography, Liquid; Feces; Glucosides; Human Experimentation; Humans; Tandem Mass Spectrometry; Trichothecenes

Deoxynivalenol-3-β-D-glucoside (D3G), a plant metabolite of the Fusarium mycotoxin deoxynivalenol (DON), might be hydrolyzed in the digestive tract of mammals, thus contributing to the total dietary DON exposure of individuals. Yet, D3G has not been considered in regulatory limits set for DON for foodstuffs due to the lack of in vivo data. The aim of our study was to evaluate whether D3G is reactivated in vivo by investigation of its metabolism in rats. Six Sprague-Dawley rats received water, DON (2.0 mg/kg body weight (b.w.)) and the equimolar amount of D3G (3.1 mg/kg b.w.) by gavage on day 1, 8 and 15, respectively. Urine and feces were collected for 48 h and analyzed for D3G, DON, deoxynivalenol-glucuronide (DON-GlcA) and de-epoxy deoxynivalenol (DOM-1) by a validated LC-tandem mass spectrometry (MS/MS) based biomarker method. After administration of D3G, only 3.7±0.7% of the given dose were found in urine in the form of analyzed analytes, compared to 14.9±5.0% after administration of DON, and only 0.3±0.1% were detected in the form of urinary D3G. The majority of administered D3G was recovered as DON and DOM-1 in feces. These results suggest that D3G is little bioavailable, hydrolyzed to DON during digestion, and partially converted to DOM-1 and DON-GlcA prior to excretion. Our data indicate that D3G is of considerably lower toxicological relevance than DON, at least in rats.

Topics: Administration, Oral; Animals; Biological Availability; Biotransformation; Chromatography, High Pressure Liquid; Digestion; Feces; Glucosides; Glucuronides; Hydrolysis; Intestines; Male; Rats; Rats, Sprague-Dawley; Reproducibility of Results; Risk Assessment; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry; Trichothecenes