Synthesis of deoxynivalenol-3-ß-D-O-glucuronide for its use as biomarker for dietary deoxynivalenol exposure

Fruhmann, Philipp; Warth, Benedikt; Hametner, Christian; Berthiller, Franz; Horkel, Ernst; Adam, Gerhard; Sulyok, Michael; Krska, Rudolf; Fröhlich, Johannes

doi:10.3920/wmj2011.1366

Cited by 40 publications

(27 citation statements)

References 12 publications

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“…Standard solutions of DON, de-epoxy-DON (DOM), ZEA and α-zearalenol were purchased from Romer Labs (Tulln, Austria). Standards of DON-3-glucuronide, DON-3-sulphate, ZEA-glucuronide and α-zearalenol glucuronide were synthesised as described previously (Fruhmann et al 2012(Fruhmann et al , 2014Mikula et al 2012Mikula et al , 2013.…”

Section: Animals Materials and Methodsmentioning

confidence: 99%

Urinary deoxynivalenol (DON) and zearalenone (ZEA) as biomarkers of DON and ZEA exposure of pigs

et al. 2016

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Four diets contaminated with 1.1 to 5.0 mg/kg deoxynivalenol (DON) and 0.4 to 2.4 mg/kg zearalenone (ZEA) were fed to four groups of six growing Large White pigs. Urine samples were collected after 3 to 4 days and again after 6 to 7 days on the diets. On each sampling day, half of the animals were sampled in the morning, after an 8-h fast, and the other half were sampled in the afternoon, after 7 h of ad libitum access to feed. The urinary concentrations of DON, DON-glucuronide, DON-3-sulphate, de-epoxy-DON, as well as of ZEA, ZEA-14-glucuronide, α-zearalenol and α-zearalenol-14-glucuronide, analysed using LC-MS/MS, were used to calculate urinary DON and ZEA equivalent concentrations (DONe and ZEAe). The urinary concentration of DONe (P < 0.001), but not of ZEAe (P = 0.31), was lower in the fasted than that in the fed animals. The urinary DONe/creatinine and ZEAe/creatinine ratios were highly correlated with DON and ZEA intake per kg body weight the day preceding sampling (r = 0.76 and 0.77; P < 0.001). The correlations between DON intake during the 7 h preceding urine sampling in the afternoon and urinary DONe/creatinine ratio (r = 0.88) as well as between mean ZEA intake during 3 days preceding urine sampling and urinary ZEAe/creatinine ratio (r = 0.84) were even higher, reflecting the plasma elimination half-time of several hours for DON and of more than 3 days for ZEA. ZEAe analysed in enzymatically hydrolysed urine using an ELISA kit was highly correlated with the LC-MS/MS data (r = 0.94). The urinary DONe and ZEAe to creatinine ratios, analysed in pooled urine samples of several pigs fed the same diet, can be used to estimate their exposure to DON and ZEA.

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Section: Animals Materials and Methodsmentioning

confidence: 99%

Urinary deoxynivalenol (DON) and zearalenone (ZEA) as biomarkers of DON and ZEA exposure of pigs

et al. 2016

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“…were purchased from Merck (Darmstadt, Germany) and acetonitrile (ACN; LC gradient grade) from VWR (Leuven, Belgium). Deoxynivalenol‐3‐ O ‐glucuronide and zearalenone‐14‐ O ‐glucuronide were synthesized by an optimized procedure and the structure of the product was confirmed by nuclear magnetic resonance . Other standards were purchased from Romer Labs Diagnostic GmbH (Tulln, Austria) (DON, 13 C‐DON, DOM‐1, NIV, T‐2, HT‐2, OTA, AFM 1 , FB 1 and FB 2 ) or Sigma (ZEN, α‐ and β‐ZEL).…”

Section: Methodsmentioning

confidence: 99%

Development and validation of a rapid multi‐biomarker liquid chromatography/tandem mass spectrometry method to assess human exposure to mycotoxins

Warth

Sulyok

Fruhmann

et al. 2012

Rapid Comm Mass Spectrometry

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We conclude that the developed LC/MS/MS method is well suited to quantify multiple mycotoxin biomarkers in human urine down to the sub-ppb range within 18 min and without any prior cleanup. The co-occurrence of several mycotoxins in the investigated samples clearly emphasizes the great potential and importance of this method to assess exposure of humans and animals to naturally occurring mycotoxins.

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“…Chemicals, products and reagents Analytical standards of DON, DOM-1, 3-ADON, 15-ADON and 13 C 15 -DON (IS) were obtained from Sigma Aldrich (Bornem, Belgium). The analytical standard of DON-3-GlcA was synthesized as described by Fruhmann et al (2012) and kindly supplied by Dr. Huybrechts (CODA-CERVA). All standards were stored at ≤ − 15 °C.…”

Section: Analysis Of Don and Metabolites In Calf Urinementioning

confidence: 99%

The role of roughage provision on the absorption and disposition of the mycotoxin deoxynivalenol and its acetylated derivatives in calves: from field observations to toxicokinetics

et al. 2018

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A clinical case in Belgium demonstrated that feeding a feed concentrate containing considerable levels of deoxynivalenol (DON, 1.13 mg/kg feed) induced severe liver failure in 2-to 3-month-old beef calves. Symptoms disappeared by replacing the highly contaminated corn and by stimulating ruminal development via roughage administration. A multi-mycotoxin contamination was demonstrated in feed samples collected at 15 different veal farms in Belgium. DON was most prevalent, contaminating 80% of the roughage samples (mixed straw and maize silage; average concentration in positives: 637 ± 621 µg/ kg, max. 1818 µg/kg), and all feed concentrate samples (411 ± 156 µg/kg, max. 693 µg/kg). In order to evaluate the impact of roughage provision and its associated ruminal development on the gastro-intestinal absorption and biodegradation of DON and its acetylated derivatives (3-and 15-ADON) in calves, a toxicokinetic study was performed with two ruminating and two non-ruminating male calves. Animals received in succession a bolus of DON (120 µg/kg bodyweight (BW)), 15-ADON (50 µg/kg BW), and 3-ADON (25 µg/kg) by intravenous (IV) injection or per os (PO) in a cross-over design. The absolute oral bioavailability of DON was much higher in non-ruminating calves (50.7 ± 33.0%) compared to ruminating calves (4.1 ± 4.5%). Immediately following exposure, 3-and 15-ADON were hydrolysed to DON in ruminating calves. DON and its acetylated metabolites were mainly metabolized to DON-3-glucuronide, however, also small amounts of DON-15-glucuronide were detected in urine. DON degradation to deepoxy-DON (DOM-1) was only observed to a relevant extent in ruminating calves. Consequently, toxicity of DON in calves is closely related to roughage provision and the associated stage of ruminal development.Keywords Biodegradation · Calf · Deoxynivalenol · 3-and 15-Acetyldeoxynivalenol · Mycotoxin · Toxicokinetics Bonnie Valgaeren and Léonard Théron contributed equally to this work.Alfons Callebaut: Deceased. Electronic supplementary materialThe online version of this article (https ://doi.

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Synthesis of deoxynivalenol-3-ß-D-O-glucuronide for its use as biomarker for dietary deoxynivalenol exposure

Cited by 40 publications

References 12 publications

Urinary deoxynivalenol (DON) and zearalenone (ZEA) as biomarkers of DON and ZEA exposure of pigs

Urinary deoxynivalenol (DON) and zearalenone (ZEA) as biomarkers of DON and ZEA exposure of pigs

Development and validation of a rapid multi‐biomarker liquid chromatography/tandem mass spectrometry method to assess human exposure to mycotoxins

The role of roughage provision on the absorption and disposition of the mycotoxin deoxynivalenol and its acetylated derivatives in calves: from field observations to toxicokinetics

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