Deoxynivalenol

Structural formula
General
Surname	Deoxynivalenol
other names	(3 β , 7 α ) -3,7,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one ( IUPAC ) ; 12,13-epoxy-3,7,15-trihydroxy-trichothec-9-en-8-one; DON; Vomitoxin;
Molecular formula	C 15 H 20 O 6
External identifiers / databases
EC number	610-668-0
ECHA InfoCard	100.129.971
PubChem	40024
ChemSpider	36584
Wikidata	Q420518
properties
Molar mass	296.32 g mol −1
Physical state	firmly
Melting point	151-153 ° C
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 300
	P: 264-301 + 310
Toxicological data	46 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Deoxynivalenol (DON), also known as vomitoxin , is a mycotoxin (mold toxin ) with a trichothecene framework and a sesquiterpene .

Occurrence

Deoxynivalenol occurs as a metabolic product of various fungi of the genus Fusarium ( Fusarium culmorum , Fusarium graminearum ), especially on infected grain ( wheat , barley , oats , maize ). In a study of American rivers, deoxynivalenol was the most commonly detected mycotoxin.

properties

Deoxynivalenol is relatively resistant to chemicals. In an aqueous medium, temperatures greater than 120 ° C are necessary to achieve partial degradation. High pH values promote degradation. Well-known degradation products are norDON A, norDON B and norDON C, 9-hydroxymethyl DON lactone, norDON D, norDON E and norDON F. Degradation when baking rolls was observed.

Analytics

The reliable identification and quantification of DON in the different matrices can be guaranteed by chromatographic and mass spectrometric methods. Both gas chromatography (GC) and high-performance liquid chromatography (HPLC) have proven to be reliable separation techniques. Suitable derivatives (e.g. trimethylsilyl derivatives ) are generally used for gas chromatographic analysis . With HPLC, separations and MS measurements are also possible without derivatisation. The subsequent mass spectrometry is possible with both ion trap and quadrupole systems. The use of both MS ionization techniques can considerably increase the reliability of the analytical statements in the so-called 'low-level' range. The mass spectrum of deoxynivalenol is listed in the spectrum library of the NIST .

Biological importance

Deoxynivalenol is a mycotoxin. Acute toxic doses cause nausea and vomiting , how do the other synonyms vomitoxin (of English. Vomit "vomit" and toxin "poison") is derived. It is a gastrointestinal irritant. Deoxynivalenol is an inhibitor of protein synthesis . In livestock, feed contaminated with deoxynivalenol causes growth retardation, an impairment of the immune system with the consequence of an increased susceptibility to infection. A certain teratogenicity can be demonstrated.

Avoidance strategies

During the production of cereals, numerous measures can be taken to reduce the concentration of deoxynivalenol in the crop. These include avoiding maize as a previous crop, turning the soil, cultivating types of grain with low susceptibility to Fusarium species and the use of fungicides .

Reduction in further processing

In the grain mill , the DON content of a batch of grain can - if it is not completely rejected - through cleaning steps, such as B. black or white cleaning can be further reduced. Table separators (paddy separators) can also be used, as fusarium grains are lighter than healthy wheat grains. The DON content in the bran is higher than in the flour kernel. With contemporary processing of grain, the DON content in the first flour was reduced by 36% compared to white-cleaned grain, while other authors report a reduction of up to 50%.

Maximum amount regulation

According to EU Regulation 1881/2006, the legal maximum amounts for deoxynivalenol are 750 µg / kg for cereal products, 500 µg / kg for bread, biscuits and fine baked goods and 200 µg / kg for cereal products for the production of baby food.

Web links

Detailed information on Deoxynivalenol at Romer Labs (English) ( Memento from September 8, 2008 in the Internet Archive )

Individual evidence

↑ Entry on Deoxynivalenol. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.
↑ ^a ^b Deoxynivalenol data sheet from Sigma-Aldrich , accessed on November 4, 2016 ( PDF ).

↑ Entry on deoxynivalenol in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.

↑ USGS message: Toxins Produced by Molds Measured in US Streams , according to doi : 10.1016 / j.scitotenv.2013.09.062 .

^ CE Wolf, LB Bullerman: Heat and pH alter the concentration of deoxynivalenol in an aqueous environment. In: Journal of Food Protection . No. 61 , 1998, pp. 365-367 , PMID 9708313 .

↑ M. Bretz, M. Beyer, B. Cramer, HU. Humpf :: Thermal degradation of the Fusarium mycotoxin deoxynivalenol. In: Journal of Agricultural and Food Chemistry . No. 54 , 2006, pp. 6445-6451 , doi : 10.1021 / jf061008g .

↑ Ragab, S. Drusch, A. Kuhlmann, M. Beyer :: Characterizing effects of fermentation and baking on the deoxynivalenol content of rolls . In: Journal of Applied Botany and Food Quality . No. 79 , 2005, pp. 197-201 .

↑ HU. Melchert, E. Pabel: Reliable identification and quantification of trichothecenes and other mycotoxins by electron impact and chemical ionization-gas chromatography-mass spectrometry, using an ion-trap system in the multiple mass spectrometry mode - Candidate reference method for complex matrices . In: Journal of Chromatography . A 1056, 2004, p. 195-199 . , PMID 15595550

↑ Entry on Deoxynivalenol (mass spectrum, electron ionization). In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed November 17, 2019.

↑ James Mannon & Eric Johnson (1985) Fungi down in the farm New Scientist, No. 1445 (Feb. 28), 12-16.

↑ Pestka JJ .: deoxynivalenol: mechanisms of action, human exposure, and toxicological relevance. In: Arch. Toxicol. 2010 Sep; 84 (9): 663-79. PMID 20798930 .

↑ M. Beyer, MB Klix, H. Klink, JA. Verreet :: Quantification of the influence of previous crop, tillage, cultivar and triazole fungicides on deoxynivalenol content in wheat - a review . In: Journal of Plant Diseases and Protection . tape 113 , no. 6 , 2006, p. 241-246 ( abstract [PDF]).

↑ J. Wolff: Effects of treatment and processing on the deoxynivalenol and zearalenone contents in grain and grain products . In: Mycotoxin research . tape 21 , no. 4 , 2005, p. 246-250 .

↑ J. Lepschy, A. Süß: Distribution of the trichothecene mycotoxin deoxynivalenol in the milling of wheat . In: Grain, Flour and Bread . tape 50 , 1996, pp. 340-342 .

↑ REGULATION (EC) No. 1881/2006 OF THE COMMISSION of December 19, 2006 setting the maximum levels for certain contaminants in food (PDF) .

[roempp-1] Entry on Deoxynivalenol. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.

[Sigma-2] Deoxynivalenol data sheet from Sigma-Aldrich , accessed on November 4, 2016 ( PDF ).

[3] Entry on deoxynivalenol in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.

[4] USGS message: Toxins Produced by Molds Measured in US Streams , according to doi : 10.1016 / j.scitotenv.2013.09.062 .

[5] CE Wolf, LB Bullerman: Heat and pH alter the concentration of deoxynivalenol in an aqueous environment. In: Journal of Food Protection . No. 61 , 1998, pp. 365-367 , PMID 9708313 .

[6] M. Bretz, M. Beyer, B. Cramer, HU. Humpf :: Thermal degradation of the Fusarium mycotoxin deoxynivalenol. In: Journal of Agricultural and Food Chemistry . No. 54 , 2006, pp. 6445-6451 , doi : 10.1021 / jf061008g .

[7] Ragab, S. Drusch, A. Kuhlmann, M. Beyer :: Characterizing effects of fermentation and baking on the deoxynivalenol content of rolls . In: Journal of Applied Botany and Food Quality . No. 79 , 2005, pp. 197-201 .

[8] HU. Melchert, E. Pabel: Reliable identification and quantification of trichothecenes and other mycotoxins by electron impact and chemical ionization-gas chromatography-mass spectrometry, using an ion-trap system in the multiple mass spectrometry mode - Candidate reference method for complex matrices . In: Journal of Chromatography . A 1056, 2004, p. 195-199 . , PMID 15595550

[9] Entry on Deoxynivalenol (mass spectrum, electron ionization). In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed November 17, 2019.

[10] James Mannon & Eric Johnson (1985) Fungi down in the farm New Scientist, No. 1445 (Feb. 28), 12-16.

[11] Pestka JJ .: deoxynivalenol: mechanisms of action, human exposure, and toxicological relevance. In: Arch. Toxicol. 2010 Sep; 84 (9): 663-79. PMID 20798930 .

[12] M. Beyer, MB Klix, H. Klink, JA. Verreet :: Quantification of the influence of previous crop, tillage, cultivar and triazole fungicides on deoxynivalenol content in wheat - a review . In: Journal of Plant Diseases and Protection . tape 113 , no. 6 , 2006, p. 241-246 ( abstract [PDF]).

[13] J. Wolff: Effects of treatment and processing on the deoxynivalenol and zearalenone contents in grain and grain products . In: Mycotoxin research . tape 21 , no. 4 , 2005, p. 246-250 .

[14] J. Lepschy, A. Süß: Distribution of the trichothecene mycotoxin deoxynivalenol in the milling of wheat . In: Grain, Flour and Bread . tape 50 , 1996, pp. 340-342 .

[15] REGULATION (EC) No. 1881/2006 OF THE COMMISSION of December 19, 2006 setting the maximum levels for certain contaminants in food (PDF) .