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Isolation and Characterization of a New Less-Toxic Derivative of the Fusarium Mycotoxin Diacetoxyscirpenol after Thermal Treatment

Trichothecenes are an important class of mycotoxins that act as potent protein synthesis inhibitors in eukaryotic organisms. The compound 4,15-diacetoxyscirpenol is highly toxic for plants and animals. Potatoes are especially prone to be contaminated with 4,15-diacetoxyscirpenol after infection with...

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Autores principales: Shams, Mehrdad, Mitterbauer, Rudolf, Corradini, Roberto, Wiesenberger, Gerlinde, Dall’Asta, Chiara, Schuhmacher, Rainer, Krska, Rudolf, Adam, Gerhard, Berthiller, Franz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2011
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3175691/
https://www.ncbi.nlm.nih.gov/pubmed/21800832
http://dx.doi.org/10.1021/jf2022176
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author Shams, Mehrdad
Mitterbauer, Rudolf
Corradini, Roberto
Wiesenberger, Gerlinde
Dall’Asta, Chiara
Schuhmacher, Rainer
Krska, Rudolf
Adam, Gerhard
Berthiller, Franz
author_facet Shams, Mehrdad
Mitterbauer, Rudolf
Corradini, Roberto
Wiesenberger, Gerlinde
Dall’Asta, Chiara
Schuhmacher, Rainer
Krska, Rudolf
Adam, Gerhard
Berthiller, Franz
author_sort Shams, Mehrdad
collection PubMed
description Trichothecenes are an important class of mycotoxins that act as potent protein synthesis inhibitors in eukaryotic organisms. The compound 4,15-diacetoxyscirpenol is highly toxic for plants and animals. Potatoes are especially prone to be contaminated with 4,15-diacetoxyscirpenol after infection with Fusarium sambucinum. In the current study, the reduction of 4,15-diacetoxyscirpenol during thermal treatment in aqueous solution was monitored. A new derivative was detected and named DAS-M1. After isolation, DAS-M1 was characterized with LC–HR-MS and LC–MS/MS and structurally elucidated with (1)H, (13)C, and 2D NMR. Potatoes were inoculated with F. sambucinum, and the infected potatoes were cooked at 100 or 121 °C, respectively. A reduction of 4,15-diacetoxyscirpenol from about 26% (1 h at 100 °C) to 100% (4 h at 121 °C) was detected by means of LC–MS/MS analysis. The effects of different pH values on the reduction of 4,15-diacetoxyscirpenol were investigated, showing higher conversion rates at more acidic pH values. In addition, the toxicity of 4,15-diacetoxyscirpenol and DAS-M1 was compared in vitro using a wheat germ transcription/translation assay and in vivo on Saccharomyces cerevisiae. The results show that the inhibitory effect of DAS-M1 on yeast growth is about 50 times lower and inhibition of protein synthesis is about 100 times lower than that of 4,15-diacetoxyscirpenol.
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spelling pubmed-31756912011-09-22 Isolation and Characterization of a New Less-Toxic Derivative of the Fusarium Mycotoxin Diacetoxyscirpenol after Thermal Treatment Shams, Mehrdad Mitterbauer, Rudolf Corradini, Roberto Wiesenberger, Gerlinde Dall’Asta, Chiara Schuhmacher, Rainer Krska, Rudolf Adam, Gerhard Berthiller, Franz J Agric Food Chem Trichothecenes are an important class of mycotoxins that act as potent protein synthesis inhibitors in eukaryotic organisms. The compound 4,15-diacetoxyscirpenol is highly toxic for plants and animals. Potatoes are especially prone to be contaminated with 4,15-diacetoxyscirpenol after infection with Fusarium sambucinum. In the current study, the reduction of 4,15-diacetoxyscirpenol during thermal treatment in aqueous solution was monitored. A new derivative was detected and named DAS-M1. After isolation, DAS-M1 was characterized with LC–HR-MS and LC–MS/MS and structurally elucidated with (1)H, (13)C, and 2D NMR. Potatoes were inoculated with F. sambucinum, and the infected potatoes were cooked at 100 or 121 °C, respectively. A reduction of 4,15-diacetoxyscirpenol from about 26% (1 h at 100 °C) to 100% (4 h at 121 °C) was detected by means of LC–MS/MS analysis. The effects of different pH values on the reduction of 4,15-diacetoxyscirpenol were investigated, showing higher conversion rates at more acidic pH values. In addition, the toxicity of 4,15-diacetoxyscirpenol and DAS-M1 was compared in vitro using a wheat germ transcription/translation assay and in vivo on Saccharomyces cerevisiae. The results show that the inhibitory effect of DAS-M1 on yeast growth is about 50 times lower and inhibition of protein synthesis is about 100 times lower than that of 4,15-diacetoxyscirpenol. American Chemical Society 2011-07-29 2011-09-14 /pmc/articles/PMC3175691/ /pubmed/21800832 http://dx.doi.org/10.1021/jf2022176 Text en Copyright © 2011 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org.
spellingShingle Shams, Mehrdad
Mitterbauer, Rudolf
Corradini, Roberto
Wiesenberger, Gerlinde
Dall’Asta, Chiara
Schuhmacher, Rainer
Krska, Rudolf
Adam, Gerhard
Berthiller, Franz
Isolation and Characterization of a New Less-Toxic Derivative of the Fusarium Mycotoxin Diacetoxyscirpenol after Thermal Treatment
title Isolation and Characterization of a New Less-Toxic Derivative of the Fusarium Mycotoxin Diacetoxyscirpenol after Thermal Treatment
title_full Isolation and Characterization of a New Less-Toxic Derivative of the Fusarium Mycotoxin Diacetoxyscirpenol after Thermal Treatment
title_fullStr Isolation and Characterization of a New Less-Toxic Derivative of the Fusarium Mycotoxin Diacetoxyscirpenol after Thermal Treatment
title_full_unstemmed Isolation and Characterization of a New Less-Toxic Derivative of the Fusarium Mycotoxin Diacetoxyscirpenol after Thermal Treatment
title_short Isolation and Characterization of a New Less-Toxic Derivative of the Fusarium Mycotoxin Diacetoxyscirpenol after Thermal Treatment
title_sort isolation and characterization of a new less-toxic derivative of the fusarium mycotoxin diacetoxyscirpenol after thermal treatment
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3175691/
https://www.ncbi.nlm.nih.gov/pubmed/21800832
http://dx.doi.org/10.1021/jf2022176
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