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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...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2011
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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. |
format | Online Article Text |
id | pubmed-3175691 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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