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Less-toxic rearrangement products of NX-toxins are formed during storage and food processing.

Identifieur interne : 000831 ( Main/Exploration ); précédent : 000830; suivant : 000832

Less-toxic rearrangement products of NX-toxins are formed during storage and food processing.

Auteurs : Elisabeth Varga [Autriche] ; Gerlinde Wiesenberger [Autriche] ; Lydia Woelflingseder [Autriche] ; Krisztian Twaruschek [Autriche] ; Christian Hametner [Autriche] ; Marta Vaclaviková [Autriche] ; Alexandra Malachová [Autriche] ; Doris Marko [Autriche] ; Franz Berthiller [Autriche] ; Gerhard Adam [Autriche]

Source :

RBID : pubmed:29277571

Descripteurs français

English descriptors

Abstract

A new type A trichothecene mycotoxin, NX-2, was previously reported to be produced by North American isolates of the cereal pathogen Fusarium graminearum. Here we describe the isolation and structural characterization of a rearrangement product, called NX2-M1, and related compounds with different acetylation patterns (NX3-M1 and NX4-M1). In the NX-M1 derivatives, the epoxide ring is opened, and a covalent bridge between C-10 and C-12 of the trichothecene backbone is formed. In vitro translation assays showed that NX3-M1 is less toxic for eukaryotic ribosomes than NX-3. NX3-M1 also has a greatly reduced cytotoxic potential on two tested human colon cell lines. Formation of NX3-M1 can therefore be regarded as a detoxification reaction. The related F. graminearum mycotoxin deoxynivalenol (DON), which is frequently occurring worldwide, is very stable during food processing. Testing NX-3 at different pH-values and temperature conditions, as well as under conditions that simulate the storage of infected grains and bread-making process, revealed a strongly reduced stability of NX-3 and concurrent formation of NX3-M1. Although the NX-3 formed in planta is as toxic as DON, the extensive formation of the non-toxic rearrangement product should be taken into account for risk assessment of this emerging food contaminant.

DOI: 10.1016/j.toxlet.2017.12.016
PubMed: 29277571


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<div type="abstract" xml:lang="en">A new type A trichothecene mycotoxin, NX-2, was previously reported to be produced by North American isolates of the cereal pathogen Fusarium graminearum. Here we describe the isolation and structural characterization of a rearrangement product, called NX2-M1, and related compounds with different acetylation patterns (NX3-M1 and NX4-M1). In the NX-M1 derivatives, the epoxide ring is opened, and a covalent bridge between C-10 and C-12 of the trichothecene backbone is formed. In vitro translation assays showed that NX3-M1 is less toxic for eukaryotic ribosomes than NX-3. NX3-M1 also has a greatly reduced cytotoxic potential on two tested human colon cell lines. Formation of NX3-M1 can therefore be regarded as a detoxification reaction. The related F. graminearum mycotoxin deoxynivalenol (DON), which is frequently occurring worldwide, is very stable during food processing. Testing NX-3 at different pH-values and temperature conditions, as well as under conditions that simulate the storage of infected grains and bread-making process, revealed a strongly reduced stability of NX-3 and concurrent formation of NX3-M1. Although the NX-3 formed in planta is as toxic as DON, the extensive formation of the non-toxic rearrangement product should be taken into account for risk assessment of this emerging food contaminant.</div>
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<Year>2018</Year>
<Month>02</Month>
<Day>21</Day>
</DateCompleted>
<DateRevised>
<Year>2018</Year>
<Month>02</Month>
<Day>21</Day>
</DateRevised>
<Article PubModel="Print-Electronic">
<Journal>
<ISSN IssnType="Electronic">1879-3169</ISSN>
<JournalIssue CitedMedium="Internet">
<Volume>284</Volume>
<PubDate>
<Year>2018</Year>
<Month>Mar</Month>
<Day>01</Day>
</PubDate>
</JournalIssue>
<Title>Toxicology letters</Title>
<ISOAbbreviation>Toxicol Lett</ISOAbbreviation>
</Journal>
<ArticleTitle>Less-toxic rearrangement products of NX-toxins are formed during storage and food processing.</ArticleTitle>
<Pagination>
<MedlinePgn>205-212</MedlinePgn>
</Pagination>
<ELocationID EIdType="pii" ValidYN="Y">S0378-4274(17)31526-6</ELocationID>
<ELocationID EIdType="doi" ValidYN="Y">10.1016/j.toxlet.2017.12.016</ELocationID>
<Abstract>
<AbstractText>A new type A trichothecene mycotoxin, NX-2, was previously reported to be produced by North American isolates of the cereal pathogen Fusarium graminearum. Here we describe the isolation and structural characterization of a rearrangement product, called NX2-M1, and related compounds with different acetylation patterns (NX3-M1 and NX4-M1). In the NX-M1 derivatives, the epoxide ring is opened, and a covalent bridge between C-10 and C-12 of the trichothecene backbone is formed. In vitro translation assays showed that NX3-M1 is less toxic for eukaryotic ribosomes than NX-3. NX3-M1 also has a greatly reduced cytotoxic potential on two tested human colon cell lines. Formation of NX3-M1 can therefore be regarded as a detoxification reaction. The related F. graminearum mycotoxin deoxynivalenol (DON), which is frequently occurring worldwide, is very stable during food processing. Testing NX-3 at different pH-values and temperature conditions, as well as under conditions that simulate the storage of infected grains and bread-making process, revealed a strongly reduced stability of NX-3 and concurrent formation of NX3-M1. Although the NX-3 formed in planta is as toxic as DON, the extensive formation of the non-toxic rearrangement product should be taken into account for risk assessment of this emerging food contaminant.</AbstractText>
<CopyrightInformation>Copyright © 2017 The Author(s). Published by Elsevier B.V. All rights reserved.</CopyrightInformation>
</Abstract>
<AuthorList CompleteYN="Y">
<Author ValidYN="Y">
<LastName>Varga</LastName>
<ForeName>Elisabeth</ForeName>
<Initials>E</Initials>
<AffiliationInfo>
<Affiliation>Christian Doppler Laboratory for Mycotoxin Metabolism and Center for Analytical Chemistry, Department of Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences, Vienna (BOKU), Tulln, Austria. Electronic address: elisabeth.varga@boku.ac.at.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Wiesenberger</LastName>
<ForeName>Gerlinde</ForeName>
<Initials>G</Initials>
<AffiliationInfo>
<Affiliation>Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Tulln, Austria. Electronic address: gerlinde.wiesenberger@boku.ac.at.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Woelflingseder</LastName>
<ForeName>Lydia</ForeName>
<Initials>L</Initials>
<AffiliationInfo>
<Affiliation>Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Tulln, Austria; Department of Food Chemistry and Toxicology, University of Vienna, Vienna, Austria. Electronic address: lydia.woelflingseder@univie.ac.at.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Twaruschek</LastName>
<ForeName>Krisztian</ForeName>
<Initials>K</Initials>
<AffiliationInfo>
<Affiliation>Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Tulln, Austria. Electronic address: krisztian.twaruschek@boku.ac.at.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Hametner</LastName>
<ForeName>Christian</ForeName>
<Initials>C</Initials>
<AffiliationInfo>
<Affiliation>Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria. Electronic address: christian.hametner@tuwien.ac.at.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Vaclaviková</LastName>
<ForeName>Marta</ForeName>
<Initials>M</Initials>
<AffiliationInfo>
<Affiliation>Christian Doppler Laboratory for Mycotoxin Metabolism and Center for Analytical Chemistry, Department of Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences, Vienna (BOKU), Tulln, Austria. Electronic address: marta.vaclavikova@boku.ac.at.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Malachová</LastName>
<ForeName>Alexandra</ForeName>
<Initials>A</Initials>
<AffiliationInfo>
<Affiliation>Christian Doppler Laboratory for Mycotoxin Metabolism and Center for Analytical Chemistry, Department of Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences, Vienna (BOKU), Tulln, Austria. Electronic address: alexandra.malachova@boku.ac.at.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Marko</LastName>
<ForeName>Doris</ForeName>
<Initials>D</Initials>
<AffiliationInfo>
<Affiliation>Department of Food Chemistry and Toxicology, University of Vienna, Vienna, Austria. Electronic address: doris.marko@univie.ac.at.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Berthiller</LastName>
<ForeName>Franz</ForeName>
<Initials>F</Initials>
<AffiliationInfo>
<Affiliation>Christian Doppler Laboratory for Mycotoxin Metabolism and Center for Analytical Chemistry, Department of Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences, Vienna (BOKU), Tulln, Austria. Electronic address: franz.berthiller@boku.ac.at.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Adam</LastName>
<ForeName>Gerhard</ForeName>
<Initials>G</Initials>
<AffiliationInfo>
<Affiliation>Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Tulln, Austria. Electronic address: gerhard.adam@boku.ac.at.</Affiliation>
</AffiliationInfo>
</Author>
</AuthorList>
<Language>eng</Language>
<PublicationTypeList>
<PublicationType UI="D016428">Journal Article</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic">
<Year>2017</Year>
<Month>12</Month>
<Day>23</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo>
<Country>Netherlands</Country>
<MedlineTA>Toxicol Lett</MedlineTA>
<NlmUniqueID>7709027</NlmUniqueID>
<ISSNLinking>0378-4274</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList>
<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D014255">Trichothecenes</NameOfSubstance>
</Chemical>
<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="C000608633">trichothecene NX-2</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList>
<MeshHeading>
<DescriptorName UI="D002470" MajorTopicYN="N">Cell Survival</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D003106" MajorTopicYN="N">Colon</DescriptorName>
<QualifierName UI="Q000166" MajorTopicYN="N">cytology</QualifierName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D002523" MajorTopicYN="Y">Edible Grain</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000382" MajorTopicYN="N">microbiology</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D005506" MajorTopicYN="N">Food Contamination</DescriptorName>
<QualifierName UI="Q000032" MajorTopicYN="N">analysis</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D005511" MajorTopicYN="Y">Food Handling</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D005516" MajorTopicYN="N">Food Microbiology</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D061353" MajorTopicYN="N">Food Storage</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D005670" MajorTopicYN="N">Fusarium</DescriptorName>
<QualifierName UI="Q000254" MajorTopicYN="Y">growth & development</QualifierName>
<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D019073" MajorTopicYN="N">HT29 Cells</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D006358" MajorTopicYN="N">Hot Temperature</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D006863" MajorTopicYN="N">Hydrogen-Ion Concentration</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D014255" MajorTopicYN="Y">Trichothecenes</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName>
<QualifierName UI="Q000633" MajorTopicYN="N">toxicity</QualifierName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM">
<Keyword MajorTopicYN="N">Alamar Blue assay</Keyword>
<Keyword MajorTopicYN="N">Detoxification</Keyword>
<Keyword MajorTopicYN="N">Fusarium graminearum</Keyword>
<Keyword MajorTopicYN="N">Sulforhodamine B assay</Keyword>
<Keyword MajorTopicYN="N">Trichothecene</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData>
<History>
<PubMedPubDate PubStatus="received">
<Year>2017</Year>
<Month>11</Month>
<Day>08</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="revised">
<Year>2017</Year>
<Month>12</Month>
<Day>15</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="accepted">
<Year>2017</Year>
<Month>12</Month>
<Day>20</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed">
<Year>2017</Year>
<Month>12</Month>
<Day>27</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline">
<Year>2018</Year>
<Month>2</Month>
<Day>22</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez">
<Year>2017</Year>
<Month>12</Month>
<Day>27</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList>
<ArticleId IdType="pubmed">29277571</ArticleId>
<ArticleId IdType="pii">S0378-4274(17)31526-6</ArticleId>
<ArticleId IdType="doi">10.1016/j.toxlet.2017.12.016</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
<affiliations>
<list>
<country>
<li>Autriche</li>
</country>
<region>
<li>Vienne (Autriche)</li>
</region>
<settlement>
<li>Vienne (Autriche)</li>
</settlement>
</list>
<tree>
<country name="Autriche">
<noRegion>
<name sortKey="Varga, Elisabeth" sort="Varga, Elisabeth" uniqKey="Varga E" first="Elisabeth" last="Varga">Elisabeth Varga</name>
</noRegion>
<name sortKey="Adam, Gerhard" sort="Adam, Gerhard" uniqKey="Adam G" first="Gerhard" last="Adam">Gerhard Adam</name>
<name sortKey="Berthiller, Franz" sort="Berthiller, Franz" uniqKey="Berthiller F" first="Franz" last="Berthiller">Franz Berthiller</name>
<name sortKey="Hametner, Christian" sort="Hametner, Christian" uniqKey="Hametner C" first="Christian" last="Hametner">Christian Hametner</name>
<name sortKey="Malachova, Alexandra" sort="Malachova, Alexandra" uniqKey="Malachova A" first="Alexandra" last="Malachová">Alexandra Malachová</name>
<name sortKey="Marko, Doris" sort="Marko, Doris" uniqKey="Marko D" first="Doris" last="Marko">Doris Marko</name>
<name sortKey="Twaruschek, Krisztian" sort="Twaruschek, Krisztian" uniqKey="Twaruschek K" first="Krisztian" last="Twaruschek">Krisztian Twaruschek</name>
<name sortKey="Vaclavikova, Marta" sort="Vaclavikova, Marta" uniqKey="Vaclavikova M" first="Marta" last="Vaclaviková">Marta Vaclaviková</name>
<name sortKey="Wiesenberger, Gerlinde" sort="Wiesenberger, Gerlinde" uniqKey="Wiesenberger G" first="Gerlinde" last="Wiesenberger">Gerlinde Wiesenberger</name>
<name sortKey="Woelflingseder, Lydia" sort="Woelflingseder, Lydia" uniqKey="Woelflingseder L" first="Lydia" last="Woelflingseder">Lydia Woelflingseder</name>
</country>
</tree>
</affiliations>
</record>

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