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Nor-guanacastepene pigments from the Chilean mushroom Cortinarius pyromyxa.

Identifieur interne : 000441 ( Main/Exploration ); précédent : 000440; suivant : 000442

Nor-guanacastepene pigments from the Chilean mushroom Cortinarius pyromyxa.

Auteurs : Yen T H. Lam [Allemagne] ; Götz Palfner [Chili] ; Celia Lima [Chili] ; Andrea Porzel [Allemagne] ; Wolfgang Brandt [Allemagne] ; Andrej Frolov [Russie] ; Haider Sultani [Allemagne] ; Katrin Franke [Allemagne] ; Christoph Wagner [Allemagne] ; Kurt Merzweiler [Allemagne] ; Ludger A. Wessjohann [Allemagne] ; Norbert Arnold [Allemagne]

Source :

RBID : pubmed:31229789

Descripteurs français

English descriptors

Abstract

For the first time, the pigment composition of basidiocarps from the Chilean mushroom Cortinarius pyromyxa was studied under various aspects like phylogeny, chemistry and antibiotic activity. A molecular biological study supports the monotypic position of C. pyromyxa in subgenus Myxacium, genus Cortinarius. Four undescribed diterpenoids, named pyromyxones A-D, were isolated from fruiting bodies of C. pyromyxa. Their chemical structures were elucidated based on comprehensive one- and two-dimensional NMR spectroscopic analysis, ESI-HRMS measurements, as well as X-ray crystallography. In addition, the absolute configurations of pyromyxones A-D were established with the aid of JH,H, NOESY spectra and quantum chemical CD calculation. The pyromyxones A-D possess the undescribed nor-guanacastane skeleton. Tested pyromyxones A, B, and D exhibit only weak activity against gram-positive Bacillus subtilis and gram-negative Aliivibrio fischeri as well as the phytopathogenic fungi Botrytis cinerea, Septoria tritici and Phytophthora infestans.

DOI: 10.1016/j.phytochem.2019.05.021
PubMed: 31229789


Affiliations:


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Le document en format XML

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<term>Anti-Bacterial Agents (isolation & purification)</term>
<term>Anti-Bacterial Agents (pharmacology)</term>
<term>Cortinarius (chemistry)</term>
<term>Crystallography, X-Ray (MeSH)</term>
<term>Diterpenes (chemistry)</term>
<term>Diterpenes (isolation & purification)</term>
<term>Diterpenes (pharmacology)</term>
<term>Gram-Negative Bacteria (drug effects)</term>
<term>Gram-Positive Bacteria (drug effects)</term>
<term>Microbial Sensitivity Tests (MeSH)</term>
<term>Models, Molecular (MeSH)</term>
<term>Molecular Structure (MeSH)</term>
<term>Phylogeny (MeSH)</term>
<term>Pigments, Biological (chemistry)</term>
<term>Pigments, Biological (isolation & purification)</term>
<term>Pigments, Biological (pharmacology)</term>
<term>Quantum Theory (MeSH)</term>
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<term>Antibactériens (composition chimique)</term>
<term>Antibactériens (isolement et purification)</term>
<term>Antibactériens (pharmacologie)</term>
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<term>Bactéries à Gram positif (effets des médicaments et des substances chimiques)</term>
<term>Cortinarius (composition chimique)</term>
<term>Cristallographie aux rayons X (MeSH)</term>
<term>Diterpènes (composition chimique)</term>
<term>Diterpènes (isolement et purification)</term>
<term>Diterpènes (pharmacologie)</term>
<term>Modèles moléculaires (MeSH)</term>
<term>Phylogenèse (MeSH)</term>
<term>Pigments biologiques (composition chimique)</term>
<term>Pigments biologiques (isolement et purification)</term>
<term>Pigments biologiques (pharmacologie)</term>
<term>Structure moléculaire (MeSH)</term>
<term>Tests de sensibilité microbienne (MeSH)</term>
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<term>Diterpenes</term>
<term>Pigments, Biological</term>
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<term>Pigments, Biological</term>
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<keywords scheme="MESH" qualifier="chemistry" xml:lang="en">
<term>Cortinarius</term>
</keywords>
<keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr">
<term>Antibactériens</term>
<term>Cortinarius</term>
<term>Diterpènes</term>
<term>Pigments biologiques</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en">
<term>Gram-Negative Bacteria</term>
<term>Gram-Positive Bacteria</term>
</keywords>
<keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr">
<term>Bactéries à Gram négatif</term>
<term>Bactéries à Gram positif</term>
</keywords>
<keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr">
<term>Antibactériens</term>
<term>Diterpènes</term>
<term>Pigments biologiques</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr">
<term>Antibactériens</term>
<term>Diterpènes</term>
<term>Pigments biologiques</term>
</keywords>
<keywords scheme="MESH" xml:lang="en">
<term>Crystallography, X-Ray</term>
<term>Microbial Sensitivity Tests</term>
<term>Models, Molecular</term>
<term>Molecular Structure</term>
<term>Phylogeny</term>
<term>Quantum Theory</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr">
<term>Cristallographie aux rayons X</term>
<term>Modèles moléculaires</term>
<term>Phylogenèse</term>
<term>Structure moléculaire</term>
<term>Tests de sensibilité microbienne</term>
<term>Théorie quantique</term>
</keywords>
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<front>
<div type="abstract" xml:lang="en">For the first time, the pigment composition of basidiocarps from the Chilean mushroom Cortinarius pyromyxa was studied under various aspects like phylogeny, chemistry and antibiotic activity. A molecular biological study supports the monotypic position of C. pyromyxa in subgenus Myxacium, genus Cortinarius. Four undescribed diterpenoids, named pyromyxones A-D, were isolated from fruiting bodies of C. pyromyxa. Their chemical structures were elucidated based on comprehensive one- and two-dimensional NMR spectroscopic analysis, ESI-HRMS measurements, as well as X-ray crystallography. In addition, the absolute configurations of pyromyxones A-D were established with the aid of J
<sub>H,H</sub>
, NOESY spectra and quantum chemical CD calculation. The pyromyxones A-D possess the undescribed nor-guanacastane skeleton. Tested pyromyxones A, B, and D exhibit only weak activity against gram-positive Bacillus subtilis and gram-negative Aliivibrio fischeri as well as the phytopathogenic fungi Botrytis cinerea, Septoria tritici and Phytophthora infestans.</div>
</front>
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<DateCompleted>
<Year>2019</Year>
<Month>08</Month>
<Day>15</Day>
</DateCompleted>
<DateRevised>
<Year>2019</Year>
<Month>08</Month>
<Day>15</Day>
</DateRevised>
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<Journal>
<ISSN IssnType="Electronic">1873-3700</ISSN>
<JournalIssue CitedMedium="Internet">
<Volume>165</Volume>
<PubDate>
<Year>2019</Year>
<Month>Sep</Month>
</PubDate>
</JournalIssue>
<Title>Phytochemistry</Title>
<ISOAbbreviation>Phytochemistry</ISOAbbreviation>
</Journal>
<ArticleTitle>Nor-guanacastepene pigments from the Chilean mushroom Cortinarius pyromyxa.</ArticleTitle>
<Pagination>
<MedlinePgn>112048</MedlinePgn>
</Pagination>
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<ELocationID EIdType="doi" ValidYN="Y">10.1016/j.phytochem.2019.05.021</ELocationID>
<Abstract>
<AbstractText>For the first time, the pigment composition of basidiocarps from the Chilean mushroom Cortinarius pyromyxa was studied under various aspects like phylogeny, chemistry and antibiotic activity. A molecular biological study supports the monotypic position of C. pyromyxa in subgenus Myxacium, genus Cortinarius. Four undescribed diterpenoids, named pyromyxones A-D, were isolated from fruiting bodies of C. pyromyxa. Their chemical structures were elucidated based on comprehensive one- and two-dimensional NMR spectroscopic analysis, ESI-HRMS measurements, as well as X-ray crystallography. In addition, the absolute configurations of pyromyxones A-D were established with the aid of J
<sub>H,H</sub>
, NOESY spectra and quantum chemical CD calculation. The pyromyxones A-D possess the undescribed nor-guanacastane skeleton. Tested pyromyxones A, B, and D exhibit only weak activity against gram-positive Bacillus subtilis and gram-negative Aliivibrio fischeri as well as the phytopathogenic fungi Botrytis cinerea, Septoria tritici and Phytophthora infestans.</AbstractText>
<CopyrightInformation>Copyright © 2019 Elsevier Ltd. All rights reserved.</CopyrightInformation>
</Abstract>
<AuthorList CompleteYN="Y">
<Author ValidYN="Y">
<LastName>Lam</LastName>
<ForeName>Yen T H</ForeName>
<Initials>YTH</Initials>
<AffiliationInfo>
<Affiliation>Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle (Saale), Germany.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Palfner</LastName>
<ForeName>Götz</ForeName>
<Initials>G</Initials>
<AffiliationInfo>
<Affiliation>Departamento de Botanica, Facultad de CienciasNaturales y Oceanograficas, Universidad de Concepción, Casilla 160-C, Concepción, Chile.</Affiliation>
</AffiliationInfo>
</Author>
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<LastName>Lima</LastName>
<ForeName>Celia</ForeName>
<Initials>C</Initials>
<AffiliationInfo>
<Affiliation>Departamento de Microbiología, Facultad de CienciasBiológicas, Universidad de Concepción, Concepción, Casilla 160-C, Concepción, Chile.</Affiliation>
</AffiliationInfo>
</Author>
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<LastName>Porzel</LastName>
<ForeName>Andrea</ForeName>
<Initials>A</Initials>
<AffiliationInfo>
<Affiliation>Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle (Saale), Germany.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Brandt</LastName>
<ForeName>Wolfgang</ForeName>
<Initials>W</Initials>
<AffiliationInfo>
<Affiliation>Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle (Saale), Germany.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Frolov</LastName>
<ForeName>Andrej</ForeName>
<Initials>A</Initials>
<AffiliationInfo>
<Affiliation>Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle (Saale), Germany; St. Petersburg State University, Faculty of Biology, Department of Biochemistry, Sredny Prospekt V.O. 41, 199004, St. Petersburg, Russian Federation.</Affiliation>
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<Author ValidYN="Y">
<LastName>Sultani</LastName>
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<Initials>H</Initials>
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<Affiliation>Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle (Saale), Germany.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Franke</LastName>
<ForeName>Katrin</ForeName>
<Initials>K</Initials>
<AffiliationInfo>
<Affiliation>Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle (Saale), Germany.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Wagner</LastName>
<ForeName>Christoph</ForeName>
<Initials>C</Initials>
<AffiliationInfo>
<Affiliation>Institute of Chemistry, Faculty of Natural Sciences II, Martin Luther University Halle-Wittenberg, Kurt-Mothes-Str.2, D-06120, Halle (Saale), Germany.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Merzweiler</LastName>
<ForeName>Kurt</ForeName>
<Initials>K</Initials>
<AffiliationInfo>
<Affiliation>Institute of Chemistry, Faculty of Natural Sciences II, Martin Luther University Halle-Wittenberg, Kurt-Mothes-Str.2, D-06120, Halle (Saale), Germany.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Wessjohann</LastName>
<ForeName>Ludger A</ForeName>
<Initials>LA</Initials>
<AffiliationInfo>
<Affiliation>Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle (Saale), Germany.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Arnold</LastName>
<ForeName>Norbert</ForeName>
<Initials>N</Initials>
<AffiliationInfo>
<Affiliation>Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle (Saale), Germany. Electronic address: Norbert.Arnold@ipb-halle.de.</Affiliation>
</AffiliationInfo>
</Author>
</AuthorList>
<Language>eng</Language>
<PublicationTypeList>
<PublicationType UI="D016428">Journal Article</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic">
<Year>2019</Year>
<Month>06</Month>
<Day>21</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo>
<Country>England</Country>
<MedlineTA>Phytochemistry</MedlineTA>
<NlmUniqueID>0151434</NlmUniqueID>
<ISSNLinking>0031-9422</ISSNLinking>
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<ChemicalList>
<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000900">Anti-Bacterial Agents</NameOfSubstance>
</Chemical>
<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D004224">Diterpenes</NameOfSubstance>
</Chemical>
<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D010860">Pigments, Biological</NameOfSubstance>
</Chemical>
<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="C409194">guanacastepene</NameOfSubstance>
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<CitationSubset>IM</CitationSubset>
<MeshHeadingList>
<MeshHeading>
<DescriptorName UI="D000900" MajorTopicYN="N">Anti-Bacterial Agents</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D055363" MajorTopicYN="N">Cortinarius</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D018360" MajorTopicYN="N">Crystallography, X-Ray</DescriptorName>
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<MeshHeading>
<DescriptorName UI="D004224" MajorTopicYN="N">Diterpenes</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName>
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<MeshHeading>
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<MeshHeading>
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<Keyword MajorTopicYN="N">Cortinariaceae</Keyword>
<Keyword MajorTopicYN="N">Cortinarius pyromyxa M. M. Moser & E. Horak</Keyword>
<Keyword MajorTopicYN="N">Diterpenoids</Keyword>
<Keyword MajorTopicYN="N">Fungal fruiting bodies</Keyword>
<Keyword MajorTopicYN="N">Nor-guanacastepenes</Keyword>
<Keyword MajorTopicYN="N">Phylogeny</Keyword>
<Keyword MajorTopicYN="N">Pyromyxones</Keyword>
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<Month>03</Month>
<Day>20</Day>
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<Year>2019</Year>
<Month>05</Month>
<Day>30</Day>
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<Month>05</Month>
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