Isolation and structural elucidation of a novel brunnein-type antioxidant β-carboline alkaloid from Cyclocybe cylindracea.
Identifieur interne : 000864 ( Main/Exploration ); précédent : 000863; suivant : 000865Isolation and structural elucidation of a novel brunnein-type antioxidant β-carboline alkaloid from Cyclocybe cylindracea.
Auteurs : Dániel Krüzselyi [Hongrie] ; János Vetter [Hongrie] ; Péter G. Ott [Hongrie] ; András Darcsi [Hongrie] ; Szabolcs Béni [Hongrie] ; Ágnes Gömöry [Hongrie] ; Lászl Drahos [Hongrie] ; Ferenc Zsila [Hongrie] ; Ágnes M. M Ricz [Hongrie]Source :
- Fitoterapia [ 1873-6971 ] ; 2019.
Descripteurs français
- KwdFr :
- Agaricales (composition chimique), Alcaloïdes (composition chimique), Alcaloïdes (isolement et purification), Carbolines (composition chimique), Carbolines (isolement et purification), Hongrie (MeSH), Piégeurs de radicaux libres (composition chimique), Piégeurs de radicaux libres (isolement et purification), Structure moléculaire (MeSH).
- MESH :
- composition chimique : Agaricales, Alcaloïdes, Carbolines, Piégeurs de radicaux libres.
- isolement et purification : Alcaloïdes, Carbolines, Piégeurs de radicaux libres.
- Hongrie, Structure moléculaire.
- Wicri :
- geographic : Hongrie.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Alkaloids, Carbolines, Free Radical Scavengers.
- geographic : Hungary.
- chemistry : Agaricales.
- chemical , isolation & purification : Alkaloids, Carbolines, Free Radical Scavengers.
- Molecular Structure.
Abstract
Effect-directed isolation of free radical scavengers from the methanol extract of the freeze-dried fruiting bodies of the cultivated basidiomycetous mushroom, black poplar (Cyclocybe cylindracea), yielded a β-carboline alkaloid. Its structure was determined based on ESI-TOF-MS/MS, NMR and circular dichroism spectra by comparison with published data. The compound, identified as the C1-S diastereomer of brunnein B, exhibited explicit radical scavenging activity (EC50 = 119.1 ± 1.2 μg/mL). The quantity of the active component was determined with HPLC-MS in the fruiting body (36.2 ± 2.8 ng/g DW, dry weight) and its different tissues such as peel (94.7 ± 1.9 ng/g DW), inner cap (90.5 ± 1.3 ng/g DW), gills (71.5 ± 0.6 ng/g DW), and stipe (162.2 ± 1.7 ng/g DW). It is a β-carboline alkaloid that was not reported previously.
DOI: 10.1016/j.fitote.2019.104180
PubMed: 31150766
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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<term>Alkaloids (chemistry)</term>
<term>Alkaloids (isolation & purification)</term>
<term>Carbolines (chemistry)</term>
<term>Carbolines (isolation & purification)</term>
<term>Free Radical Scavengers (chemistry)</term>
<term>Free Radical Scavengers (isolation & purification)</term>
<term>Hungary (MeSH)</term>
<term>Molecular Structure (MeSH)</term>
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<term>Alcaloïdes (composition chimique)</term>
<term>Alcaloïdes (isolement et purification)</term>
<term>Carbolines (composition chimique)</term>
<term>Carbolines (isolement et purification)</term>
<term>Hongrie (MeSH)</term>
<term>Piégeurs de radicaux libres (composition chimique)</term>
<term>Piégeurs de radicaux libres (isolement et purification)</term>
<term>Structure moléculaire (MeSH)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Alkaloids</term>
<term>Carbolines</term>
<term>Free Radical Scavengers</term>
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<keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Agaricales</term>
</keywords>
<keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Agaricales</term>
<term>Alcaloïdes</term>
<term>Carbolines</term>
<term>Piégeurs de radicaux libres</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Alkaloids</term>
<term>Carbolines</term>
<term>Free Radical Scavengers</term>
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<term>Carbolines</term>
<term>Piégeurs de radicaux libres</term>
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<keywords scheme="MESH" xml:lang="en"><term>Molecular Structure</term>
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<term>Structure moléculaire</term>
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<front><div type="abstract" xml:lang="en">Effect-directed isolation of free radical scavengers from the methanol extract of the freeze-dried fruiting bodies of the cultivated basidiomycetous mushroom, black poplar (Cyclocybe cylindracea), yielded a β-carboline alkaloid. Its structure was determined based on ESI-TOF-MS/MS, NMR and circular dichroism spectra by comparison with published data. The compound, identified as the C1-S diastereomer of brunnein B, exhibited explicit radical scavenging activity (EC<sub>50</sub>
= 119.1 ± 1.2 μg/mL). The quantity of the active component was determined with HPLC-MS in the fruiting body (36.2 ± 2.8 ng/g DW, dry weight) and its different tissues such as peel (94.7 ± 1.9 ng/g DW), inner cap (90.5 ± 1.3 ng/g DW), gills (71.5 ± 0.6 ng/g DW), and stipe (162.2 ± 1.7 ng/g DW). It is a β-carboline alkaloid that was not reported previously.</div>
</front>
</TEI>
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<DateCompleted><Year>2019</Year>
<Month>09</Month>
<Day>06</Day>
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<DateRevised><Year>2019</Year>
<Month>09</Month>
<Day>06</Day>
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<Month>Sep</Month>
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</JournalIssue>
<Title>Fitoterapia</Title>
<ISOAbbreviation>Fitoterapia</ISOAbbreviation>
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<ArticleTitle>Isolation and structural elucidation of a novel brunnein-type antioxidant β-carboline alkaloid from Cyclocybe cylindracea.</ArticleTitle>
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<Abstract><AbstractText>Effect-directed isolation of free radical scavengers from the methanol extract of the freeze-dried fruiting bodies of the cultivated basidiomycetous mushroom, black poplar (Cyclocybe cylindracea), yielded a β-carboline alkaloid. Its structure was determined based on ESI-TOF-MS/MS, NMR and circular dichroism spectra by comparison with published data. The compound, identified as the C1-S diastereomer of brunnein B, exhibited explicit radical scavenging activity (EC<sub>50</sub>
= 119.1 ± 1.2 μg/mL). The quantity of the active component was determined with HPLC-MS in the fruiting body (36.2 ± 2.8 ng/g DW, dry weight) and its different tissues such as peel (94.7 ± 1.9 ng/g DW), inner cap (90.5 ± 1.3 ng/g DW), gills (71.5 ± 0.6 ng/g DW), and stipe (162.2 ± 1.7 ng/g DW). It is a β-carboline alkaloid that was not reported previously.</AbstractText>
<CopyrightInformation>Copyright © 2019 Elsevier B.V. All rights reserved.</CopyrightInformation>
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<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Krüzselyi</LastName>
<ForeName>Dániel</ForeName>
<Initials>D</Initials>
<AffiliationInfo><Affiliation>Plant Protection Institute, Centre for Agricultural Research, Hungarian Academy of Sciences, Herman O. Str. 15, 1022 Budapest, Hungary.</Affiliation>
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<Author ValidYN="Y"><LastName>Béni</LastName>
<ForeName>Szabolcs</ForeName>
<Initials>S</Initials>
<AffiliationInfo><Affiliation>Department of Pharmacognosy, Semmelweis University, Üllői Str. 26, 1085 Budapest, Hungary.</Affiliation>
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<ForeName>Ágnes</ForeName>
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<AffiliationInfo><Affiliation>Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok Boulevard 2, 1117 Budapest, Hungary.</Affiliation>
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<Author ValidYN="Y"><LastName>Drahos</LastName>
<ForeName>László</ForeName>
<Initials>L</Initials>
<AffiliationInfo><Affiliation>Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok Boulevard 2, 1117 Budapest, Hungary.</Affiliation>
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<Initials>F</Initials>
<AffiliationInfo><Affiliation>Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok Boulevard 2, 1117 Budapest, Hungary.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Móricz</LastName>
<ForeName>Ágnes M</ForeName>
<Initials>ÁM</Initials>
<AffiliationInfo><Affiliation>Plant Protection Institute, Centre for Agricultural Research, Hungarian Academy of Sciences, Herman O. Str. 15, 1022 Budapest, Hungary. Electronic address: moricz.agnes@agrar.mta.hu.</Affiliation>
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<Month>05</Month>
<Day>29</Day>
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<NameOfSubstance UI="D016166">Free Radical Scavengers</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="C524296">brunnein B</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName UI="D000363" MajorTopicYN="N">Agaricales</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D000470" MajorTopicYN="N">Alkaloids</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName>
<QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D002243" MajorTopicYN="N">Carbolines</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName>
<QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D016166" MajorTopicYN="N">Free Radical Scavengers</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName>
<QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006814" MajorTopicYN="N" Type="Geographic">Hungary</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Antioxidant</Keyword>
<Keyword MajorTopicYN="N">Black poplar (Cyclocybe cylindracea)</Keyword>
<Keyword MajorTopicYN="N">C1-S diastereomer of brunnein B</Keyword>
<Keyword MajorTopicYN="N">Effect-directed isolation</Keyword>
<Keyword MajorTopicYN="N">Mushroom</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2019</Year>
<Month>04</Month>
<Day>12</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="revised"><Year>2019</Year>
<Month>05</Month>
<Day>25</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="accepted"><Year>2019</Year>
<Month>05</Month>
<Day>27</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed"><Year>2019</Year>
<Month>6</Month>
<Day>1</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2019</Year>
<Month>9</Month>
<Day>7</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2019</Year>
<Month>6</Month>
<Day>1</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">31150766</ArticleId>
<ArticleId IdType="pii">S0367-326X(19)30827-5</ArticleId>
<ArticleId IdType="doi">10.1016/j.fitote.2019.104180</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
<affiliations><list><country><li>Hongrie</li>
</country>
<region><li>Hongrie centrale</li>
</region>
<settlement><li>Budapest</li>
</settlement>
</list>
<tree><country name="Hongrie"><region name="Hongrie centrale"><name sortKey="Kruzselyi, Daniel" sort="Kruzselyi, Daniel" uniqKey="Kruzselyi D" first="Dániel" last="Krüzselyi">Dániel Krüzselyi</name>
</region>
<name sortKey="Beni, Szabolcs" sort="Beni, Szabolcs" uniqKey="Beni S" first="Szabolcs" last="Béni">Szabolcs Béni</name>
<name sortKey="Darcsi, Andras" sort="Darcsi, Andras" uniqKey="Darcsi A" first="András" last="Darcsi">András Darcsi</name>
<name sortKey="Drahos, Laszl" sort="Drahos, Laszl" uniqKey="Drahos L" first="Lászl" last="Drahos">Lászl Drahos</name>
<name sortKey="Gomory, Agnes" sort="Gomory, Agnes" uniqKey="Gomory A" first="Ágnes" last="Gömöry">Ágnes Gömöry</name>
<name sortKey="M Ricz, Agnes M" sort="M Ricz, Agnes M" uniqKey="M Ricz A" first="Ágnes M" last="M Ricz">Ágnes M. M Ricz</name>
<name sortKey="Ott, Peter G" sort="Ott, Peter G" uniqKey="Ott P" first="Péter G" last="Ott">Péter G. Ott</name>
<name sortKey="Vetter, Janos" sort="Vetter, Janos" uniqKey="Vetter J" first="János" last="Vetter">János Vetter</name>
<name sortKey="Zsila, Ferenc" sort="Zsila, Ferenc" uniqKey="Zsila F" first="Ferenc" last="Zsila">Ferenc Zsila</name>
</country>
</tree>
</affiliations>
</record>
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