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Isolation and structural elucidation of a novel brunnein-type antioxidant β-carboline alkaloid from Cyclocybe cylindracea.

Identifieur interne : 000864 ( Main/Exploration ); précédent : 000863; suivant : 000865

Isolation 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 :

RBID : pubmed:31150766

Descripteurs français

English descriptors

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:


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Le document en format XML

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<term>Carbolines (isolation & purification)</term>
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<term>Free Radical Scavengers (isolation & purification)</term>
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<term>Carbolines (composition chimique)</term>
<term>Carbolines (isolement et purification)</term>
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<term>Piégeurs de radicaux libres (composition chimique)</term>
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<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>
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<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>
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<NlmUniqueID>16930290R</NlmUniqueID>
<ISSNLinking>0367-326X</ISSNLinking>
</MedlineJournalInfo>
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<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000470">Alkaloids</NameOfSubstance>
</Chemical>
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<Chemical>
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</Chemical>
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<NameOfSubstance UI="C524296">brunnein B</NameOfSubstance>
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<DescriptorName UI="D000363" MajorTopicYN="N">Agaricales</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName>
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<MeshHeading>
<DescriptorName UI="D000470" MajorTopicYN="N">Alkaloids</DescriptorName>
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</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>
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<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>
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<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>
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<Year>2019</Year>
<Month>6</Month>
<Day>1</Day>
<Hour>6</Hour>
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<Month>9</Month>
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<Minute>0</Minute>
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<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>
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</pubmed>
<affiliations>
<list>
<country>
<li>Hongrie</li>
</country>
<region>
<li>Hongrie centrale</li>
</region>
<settlement>
<li>Budapest</li>
</settlement>
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<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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