Metabolites from the Endophytic Fungus Curvularia sp. M12 Act as Motility Inhibitors against Phytophthora capsici Zoospores.
Identifieur interne : 000969 ( Main/Exploration ); précédent : 000968; suivant : 000970Metabolites from the Endophytic Fungus Curvularia sp. M12 Act as Motility Inhibitors against Phytophthora capsici Zoospores.
Auteurs : Muhammad Abdul Mojid Mondol [Allemagne] ; Jannatul Farthouse [Bangladesh] ; Mohammad Tofazzal Islam [Bangladesh] ; Anja Schüffler [Allemagne] ; Hartmut Laatsch [Allemagne]Source :
- Journal of natural products [ 1520-6025 ] ; 2017.
Descripteurs français
- KwdFr :
- Ascomycota (composition chimique), Bangladesh (MeSH), Feuilles de plante (microbiologie), Isocoumarines (MeSH), Murraya (microbiologie), Phytophthora (effets des médicaments et des substances chimiques), Plantes médicinales (microbiologie), Relation dose-effet des médicaments (MeSH), Résonance magnétique nucléaire biomoléculaire (MeSH), Structure moléculaire (MeSH).
- MESH :
- composition chimique : Ascomycota.
- effets des médicaments et des substances chimiques : Phytophthora.
- microbiologie : Feuilles de plante, Murraya, Plantes médicinales.
- Bangladesh, Isocoumarines, Relation dose-effet des médicaments, Résonance magnétique nucléaire biomoléculaire, Structure moléculaire.
English descriptors
- KwdEn :
- MESH :
- chemical : Isocoumarins.
- chemistry : Ascomycota.
- drug effects : Phytophthora.
- microbiology : Murraya, Plant Leaves, Plants, Medicinal.
- Bangladesh, Dose-Response Relationship, Drug, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular.
Abstract
The endophytic fungus Curvularia sp., strain M12, was isolated from a leaf of the medicinal plant Murraya koenigii and cultured on rice medium followed by chemical screening of the culture extract. Chromatographic analysis led to the isolation of four new compounds, murranofuran A (1), murranolide A (2), murranopyrone (3a), and murranoic acid A (4a), along with six known metabolites, N-(2-hydroxy-6-methoxyphenyl)acetamide (5), curvularin (6), (S)-dehydrocurvularin (7), pyrenolide A (8), modiolide A (9), and 8-hydroxy-6-methoxy-3-methylisocoumarin (10). The structures of the known compounds were confirmed by comparing ESI HR mass spectra, 1H and 13C NMR, and optical rotation data with values reported in the literature. The planar structures of the new compounds were elucidated by extensive analysis of 1D and 2D NMR and mass data. The absolute configurations of the new compounds were established by coupling constant analysis, modified Mosher's method, and CD data. Compound 8 showed a strong motility impairing activity against Phytophthora capsici zoospores at a low concentration (100% at 0.5 μg/mL) in a short time (30 min). Compounds 2, 3a, 6, 7, 9, and 10 exhibited zoospore motility impairment activity at higher concentrations (IC50: 50-100 μg/mL).
DOI: 10.1021/acs.jnatprod.6b00785
PubMed: 28195475
Affiliations:
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M12 Act as Motility Inhibitors against Phytophthora capsici Zoospores.</title><author><name sortKey="Mondol, Muhammad Abdul Mojid" sort="Mondol, Muhammad Abdul Mojid" uniqKey="Mondol M" first="Muhammad Abdul Mojid" last="Mondol">Muhammad Abdul Mojid Mondol</name><affiliation wicri:level="3"><nlm:affiliation>Institute for Organic and Biomolecular Chemistry, Georg-August-University Göttingen , Tamannstrasse 2, D-37077 Göttingen, Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Institute for Organic and Biomolecular Chemistry, Georg-August-University Göttingen , Tamannstrasse 2, D-37077 Göttingen</wicri:regionArea><placeName><region type="land" nuts="2">Basse-Saxe</region><settlement type="city">Göttingen</settlement></placeName></affiliation></author><author><name sortKey="Farthouse, Jannatul" sort="Farthouse, Jannatul" uniqKey="Farthouse J" first="Jannatul" last="Farthouse">Jannatul Farthouse</name><affiliation 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(microbiology)</term><term>Plants, Medicinal (microbiology)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Ascomycota (composition chimique)</term><term>Bangladesh (MeSH)</term><term>Feuilles de plante (microbiologie)</term><term>Isocoumarines (MeSH)</term><term>Murraya (microbiologie)</term><term>Phytophthora (effets des médicaments et des substances chimiques)</term><term>Plantes médicinales (microbiologie)</term><term>Relation dose-effet des médicaments (MeSH)</term><term>Résonance magnétique nucléaire biomoléculaire (MeSH)</term><term>Structure moléculaire (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Isocoumarins</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Ascomycota</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Ascomycota</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Phytophthora</term></keywords><keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Phytophthora</term></keywords><keywords scheme="MESH" qualifier="microbiologie" xml:lang="fr"><term>Feuilles de plante</term><term>Murraya</term><term>Plantes médicinales</term></keywords><keywords scheme="MESH" qualifier="microbiology" xml:lang="en"><term>Murraya</term><term>Plant Leaves</term><term>Plants, Medicinal</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Bangladesh</term><term>Dose-Response Relationship, Drug</term><term>Molecular Structure</term><term>Nuclear Magnetic Resonance, Biomolecular</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Bangladesh</term><term>Isocoumarines</term><term>Relation dose-effet des médicaments</term><term>Résonance magnétique nucléaire biomoléculaire</term><term>Structure moléculaire</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The endophytic fungus Curvularia sp., strain M12, was isolated from a leaf of the medicinal plant Murraya koenigii and cultured on rice medium followed by chemical screening of the culture extract. Chromatographic analysis led to the isolation of four new compounds, murranofuran A (1), murranolide A (2), murranopyrone (3a), and murranoic acid A (4a), along with six known metabolites, N-(2-hydroxy-6-methoxyphenyl)acetamide (5), curvularin (6), (S)-dehydrocurvularin (7), pyrenolide A (8), modiolide A (9), and 8-hydroxy-6-methoxy-3-methylisocoumarin (10). The structures of the known compounds were confirmed by comparing ESI HR mass spectra, <sup>1</sup>H and <sup>13</sup>C NMR, and optical rotation data with values reported in the literature. The planar structures of the new compounds were elucidated by extensive analysis of 1D and 2D NMR and mass data. The absolute configurations of the new compounds were established by coupling constant analysis, modified Mosher's method, and CD data. Compound 8 showed a strong motility impairing activity against Phytophthora capsici zoospores at a low concentration (100% at 0.5 μg/mL) in a short time (30 min). Compounds 2, 3a, 6, 7, 9, and 10 exhibited zoospore motility impairment activity at higher concentrations (IC<sub>50</sub>: 50-100 μg/mL).</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">28195475</PMID><DateCompleted><Year>2017</Year><Month>07</Month><Day>14</Day></DateCompleted><DateRevised><Year>2018</Year><Month>10</Month><Day>28</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6025</ISSN><JournalIssue CitedMedium="Internet"><Volume>80</Volume><Issue>2</Issue><PubDate><Year>2017</Year><Month>02</Month><Day>24</Day></PubDate></JournalIssue><Title>Journal of natural products</Title><ISOAbbreviation>J Nat Prod</ISOAbbreviation></Journal><ArticleTitle>Metabolites from the Endophytic Fungus Curvularia sp. M12 Act as Motility Inhibitors against Phytophthora capsici Zoospores.</ArticleTitle><Pagination><MedlinePgn>347-355</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.jnatprod.6b00785</ELocationID><Abstract><AbstractText>The endophytic fungus Curvularia sp., strain M12, was isolated from a leaf of the medicinal plant Murraya koenigii and cultured on rice medium followed by chemical screening of the culture extract. Chromatographic analysis led to the isolation of four new compounds, murranofuran A (1), murranolide A (2), murranopyrone (3a), and murranoic acid A (4a), along with six known metabolites, N-(2-hydroxy-6-methoxyphenyl)acetamide (5), curvularin (6), (S)-dehydrocurvularin (7), pyrenolide A (8), modiolide A (9), and 8-hydroxy-6-methoxy-3-methylisocoumarin (10). The structures of the known compounds were confirmed by comparing ESI HR mass spectra, <sup>1</sup>H and <sup>13</sup>C NMR, and optical rotation data with values reported in the literature. The planar structures of the new compounds were elucidated by extensive analysis of 1D and 2D NMR and mass data. The absolute configurations of the new compounds were established by coupling constant analysis, modified Mosher's method, and CD data. Compound 8 showed a strong motility impairing activity against Phytophthora capsici zoospores at a low concentration (100% at 0.5 μg/mL) in a short time (30 min). Compounds 2, 3a, 6, 7, 9, and 10 exhibited zoospore motility impairment activity at higher concentrations (IC<sub>50</sub>: 50-100 μg/mL).</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Mondol</LastName><ForeName>Muhammad Abdul Mojid</ForeName><Initials>MA</Initials><Identifier Source="ORCID">0000-0002-8495-4498</Identifier><AffiliationInfo><Affiliation>Institute for Organic and Biomolecular Chemistry, Georg-August-University Göttingen , Tamannstrasse 2, D-37077 Göttingen, Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Farthouse</LastName><ForeName>Jannatul</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Department of Biotechnology, Bangabandhu Sheikh Mujibur Rahman Agricultural University , Gazipur-1706, Bangladesh.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Islam</LastName><ForeName>Mohammad Tofazzal</ForeName><Initials>MT</Initials><AffiliationInfo><Affiliation>Department of Biotechnology, Bangabandhu Sheikh Mujibur Rahman Agricultural University , Gazipur-1706, Bangladesh.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Schüffler</LastName><ForeName>Anja</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Institute of Biotechnology and Drug Research , D-67663 Kaiserslautern, Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Laatsch</LastName><ForeName>Hartmut</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>Institute for Organic and Biomolecular Chemistry, Georg-August-University Göttingen , Tamannstrasse 2, D-37077 Göttingen, Germany.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2017</Year><Month>02</Month><Day>14</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Nat Prod</MedlineTA><NlmUniqueID>7906882</NlmUniqueID><ISSNLinking>0163-3864</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C540304">8-hydroxy-6-methoxy-3-methylisocoumarin</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D049934">Isocoumarins</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D001203" MajorTopicYN="N">Ascomycota</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001459" MajorTopicYN="N">Bangladesh</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004305" MajorTopicYN="N">Dose-Response Relationship, Drug</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D049934" MajorTopicYN="N">Isocoumarins</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D032101" MajorTopicYN="N">Murraya</DescriptorName><QualifierName UI="Q000382" MajorTopicYN="N">microbiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D019906" MajorTopicYN="N">Nuclear Magnetic Resonance, Biomolecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010838" MajorTopicYN="N">Phytophthora</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D018515" MajorTopicYN="N">Plant Leaves</DescriptorName><QualifierName UI="Q000382" MajorTopicYN="N">microbiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010946" MajorTopicYN="N">Plants, Medicinal</DescriptorName><QualifierName UI="Q000382" MajorTopicYN="N">microbiology</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2017</Year><Month>2</Month><Day>15</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2017</Year><Month>7</Month><Day>15</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2017</Year><Month>2</Month><Day>15</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">28195475</ArticleId><ArticleId IdType="doi">10.1021/acs.jnatprod.6b00785</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Allemagne</li><li>Bangladesh</li></country><region><li>Basse-Saxe</li><li>Rhénanie-Palatinat</li></region><settlement><li>Göttingen</li><li>Kaiserslautern</li></settlement></list><tree><country name="Allemagne"><region name="Basse-Saxe"><name sortKey="Mondol, Muhammad Abdul Mojid" sort="Mondol, Muhammad Abdul Mojid" uniqKey="Mondol M" first="Muhammad Abdul Mojid" last="Mondol">Muhammad Abdul Mojid Mondol</name></region><name sortKey="Laatsch, Hartmut" sort="Laatsch, Hartmut" uniqKey="Laatsch H" first="Hartmut" last="Laatsch">Hartmut Laatsch</name><name sortKey="Schuffler, Anja" sort="Schuffler, Anja" uniqKey="Schuffler A" first="Anja" last="Schüffler">Anja Schüffler</name></country><country name="Bangladesh"><noRegion><name sortKey="Farthouse, Jannatul" sort="Farthouse, Jannatul" uniqKey="Farthouse J" first="Jannatul" last="Farthouse">Jannatul Farthouse</name></noRegion><name sortKey="Islam, Mohammad Tofazzal" sort="Islam, Mohammad Tofazzal" uniqKey="Islam M" first="Mohammad Tofazzal" last="Islam">Mohammad Tofazzal Islam</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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