Antifungal and antioomycete activities and modes of action of isobenzofuranones isolated from the endophytic fungus Hypoxylon anthochroum strain Gseg1.
Identifieur interne : 000298 ( Main/Exploration ); précédent : 000297; suivant : 000299Antifungal and antioomycete activities and modes of action of isobenzofuranones isolated from the endophytic fungus Hypoxylon anthochroum strain Gseg1.
Auteurs : Rosa Elvira Sánchez-Fernández [Mexique] ; Rosalía Sánchez-Fuentes [Mexique] ; Hiram Rangel-Sánchez [Mexique] ; Sim N Hernández-Ortega [Mexique] ; José G. L Pez-Cortés [Mexique] ; Martha Lydia Macías-Rubalcava [Mexique]Source :
- Pesticide biochemistry and physiology [ 1095-9939 ] ; 2020.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical : Antifungal Agents.
- Endophytes, Phytophthora, Pythium, Xylariales.
Abstract
Hypoxylon species are distributed worldwide and have been isolated from different habitats. The endophyte Hypoxylon anthochroum strain Gseg1 was isolated from healthy leaves of Gliricidia sepium. A chemical study of the culture medium and mycelium organic extracts of the endophytic fungus H. anthochroum Gseg1 led to the isolation of three known isobenzofuranones, 7-hydroxy-4,6-dimethyl-3H-isobenzofuran-1-one, 1, 7-methoxy-4,6-dimethyl-3H-isobenzofuran-1-one, 2, 6-formyl-4-methyl-7-methoxy-3H-isobenzofuran-1-one, 3, and one compound was isolated for the first time as a natural product, 7-methoxy-4-methyl-3H-isobenzofuran-1-one, 4. In addition, the chemical synthesis of 1 and 2, and a derivative, 7-methoxy-6-methyl-3H-isobenzofuran-1-one, 5, was performed. The isobenzofuranones showed antifungal and antioomycete activities. Compounds 1-5 inhibited the growth of Fusarium oxysporum, Alternaria alternata, Pythium aphanidermatum, and Phytophthora capsici, in addition, 1, 2 and 5 interrupted the respiration and caused electrolyte leakage due to cell membrane damage. Compound 2 was the most active, inhibiting the growth of the four microorganisms, affecting the respiration and increasing the relative conductivity due to electrolyte leakage. Compounds 1-4 also induce morphological changes in the plant pathogens' mycelia and hyphae. These compounds could be useful for the control of plant pathogenic fungi and oomycetes of agricultural relevance.
DOI: 10.1016/j.pestbp.2020.104670
PubMed: 32828376
Affiliations:
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L Pez-Cortés</name><affiliation wicri:level="1"><nlm:affiliation>Departamento de Química Inorgánica, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510, Mexico.</nlm:affiliation><country xml:lang="fr">Mexique</country><wicri:regionArea>Departamento de Química Inorgánica, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510</wicri:regionArea><wicri:noRegion>Ciudad de Mexico 04510</wicri:noRegion></affiliation></author><author><name sortKey="Macias Rubalcava, Martha Lydia" sort="Macias Rubalcava, Martha Lydia" uniqKey="Macias Rubalcava M" first="Martha Lydia" last="Macías-Rubalcava">Martha Lydia Macías-Rubalcava</name><affiliation wicri:level="1"><nlm:affiliation>Departamento de Productos Naturales, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510, Mexico. 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L Pez-Cortés</name><affiliation wicri:level="1"><nlm:affiliation>Departamento de Química Inorgánica, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510, Mexico.</nlm:affiliation><country xml:lang="fr">Mexique</country><wicri:regionArea>Departamento de Química Inorgánica, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510</wicri:regionArea><wicri:noRegion>Ciudad de Mexico 04510</wicri:noRegion></affiliation></author><author><name sortKey="Macias Rubalcava, Martha Lydia" sort="Macias Rubalcava, Martha Lydia" uniqKey="Macias Rubalcava M" first="Martha Lydia" last="Macías-Rubalcava">Martha Lydia Macías-Rubalcava</name><affiliation wicri:level="1"><nlm:affiliation>Departamento de Productos Naturales, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510, Mexico. Electronic address: mmacias@iquimica.unam.mx.</nlm:affiliation><country xml:lang="fr">Mexique</country><wicri:regionArea>Departamento de Productos Naturales, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510</wicri:regionArea><wicri:noRegion>Ciudad de Mexico 04510</wicri:noRegion></affiliation></author></analytic><series><title level="j">Pesticide biochemistry and physiology</title><idno type="eISSN">1095-9939</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antifungal Agents (MeSH)</term><term>Endophytes (MeSH)</term><term>Phytophthora (MeSH)</term><term>Pythium (MeSH)</term><term>Xylariales (MeSH)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antifongiques (MeSH)</term><term>Endophytes (MeSH)</term><term>Phytophthora (MeSH)</term><term>Pythium (MeSH)</term><term>Xylariales (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Antifungal Agents</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Endophytes</term><term>Phytophthora</term><term>Pythium</term><term>Xylariales</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Antifongiques</term><term>Endophytes</term><term>Phytophthora</term><term>Pythium</term><term>Xylariales</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Hypoxylon species are distributed worldwide and have been isolated from different habitats. The endophyte Hypoxylon anthochroum strain Gseg1 was isolated from healthy leaves of Gliricidia sepium. A chemical study of the culture medium and mycelium organic extracts of the endophytic fungus H. anthochroum Gseg1 led to the isolation of three known isobenzofuranones, 7-hydroxy-4,6-dimethyl-3H-isobenzofuran-1-one, 1, 7-methoxy-4,6-dimethyl-3H-isobenzofuran-1-one, 2, 6-formyl-4-methyl-7-methoxy-3H-isobenzofuran-1-one, 3, and one compound was isolated for the first time as a natural product, 7-methoxy-4-methyl-3H-isobenzofuran-1-one, 4. In addition, the chemical synthesis of 1 and 2, and a derivative, 7-methoxy-6-methyl-3H-isobenzofuran-1-one, 5, was performed. The isobenzofuranones showed antifungal and antioomycete activities. Compounds 1-5 inhibited the growth of Fusarium oxysporum, Alternaria alternata, Pythium aphanidermatum, and Phytophthora capsici, in addition, 1, 2 and 5 interrupted the respiration and caused electrolyte leakage due to cell membrane damage. Compound 2 was the most active, inhibiting the growth of the four microorganisms, affecting the respiration and increasing the relative conductivity due to electrolyte leakage. Compounds 1-4 also induce morphological changes in the plant pathogens' mycelia and hyphae. These compounds could be useful for the control of plant pathogenic fungi and oomycetes of agricultural relevance.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" IndexingMethod="Automated" Owner="NLM"><PMID Version="1">32828376</PMID><DateCompleted><Year>2020</Year><Month>08</Month><Day>25</Day></DateCompleted><DateRevised><Year>2020</Year><Month>08</Month><Day>25</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1095-9939</ISSN><JournalIssue CitedMedium="Internet"><Volume>169</Volume><PubDate><Year>2020</Year><Month>Oct</Month></PubDate></JournalIssue><Title>Pesticide biochemistry and physiology</Title><ISOAbbreviation>Pestic Biochem Physiol</ISOAbbreviation></Journal><ArticleTitle>Antifungal and antioomycete activities and modes of action of isobenzofuranones isolated from the endophytic fungus Hypoxylon anthochroum strain Gseg1.</ArticleTitle><Pagination><MedlinePgn>104670</MedlinePgn></Pagination><ELocationID EIdType="pii" ValidYN="Y">S0048-3575(20)30165-6</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.pestbp.2020.104670</ELocationID><Abstract><AbstractText>Hypoxylon species are distributed worldwide and have been isolated from different habitats. The endophyte Hypoxylon anthochroum strain Gseg1 was isolated from healthy leaves of Gliricidia sepium. A chemical study of the culture medium and mycelium organic extracts of the endophytic fungus H. anthochroum Gseg1 led to the isolation of three known isobenzofuranones, 7-hydroxy-4,6-dimethyl-3H-isobenzofuran-1-one, 1, 7-methoxy-4,6-dimethyl-3H-isobenzofuran-1-one, 2, 6-formyl-4-methyl-7-methoxy-3H-isobenzofuran-1-one, 3, and one compound was isolated for the first time as a natural product, 7-methoxy-4-methyl-3H-isobenzofuran-1-one, 4. In addition, the chemical synthesis of 1 and 2, and a derivative, 7-methoxy-6-methyl-3H-isobenzofuran-1-one, 5, was performed. The isobenzofuranones showed antifungal and antioomycete activities. Compounds 1-5 inhibited the growth of Fusarium oxysporum, Alternaria alternata, Pythium aphanidermatum, and Phytophthora capsici, in addition, 1, 2 and 5 interrupted the respiration and caused electrolyte leakage due to cell membrane damage. Compound 2 was the most active, inhibiting the growth of the four microorganisms, affecting the respiration and increasing the relative conductivity due to electrolyte leakage. Compounds 1-4 also induce morphological changes in the plant pathogens' mycelia and hyphae. These compounds could be useful for the control of plant pathogenic fungi and oomycetes of agricultural relevance.</AbstractText><CopyrightInformation>Copyright © 2020 Elsevier Inc. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Sánchez-Fernández</LastName><ForeName>Rosa Elvira</ForeName><Initials>RE</Initials><AffiliationInfo><Affiliation>Departamento de Productos Naturales, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Sánchez-Fuentes</LastName><ForeName>Rosalía</ForeName><Initials>R</Initials><AffiliationInfo><Affiliation>Departamento de Productos Naturales, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Rangel-Sánchez</LastName><ForeName>Hiram</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>Departamento de Química Inorgánica, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hernández-Ortega</LastName><ForeName>Simón</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Laboratorio de Rayos X, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>López-Cortés</LastName><ForeName>José G</ForeName><Initials>JG</Initials><AffiliationInfo><Affiliation>Departamento de Química Inorgánica, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510, Mexico.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Macías-Rubalcava</LastName><ForeName>Martha Lydia</ForeName><Initials>ML</Initials><AffiliationInfo><Affiliation>Departamento de Productos Naturales, Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Delegación Coyoacán, Ciudad de Mexico 04510, Mexico. Electronic address: mmacias@iquimica.unam.mx.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>07</Month><Day>26</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Pestic Biochem Physiol</MedlineTA><NlmUniqueID>1301573</NlmUniqueID><ISSNLinking>0048-3575</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000935">Antifungal Agents</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000935" MajorTopicYN="N">Antifungal Agents</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D060026" MajorTopicYN="N">Endophytes</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010838" MajorTopicYN="Y">Phytophthora</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011775" MajorTopicYN="Y">Pythium</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013098" MajorTopicYN="Y">Xylariales</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Antifungal</Keyword><Keyword MajorTopicYN="N">Antioomycete</Keyword><Keyword MajorTopicYN="N">Endophyte</Keyword><Keyword MajorTopicYN="N">Hypoxylon anthochroum</Keyword><Keyword MajorTopicYN="N">Isobenzofuranones</Keyword><Keyword MajorTopicYN="N">Nodulisporium sp.</Keyword><Keyword MajorTopicYN="N">Phthalides</Keyword></KeywordList><CoiStatement>Declaration of Competing Interest The authors declare that they have no conflict of interest.</CoiStatement></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2020</Year><Month>05</Month><Day>31</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2020</Year><Month>07</Month><Day>20</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2020</Year><Month>07</Month><Day>21</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>8</Month><Day>24</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>8</Month><Day>24</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>8</Month><Day>26</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32828376</ArticleId><ArticleId IdType="pii">S0048-3575(20)30165-6</ArticleId><ArticleId IdType="doi">10.1016/j.pestbp.2020.104670</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Mexique</li></country></list><tree><country name="Mexique"><noRegion><name sortKey="Sanchez Fernandez, Rosa Elvira" sort="Sanchez Fernandez, Rosa Elvira" uniqKey="Sanchez Fernandez R" first="Rosa Elvira" last="Sánchez-Fernández">Rosa Elvira Sánchez-Fernández</name></noRegion><name sortKey="Hernandez Ortega, Sim N" sort="Hernandez Ortega, Sim N" uniqKey="Hernandez Ortega S" first="Sim N" last="Hernández-Ortega">Sim N Hernández-Ortega</name><name sortKey="L Pez Cortes, Jose G" sort="L Pez Cortes, Jose G" uniqKey="L Pez Cortes J" first="José G" last="L Pez-Cortés">José G. L Pez-Cortés</name><name sortKey="Macias Rubalcava, Martha Lydia" sort="Macias Rubalcava, Martha Lydia" uniqKey="Macias Rubalcava M" first="Martha Lydia" last="Macías-Rubalcava">Martha Lydia Macías-Rubalcava</name><name sortKey="Rangel Sanchez, Hiram" sort="Rangel Sanchez, Hiram" uniqKey="Rangel Sanchez H" first="Hiram" last="Rangel-Sánchez">Hiram Rangel-Sánchez</name><name sortKey="Sanchez Fuentes, Rosalia" sort="Sanchez Fuentes, Rosalia" uniqKey="Sanchez Fuentes R" first="Rosalía" last="Sánchez-Fuentes">Rosalía Sánchez-Fuentes</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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