Isolation of 2,5-diketopiperazines from Lysobacter capsici AZ78 with activity against Rhodococcus fascians.
Identifieur interne : 000137 ( Main/Exploration ); précédent : 000136; suivant : 000138Isolation of 2,5-diketopiperazines from Lysobacter capsici AZ78 with activity against Rhodococcus fascians.
Auteurs : Alessio Cimmino [Italie] ; Ana Bejarano [Italie] ; Marco Masi [Italie] ; Gerardo Puopolo [Italie] ; Antonio Evidente [Italie]Source :
- Natural product research [ 1478-6427 ] ; 2020.
Abstract
Inhibitory activity of the biocontrol bacterial strain Lysobacter capsici AZ78 is related to the production of cyclo(l-Pro-l-Tyr), a 2,5-diketopiperazine with in vitro and in vivo toxic activity against Phytophthora infestans and Plasmopara viticola. Further investigation of culture filtrate organic extracts showed its ability to produce other 2,5-diketopiperazines. They were isolated and identified by spectroscopic (1H NMR and ESIMS) and physic (specific optical rotation) methods as cyclo(l-Pro-l-Val), cyclo(d-Pro-d-Phe), cyclo(l-Pro-l-Leu), and cyclo(d-Pro-l-Tyr). When tested against the phytopathogenic Gram-positive bacterium Rhodococcus fascians LMG 3605, cyclo(l-Pro-l-Val) showed a toxic activity similar to chloramphenicol at a comparable concentration. Overall, these data suggest that 2,5-diketopiperazines represent a class of metabolites characterizing the metabolome of L. capsici AZ78. Furthermore, the toxic activity showed by cyclo(l-Pro-l-Val) against R. fascians LMG 3605 broaden the spectrum activity of 2,5-diketopiperazines against phytopathogenic microorganisms enforcing their potential development as biopesticides.[Formula: see text].
DOI: 10.1080/14786419.2020.1756803
PubMed: 32352330
Affiliations:
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Angelo, Napoli, Italy.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Napoli</wicri:regionArea><wicri:noRegion>Napoli</wicri:noRegion></affiliation></author><author><name sortKey="Bejarano, Ana" sort="Bejarano, Ana" uniqKey="Bejarano A" first="Ana" last="Bejarano">Ana Bejarano</name><affiliation wicri:level="1"><nlm:affiliation>Center of Agriculture, Food, Environment, University of Trento, San Michele all'Adige, San Michele all'Adige, Italy.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Center of Agriculture, Food, Environment, University of Trento, San Michele all'Adige, San Michele all'Adige</wicri:regionArea><wicri:noRegion>San Michele all'Adige</wicri:noRegion></affiliation></author><author><name sortKey="Masi, Marco" sort="Masi, Marco" uniqKey="Masi M" first="Marco" last="Masi">Marco Masi</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Napoli</wicri:regionArea><wicri:noRegion>Napoli</wicri:noRegion></affiliation></author><author><name sortKey="Puopolo, Gerardo" sort="Puopolo, Gerardo" uniqKey="Puopolo G" first="Gerardo" last="Puopolo">Gerardo Puopolo</name><affiliation wicri:level="1"><nlm:affiliation>Center of Agriculture, Food, Environment, University of Trento, San Michele all'Adige, San Michele all'Adige, Italy.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Center of Agriculture, Food, Environment, University of Trento, San Michele all'Adige, San Michele all'Adige</wicri:regionArea><wicri:noRegion>San Michele all'Adige</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:affiliation>Department of Sustainable Agro-Ecosystems and Bioresources, Research and Innovation Centre, Fondazione Edmund Mach, San Michele all'Adige, San Michele all'Adige, Italy.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Department of Sustainable Agro-Ecosystems and Bioresources, Research and Innovation Centre, Fondazione Edmund Mach, San Michele all'Adige, San Michele all'Adige</wicri:regionArea><wicri:noRegion>San Michele all'Adige</wicri:noRegion></affiliation></author><author><name sortKey="Evidente, Antonio" sort="Evidente, Antonio" uniqKey="Evidente A" first="Antonio" last="Evidente">Antonio Evidente</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Napoli</wicri:regionArea><wicri:noRegion>Napoli</wicri:noRegion></affiliation></author></analytic><series><title level="j">Natural product research</title><idno type="eISSN">1478-6427</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Inhibitory activity of the biocontrol bacterial strain <i>Lysobacter capsici</i> AZ78 is related to the production of cyclo(l-Pro-l-Tyr), a 2,5-diketopiperazine with <i>in vitro</i> and <i>in vivo</i> toxic activity against <i>Phytophthora infestans</i> and <i>Plasmopara viticola.</i> Further investigation of culture filtrate organic extracts showed its ability to produce other 2,5-diketopiperazines. They were isolated and identified by spectroscopic (<sup>1</sup>H NMR and ESIMS) and physic (specific optical rotation) methods as cyclo(l-Pro-l-Val), cyclo(d-Pro-d-Phe), cyclo(l-Pro-l-Leu), and cyclo(d-Pro-l-Tyr). When tested against the phytopathogenic Gram-positive bacterium <i>Rhodococcus fascians</i> LMG 3605, cyclo(l-Pro-l-Val) showed a toxic activity similar to chloramphenicol at a comparable concentration. Overall, these data suggest that 2,5-diketopiperazines represent a class of metabolites characterizing the metabolome of <i>L. capsici</i> AZ78. Furthermore, the toxic activity showed by cyclo(l-Pro-l-Val) against <i>R. fascians</i> LMG 3605 broaden the spectrum activity of 2,5-diketopiperazines against phytopathogenic microorganisms enforcing their potential development as biopesticides.[Formula: see text].</div></front></TEI><pubmed><MedlineCitation Status="Publisher" Owner="NLM"><PMID Version="1">32352330</PMID><DateRevised><Year>2020</Year><Month>04</Month><Day>30</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1478-6427</ISSN><JournalIssue CitedMedium="Internet"><PubDate><Year>2020</Year><Month>Apr</Month><Day>30</Day></PubDate></JournalIssue><Title>Natural product research</Title><ISOAbbreviation>Nat Prod Res</ISOAbbreviation></Journal><ArticleTitle>Isolation of 2,5-diketopiperazines from <i>Lysobacter capsici</i> AZ78 with activity against <i>Rhodococcus fascians</i>.</ArticleTitle><Pagination><MedlinePgn>1-9</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1080/14786419.2020.1756803</ELocationID><Abstract><AbstractText>Inhibitory activity of the biocontrol bacterial strain <i>Lysobacter capsici</i> AZ78 is related to the production of cyclo(l-Pro-l-Tyr), a 2,5-diketopiperazine with <i>in vitro</i> and <i>in vivo</i> toxic activity against <i>Phytophthora infestans</i> and <i>Plasmopara viticola.</i> Further investigation of culture filtrate organic extracts showed its ability to produce other 2,5-diketopiperazines. They were isolated and identified by spectroscopic (<sup>1</sup>H NMR and ESIMS) and physic (specific optical rotation) methods as cyclo(l-Pro-l-Val), cyclo(d-Pro-d-Phe), cyclo(l-Pro-l-Leu), and cyclo(d-Pro-l-Tyr). When tested against the phytopathogenic Gram-positive bacterium <i>Rhodococcus fascians</i> LMG 3605, cyclo(l-Pro-l-Val) showed a toxic activity similar to chloramphenicol at a comparable concentration. Overall, these data suggest that 2,5-diketopiperazines represent a class of metabolites characterizing the metabolome of <i>L. capsici</i> AZ78. Furthermore, the toxic activity showed by cyclo(l-Pro-l-Val) against <i>R. fascians</i> LMG 3605 broaden the spectrum activity of 2,5-diketopiperazines against phytopathogenic microorganisms enforcing their potential development as biopesticides.[Formula: see text].</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Cimmino</LastName><ForeName>Alessio</ForeName><Initials>A</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-1551-4237</Identifier><AffiliationInfo><Affiliation>Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Bejarano</LastName><ForeName>Ana</ForeName><Initials>A</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-9021-1279</Identifier><AffiliationInfo><Affiliation>Center of Agriculture, Food, Environment, University of Trento, San Michele all'Adige, San Michele all'Adige, Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Masi</LastName><ForeName>Marco</ForeName><Initials>M</Initials><Identifier Source="ORCID">http://orcid.org/0000-0003-0609-8902</Identifier><AffiliationInfo><Affiliation>Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Puopolo</LastName><ForeName>Gerardo</ForeName><Initials>G</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-4864-4396</Identifier><AffiliationInfo><Affiliation>Center of Agriculture, Food, Environment, University of Trento, San Michele all'Adige, San Michele all'Adige, Italy.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Department of Sustainable Agro-Ecosystems and Bioresources, Research and Innovation Centre, Fondazione Edmund Mach, San Michele all'Adige, San Michele all'Adige, Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Evidente</LastName><ForeName>Antonio</ForeName><Initials>A</Initials><Identifier Source="ORCID">http://orcid.org/0000-0001-9110-1656</Identifier><AffiliationInfo><Affiliation>Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>04</Month><Day>30</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Nat Prod Res</MedlineTA><NlmUniqueID>101167924</NlmUniqueID><ISSNLinking>1478-6419</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">25-diketopiperazines</Keyword><Keyword MajorTopicYN="N">Lysobacter capsici</Keyword><Keyword MajorTopicYN="N">Rhodococcus fascians</Keyword><Keyword MajorTopicYN="N">biopesticides</Keyword><Keyword MajorTopicYN="N">cyclic dipeptides</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>5</Month><Day>1</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>5</Month><Day>1</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>5</Month><Day>1</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>aheadofprint</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32352330</ArticleId><ArticleId IdType="doi">10.1080/14786419.2020.1756803</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Italie</li></country></list><tree><country name="Italie"><noRegion><name sortKey="Cimmino, Alessio" sort="Cimmino, Alessio" uniqKey="Cimmino A" first="Alessio" last="Cimmino">Alessio Cimmino</name></noRegion><name sortKey="Bejarano, Ana" sort="Bejarano, Ana" uniqKey="Bejarano A" first="Ana" last="Bejarano">Ana Bejarano</name><name sortKey="Evidente, Antonio" sort="Evidente, Antonio" uniqKey="Evidente A" first="Antonio" last="Evidente">Antonio Evidente</name><name sortKey="Masi, Marco" sort="Masi, Marco" uniqKey="Masi M" first="Marco" last="Masi">Marco Masi</name><name sortKey="Puopolo, Gerardo" sort="Puopolo, Gerardo" uniqKey="Puopolo G" first="Gerardo" last="Puopolo">Gerardo Puopolo</name><name sortKey="Puopolo, Gerardo" sort="Puopolo, Gerardo" uniqKey="Puopolo G" first="Gerardo" last="Puopolo">Gerardo Puopolo</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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