Phytotoxic Metabolites Produced by Diaporthella cryptica, the Causal Agent of Hazelnut Branch Canker.
Identifieur interne : 000697 ( Main/Exploration ); précédent : 000696; suivant : 000698Phytotoxic Metabolites Produced by Diaporthella cryptica, the Causal Agent of Hazelnut Branch Canker.
Auteurs : Alessio Cimmino [Italie] ; Paola Nocera [Italie] ; Benedetto Teodoro Linaldeddu [Italie] ; Marco Masi [Italie] ; Marcin Gorecki [Italie] ; Gennaro Pescitelli [Italie] ; Lucio Montecchio [Italie] ; Lucia Maddau [Italie] ; Antonio Evidente [Italie]Source :
- Journal of agricultural and food chemistry [ 1520-5118 ] ; 2018.
Descripteurs français
- KwdFr :
- Ascomycota (composition chimique), Ascomycota (métabolisme), Corylus (microbiologie), Dichroïsme circulaire (MeSH), Lycopersicon esculentum (microbiologie), Maladies des plantes (microbiologie), Mycotoxines (composition chimique), Mycotoxines (métabolisme), Quercus (microbiologie), Structure moléculaire (MeSH), Stéréoisomérie (MeSH).
- MESH :
- composition chimique : Ascomycota, Mycotoxines.
- microbiologie : Corylus, Lycopersicon esculentum, Maladies des plantes, Quercus.
- métabolisme : Ascomycota, Mycotoxines.
- Dichroïsme circulaire, Structure moléculaire, Stéréoisomérie.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Mycotoxins.
- chemistry : Ascomycota.
- metabolism : Ascomycota, Mycotoxins.
- microbiology : Corylus, Lycopersicon esculentum, Plant Diseases, Quercus.
- Circular Dichroism, Molecular Structure, Stereoisomerism.
Abstract
From the culture filtrates of Diaporthella cryptica, an emerging hazelnut pathogen, 2-hydroxy-3-phenylpropanoate methyl ester and its 3-(4-hydroxyphenyl) and 3-(1 H-indol-3-yl) analogues, named crypticins A-C, were isolated together with the well-known tyrosol. Crypticins A-C were identified by spectroscopic (essentially nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry) methods. The R absolute configuration (AC) of crypticin A was determined by comparing its optical rotation and electronic circular dichroism (ECD) spectrum with those of papuline, the methyl ester of (-)( S)-phenyllactic acid isolated as the main phytotoxin of Pseudomonas syringae pv. papulans, responsible for apple blister spot. The ACs of crypticins B and C were determined by time-dependent density functional theory calculations of their ECD spectra. Papuline and the new metabolites herein isolated, except tyrosol, were tested at 1 mg/mL on cork oak, grapevine, hazelnut, and holm oak leaves using the leaf puncture assay. They were also tested on tomato cuttings at 0.5 and 0.05 mg/mL. In the leaf puncture assay, none of the compounds was found to be active. Crypticin C and papuline were active in the tomato cutting assay. Additionally, crypticin C displayed moderate inhibitory effect against Phytophthora cambivora.
DOI: 10.1021/acs.jafc.8b00256
PubMed: 29537269
Affiliations:
Links toward previous steps (curation, corpus...)
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Angelo, Via Cintia 4 , Napoli 80126 , Italy.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Dipartimento Scienze Chimiche , Università di Napoli Federico II , Complesso Universitario Monte S. Angelo, Via Cintia 4 , Napoli 80126 </wicri:regionArea><wicri:noRegion>Napoli 80126 </wicri:noRegion></affiliation></author><author><name sortKey="Nocera, Paola" sort="Nocera, Paola" uniqKey="Nocera P" first="Paola" last="Nocera">Paola Nocera</name><affiliation wicri:level="1"><nlm:affiliation>Dipartimento Scienze Chimiche , Università di Napoli Federico II , Complesso Universitario Monte S. Angelo, Via Cintia 4 , Napoli 80126 , Italy.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Dipartimento Scienze Chimiche , Università di Napoli Federico II , Complesso Universitario Monte S. 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Angelo, Via Cintia 4 , Napoli 80126 , Italy.</nlm:affiliation><country xml:lang="fr">Italie</country><wicri:regionArea>Dipartimento Scienze Chimiche , Università di Napoli Federico II , Complesso Universitario Monte S. Angelo, Via Cintia 4 , Napoli 80126 </wicri:regionArea><wicri:noRegion>Napoli 80126 </wicri:noRegion></affiliation></author></analytic><series><title level="j">Journal of agricultural and food chemistry</title><idno type="eISSN">1520-5118</idno><imprint><date when="2018" type="published">2018</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Ascomycota (chemistry)</term><term>Ascomycota (metabolism)</term><term>Circular Dichroism (MeSH)</term><term>Corylus (microbiology)</term><term>Lycopersicon esculentum (microbiology)</term><term>Molecular Structure (MeSH)</term><term>Mycotoxins (chemistry)</term><term>Mycotoxins (metabolism)</term><term>Plant Diseases (microbiology)</term><term>Quercus (microbiology)</term><term>Stereoisomerism (MeSH)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Ascomycota (composition chimique)</term><term>Ascomycota (métabolisme)</term><term>Corylus (microbiologie)</term><term>Dichroïsme circulaire (MeSH)</term><term>Lycopersicon esculentum (microbiologie)</term><term>Maladies des plantes (microbiologie)</term><term>Mycotoxines (composition chimique)</term><term>Mycotoxines (métabolisme)</term><term>Quercus (microbiologie)</term><term>Structure moléculaire (MeSH)</term><term>Stéréoisomérie (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Mycotoxins</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><term>Mycotoxines</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Ascomycota</term><term>Mycotoxins</term></keywords><keywords scheme="MESH" qualifier="microbiologie" xml:lang="fr"><term>Corylus</term><term>Lycopersicon esculentum</term><term>Maladies des plantes</term><term>Quercus</term></keywords><keywords scheme="MESH" qualifier="microbiology" xml:lang="en"><term>Corylus</term><term>Lycopersicon esculentum</term><term>Plant Diseases</term><term>Quercus</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Ascomycota</term><term>Mycotoxines</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Circular Dichroism</term><term>Molecular Structure</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Dichroïsme circulaire</term><term>Structure moléculaire</term><term>Stéréoisomérie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">From the culture filtrates of Diaporthella cryptica, an emerging hazelnut pathogen, 2-hydroxy-3-phenylpropanoate methyl ester and its 3-(4-hydroxyphenyl) and 3-(1 H-indol-3-yl) analogues, named crypticins A-C, were isolated together with the well-known tyrosol. Crypticins A-C were identified by spectroscopic (essentially nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry) methods. The R absolute configuration (AC) of crypticin A was determined by comparing its optical rotation and electronic circular dichroism (ECD) spectrum with those of papuline, the methyl ester of (-)( S)-phenyllactic acid isolated as the main phytotoxin of Pseudomonas syringae pv. papulans, responsible for apple blister spot. The ACs of crypticins B and C were determined by time-dependent density functional theory calculations of their ECD spectra. Papuline and the new metabolites herein isolated, except tyrosol, were tested at 1 mg/mL on cork oak, grapevine, hazelnut, and holm oak leaves using the leaf puncture assay. They were also tested on tomato cuttings at 0.5 and 0.05 mg/mL. In the leaf puncture assay, none of the compounds was found to be active. Crypticin C and papuline were active in the tomato cutting assay. Additionally, crypticin C displayed moderate inhibitory effect against Phytophthora cambivora.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">29537269</PMID><DateCompleted><Year>2018</Year><Month>04</Month><Day>27</Day></DateCompleted><DateRevised><Year>2018</Year><Month>04</Month><Day>27</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5118</ISSN><JournalIssue CitedMedium="Internet"><Volume>66</Volume><Issue>13</Issue><PubDate><Year>2018</Year><Month>Apr</Month><Day>04</Day></PubDate></JournalIssue><Title>Journal of agricultural and food chemistry</Title><ISOAbbreviation>J Agric Food Chem</ISOAbbreviation></Journal><ArticleTitle>Phytotoxic Metabolites Produced by Diaporthella cryptica, the Causal Agent of Hazelnut Branch Canker.</ArticleTitle><Pagination><MedlinePgn>3435-3442</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.jafc.8b00256</ELocationID><Abstract><AbstractText>From the culture filtrates of Diaporthella cryptica, an emerging hazelnut pathogen, 2-hydroxy-3-phenylpropanoate methyl ester and its 3-(4-hydroxyphenyl) and 3-(1 H-indol-3-yl) analogues, named crypticins A-C, were isolated together with the well-known tyrosol. Crypticins A-C were identified by spectroscopic (essentially nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry) methods. The R absolute configuration (AC) of crypticin A was determined by comparing its optical rotation and electronic circular dichroism (ECD) spectrum with those of papuline, the methyl ester of (-)( S)-phenyllactic acid isolated as the main phytotoxin of Pseudomonas syringae pv. papulans, responsible for apple blister spot. The ACs of crypticins B and C were determined by time-dependent density functional theory calculations of their ECD spectra. Papuline and the new metabolites herein isolated, except tyrosol, were tested at 1 mg/mL on cork oak, grapevine, hazelnut, and holm oak leaves using the leaf puncture assay. They were also tested on tomato cuttings at 0.5 and 0.05 mg/mL. In the leaf puncture assay, none of the compounds was found to be active. Crypticin C and papuline were active in the tomato cutting assay. Additionally, crypticin C displayed moderate inhibitory effect against Phytophthora cambivora.</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>Dipartimento Scienze Chimiche , Università di Napoli Federico II , Complesso Universitario Monte S. Angelo, Via Cintia 4 , Napoli 80126 , Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Nocera</LastName><ForeName>Paola</ForeName><Initials>P</Initials><AffiliationInfo><Affiliation>Dipartimento Scienze Chimiche , Università di Napoli Federico II , Complesso Universitario Monte S. Angelo, Via Cintia 4 , Napoli 80126 , Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Linaldeddu</LastName><ForeName>Benedetto Teodoro</ForeName><Initials>BT</Initials><AffiliationInfo><Affiliation>Dipartimento Territorio e Sistemi Agro-Forestali , Università di Padova , Viale dell'Università 16 , Legnaro , Padova 35020 , Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Masi</LastName><ForeName>Marco</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Dipartimento Scienze Chimiche , Università di Napoli Federico II , Complesso Universitario Monte S. Angelo, Via Cintia 4 , Napoli 80126 , Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gorecki</LastName><ForeName>Marcin</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Dipartimento di Chimica e Chimica Industriale , Università di Pisa , Via Moruzzi, 13 , Pisa 56124 , Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Pescitelli</LastName><ForeName>Gennaro</ForeName><Initials>G</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-0869-5076</Identifier><AffiliationInfo><Affiliation>Dipartimento di Chimica e Chimica Industriale , Università di Pisa , Via Moruzzi, 13 , Pisa 56124 , Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Montecchio</LastName><ForeName>Lucio</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>Dipartimento Territorio e Sistemi Agro-Forestali , Università di Padova , Viale dell'Università 16 , Legnaro , Padova 35020 , Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Maddau</LastName><ForeName>Lucia</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>Dipartimento di Agraria, Sezione di Patologia Vegetale ed Entomologia , Università degli Studi di Sassari , Viale Italia 39 , Sassari 07100 , 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>Dipartimento Scienze Chimiche , Università di Napoli Federico II , Complesso Universitario Monte S. Angelo, Via Cintia 4 , Napoli 80126 , Italy.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2018</Year><Month>03</Month><Day>21</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Agric Food Chem</MedlineTA><NlmUniqueID>0374755</NlmUniqueID><ISSNLinking>0021-8561</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009183">Mycotoxins</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D001203" MajorTopicYN="N">Ascomycota</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002942" MajorTopicYN="N">Circular Dichroism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D031211" MajorTopicYN="N">Corylus</DescriptorName><QualifierName UI="Q000382" MajorTopicYN="Y">microbiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D018551" MajorTopicYN="N">Lycopersicon esculentum</DescriptorName><QualifierName UI="Q000382" MajorTopicYN="N">microbiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009183" MajorTopicYN="N">Mycotoxins</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010935" MajorTopicYN="N">Plant Diseases</DescriptorName><QualifierName UI="Q000382" MajorTopicYN="Y">microbiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D029963" MajorTopicYN="N">Quercus</DescriptorName><QualifierName UI="Q000382" MajorTopicYN="N">microbiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">TDDFT ECD calculations</Keyword><Keyword MajorTopicYN="N">emerging pathogen</Keyword><Keyword MajorTopicYN="N">hazelnut branch canker</Keyword><Keyword MajorTopicYN="N">phenyllactic acid derivatives</Keyword><Keyword MajorTopicYN="N">phytotoxins</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2018</Year><Month>3</Month><Day>15</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2018</Year><Month>4</Month><Day>28</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2018</Year><Month>3</Month><Day>15</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">29537269</ArticleId><ArticleId IdType="doi">10.1021/acs.jafc.8b00256</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="Evidente, Antonio" sort="Evidente, Antonio" uniqKey="Evidente A" first="Antonio" last="Evidente">Antonio Evidente</name><name sortKey="Gorecki, Marcin" sort="Gorecki, Marcin" uniqKey="Gorecki M" first="Marcin" last="Gorecki">Marcin Gorecki</name><name sortKey="Linaldeddu, Benedetto Teodoro" sort="Linaldeddu, Benedetto Teodoro" uniqKey="Linaldeddu B" first="Benedetto Teodoro" last="Linaldeddu">Benedetto Teodoro Linaldeddu</name><name sortKey="Maddau, Lucia" sort="Maddau, Lucia" uniqKey="Maddau L" first="Lucia" last="Maddau">Lucia Maddau</name><name sortKey="Masi, Marco" sort="Masi, Marco" uniqKey="Masi M" first="Marco" last="Masi">Marco Masi</name><name sortKey="Montecchio, Lucio" sort="Montecchio, Lucio" uniqKey="Montecchio L" first="Lucio" last="Montecchio">Lucio Montecchio</name><name sortKey="Nocera, Paola" sort="Nocera, Paola" uniqKey="Nocera P" first="Paola" last="Nocera">Paola Nocera</name><name sortKey="Pescitelli, Gennaro" sort="Pescitelli, Gennaro" uniqKey="Pescitelli G" first="Gennaro" last="Pescitelli">Gennaro Pescitelli</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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