Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step.
Identifieur interne : 000C17 ( Main/Exploration ); précédent : 000C16; suivant : 000C18Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step.
Auteurs : Chiara Lombardi [Italie] ; Emma Artuso ; Eleonora Grandi ; Marco Lolli ; Francesca Spyrakis ; Emanuele Priola ; Cristina PrandiSource :
- Organic & biomolecular chemistry [ 1477-0539 ] ; 2017.
Descripteurs français
- KwdFr :
- Facteur de croissance végétal (composition chimique), Facteur de croissance végétal (synthèse chimique), Germination (effets des médicaments et des substances chimiques), Graines (effets des médicaments et des substances chimiques), Lactones (composition chimique), Lactones (synthèse chimique), Modèles moléculaires (MeSH), Mycorhizes (MeSH), Orobanchaceae (effets des médicaments et des substances chimiques), Structure moléculaire (MeSH).
- MESH :
- composition chimique : Facteur de croissance végétal, Lactones.
- effets des médicaments et des substances chimiques : Germination, Graines, Orobanchaceae.
- synthèse chimique : Facteur de croissance végétal, Lactones.
- Modèles moléculaires, Mycorhizes, Structure moléculaire.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Lactones, Plant Growth Regulators.
- chemical , chemistry : Lactones, Plant Growth Regulators.
- drug effects : Germination, Orobanchaceae, Seeds.
- Models, Molecular, Molecular Structure, Mycorrhizae.
Abstract
In this paper, we synthesized and evaluated the biological activity of structural analogues of natural strigolactones in which the butenolide D-ring has been replaced with a γ-lactam. The key step to obtain the α,β-unsaturated-γ-lactam was an RCM on suitably substituted amides. Strigolactones (SLs) are plant hormones with various developmental functions. As soil signaling chemicals, they are required for establishing beneficial mycorrhizal plant/fungus symbiosis. Beside these auxinic roles, recently SLs have been successfully investigated as antitumoral agents. Peculiar to the SL perception system is the enzymatic activity of the hormone receptor. SARs data have shown that the presence of the butenolide D-ring is crucial to retain the biological activity. The substitution of the butenolide with a lactam might shed light on the mechanism of perception. In the following, a dedicated in silico study suggested the binding modes of the synthesized compounds to the receptor of SLs in plants.
DOI: 10.1039/c7ob01917c
PubMed: 28880031
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step.</title>
<author><name sortKey="Lombardi, Chiara" sort="Lombardi, Chiara" uniqKey="Lombardi C" first="Chiara" last="Lombardi">Chiara Lombardi</name>
<affiliation wicri:level="3"><nlm:affiliation>Department of Chemistry, University of Turin, via P. Giuria 7 10125, Turin, Italy. cristina.prandi@unito.it.</nlm:affiliation>
<country xml:lang="fr">Italie</country>
<wicri:regionArea>Department of Chemistry, University of Turin, via P. Giuria 7 10125, Turin</wicri:regionArea>
<placeName><settlement type="city">Turin</settlement>
<region type="région" nuts="2">Piémont</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Artuso, Emma" sort="Artuso, Emma" uniqKey="Artuso E" first="Emma" last="Artuso">Emma Artuso</name>
</author>
<author><name sortKey="Grandi, Eleonora" sort="Grandi, Eleonora" uniqKey="Grandi E" first="Eleonora" last="Grandi">Eleonora Grandi</name>
</author>
<author><name sortKey="Lolli, Marco" sort="Lolli, Marco" uniqKey="Lolli M" first="Marco" last="Lolli">Marco Lolli</name>
</author>
<author><name sortKey="Spyrakis, Francesca" sort="Spyrakis, Francesca" uniqKey="Spyrakis F" first="Francesca" last="Spyrakis">Francesca Spyrakis</name>
</author>
<author><name sortKey="Priola, Emanuele" sort="Priola, Emanuele" uniqKey="Priola E" first="Emanuele" last="Priola">Emanuele Priola</name>
</author>
<author><name sortKey="Prandi, Cristina" sort="Prandi, Cristina" uniqKey="Prandi C" first="Cristina" last="Prandi">Cristina Prandi</name>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PubMed</idno>
<date when="2017">2017</date>
<idno type="RBID">pubmed:28880031</idno>
<idno type="pmid">28880031</idno>
<idno type="doi">10.1039/c7ob01917c</idno>
<idno type="wicri:Area/Main/Corpus">000B48</idno>
<idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Corpus" wicri:corpus="PubMed">000B48</idno>
<idno type="wicri:Area/Main/Curation">000B48</idno>
<idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Curation">000B48</idno>
<idno type="wicri:Area/Main/Exploration">000B48</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en">Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step.</title>
<author><name sortKey="Lombardi, Chiara" sort="Lombardi, Chiara" uniqKey="Lombardi C" first="Chiara" last="Lombardi">Chiara Lombardi</name>
<affiliation wicri:level="3"><nlm:affiliation>Department of Chemistry, University of Turin, via P. Giuria 7 10125, Turin, Italy. cristina.prandi@unito.it.</nlm:affiliation>
<country xml:lang="fr">Italie</country>
<wicri:regionArea>Department of Chemistry, University of Turin, via P. Giuria 7 10125, Turin</wicri:regionArea>
<placeName><settlement type="city">Turin</settlement>
<region type="région" nuts="2">Piémont</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Artuso, Emma" sort="Artuso, Emma" uniqKey="Artuso E" first="Emma" last="Artuso">Emma Artuso</name>
</author>
<author><name sortKey="Grandi, Eleonora" sort="Grandi, Eleonora" uniqKey="Grandi E" first="Eleonora" last="Grandi">Eleonora Grandi</name>
</author>
<author><name sortKey="Lolli, Marco" sort="Lolli, Marco" uniqKey="Lolli M" first="Marco" last="Lolli">Marco Lolli</name>
</author>
<author><name sortKey="Spyrakis, Francesca" sort="Spyrakis, Francesca" uniqKey="Spyrakis F" first="Francesca" last="Spyrakis">Francesca Spyrakis</name>
</author>
<author><name sortKey="Priola, Emanuele" sort="Priola, Emanuele" uniqKey="Priola E" first="Emanuele" last="Priola">Emanuele Priola</name>
</author>
<author><name sortKey="Prandi, Cristina" sort="Prandi, Cristina" uniqKey="Prandi C" first="Cristina" last="Prandi">Cristina Prandi</name>
</author>
</analytic>
<series><title level="j">Organic & biomolecular chemistry</title>
<idno type="eISSN">1477-0539</idno>
<imprint><date when="2017" type="published">2017</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Germination (drug effects)</term>
<term>Lactones (chemical synthesis)</term>
<term>Lactones (chemistry)</term>
<term>Models, Molecular (MeSH)</term>
<term>Molecular Structure (MeSH)</term>
<term>Mycorrhizae (MeSH)</term>
<term>Orobanchaceae (drug effects)</term>
<term>Plant Growth Regulators (chemical synthesis)</term>
<term>Plant Growth Regulators (chemistry)</term>
<term>Seeds (drug effects)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Facteur de croissance végétal (composition chimique)</term>
<term>Facteur de croissance végétal (synthèse chimique)</term>
<term>Germination (effets des médicaments et des substances chimiques)</term>
<term>Graines (effets des médicaments et des substances chimiques)</term>
<term>Lactones (composition chimique)</term>
<term>Lactones (synthèse chimique)</term>
<term>Modèles moléculaires (MeSH)</term>
<term>Mycorhizes (MeSH)</term>
<term>Orobanchaceae (effets des médicaments et des substances chimiques)</term>
<term>Structure moléculaire (MeSH)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Lactones</term>
<term>Plant Growth Regulators</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Lactones</term>
<term>Plant Growth Regulators</term>
</keywords>
<keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Facteur de croissance végétal</term>
<term>Lactones</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Germination</term>
<term>Orobanchaceae</term>
<term>Seeds</term>
</keywords>
<keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Germination</term>
<term>Graines</term>
<term>Orobanchaceae</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Facteur de croissance végétal</term>
<term>Lactones</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Models, Molecular</term>
<term>Molecular Structure</term>
<term>Mycorrhizae</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Modèles moléculaires</term>
<term>Mycorhizes</term>
<term>Structure moléculaire</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">In this paper, we synthesized and evaluated the biological activity of structural analogues of natural strigolactones in which the butenolide D-ring has been replaced with a γ-lactam. The key step to obtain the α,β-unsaturated-γ-lactam was an RCM on suitably substituted amides. Strigolactones (SLs) are plant hormones with various developmental functions. As soil signaling chemicals, they are required for establishing beneficial mycorrhizal plant/fungus symbiosis. Beside these auxinic roles, recently SLs have been successfully investigated as antitumoral agents. Peculiar to the SL perception system is the enzymatic activity of the hormone receptor. SARs data have shown that the presence of the butenolide D-ring is crucial to retain the biological activity. The substitution of the butenolide with a lactam might shed light on the mechanism of perception. In the following, a dedicated in silico study suggested the binding modes of the synthesized compounds to the receptor of SLs in plants.</div>
</front>
</TEI>
<pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">28880031</PMID>
<DateCompleted><Year>2018</Year>
<Month>04</Month>
<Day>30</Day>
</DateCompleted>
<DateRevised><Year>2019</Year>
<Month>03</Month>
<Day>29</Day>
</DateRevised>
<Article PubModel="Print"><Journal><ISSN IssnType="Electronic">1477-0539</ISSN>
<JournalIssue CitedMedium="Internet"><Volume>15</Volume>
<Issue>38</Issue>
<PubDate><Year>2017</Year>
<Month>10</Month>
<Day>04</Day>
</PubDate>
</JournalIssue>
<Title>Organic & biomolecular chemistry</Title>
<ISOAbbreviation>Org Biomol Chem</ISOAbbreviation>
</Journal>
<ArticleTitle>Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step.</ArticleTitle>
<Pagination><MedlinePgn>8218-8231</MedlinePgn>
</Pagination>
<ELocationID EIdType="doi" ValidYN="Y">10.1039/c7ob01917c</ELocationID>
<Abstract><AbstractText>In this paper, we synthesized and evaluated the biological activity of structural analogues of natural strigolactones in which the butenolide D-ring has been replaced with a γ-lactam. The key step to obtain the α,β-unsaturated-γ-lactam was an RCM on suitably substituted amides. Strigolactones (SLs) are plant hormones with various developmental functions. As soil signaling chemicals, they are required for establishing beneficial mycorrhizal plant/fungus symbiosis. Beside these auxinic roles, recently SLs have been successfully investigated as antitumoral agents. Peculiar to the SL perception system is the enzymatic activity of the hormone receptor. SARs data have shown that the presence of the butenolide D-ring is crucial to retain the biological activity. The substitution of the butenolide with a lactam might shed light on the mechanism of perception. In the following, a dedicated in silico study suggested the binding modes of the synthesized compounds to the receptor of SLs in plants.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Lombardi</LastName>
<ForeName>Chiara</ForeName>
<Initials>C</Initials>
<AffiliationInfo><Affiliation>Department of Chemistry, University of Turin, via P. Giuria 7 10125, Turin, Italy. cristina.prandi@unito.it.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Artuso</LastName>
<ForeName>Emma</ForeName>
<Initials>E</Initials>
</Author>
<Author ValidYN="Y"><LastName>Grandi</LastName>
<ForeName>Eleonora</ForeName>
<Initials>E</Initials>
</Author>
<Author ValidYN="Y"><LastName>Lolli</LastName>
<ForeName>Marco</ForeName>
<Initials>M</Initials>
</Author>
<Author ValidYN="Y"><LastName>Spyrakis</LastName>
<ForeName>Francesca</ForeName>
</Author>
<Author ValidYN="Y"><LastName>Priola</LastName>
<ForeName>Emanuele</ForeName>
<Initials>E</Initials>
</Author>
<Author ValidYN="Y"><LastName>Prandi</LastName>
<ForeName>Cristina</ForeName>
<Initials>C</Initials>
</Author>
</AuthorList>
<Language>eng</Language>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
</PublicationTypeList>
</Article>
<MedlineJournalInfo><Country>England</Country>
<MedlineTA>Org Biomol Chem</MedlineTA>
<NlmUniqueID>101154995</NlmUniqueID>
<ISSNLinking>1477-0520</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D007783">Lactones</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D010937">Plant Growth Regulators</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<CommentsCorrectionsList><CommentsCorrections RefType="ErratumIn"><RefSource>Org Biomol Chem. 2017 Oct 4;15(38):8232</RefSource>
<PMID Version="1">28932861</PMID>
<Note>Spirakys F [corrected to Spyrakis F]</Note>
</CommentsCorrections>
</CommentsCorrectionsList>
<MeshHeadingList><MeshHeading><DescriptorName UI="D018525" MajorTopicYN="N">Germination</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D007783" MajorTopicYN="N">Lactones</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D038821" MajorTopicYN="N">Mycorrhizae</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D031670" MajorTopicYN="N">Orobanchaceae</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D010937" MajorTopicYN="N">Plant Growth Regulators</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D012639" MajorTopicYN="N">Seeds</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
</MeshHeadingList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2017</Year>
<Month>9</Month>
<Day>8</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2018</Year>
<Month>5</Month>
<Day>1</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2017</Year>
<Month>9</Month>
<Day>8</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">28880031</ArticleId>
<ArticleId IdType="doi">10.1039/c7ob01917c</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
<affiliations><list><country><li>Italie</li>
</country>
<region><li>Piémont</li>
</region>
<settlement><li>Turin</li>
</settlement>
</list>
<tree><noCountry><name sortKey="Artuso, Emma" sort="Artuso, Emma" uniqKey="Artuso E" first="Emma" last="Artuso">Emma Artuso</name>
<name sortKey="Grandi, Eleonora" sort="Grandi, Eleonora" uniqKey="Grandi E" first="Eleonora" last="Grandi">Eleonora Grandi</name>
<name sortKey="Lolli, Marco" sort="Lolli, Marco" uniqKey="Lolli M" first="Marco" last="Lolli">Marco Lolli</name>
<name sortKey="Prandi, Cristina" sort="Prandi, Cristina" uniqKey="Prandi C" first="Cristina" last="Prandi">Cristina Prandi</name>
<name sortKey="Priola, Emanuele" sort="Priola, Emanuele" uniqKey="Priola E" first="Emanuele" last="Priola">Emanuele Priola</name>
<name sortKey="Spyrakis, Francesca" sort="Spyrakis, Francesca" uniqKey="Spyrakis F" first="Francesca" last="Spyrakis">Francesca Spyrakis</name>
</noCountry>
<country name="Italie"><region name="Piémont"><name sortKey="Lombardi, Chiara" sort="Lombardi, Chiara" uniqKey="Lombardi C" first="Chiara" last="Lombardi">Chiara Lombardi</name>
</region>
</country>
</tree>
</affiliations>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Bois/explor/MycorrhizaeV1/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000C17 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 000C17 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Bois |area= MycorrhizaeV1 |flux= Main |étape= Exploration |type= RBID |clé= pubmed:28880031 |texte= Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step. }}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Main/Exploration/RBID.i -Sk "pubmed:28880031" \ | HfdSelect -Kh $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd \ | NlmPubMed2Wicri -a MycorrhizaeV1
This area was generated with Dilib version V0.6.37. |