MycorrhizaeV1, Main, Corpus, bibRecord, 000B48

Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step.

Identifieur interne : 000B48 ( Main/Corpus ); précédent : 000B47; suivant : 000B49

Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step.

Auteurs : Chiara Lombardi ; Emma Artuso ; Eleonora Grandi ; Marco Lolli ; Francesca Spyrakis ; Emanuele Priola ; Cristina Prandi

Source :

Organic & biomolecular chemistry [ 1477-0539 ] ; 2017.

RBID : pubmed:28880031

English descriptors

KwdEn :
- Germination (drug effects), Lactones (chemical synthesis), Lactones (chemistry), Models, Molecular (MeSH), Molecular Structure (MeSH), Mycorrhizae (MeSH), Orobanchaceae (drug effects), Plant Growth Regulators (chemical synthesis), Plant Growth Regulators (chemistry), Seeds (drug effects).
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

Links to Exploration step

pubmed:28880031

Le document en format XML

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<author><name sortKey="Lombardi, Chiara" sort="Lombardi, Chiara" uniqKey="Lombardi C" first="Chiara" last="Lombardi">Chiara Lombardi</name>
<affiliation><nlm:affiliation>Department of Chemistry, University of Turin, via P. Giuria 7 10125, Turin, Italy. cristina.prandi@unito.it.</nlm:affiliation>
</affiliation>
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<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>
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<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>
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<author><name sortKey="Prandi, Cristina" sort="Prandi, Cristina" uniqKey="Prandi C" first="Cristina" last="Prandi">Cristina Prandi</name>
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<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><nlm:affiliation>Department of Chemistry, University of Turin, via P. Giuria 7 10125, Turin, Italy. cristina.prandi@unito.it.</nlm:affiliation>
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<author><name sortKey="Artuso, Emma" sort="Artuso, Emma" uniqKey="Artuso E" first="Emma" last="Artuso">Emma Artuso</name>
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<author><name sortKey="Grandi, Eleonora" sort="Grandi, Eleonora" uniqKey="Grandi E" first="Eleonora" last="Grandi">Eleonora Grandi</name>
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<author><name sortKey="Lolli, Marco" sort="Lolli, Marco" uniqKey="Lolli M" first="Marco" last="Lolli">Marco Lolli</name>
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<author><name sortKey="Spyrakis, Francesca" sort="Spyrakis, Francesca" uniqKey="Spyrakis F" first="Francesca" last="Spyrakis">Francesca Spyrakis</name>
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<author><name sortKey="Priola, Emanuele" sort="Priola, Emanuele" uniqKey="Priola E" first="Emanuele" last="Priola">Emanuele Priola</name>
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<author><name sortKey="Prandi, Cristina" sort="Prandi, Cristina" uniqKey="Prandi C" first="Cristina" last="Prandi">Cristina Prandi</name>
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<series><title level="j">Organic & biomolecular chemistry</title>
<idno type="eISSN">1477-0539</idno>
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<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="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="drug effects" xml:lang="en"><term>Germination</term>
<term>Orobanchaceae</term>
<term>Seeds</term>
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<keywords scheme="MESH" xml:lang="en"><term>Models, Molecular</term>
<term>Molecular Structure</term>
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<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>
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<DateCompleted><Year>2018</Year>
<Month>04</Month>
<Day>30</Day>
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<DateRevised><Year>2019</Year>
<Month>03</Month>
<Day>29</Day>
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<JournalIssue CitedMedium="Internet"><Volume>15</Volume>
<Issue>38</Issue>
<PubDate><Year>2017</Year>
<Month>10</Month>
<Day>04</Day>
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<Title>Organic & biomolecular chemistry</Title>
<ISOAbbreviation>Org Biomol Chem</ISOAbbreviation>
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<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>
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<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>
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<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Lombardi</LastName>
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<Author ValidYN="Y"><LastName>Grandi</LastName>
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<CommentsCorrectionsList><CommentsCorrections RefType="ErratumIn"><RefSource>Org Biomol Chem. 2017 Oct 4;15(38):8232</RefSource>
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<Note>Spirakys F [corrected to Spyrakis F]</Note>
</CommentsCorrections>
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<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>
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<PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2017</Year>
<Month>9</Month>
<Day>8</Day>
<Hour>6</Hour>
<Minute>0</Minute>
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Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step.

Recent advances in the synthesis of analogues of phytohormones strigolactones with ring-closing metathesis as a key step.

Source :

English descriptors

Abstract

Links to Exploration step

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

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