Cytotoxic Guanidine Alkaloids from a French Polynesian Monanchora n. sp. Sponge.
Identifieur interne : 001A33 ( PubMed/Corpus ); précédent : 001A32; suivant : 001A34Cytotoxic Guanidine Alkaloids from a French Polynesian Monanchora n. sp. Sponge.
Auteurs : Amr El-Demerdash ; Céline Moriou ; Marie-Thérèse Martin ; Alice De Souza Rodrigues-Stien ; Sylvain Petek ; Marina Demoy-Schneider ; Kathryn Hall ; John N A. Hooper ; Cécile Debitus ; Ali Al-MourabitSource :
- Journal of natural products [ 1520-6025 ] ; 2016.
English descriptors
- KwdEn :
- Alkaloids (chemistry), Alkaloids (isolation & purification), Alkaloids (pharmacology), Animals, Antineoplastic Agents (chemistry), Antineoplastic Agents (isolation & purification), Antineoplastic Agents (pharmacology), Axinella (chemistry), Drug Screening Assays, Antitumor, Guanidines (chemistry), Guanidines (isolation & purification), Guanidines (pharmacology), HCT116 Cells, HL-60 Cells, Humans, Inhibitory Concentration 50, KB Cells, Marine Biology, Nuclear Magnetic Resonance, Biomolecular, Polynesia.
- MESH :
- chemical , chemistry : Alkaloids, Antineoplastic Agents, Guanidines.
- chemical , isolation & purification : Alkaloids, Antineoplastic Agents, Guanidines.
- chemical , pharmacology : Alkaloids, Antineoplastic Agents, Guanidines.
- chemistry : Axinella.
- Animals, Drug Screening Assays, Antitumor, HCT116 Cells, HL-60 Cells, Humans, Inhibitory Concentration 50, KB Cells, Marine Biology, Nuclear Magnetic Resonance, Biomolecular, Polynesia.
Abstract
Four bicyclic and three pentacyclic guanidine alkaloids (1-7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9-11 of known natural product crambescins, and the known crambescidins 12-15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of (1)H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC50 values ranging from 4 nM to 10 μM.
DOI: 10.1021/acs.jnatprod.6b00168
PubMed: 27419263
Links to Exploration step
pubmed:27419263Le document en format XML
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Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.</nlm:affiliation></affiliation></author><author><name sortKey="Moriou, Celine" sort="Moriou, Celine" uniqKey="Moriou C" first="Céline" last="Moriou">Céline Moriou</name><affiliation><nlm:affiliation>Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.</nlm:affiliation></affiliation></author><author><name sortKey="Martin, Marie Therese" sort="Martin, Marie Therese" uniqKey="Martin M" first="Marie-Thérèse" last="Martin">Marie-Thérèse Martin</name><affiliation><nlm:affiliation>Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.</nlm:affiliation></affiliation></author><author><name sortKey="Rodrigues Stien, Alice De Souza" sort="Rodrigues Stien, Alice De Souza" uniqKey="Rodrigues Stien A" first="Alice De Souza" last="Rodrigues-Stien">Alice De Souza Rodrigues-Stien</name><affiliation><nlm:affiliation>Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.</nlm:affiliation></affiliation></author><author><name sortKey="Petek, Sylvain" sort="Petek, Sylvain" uniqKey="Petek S" first="Sylvain" last="Petek">Sylvain Petek</name><affiliation><nlm:affiliation>Institut de Recherche pour le Développement (IRD) , UMR-241 EIO, BP529, 98713, Papeete, Tahiti, French Polynesia.</nlm:affiliation></affiliation></author><author><name sortKey="Demoy Schneider, Marina" sort="Demoy Schneider, Marina" uniqKey="Demoy Schneider M" first="Marina" last="Demoy-Schneider">Marina Demoy-Schneider</name><affiliation><nlm:affiliation>Université de la Polynésie Française , UMR-241 EIO, BP 6570, 98702 Faa'a Aéroport, Tahiti, French Polynesia.</nlm:affiliation></affiliation></author><author><name sortKey="Hall, Kathryn" sort="Hall, Kathryn" uniqKey="Hall K" first="Kathryn" last="Hall">Kathryn Hall</name><affiliation><nlm:affiliation>Queensland Museum , PO Box 3300, South Brisbane BC, Queensland 4101, Australia.</nlm:affiliation></affiliation></author><author><name sortKey="Hooper, John N A" sort="Hooper, John N A" uniqKey="Hooper J" first="John N A" last="Hooper">John N A. Hooper</name><affiliation><nlm:affiliation>Queensland Museum , PO Box 3300, South Brisbane BC, Queensland 4101, Australia.</nlm:affiliation></affiliation></author><author><name sortKey="Debitus, Cecile" sort="Debitus, Cecile" uniqKey="Debitus C" first="Cécile" last="Debitus">Cécile Debitus</name><affiliation><nlm:affiliation>Institut de Recherche pour le Développement (IRD) , UMR-241 EIO, BP529, 98713, Papeete, Tahiti, French Polynesia.</nlm:affiliation></affiliation></author><author><name sortKey="Al Mourabit, Ali" sort="Al Mourabit, Ali" uniqKey="Al Mourabit A" first="Ali" last="Al-Mourabit">Ali Al-Mourabit</name><affiliation><nlm:affiliation>Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.</nlm:affiliation></affiliation></author></analytic><series><title level="j">Journal of natural products</title><idno type="eISSN">1520-6025</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alkaloids (chemistry)</term><term>Alkaloids (isolation & purification)</term><term>Alkaloids (pharmacology)</term><term>Animals</term><term>Antineoplastic Agents (chemistry)</term><term>Antineoplastic Agents (isolation & purification)</term><term>Antineoplastic Agents (pharmacology)</term><term>Axinella (chemistry)</term><term>Drug Screening Assays, Antitumor</term><term>Guanidines (chemistry)</term><term>Guanidines (isolation & purification)</term><term>Guanidines (pharmacology)</term><term>HCT116 Cells</term><term>HL-60 Cells</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>KB Cells</term><term>Marine Biology</term><term>Nuclear Magnetic Resonance, Biomolecular</term><term>Polynesia</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Alkaloids</term><term>Antineoplastic Agents</term><term>Guanidines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Alkaloids</term><term>Antineoplastic Agents</term><term>Guanidines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Alkaloids</term><term>Antineoplastic Agents</term><term>Guanidines</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Axinella</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Drug Screening Assays, Antitumor</term><term>HCT116 Cells</term><term>HL-60 Cells</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>KB Cells</term><term>Marine Biology</term><term>Nuclear Magnetic Resonance, Biomolecular</term><term>Polynesia</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Four bicyclic and three pentacyclic guanidine alkaloids (1-7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9-11 of known natural product crambescins, and the known crambescidins 12-15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of (1)H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC50 values ranging from 4 nM to 10 μM.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">27419263</PMID><DateCreated><Year>2016</Year><Month>08</Month><Day>26</Day></DateCreated><DateCompleted><Year>2017</Year><Month>05</Month><Day>02</Day></DateCompleted><DateRevised><Year>2017</Year><Month>05</Month><Day>02</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6025</ISSN><JournalIssue CitedMedium="Internet"><Volume>79</Volume><Issue>8</Issue><PubDate><Year>2016</Year><Month>Aug</Month><Day>26</Day></PubDate></JournalIssue><Title>Journal of natural products</Title><ISOAbbreviation>J. Nat. Prod.</ISOAbbreviation></Journal><ArticleTitle>Cytotoxic Guanidine Alkaloids from a French Polynesian Monanchora n. sp. Sponge.</ArticleTitle><Pagination><MedlinePgn>1929-37</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.jnatprod.6b00168</ELocationID><Abstract><AbstractText>Four bicyclic and three pentacyclic guanidine alkaloids (1-7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9-11 of known natural product crambescins, and the known crambescidins 12-15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of (1)H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC50 values ranging from 4 nM to 10 μM.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>El-Demerdash</LastName><ForeName>Amr</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Organic Chemistry Division, Chemistry Department, Faculty of Science, Mansoura University , Mansoura 35516, Egypt.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Moriou</LastName><ForeName>Céline</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Martin</LastName><ForeName>Marie-Thérèse</ForeName><Initials>MT</Initials><AffiliationInfo><Affiliation>Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Rodrigues-Stien</LastName><ForeName>Alice de Souza</ForeName><Initials>Ade S</Initials><AffiliationInfo><Affiliation>Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Petek</LastName><ForeName>Sylvain</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Institut de Recherche pour le Développement (IRD) , UMR-241 EIO, BP529, 98713, Papeete, Tahiti, French Polynesia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Demoy-Schneider</LastName><ForeName>Marina</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Université de la Polynésie Française , UMR-241 EIO, BP 6570, 98702 Faa'a Aéroport, Tahiti, French Polynesia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hall</LastName><ForeName>Kathryn</ForeName><Initials>K</Initials><AffiliationInfo><Affiliation>Queensland Museum , PO Box 3300, South Brisbane BC, Queensland 4101, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hooper</LastName><ForeName>John N A</ForeName><Initials>JN</Initials><AffiliationInfo><Affiliation>Queensland Museum , PO Box 3300, South Brisbane BC, Queensland 4101, Australia.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Eskitis Institute for Drug Discovery, Griffith University , Nathan, Queensland 4111, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Debitus</LastName><ForeName>Cécile</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Institut de Recherche pour le Développement (IRD) , UMR-241 EIO, BP529, 98713, Papeete, Tahiti, French Polynesia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Al-Mourabit</LastName><ForeName>Ali</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay , 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>07</Month><Day>15</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Nat Prod</MedlineTA><NlmUniqueID>7906882</NlmUniqueID><ISSNLinking>0163-3864</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000470">Alkaloids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000970">Antineoplastic Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D006146">Guanidines</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000470" MajorTopicYN="N">Alkaloids</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="Y">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000970" MajorTopicYN="N">Antineoplastic Agents</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="Y">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D047089" MajorTopicYN="N">Axinella</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004354" MajorTopicYN="N">Drug Screening Assays, Antitumor</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006146" MajorTopicYN="N">Guanidines</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="Y">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045325" MajorTopicYN="N">HCT116 Cells</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018922" MajorTopicYN="N">HL-60 Cells</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D020128" MajorTopicYN="N">Inhibitory Concentration 50</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D007624" MajorTopicYN="N">KB Cells</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008386" MajorTopicYN="N">Marine Biology</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D019906" MajorTopicYN="N">Nuclear Magnetic Resonance, Biomolecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011114" MajorTopicYN="N">Polynesia</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>7</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>7</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2017</Year><Month>5</Month><Day>4</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">27419263</ArticleId><ArticleId IdType="doi">10.1021/acs.jnatprod.6b00168</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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