Indole alkaloids from Muntafara sessilifolia with antiplasmodial and cytotoxic activities.
Identifieur interne : 000371 ( PubMed/Corpus ); précédent : 000370; suivant : 000372Indole alkaloids from Muntafara sessilifolia with antiplasmodial and cytotoxic activities.
Auteurs : Marion Girardot ; Christiane Deregnaucourt ; Alexandre Deville ; Lionel Dubost ; Roger Joyeau ; Lucile Allorge ; Philippe Rasoanaivo ; Lengo MambuSource :
- Phytochemistry [ 1873-3700 ] ; 2012.
English descriptors
- KwdEn :
- Animals, Antimalarials (chemistry), Antimalarials (isolation & purification), Antimalarials (pharmacology), Antineoplastic Agents, Phytogenic (chemistry), Antineoplastic Agents, Phytogenic (isolation & purification), Antineoplastic Agents, Phytogenic (pharmacology), Apocynaceae (chemistry), Chloroquine, Drug Screening Assays, Antitumor, Humans, Indole Alkaloids (chemistry), Indole Alkaloids (isolation & purification), Indole Alkaloids (pharmacology), Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plasmodium falciparum (drug effects), Rats, Terpenes (chemistry), Terpenes (isolation & purification), Terpenes (pharmacology).
- MESH :
- chemical , chemistry : Antimalarials, Antineoplastic Agents, Phytogenic, Indole Alkaloids, Terpenes.
- chemical , isolation & purification : Antimalarials, Antineoplastic Agents, Phytogenic, Indole Alkaloids, Terpenes.
- chemical , pharmacology : Antimalarials, Antineoplastic Agents, Phytogenic, Indole Alkaloids, Terpenes.
- chemistry : Apocynaceae.
- drug effects : Plasmodium falciparum.
- Animals, Chloroquine, Drug Screening Assays, Antitumor, Humans, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Rats.
Abstract
Four vobasinyl-iboga bisindole and one 2-acyl monomeric indole alkaloids were isolated from the stem bark of Muntafara sessilifolia along with eleven known compounds. Their structures and relative stereochemistry were elucidated on the basis of spectroscopic data including 1D and 2D NMR and mass spectrometry (MS). All isolated compounds were evaluated in vitro for antiplasmodial activity against the chloroquine-resistant strain FcB1 of Plasmodium falciparum, and for cytotoxicity against the human lung cell line MRC-5 and the rat skeletal muscle cell line L-6. 3'-Oxo-tabernaelegantine A exhibited antiplasmodial activity (4.4 μM IC(50)) associated with non-significant cytotoxicity (selectivity index of 48). Tabernaelegantine B and D displayed the highest cytotoxicity with IC(50) values of 0.47 and 1.89 μM on MRC-5 cells, and 0.42 and 2.7 μM on L-6 cells, respectively.
DOI: 10.1016/j.phytochem.2011.09.012
PubMed: 22033013
Links to Exploration step
pubmed:22033013Le document en format XML
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xml:lang="en"><term>Animals</term><term>Antimalarials (chemistry)</term><term>Antimalarials (isolation & purification)</term><term>Antimalarials (pharmacology)</term><term>Antineoplastic Agents, Phytogenic (chemistry)</term><term>Antineoplastic Agents, Phytogenic (isolation & purification)</term><term>Antineoplastic Agents, Phytogenic (pharmacology)</term><term>Apocynaceae (chemistry)</term><term>Chloroquine</term><term>Drug Screening Assays, Antitumor</term><term>Humans</term><term>Indole Alkaloids (chemistry)</term><term>Indole Alkaloids (isolation & purification)</term><term>Indole Alkaloids (pharmacology)</term><term>Molecular Structure</term><term>Nuclear Magnetic Resonance, Biomolecular</term><term>Plasmodium falciparum (drug effects)</term><term>Rats</term><term>Terpenes (chemistry)</term><term>Terpenes (isolation & purification)</term><term>Terpenes (pharmacology)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antimalarials</term><term>Antineoplastic Agents, Phytogenic</term><term>Indole Alkaloids</term><term>Terpenes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Antimalarials</term><term>Antineoplastic Agents, Phytogenic</term><term>Indole Alkaloids</term><term>Terpenes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antimalarials</term><term>Antineoplastic Agents, Phytogenic</term><term>Indole Alkaloids</term><term>Terpenes</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Apocynaceae</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Plasmodium falciparum</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Chloroquine</term><term>Drug Screening Assays, Antitumor</term><term>Humans</term><term>Molecular Structure</term><term>Nuclear Magnetic Resonance, Biomolecular</term><term>Rats</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Four vobasinyl-iboga bisindole and one 2-acyl monomeric indole alkaloids were isolated from the stem bark of Muntafara sessilifolia along with eleven known compounds. Their structures and relative stereochemistry were elucidated on the basis of spectroscopic data including 1D and 2D NMR and mass spectrometry (MS). All isolated compounds were evaluated in vitro for antiplasmodial activity against the chloroquine-resistant strain FcB1 of Plasmodium falciparum, and for cytotoxicity against the human lung cell line MRC-5 and the rat skeletal muscle cell line L-6. 3'-Oxo-tabernaelegantine A exhibited antiplasmodial activity (4.4 μM IC(50)) associated with non-significant cytotoxicity (selectivity index of 48). Tabernaelegantine B and D displayed the highest cytotoxicity with IC(50) values of 0.47 and 1.89 μM on MRC-5 cells, and 0.42 and 2.7 μM on L-6 cells, respectively.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">22033013</PMID><DateCompleted><Year>2012</Year><Month>02</Month><Day>24</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1873-3700</ISSN><JournalIssue CitedMedium="Internet"><Volume>73</Volume><Issue>1</Issue><PubDate><Year>2012</Year><Month>Jan</Month></PubDate></JournalIssue><Title>Phytochemistry</Title><ISOAbbreviation>Phytochemistry</ISOAbbreviation></Journal><ArticleTitle>Indole alkaloids from Muntafara sessilifolia with antiplasmodial and cytotoxic activities.</ArticleTitle><Pagination><MedlinePgn>65-73</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.phytochem.2011.09.012</ELocationID><Abstract><AbstractText>Four vobasinyl-iboga bisindole and one 2-acyl monomeric indole alkaloids were isolated from the stem bark of Muntafara sessilifolia along with eleven known compounds. Their structures and relative stereochemistry were elucidated on the basis of spectroscopic data including 1D and 2D NMR and mass spectrometry (MS). All isolated compounds were evaluated in vitro for antiplasmodial activity against the chloroquine-resistant strain FcB1 of Plasmodium falciparum, and for cytotoxicity against the human lung cell line MRC-5 and the rat skeletal muscle cell line L-6. 3'-Oxo-tabernaelegantine A exhibited antiplasmodial activity (4.4 μM IC(50)) associated with non-significant cytotoxicity (selectivity index of 48). Tabernaelegantine B and D displayed the highest cytotoxicity with IC(50) values of 0.47 and 1.89 μM on MRC-5 cells, and 0.42 and 2.7 μM on L-6 cells, respectively.</AbstractText><CopyrightInformation>Copyright © 2011 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Girardot</LastName><ForeName>Marion</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>UMR 7245 CNRS-MNHN Molécules de Communication et Adaptation des Micro-organismes, Département Régulations, Développement et Diversité Moléculaire, Muséum National d'Histoire Naturelle, 57 rue Cuvier CP 54, 75231 Paris Cedex 05, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Deregnaucourt</LastName><ForeName>Christiane</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Deville</LastName><ForeName>Alexandre</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Dubost</LastName><ForeName>Lionel</ForeName><Initials>L</Initials></Author><Author ValidYN="Y"><LastName>Joyeau</LastName><ForeName>Roger</ForeName><Initials>R</Initials></Author><Author ValidYN="Y"><LastName>Allorge</LastName><ForeName>Lucile</ForeName><Initials>L</Initials></Author><Author ValidYN="Y"><LastName>Rasoanaivo</LastName><ForeName>Philippe</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Mambu</LastName><ForeName>Lengo</ForeName><Initials>L</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2011</Year><Month>10</Month><Day>25</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Phytochemistry</MedlineTA><NlmUniqueID>0151434</NlmUniqueID><ISSNLinking>0031-9422</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C570161">3'-oxo-tabernaelegantine A</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000962">Antimalarials</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000972">Antineoplastic Agents, Phytogenic</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D026121">Indole Alkaloids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D013729">Terpenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C570162">tabernaelegantine B</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C570163">tabernaelegantine D</NameOfSubstance></Chemical><Chemical><RegistryNumber>886U3H6UFF</RegistryNumber><NameOfSubstance UI="D002738">Chloroquine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000818" 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MajorTopicYN="N">Chloroquine</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004354" MajorTopicYN="N">Drug Screening Assays, Antitumor</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D026121" MajorTopicYN="N">Indole 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="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D019906" MajorTopicYN="N">Nuclear Magnetic Resonance, Biomolecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010963" MajorTopicYN="N">Plasmodium falciparum</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D051381" MajorTopicYN="N">Rats</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013729" MajorTopicYN="N">Terpenes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="Y">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2011</Year><Month>06</Month><Day>08</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2011</Year><Month>09</Month><Day>23</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2011</Year><Month>09</Month><Day>30</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2011</Year><Month>10</Month><Day>29</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate 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