Antiplasmodial phenolic compounds from Piptadenia pervillei.
Identifieur interne : 000111 ( Ncbi/Merge ); précédent : 000110; suivant : 000112Antiplasmodial phenolic compounds from Piptadenia pervillei.
Auteurs : Voahangy Ramanandraibe [Madagascar] ; Philippe Grellier ; Marie-Thérèse Martin ; Alexandre Deville ; Roger Joyeau ; David Ramanitrahasimbola ; Elisabeth Mouray ; Philippe Rasoanaivo ; Lengo MambuSource :
- Planta medica [ 0032-0943 ] ; 2008.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Antimalarials, Antineoplastic Agents, Phytogenic, Phenols.
- chemical , pharmacology : Antimalarials, Antineoplastic Agents, Phytogenic.
- chemistry : Fabaceae.
- drug effects : Plasmodium falciparum.
- Animals, Cell Line, Humans, Molecular Structure.
Abstract
Piptadenia pervillei Vatke (Fabaceae) was selected from a screening programme devoted to the search of naturally-occuring antimalarial compounds from plants of Madagascar. Bioassay-guided fractionation of the ethyl acetate extract of the leaves led to the isolation of four phenolic compounds, (+)-catechin ( 1), (+)-catechin 5-gallate ( 2), (+)-catechin 3-gallate ( 3) and ethyl gallate ( 4). Structures were determined by NMR and mass spectroscopy. Compounds 2 and 3 displayed the highest in vitro activity against the chloroquine-resistant strain FcB1 of Plasmodium falciparum with IC (50) values of 1.2 microM and 1.0 microM, respectively, and no significant cytotoxicity against the human embryonic lung cells MRC-5 was measured (IC (50) values > 75 microM). Five analogues ( 5 - 9) of (+)-catechin 5-gallate ( 2) were synthesized and evaluated for their antiplasmodial activity.
DOI: 10.1055/s-2008-1034328
PubMed: 18484535
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xml:lang="en"><term>Animals</term><term>Antimalarials (chemistry)</term><term>Antimalarials (pharmacology)</term><term>Antineoplastic Agents, Phytogenic (chemistry)</term><term>Antineoplastic Agents, Phytogenic (pharmacology)</term><term>Cell Line</term><term>Fabaceae (chemistry)</term><term>Humans</term><term>Molecular Structure</term><term>Phenols (chemistry)</term><term>Plasmodium falciparum (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Antinéoplasiques d'origine végétale ()</term><term>Antinéoplasiques d'origine végétale (pharmacologie)</term><term>Antipaludiques ()</term><term>Antipaludiques (pharmacologie)</term><term>Fabaceae ()</term><term>Humains</term><term>Lignée cellulaire</term><term>Phénols ()</term><term>Plasmodium falciparum ()</term><term>Structure moléculaire</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antimalarials</term><term>Antineoplastic Agents, 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moléculaire</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Piptadenia pervillei Vatke (Fabaceae) was selected from a screening programme devoted to the search of naturally-occuring antimalarial compounds from plants of Madagascar. Bioassay-guided fractionation of the ethyl acetate extract of the leaves led to the isolation of four phenolic compounds, (+)-catechin ( 1), (+)-catechin 5-gallate ( 2), (+)-catechin 3-gallate ( 3) and ethyl gallate ( 4). Structures were determined by NMR and mass spectroscopy. Compounds 2 and 3 displayed the highest in vitro activity against the chloroquine-resistant strain FcB1 of Plasmodium falciparum with IC (50) values of 1.2 microM and 1.0 microM, respectively, and no significant cytotoxicity against the human embryonic lung cells MRC-5 was measured (IC (50) values > 75 microM). Five analogues ( 5 - 9) of (+)-catechin 5-gallate ( 2) were synthesized and evaluated for their antiplasmodial activity.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">18484535</PMID><DateCompleted><Year>2008</Year><Month>11</Month><Day>04</Day></DateCompleted><DateRevised><Year>2008</Year><Month>05</Month><Day>19</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0032-0943</ISSN><JournalIssue CitedMedium="Print"><Volume>74</Volume><Issue>4</Issue><PubDate><Year>2008</Year><Month>Mar</Month></PubDate></JournalIssue><Title>Planta medica</Title><ISOAbbreviation>Planta Med.</ISOAbbreviation></Journal><ArticleTitle>Antiplasmodial phenolic compounds from Piptadenia pervillei.</ArticleTitle><Pagination><MedlinePgn>417-21</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1055/s-2008-1034328</ELocationID><Abstract><AbstractText>Piptadenia pervillei Vatke (Fabaceae) was selected from a screening programme devoted to the search of naturally-occuring antimalarial compounds from plants of Madagascar. Bioassay-guided fractionation of the ethyl acetate extract of the leaves led to the isolation of four phenolic compounds, (+)-catechin ( 1), (+)-catechin 5-gallate ( 2), (+)-catechin 3-gallate ( 3) and ethyl gallate ( 4). Structures were determined by NMR and mass spectroscopy. Compounds 2 and 3 displayed the highest in vitro activity against the chloroquine-resistant strain FcB1 of Plasmodium falciparum with IC (50) values of 1.2 microM and 1.0 microM, respectively, and no significant cytotoxicity against the human embryonic lung cells MRC-5 was measured (IC (50) values > 75 microM). Five analogues ( 5 - 9) of (+)-catechin 5-gallate ( 2) were synthesized and evaluated for their antiplasmodial activity.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Ramanandraibe</LastName><ForeName>Voahangy</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>Laboratoire de Bio-thérapeutique, Institut Malgache de Recherches Appliquées, Antananarivo, Madagascar.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Grellier</LastName><ForeName>Philippe</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Martin</LastName><ForeName>Marie-Thérèse</ForeName><Initials>MT</Initials></Author><Author ValidYN="Y"><LastName>Deville</LastName><ForeName>Alexandre</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Joyeau</LastName><ForeName>Roger</ForeName><Initials>R</Initials></Author><Author ValidYN="Y"><LastName>Ramanitrahasimbola</LastName><ForeName>David</ForeName><Initials>D</Initials></Author><Author ValidYN="Y"><LastName>Mouray</LastName><ForeName>Elisabeth</ForeName><Initials>E</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></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Planta Med</MedlineTA><NlmUniqueID>0066751</NlmUniqueID><ISSNLinking>0032-0943</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance 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uniqKey="Joyeau R" first="Roger" last="Joyeau">Roger Joyeau</name><name sortKey="Mambu, Lengo" sort="Mambu, Lengo" uniqKey="Mambu L" first="Lengo" last="Mambu">Lengo Mambu</name><name sortKey="Martin, Marie Therese" sort="Martin, Marie Therese" uniqKey="Martin M" first="Marie-Thérèse" last="Martin">Marie-Thérèse Martin</name><name sortKey="Mouray, Elisabeth" sort="Mouray, Elisabeth" uniqKey="Mouray E" first="Elisabeth" last="Mouray">Elisabeth Mouray</name><name sortKey="Ramanitrahasimbola, David" sort="Ramanitrahasimbola, David" uniqKey="Ramanitrahasimbola D" first="David" last="Ramanitrahasimbola">David Ramanitrahasimbola</name><name sortKey="Rasoanaivo, Philippe" sort="Rasoanaivo, Philippe" uniqKey="Rasoanaivo P" first="Philippe" last="Rasoanaivo">Philippe Rasoanaivo</name></noCountry><country name="Madagascar"><noRegion><name sortKey="Ramanandraibe, Voahangy" sort="Ramanandraibe, Voahangy" uniqKey="Ramanandraibe V" first="Voahangy" last="Ramanandraibe">Voahangy 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