Antiplasmodial Phenolic Compounds from Piptadenia pervillei
Identifieur interne : 001A43 ( Main/Curation ); précédent : 001A42; suivant : 001A44Antiplasmodial Phenolic Compounds from Piptadenia pervillei
Auteurs : Voahangy Ramanandraibe [Madagascar] ; Philippe Grellier [France] ; Marie-Thérèse Martin [France] ; Alexandre Deville [France] ; Roger Joyeau [France] ; David Ramanitrahasimbola [Madagascar] ; Elisabeth Mouray [France] ; Philippe Rasoanaivo [Madagascar] ; Lengo Mambu [France]Source :
- Planta medica [ 0032-0943 ] ; 2008.
Descripteurs français
- KwdFr :
- MESH :
- pharmacologie : Antinéoplasiques d'origine végétale, Antipaludiques.
- Pascal (Inist)
- Wicri :
- topic : Plante médicinale.
English descriptors
- KwdEn :
- Animals, Antimalarial, Antimalarials (chemistry), Antimalarials (pharmacology), Antineoplastic Agents, Phytogenic (chemistry), Antineoplastic Agents, Phytogenic (pharmacology), Cell Line, Fabaceae (chemistry), Humans, Leguminosae, Medicinal plant, Molecular Structure, Parasiticide, Pharmacognosy, Phenols (chemistry), Plant origin, Plasmodium falciparum (drug effects).
- 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 FcBl of Plasmodium falciparum with ICso values of 1.2 pM and 1.0 pM, respectively, and no significant cytotoxicity against the human embryonic lung cells MRC-5 was measured (IC50 values >75μM). Five analogues (5-9) of (+)-catechin 5-gallate (2) were synthesized and evaluated for their antiplasmodial activity.
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Pascal:08-0207828Le document en format XML
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<author><name sortKey="Ramanitrahasimbola, David" sort="Ramanitrahasimbola, David" uniqKey="Ramanitrahasimbola D" first="David" last="Ramanitrahasimbola">David Ramanitrahasimbola</name>
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<term>Antipaludiques</term>
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<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 FcBl of Plasmodium falciparum with IC<sub>so</sub>
values of 1.2 pM and 1.0 pM, respectively, and no significant cytotoxicity against the human embryonic lung cells MRC-5 was measured (IC<sub>50</sub>
values >75μM). Five analogues (5-9) of (+)-catechin 5-gallate (2) were synthesized and evaluated for their antiplasmodial activity.</div>
</front>
</TEI>
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<s3>MDG</s3>
<sZ>1 aut.</sZ>
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<region type="old region">Île-de-France</region>
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<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Laboratoire de Bio-thérapeutique, Institut Malgache de Recherches Appliquées</s1>
<s2>Antananarivo</s2>
<s3>MDG</s3>
<sZ>1 aut.</sZ>
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</inist:fA14>
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</affiliation>
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<s2>Paris</s2>
<s3>FRA</s3>
<sZ>2 aut.</sZ>
<sZ>7 aut.</sZ>
</inist:fA14>
<country>France</country>
<placeName><region type="region">Île-de-France</region>
<region type="old region">Île-de-France</region>
<settlement type="city">Paris</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Rasoanaivo, Philippe" sort="Rasoanaivo, Philippe" uniqKey="Rasoanaivo P" first="Philippe" last="Rasoanaivo">Philippe Rasoanaivo</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Laboratoire de Bio-thérapeutique, Institut Malgache de Recherches Appliquées</s1>
<s2>Antananarivo</s2>
<s3>MDG</s3>
<sZ>1 aut.</sZ>
<sZ>6 aut.</sZ>
<sZ>8 aut.</sZ>
</inist:fA14>
<country>Madagascar</country>
<wicri:noRegion>Antananarivo</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Mambu, Lengo" sort="Mambu, Lengo" uniqKey="Mambu L" first="Lengo" last="Mambu">Lengo Mambu</name>
<affiliation wicri:level="3"><inist:fA14 i1="04"><s1>USM 0502-UMR 5154 CNRS Chimie et Biochimie des Substances Naturelles, Département Régulations, Développement et Diversité Moléculaire, Muséum National d'Histoire Naturelle</s1>
<s2>Paris</s2>
<s3>FRA</s3>
<sZ>4 aut.</sZ>
<sZ>5 aut.</sZ>
<sZ>9 aut.</sZ>
</inist:fA14>
<country>France</country>
<placeName><region type="region">Île-de-France</region>
<region type="old region">Île-de-France</region>
<settlement type="city">Paris</settlement>
</placeName>
</affiliation>
</author>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">Antiplasmodial Phenolic Compounds from Piptadenia pervillei</title>
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<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Laboratoire de Bio-thérapeutique, Institut Malgache de Recherches Appliquées</s1>
<s2>Antananarivo</s2>
<s3>MDG</s3>
<sZ>1 aut.</sZ>
<sZ>6 aut.</sZ>
<sZ>8 aut.</sZ>
</inist:fA14>
<country>Madagascar</country>
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</affiliation>
</author>
<author><name sortKey="Grellier, Philippe" sort="Grellier, Philippe" uniqKey="Grellier P" first="Philippe" last="Grellier">Philippe Grellier</name>
<affiliation wicri:level="3"><inist:fA14 i1="02"><s1>USM 0504 Biologie Fonctionnelle des Protozoaires, Département Régulations, Développement et Diversité Moléculaire, Muséum National d'Histoire Naturelle</s1>
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<sZ>2 aut.</sZ>
<sZ>7 aut.</sZ>
</inist:fA14>
<country>France</country>
<placeName><region type="region">Île-de-France</region>
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</placeName>
</affiliation>
</author>
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<affiliation wicri:level="3"><inist:fA14 i1="03"><s1>Institut de Chimie des Substances Naturelles, CNRS</s1>
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</inist:fA14>
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<sZ>4 aut.</sZ>
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<sZ>9 aut.</sZ>
</inist:fA14>
<country>France</country>
<placeName><region type="region">Île-de-France</region>
<region type="old region">Île-de-France</region>
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</placeName>
</affiliation>
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<author><name sortKey="Joyeau, Roger" sort="Joyeau, Roger" uniqKey="Joyeau R" first="Roger" last="Joyeau">Roger Joyeau</name>
<affiliation wicri:level="3"><inist:fA14 i1="04"><s1>USM 0502-UMR 5154 CNRS Chimie et Biochimie des Substances Naturelles, Département Régulations, Développement et Diversité Moléculaire, Muséum National d'Histoire Naturelle</s1>
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<sZ>4 aut.</sZ>
<sZ>5 aut.</sZ>
<sZ>9 aut.</sZ>
</inist:fA14>
<country>France</country>
<placeName><region type="region">Île-de-France</region>
<region type="old region">Île-de-France</region>
<settlement type="city">Paris</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Ramanitrahasimbola, David" sort="Ramanitrahasimbola, David" uniqKey="Ramanitrahasimbola D" first="David" last="Ramanitrahasimbola">David Ramanitrahasimbola</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Laboratoire de Bio-thérapeutique, Institut Malgache de Recherches Appliquées</s1>
<s2>Antananarivo</s2>
<s3>MDG</s3>
<sZ>1 aut.</sZ>
<sZ>6 aut.</sZ>
<sZ>8 aut.</sZ>
</inist:fA14>
<country>Madagascar</country>
<wicri:noRegion>Antananarivo</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Mouray, Elisabeth" sort="Mouray, Elisabeth" uniqKey="Mouray E" first="Elisabeth" last="Mouray">Elisabeth Mouray</name>
<affiliation wicri:level="3"><inist:fA14 i1="02"><s1>USM 0504 Biologie Fonctionnelle des Protozoaires, Département Régulations, Développement et Diversité Moléculaire, Muséum National d'Histoire Naturelle</s1>
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<s3>FRA</s3>
<sZ>2 aut.</sZ>
<sZ>7 aut.</sZ>
</inist:fA14>
<country>France</country>
<placeName><region type="region">Île-de-France</region>
<region type="old region">Île-de-France</region>
<settlement type="city">Paris</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Rasoanaivo, Philippe" sort="Rasoanaivo, Philippe" uniqKey="Rasoanaivo P" first="Philippe" last="Rasoanaivo">Philippe Rasoanaivo</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Laboratoire de Bio-thérapeutique, Institut Malgache de Recherches Appliquées</s1>
<s2>Antananarivo</s2>
<s3>MDG</s3>
<sZ>1 aut.</sZ>
<sZ>6 aut.</sZ>
<sZ>8 aut.</sZ>
</inist:fA14>
<country>Madagascar</country>
<wicri:noRegion>Antananarivo</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Mambu, Lengo" sort="Mambu, Lengo" uniqKey="Mambu L" first="Lengo" last="Mambu">Lengo Mambu</name>
<affiliation wicri:level="3"><inist:fA14 i1="04"><s1>USM 0502-UMR 5154 CNRS Chimie et Biochimie des Substances Naturelles, Département Régulations, Développement et Diversité Moléculaire, Muséum National d'Histoire Naturelle</s1>
<s2>Paris</s2>
<s3>FRA</s3>
<sZ>4 aut.</sZ>
<sZ>5 aut.</sZ>
<sZ>9 aut.</sZ>
</inist:fA14>
<country>France</country>
<placeName><region type="region">Île-de-France</region>
<region type="old region">Île-de-France</region>
<settlement type="city">Paris</settlement>
</placeName>
</affiliation>
</author>
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<series><title level="j" type="main">Planta medica</title>
<title level="j" type="abbreviated">Planta med.</title>
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<term>Leguminosae</term>
<term>Medicinal plant</term>
<term>Parasiticide</term>
<term>Pharmacognosy</term>
<term>Plant origin</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Antipaludique</term>
<term>Leguminosae</term>
<term>Pharmacognosie</term>
<term>Plante médicinale</term>
<term>Origine végétale</term>
<term>Antiparasitaire</term>
<term>Catéchine gallate</term>
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<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 FcBl of Plasmodium falciparum with IC<sub>so</sub>
values of 1.2 pM and 1.0 pM, respectively, and no significant cytotoxicity against the human embryonic lung cells MRC-5 was measured (IC<sub>50</sub>
values >75μM). Five analogues (5-9) of (+)-catechin 5-gallate (2) were synthesized and evaluated for their antiplasmodial activity.</div>
</front>
</TEI>
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</author>
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</author>
</analytic>
<series><title level="j">Planta medica</title>
<idno type="ISSN">0032-0943</idno>
<imprint><date when="2008" type="published">2008</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" 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, Phytogenic</term>
<term>Phenols</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antimalarials</term>
<term>Antineoplastic Agents, Phytogenic</term>
</keywords>
<keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Fabaceae</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Plasmodium falciparum</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antinéoplasiques d'origine végétale</term>
<term>Antipaludiques</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Animals</term>
<term>Cell Line</term>
<term>Humans</term>
<term>Molecular Structure</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Animaux</term>
<term>Antinéoplasiques d'origine végétale</term>
<term>Antipaludiques</term>
<term>Fabaceae</term>
<term>Humains</term>
<term>Lignée cellulaire</term>
<term>Phénols</term>
<term>Plasmodium falciparum</term>
<term>Structure 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>
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