Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia
Identifieur interne : 001334 ( Main/Exploration ); précédent : 001333; suivant : 001335Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia
Auteurs : Marion Girardot ; Alice Gadea ; Christiane Deregnaucourt ; Alexandre Deville ; Lionel Dubost ; Bastien Nay ; Alexandre Maciuk [France] ; Philippe Rasoanaivo [Madagascar] ; Lengo Mambu [France]Source :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2012-05.
Descripteurs français
- Pascal (Inist)
- Activité biologique, Acétate, Alcaloïde, Aminoaldéhyde, Analyse structurale, Antipaludique, Biosynthèse, Composé naturel, Cytotoxicité, Dérivé de l'indole, Ecorce, Essai biologique, Homme, Hétérocycle azote, Isolement, Lignée L6, Lignée MRC5, Lignée cellulaire, Muntafara sessilifolia, Origine végétale, Plasmodium falciparum, Rat, Spectrométrie RMN, Spectrométrie masse, Structure moléculaire, Sélectivité, Tabernaelegantinal, Tige.
- Wicri :
- topic : Homme.
English descriptors
- KwdEn :
- Acetate, Alkaloid, Aminoaldehyde, Antimalarial, Bark, Bioassay, Biological activity, Biosynthesis, Cell line, Cytotoxicity, Human, Indole derivatives, Isolation, Mass spectrometry, Molecular structure, NMR spectrometry, Natural compound, Nitrogen heterocycle, Plant origin, Plasmodium falciparum, Rat, Selectivity, Stem, Structural analysis.
- Teeft :
- Aldehyde, Aldehyde group, Aldehyde proton, Alkaloid, Alkaloidal crude, Amorphous powder, Antiplasmodial, Baerheim svendsen, Bisindole, Bisindole alkaloids, Chem, Chemical shifts, Cosy spectrum, Cytotoxic, Cytotoxic activities, Ethyl chain, Falciparum, Flow rate, Full paper, Gmbh, Hmbc, Hrms, Hrms spectrum, Hsqc spectrum, Iboga, Iboga moieties, Iboga moiety, Indole, Kgaa, Mammalian cells, Meoh, Moiety, Molecular formula, Muntafara, Muntafara sessilifolia, Noesy, Plasmodium falciparum, Proton, Sessilifolia, Spectroscopic, Spectroscopic data, Verlag, Verlag gmbh, Vobasinyl, Vobasinyl moiety, Weinheim.
Abstract
Bioassay‐guided fractionation of the stem bark of Muntafara sessilifolia has led to the isolation of six new vobasinyl‐iboga bisindole alkaloids, tabernaelegantinals A, B and E, and (3′R)‐hydroxytabernaelegantines A, C and D, together with six known monomeric indole and two bisindole alkaloids. The structures of these alkaloids were established by NMR and MS analysis. The bisindole alkaloids demonstrated cytotoxicity against the human lung MRC‐5 and rat skeletal muscle L‐6 cell lines whereas only one monomeric indole alkaloid was found to be cytotoxic. Tabernaemontanine acetate was found to be selectively antiplasmodial against the chloroquine‐resistant strain FcB1 of Plasmodium falciparum (5.3 μM IC50) over mammalian cell lines (selectivity index > 45). The tabernaelegantinals share an unprecedented α‐amino aldehyde moiety, the biosynthetic origin of which is discussed.
Six new vobasinyl‐iboga bisindole alkaloids and eight known compounds have been isolated from the stem bark ofMuntafara sessilifolia. Their structures were elucidated by NMR and MS and three of them were found to bear an unprecedented α‐amino aldehyde group. The biosynthetic origin of these bisindoles is proposed. Their antiplasmodial and cytotoxic activities have been evaluated.
Url:
DOI: 10.1002/ejoc.201101738
Affiliations:
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The structures of these alkaloids were established by NMR and MS analysis. The bisindole alkaloids demonstrated cytotoxicity against the human lung MRC‐5 and rat skeletal muscle L‐6 cell lines whereas only one monomeric indole alkaloid was found to be cytotoxic. Tabernaemontanine acetate was found to be selectively antiplasmodial against the chloroquine‐resistant strain FcB1 of Plasmodium falciparum (5.3 μM IC50) over mammalian cell lines (selectivity index > 45). The tabernaelegantinals share an unprecedented α‐amino aldehyde moiety, the biosynthetic origin of which is discussed.</div><div type="abstract" xml:lang="en">Six new vobasinyl‐iboga bisindole alkaloids and eight known compounds have been isolated from the stem bark ofMuntafara sessilifolia. Their structures were elucidated by NMR and MS and three of them were found to bear an unprecedented α‐amino aldehyde group. The biosynthetic origin of these bisindoles is proposed. Their antiplasmodial and cytotoxic activities have been evaluated.</div></front></TEI><affiliations><list><country><li>France</li><li>Madagascar</li></country><region><li>Île-de-France</li></region><settlement><li>Châtenay‐Malabry</li></settlement></list><tree><noCountry><name sortKey="Deregnaucourt, Christiane" sort="Deregnaucourt, Christiane" uniqKey="Deregnaucourt C" first="Christiane" last="Deregnaucourt">Christiane Deregnaucourt</name><name sortKey="Deville, Alexandre" sort="Deville, Alexandre" uniqKey="Deville A" first="Alexandre" last="Deville">Alexandre Deville</name><name sortKey="Dubost, Lionel" sort="Dubost, Lionel" uniqKey="Dubost L" first="Lionel" last="Dubost">Lionel Dubost</name><name sortKey="Gadea, Alice" sort="Gadea, Alice" uniqKey="Gadea A" first="Alice" last="Gadea">Alice Gadea</name><name sortKey="Girardot, Marion" sort="Girardot, Marion" uniqKey="Girardot M" first="Marion" last="Girardot">Marion Girardot</name><name sortKey="Nay, Bastien" sort="Nay, Bastien" uniqKey="Nay B" first="Bastien" last="Nay">Bastien Nay</name></noCountry><country name="France"><region name="Île-de-France"><name sortKey="Maciuk, Alexandre" sort="Maciuk, Alexandre" uniqKey="Maciuk A" first="Alexandre" last="Maciuk">Alexandre Maciuk</name></region><name sortKey="Mambu, Lengo" sort="Mambu, Lengo" uniqKey="Mambu L" first="Lengo" last="Mambu">Lengo Mambu</name></country><country name="Madagascar"><noRegion><name sortKey="Rasoanaivo, Philippe" sort="Rasoanaivo, Philippe" uniqKey="Rasoanaivo P" first="Philippe" last="Rasoanaivo">Philippe Rasoanaivo</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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