ChloroquineV1, Main, Merge, bibRecord, 001452

Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia

Identifieur interne : 001452 ( Main/Merge ); précédent : 001451; suivant : 001453

Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia

Auteurs : Marion Girardot [France] ; Alice Gadea [France] ; Christiane Deregnaucourt [France] ; Alexandre Deville [France] ; Lionel Dubost [France] ; Bastien Nay [France] ; Alexandre Maciuk [France] ; Philippe Rasoanaivo [Madagascar] ; Lengo Mambu [France]

Source :

European journal of organic chemistry : (Print) [ 1434-193X ] ; 2012.

RBID : Pascal:12-0322483

Descripteurs français

Pascal (Inist)
- Cytotoxicité, Dérivé de l'indole, Alcaloïde, Essai biologique, Tige, Ecorce, Isolement, Structure moléculaire, Spectrométrie RMN, Spectrométrie masse, Homme, Rat, Acétate, Sélectivité, Antipaludique, Plasmodium falciparum, Lignée cellulaire, Aminoaldéhyde, Biosynthèse, Composé naturel, Analyse structurale, Activité biologique, Hétérocycle azote, Origine végétale, Lignée MRC5, Lignée L6, Muntafara sessilifolia, Tabernaelegantinal.
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.

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.

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Pascal:12-0322483

Le document en format XML

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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acetate</term>
<term>Alkaloid</term>
<term>Aminoaldehyde</term>
<term>Antimalarial</term>
<term>Bark</term>
<term>Bioassay</term>
<term>Biological activity</term>
<term>Biosynthesis</term>
<term>Cell line</term>
<term>Cytotoxicity</term>
<term>Human</term>
<term>Indole derivatives</term>
<term>Isolation</term>
<term>Mass spectrometry</term>
<term>Molecular structure</term>
<term>NMR spectrometry</term>
<term>Natural compound</term>
<term>Nitrogen heterocycle</term>
<term>Plant origin</term>
<term>Plasmodium falciparum</term>
<term>Rat</term>
<term>Selectivity</term>
<term>Stem</term>
<term>Structural analysis</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Cytotoxicité</term>
<term>Dérivé de l'indole</term>
<term>Alcaloïde</term>
<term>Essai biologique</term>
<term>Tige</term>
<term>Ecorce</term>
<term>Isolement</term>
<term>Structure moléculaire</term>
<term>Spectrométrie RMN</term>
<term>Spectrométrie masse</term>
<term>Homme</term>
<term>Rat</term>
<term>Acétate</term>
<term>Sélectivité</term>
<term>Antipaludique</term>
<term>Plasmodium falciparum</term>
<term>Lignée cellulaire</term>
<term>Aminoaldéhyde</term>
<term>Biosynthèse</term>
<term>Composé naturel</term>
<term>Analyse structurale</term>
<term>Activité biologique</term>
<term>Hétérocycle azote</term>
<term>Origine végétale</term>
<term>Lignée MRC5</term>
<term>Lignée L6</term>
<term>Muntafara sessilifolia</term>
<term>Tabernaelegantinal</term>
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<front><div type="abstract" xml:lang="en">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 IC<sub>50</sub>
) over mammalian cell lines (selectivity index > 45). The tabernaelegantinals share an unprecedented α-amino aldehyde moiety, the biosynthetic origin of which is discussed.</div>
</front>
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<tree><country name="France"><region name="Île-de-France"><name sortKey="Girardot, Marion" sort="Girardot, Marion" uniqKey="Girardot M" first="Marion" last="Girardot">Marion Girardot</name>
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<name sortKey="Maciuk, Alexandre" sort="Maciuk, Alexandre" uniqKey="Maciuk A" first="Alexandre" last="Maciuk">Alexandre Maciuk</name>
<name sortKey="Mambu, Lengo" sort="Mambu, Lengo" uniqKey="Mambu L" first="Lengo" last="Mambu">Lengo Mambu</name>
<name sortKey="Nay, Bastien" sort="Nay, Bastien" uniqKey="Nay B" first="Bastien" last="Nay">Bastien Nay</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>

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   |texte=   Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia
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Serveur d'exploration Chloroquine

Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia

Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia

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