ChloroquineV1, PascalFrancis, Checkpoint, bibRecord, 000008

Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia

Identifieur interne : 000008 ( PascalFrancis/Checkpoint ); précédent : 000007; suivant : 000009

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.

Affiliations:

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Le document en format XML

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<series><title level="j" type="main">European journal of organic chemistry : (Print)</title>
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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>
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<fA11 i1="01" i2="1"><s1>GIRARDOT (Marion)</s1>
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<fA11 i1="09" i2="1"><s1>MAMBU (Lengo)</s1>
</fA11>
<fA14 i1="01"><s1>Museum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS-MNHN. 57 rue Cuvier (CP 54)</s1>
<s2>75005 Paris</s2>
<s3>FRA</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>4 aut.</sZ>
<sZ>5 aut.</sZ>
<sZ>6 aut.</sZ>
<sZ>9 aut.</sZ>
</fA14>
<fA14 i1="02"><s1>Université Paris-Sud, Faculté de Pharmacie, UMR 8076 CNRS (BioCIS) Laboratoire de Pharmacognosie, 5 rue J.-B. Clément</s1>
<s2>92296 Châtenay-Malabry</s2>
<s3>FRA</s3>
<sZ>7 aut.</sZ>
</fA14>
<fA14 i1="03"><s1>Institut Malgache de Recherches Appliquées, BP 3833</s1>
<s2>101 Antananarivo</s2>
<s3>MDG</s3>
<sZ>8 aut.</sZ>
</fA14>
<fA20><s1>2816-2823</s1>
</fA20>
<fA21><s1>2012</s1>
</fA21>
<fA23 i1="01"><s0>ENG</s0>
</fA23>
<fA43 i1="01"><s1>INIST</s1>
<s2>26693</s2>
<s5>354000507917230180</s5>
</fA43>
<fA44><s0>0000</s0>
<s1>© 2012 INIST-CNRS. All rights reserved.</s1>
</fA44>
<fA45><s0>21 ref.</s0>
</fA45>
<fA47 i1="01" i2="1"><s0>12-0322483</s0>
</fA47>
<fA60><s1>P</s1>
</fA60>
<fA61><s0>A</s0>
</fA61>
<fA64 i1="01" i2="1"><s0>European journal of organic chemistry : (Print)</s0>
</fA64>
<fA66 i1="01"><s0>DEU</s0>
</fA66>
<fC01 i1="01" l="ENG"><s0>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.</s0>
</fC01>
<fC02 i1="01" i2="X"><s0>001C03C06B</s0>
</fC02>
<fC02 i1="02" i2="X"><s0>002B02S06</s0>
</fC02>
<fC02 i1="03" i2="X"><s0>002A31C06</s0>
</fC02>
<fC02 i1="04" i2="X"><s0>215</s0>
</fC02>
<fC03 i1="01" i2="X" l="FRE"><s0>Cytotoxicité</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="ENG"><s0>Cytotoxicity</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="SPA"><s0>Citotoxicidad</s0>
<s5>01</s5>
</fC03>
<fC03 i1="02" i2="X" l="FRE"><s0>Dérivé de l'indole</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="ENG"><s0>Indole derivatives</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="SPA"><s0>Indol derivado</s0>
<s5>02</s5>
</fC03>
<fC03 i1="03" i2="X" l="FRE"><s0>Alcaloïde</s0>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="ENG"><s0>Alkaloid</s0>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="SPA"><s0>Alcaloide</s0>
<s5>03</s5>
</fC03>
<fC03 i1="04" i2="X" l="FRE"><s0>Essai biologique</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG"><s0>Bioassay</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA"><s0>Prueba biológica</s0>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE"><s0>Tige</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="ENG"><s0>Stem</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="SPA"><s0>Tallo</s0>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE"><s0>Ecorce</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG"><s0>Bark</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA"><s0>Corteza(vegetal)</s0>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>Isolement</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG"><s0>Isolation</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>Aislamiento</s0>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Structure moléculaire</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Molecular structure</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Estructura molecular</s0>
<s5>08</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Spectrométrie RMN</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>NMR spectrometry</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Espectrometría RMN</s0>
<s5>09</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Spectrométrie masse</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Mass spectrometry</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Espectrometría masa</s0>
<s5>10</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>Homme</s0>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>Human</s0>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA"><s0>Hombre</s0>
<s5>11</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>Rat</s0>
<s5>12</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG"><s0>Rat</s0>
<s5>12</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA"><s0>Rata</s0>
<s5>12</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Acétate</s0>
<s2>NA</s2>
<s5>13</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG"><s0>Acetate</s0>
<s2>NA</s2>
<s5>13</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA"><s0>Acetato</s0>
<s2>NA</s2>
<s5>13</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Sélectivité</s0>
<s5>14</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG"><s0>Selectivity</s0>
<s5>14</s5>
</fC03>
<fC03 i1="14" i2="X" l="SPA"><s0>Selectividad</s0>
<s5>14</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE"><s0>Antipaludique</s0>
<s5>15</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG"><s0>Antimalarial</s0>
<s5>15</s5>
</fC03>
<fC03 i1="15" i2="X" l="SPA"><s0>Antipalúdico</s0>
<s5>15</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE"><s0>Plasmodium falciparum</s0>
<s2>NS</s2>
<s5>16</s5>
</fC03>
<fC03 i1="16" i2="X" l="ENG"><s0>Plasmodium falciparum</s0>
<s2>NS</s2>
<s5>16</s5>
</fC03>
<fC03 i1="16" i2="X" l="SPA"><s0>Plasmodium falciparum</s0>
<s2>NS</s2>
<s5>16</s5>
</fC03>
<fC03 i1="17" i2="X" l="FRE"><s0>Lignée cellulaire</s0>
<s5>17</s5>
</fC03>
<fC03 i1="17" i2="X" l="ENG"><s0>Cell line</s0>
<s5>17</s5>
</fC03>
<fC03 i1="17" i2="X" l="SPA"><s0>Línea celular</s0>
<s5>17</s5>
</fC03>
<fC03 i1="18" i2="X" l="FRE"><s0>Aminoaldéhyde</s0>
<s5>18</s5>
</fC03>
<fC03 i1="18" i2="X" l="ENG"><s0>Aminoaldehyde</s0>
<s5>18</s5>
</fC03>
<fC03 i1="18" i2="X" l="SPA"><s0>Aminoaldehído</s0>
<s5>18</s5>
</fC03>
<fC03 i1="19" i2="X" l="FRE"><s0>Biosynthèse</s0>
<s5>19</s5>
</fC03>
<fC03 i1="19" i2="X" l="ENG"><s0>Biosynthesis</s0>
<s5>19</s5>
</fC03>
<fC03 i1="19" i2="X" l="SPA"><s0>Biosíntesis</s0>
<s5>19</s5>
</fC03>
<fC03 i1="20" i2="X" l="FRE"><s0>Composé naturel</s0>
<s5>20</s5>
</fC03>
<fC03 i1="20" i2="X" l="ENG"><s0>Natural compound</s0>
<s5>20</s5>
</fC03>
<fC03 i1="20" i2="X" l="SPA"><s0>Compuesto natural</s0>
<s5>20</s5>
</fC03>
<fC03 i1="21" i2="X" l="FRE"><s0>Analyse structurale</s0>
<s5>21</s5>
</fC03>
<fC03 i1="21" i2="X" l="ENG"><s0>Structural analysis</s0>
<s5>21</s5>
</fC03>
<fC03 i1="21" i2="X" l="SPA"><s0>Análisis estructural</s0>
<s5>21</s5>
</fC03>
<fC03 i1="22" i2="X" l="FRE"><s0>Activité biologique</s0>
<s5>22</s5>
</fC03>
<fC03 i1="22" i2="X" l="ENG"><s0>Biological activity</s0>
<s5>22</s5>
</fC03>
<fC03 i1="22" i2="X" l="SPA"><s0>Actividad biológica</s0>
<s5>22</s5>
</fC03>
<fC03 i1="23" i2="X" l="FRE"><s0>Hétérocycle azote</s0>
<s5>41</s5>
</fC03>
<fC03 i1="23" i2="X" l="ENG"><s0>Nitrogen heterocycle</s0>
<s5>41</s5>
</fC03>
<fC03 i1="23" i2="X" l="SPA"><s0>Heterociclo nitrógeno</s0>
<s5>41</s5>
</fC03>
<fC03 i1="24" i2="X" l="FRE"><s0>Origine végétale</s0>
<s5>42</s5>
</fC03>
<fC03 i1="24" i2="X" l="ENG"><s0>Plant origin</s0>
<s5>42</s5>
</fC03>
<fC03 i1="24" i2="X" l="SPA"><s0>Origen vegetal</s0>
<s5>42</s5>
</fC03>
<fC03 i1="25" i2="X" l="FRE"><s0>Lignée MRC5</s0>
<s4>INC</s4>
<s5>62</s5>
</fC03>
<fC03 i1="26" i2="X" l="FRE"><s0>Lignée L6</s0>
<s4>INC</s4>
<s5>63</s5>
</fC03>
<fC03 i1="27" i2="X" l="FRE"><s0>Muntafara sessilifolia</s0>
<s4>INC</s4>
<s5>64</s5>
</fC03>
<fC03 i1="28" i2="X" l="FRE"><s0>Tabernaelegantinal</s0>
<s4>INC</s4>
<s5>65</s5>
</fC03>
<fC07 i1="01" i2="X" l="FRE"><s0>Rodentia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="01" i2="X" l="ENG"><s0>Rodentia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="01" i2="X" l="SPA"><s0>Rodentia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="02" i2="X" l="FRE"><s0>Mammalia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="02" i2="X" l="ENG"><s0>Mammalia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="02" i2="X" l="SPA"><s0>Mammalia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="03" i2="X" l="FRE"><s0>Vertebrata</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="03" i2="X" l="ENG"><s0>Vertebrata</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="03" i2="X" l="SPA"><s0>Vertebrata</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="04" i2="X" l="FRE"><s0>Apicomplexa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="04" i2="X" l="ENG"><s0>Apicomplexa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="04" i2="X" l="SPA"><s0>Apicomplexa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="05" i2="X" l="FRE"><s0>Protozoa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="05" i2="X" l="ENG"><s0>Protozoa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="05" i2="X" l="SPA"><s0>Protozoa</s0>
<s2>NS</s2>
</fC07>
<fN21><s1>247</s1>
</fN21>
</pA>
</standard>
</inist>
<affiliations><list><country><li>France</li>
<li>Madagascar</li>
</country>
<region><li>Île-de-France</li>
</region>
<settlement><li>Châtenay-Malabry</li>
<li>Paris</li>
</settlement>
<orgName><li>Université Paris-Sud</li>
</orgName>
</list>
<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>
</region>
<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="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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Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia

Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia

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