Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia
Identifieur interne : 001080 ( Istex/Corpus ); précédent : 001079; suivant : 001081Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia
Auteurs : Marion Girardot ; Alice Gadea ; Christiane Deregnaucourt ; Alexandre Deville ; Lionel Dubost ; Bastien Nay ; Alexandre Maciuk ; Philippe Rasoanaivo ; Lengo MambuSource :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2012-05.
English descriptors
- 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
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ISTEX:CA0F92C383C023AD53B4B1F06AA8DED1F2FCC0E9Le document en format XML
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Clément, 92296 Châtenay‐Malabry, France</mods:affiliation></affiliation></author><author><name sortKey="Rasoanaivo, Philippe" sort="Rasoanaivo, Philippe" uniqKey="Rasoanaivo P" first="Philippe" last="Rasoanaivo">Philippe Rasoanaivo</name><affiliation><mods:affiliation>Institut Malgache de Recherches Appliquées, BP 3833, 101 Antananarivo, Madagascar</mods:affiliation></affiliation></author><author><name sortKey="Mambu, Lengo" sort="Mambu, Lengo" uniqKey="Mambu L" first="Lengo" last="Mambu">Lengo Mambu</name><affiliation><mods:affiliation>Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro‐organismes, UMR 7245 CNRS‐MNHN, 57 rue Cuvier (CP 54), 75005 Paris, France, Fax: +33‐1‐40‐79‐31‐35</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: mambu@mnhn.fr</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">European Journal of Organic Chemistry</title><title level="j" type="alt">EUROPEAN JOURNAL OF ORGANIC CHEMISTRY</title><idno type="ISSN">1434-193X</idno><idno type="eISSN">1099-0690</idno><imprint><biblScope unit="vol">2012</biblScope><biblScope unit="issue">14</biblScope><biblScope unit="page" from="2816">2816</biblScope><biblScope unit="page" to="2823">2823</biblScope><biblScope unit="page-count">8</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2012-05">2012-05</date></imprint><idno type="ISSN">1434-193X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1434-193X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="Teeft" xml:lang="en"><term>Aldehyde</term><term>Aldehyde group</term><term>Aldehyde proton</term><term>Alkaloid</term><term>Alkaloidal crude</term><term>Amorphous powder</term><term>Antiplasmodial</term><term>Baerheim svendsen</term><term>Bisindole</term><term>Bisindole alkaloids</term><term>Chem</term><term>Chemical shifts</term><term>Cosy spectrum</term><term>Cytotoxic</term><term>Cytotoxic activities</term><term>Ethyl chain</term><term>Falciparum</term><term>Flow rate</term><term>Full paper</term><term>Gmbh</term><term>Hmbc</term><term>Hrms</term><term>Hrms spectrum</term><term>Hsqc spectrum</term><term>Iboga</term><term>Iboga moieties</term><term>Iboga moiety</term><term>Indole</term><term>Kgaa</term><term>Mammalian cells</term><term>Meoh</term><term>Moiety</term><term>Molecular formula</term><term>Muntafara</term><term>Muntafara sessilifolia</term><term>Noesy</term><term>Plasmodium falciparum</term><term>Proton</term><term>Sessilifolia</term><term>Spectroscopic</term><term>Spectroscopic data</term><term>Verlag</term><term>Verlag gmbh</term><term>Vobasinyl</term><term>Vobasinyl moiety</term><term>Weinheim</term></keywords></textClass></profileDesc></teiHeader><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 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. 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Clément, 92296 Châtenay‐Malabry, France</json:string></affiliations></json:item><json:item><name>Philippe Rasoanaivo</name><affiliations><json:string>Institut Malgache de Recherches Appliquées, BP 3833, 101 Antananarivo, Madagascar</json:string></affiliations></json:item><json:item><name>Lengo Mambu</name><affiliations><json:string>Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro‐organismes, UMR 7245 CNRS‐MNHN, 57 rue Cuvier (CP 54), 75005 Paris, France, Fax: +33‐1‐40‐79‐31‐35</json:string><json:string>E-mail: mambu@mnhn.fr</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>Natural products</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Alkaloids</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Structure elucidation</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Biological activity</value></json:item></subject><articleId><json:string>EJOC201101738</json:string></articleId><arkIstex>ark:/67375/WNG-X21M2NBG-7</arkIstex><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><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.</abstract><qualityIndicators><score>8.476</score><pdfWordCount>5406</pdfWordCount><pdfCharCount>32598</pdfCharCount><pdfVersion>1.3</pdfVersion><pdfPageCount>8</pdfPageCount><pdfPageSize>594.92 x 793.94 pts</pdfPageSize><pdfWordsPerPage>676</pdfWordsPerPage><pdfText>true</pdfText><refBibsNative>true</refBibsNative><abstractWordCount>123</abstractWordCount><abstractCharCount>883</abstractCharCount><keywordCount>4</keywordCount></qualityIndicators><title>Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia</title><genre><json:string>article</json:string></genre><host><title>European Journal of Organic Chemistry</title><language><json:string>unknown</json:string></language><doi><json:string>10.1002/(ISSN)1099-0690</json:string></doi><issn><json:string>1434-193X</json:string></issn><eissn><json:string>1099-0690</json:string></eissn><publisherId><json:string>EJOC</json:string></publisherId><volume>2012</volume><issue>14</issue><pages><first>2816</first><last>2823</last><total>8</total></pages><genre><json:string>journal</json:string></genre><subject><json:item><value>Full Paper</value></json:item><json:item><value>Full Papers</value></json:item><json:item><value>Indole Alkaloids</value></json:item></subject></host><namedEntities><unitex><date><json:string>5000</json:string><json:string>2012</json:string><json:string>3-2-3</json:string><json:string>3-1-5</json:string><json:string>8400S</json:string><json:string>3-1-6</json:string><json:string>1200</json:string><json:string>19S</json:string></date><geogName></geogName><orgName><json:string>Madagascar Supporting</json:string><json:string>Department of Botany, Parc Botanique</json:string></orgName><orgName_funder></orgName_funder><orgName_provider></orgName_provider><persName><json:string>M. 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Debray</json:string><json:string>S. Yang</json:string><json:string>A. Baerheim</json:string><json:string>H. S. Pang</json:string><json:string>G. N. Zirihi</json:string><json:string>R. Razafindrambao</json:string><json:string>S. P. Gunasekera</json:string><json:string>M. Bui</json:string><json:string>B. Gabetta</json:string><json:string>J. D. Chulay</json:string><json:string>A. Ahond</json:string><json:string>P. Potier</json:string><json:string>R. Van der Heijden</json:string><json:string>B. Compound</json:string><json:string>K. Komiyama</json:string><json:string>J. Chem</json:string><json:string>Y. M. Choo</json:string><json:string>W. Trager</json:string><json:string>E. M. Martinelli</json:string><json:string>B. Richard</json:string><json:string>N. Aimi</json:string><json:string>L. Le Men-Olivier</json:string><json:string>N. J. Cone</json:string><json:string>B. Bodo</json:string><json:string>F. Guédé-Guina</json:string><json:string>Philippe Rasoanaivo</json:string><json:string>H. 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KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2011-12-02"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:3.1.3 standalone mode:FullText mathml2tex" date="2012-05-02"></event><event type="publishedOnlineEarlyUnpaginated" date="2012-04-10"></event><event type="firstOnline" date="2012-04-10"></event><event type="publishedOnlineFinalForm" date="2012-05-02"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-24"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.3.4 mode:FullText" date="2015-02-24"></event></eventGroup><numberingGroup><numbering type="pageFirst">2816</numbering><numbering type="pageLast">2823</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:EJOC.EJOC201101738.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="3"></count><count type="tableTotal" number="3"></count><count type="referenceTotal" number="21"></count></countGroup><titleGroup><title type="main" xml:lang="en">Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from <i>Muntafara sessilifolia</i></title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Marion</givenNames><familyName>Girardot</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Alice</givenNames><familyName>Gadea</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Christiane</givenNames><familyName>Deregnaucourt</familyName></personName></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Alexandre</givenNames><familyName>Deville</familyName></personName></creator><creator xml:id="au5" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Lionel</givenNames><familyName>Dubost</familyName></personName></creator><creator xml:id="au6" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Bastien</givenNames><familyName>Nay</familyName></personName></creator><creator xml:id="au7" creatorRole="author" affiliationRef="#af2"><personName><givenNames>Alexandre</givenNames><familyName>Maciuk</familyName></personName></creator><creator xml:id="au8" creatorRole="author" affiliationRef="#af3"><personName><givenNames>Philippe</givenNames><familyName>Rasoanaivo</familyName></personName></creator><creator xml:id="au9" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Lengo</givenNames><familyName>Mambu</familyName></personName><contactDetails><email>mambu@mnhn.fr</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="FR" type="organization"><unparsedAffiliation>Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro‐organismes, UMR 7245 CNRS‐MNHN, 57 rue Cuvier (CP 54), 75005 Paris, France, Fax: +33‐1‐40‐79‐31‐35</unparsedAffiliation></affiliation><affiliation xml:id="af2" countryCode="FR" type="organization"><unparsedAffiliation>Université Paris‐Sud, Faculté de Pharmacie, UMR 8076 CNRS (BioCIS) Laboratoire de Pharmacognosie, 5 rue J.‐B. Clément, 92296 Châtenay‐Malabry, France</unparsedAffiliation></affiliation><affiliation xml:id="af3" countryCode="MG" type="organization"><unparsedAffiliation>Institut Malgache de Recherches Appliquées, BP 3833, 101 Antananarivo, Madagascar</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">Natural products</keyword><keyword xml:id="kwd2">Alkaloids</keyword><keyword xml:id="kwd3">Structure elucidation</keyword><keyword xml:id="kwd4">Biological activity</keyword></keywordGroup><fundingInfo><fundingAgency>French Ministère de la Recherche</fundingAgency></fundingInfo><supportingInformation><p>Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer‐reviewed, but not copy‐edited or typeset. They are made available as submitted by the authors.
</p><supportingInfoItem><mediaResource alt="supporting information" href="urn-x:wiley:1434193X:media:ejoc201101738:ejoc_201101738_sm_miscellaneous_information"></mediaResource><caption>miscellaneous_information</caption></supportingInfoItem></supportingInformation><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>Bioassay‐guided fractionation of the stem bark of <i>Muntafara sessilifolia</i> has led to the isolation of six new vobasinyl‐iboga bisindole alkaloids, tabernaelegantinals A, B and E, and (3′<i>R</i>)‐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 <i>Plasmodium falciparum</i> (5.3 μ<sc>M</sc> 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.</p></abstract><abstract type="graphical" xml:lang="en"><p>Six new vobasinyl‐iboga bisindole alkaloids and eight known compounds have been isolated from the stem bark of<i>Muntafara sessilifolia</i>. 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.
<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY-VCH" href="urn:x-wiley:1434193X:media:EJOC201101738:fig000"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Tabernaelegantinals: Unprecedented Cytotoxic Bisindole Alkaloids from Muntafara sessilifolia</title></titleInfo><name type="personal"><namePart type="given">Marion</namePart><namePart type="family">Girardot</namePart><affiliation>Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro‐organismes, UMR 7245 CNRS‐MNHN, 57 rue Cuvier (CP 54), 75005 Paris, France, Fax: +33‐1‐40‐79‐31‐35</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Alice</namePart><namePart type="family">Gadea</namePart><affiliation>Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro‐organismes, UMR 7245 CNRS‐MNHN, 57 rue Cuvier (CP 54), 75005 Paris, France, Fax: +33‐1‐40‐79‐31‐35</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Christiane</namePart><namePart type="family">Deregnaucourt</namePart><affiliation>Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro‐organismes, UMR 7245 CNRS‐MNHN, 57 rue Cuvier (CP 54), 75005 Paris, France, Fax: +33‐1‐40‐79‐31‐35</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Alexandre</namePart><namePart type="family">Deville</namePart><affiliation>Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro‐organismes, UMR 7245 CNRS‐MNHN, 57 rue Cuvier (CP 54), 75005 Paris, France, Fax: +33‐1‐40‐79‐31‐35</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Lionel</namePart><namePart type="family">Dubost</namePart><affiliation>Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro‐organismes, UMR 7245 CNRS‐MNHN, 57 rue Cuvier (CP 54), 75005 Paris, France, Fax: +33‐1‐40‐79‐31‐35</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Bastien</namePart><namePart type="family">Nay</namePart><affiliation>Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro‐organismes, UMR 7245 CNRS‐MNHN, 57 rue Cuvier (CP 54), 75005 Paris, France, Fax: +33‐1‐40‐79‐31‐35</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Alexandre</namePart><namePart type="family">Maciuk</namePart><affiliation>Université Paris‐Sud, Faculté de Pharmacie, UMR 8076 CNRS (BioCIS) Laboratoire de Pharmacognosie, 5 rue J.‐B. Clément, 92296 Châtenay‐Malabry, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Philippe</namePart><namePart type="family">Rasoanaivo</namePart><affiliation>Institut Malgache de Recherches Appliquées, BP 3833, 101 Antananarivo, Madagascar</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Lengo</namePart><namePart type="family">Mambu</namePart><affiliation>Muséum National d'Histoire Naturelle, Molécules de Communication et Adaptation des Micro‐organismes, UMR 7245 CNRS‐MNHN, 57 rue Cuvier (CP 54), 75005 Paris, France, Fax: +33‐1‐40‐79‐31‐35</affiliation><affiliation>E-mail: mambu@mnhn.fr</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2012-05</dateIssued><dateCaptured encoding="w3cdtf">2011-12-02</dateCaptured><copyrightDate encoding="w3cdtf">2012</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">3</extent><extent unit="tables">3</extent><extent unit="references">21</extent></physicalDescription><abstract 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 IC50) over mammalian cell lines (selectivity index > 45). The tabernaelegantinals share an unprecedented α‐amino aldehyde moiety, the biosynthetic origin of which is discussed.</abstract><abstract type="graphical" 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.</abstract><note type="funding">French Ministère de la Recherche</note><subject lang="en"><genre>keywords</genre><topic>Natural products</topic><topic>Alkaloids</topic><topic>Structure elucidation</topic><topic>Biological activity</topic></subject><relatedItem type="host"><titleInfo><title>European Journal of Organic Chemistry</title></titleInfo><titleInfo type="abbreviated"><title>Eur. J. Org. Chem.</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><note type="content"> Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer‐reviewed, but not copy‐edited or typeset. 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