Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae)
Identifieur interne : 000851 ( Pmc/Checkpoint ); précédent : 000850; suivant : 000852Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae)
Auteurs : Yves Salomon Makong ; Gervais Mouthé Happi ; Judith Liliane Djouaka Bavoua ; Jean Duplex Wansi ; Lutfun Nahar ; Alain François Kamdem Waffo ; Claire Martin ; Norbert Sewald ; Satyajit Dey SarkerSource :
- Molecules [ 1420-3049 ] ; 2019.
Abstract
A phytochemical study of the root and bark of
Url:
DOI: 10.3390/molecules24234412
PubMed: 31816856
PubMed Central: 6930556
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Cytotoxic Stilbenes and Canthinone Alkaloids from <italic>Brucea antidysenterica</italic> (Simaroubaceae)</title><author><name sortKey="Makong, Yves Salomon" sort="Makong, Yves Salomon" uniqKey="Makong Y" first="Yves Salomon" last="Makong">Yves Salomon Makong</name><affiliation><nlm:aff id="af1-molecules-24-04412">Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon;<email>y.makong@yahoo.com</email> (Y.S.M.);<email>dbjl19@yahoo.fr</email> (J.L.D.B.);<email>akamdemfr@yahoo.fr</email> (A.F.K.W.)</nlm:aff></affiliation></author><author><name sortKey="Mouthe Happi, Gervais" sort="Mouthe Happi, Gervais" uniqKey="Mouthe Happi G" first="Gervais" last="Mouthé Happi">Gervais Mouthé Happi</name><affiliation><nlm:aff id="af2-molecules-24-04412">Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany;<email>gervais20022003@yahoo.fr</email></nlm:aff></affiliation></author><author><name sortKey="Djouaka Bavoua, Judith Liliane" sort="Djouaka Bavoua, Judith Liliane" uniqKey="Djouaka Bavoua J" first="Judith Liliane" last="Djouaka Bavoua">Judith Liliane Djouaka Bavoua</name><affiliation><nlm:aff id="af1-molecules-24-04412">Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon;<email>y.makong@yahoo.com</email> (Y.S.M.);<email>dbjl19@yahoo.fr</email> (J.L.D.B.);<email>akamdemfr@yahoo.fr</email> (A.F.K.W.)</nlm:aff></affiliation></author><author><name sortKey="Wansi, Jean Duplex" sort="Wansi, Jean Duplex" uniqKey="Wansi J" first="Jean Duplex" last="Wansi">Jean Duplex Wansi</name><affiliation><nlm:aff id="af1-molecules-24-04412">Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon;<email>y.makong@yahoo.com</email> (Y.S.M.);<email>dbjl19@yahoo.fr</email> (J.L.D.B.);<email>akamdemfr@yahoo.fr</email> (A.F.K.W.)</nlm:aff></affiliation><affiliation><nlm:aff id="af2-molecules-24-04412">Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany;<email>gervais20022003@yahoo.fr</email></nlm:aff></affiliation></author><author><name sortKey="Nahar, Lutfun" sort="Nahar, Lutfun" uniqKey="Nahar L" first="Lutfun" last="Nahar">Lutfun Nahar</name><affiliation><nlm:aff id="af3-molecules-24-04412">Laboratory of Growth Regulators, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic;<email>L.Nahar@ljmu.ac.uk</email></nlm:aff></affiliation><affiliation><nlm:aff id="af4-molecules-24-04412">Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UK;<email>S.Sarker@ljmu.ac.uk</email></nlm:aff></affiliation></author><author><name sortKey="Kamdem Waffo, Alain Francois" sort="Kamdem Waffo, Alain Francois" uniqKey="Kamdem Waffo A" first="Alain François" last="Kamdem Waffo">Alain François Kamdem Waffo</name><affiliation><nlm:aff id="af1-molecules-24-04412">Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon;<email>y.makong@yahoo.com</email> (Y.S.M.);<email>dbjl19@yahoo.fr</email> (J.L.D.B.);<email>akamdemfr@yahoo.fr</email> (A.F.K.W.)</nlm:aff></affiliation></author><author><name sortKey="Martin, Claire" sort="Martin, Claire" uniqKey="Martin C" first="Claire" last="Martin">Claire Martin</name><affiliation><nlm:aff id="af5-molecules-24-04412">Department of Biological Sciences, School of Science and the Environment, University of Worcester, Henwick Grove, Worcester WR2 6AJ, UK;<email>c.martin@worc.ac.uk</email></nlm:aff></affiliation></author><author><name sortKey="Sewald, Norbert" sort="Sewald, Norbert" uniqKey="Sewald N" first="Norbert" last="Sewald">Norbert Sewald</name><affiliation><nlm:aff id="af2-molecules-24-04412">Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany;<email>gervais20022003@yahoo.fr</email></nlm:aff></affiliation></author><author><name sortKey="Sarker, Satyajit Dey" sort="Sarker, Satyajit Dey" uniqKey="Sarker S" first="Satyajit Dey" last="Sarker">Satyajit Dey Sarker</name><affiliation><nlm:aff id="af4-molecules-24-04412">Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UK;<email>S.Sarker@ljmu.ac.uk</email></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">31816856</idno><idno type="pmc">6930556</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6930556</idno><idno type="RBID">PMC:6930556</idno><idno type="doi">10.3390/molecules24234412</idno><date when="2019">2019</date><idno type="wicri:Area/Pmc/Corpus">000724</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000724</idno><idno type="wicri:Area/Pmc/Curation">000724</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000724</idno><idno type="wicri:Area/Pmc/Checkpoint">000851</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000851</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Cytotoxic Stilbenes and Canthinone Alkaloids from <italic>Brucea antidysenterica</italic> (Simaroubaceae)</title><author><name sortKey="Makong, Yves Salomon" sort="Makong, Yves Salomon" uniqKey="Makong Y" first="Yves Salomon" last="Makong">Yves Salomon Makong</name><affiliation><nlm:aff id="af1-molecules-24-04412">Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon;<email>y.makong@yahoo.com</email> (Y.S.M.);<email>dbjl19@yahoo.fr</email> (J.L.D.B.);<email>akamdemfr@yahoo.fr</email> (A.F.K.W.)</nlm:aff></affiliation></author><author><name sortKey="Mouthe Happi, Gervais" sort="Mouthe Happi, Gervais" uniqKey="Mouthe Happi G" first="Gervais" last="Mouthé Happi">Gervais Mouthé Happi</name><affiliation><nlm:aff id="af2-molecules-24-04412">Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany;<email>gervais20022003@yahoo.fr</email></nlm:aff></affiliation></author><author><name sortKey="Djouaka Bavoua, Judith Liliane" sort="Djouaka Bavoua, Judith Liliane" uniqKey="Djouaka Bavoua J" first="Judith Liliane" last="Djouaka Bavoua">Judith Liliane Djouaka Bavoua</name><affiliation><nlm:aff id="af1-molecules-24-04412">Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon;<email>y.makong@yahoo.com</email> (Y.S.M.);<email>dbjl19@yahoo.fr</email> (J.L.D.B.);<email>akamdemfr@yahoo.fr</email> (A.F.K.W.)</nlm:aff></affiliation></author><author><name sortKey="Wansi, Jean Duplex" sort="Wansi, Jean Duplex" uniqKey="Wansi J" first="Jean Duplex" last="Wansi">Jean Duplex Wansi</name><affiliation><nlm:aff id="af1-molecules-24-04412">Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon;<email>y.makong@yahoo.com</email> (Y.S.M.);<email>dbjl19@yahoo.fr</email> (J.L.D.B.);<email>akamdemfr@yahoo.fr</email> (A.F.K.W.)</nlm:aff></affiliation><affiliation><nlm:aff id="af2-molecules-24-04412">Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany;<email>gervais20022003@yahoo.fr</email></nlm:aff></affiliation></author><author><name sortKey="Nahar, Lutfun" sort="Nahar, Lutfun" uniqKey="Nahar L" first="Lutfun" last="Nahar">Lutfun Nahar</name><affiliation><nlm:aff id="af3-molecules-24-04412">Laboratory of Growth Regulators, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic;<email>L.Nahar@ljmu.ac.uk</email></nlm:aff></affiliation><affiliation><nlm:aff id="af4-molecules-24-04412">Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UK;<email>S.Sarker@ljmu.ac.uk</email></nlm:aff></affiliation></author><author><name sortKey="Kamdem Waffo, Alain Francois" sort="Kamdem Waffo, Alain Francois" uniqKey="Kamdem Waffo A" first="Alain François" last="Kamdem Waffo">Alain François Kamdem Waffo</name><affiliation><nlm:aff id="af1-molecules-24-04412">Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon;<email>y.makong@yahoo.com</email> (Y.S.M.);<email>dbjl19@yahoo.fr</email> (J.L.D.B.);<email>akamdemfr@yahoo.fr</email> (A.F.K.W.)</nlm:aff></affiliation></author><author><name sortKey="Martin, Claire" sort="Martin, Claire" uniqKey="Martin C" first="Claire" last="Martin">Claire Martin</name><affiliation><nlm:aff id="af5-molecules-24-04412">Department of Biological Sciences, School of Science and the Environment, University of Worcester, Henwick Grove, Worcester WR2 6AJ, UK;<email>c.martin@worc.ac.uk</email></nlm:aff></affiliation></author><author><name sortKey="Sewald, Norbert" sort="Sewald, Norbert" uniqKey="Sewald N" first="Norbert" last="Sewald">Norbert Sewald</name><affiliation><nlm:aff id="af2-molecules-24-04412">Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany;<email>gervais20022003@yahoo.fr</email></nlm:aff></affiliation></author><author><name sortKey="Sarker, Satyajit Dey" sort="Sarker, Satyajit Dey" uniqKey="Sarker S" first="Satyajit Dey" last="Sarker">Satyajit Dey Sarker</name><affiliation><nlm:aff id="af4-molecules-24-04412">Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UK;<email>S.Sarker@ljmu.ac.uk</email></nlm:aff></affiliation></author></analytic><series><title level="j">Molecules</title><idno type="eISSN">1420-3049</idno><imprint><date when="2019">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>A phytochemical study of the root and bark of <italic>Brucea antidysenterica</italic> J. F. Mill. (Simaroubaceae) afforded three new compounds, including a stilbene glycoside bruceanoside A (<bold>1</bold>), and two canthinone alkaloids bruceacanthinones A (<bold>3</bold>) and B (<bold>4</bold>), along with ten known secondary metabolites, rhaponticin (<bold>2</bold>), 1,11-dimethoxycanthin-6-one (<bold>5</bold>), canthin-6-one (<bold>6</bold>), 1-methoxycanthin-6-one (<bold>7</bold>), 2-methoxycanthin-6-one (<bold>8</bold>), 2-hydroxy-1,11-dimethoxycanthin-6-one (<bold>9</bold>), <italic>β</italic>-carboline-1-propionic acid (<bold>10</bold>), cleomiscosin C (<bold>11</bold>), cleomiscosin A (<bold>12</bold>), and hydnocarpin (<bold>13</bold>). The structures of all the compounds were determined using spectrometric and spectroscopic methods including 1D and 2D NMR, and HRSEIMS. The identities of the known compounds were further confirmed by comparison of their data with those reported in the literature. The root and bark methanolic extracts, the dichloromethane and ethyl acetate soluble fractions, and the isolated compounds (<bold>3</bold>–<bold>13</bold>), were assessed for their cytotoxicity against the cancer cell lines A-549, MCF-7, and PC-3. The results suggested that compounds in the extracts might possess a synergic action in their cytotoxicity.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Liu, J H" uniqKey="Liu J">J.-H. Liu</name></author><author><name sortKey="Jin, H Z" uniqKey="Jin H">H.-Z. Jin</name></author><author><name sortKey="Zhang, W D" uniqKey="Zhang W">W.-D. Zhang</name></author><author><name sortKey="Yan, S K" uniqKey="Yan S">S.-K. Yan</name></author><author><name sortKey="Shen, Y H" uniqKey="Shen Y">Y.-H. Shen</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wright, C W" uniqKey="Wright C">C.W. 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Molecules</journal-id><journal-id journal-id-type="iso-abbrev">Molecules</journal-id><journal-id journal-id-type="publisher-id">molecules</journal-id><journal-title-group><journal-title>Molecules</journal-title></journal-title-group><issn pub-type="epub">1420-3049</issn><publisher><publisher-name>MDPI</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">31816856</article-id><article-id pub-id-type="pmc">6930556</article-id><article-id pub-id-type="doi">10.3390/molecules24234412</article-id><article-id pub-id-type="publisher-id">molecules-24-04412</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Cytotoxic Stilbenes and Canthinone Alkaloids from <italic>Brucea antidysenterica</italic> (Simaroubaceae)</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Makong</surname><given-names>Yves Salomon</given-names></name><xref ref-type="aff" rid="af1-molecules-24-04412">1</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0001-9659-6125</contrib-id><name><surname>Mouthé Happi</surname><given-names>Gervais</given-names></name><xref ref-type="aff" rid="af2-molecules-24-04412">2</xref></contrib><contrib contrib-type="author"><name><surname>Djouaka Bavoua</surname><given-names>Judith Liliane</given-names></name><xref ref-type="aff" rid="af1-molecules-24-04412">1</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-5111-4361</contrib-id><name><surname>Wansi</surname><given-names>Jean Duplex</given-names></name><xref ref-type="aff" rid="af1-molecules-24-04412">1</xref><xref ref-type="aff" rid="af2-molecules-24-04412">2</xref><xref rid="c1-molecules-24-04412" ref-type="corresp">*</xref></contrib><contrib contrib-type="author"><name><surname>Nahar</surname><given-names>Lutfun</given-names></name><xref ref-type="aff" rid="af3-molecules-24-04412">3</xref><xref ref-type="aff" rid="af4-molecules-24-04412">4</xref></contrib><contrib contrib-type="author"><name><surname>Kamdem Waffo</surname><given-names>Alain François</given-names></name><xref ref-type="aff" rid="af1-molecules-24-04412">1</xref></contrib><contrib contrib-type="author"><name><surname>Martin</surname><given-names>Claire</given-names></name><xref ref-type="aff" rid="af5-molecules-24-04412">5</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-0309-2655</contrib-id><name><surname>Sewald</surname><given-names>Norbert</given-names></name><xref ref-type="aff" rid="af2-molecules-24-04412">2</xref><xref rid="c1-molecules-24-04412" ref-type="corresp">*</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0003-4038-0514</contrib-id><name><surname>Sarker</surname><given-names>Satyajit Dey</given-names></name><xref ref-type="aff" rid="af4-molecules-24-04412">4</xref></contrib></contrib-group><aff id="af1-molecules-24-04412"><label>1</label>Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157 Douala, Cameroon;<email>y.makong@yahoo.com</email> (Y.S.M.);<email>dbjl19@yahoo.fr</email> (J.L.D.B.);<email>akamdemfr@yahoo.fr</email> (A.F.K.W.)</aff><aff id="af2-molecules-24-04412"><label>2</label>Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany;<email>gervais20022003@yahoo.fr</email></aff><aff id="af3-molecules-24-04412"><label>3</label>Laboratory of Growth Regulators, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic;<email>L.Nahar@ljmu.ac.uk</email></aff><aff id="af4-molecules-24-04412"><label>4</label>Centre for Natural Products Discovery (CNPD), School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UK;<email>S.Sarker@ljmu.ac.uk</email></aff><aff id="af5-molecules-24-04412"><label>5</label>Department of Biological Sciences, School of Science and the Environment, University of Worcester, Henwick Grove, Worcester WR2 6AJ, UK;<email>c.martin@worc.ac.uk</email></aff><author-notes><corresp id="c1-molecules-24-04412"><label>*</label>Correspondence: <email>jean.wansi@uni-bielefeld.de</email> or <email>jdwansi@yahoo.fr</email> (J.D.W.); <email>norbert.sewald@uni-bielefeld.de</email> (N.S.); Tel.: +49-1521-690-4218 (J.D.W.)</corresp></author-notes><pub-date pub-type="epub"><day>03</day><month>12</month><year>2019</year></pub-date><pub-date pub-type="collection"><month>12</month><year>2019</year></pub-date><volume>24</volume><issue>23</issue><elocation-id>4412</elocation-id><history><date date-type="received"><day>21</day><month>11</month><year>2019</year></date><date date-type="accepted"><day>29</day><month>11</month><year>2019</year></date></history><permissions><copyright-statement>© 2019 by the authors.</copyright-statement><copyright-year>2019</copyright-year><license license-type="open-access"><license-p>Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">http://creativecommons.org/licenses/by/4.0/</ext-link>).</license-p></license></permissions><abstract><p>A phytochemical study of the root and bark of <italic>Brucea antidysenterica</italic> J. F. Mill. (Simaroubaceae) afforded three new compounds, including a stilbene glycoside bruceanoside A (<bold>1</bold>), and two canthinone alkaloids bruceacanthinones A (<bold>3</bold>) and B (<bold>4</bold>), along with ten known secondary metabolites, rhaponticin (<bold>2</bold>), 1,11-dimethoxycanthin-6-one (<bold>5</bold>), canthin-6-one (<bold>6</bold>), 1-methoxycanthin-6-one (<bold>7</bold>), 2-methoxycanthin-6-one (<bold>8</bold>), 2-hydroxy-1,11-dimethoxycanthin-6-one (<bold>9</bold>), <italic>β</italic>-carboline-1-propionic acid (<bold>10</bold>), cleomiscosin C (<bold>11</bold>), cleomiscosin A (<bold>12</bold>), and hydnocarpin (<bold>13</bold>). The structures of all the compounds were determined using spectrometric and spectroscopic methods including 1D and 2D NMR, and HRSEIMS. The identities of the known compounds were further confirmed by comparison of their data with those reported in the literature. The root and bark methanolic extracts, the dichloromethane and ethyl acetate soluble fractions, and the isolated compounds (<bold>3</bold>–<bold>13</bold>), were assessed for their cytotoxicity against the cancer cell lines A-549, MCF-7, and PC-3. The results suggested that compounds in the extracts might possess a synergic action in their cytotoxicity.</p></abstract><kwd-group><kwd><italic>Brucea antidysenterica</italic></kwd><kwd>Simaroubaceae</kwd><kwd>bruceanoside A</kwd><kwd>bruceacanthinones A–B</kwd><kwd>cytotoxicity</kwd></kwd-group></article-meta></front><floats-group><fig id="molecules-24-04412-f001" orientation="portrait" position="float"><label>Figure 1</label><caption><p>Structures of compounds (<bold>1</bold>–<bold>13</bold>) isolated from <italic>Brucea antidysenterica</italic>.</p></caption><graphic xlink:href="molecules-24-04412-g001"></graphic></fig><fig id="molecules-24-04412-f002" orientation="portrait" position="float"><label>Figure 2</label><caption><p>Select, key HMBC correlations of <bold>1</bold>.</p></caption><graphic xlink:href="molecules-24-04412-g002"></graphic></fig><fig id="molecules-24-04412-f003" orientation="portrait" position="float"><label>Figure 3</label><caption><p>Select, key COSY (blue) and HMBC (red) correlations of <bold>3</bold> and <bold>4</bold>.</p></caption><graphic xlink:href="molecules-24-04412-g003"></graphic></fig><table-wrap id="molecules-24-04412-t001" orientation="portrait" position="float"><object-id pub-id-type="pii">molecules-24-04412-t001_Table 1</object-id><label>Table 1</label><caption><p><sup>1</sup>H (600 MHz) and <sup>13</sup>C (150 MHz) NMR assignments of <bold>1</bold> in DMSO-<italic>d<sub>6</sub></italic>.</p></caption><table frame="hsides" rules="groups"><thead><tr><th rowspan="2" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" colspan="1">No</th><th colspan="2" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1">1</th></tr><tr><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>δ</italic><sub>C</sub></th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>δ</italic><sub>H</sub> (mult., <italic>J</italic> in Hz)</th></tr></thead><tbody><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold><italic>α</italic></bold></td><td align="center" valign="middle" rowspan="1" colspan="1">126.4</td><td align="center" valign="middle" rowspan="1" colspan="1">6.99 (1H, d, 16.4)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold><italic>β</italic></bold></td><td align="center" valign="middle" rowspan="1" colspan="1">129.1</td><td align="center" valign="middle" rowspan="1" colspan="1">7.20 (1H, d, 16.4)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>1</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">129.9</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>2</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">105.6</td><td align="center" valign="middle" rowspan="1" colspan="1">6.82 (1H, brs)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>3</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">159.3</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>4</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">101.9</td><td align="center" valign="middle" rowspan="1" colspan="1">6.52 (1H, t, 2.2)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>5</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">160.2</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>6</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">107.6</td><td align="center" valign="middle" rowspan="1" colspan="1">6.78 (1H, brs)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>1′</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">139.7</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>2′/6′</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">128.4</td><td align="center" valign="middle" rowspan="1" colspan="1">7.58 (2H, d, 8.8)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>3′/5′</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">114.6</td><td align="center" valign="middle" rowspan="1" colspan="1">6.95 (2H, d, 8.8)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>4′</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">159.8</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>OCH<sub>3</sub>-3/5</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">55.6</td><td align="center" valign="middle" rowspan="1" colspan="1">3.80 (6H, s)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">sugar moieties</td><td align="center" valign="middle" rowspan="1" colspan="1"></td><td align="center" valign="middle" rowspan="1" colspan="1"></td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>glc-1</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">101.0</td><td align="center" valign="middle" rowspan="1" colspan="1">4.89 (1H, d, 7.6)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>2</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">73.7</td><td align="center" valign="middle" rowspan="1" colspan="1">3.19 (1H, m)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>3</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">75.8</td><td align="center" valign="middle" rowspan="1" colspan="1">3.52 (1H. m)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>4</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">70.8</td><td align="center" valign="middle" rowspan="1" colspan="1">3.65 (1H, m)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>5</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">76.9</td><td align="center" valign="middle" rowspan="1" colspan="1">3.30 (1H, m)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>6</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">66.8</td><td align="center" valign="middle" rowspan="1" colspan="1">3.41 (1H, m)<break></break>3.87 (1H, m)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>rha-1</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">101.0</td><td align="center" valign="middle" rowspan="1" colspan="1">4.56 (1H, d, 1.6)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>2</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">71.2</td><td align="center" valign="middle" rowspan="1" colspan="1">3.42 (1H, m)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>3</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">70.3</td><td align="center" valign="middle" rowspan="1" colspan="1">3.46 (1H, m)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>4</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">72.5</td><td align="center" valign="middle" rowspan="1" colspan="1">3.18 (1H, m)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>5</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">68.8</td><td align="center" valign="middle" rowspan="1" colspan="1">3.43 (1H, m)</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>6</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">18.3</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">1.11 (3H, d, 6.1)</td></tr></tbody></table></table-wrap><table-wrap id="molecules-24-04412-t002" orientation="portrait" position="float"><object-id pub-id-type="pii">molecules-24-04412-t002_Table 2</object-id><label>Table 2</label><caption><p><sup>1</sup>H (600 MHz) and <sup>13</sup>C (150 MHz) NMR assignments of <bold>3</bold> and <bold>4</bold> in DMSO-<italic>d<sub>6</sub></italic>.</p></caption><table frame="hsides" rules="groups"><thead><tr><th rowspan="2" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" colspan="1">No</th><th colspan="2" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1">3</th><th colspan="2" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1">4</th></tr><tr><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>δ</italic><sub>C</sub></th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>δ</italic><sub>H</sub> (mult., <italic>J</italic> in Hz)</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>δ</italic><sub>C</sub></th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><italic>δ</italic><sub>H</sub> (mult., <italic>J</italic> in Hz)</th></tr></thead><tbody><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>1</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">140.0</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td><td align="center" valign="middle" rowspan="1" colspan="1">140.4</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>2</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">152.6</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td><td align="center" valign="middle" rowspan="1" colspan="1">151.5</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>4</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">139.0</td><td align="center" valign="middle" rowspan="1" colspan="1">8.08 (1H, d, 9.7)</td><td align="center" valign="middle" rowspan="1" colspan="1">139.9</td><td align="center" valign="middle" rowspan="1" colspan="1">8.04 (1H, d, 9.8)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>5</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">127.3</td><td align="center" valign="middle" rowspan="1" colspan="1">6.90 (1H, d, 9.7)</td><td align="center" valign="middle" rowspan="1" colspan="1">125.9</td><td align="center" valign="middle" rowspan="1" colspan="1">6.90 (1H, d, 9.8)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>6</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">159.6</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td><td align="center" valign="middle" rowspan="1" colspan="1">160.0</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>8</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">117.1</td><td align="center" valign="middle" rowspan="1" colspan="1">8.70 (1H, dd, 1.2, 7.8)</td><td align="center" valign="middle" rowspan="1" colspan="1">112.9</td><td align="center" valign="middle" rowspan="1" colspan="1">8.40 (1H, dd, 0.8, 8.2)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>9</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">130.7</td><td align="center" valign="middle" rowspan="1" colspan="1">7.70 (1H, td, 1.0, 7.6, 7.8)</td><td align="center" valign="middle" rowspan="1" colspan="1">132.3</td><td align="center" valign="middle" rowspan="1" colspan="1">7.65 (1H, t, 8.2)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>10</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">127.5</td><td align="center" valign="middle" rowspan="1" colspan="1">7.58 (1H, td, 1.2, 7.6, 7.8)</td><td align="center" valign="middle" rowspan="1" colspan="1">108.0</td><td align="center" valign="middle" rowspan="1" colspan="1">7.01 (1H, dd, 0.8, 8.2)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>11</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">125.0</td><td align="center" valign="middle" rowspan="1" colspan="1">8.26 (1H, dd, 1.0, 7.6)</td><td align="center" valign="middle" rowspan="1" colspan="1">156.1</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>12</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">123.1</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td><td align="center" valign="middle" rowspan="1" colspan="1">126.8</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>13</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">136.4</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td><td align="center" valign="middle" rowspan="1" colspan="1">139.9</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>14</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">130.7</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td><td align="center" valign="middle" rowspan="1" colspan="1">132.9</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>15</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">128.7</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td><td align="center" valign="middle" rowspan="1" colspan="1">132.3</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>16</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">126.1</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td><td align="center" valign="middle" rowspan="1" colspan="1">126.8</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>OMe-2</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">57.2</td><td align="center" valign="middle" rowspan="1" colspan="1">4.29 (3H, s)</td><td align="center" valign="middle" rowspan="1" colspan="1">56.3</td><td align="center" valign="middle" rowspan="1" colspan="1">4.09 (3H, s)</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>OMe-11</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">–</td><td align="center" valign="middle" rowspan="1" colspan="1">–</td><td align="center" valign="middle" rowspan="1" colspan="1">57.8</td><td align="center" valign="middle" rowspan="1" colspan="1">4.28 (3H, s)</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>OH-1</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">–</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">8.52 (1H, s)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">–</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">8.50 (1H, s)</td></tr></tbody></table></table-wrap><table-wrap id="molecules-24-04412-t003" orientation="portrait" position="float"><object-id pub-id-type="pii">molecules-24-04412-t003_Table 3</object-id><label>Table 3</label><caption><p>Cytotoxicity of extracts, fractions, and isolated compounds from <italic>Brucea antidysenterica.</italic></p></caption><table frame="hsides" rules="groups"><thead><tr><th rowspan="2" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" colspan="1">Samples</th><th colspan="3" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1">IC<sub>50</sub> in μg/mL</th></tr><tr><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">A-549</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">MCF-7</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">PC-3</th></tr></thead><tbody><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>Root extract</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">75.2 ± 3.2</td><td align="center" valign="middle" rowspan="1" colspan="1">80.5 ± 1.8</td><td align="center" valign="middle" rowspan="1" colspan="1">77.7 ± 2.5</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>Bark extract</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">65.1 ± 1.5</td><td align="center" valign="middle" rowspan="1" colspan="1">72.3 ± 3.5</td><td align="center" valign="middle" rowspan="1" colspan="1">70.2 ± 4.2</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>DCM</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">50.0 ± 5.2</td><td align="center" valign="middle" rowspan="1" colspan="1">55.1 ± 4.2</td><td align="center" valign="middle" rowspan="1" colspan="1">57.0 ± 5.3</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>EA</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">61.5 ± 3.2</td><td align="center" valign="middle" rowspan="1" colspan="1">58.1 ± 1.9</td><td align="center" valign="middle" rowspan="1" colspan="1">55.8 ± 2.4</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>3</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td><td align="center" valign="middle" rowspan="1" colspan="1">195.5 ± 9.5</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>4</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">150.3 ± 8.5</td><td align="center" valign="middle" rowspan="1" colspan="1">157.5 ± 7.5</td><td align="center" valign="middle" rowspan="1" colspan="1">160.5 ± 5.5</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>5</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>6</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">175.6 ± 6.1</td><td align="center" valign="middle" rowspan="1" colspan="1">170.3 ± 5.8</td><td align="center" valign="middle" rowspan="1" colspan="1">177.3 ± 5.9</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>7</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">125.8 ± 7.2</td><td align="center" valign="middle" rowspan="1" colspan="1">152.1 ± 11.2</td><td align="center" valign="middle" rowspan="1" colspan="1">155.1 ± 5.3</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>8</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">121.5 ± 8.2</td><td align="center" valign="middle" rowspan="1" colspan="1">126.2 ± 5.5</td><td align="center" valign="middle" rowspan="1" colspan="1">130.9 ± 7.4</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>9</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">138.1 ± 9.7</td><td align="center" valign="middle" rowspan="1" colspan="1">145.2 ± 9.9</td><td align="center" valign="middle" rowspan="1" colspan="1">151.5 ± 8.3</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>10</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>11</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>12</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">130.8 ± 7.4</td><td align="center" valign="middle" rowspan="1" colspan="1">132.1 ± 11.2</td><td align="center" valign="middle" rowspan="1" colspan="1">130.1 ± 5.3</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>13</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td><td align="center" valign="middle" rowspan="1" colspan="1">>250</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>Etoposide</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">3.5 ± 0.5</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">10.2 ± 1.2</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">7.9 ± 1.1</td></tr></tbody></table></table-wrap></floats-group></pmc><affiliations><list></list><tree><noCountry><name sortKey="Djouaka Bavoua, Judith Liliane" sort="Djouaka Bavoua, Judith Liliane" uniqKey="Djouaka Bavoua J" first="Judith Liliane" last="Djouaka Bavoua">Judith Liliane Djouaka Bavoua</name><name sortKey="Kamdem Waffo, Alain Francois" sort="Kamdem Waffo, Alain Francois" uniqKey="Kamdem Waffo A" first="Alain François" last="Kamdem Waffo">Alain François Kamdem Waffo</name><name sortKey="Makong, Yves Salomon" sort="Makong, Yves Salomon" uniqKey="Makong Y" first="Yves Salomon" last="Makong">Yves Salomon Makong</name><name sortKey="Martin, Claire" sort="Martin, Claire" uniqKey="Martin C" first="Claire" last="Martin">Claire Martin</name><name sortKey="Mouthe Happi, Gervais" sort="Mouthe Happi, Gervais" uniqKey="Mouthe Happi G" first="Gervais" last="Mouthé Happi">Gervais Mouthé Happi</name><name sortKey="Nahar, Lutfun" sort="Nahar, Lutfun" uniqKey="Nahar L" first="Lutfun" last="Nahar">Lutfun Nahar</name><name sortKey="Sarker, Satyajit Dey" sort="Sarker, Satyajit Dey" uniqKey="Sarker S" first="Satyajit Dey" last="Sarker">Satyajit Dey Sarker</name><name sortKey="Sewald, Norbert" sort="Sewald, Norbert" uniqKey="Sewald N" first="Norbert" last="Sewald">Norbert Sewald</name><name sortKey="Wansi, Jean Duplex" sort="Wansi, Jean Duplex" uniqKey="Wansi J" first="Jean Duplex" last="Wansi">Jean Duplex Wansi</name></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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