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Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae)

Identifieur interne : 000912 ( Main/Exploration ); précédent : 000911; suivant : 000913

Cytotoxic 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 Sarker

Source :

RBID : PMC:6930556

Abstract

A phytochemical study of the root and bark of Brucea antidysenterica J. F. Mill. (Simaroubaceae) afforded three new compounds, including a stilbene glycoside bruceanoside A (1), and two canthinone alkaloids bruceacanthinones A (3) and B (4), along with ten known secondary metabolites, rhaponticin (2), 1,11-dimethoxycanthin-6-one (5), canthin-6-one (6), 1-methoxycanthin-6-one (7), 2-methoxycanthin-6-one (8), 2-hydroxy-1,11-dimethoxycanthin-6-one (9), β-carboline-1-propionic acid (10), cleomiscosin C (11), cleomiscosin A (12), and hydnocarpin (13). 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 (313), 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.


Url:
DOI: 10.3390/molecules24234412
PubMed: 31816856
PubMed Central: 6930556


Affiliations:


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Le document en format XML

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<title xml:lang="en" level="a" type="main">Cytotoxic Stilbenes and Canthinone Alkaloids from
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<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>
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<email>dbjl19@yahoo.fr</email>
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<name sortKey="Mouthe Happi, Gervais" sort="Mouthe Happi, Gervais" uniqKey="Mouthe Happi G" first="Gervais" last="Mouthé Happi">Gervais Mouthé Happi</name>
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<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>
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<name sortKey="Wansi, Jean Duplex" sort="Wansi, Jean Duplex" uniqKey="Wansi J" first="Jean Duplex" last="Wansi">Jean Duplex Wansi</name>
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<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>
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<email>dbjl19@yahoo.fr</email>
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<nlm:aff id="af2-molecules-24-04412">Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany;
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</affiliation>
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<author>
<name sortKey="Nahar, Lutfun" sort="Nahar, Lutfun" uniqKey="Nahar L" first="Lutfun" last="Nahar">Lutfun Nahar</name>
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<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>
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<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>
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<name sortKey="Martin, Claire" sort="Martin, Claire" uniqKey="Martin C" first="Claire" last="Martin">Claire Martin</name>
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<email>c.martin@worc.ac.uk</email>
</nlm:aff>
</affiliation>
</author>
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<name sortKey="Sewald, Norbert" sort="Sewald, Norbert" uniqKey="Sewald N" first="Norbert" last="Sewald">Norbert Sewald</name>
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<nlm:aff id="af2-molecules-24-04412">Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, 33501 Bielefeld, Germany;
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<name sortKey="Sarker, Satyajit Dey" sort="Sarker, Satyajit Dey" uniqKey="Sarker S" first="Satyajit Dey" last="Sarker">Satyajit Dey Sarker</name>
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<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;
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<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>
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