Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies
Identifieur interne : 000947 ( Pmc/Curation ); précédent : 000946; suivant : 000948Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies
Auteurs : Philip F. Uzor [Nigeria]Source :
- Evidence-based Complementary and Alternative Medicine : eCAM [ 1741-427X ] ; 2020.
Abstract
Malaria is one of the major health problems in developing countries. The disease kills a large number of people every year and also affects financial status of many countries. Resistance of the plasmodium parasite, the causative agent, to the existing drugs, including chloroquine, mefloquine, and artemisinin based combination therapy (ACT), is a serious global issue in malaria treatment and control. This warrants an urgent quest for novel compounds, particularly from natural sources such as medicinal plants. Alkaloids have over the years been recognized as important phytoconstituents with interesting biological properties. In fact, the first successful antimalarial drug was quinine, an alkaloid, which was extracted from Cinchona tree. In the present review work, the alkaloids isolated and reported recently (2013 till 2019) to possess antimalarial activity are presented. Several classes of alkaloids, including terpenoidal, indole, bisindole, quinolone, and isoquinoline alkaloids, were identified with a promising antimalarial activity. It is hoped that the reports of the review work will spur further research into the structural modification and/or development of the interesting compounds as novel antimalarial drugs.
Url:
DOI: 10.1155/2020/8749083
PubMed: 32104196
PubMed Central: 7037883
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies</title><author><name sortKey="Uzor, Philip F" sort="Uzor, Philip F" uniqKey="Uzor P" first="Philip F." last="Uzor">Philip F. Uzor</name><affiliation wicri:level="1"><nlm:aff id="I1">Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, 410001 Nsukka, Enugu State, Nigeria</nlm:aff><country xml:lang="fr">Nigeria</country><wicri:regionArea>Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, 410001 Nsukka, Enugu State</wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">32104196</idno><idno type="pmc">7037883</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7037883</idno><idno type="RBID">PMC:7037883</idno><idno type="doi">10.1155/2020/8749083</idno><date when="2020">2020</date><idno type="wicri:Area/Pmc/Corpus">000947</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000947</idno><idno type="wicri:Area/Pmc/Curation">000947</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000947</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies</title><author><name sortKey="Uzor, Philip F" sort="Uzor, Philip F" uniqKey="Uzor P" first="Philip F." last="Uzor">Philip F. Uzor</name><affiliation wicri:level="1"><nlm:aff id="I1">Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, 410001 Nsukka, Enugu State, Nigeria</nlm:aff><country xml:lang="fr">Nigeria</country><wicri:regionArea>Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, 410001 Nsukka, Enugu State</wicri:regionArea></affiliation></author></analytic><series><title level="j">Evidence-based Complementary and Alternative Medicine : eCAM</title><idno type="ISSN">1741-427X</idno><idno type="eISSN">1741-4288</idno><imprint><date when="2020">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Malaria is one of the major health problems in developing countries. The disease kills a large number of people every year and also affects financial status of many countries. Resistance of the plasmodium parasite, the causative agent, to the existing drugs, including chloroquine, mefloquine, and artemisinin based combination therapy (ACT), is a serious global issue in malaria treatment and control. This warrants an urgent quest for novel compounds, particularly from natural sources such as medicinal plants. Alkaloids have over the years been recognized as important phytoconstituents with interesting biological properties. In fact, the first successful antimalarial drug was quinine, an alkaloid, which was extracted from Cinchona tree. In the present review work, the alkaloids isolated and reported recently (2013 till 2019) to possess antimalarial activity are presented. Several classes of alkaloids, including terpenoidal, indole, bisindole, quinolone, and isoquinoline alkaloids, were identified with a promising antimalarial activity. It is hoped that the reports of the review work will spur further research into the structural modification and/or development of the interesting compounds as novel antimalarial drugs.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Ashok, P" uniqKey="Ashok P">P. Ashok</name></author><author><name sortKey="Ganguly, S" uniqKey="Ganguly S">S. Ganguly</name></author><author><name sortKey="Murugesan, S" uniqKey="Murugesan S">S. Murugesan</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kaur, K" uniqKey="Kaur K">K. Kaur</name></author><author><name sortKey="Jain, M" uniqKey="Jain M">M. Jain</name></author><author><name sortKey="Khan, S I" uniqKey="Khan S">S. I. Khan</name></author></analytic></biblStruct><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="Schlitzer, M" uniqKey="Schlitzer M">M. 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Evid Based Complement Alternat Med</journal-id><journal-id journal-id-type="iso-abbrev">Evid Based Complement Alternat Med</journal-id><journal-id journal-id-type="publisher-id">ECAM</journal-id><journal-title-group><journal-title>Evidence-based Complementary and Alternative Medicine : eCAM</journal-title></journal-title-group><issn pub-type="ppub">1741-427X</issn><issn pub-type="epub">1741-4288</issn><publisher><publisher-name>Hindawi</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">32104196</article-id><article-id pub-id-type="pmc">7037883</article-id><article-id pub-id-type="doi">10.1155/2020/8749083</article-id><article-categories><subj-group subj-group-type="heading"><subject>Review Article</subject></subj-group></article-categories><title-group><article-title>Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies</article-title></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid" authenticated="false">https://orcid.org/0000-0001-8505-1795</contrib-id><name><surname>Uzor</surname><given-names>Philip F.</given-names></name><email>philip.uzor@unn.edu.ng</email><xref ref-type="aff" rid="I1"></xref></contrib></contrib-group><aff id="I1">Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, 410001 Nsukka, Enugu State, Nigeria</aff><author-notes><fn fn-type="other"><p>Academic Editor: Ghee T. Tan</p></fn></author-notes><pub-date pub-type="collection"><year>2020</year></pub-date><pub-date pub-type="epub"><day>12</day><month>2</month><year>2020</year></pub-date><pub-date pub-type="pmc-release"><day>12</day><month>2</month><year>2020</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>2020</volume><elocation-id>8749083</elocation-id><history><date date-type="received"><day>9</day><month>3</month><year>2019</year></date><date date-type="rev-recd"><day>4</day><month>1</month><year>2020</year></date><date date-type="accepted"><day>21</day><month>1</month><year>2020</year></date></history><permissions><copyright-statement>Copyright © 2020 Philip F. Uzor.</copyright-statement><copyright-year>2020</copyright-year><license xlink:href="http://creativecommons.org/licenses/by/4.0/"><license-p>This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.</license-p></license></permissions><abstract><p>Malaria is one of the major health problems in developing countries. The disease kills a large number of people every year and also affects financial status of many countries. Resistance of the plasmodium parasite, the causative agent, to the existing drugs, including chloroquine, mefloquine, and artemisinin based combination therapy (ACT), is a serious global issue in malaria treatment and control. This warrants an urgent quest for novel compounds, particularly from natural sources such as medicinal plants. Alkaloids have over the years been recognized as important phytoconstituents with interesting biological properties. In fact, the first successful antimalarial drug was quinine, an alkaloid, which was extracted from Cinchona tree. In the present review work, the alkaloids isolated and reported recently (2013 till 2019) to possess antimalarial activity are presented. Several classes of alkaloids, including terpenoidal, indole, bisindole, quinolone, and isoquinoline alkaloids, were identified with a promising antimalarial activity. It is hoped that the reports of the review work will spur further research into the structural modification and/or development of the interesting compounds as novel antimalarial drugs.</p></abstract></article-meta></front><floats-group><fig id="fig1" orientation="portrait" position="float"><label>Figure 1</label><caption><p>Structures of some antimalarial drugs.</p></caption><graphic xlink:href="ECAM2020-8749083.001"></graphic></fig><fig id="fig2" orientation="portrait" position="float"><label>Figure 2</label><caption><p>Structures of terpenoidal and steroidal alkaloids.</p></caption><graphic xlink:href="ECAM2020-8749083.002"></graphic></fig><fig id="fig3" orientation="portrait" position="float"><label>Figure 3</label><caption><p>Structures of indole and related alkaloids with promising antiplasmodial activity.</p></caption><graphic xlink:href="ECAM2020-8749083.003"></graphic></fig><fig id="fig4" orientation="portrait" position="float"><label>Figure 4</label><caption><p>Structures of isoquinoline alkaloids.</p></caption><graphic xlink:href="ECAM2020-8749083.004"></graphic></fig><fig id="fig5" orientation="portrait" position="float"><label>Figure 5</label><caption><p>Structures of bisbenzylisoquinoline (<bold>40, 41,</bold> and <bold>44</bold>) and hasubanane (<bold>42</bold> and <bold>43</bold>) alkaloids.</p></caption><graphic xlink:href="ECAM2020-8749083.005"></graphic></fig><fig id="fig6" orientation="portrait" position="float"><label>Figure 6</label><caption><p>Structures of naphthylisoquinoline (<bold>45</bold>) and dimeric naphthylisoquinoline (<bold>46</bold>–<bold>48-</bold>) alkaloids.</p></caption><graphic xlink:href="ECAM2020-8749083.006"></graphic></fig><fig id="fig7" orientation="portrait" position="float"><label>Figure 7</label><caption><p>Structures of apophine (<bold>49, 50,</bold> and <bold>52</bold>), isoquinoline (<bold>51</bold>), bisbenzylisoquinoline (<bold>53</bold>), and morphinandienone (<bold>54</bold> and <bold>60</bold>) alkaloids.</p></caption><graphic xlink:href="ECAM2020-8749083.007"></graphic></fig><fig id="fig8" orientation="portrait" position="float"><label>Figure 8</label><caption><p>Structures of protoberberine alkaloids.</p></caption><graphic xlink:href="ECAM2020-8749083.008"></graphic></fig><fig id="fig9" orientation="portrait" position="float"><label>Figure 9</label><caption><p>Structures of Amaryllidaceae alkaloids.</p></caption><graphic xlink:href="ECAM2020-8749083.009"></graphic></fig><fig id="fig10" orientation="portrait" position="float"><label>Figure 10</label><caption><p>Chemical structures of cyclopeptides with antiplasmodial activity.</p></caption><graphic xlink:href="ECAM2020-8749083.010"></graphic></fig><fig id="fig11" orientation="portrait" position="float"><label>Figure 11</label><caption><p>Chemical structures of quinoline (<bold>88</bold> and <bold>89</bold>), pyridocoumarin (<bold>90</bold> and <bold>91</bold>), aristolactam (<bold>92</bold>), acridone (<bold>93</bold>), and macrocytic (<bold>94</bold>) alkaloids with antiplasmodial activity.</p></caption><graphic xlink:href="ECAM2020-8749083.011"></graphic></fig><table-wrap id="tab1" orientation="portrait" position="float"><label>Table 1</label><caption><p>Summary of antimalarial alkaloids derived from plants.</p></caption><table frame="hsides" rules="groups"><thead><tr><th align="left" rowspan="1" colspan="1">Name</th><th align="center" rowspan="1" colspan="1">Class of alkaloid</th><th align="center" rowspan="1" colspan="1">Source</th><th align="center" rowspan="1" colspan="1">Activity against <italic>P. falciparum</italic></th><th align="center" rowspan="1" colspan="1">Reference</th></tr></thead><tbody><tr><td align="left" rowspan="1" colspan="1">Two new compounds: caesalminines A (<bold>1</bold>) and caesalminines B (<bold>2</bold>)</td><td align="center" rowspan="1" colspan="1">Cassane-type diterpene alkaloids</td><td align="center" rowspan="1" colspan="1">Seeds of <italic>Caesalpinia minax</italic></td><td align="center" rowspan="1" colspan="1"><italic>In vitro</italic> activity with IC<sub>50</sub>: 0.42 <italic>μ</italic>M (<bold>1</bold>) and 0.79 <italic>μ</italic>M (<bold>2</bold>)</td><td align="center" rowspan="1" colspan="1">[<xref rid="B21" ref-type="bibr">21</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Three new compounds: 8<italic>α</italic>-polyveolinone (<bold>3</bold>), <italic>N</italic>-acetyl-8<italic>α</italic>-polyveolinone (<bold>4</bold>), and <italic>N</italic>-acetyl-polyveoline (<bold>5</bold>)</td><td align="center" rowspan="1" colspan="1">Indolosesquiterpene alkaloids</td><td align="center" rowspan="1" colspan="1">Stem bark of <italic>Polyalthia oliveri</italic></td><td align="center" rowspan="1" colspan="1">Compounds <bold>4</bold> and <bold>5</bold> exhibit moderate activity against NF54 strain, with low cytotoxicity on L6 cell line</td><td align="center" rowspan="1" colspan="1">[<xref rid="B22" ref-type="bibr">22</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Three known alkaloids together with strychnochrysine (<bold>6</bold>)</td><td align="center" rowspan="1" colspan="1">Bisindolomonoterpenic alkaloid</td><td align="center" rowspan="1" colspan="1"><italic>Strychnos nux-vomica</italic> L</td><td align="center" rowspan="1" colspan="1">Compound <bold>7</bold> is the most active with IC<sub>50</sub> 10 <italic>μ</italic>M against D7 strain</td><td align="center" rowspan="1" colspan="1">[<xref rid="B23" ref-type="bibr">23</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Two known alkaloids: polyalthenol (<bold>7</bold>) and <italic>N</italic>-acetyl-polyveoline (<bold>5</bold>), together with other compounds</td><td align="center" rowspan="1" colspan="1">Indolosesquiterpene</td><td align="center" rowspan="1" colspan="1"><italic>Greenwayodendron suaveolens</italic> (Engl. & Diels) Verdc. (syn. <italic>Polyalthia suaveolens</italic> Engl. & Diels)</td><td align="center" rowspan="1" colspan="1">Highest activity was found for compound <bold>5</bold> against K1 strain with IC<sub>50</sub> value of 2.8 <italic>μ</italic>M, SI = 10.9</td><td align="center" rowspan="1" colspan="1">[<xref rid="B24" ref-type="bibr">24</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Conesine (<bold>8</bold>)</td><td align="center" rowspan="1" colspan="1">Steroidal alkaloid</td><td align="center" rowspan="1" colspan="1"><italic>Holarrhena antidysenterica</italic></td><td align="center" rowspan="1" colspan="1"><italic>Shows in vivo acivity against P. berghei</italic><break></break>Also shows <italic>in vitro</italic> activity against <italic>P. falciparum</italic> with IC₅₀ values of 1.9 <italic>μ</italic>g/ml and 1.3 <italic>μ</italic>g/ml in the schizont maturation and pLDH assays, respectively; cytotoxicity IC<sub>50</sub> of 14 <italic>μ</italic>g/ml</td><td align="center" rowspan="1" colspan="1">[<xref rid="B25" ref-type="bibr">25</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">New compound: mokluangin D (<bold>9</bold>) with nine known steroidal alkaloids including irehline (<bold>10</bold>) and mokluangin A (<bold>11</bold>)</td><td align="center" rowspan="1" colspan="1">Pregnene-type alkaloid</td><td align="center" rowspan="1" colspan="1"><italic>Holarrhena pubescens</italic> roots</td><td align="center" rowspan="1" colspan="1">Compounds <bold>10</bold> and <bold>11</bold> show strong activity against K1 strain with IC<sub>50</sub> values of 1.2 and 2.0 <italic>μ</italic>M and weak cytotoxicity against the NCI-H187 cell line</td><td align="center" rowspan="1" colspan="1">[<xref rid="B26" ref-type="bibr">26</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">The known alkaloid, <italic>N</italic>-3-benzoyldihydrocyclomicrophylline F (<bold>12</bold>), together with other compounds</td><td align="center" rowspan="1" colspan="1">Buxus alkaloid (a steroidal alkaloid) (compound <bold>12</bold>)</td><td align="center" rowspan="1" colspan="1"><italic>Buxus cochinchinensis</italic> Pierre ex Gagnep.</td><td align="center" rowspan="1" colspan="1">Compound <bold>12</bold> is active with IC<sub>50</sub> value of 2.07 ± 0.13 <italic>μ</italic>M; it shows cytotoxicity with IC<sub>50</sub> value of 1.9 <italic>μ</italic>M (against HT-29 human carcinoma) and > 20 (against NF-KB)</td><td align="center" rowspan="1" colspan="1">[<xref rid="B27" ref-type="bibr">27</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Three new compounds: alstoniaphyllines A <bold>(13)</bold>, alstoniaphyllines B (<bold>14</bold>), and alstoniaphylline C (<bold>15</bold>), and eight known alkaloids including alstonisine (<bold>16</bold>)</td><td align="center" rowspan="1" colspan="1">Nitrogenous derivatives (<bold>13</bold> and <bold>14</bold>) and indole alkaloid (<bold>15</bold>)</td><td align="center" rowspan="1" colspan="1"><italic>Alstonia macrophylla</italic> bark</td><td align="center" rowspan="1" colspan="1">Compound <bold>16</bold> exhibits activity with IC<sub>50</sub> value of 7.6 <italic>μ</italic>M</td><td align="center" rowspan="1" colspan="1">[<xref rid="B28" ref-type="bibr">28</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">A new compound, 12-hydroxy-<italic>N</italic>-acetyl-21(<italic>N</italic>)-dehydroplumeran-18-oic acid (<bold>17</bold>), and 11 known indole alkaloids including 20-epi-dasycarpidone (<bold>18</bold>)</td><td align="center" rowspan="1" colspan="1">Indole alkaloid</td><td align="center" rowspan="1" colspan="1"><italic>Aspidosperma ulei</italic> Markgr</td><td align="center" rowspan="1" colspan="1">Only compound <bold>18</bold> is active (IC<sub>50</sub> value of 16.7 mM) against K1 strain and shows no toxicity to fibroblasts (IC<sub>50</sub> > 50 mg/mL).</td><td align="center" rowspan="1" colspan="1">[<xref rid="B29" ref-type="bibr">29</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">A new compound: strychnobaillonine (<bold>19</bold>)</td><td align="center" rowspan="1" colspan="1">Bisindole</td><td align="center" rowspan="1" colspan="1">Roots of <italic>Strychnos icaja</italic></td><td align="center" rowspan="1" colspan="1">Shows <italic>in vitro</italic> activity with IC<sub>50</sub> value of 1.1 <italic>μ</italic>M</td><td align="center" rowspan="1" colspan="1">[<xref rid="B30" ref-type="bibr">30</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Two new alkaloids together with five known alkaloids, including 16-demethoxycarbonylvoacamine (<bold>20</bold>)</td><td align="center" rowspan="1" colspan="1">Sarpagine-type indole alkaloids</td><td align="center" rowspan="1" colspan="1">Bark of <italic>Tabernaemontana macrocarpa</italic> Jack</td><td align="center" rowspan="1" colspan="1">Compound <bold>20</bold> shows activity against <italic>P. falciparum</italic> 3D7 and cytotoxic activity against human cell line, HepG2 cells</td><td align="center" rowspan="1" colspan="1">[<xref rid="B31" ref-type="bibr">31</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">New alkaloid, 4a,b-<italic>seco</italic>-dehydroantofine (<bold>21</bold>), and three known alkaloids, dehydrotylophorine (<bold>22</bold>), dehydroantofine (<bold>23</bold>), and tylophoridicine D (<bold>24</bold>)</td><td align="center" rowspan="1" colspan="1">Phenanthroindolizine alkaloids</td><td align="center" rowspan="1" colspan="1">Twigs of <italic>Ficus septica</italic></td><td align="center" rowspan="1" colspan="1">Compound <bold>21</bold> displays moderate activity against the 3D7 strain with IC<sub>50</sub> value of 4.0 <italic>μ</italic>M, whereas the known alkaloids <bold>22</bold>–<bold>24</bold> display strong activity (IC<sub>50</sub> 0.028, 0.42, and 0.058 <italic>μ</italic>M, respectively). The cytotoxicities of the compounds (<bold>21</bold>–<bold>24)</bold> against L929 cells are in the range of 8.2–56 <italic>μ</italic>M, while selectivity index is in the range of 14.0–1964.0</td><td align="center" rowspan="1" colspan="1">[<xref rid="B32" ref-type="bibr">32</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Seven known alkaloids: cycleanine (<bold>25</bold>), 10-demethylxylopinine(<bold>26</bold>), reticuline (<bold>27</bold>), laurotetanine (<bold>28</bold>), bicuculine (<bold>29</bold>), <italic>α</italic>-hydrastine (<bold>30</bold>), and anolobine (<bold>31</bold>)</td><td align="center" rowspan="1" colspan="1">Isoquinoline alkaloids</td><td align="center" rowspan="1" colspan="1">Bark of <italic>Actinodaphne macrophylla</italic></td><td align="center" rowspan="1" colspan="1">They show <italic>in vitro</italic> activity with IC<sub>50</sub> values of 0.08 <italic>μ</italic>M, 0.05 <italic>μ</italic>M, 1.18 <italic>μ</italic>M, 3.11 <italic>μ</italic>M, 0.65 <italic>μ</italic>M, 0.26 <italic>μ</italic>M, and 1.38 <italic>μ</italic>M, respectively, against 3D7 strain</td><td align="center" rowspan="1" colspan="1">[<xref rid="B33" ref-type="bibr">33</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Four known alkaloids: (+)-<italic>N</italic>-methylisococlaurine (<bold>32</bold>), atherosperminine (<bold>33</bold>), 2-hydroxyathersperminine (<bold>34</bold>), and noratherosperminine (<bold>35</bold>)</td><td align="center" rowspan="1" colspan="1">Isoquinoline alkaloids</td><td align="center" rowspan="1" colspan="1">stem bark of <italic>Cryptocarya nigra</italic></td><td align="center" rowspan="1" colspan="1">They display activity with IC<sub>50</sub> values of 5.40, 5.80, and 0.75 <italic>μ</italic>M, respectively, for compounds <bold>32</bold>, <bold>33</bold>, and <bold>34</bold></td><td align="center" rowspan="1" colspan="1">[<xref rid="B34" ref-type="bibr">34</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Four alkaloids including palmatine (<bold>36</bold>)</td><td align="center" rowspan="1" colspan="1">Isoquinoline alkaloids</td><td align="center" rowspan="1" colspan="1">Leaves of <italic>Annickia kummeriae</italic></td><td align="center" rowspan="1" colspan="1">Compound <bold>36</bold> exhibits the highest activity against <italic>P. falciparum</italic> K1 (IC<sub>50</sub> 0.080 ± 0.001 <italic>μ</italic>g/mL, SI = 1154)</td><td align="center" rowspan="1" colspan="1">[<xref rid="B35" ref-type="bibr">35</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Known compounds: dihydronitidine (<bold>37</bold>), pellitorine (<bold>38</bold>), and heitziquinone (<bold>39</bold>)</td><td align="center" rowspan="1" colspan="1">Isoquinoline (dihydronitidine), decadienamide (pellitorine), and benzophenthrathridine (heitziquinone)</td><td align="center" rowspan="1" colspan="1"><italic>Zanthoxylum heitzii</italic> bark</td><td align="center" rowspan="1" colspan="1">Dihydronitidine (<bold>37</bold>) is the most active compound with an IC<sub>50</sub> value of 25 nM, while compounds <bold>38</bold> and <bold>39</bold> have IC<sub>50</sub> values of 9.7 ± 1.6 <italic>μ</italic>M and 8.8 ± 0.5 <italic>μ</italic>M, respectively</td><td align="center" rowspan="1" colspan="1">[<xref rid="B36" ref-type="bibr">36</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Three new alkaloids, (-)-pseudocurine (<bold>40</bold>), (-)-pseudoisocurine (<bold>41</bold>), and (-)-10-oxoaknadinine (<bold>42</bold>)</td><td align="center" rowspan="1" colspan="1">Bisbenzylisoquinoline alkaloids (<bold>40</bold> and <bold>41</bold>) and one hasubanane alkaloid (<bold>42</bold>)</td><td align="center" rowspan="1" colspan="1">Leaf of <italic>Stephania abyssinica</italic></td><td align="center" rowspan="1" colspan="1">They show strong-to-mild activity with IC<sub>50</sub> values ranging from 0.29 ± 0.00 to 1.65 ± 0.03 <italic>μ</italic>g/mL against both chloroquine-susceptible D6 and chloroquine-resistant strains</td><td align="center" rowspan="1" colspan="1">[<xref rid="B37" ref-type="bibr">37</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Six known alkaloids including (+)-laurotetanine (<bold>43</bold>) and (+)-norstephasubine (<bold>44</bold>)</td><td align="center" rowspan="1" colspan="1">Bisbenzylisoquinoline</td><td align="center" rowspan="1" colspan="1"><italic>Alseodaphne corneri</italic></td><td align="center" rowspan="1" colspan="1">Both compounds <bold>43</bold> and <bold>44</bold> show strong activity with IC<sub>50</sub> values of 0.189 and 0.116 <italic>μ</italic>M, respectively, against K1 strain and no cytotoxicity against hTERT-HPNE cell line</td><td align="center" rowspan="1" colspan="1">[<xref rid="B38" ref-type="bibr">38</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">One new dioncophyllaceous alkaloid, dioncophylline F (<bold>45</bold>), and other known alkaloids</td><td align="center" rowspan="1" colspan="1">Naphthylisoquinoline alkaloid (compound <bold>45</bold>)</td><td align="center" rowspan="1" colspan="1"><italic>Ancistrocladus ileboensis</italic></td><td align="center" rowspan="1" colspan="1">Compound <bold>45</bold> together with others shows high and specific activities against <italic>P. falciparum</italic></td><td align="center" rowspan="1" colspan="1">[<xref rid="B39" ref-type="bibr">39</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">New compounds: mbandakamines A (<bold>46</bold>) and B (<bold>47</bold>)</td><td align="center" rowspan="1" colspan="1">Dimeric naphthylisoquinoline alkaloids with an unsymmetrically coupled central biaryl axis</td><td align="center" rowspan="1" colspan="1">Unidentified <italic>Congolese Ancistrocladus</italic> species</td><td align="center" rowspan="1" colspan="1">Compound <bold>46</bold> exhibits good antimalarial activity</td><td align="center" rowspan="1" colspan="1">[<xref rid="B40" ref-type="bibr">40</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">New compound: jozimine A2 (<bold>48</bold>)</td><td align="center" rowspan="1" colspan="1">Dimeric naphthylisoquinoline alkaloid</td><td align="center" rowspan="1" colspan="1">Ancistrocladus species</td><td align="center" rowspan="1" colspan="1">Compound <bold>48</bold> exhibits excellent and specific antiplasmodial activity</td><td align="center" rowspan="1" colspan="1">[<xref rid="B41" ref-type="bibr">41</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">New alkaloid, vireakine (<bold>49</bold>), along with other known alkaloids including stephanine (<bold>50</bold>) and pseudopalmatine (<bold>51</bold>)</td><td align="center" rowspan="1" colspan="1">Aporphine alkaloid (<bold>49</bold>)</td><td align="center" rowspan="1" colspan="1">Tuber of <italic>Stephania rotunda</italic></td><td align="center" rowspan="1" colspan="1">Activity ranged from 1.2 <italic>μ</italic>M to 52.3 <italic>μ</italic>M for all tested compounds; compound <bold>51</bold> (IC<sub>50</sub> = 2.8 <italic>μ</italic>M) shows good selectivity index against W2 chloroquine-resistant strain</td><td align="center" rowspan="1" colspan="1">[<xref rid="B42" ref-type="bibr">42</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">A new alkaloid, obtusipetadione (<bold>52</bold>), and eleven known compounds</td><td align="center" rowspan="1" colspan="1">p-Quinonoid aporphine alkaloid (<bold>52</bold>)</td><td align="center" rowspan="1" colspan="1">Twigs of <italic>Dasymaschalon obtusipetalum</italic></td><td align="center" rowspan="1" colspan="1">Compound <bold>52</bold> is active with IC<sub>50</sub> values of 2.46 ± 0.12 and 1.38 ± 0.99 <italic>μ</italic>g/mL, respectively, for TM4 and K1 strains with no cytotoxicity</td><td align="center" rowspan="1" colspan="1">[<xref rid="B43" ref-type="bibr">43</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Several known alkaloids including (-)-O-O-dimethylgrisabine (<bold>53</bold>) and (-)-milonine (<bold>54)</bold></td><td align="center" rowspan="1" colspan="1">Morphinandienones; aporphines and benzlyisoquinoline</td><td align="center" rowspan="1" colspan="1">Bark of of <italic>Dehaasia longipedicellata</italic></td><td align="center" rowspan="1" colspan="1">They display potent-to-moderate activity with IC<sub>50</sub> values ranging from 0.031 to 30.40 <italic>μ</italic>M. Compounds <bold>53</bold> and <bold>54</bold> are the two most potent compounds, with IC<sub>50</sub> values of 0.031 and 0.097 <italic>μ</italic>M, respectively, against K1 strain. All the compounds show no potency against lung (A549) cancer cells</td><td align="center" rowspan="1" colspan="1">[<xref rid="B44" ref-type="bibr">44</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">A new alkaloid, anonaine (<bold>55</bold>), and other alkaloids</td><td align="center" rowspan="1" colspan="1">Aporphine alkaloids</td><td align="center" rowspan="1" colspan="1"><italic>Xylopia sericea</italic> leaves</td><td align="center" rowspan="1" colspan="1">Compound <bold>55</bold> is active against chloroquine-resistant W2 strain <italic>P. falciparum</italic> (IC<sub>50</sub> 23.2 ± 2.7 <italic>μ</italic>g/mL) and has moderate cytotoxicity against HepG2 cells (SI = 1.6)</td><td align="center" rowspan="1" colspan="1">[<xref rid="B45" ref-type="bibr">45</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">A new alkaloid, tavoyanine A (<bold>56</bold>), and other known alkaloids, roemerine (<bold>57</bold>), laurolitsine (<bold>58</bold>), boldine (<bold>59</bold>), and sebiferine (<bold>60</bold>)</td><td align="center" rowspan="1" colspan="1">Aporphine alkaloids (<bold>56</bold>–<bold>59</bold>) and morphinandienone (<bold>60</bold>)</td><td align="center" rowspan="1" colspan="1">Leaf of <italic>Phoebe tavoyana</italic></td><td align="center" rowspan="1" colspan="1">Compounds <bold>56</bold>–<bold>60</bold> are active against <italic>P. falciparum</italic> with IC<sub>50</sub> values of 0.89, 1.49, 1.65, and 2.76 <italic>μ</italic>g/mL, respectively</td><td align="center" rowspan="1" colspan="1">[<xref rid="B46" ref-type="bibr">46</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">A new alkaloid, simplicifolianine (<bold>61),</bold> together with five known alkaloids</td><td align="center" rowspan="1" colspan="1">Protoberberine-type alkaloid</td><td align="center" rowspan="1" colspan="1">Aerial components of <italic>Meconopsis simplicifolia</italic> (D. Don) Walpers</td><td align="center" rowspan="1" colspan="1">Compound <bold>22</bold> is the most potent against TM4/8.2 and K1CB1 with IC<sub>50</sub> values of 0.78 <italic>μ</italic>g/mL and 1.29 <italic>μ</italic>g/mL, respectively</td><td align="center" rowspan="1" colspan="1">[<xref rid="B47" ref-type="bibr">47</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">A known alkaloid, coptisine (<bold>62</bold>)</td><td align="center" rowspan="1" colspan="1">Protoberberine</td><td align="center" rowspan="1" colspan="1"><italic>Coptidis rhizoma</italic></td><td align="center" rowspan="1" colspan="1">Compound <bold>62</bold> is found to be an inhibitor of PfDHODH with an IC<sub>50</sub> value of 1.83 ± 0.08 <italic>μ</italic>m</td><td align="center" rowspan="1" colspan="1">[<xref rid="B48" ref-type="bibr">48</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Five new alkaloids, miliusacunines A-E (<bold>63</bold>–<bold>67</bold>), along with nine known compounds</td><td align="center" rowspan="1" colspan="1">Oxoprotoberberine alkaloids</td><td align="center" rowspan="1" colspan="1">Leaf and twigs of <italic>Miliusa cuneata</italic></td><td align="center" rowspan="1" colspan="1">Compound <bold>63</bold> shows activity against the TM4 strain (IC<sub>50</sub> 19.3 ± 3.4 <italic>μ</italic>M) and compound <bold>64</bold> shows activity against the K1 strain (IC<sub>50</sub> 10.8 ± 4.1 <italic>μ</italic>M). Both show no cytotoxicity to Vero cells</td><td align="center" rowspan="1" colspan="1">[<xref rid="B49" ref-type="bibr">49</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">One tetrahydroprotoberberine and four aporphine alkaloids including stephanine (<bold>50</bold>)</td><td align="center" rowspan="1" colspan="1">Tetrahydroprotoberberine alkaloid (compound <bold>50</bold>)</td><td align="center" rowspan="1" colspan="1">Tubers of <italic>Stephania venosa</italic> (Blum) Spreng</td><td align="center" rowspan="1" colspan="1">Stephanine (<bold>50</bold>) is the most interesting but is the most cytotoxic with the lowest selectivity index</td><td align="center" rowspan="1" colspan="1">[<xref rid="B50" ref-type="bibr">50</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Five new alkaloids, (+)-5,6-dehydrolycorine (<bold>68</bold>), (+)-3<italic>α</italic>,6<italic>β</italic>-diacetyl-bulbispermine (<bold>69</bold>), (+)-3<italic>α</italic>-hydroxy-6<italic>β</italic>-acetyl-bulbispermine (<bold>70</bold>), (+)-8,9-methylenedioxylhomolycorine-N-oxide (<bold>71</bold>), and 5,6-dihydro-5-methyl-2-hydroxyphenanthridine (<bold>72</bold>), together with other known compounds</td><td align="center" rowspan="1" colspan="1">Amaryllidaceae alkaloids</td><td align="center" rowspan="1" colspan="1">Bulbs of <italic>Lycoris radiata</italic></td><td align="center" rowspan="1" colspan="1">Compound <bold>68</bold> is active with IC<sub>50</sub> values of 2.3 <italic>μ</italic>M for D6 strain and 1.9 <italic>μ</italic>M for W2 strain; compound <bold>68</bold> also shows cytotoxicity against various carcinoma cells with IC<sub>50</sub> values of 9.4–11.6 <italic>μ</italic>M</td><td align="center" rowspan="1" colspan="1">[<xref rid="B51" ref-type="bibr">51</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Three known alkaloids, cripowellin A (<bold>73</bold>), cripowellin B (<bold>74</bold>), and hippadine (<bold>75</bold>), as well as the new compounds cripowellin C (<bold>76</bold>) and D (<bold>77</bold>)</td><td align="center" rowspan="1" colspan="1">Cripowellin alkaloids</td><td align="center" rowspan="1" colspan="1"><italic>Crinum erubescens</italic></td><td align="center" rowspan="1" colspan="1">Compounds <bold>73</bold>, <bold>74, 76</bold>, and <bold>77</bold> are active with IC<sub>50</sub> values of 30 ± 2, 180 ± 20, 26 ± 2, and 260 ± 20 nM, respectively, while <bold>75</bold> is inactive</td><td align="center" rowspan="1" colspan="1">[<xref rid="B52" ref-type="bibr">52</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">New alkaloid, 1,4-dihydroxy-3-methoxy powellan <bold>(78)</bold>, along with the known alkaloids, distichamine (<bold>79)</bold>, 11-O-acetylambelline (<bold>80</bold>), ambelline (<bold>81</bold>), acetylcaranine (<bold>82</bold>), and hippadine (<bold>75</bold>)</td><td align="center" rowspan="1" colspan="1">Crinane (<bold>78</bold>–<bold>81</bold>) and lycorane (<bold>82</bold> and <bold>75</bold>) alkaloids</td><td align="center" rowspan="1" colspan="1"><italic>Amaryllis belladonna</italic> Steud. Bulbs</td><td align="center" rowspan="1" colspan="1">Acetylcaranine (<bold>82</bold>) exhibits strong activity (IC<sub>50</sub> value of 3.3 ± 0.3 <italic>μ</italic>M), while compound <bold>78</bold> is inactive. Compound <bold>82</bold> shows weak inhibition against A2780 ovarian cells with an IC<sub>50</sub> value of 56 ± 1 <italic>μ</italic>M</td><td align="center" rowspan="1" colspan="1">[<xref rid="B53" ref-type="bibr">53</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Lycorine (<bold>83</bold>), along with 14 other alkaloids</td><td align="center" rowspan="1" colspan="1">Amaryllidaceae alkaloids</td><td align="center" rowspan="1" colspan="1"><italic>Worsleya procera</italic> roots</td><td align="center" rowspan="1" colspan="1">Compound <bold>83</bold> was active against both sensitive (3D7) and resistant (K1) <italic>P. falciparum</italic> strains with IC<sub>50</sub> values of 2.5 and 3.1 <italic>μ</italic>M, respectively, and a low cytotoxicity against HepG2 cells</td><td align="center" rowspan="1" colspan="1">[<xref rid="B54" ref-type="bibr">54</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Three new alkaloids, hymenocardinol (<bold>84</bold>), hymenocardine <italic>N</italic>-oxide (<bold>85</bold>), and hymenocardine-H (<bold>86</bold>), and one known alkaloid</td><td align="center" rowspan="1" colspan="1">Cyclopeptide alkaloids</td><td align="center" rowspan="1" colspan="1">Root bark of <italic>Hymenocardia acida</italic></td><td align="center" rowspan="1" colspan="1">All compounds show moderate activity with IC<sub>50</sub> values ranging from 12.2 to 27.9 <italic>μ</italic>M, the most active being compound <bold>85</bold> (IC<sub>50</sub> 12.2 ± 6.6 <italic>μ</italic>M). They are not cytotoxic against MRC-5 cells (IC<sub>50</sub> > 64.0 <italic>μ</italic>M)</td><td align="center" rowspan="1" colspan="1">[<xref rid="B56" ref-type="bibr">56</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Nine alkaloids including <italic>O</italic>-desmethylnummularine-R (<bold>87</bold>)</td><td align="center" rowspan="1" colspan="1">Cyclopeptide alkaloids</td><td align="center" rowspan="1" colspan="1">Roots of <italic>Ziziphus oxyphylla</italic></td><td align="center" rowspan="1" colspan="1">Most promising activity is found for compound <bold>87</bold> with IC<sub>50</sub> value of 3.2 ± 2.6 <italic>μ</italic>M against K1 strain and cytotoxcity (IC<sub>50</sub> value of >64.0 <italic>μ</italic>M) against MRC-5 cells</td><td align="center" rowspan="1" colspan="1">[<xref rid="B57" ref-type="bibr">57</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">A new alkaloid, microthecaline A (<bold>88</bold>)</td><td align="center" rowspan="1" colspan="1">Quinoline-serrulatane</td><td align="center" rowspan="1" colspan="1"><italic>Eremophila microtheca</italic></td><td align="center" rowspan="1" colspan="1">Compound <bold>88</bold> exhibits moderate activity against <italic>P. falciparum</italic> (3D7 strain), with an IC<sub>50</sub> value of 7.7 <italic>μ</italic>M</td><td align="center" rowspan="1" colspan="1">[<xref rid="B58" ref-type="bibr">58</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Seven known alkaloids including 6-methoxy-7-hydroxydictamnine (heliparvifoline) (<bold>89</bold>) and two known compounds</td><td align="center" rowspan="1" colspan="1">Furoquinoline alkaloids</td><td align="center" rowspan="1" colspan="1">Melicope madagascariensis</td><td align="center" rowspan="1" colspan="1">Heliparvifoline (<bold>89</bold>) shows weak antimalarial activity (IC<sub>50</sub> = 35 <italic>μ</italic>M) against Dd2 strain</td><td align="center" rowspan="1" colspan="1">[<xref rid="B59" ref-type="bibr">59</xref>]</td></tr><tr><td align="left" rowspan="1" colspan="1">Two new alkaloids, goniothalines A (<bold>90)</bold> and B (<bold>91</bold>), as well as eight known compounds including sauristolactam (<bold>92</bold>) as well as anonaine (<bold>55)</bold></td><td align="center" rowspan="1" colspan="1">Pyridocoumarin alkaloids</td><td align="center" rowspan="1" colspan="1">Aerial parts of <italic>Goniothalamus australis</italic></td><td align="center" rowspan="1" colspan="1">Sauristolactam (<bold>92</bold>) and (-)-anonaine (<bold>55</bold>) exhibit the most potent activity with IC<sub>50</sub> values of 9 and 7 <italic>μ</italic>M, respectively</td><td align="center" rowspan="1" colspan="1">[<xref rid="B60" ref-type="bibr">60</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Known alkaloids including normelicopine (<bold>93</bold>)</td><td align="center" rowspan="1" colspan="1">Acridone alkaloids</td><td align="center" rowspan="1" colspan="1"><italic>Zanthoxylum simullans</italic> Hance</td><td align="center" rowspan="1" colspan="1">Normelicopidine (<bold>93</bold>) is the most active against Dd2 with IC<sub>50</sub> value of 18.9 <italic>μ</italic>g/mL</td><td align="center" rowspan="1" colspan="1">[<xref rid="B61" ref-type="bibr">61</xref>]</td></tr><tr><td align="left" colspan="5" rowspan="1"><hr></hr></td></tr><tr><td align="left" rowspan="1" colspan="1">Carpaine (<bold>94</bold>)</td><td align="center" rowspan="1" colspan="1">Macrocyclic alkaloids</td><td align="center" rowspan="1" colspan="1"><italic>Carica papaya</italic> L. leaf</td><td align="center" rowspan="1" colspan="1">The compound is active against both 3D7 and Dd2 strains with IC<sub>50</sub> values of 4.21 <italic>μ</italic>M and 4.57 <italic>μ</italic>M, respectively, and high selectivity for the parasite</td><td align="center" rowspan="1" colspan="1">[<xref rid="B62" ref-type="bibr">62</xref>]</td></tr></tbody></table></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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