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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en"><italic>Maytenus macrocarpa</italic> (Ruiz & Pav.) Briq.: Phytochemistry and Pharmacological Activity</title><author><name sortKey="Malanik, Milan" sort="Malanik, Milan" uniqKey="Malanik M" first="Milan" last="Malaník">Milan Malaník</name><affiliation><nlm:aff id="af1-molecules-24-02288">Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</nlm:aff></affiliation></author><author><name sortKey="Treml, Jakub" sort="Treml, Jakub" uniqKey="Treml J" first="Jakub" last="Treml">Jakub Treml</name><affiliation><nlm:aff id="af2-molecules-24-02288">Department of Molecular Biology and Pharmaceutical Biotechnology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>tremlj@vfu.cz</email></nlm:aff></affiliation></author><author><name sortKey="Rjaskova, Veronika" sort="Rjaskova, Veronika" uniqKey="Rjaskova V" first="Veronika" last="Rjašková">Veronika Rjašková</name><affiliation><nlm:aff id="af1-molecules-24-02288">Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</nlm:aff></affiliation></author><author><name sortKey="Tizkova, Karolina" sort="Tizkova, Karolina" uniqKey="Tizkova K" first="Karolina" last="Tížková">Karolina Tížková</name><affiliation><nlm:aff id="af1-molecules-24-02288">Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</nlm:aff></affiliation></author><author><name sortKey="Kaucka, Petra" sort="Kaucka, Petra" uniqKey="Kaucka P" first="Petra" last="Kaucká">Petra Kaucká</name><affiliation><nlm:aff id="af1-molecules-24-02288">Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</nlm:aff></affiliation></author><author><name sortKey="Kokoska, Ladislav" sort="Kokoska, Ladislav" uniqKey="Kokoska L" first="Ladislav" last="Kokoška">Ladislav Kokoška</name><affiliation><nlm:aff id="af3-molecules-24-02288">Department of Crop Sciences and Agroforestry, Faculty of Tropical AgriSciences, Czech University of Life Sciences Prague, Kamýcká 129, 16500 Praha-Suchdol, Czech Republic;<email>kokoska@ftz.czu.cz</email></nlm:aff></affiliation></author><author><name sortKey="Kubatka, Peter" sort="Kubatka, Peter" uniqKey="Kubatka P" first="Peter" last="Kubatka">Peter Kubatka</name><affiliation><nlm:aff id="af4-molecules-24-02288">Department of Medical Biology, Jessenius Faculty of Medicine, Comenius University in Bratislava, 03601 Martin, Slovakia;<email>Peter.Kubatka@jfmed.uniba.sk</email></nlm:aff></affiliation></author><author><name sortKey="Smejkal, Karel" sort="Smejkal, Karel" uniqKey="Smejkal K" first="Karel" last="Šmejkal">Karel Šmejkal</name><affiliation><nlm:aff id="af1-molecules-24-02288">Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">31226757</idno><idno type="pmc">6630539</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6630539</idno><idno type="RBID">PMC:6630539</idno><idno type="doi">10.3390/molecules24122288</idno><date when="2019">2019</date><idno type="wicri:Area/Pmc/Corpus">000A67</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A67</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main"><italic>Maytenus macrocarpa</italic> (Ruiz & Pav.) Briq.: Phytochemistry and Pharmacological Activity</title><author><name sortKey="Malanik, Milan" sort="Malanik, Milan" uniqKey="Malanik M" first="Milan" last="Malaník">Milan Malaník</name><affiliation><nlm:aff id="af1-molecules-24-02288">Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</nlm:aff></affiliation></author><author><name sortKey="Treml, Jakub" sort="Treml, Jakub" uniqKey="Treml J" first="Jakub" last="Treml">Jakub Treml</name><affiliation><nlm:aff id="af2-molecules-24-02288">Department of Molecular Biology and Pharmaceutical Biotechnology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>tremlj@vfu.cz</email></nlm:aff></affiliation></author><author><name sortKey="Rjaskova, Veronika" sort="Rjaskova, Veronika" uniqKey="Rjaskova V" first="Veronika" last="Rjašková">Veronika Rjašková</name><affiliation><nlm:aff id="af1-molecules-24-02288">Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</nlm:aff></affiliation></author><author><name sortKey="Tizkova, Karolina" sort="Tizkova, Karolina" uniqKey="Tizkova K" first="Karolina" last="Tížková">Karolina Tížková</name><affiliation><nlm:aff id="af1-molecules-24-02288">Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</nlm:aff></affiliation></author><author><name sortKey="Kaucka, Petra" sort="Kaucka, Petra" uniqKey="Kaucka P" first="Petra" last="Kaucká">Petra Kaucká</name><affiliation><nlm:aff id="af1-molecules-24-02288">Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</nlm:aff></affiliation></author><author><name sortKey="Kokoska, Ladislav" sort="Kokoska, Ladislav" uniqKey="Kokoska L" first="Ladislav" last="Kokoška">Ladislav Kokoška</name><affiliation><nlm:aff id="af3-molecules-24-02288">Department of Crop Sciences and Agroforestry, Faculty of Tropical AgriSciences, Czech University of Life Sciences Prague, Kamýcká 129, 16500 Praha-Suchdol, Czech Republic;<email>kokoska@ftz.czu.cz</email></nlm:aff></affiliation></author><author><name sortKey="Kubatka, Peter" sort="Kubatka, Peter" uniqKey="Kubatka P" first="Peter" last="Kubatka">Peter Kubatka</name><affiliation><nlm:aff id="af4-molecules-24-02288">Department of Medical Biology, Jessenius Faculty of Medicine, Comenius University in Bratislava, 03601 Martin, Slovakia;<email>Peter.Kubatka@jfmed.uniba.sk</email></nlm:aff></affiliation></author><author><name sortKey="Smejkal, Karel" sort="Smejkal, Karel" uniqKey="Smejkal K" first="Karel" last="Šmejkal">Karel Šmejkal</name><affiliation><nlm:aff id="af1-molecules-24-02288">Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</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><italic>Maytenus macrocarpa</italic> (Celastraceae) is a tree native to Amazonia. Its roots, leaves, bark, and combinations of these are used in traditional medicine mainly to treat rheumatism and, to a lesser extent, to heal wounds and to combat bronchitis and diarrhea. To date, mainly triterpenes and dihydro-β-agarofuran sesquiterpenes were isolated from <italic>M. macrocarpa</italic>. Extracts and selected pure compounds isolated from the leaves, roots, and stem bark showed antibacterial, antiviral, antiparasitic, anti-inflammatory, and cytotoxic activities in vitro. The aim of this review is to summarize the available ethnobotanical, phytochemical, and pharmacological information about this traditional Amazonian medicinal tree, as well as to attract the attention of phytochemists and pharmacognosists to this potentially interesting source of ethnopharmaceuticals.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Liesner, R L" uniqKey="Liesner R">R.L. 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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">31226757</article-id><article-id pub-id-type="pmc">6630539</article-id><article-id pub-id-type="doi">10.3390/molecules24122288</article-id><article-id pub-id-type="publisher-id">molecules-24-02288</article-id><article-categories><subj-group subj-group-type="heading"><subject>Review</subject></subj-group></article-categories><title-group><article-title><italic>Maytenus macrocarpa</italic> (Ruiz & Pav.) Briq.: Phytochemistry and Pharmacological Activity</article-title></title-group><contrib-group><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0001-8700-8416</contrib-id><name><surname>Malaník</surname><given-names>Milan</given-names></name><xref ref-type="aff" rid="af1-molecules-24-02288">1</xref></contrib><contrib contrib-type="author"><name><surname>Treml</surname><given-names>Jakub</given-names></name><xref ref-type="aff" rid="af2-molecules-24-02288">2</xref></contrib><contrib contrib-type="author"><name><surname>Rjašková</surname><given-names>Veronika</given-names></name><xref ref-type="aff" rid="af1-molecules-24-02288">1</xref></contrib><contrib contrib-type="author"><name><surname>Tížková</surname><given-names>Karolina</given-names></name><xref ref-type="aff" rid="af1-molecules-24-02288">1</xref></contrib><contrib contrib-type="author"><name><surname>Kaucká</surname><given-names>Petra</given-names></name><xref ref-type="aff" rid="af1-molecules-24-02288">1</xref></contrib><contrib contrib-type="author"><name><surname>Kokoška</surname><given-names>Ladislav</given-names></name><xref ref-type="aff" rid="af3-molecules-24-02288">3</xref></contrib><contrib contrib-type="author"><name><surname>Kubatka</surname><given-names>Peter</given-names></name><xref ref-type="aff" rid="af4-molecules-24-02288">4</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-4336-7924</contrib-id><name><surname>Šmejkal</surname><given-names>Karel</given-names></name><xref ref-type="aff" rid="af1-molecules-24-02288">1</xref><xref rid="c1-molecules-24-02288" ref-type="corresp">*</xref></contrib></contrib-group><aff id="af1-molecules-24-02288"><label>1</label>Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>milan.malanik@seznam.cz</email> (M.M.);<email>v.rjaskova@gmail.com</email> (V.R.);<email>karolina.kalvarova@gmail.com</email> (K.T.);<email>petra.kaucka9@gmail.com</email> (P.K.)</aff><aff id="af2-molecules-24-02288"><label>2</label>Department of Molecular Biology and Pharmaceutical Biotechnology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1, 61242 Brno, Czech Republic;<email>tremlj@vfu.cz</email></aff><aff id="af3-molecules-24-02288"><label>3</label>Department of Crop Sciences and Agroforestry, Faculty of Tropical AgriSciences, Czech University of Life Sciences Prague, Kamýcká 129, 16500 Praha-Suchdol, Czech Republic;<email>kokoska@ftz.czu.cz</email></aff><aff id="af4-molecules-24-02288"><label>4</label>Department of Medical Biology, Jessenius Faculty of Medicine, Comenius University in Bratislava, 03601 Martin, Slovakia;<email>Peter.Kubatka@jfmed.uniba.sk</email></aff><author-notes><corresp id="c1-molecules-24-02288"><label>*</label>Correspondence: <email>karel.mejkal@post.cz</email></corresp></author-notes><pub-date pub-type="epub"><day>20</day><month>6</month><year>2019</year></pub-date><pub-date pub-type="collection"><month>6</month><year>2019</year></pub-date><volume>24</volume><issue>12</issue><elocation-id>2288</elocation-id><history><date date-type="received"><day>31</day><month>5</month><year>2019</year></date><date date-type="accepted"><day>18</day><month>6</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><italic>Maytenus macrocarpa</italic> (Celastraceae) is a tree native to Amazonia. Its roots, leaves, bark, and combinations of these are used in traditional medicine mainly to treat rheumatism and, to a lesser extent, to heal wounds and to combat bronchitis and diarrhea. To date, mainly triterpenes and dihydro-β-agarofuran sesquiterpenes were isolated from <italic>M. macrocarpa</italic>. Extracts and selected pure compounds isolated from the leaves, roots, and stem bark showed antibacterial, antiviral, antiparasitic, anti-inflammatory, and cytotoxic activities in vitro. The aim of this review is to summarize the available ethnobotanical, phytochemical, and pharmacological information about this traditional Amazonian medicinal tree, as well as to attract the attention of phytochemists and pharmacognosists to this potentially interesting source of ethnopharmaceuticals.</p></abstract><kwd-group><kwd>dihydro-β-agarofuran sesquiterpene</kwd><kwd>folk medicine</kwd><kwd><italic>Maytenus macrocarpa</italic></kwd><kwd>rheumatism</kwd><kwd>triterpene</kwd></kwd-group></article-meta></front><body><sec sec-type="intro" id="sec1-molecules-24-02288"><title>1. Introduction</title><p><italic>Maytenus macrocarpa</italic> (Ruiz & Pav.) Briq. is a tree, up to 30 m tall, belonging to the family Celastraceae. Four hundred different species of the genus <italic>Maytenus</italic> Molina were identified [<xref rid="B1-molecules-24-02288" ref-type="bibr">1</xref>]. Although <italic>M. macrocarpa</italic> is the most widely accepted scientific name, <italic>Celastrus macrocarpus</italic> Ruiz & Pav., <italic>Haenkea macrocarpa</italic> (Ruiz & Pav.) Steud., <italic>Haenkea multiflora</italic> Ruiz & Pav., <italic>M. multiflora</italic> (Ruiz & Pav.) Loes., and <italic>M. tarapotensis</italic> Briq. also refer to the same species. It is important to bear in mind that “chuchuhuasha” is a vernacular name for <italic>M. macrocarpa</italic> [<xref rid="B2-molecules-24-02288" ref-type="bibr">2</xref>] even though <italic>M. chuchuhuasha</italic> actually refers to another species—<italic>M. krukovii</italic> A.C. Sm. Another used vernacular name, chuchuhuasi, may refer to one or both of the species <italic>M. macrocarpa</italic> and <italic>M. amazonica</italic> Mart. ex Reissek [<xref rid="B3-molecules-24-02288" ref-type="bibr">3</xref>]. Other vernacular names in use are chuchuasi, chuchuasha [<xref rid="B4-molecules-24-02288" ref-type="bibr">4</xref>], chuchuwasha, chuchuwasha blanca [<xref rid="B5-molecules-24-02288" ref-type="bibr">5</xref>], chuchuhuasca [<xref rid="B2-molecules-24-02288" ref-type="bibr">2</xref>], and chichtá or xixuá [<xref rid="B6-molecules-24-02288" ref-type="bibr">6</xref>].</p><p>The fully correct classification of this plant is even more complicated because <italic>M. macrocarpa</italic> is often misidentified as <italic>M. ebenifolia</italic> Reissek or <italic>M. krukovii</italic> A.C. Sm. [<xref rid="B1-molecules-24-02288" ref-type="bibr">1</xref>,<xref rid="B7-molecules-24-02288" ref-type="bibr">7</xref>]. This chaos raised voices calling for reorganization of this plant family [<xref rid="B8-molecules-24-02288" ref-type="bibr">8</xref>]. Recently, the genus <italic>Maytenus</italic> was split into two genera, resurrected <italic>Tricerma</italic> and maintained <italic>Plenckia</italic> and <italic>Fraunhofera</italic> as separate ones. <italic>Maytenus</italic> species in the tropical lineage were transferred to <italic>Monteverdia</italic> [<xref rid="B9-molecules-24-02288" ref-type="bibr">9</xref>]; therefore, <italic>Monteverdia macrocarpa</italic> (Ruiz & Pav.) Biral should currently be the scientific name in use instead of <italic>Maytenus macrocarpa</italic>.</p><p>A review touching the ethnopharmacology, phytochemistry, and pharmacology of some <italic>Maytenus</italic> species was published [<xref rid="B10-molecules-24-02288" ref-type="bibr">10</xref>], but it made no specific reference to <italic>M. macrocarpa</italic>. The database literature search was performed in SciFinder and Google Scholar using keywords “<italic>Maytenus macrocarpa</italic>”, its isolated compounds, and corresponding pharmacological activities.</p></sec><sec id="sec2-molecules-24-02288"><title>2. Geographical Distribution</title><p>The <italic>M. macrocarpa</italic> tree grows exclusively in Amazonia. It is distributed in Bolivia, in Brazil in the state of Acre, in Columbia, in Ecuador in the provinces of Carchi, Esmeraldas, Imbabura, Napo, Pastaza, and Pichincha, in Peru in the regions Amazonas, Huánuco, Loreto, Madre de Dios, Paseo, San Martín, Tumbes, and Ucayali, and in Venezuela in the states of Anzoategui, Apure, Bolivar, and Miranda [<xref rid="B1-molecules-24-02288" ref-type="bibr">1</xref>,<xref rid="B2-molecules-24-02288" ref-type="bibr">2</xref>,<xref rid="B4-molecules-24-02288" ref-type="bibr">4</xref>,<xref rid="B6-molecules-24-02288" ref-type="bibr">6</xref>]. It grows mainly in lowland tropical rainforests, but exceptionally can be found up to 2000 m above sea level [<xref rid="B1-molecules-24-02288" ref-type="bibr">1</xref>].</p></sec><sec id="sec3-molecules-24-02288"><title>3. Phytochemistry</title><p><italic>M. macrocarpa</italic> was used in tribal folk medicine for many years, and this aroused interest in the compounds it contains. We searched the available literature for phytochemical research carried out on substances presented in <italic>M. macrocarpa</italic>. As previously mentioned, the situation is complicated by the fact that several synonymous names are used for this plant, and the literature describing its phytochemical analysis is not very rich.</p><p>Mejia and Rengifo (1995) reported that <italic>M. macrocarpa</italic> contains some simple phenols and quinones, but this reference lacks exact descriptions of the structures identified [<xref rid="B4-molecules-24-02288" ref-type="bibr">4</xref>]. The triterpenoids are a much better explored group of compounds isolated from <italic>M. macrocarpa</italic>. Several studies described the presence of mainly tetracyclic dammarane and pentacyclic friedelane triterpenes, and to a lesser extent quinonmethide, lupane, and oleane derived compounds. Another very interesting group of compounds obtained from <italic>M. macrocarpa</italic> consists of dihydro-β-agarofuran sesquiterpenes. <xref rid="molecules-24-02288-t001" ref-type="table">Table 1</xref>, including the corresponding references, presents a full list of the compounds isolated to date. Compounds presented in the <xref rid="molecules-24-02288-t001" ref-type="table">Table 1</xref> belong to various groups: dihydro-β-agarofuran sesquiterpenes (<bold>1</bold>–<bold>3</bold>), dammarane triterpenes (<bold>4</bold>–<bold>13</bold>), lupane triterpenes (<bold>14</bold>–<bold>18</bold>), and pentacyclic triterpenes (<bold>19</bold>–<bold>45</bold>).</p></sec><sec id="sec4-molecules-24-02288"><title>4. Folk Medicine</title><p>The <italic>M. macrocarpa</italic> plant is very popular in South American folk medicine. <italic>M. macrocarpa</italic> preparations are used to treat rheumatism almost everywhere in Amazonia. Other uses vary in the different regions. Ethnopharmacological studies showed that <italic>M. macrocarpa</italic> possesses aphrodisiac and anti-diarrheic effects and can also be used as a health and postpartum tonic and to enhance the healing of broken bones [<xref rid="B5-molecules-24-02288" ref-type="bibr">5</xref>]. It has antimalarial [<xref rid="B3-molecules-24-02288" ref-type="bibr">3</xref>,<xref rid="B25-molecules-24-02288" ref-type="bibr">25</xref>] and antileishmanial effects [<xref rid="B3-molecules-24-02288" ref-type="bibr">3</xref>]. Some local tribes use it to treat unspecified colds and women’s ailments, to enhance wound healing [<xref rid="B26-molecules-24-02288" ref-type="bibr">26</xref>], or to cure skin cancer [<xref rid="B27-molecules-24-02288" ref-type="bibr">27</xref>].</p><p>The most common local formulations use the stem bark and root of <italic>M. macrocarpa</italic> either decocted or macerated in the local rum, which is prepared from sugar cane [<xref rid="B5-molecules-24-02288" ref-type="bibr">5</xref>]. The following traditional recipes are presented here to illustrate the situation: for the treatment of rheumatism, macerate 250 g of dried shredded roots in alcohol and drink a glass on an empty stomach in the morning and evening regularly for a period of one month. The stem bark of <italic>M. macrocarpa</italic> can be used for the same purpose. For treatment of cold and bronchitis, boil 200 g of stem bark in 2 L of water for 1 h, add 250 mL of local rum, and allow this to macerate for ten days. Then, swallow a spoonful of this remedy every morning for 15 days [<xref rid="B4-molecules-24-02288" ref-type="bibr">4</xref>]. Another interesting use of <italic>M. macrocarpa</italic> is as a component remedy of a strict diet that is part of a ritual procedure called <italic>sama</italic>, used by locals in the Chazuta valley of Peru. The <italic>sama</italic> is a 2–8-week-long period of fasting during which plants with laxative and emetic effects are primarily consumed, supplemented with plants with other effects, e.g., anti-rheumatic effects [<xref rid="B28-molecules-24-02288" ref-type="bibr">28</xref>].</p></sec><sec id="sec5-molecules-24-02288"><title>5. Pharmacological Activities</title><sec id="sec5dot1-molecules-24-02288"><title>5.1. Antibacterial and Antifungal Activity</title><p>The increasing resistance of bacteria to antibiotics that are currently in use is forcing scientists to seek new compounds with strong antimicrobial activity. It is difficult to make a meaningful comparison of the results obtained in different antibacterial tests because the extracts and panels of test organisms employed are not standardized and different growth media were used in the assays. Some general endpoint criteria for assigning the activities of compounds or extracts, e.g., the half maximal inhibitory concentration (IC<sub>50</sub>) of the antibacterial effect below 100 µg/mL for test extracts and the IC<sub>50</sub> below 25 µM for pure compounds were adopted, but the close values obtained by testing the extracts are accepted more readily. Some scientific teams use assays that generate results expressed in minimal inhibitory concentration (MIC) or minimal bactericidal concentration (MBC), which can be tricky to compare. Furthermore, the minimal requirement for valid antibacterial assays is the use of at least one strain of Gram-positive and one strain of Gram-negative bacterium [<xref rid="B29-molecules-24-02288" ref-type="bibr">29</xref>]. According to a study conducted by Kloucek et al., an ethanolic extract obtained from the root bark of <italic>M. macrocarpa</italic> showed activity against <italic>Bacillus cereus</italic> American Type Culture Collection (ATCC) 11778, <italic>Bacillus subtilis</italic> ATCC 6633, <italic>Staphylococcus epidermidis</italic> ATCC 12228, <italic>Streptococcus pyogenes</italic> ATCC 19615, <italic>Escherichia coli</italic> ATCC 25922 (all at the MIC 125 µg/mL), and <italic>Enterococcus faecalis</italic> ATCC 29212, <italic>Staphylococcus aureus</italic> ATCC 25923, <italic>Bacteroides fragilis</italic> ATCC 25285, <italic>Pseudomonas aeruginosa</italic> ATCC 27853, and <italic>Candida albicans</italic> ATCC 10231 (all at the MIC of 250 µg/mL), whereas an ethanolic extract of stem bark did not show any activity against the same panel of bacterial strains [<xref rid="B30-molecules-24-02288" ref-type="bibr">30</xref>]. The differences between the results of the antibacterial activity testing of extracts prepared from roots and those from stem bark suggest that the spectrum of compounds present in root parts is different from the compounds present in aerial parts. The active extracts showed activity comparable to the antibiotic (ciprofloxacin) used as the standard control [<xref rid="B31-molecules-24-02288" ref-type="bibr">31</xref>]. However, the bacterial suspensions at a density of 10<sup>7</sup> colony-forming units (CFU)/mL used for the tests could cause false-negative results [<xref rid="B29-molecules-24-02288" ref-type="bibr">29</xref>], as confirmed by the data obtained for some compounds isolated from or present in <italic>M. macrocarpa</italic>. Scutione (<bold>24</bold>) showed strong activity against 11 Gram-positive bacterial strains (MIC 0.1–2.0 µg/mL), but no activity against eight Gram-negative bacterial strains (Gonzalez et al. 1996). In the same study, scutione (<bold>24</bold>) showed modest cytotoxic activity against HeLa, Hep-2, and Vero cell lines. It would, therefore, be worth testing scutione (<bold>24</bold>) against methicillin-resistant <italic>S. aureus</italic> (MRSA) and vancomycin-resistant <italic>Enterococci</italic> (VRE) because of the threat they pose to the human population.</p><p>The betuline derivative 3-(<italic>Z</italic>)-<italic>cis</italic>-coumaroylbetulin (<bold>15</bold>) showed relatively good activity against <italic>P. aeruginosa</italic> and <italic>S. aureus</italic> at a concentration of 0.1 mg/disc, whereas its <italic>trans</italic> isomer (<bold>16</bold>) showed much less activity. The antimicrobial activity was evaluated by the paper disc–agar diffusion method, where each disc (6 mm) was aseptically impregnated with 10 μL of the solution of the test compound [<xref rid="B32-molecules-24-02288" ref-type="bibr">32</xref>]. Maytenfolic acid (<bold>38</bold>) was shown to be active against <italic>S. aureus</italic> (MIC = 12.5 μg/mL) and <italic>P. aeruginosa</italic> (MIC = 12.5 μg/mL) [<xref rid="B33-molecules-24-02288" ref-type="bibr">33</xref>]. Neither 24-(<italic>Z</italic>)-3-oxo-dammara-20(21),24-dien-27-oic acid (<bold>13</bold>) nor octa-<italic>nor</italic>-13-hydroxydammara-1-en-3,17-dione (<bold>45</bold>) exhibited toxicity for any of the eight yeast strains tested using concentrations of at least 100 µg/mL [<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>]. Friedelin (<bold>19</bold>) was identified as an antimycobacterial compound against <italic>Mycobacterium madagascariense</italic> and <italic>M. indicus pranii</italic> [<xref rid="B34-molecules-24-02288" ref-type="bibr">34</xref>], but it showed low antimycobacterial activity against <italic>M. tuberculosis</italic> [<xref rid="B35-molecules-24-02288" ref-type="bibr">35</xref>] and, similarly to canophyllol (<bold>20</bold>) [<xref rid="B36-molecules-24-02288" ref-type="bibr">36</xref>], little or no activity against several fungal and bacterial species [<xref rid="B37-molecules-24-02288" ref-type="bibr">37</xref>,<xref rid="B38-molecules-24-02288" ref-type="bibr">38</xref>,<xref rid="B39-molecules-24-02288" ref-type="bibr">39</xref>,<xref rid="B40-molecules-24-02288" ref-type="bibr">40</xref>,<xref rid="B41-molecules-24-02288" ref-type="bibr">41</xref>]. The growth of several bacterial species was inhibited by friedelin (<bold>19</bold>) according to the work of Viswanathan et al. [<xref rid="B42-molecules-24-02288" ref-type="bibr">42</xref>], Ragasa et al. [<xref rid="B43-molecules-24-02288" ref-type="bibr">43</xref>], Jain et al. [<xref rid="B44-molecules-24-02288" ref-type="bibr">44</xref>], and Singh and Dubey [<xref rid="B45-molecules-24-02288" ref-type="bibr">45</xref>]; the good antibacterial activity of this compound against both Gram-positive and Gram-negative bacterial strains was described by Kuete et al. [<xref rid="B46-molecules-24-02288" ref-type="bibr">46</xref>,<xref rid="B47-molecules-24-02288" ref-type="bibr">47</xref>] and Sahiq Ali et al. [<xref rid="B48-molecules-24-02288" ref-type="bibr">48</xref>]; its weak activity against <italic>S. aureus</italic> was observed in a study done by Chiozem et al. [<xref rid="B49-molecules-24-02288" ref-type="bibr">49</xref>].</p></sec><sec id="sec5dot2-molecules-24-02288"><title>5.2. Antiviral Activity</title><p>Triterpenes, especially pentacyclic triterpenes and their derivatives, are known for their antiretroviral activity [<xref rid="B50-molecules-24-02288" ref-type="bibr">50</xref>,<xref rid="B51-molecules-24-02288" ref-type="bibr">51</xref>]. Betulinic acid and its derivatives were especially well explored for this effect [<xref rid="B52-molecules-24-02288" ref-type="bibr">52</xref>]. Studies reported that pentacyclic triterpenes inhibit human immunodeficiency virus (HIV) reverse transcriptase [<xref rid="B53-molecules-24-02288" ref-type="bibr">53</xref>]. Several pentacyclic triterpenes were isolated from <italic>M. macrocarpa</italic>. Piacente et al. [<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>] conducted an assay with a panel of 13 pentacyclic triterpenes isolated from a chloroform extract of the bark of <italic>M. macrocarpa</italic>: triptotriterpenonic acid A (<bold>39</bold>), 3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>), macrocarpoic acid A (<bold>36</bold>), macrocarpoic acid B (<bold>37</bold>), maytenfolic acid (<bold>38</bold>), macrocarpol A (<bold>43</bold>), 3-(<italic>E</italic>)-caffeoyluvaol (<bold>44</bold>), 3-(<italic>Z</italic>)-<italic>p</italic>-coumaroylbetulin (<bold>15</bold>), nepeticin (<bold>17</bold>), orthosphenic acid (<bold>42</bold>), 22-<italic>epi</italic>-maytenfolic acid (<bold>40</bold>), 22-<italic>epi</italic>-triptotriterpenonic acid A (<bold>41</bold>), and 3-(<italic>E</italic>)-<italic>p</italic>-coumaroylbetulin (<bold>16</bold>). These compounds were tested for anti-HIV activity in C8166 T cells infected with the HIV-1MN strain. The most effective compound was shown to be 22-<italic>epi</italic>-triptotriterpenonic acid A (<bold>41</bold>), which inhibited the interaction between the glycoprotein gp120 located on the HIV envelope and the cluster of differentiation 4 (CD4) receptor of T cells by 55% at the half maximal effective concentration (EC<sub>50</sub>) = 1 µg/mL. The selectivity index (the ratio of the cytotoxicity value against the particular cell line used to test the observed antiviral effect) was found to be 35, which is sufficient to warrant further testing [<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]. However, it is difficult to compare results obtained from this study with other studies reporting the antiviral activities of other triterpenes because different research groups used different viral strains and infected cells, and, in many cases, the data for positive controls were not published. Testing of further compounds showed that triptotriterpenonic acid A (<bold>39</bold>) is also active as an antiviral compound, but it is not selective enough when compared with substances currently used in clinics [<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]. Furthermore, 22-<italic>epi</italic>-maytenfolic acid (<bold>40</bold>) inhibited HIV replication in H9 lymphocyte cells with an EC<sub>50</sub> value of 5.65 µg/mL [<xref rid="B54-molecules-24-02288" ref-type="bibr">54</xref>]. Investigation of lupane derivatives revealed nepeticin (<bold>17</bold>) as a moderate inhibitor of HIV-1 replication in MT-2 cells infected with an X4 tropic HIV (NL4.3-Ren) (IC<sub>50</sub> = 10.4 µM), whereas 3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>) and lupeol (<bold>18</bold>) were inactive [<xref rid="B55-molecules-24-02288" ref-type="bibr">55</xref>].</p><p>The anti-HIV replication activities in H9 lymphocyte cells of friedelin (<bold>19</bold>) and canophyllol (<bold>20</bold>) were shown to be greater than 10 μg/mL [<xref rid="B56-molecules-24-02288" ref-type="bibr">56</xref>]. However, friedelin (<bold>19</bold>) was found to have no activity when tested against hepatitis virus type C [<xref rid="B57-molecules-24-02288" ref-type="bibr">57</xref>], it showed no HIV RNAase inhibitory activity [<xref rid="B58-molecules-24-02288" ref-type="bibr">58</xref>], and also did not affect reverse transcriptase [<xref rid="B59-molecules-24-02288" ref-type="bibr">59</xref>,<xref rid="B60-molecules-24-02288" ref-type="bibr">60</xref>]. Low activity of friedelin (<bold>19</bold>) against para-influenza virus type3 was also observed in a study by Jiang et al. [<xref rid="B61-molecules-24-02288" ref-type="bibr">61</xref>].</p></sec><sec id="sec5dot3-molecules-24-02288"><title>5.3. Antiparasitic Activity</title><p>Malaria kills more than two million people every year. Its etiological agent <italic>Plasmodium</italic> spp. frequently shows resistance to chloroquine and, for this reason, many scientists focused their research on finding new antimalarial remedies. Plant remedies would be a relatively convenient solution because of their accessibility [<xref rid="B25-molecules-24-02288" ref-type="bibr">25</xref>]. An ethanolic extract from the bark of <italic>M. macrocarpa</italic> was tested for antimalarial and antileishmanial activities in ethnopharmacological studies carried out in Loreto, Peru [<xref rid="B3-molecules-24-02288" ref-type="bibr">3</xref>]. It inhibited a chloroquine-susceptible strain of <italic>P. falciparum</italic> 3D7 at doses lower than 10 µg/mL (toxicity to human blood lymphocytes was proven at a dose of 48 µg/mL) in vitro [<xref rid="B3-molecules-24-02288" ref-type="bibr">3</xref>]. Recently, Vásquez-Ocmín et al. reported a study of 50 extracts from 46 medicinal plants used traditionally against protozoan diseases in Loreto (Peru) and an ethanolic extract from the bark of <italic>M. macrocarpa</italic> was one of the most active against <italic>P. falciparum</italic> 3D7 chloroquine-sensitive strain and against <italic>P. falciparum</italic> W2 chloroquine-resistant strain with IC<sub>50</sub> = 0.02 µg/mL for both strains [<xref rid="B62-molecules-24-02288" ref-type="bibr">62</xref>]. Pristimerin (<bold>26</bold>), an active compound isolated from <italic>M. macrocarpa</italic>, is unfortunately toxic to human cells (HT-29) [<xref rid="B3-molecules-24-02288" ref-type="bibr">3</xref>,<xref rid="B63-molecules-24-02288" ref-type="bibr">63</xref>], but only at concentrations approximately 10 times higher than required to kill <italic>P. falciparum</italic> K1 and <italic>P. falciparum</italic> NF54 (IC<sub>50</sub> 190.4 and 270.9 ng/mL, respectively) [<xref rid="B63-molecules-24-02288" ref-type="bibr">63</xref>]. Other studies showed that 3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>) was inactive at >50.0 μg/mL against <italic>P. falciparum</italic> K1 (multidrug-resistant strain) [<xref rid="B64-molecules-24-02288" ref-type="bibr">64</xref>], and 3-(<italic>Z</italic>)-<italic>p</italic>-coumaroylbetulin (<bold>15</bold>) and 3-(<italic>E</italic>)-<italic>p</italic>-coumaroylbetulin (<bold>16</bold>) possess only low activity when tested on mice infected with <italic>P. berghei</italic> [<xref rid="B65-molecules-24-02288" ref-type="bibr">65</xref>]. Friedelin (<bold>19</bold>) and canophyllol (<bold>20</bold>) showed some antiplasmodial activity when tested on the <italic>P. falciparum</italic> W2 strain (resistant to chloroquine) with IC<sub>50</sub> values of 7.2 and 15.0 μM, respectively [<xref rid="B66-molecules-24-02288" ref-type="bibr">66</xref>]; lower activity was shown in a study by Mitaine-Offer et al. [<xref rid="B67-molecules-24-02288" ref-type="bibr">67</xref>], when the activities of friedelin (<bold>19</bold>) and canophyllol (<bold>20</bold>) were compared to chloroquine (on both chloroquine-resistant and chloroquine-sensitive <italic>P. falciparum</italic> strains). Although an ethanolic extract from the bark of <italic>M. macrocarpa</italic> was active against both <italic>P. falciparum</italic> 3D7 and <italic>P. falciparum</italic> W2, reports of any antimalarial-active compounds found in <italic>M. macrocarpa</italic> are relatively scarce. According to Cos et al. [<xref rid="B29-molecules-24-02288" ref-type="bibr">29</xref>], research on potentially antimalarial-active compounds obtained from <italic>M. macrocarpa</italic> would benefit from the use of drug-resistant strains of <italic>Plasmodium</italic>.</p><p>Leishmaniasis is a serious disease that affects the developing world in particular. Three different forms of this disease are described—a cutaneous form (the most common), a mucocutaneous form (leading to partial or total destruction of mucous membranes), and a visceral form (the most serious form that can be lethal). Ethnopharmacological studies of <italic>M. macrocarpa</italic> describe its use to treat different wounds. Could the “wounds” reported by local people be the cutaneous form of leishmaniasis? The <italic>Leishmania major</italic> strain (the World Health Organization (WHO) referential strain) used in a brief antileishmanial-activity screening of an extract obtained from <italic>M. macrocarpa</italic> bark showed relatively strong inhibitory activity at doses lower than 10 µg/mL. Unfortunately, no strains of local clinically isolated <italic>Leishmania</italic> parasites were available for this study, and only the promastigote form of <italic>Leishmania</italic> was used in the assay. The predictive value of the test is, therefore, limited, and more experiments should be carried out to confirm the effect [<xref rid="B3-molecules-24-02288" ref-type="bibr">3</xref>]. A large study of the molecular docking of different substances, including a series of triterpenic compounds present in <italic>M. macrocarpa</italic>, identified the molecular protein targets of several <italic>Leishmania</italic> species [<xref rid="B68-molecules-24-02288" ref-type="bibr">68</xref>]. Friedelin (<bold>19</bold>) preferentially targeted <italic>L. major</italic> tyrosyl-tRNA synthetase (docking energy = −102.4 kJ/mol), whereas pristimerin (<bold>26</bold>) was strongly docked to <italic>L. major N</italic>-myristoyltransferase (docking energy = −112.9 kJ/mol), and lupeol (<bold>18</bold>) exerted the lowest-energy docked pose with <italic>L. major</italic> nucleoside hydrolase (docking energy = −99.0 kJ/mol) [<xref rid="B68-molecules-24-02288" ref-type="bibr">68</xref>]. Despite promising in silico results, friedelin (<bold>19</bold>) and epifriedelinol (<bold>29</bold>) showed no significant activity against <italic>L. donovani</italic> promastigotes [<xref rid="B69-molecules-24-02288" ref-type="bibr">69</xref>,<xref rid="B70-molecules-24-02288" ref-type="bibr">70</xref>]. Experiments with 3-caffeoylbetulin (<bold>14</bold>) showed it to be inactive against <italic>L. major</italic> as well [<xref rid="B71-molecules-24-02288" ref-type="bibr">71</xref>]. Additionally, 1α,6β,8β,15-tetraacetoxy-9α-benzoyloxy-4β-hydroxy-β-dihydroagarofuran (<bold>2</bold>), a dihydro-β-agarofuran sesquiterpene, is a promising antileishmanial substance isolated from <italic>M. macrocarpa</italic>. Alone, it possesses little direct cytotoxic activity against <italic>L. tropica</italic>, but it can also contribute to the effect of the currently used drug daunomycin by inhibiting the P-glycoprotein pump. This ATP-dependent transporting protein causes the efflux of daunomycin from cells [<xref rid="B72-molecules-24-02288" ref-type="bibr">72</xref>]. Dihydro-β-agarofuran sesquiterpenes block the P-glycoprotein pump and more daunomycin stays inside the cells to kill <italic>Leishmania</italic> more effectively. Blockers with greater affinity were, however, already discovered [<xref rid="B73-molecules-24-02288" ref-type="bibr">73</xref>].</p><p>An in silico molecular docking study was performed to investigate potential bioactive substances of antitrypanosomal plants. Although friedelin (<bold>19</bold>) was relatively weak docking ligands, it docked selectively with <italic>T. brucei</italic> uridine diphosphate (UDP)-galactose 4’-epimerase [<xref rid="B74-molecules-24-02288" ref-type="bibr">74</xref>]. On the other hand, friedelin (<bold>19</bold>) showed no antitrypanosomal activity in vitro [<xref rid="B70-molecules-24-02288" ref-type="bibr">70</xref>,<xref rid="B75-molecules-24-02288" ref-type="bibr">75</xref>,<xref rid="B76-molecules-24-02288" ref-type="bibr">76</xref>].</p></sec><sec id="sec5dot4-molecules-24-02288"><title>5.4. Cytotoxic Activity</title><p>Many studies of the cytotoxic activity of plant secondary metabolites were carried out, because of the urgent need for new remedies to treat cancer. <italic>M. macrocarpa</italic> was also examined as a potential source of cytotoxic substances. The direct cytotoxicity and mechanisms of effect of several compounds isolated from <italic>Maytenus</italic> were both analyzed. Pristimerin (<bold>26</bold>) inhibited DNA synthesis and triggered apoptosis in human HL-60 cells (promyelocytic leukemia cell line). It inhibited topoisomerase II, but it did not influence topoisomerase I [<xref rid="B19-molecules-24-02288" ref-type="bibr">19</xref>]. Pristimerin (<bold>26</bold>) also showed activity against the following cell lines with IC<sub>50</sub> values ranging from 0.55 µM to 3.20 µM: K-562 (chronic myelocytic leukemia), SF-295 (glyoblastoma), HCT-8 (colon carcinoma), and MDA/MB-435 (melanoma). However, except for MDA/MB-435, the dosage needed for the IC<sub>50</sub> effect was greater than that for doxorubicin, which is taken as the standard reference drug. Pristimerin (<bold>26</bold>) was toxic to PBMC (peripheral blood mononuclear cells) in the same concentration range, suggesting that this compound is relatively unselective [<xref rid="B19-molecules-24-02288" ref-type="bibr">19</xref>]. Another assay showed the cytotoxic potential of pristimerin (<bold>26</bold>) against HL-60 (IC<sub>50</sub> = 0.2 µM) and MCF7 (breast adenocarcinoma) (IC<sub>50</sub> = 0.4 µM) cell lines [<xref rid="B77-molecules-24-02288" ref-type="bibr">77</xref>]. Recently, the NCI-60 cell line screen revealed that pristimerin (<bold>26</bold>) was active against UO-31 (renal carcinoma), T-47D (breast cancer), and A549 (non-small-cell lung cancer) human tumor cell lines with individual half maximal inhibition of cell proliferation (GI<sub>50</sub>) values ranging from 0.12 µM to 1.2 µM [<xref rid="B78-molecules-24-02288" ref-type="bibr">78</xref>]; therefore, pristimerin (<bold>26</bold>) would deserve further in vivo evaluation. Macrocarpine A (<bold>32</bold>), macrocarpine B (<bold>33</bold>), macrocarpine C (<bold>34</bold>), and macrocarpine D (<bold>35</bold>) were shown to be active against P-388D1 (mouse lymphoma), A-549 (human lung carcinoma), HT-29 (human colon carcinoma), and MEL-28 (human melanoma) cells with IC<sub>50</sub> ranging between 0.4 and 5.2 µM [<xref rid="B24-molecules-24-02288" ref-type="bibr">24</xref>], whereas 28-hydroxyfriedelane-1,3-dione (<bold>22</bold>) was inactive against the same panel of cancer cell lines [<xref rid="B16-molecules-24-02288" ref-type="bibr">16</xref>], but a positive control was missing in both studies. Compounds macrocarpine A–D (<bold>32–35</bold>) were isolated from a hexane fraction, which shows the relatively lipophilic characteristic that could impede their solubility in water and, therefore, the likelihood that they could be used as drugs [<xref rid="B24-molecules-24-02288" ref-type="bibr">24</xref>]. An assay by Oramas-Royo et al. showed the activity of macrocarpine A (<bold>32</bold>) against HL-60 cells (IC<sub>50</sub> = 1.7 µM) [<xref rid="B77-molecules-24-02288" ref-type="bibr">77</xref>]. Vitideasin (<bold>25</bold>) was active against six solid tumor cell lines with IC<sub>50</sub> ranging between 2.7 and 5.4 µM [<xref rid="B79-molecules-24-02288" ref-type="bibr">79</xref>]. However, only in vitro studies are presented so far, and in vivo studies are needed. Recently, a review showing the anti-cancer potential of celastrol (<bold>28</bold>) was published [<xref rid="B80-molecules-24-02288" ref-type="bibr">80</xref>].</p><p>Derivatives of betulin are well known for cytotoxic properties. Several of them were isolated from <italic>M. macrocarpa</italic> (<bold>14–18</bold>). Furthermore, 3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>) and 3-(<italic>Z</italic>)-<italic>p</italic>-coumaroylbetulin (<bold>15</bold>) showed antitumor-promoting properties when tested in assays using the inhibition of soft agar colony induction by 12-<italic>O</italic>-tetradecanoylphorbol-13-acetate (TPA) in JB6 cells [<xref rid="B81-molecules-24-02288" ref-type="bibr">81</xref>]. Similarly, 3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>) was reported as a potent cytotoxic agent against SK-OV-3 (ovary malignant ascites) and SK-MEL-2 (skin melanoma) human cancer cell lines with IC<sub>50</sub> values of 9.0 and 2.9 µM, respectively [<xref rid="B82-molecules-24-02288" ref-type="bibr">82</xref>]. In another study, 3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>) exhibited moderate cytotoxic activity against KB (human oral epidermoid carcinoma) and NCI-H187 (human small-cell lung cancer) cell lines with IC<sub>50</sub> values of 28.4 and 16.2 µM, respectively. Unfortunately, 3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>) was cytotoxic also against Vero cells (IC<sub>50</sub> = 8.9 µM) [<xref rid="B64-molecules-24-02288" ref-type="bibr">64</xref>]. On the other hand, a different study of 3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>) showed no significant cytotoxicity against KB/S, KB/VJ300, and KU 19-20 cells [<xref rid="B83-molecules-24-02288" ref-type="bibr">83</xref>]. Additionally, 3-(<italic>E</italic>)-<italic>p</italic>-coumaroylbetulin (<bold>16</bold>) showed activity against KB and HUVEC (human umbilical vein endothelial cells) cell lines [<xref rid="B84-molecules-24-02288" ref-type="bibr">84</xref>]. Scutione (<bold>24</bold>) was tested for cytotoxic activity on HeLa (IC<sub>50</sub> = 4.9 µg/mL), Hep-2 (IC<sub>50</sub> = 5.6 µg/mL), and Vero (IC<sub>50</sub> = 7.2 µg/mL) cell lines and was not proven to be active compared with a positive control. This suggests dose-dependent activity against bacterial and mammalian cells and discriminating, non-specific toxicity [<xref rid="B18-molecules-24-02288" ref-type="bibr">18</xref>]. Canophyllol (<bold>20</bold>) and friedelin (<bold>19</bold>) showed moderate activity against HL-60 cells with IC<sub>50</sub> values of 17.1 and 48.5 µM, respectively [<xref rid="B85-molecules-24-02288" ref-type="bibr">85</xref>]. In addition, friedelin (<bold>19</bold>) was used as a lead compound for the synthesis of several analogs with a dose-dependent ability to inhibit the catalytic activity of human topoisomerase IIα [<xref rid="B86-molecules-24-02288" ref-type="bibr">86</xref>]. The activity of friedelin (<bold>19</bold>) was found to be responsible for the anti-tumor effect of bamboo shavings used in traditional Chinese medicine [<xref rid="B87-molecules-24-02288" ref-type="bibr">87</xref>]. Experiments using incubation with HeLa cells showed that the IC<sub>50</sub> of friedelin (<bold>19</bold>) was 37 μM. Friedelane-type triterpenoids also showed some anti-tumor promoting activity. Friedelin (<bold>19</bold>) had an inhibitory effect on Epstein–Barr virus early antigen (EBV-EA) activation induced by TPA [<xref rid="B88-molecules-24-02288" ref-type="bibr">88</xref>]. The application of selected triterpenes reduced inflammation in mouse ears induced by TPA and inhibited tumor genesis [<xref rid="B89-molecules-24-02288" ref-type="bibr">89</xref>]. A search in literature for the bioactivity of lupeol (<bold>18</bold>) found a review showing it has anti-cancer potential [<xref rid="B90-molecules-24-02288" ref-type="bibr">90</xref>].</p><p>Sesquiterpenes isolated from the leaves of <italic>M. macrocarpa</italic>, such as 6β,8β,15-triacetoxy-1α,9α-dibenzoyloxy-4β-hydroxy-β-dihydroagarofuran (<bold>1</bold>) and 1α,6β,8β,15-tetraacetoxy-9α-(benzoyloxy)-4β-hydroxy-β-dihydroagarofuran (<bold>2</bold>), were tested against P-388D1, A-549, HT-29, and MEL-28 cancer cell lines, but showed no significant cytotoxic activity [<xref rid="B11-molecules-24-02288" ref-type="bibr">11</xref>].</p></sec><sec id="sec5dot5-molecules-24-02288"><title>5.5. Anti-Inflammatory Activity</title><p>The focus on anti-inflammatory activity was emphasized on the basis of usage of <italic>M. macrocarpa</italic> as a component of medicinal preparations for treating rheumatism, which was mentioned by almost all of the local people who were questioned during the ethnopharmacological research in the area of the natural distribution of the tree, irrespective of the geographic region or ethnic group [<xref rid="B5-molecules-24-02288" ref-type="bibr">5</xref>,<xref rid="B26-molecules-24-02288" ref-type="bibr">26</xref>].</p><p>Celastrol (<bold>28</bold>), a pentacyclic triterpene isolated from <italic>M. macrocarpa</italic>, was tested for anti-inflammatory activity. This compound is also connected to Chinese medicine, where it is isolated from the medicinal plant <italic>Tripterygium wilfordii</italic> Hook (Celastraceae) and used to treat rheumatoid arthritis and spondylitis [<xref rid="B91-molecules-24-02288" ref-type="bibr">91</xref>]. Celastrol (<bold>28</bold>) was successful in many in vitro assays. It inhibited the release of interleukin (IL)-1α and IL-1β from lipopolysaccharide-stimulated human PBMC cells, inhibited activation of nuclear factor kappa B (NF-κB) and caspase-1, and reduced the secretion of IL-1β and tumor necrosis factor (TNF)-α in a human THP-1 macrophage-like cell line, and already went through in vivo tests in rats as an effective blocker of IL-1β and TNF-α, two cytokines connected with the development and progression of rheumatoid arthritis [<xref rid="B91-molecules-24-02288" ref-type="bibr">91</xref>,<xref rid="B92-molecules-24-02288" ref-type="bibr">92</xref>]. The question arises as to whether celastrol (<bold>28</bold>) is the only compound contained in <italic>M. macrocarpa</italic> that is responsible for anti-inflammatory activity. Some sources show that it may not be like that. In fact, 3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>) inhibited nitric oxide (NO) production (9.3 ± 3.2% of inhibition at 10 μM) and the formation of prostaglandin E2 (PGE2) (IC<sub>50</sub> = 10.8 μM) [<xref rid="B93-molecules-24-02288" ref-type="bibr">93</xref>], and 24-(<italic>E</italic>)-3-oxo-dammara-20,24-dien-26-ol (6) displayed moderate NO inhibitory activity (IC<sub>50</sub> = 22.36 μM) [<xref rid="B94-molecules-24-02288" ref-type="bibr">94</xref>] when tested in vitro on a system of RAW 264.7 cells stimulated by lipopolysaccharide (LPS). Lupeol (<bold>18</bold>) is a well-known substance with a multi-target anti-inflammatory potential as reported in reviews by Wal et al. [<xref rid="B95-molecules-24-02288" ref-type="bibr">95</xref>] and Siddique and Saleem [<xref rid="B96-molecules-24-02288" ref-type="bibr">96</xref>]. Oliveira-Junior et al. very recently demonstrated that lupeol (<bold>18</bold>) (0.1 μM) exhibited anti-neuroinflammatory and neuroprotective activity in cerebellar cells [<xref rid="B97-molecules-24-02288" ref-type="bibr">97</xref>]. Friedelin (<bold>19</bold>) can also possibly contribute to anti-inflammatory action [<xref rid="B98-molecules-24-02288" ref-type="bibr">98</xref>], as shown by its lipoxygenase inhibitory activity [<xref rid="B99-molecules-24-02288" ref-type="bibr">99</xref>] and several in vivo assays on mice [<xref rid="B100-molecules-24-02288" ref-type="bibr">100</xref>]. On the other hand, cyclooxygenase was inhibited only slightly and lipoxygenase not at all in another study [<xref rid="B101-molecules-24-02288" ref-type="bibr">101</xref>], and no inhibition of the platelet-activating factor (PAF)-stimulated release of β-glucuronidase from polymorphonuclear leukocytes was observed [<xref rid="B102-molecules-24-02288" ref-type="bibr">102</xref>]. Friedelin (<bold>19</bold>) was identified as an active substance in a test of the inhibition of carrageenan-induced paw edema in rats [<xref rid="B103-molecules-24-02288" ref-type="bibr">103</xref>], but an in vivo assay showed no activity of friedelin (<bold>19</bold>) and epifriedelinol (<bold>29</bold>) in the indomethacin-induced ulcer model in rats [<xref rid="B104-molecules-24-02288" ref-type="bibr">104</xref>]. Friedelin (<bold>19</bold>) only slightly inhibited the production of NO in RAW 264.7 cells [<xref rid="B105-molecules-24-02288" ref-type="bibr">105</xref>], and did not greatly inhibit the activity of nitric oxide synthase (NOS) in murine microglial cells [<xref rid="B106-molecules-24-02288" ref-type="bibr">106</xref>], but it moderately inhibited the secretion of TNF-α in the latter cell line at the relatively low concentration of 100 nM [<xref rid="B107-molecules-24-02288" ref-type="bibr">107</xref>]. Little activity was observed when friedelin (<bold>19</bold>) was tested for the inhibition of human leukocyte elastase (68% at a concentration of 25 μg/mL), which was quite different from canophyllol (<bold>20</bold>), which showed much greater activity (IC<sub>50</sub> = 2.5 μM) [<xref rid="B108-molecules-24-02288" ref-type="bibr">108</xref>]. Additionally, canophyllol (<bold>20</bold>) induced secretion of cytokines IL-6, IL-12, and TNF-α in PBMC cells [<xref rid="B109-molecules-24-02288" ref-type="bibr">109</xref>], and triptotriterpenonic acid A (<bold>39</bold>) showed a weak inhibitory effect on IL-2 release (27.0% inhibition at 10 μg/mL) and interferon (IFN)-γ release (66.7% inhibition at 10 μg/mL) produced by lipopolysaccharide-stimulated human PBMC cells [<xref rid="B21-molecules-24-02288" ref-type="bibr">21</xref>].</p></sec><sec id="sec5dot6-molecules-24-02288"><title>5.6. Other</title><p>Among other pharmacological activities described in the literature we found a positive effect of compounds from <italic>M. macrocarpa</italic> on impaired metabolic conditions, such as diabetes mellitus and obesity. Additionally, 3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>) showed weak α-glucosidase inhibitory activity (10.6% inhibition at 10 μg/mL) [<xref rid="B110-molecules-24-02288" ref-type="bibr">110</xref>], while 1α,6β,8β,15-tetraacetoxy-9α-(benzoyloxy)-4β-hydroxy-β-dihydroagarofuran (<bold>2</bold>) displayed good α-glucosidase inhibitory activity with IC<sub>50</sub> values of 42.58 μM [<xref rid="B111-molecules-24-02288" ref-type="bibr">111</xref>]. Very recently, in vivo, in vitro, and in silico studies reported that lupeol (<bold>18</bold>) possesses antidiabetic effects through a peroxisome proliferator-activated receptor (PPAR)δ/γ dual agonist action [<xref rid="B112-molecules-24-02288" ref-type="bibr">112</xref>], and canophyllol (<bold>20</bold>) stimulates the expression and translocation of glucose transporter 4 (GLUT4) in L6 myotubes in vitro (30 μg/mL), as well as in vivo in insulin-sensitive tissues of KK-Ay mice (60 mg/kg/day) via activation of the AMP-activated protein kinase (AMPK) pathway [<xref rid="B113-molecules-24-02288" ref-type="bibr">113</xref>].</p><p>On the other hand, 22-<italic>epi</italic>-maytenfolic acid (<bold>40</bold>) (IC<sub>50</sub> = 26 μM) and maytenfolic acid (<bold>38</bold>) (IC<sub>50</sub> = 72 μM) show inhibitory effects on rat lens aldose reductase, a key enzyme in the polyol pathway, where it catalyzes the reduction of glucose to sorbitol. Sorbitol does not readily diffuse across cell membranes, and the cellular accumulation of sorbitol was implicated in chronic complications of diabetes, such as cataracts [<xref rid="B114-molecules-24-02288" ref-type="bibr">114</xref>].</p><p>Maytenfolic acid (<bold>38</bold>) was shown to induce lipolysis in rat epididymal fat-derived adipocytes at 100 mg/L (100 μg/mL) [<xref rid="B115-molecules-24-02288" ref-type="bibr">115</xref>]. The role of celastrol (<bold>28</bold>) in metabolic diseases was well reviewed by Lan et al. [<xref rid="B116-molecules-24-02288" ref-type="bibr">116</xref>].</p></sec><sec id="sec5dot7-molecules-24-02288"><title>5.7. Toxicity Studies</title><p>Only one in vivo study using an ethanolic extract obtained from leaves of <italic>M. macrocarpa</italic> and intended to assess the safety of <italic>M. macrocarpa</italic> preparations was reported to date. A negative inotropic effect on the heart rate at a dose of 1500 mg/kg (1500 μg/g) was observed. Furthermore, no significant changes in the rectal temperature of rats were recorded at doses of 500 mg/kg (500 μg/g), 1000 mg/kg (1000 μg/g), and 1500 mg/kg (1500 μg/g) [<xref rid="B117-molecules-24-02288" ref-type="bibr">117</xref>]. However, the extract was administrated to the rats intraperitoneally, which is not the usual method of application. Although we found many inaccuracies in this research, we can assume that this drug should be safe at the dosages traditionally used, but more research would be welcome and reassuring.</p></sec></sec><sec id="sec6-molecules-24-02288"><title>6. Conclusions</title><p>This review was prepared to summarize the ethnobotanical, phytochemical, and pharmacological information about <italic>M. macrocarpa</italic>, a tree in the Celastraceae family. It is distributed in tropical lowland rainforests, with some exceptions growing up to 2000 m above sea level. Only Kvist et al. mentioned the possibility of different constituent compounds occurring at different altitudes, but even these authors suggested this could be due to confusion involving the vernacular name chuchuhuasi, which may refer to one or both of the species, <italic>M. macrocarpa</italic> and <italic>M. amazonica</italic>, with the former found mostly in flood-plain forests and the latter in upland forests [<xref rid="B3-molecules-24-02288" ref-type="bibr">3</xref>]. Examination of previous studies shows clearly that no differences between the content of compounds of lowland and highland trees were reported. Root and stem bark preparations of <italic>M. macrocarpa</italic> are widely used in Amazonian folk medicine to treat rheumatism and parasitic diseases. They are so popular that harvesting depleted the local <italic>M. macrocarpa</italic> trees close to villages [<xref rid="B26-molecules-24-02288" ref-type="bibr">26</xref>]. Even so, the evidence needed to register it as an evidence-based drug is insufficient. The bioactive substances must be identified, and in vivo studies of their effects must be carried out. The best explored compounds of <italic>M. macrocarpa</italic> are tetracyclic and pentacyclic triterpenes, and the dihydro-β-agarofuran sesquiterpenes are also noteworthy. Unfortunately, most of the compounds that were discovered are relatively large lipophilic molecules, and their resultant limited solubility in water makes it harder to use them as drugs. Nevertheless, progress in pharmaceutical technology (e.g., nanocarriers, encapsulation) could improve their bioavailability and solve this problem.</p><p>Summarizing the biological tests, the vast majority of assays were carried out in vitro, and they are yet to bring forth any promising active compounds. Despite promising results of antibacterial activity of an ethanolic extract obtained from the root bark of <italic>M. macrocarpa</italic>, the antibacterial activity of isolated compounds is not very strong compared to currently used antibiotics. Only scutione (<bold>24</bold>) displayed strong antibacterial activity and no cytotoxicity; it would, therefore, be worth testing against methicillin-resistant <italic>S. aureus</italic> (MRSA) and vancomycin-resistant <italic>Enterococci</italic> (VRE) because of the urgent medical need for new antibiotics effective against these highly aggressive and resistant bacterial strains.</p><p>Pharmacokinetic and toxicological studies still do not exist, but it can be deduced from traditionally used doses of long-term local preparations that <italic>M. macrocarpa</italic> is relatively safe. More studies should be carried out to determine the full medicinal value of <italic>M. macrocarpa</italic>. No events of deaths or serious health problems resulting from the use of extracts obtained from <italic>M. macrocarpa</italic> were reported; therefore, we suppose it is safe to ingest.</p></sec></body><back><ack><title>Acknowledgments</title><p>Thanks to Frank Thomas Campbell for careful proofreading of the manuscript.</p></ack><notes><title>Author Contributions</title><p>Conceptualization, M.M., L.K. and K.Š.; methodology, K.Š.; formal analysis, K.Š.; investigation, J.T., V.R., K.T., and P.K. (Petra Kaucká); data curation, K.Š., L.K.; writing—original draft preparation, K.Š., K.T., P.K. (Petra Kaucká); writing—review and editing, P.K. 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align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1">Reference</th></tr></thead><tbody><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>Dihydro-β-agarofurane sesquiterpene</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">6β,8β,15-triacetoxy-1α,9α-dibenzoyloxy-4β-hydroxy-β-dihydroagarofuran (<bold>1</bold>)<break></break>1α,6β,8β,15-tetraacetoxy-9α-(benzoyloxy)-4β-hydroxy-β-dihydroagarofuran (<bold>2</bold>) <break></break>(1<italic>S</italic>,4<italic>S</italic>,6<italic>R</italic>,7<italic>S</italic>,8<italic>S</italic>,9<italic>R</italic>)-1,6,15,triacetoxy-8α,9β-dibenzoyloxy)-4β-hydroxy-β-dihydroagarofuran (<bold>3</bold>)</td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i001.jpg"></inline-graphic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>Leaves</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B11-molecules-24-02288" ref-type="bibr">11</xref>]</td></tr><tr><td rowspan="10" align="center" valign="middle" style="border-bottom:solid thin" colspan="1"><bold>Dammarane triterpenes</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i002.jpg"></inline-graphic></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"></td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><bold>R</bold></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><bold>R1</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"></td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24-(<italic>E</italic>)-3-oxo-dammara-20,24-dien-26-al (<bold>4</bold>) <break></break>24-(<italic>Z</italic>)-3-oxo-dammara-20,24-dien-26-al (<bold>5</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i003.jpg"></inline-graphic></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">H</td><td rowspan="8" align="center" valign="middle" style="border-bottom:solid thin" colspan="1">Stem bark exudate</td><td rowspan="8" align="center" valign="middle" style="border-bottom:solid thin" colspan="1">[<xref rid="B11-molecules-24-02288" ref-type="bibr">11</xref>,<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24-(<italic>E</italic>)-3-oxo-dammara-20,24-dien-26-ol (<bold>6</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i004.jpg"></inline-graphic></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">H</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24-(<italic>E</italic>)-3-oxo-dammara-23α-hydroxy-20,24-dien-26-al (<bold>7</bold>) <break></break>24-(<italic>E</italic>)-3-oxo-dammara-23β-hydroxy-20,24-dien-26-al (<bold>8</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i005.jpg"></inline-graphic></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">H</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24-(<italic>E</italic>)-3-oxo-dammara-6β-hydroxy-20,24-dien-26-al (<bold>9</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i006.jpg"></inline-graphic></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">OH</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24-(<italic>E</italic>)-3-oxo-dammara-6β-hydroxy-20,24-dien-26-ol (<bold>10</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i007.jpg"></inline-graphic></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">OH</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">23-(<italic>Z</italic>)-3,25-dioxo-25-<italic>nor</italic>-dammara-20,24-dien (<bold>11</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i008.jpg"></inline-graphic></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">H</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24-(<italic>E</italic>)-3-oxo-22-hydroxy-23-methylene-dammara-20,24-dien-26-oic acid (<bold>12</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i009.jpg"></inline-graphic></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">H</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24-(<italic>Z</italic>)-3-oxo-dammara-20(21),24-dien-27-oic acid (<bold>13</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i010.jpg"></inline-graphic></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">H</td></tr><tr><td rowspan="7" align="center" valign="middle" style="border-bottom:solid thin" colspan="1"><bold>Lupane triterpenes</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i011.jpg"></inline-graphic></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"></td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><bold>R</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R1</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R2</bold></td><td rowspan="6" align="center" valign="middle" style="border-bottom:solid thin" colspan="1">Bark</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">3-(<italic>E</italic>)-caffeoylbetulin (<bold>14</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">3-(<italic>E</italic>)-caffeoyl</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">OH</td><td rowspan="4" align="center" valign="middle" style="border-bottom:solid thin" colspan="1">[<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">3-(<italic>Z</italic>)-<italic>p</italic>-coumaroylbetulin (<bold>15</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">3-(<italic>Z</italic>)-<italic>p</italic>-coumaroyl</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">OH</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">3-(<italic>E</italic>)-<italic>p</italic>-coumaroylbetulin (<bold>16</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">3-(<italic>E</italic>)-<italic>p</italic>-coumaroyl</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">OH</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">nepeticin (<bold>17</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">lupeol (<bold>18</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B11-molecules-24-02288" ref-type="bibr">11</xref>]</td></tr><tr><td rowspan="7" align="center" valign="middle" style="border-bottom:solid thin" colspan="1"><bold>Pentacyclic triterpenes</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i012.jpg"></inline-graphic></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"></td></tr><tr><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"><bold>R</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R1</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R2</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R3</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"></td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">friedelin (<bold>19</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark exudate, leaves</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>,<xref rid="B14-molecules-24-02288" ref-type="bibr">14</xref>,<xref rid="B15-molecules-24-02288" ref-type="bibr">15</xref>,<xref rid="B16-molecules-24-02288" ref-type="bibr">16</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">canophyllol (<bold>20</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>2</sub>OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td rowspan="4" align="center" valign="middle" style="border-bottom:solid thin" colspan="1">Stem bark exudate</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B16-molecules-24-02288" ref-type="bibr">16</xref>,<xref rid="B17-molecules-24-02288" ref-type="bibr">17</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">3-oxofriedelan-25-al (<bold>21</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CHO</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>,<xref rid="B16-molecules-24-02288" ref-type="bibr">16</xref>,<xref rid="B17-molecules-24-02288" ref-type="bibr">17</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">28-hydroxyfriedelane-1,3-dione (<bold>22</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>2</sub>OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">=O</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>,<xref rid="B16-molecules-24-02288" ref-type="bibr">16</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">3-oxo-29-hydroxyfriedelane (<bold>23</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>2</sub>OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>,<xref rid="B14-molecules-24-02288" ref-type="bibr">14</xref>,<xref rid="B15-molecules-24-02288" ref-type="bibr">15</xref>,<xref rid="B16-molecules-24-02288" ref-type="bibr">16</xref>]</td></tr><tr><td rowspan="4" align="center" valign="middle" style="border-bottom:solid thin" colspan="1"><bold>Pentacyclic triterpenes</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i013.jpg"></inline-graphic></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"></td></tr><tr><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"><bold>R</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R1</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R2</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R3</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"></td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">scutione (<bold>24</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">=O</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td rowspan="2" align="center" valign="middle" style="border-bottom:solid thin" colspan="1">Stem bark exudate</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B15-molecules-24-02288" ref-type="bibr">15</xref>,<xref rid="B18-molecules-24-02288" ref-type="bibr">18</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">netzahualcoyene (syn. vitideasin) (<bold>25</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">COOCH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>,<xref rid="B15-molecules-24-02288" ref-type="bibr">15</xref>]</td></tr><tr><td rowspan="5" align="center" valign="middle" style="border-bottom:solid thin" colspan="1"><bold>Pentacyclic triterpenes</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i014.jpg"></inline-graphic></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"></td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><bold>R</bold></td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><bold>R1</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"></td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">pristimerin (<bold>26</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">H</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">COOCH<sub>3</sub></td><td rowspan="3" align="center" valign="middle" style="border-bottom:solid thin" colspan="1">Stem bark exudate</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>,<xref rid="B15-molecules-24-02288" ref-type="bibr">15</xref>,<xref rid="B19-molecules-24-02288" ref-type="bibr">19</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">tingenone (<bold>27</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">=O</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">H</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B15-molecules-24-02288" ref-type="bibr">15</xref>,<xref rid="B20-molecules-24-02288" ref-type="bibr">20</xref>]</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">celastrol (<bold>28</bold>)</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">H</td><td colspan="2" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1">COOH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>,<xref rid="B15-molecules-24-02288" ref-type="bibr">15</xref>,<xref rid="B21-molecules-24-02288" ref-type="bibr">21</xref>]</td></tr><tr><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">epifriedelinol (syn. epifriedelanol) (<bold>29</bold>)</td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i015.jpg"></inline-graphic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Leaves</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B14-molecules-24-02288" ref-type="bibr">14</xref>,<xref rid="B15-molecules-24-02288" ref-type="bibr">15</xref>]</td></tr><tr><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">ilicifoline (D:A-friedoolean-1-en-29-ol-3-one) (<bold>30</bold>)</td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i016.jpg"></inline-graphic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark exudates</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>,<xref rid="B22-molecules-24-02288" ref-type="bibr">22</xref>]</td></tr><tr><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">According to Torpocco (2007), it was isolated as olean-12-ene-3β,6β-diol. Considering given references, it was isolated as olean-12-ene-3β,16β-diol (syn. maniladiol, daturadiol) (<bold>31</bold>)</td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i017.jpg"></inline-graphic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark exudates</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>,<xref rid="B23-molecules-24-02288" ref-type="bibr">23</xref>]</td></tr><tr><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">macrocarpine A (<bold>32</bold>)</td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i018.jpg"></inline-graphic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Root</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B24-molecules-24-02288" ref-type="bibr">24</xref>]</td></tr><tr><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">macrocarpine B (<bold>33</bold>) <break></break>macrocarpine C (<bold>34</bold>)</td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i019.jpg"></inline-graphic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Root</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B24-molecules-24-02288" ref-type="bibr">24</xref>]</td></tr><tr><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">macrocarpine D (<bold>35</bold>)</td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i020.jpg"></inline-graphic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Root</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B24-molecules-24-02288" ref-type="bibr">24</xref>]</td></tr><tr><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"></td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"></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"></td></tr><tr><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"></td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i021.jpg"></inline-graphic></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"></td></tr><tr><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"></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R1</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R2</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R3</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>R4</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"></td></tr><tr><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">macrocarpoic acid A <break></break>(3β, 22α-dihydroxy-olean-12-en-30-oic acid) (<bold>36</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">β-OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">COOH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">α-OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark exudates</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]</td></tr><tr><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">macrocarpoic acid B <break></break>(22α-hydroxy-olean-12-en-3-oxo-30-oic acid) (<bold>37</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">=O</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">COOH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">α-OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark exudates</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]</td></tr><tr><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">maytenfolic acid (triptotriterpenic acid A, 3β,20α,22α-dihydroxy-olean-12-en-29-oic acid) (<bold>38</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">β-OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">COOH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">α-OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark exudates</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]</td></tr><tr><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">triptotriterpenonic acid A (<bold>39</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">=O</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">COOH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">α-OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark exudates</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]</td></tr><tr><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">22-<italic>epi</italic>-maytenfolic acid (triptotriterpenic acid B, 3β,22α-dihydroxy-olean-12-en-29-oic acid) (<bold>40</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">β-OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">COOH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">β-OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark exudates</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]</td></tr><tr><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">22-<italic>epi</italic>-triptotriterpenonic acid A (<bold>41</bold>)</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">=O</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">COOH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">CH<sub>3</sub></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">β-OH</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark exudates</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]</td></tr><tr><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">orthosphenic acid (<bold>42</bold>)</td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i022.jpg"></inline-graphic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark extract</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]</td></tr><tr><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">3-(<italic>E</italic>)-coumaroyluvaol (macrocarpol A) (<bold>43</bold>) <break></break>3-(<italic>E</italic>)-caffeoyluvaol (<bold>44</bold>)</td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i023.jpg"></inline-graphic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark extract</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B13-molecules-24-02288" ref-type="bibr">13</xref>]</td></tr><tr><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">octa-<italic>nor</italic>-13-hydroxydammara-1-en-3,17-dione (<bold>45</bold>)</td><td colspan="4" align="center" valign="middle" style="border-bottom:solid thin" rowspan="1"><inline-graphic xlink:href="molecules-24-02288-i024.jpg"></inline-graphic></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Stem bark extract</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">[<xref rid="B12-molecules-24-02288" ref-type="bibr">12</xref>]</td></tr></tbody></table></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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