Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers
Identifieur interne : 000A67 ( Ncbi/Merge ); précédent : 000A66; suivant : 000A68Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers
Auteurs : Nelson G. M. Gomes ; Renato B. Pereira ; Paula B. Andrade ; Patrícia ValentãoSource :
- Marine Drugs [ 1660-3397 ] ; 2019.
Abstract
While several marine natural products bearing the 2,5-diketopiperazine ring have been reported to date, the unique chemistry of dimeric frameworks appears to remain neglected. Frequently reported from marine-derived strains of fungi, many naturally occurring diketopiperazine dimers have been shown to display a wide spectrum of pharmacological properties, particularly within the field of cancer and antimicrobial therapy. While their structures illustrate the unmatched power of marine biosynthetic machinery, often exhibiting unsymmetrical connections with rare linkage frameworks, enhanced binding ability to a variety of pharmacologically relevant receptors has been also witnessed. The existence of a bifunctional linker to anchor two substrates, resulting in a higher concentration of pharmacophores in proximity to recognition sites of several receptors involved in human diseases, portrays this group of metabolites as privileged lead structures for advanced pre-clinical and clinical studies. Despite the structural novelty of various marine diketopiperazine dimers and their relevant bioactive properties in several models of disease, to our knowledge, this attractive subclass of compounds is reviewed here for the first time.
Url:
DOI: 10.3390/md17100551
PubMed: 31569621
PubMed Central: 6835637
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PMC:6835637Le document en format XML
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<front><div type="abstract" xml:lang="en"><p>While several marine natural products bearing the 2,5-diketopiperazine ring have been reported to date, the unique chemistry of dimeric frameworks appears to remain neglected. Frequently reported from marine-derived strains of fungi, many naturally occurring diketopiperazine dimers have been shown to display a wide spectrum of pharmacological properties, particularly within the field of cancer and antimicrobial therapy. While their structures illustrate the unmatched power of marine biosynthetic machinery, often exhibiting unsymmetrical connections with rare linkage frameworks, enhanced binding ability to a variety of pharmacologically relevant receptors has been also witnessed. The existence of a bifunctional linker to anchor two substrates, resulting in a higher concentration of pharmacophores in proximity to recognition sites of several receptors involved in human diseases, portrays this group of metabolites as privileged lead structures for advanced pre-clinical and clinical studies. Despite the structural novelty of various marine diketopiperazine dimers and their relevant bioactive properties in several models of disease, to our knowledge, this attractive subclass of compounds is reviewed here for the first time. </p>
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</TEI>
<pmc article-type="review-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Mar Drugs</journal-id>
<journal-id journal-id-type="iso-abbrev">Mar Drugs</journal-id>
<journal-id journal-id-type="publisher-id">marinedrugs</journal-id>
<journal-title-group><journal-title>Marine Drugs</journal-title>
</journal-title-group>
<issn pub-type="epub">1660-3397</issn>
<publisher><publisher-name>MDPI</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">31569621</article-id>
<article-id pub-id-type="pmc">6835637</article-id>
<article-id pub-id-type="doi">10.3390/md17100551</article-id>
<article-id pub-id-type="publisher-id">marinedrugs-17-00551</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Review</subject>
</subj-group>
</article-categories>
<title-group><article-title>Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers</article-title>
</title-group>
<contrib-group><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-8727-9678</contrib-id>
<name><surname>Gomes</surname>
<given-names>Nelson G. M.</given-names>
</name>
</contrib>
<contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0001-8500-7364</contrib-id>
<name><surname>Pereira</surname>
<given-names>Renato B.</given-names>
</name>
</contrib>
<contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-9764-3920</contrib-id>
<name><surname>Andrade</surname>
<given-names>Paula B.</given-names>
</name>
</contrib>
<contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-0740-4396</contrib-id>
<name><surname>Valentão</surname>
<given-names>Patrícia</given-names>
</name>
<xref rid="c1-marinedrugs-17-00551" ref-type="corresp">*</xref>
</contrib>
</contrib-group>
<aff id="af1-marinedrugs-17-00551">REQUIMTE/LAQV, Laboratório de Farmacognosia, Departamento de Química, Faculdade de Farmácia, Universidade do Porto, R. Jorge Viterbo Ferreira, nº 228, Porto 4050-313, Portugal;<email>ngomes@ff.up.pt</email>
(N.G.M.G.);<email>ren.pereira@gmail.com</email>
(R.B.P.);<email>pandrade@ff.up.pt</email>
(P.B.A.)</aff>
<author-notes><corresp id="c1-marinedrugs-17-00551"><label>*</label>
Correspondence: <email>valentao@ff.up.pt</email>
; Tel.: +351-22-042-8653</corresp>
</author-notes>
<pub-date pub-type="epub"><day>27</day>
<month>9</month>
<year>2019</year>
</pub-date>
<pub-date pub-type="collection"><month>10</month>
<year>2019</year>
</pub-date>
<volume>17</volume>
<issue>10</issue>
<elocation-id>551</elocation-id>
<history><date date-type="received"><day>28</day>
<month>8</month>
<year>2019</year>
</date>
<date date-type="accepted"><day>25</day>
<month>9</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>While several marine natural products bearing the 2,5-diketopiperazine ring have been reported to date, the unique chemistry of dimeric frameworks appears to remain neglected. Frequently reported from marine-derived strains of fungi, many naturally occurring diketopiperazine dimers have been shown to display a wide spectrum of pharmacological properties, particularly within the field of cancer and antimicrobial therapy. While their structures illustrate the unmatched power of marine biosynthetic machinery, often exhibiting unsymmetrical connections with rare linkage frameworks, enhanced binding ability to a variety of pharmacologically relevant receptors has been also witnessed. The existence of a bifunctional linker to anchor two substrates, resulting in a higher concentration of pharmacophores in proximity to recognition sites of several receptors involved in human diseases, portrays this group of metabolites as privileged lead structures for advanced pre-clinical and clinical studies. Despite the structural novelty of various marine diketopiperazine dimers and their relevant bioactive properties in several models of disease, to our knowledge, this attractive subclass of compounds is reviewed here for the first time. </p>
</abstract>
<kwd-group><kwd>asperdimin</kwd>
<kwd>asperflocin</kwd>
<kwd>aspergilazine A</kwd>
<kwd>brevianamide S</kwd>
<kwd>chetracins</kwd>
<kwd>cristatumins</kwd>
<kwd>cristazine</kwd>
<kwd>eurocristatine</kwd>
<kwd>leptosins</kwd>
<kwd>naseseazines</kwd>
</kwd-group>
</article-meta>
</front>
<floats-group><fig id="marinedrugs-17-00551-f001" orientation="portrait" position="float"><label>Figure 1</label>
<caption><p>Structures of ditryptophenaline (<bold>1</bold>
), WIN 64821 (<bold>2</bold>
) and asymmetric stereoisomers (<bold>3</bold>
–<bold>6</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-17-00551-g001"></graphic>
</fig>
<fig id="marinedrugs-17-00551-f002" orientation="portrait" position="float"><label>Figure 2</label>
<caption><p>Structures of SF5280-451 (<bold>7</bold>
) and SF5280-415 (<bold>8</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-17-00551-g002"></graphic>
</fig>
<fig id="marinedrugs-17-00551-f003" orientation="portrait" position="float"><label>Figure 3</label>
<caption><p>Structures of asperdimin (<bold>9</bold>
), eurocristatine (<bold>10</bold>
), cristatumin C (<bold>11</bold>
) and (<bold>12</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-17-00551-g003"></graphic>
</fig>
<fig id="marinedrugs-17-00551-f004" orientation="portrait" position="float"><label>Figure 4</label>
<caption><p>Structures of verticillin A (<bold>13</bold>
), 11,11’-dideoxyverticillin A (<bold>14</bold>
), 11’-deoxyverticillin A (<bold>15</bold>
) and verticillins B-C (<bold>16</bold>
–<bold>17</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-17-00551-g004"></graphic>
</fig>
<fig id="marinedrugs-17-00551-f005" orientation="portrait" position="float"><label>Figure 5</label>
<caption><p>Structures of chaetocin (<bold>18</bold>
) and melinacidins II-IV (<bold>19</bold>
–<bold>21</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-17-00551-g005"></graphic>
</fig>
<fig id="marinedrugs-17-00551-f006" orientation="portrait" position="float"><label>Figure 6</label>
<caption><p>Structures of chetracins B (<bold>22</bold>
), C (<bold>23</bold>
), E (<bold>24</bold>
) and F (<bold>25</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-17-00551-g006"></graphic>
</fig>
<fig id="marinedrugs-17-00551-f007" orientation="portrait" position="float"><label>Figure 7</label>
<caption><p>Structures of leptosins (<bold>26</bold>
–<bold>46</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-17-00551-g007"></graphic>
</fig>
<fig id="marinedrugs-17-00551-f008" orientation="portrait" position="float"><label>Figure 8</label>
<caption><p>Structures of naseseazines A-C (<bold>47</bold>
–<bold>49</bold>
) and asperazine (<bold>50</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-17-00551-g008"></graphic>
</fig>
<fig id="marinedrugs-17-00551-f009" orientation="portrait" position="float"><label>Figure 9</label>
<caption><p>Structures of aspergilazine A (<bold>51</bold>
), chetomin (<bold>52</bold>
) and cristazine (<bold>53</bold>
).</p>
</caption>
<graphic xlink:href="marinedrugs-17-00551-g009"></graphic>
</fig>
<fig id="marinedrugs-17-00551-f010" orientation="portrait" position="float"><label>Figure 10</label>
<caption><p>Structures of brevianamides S (<bold>54</bold>
) and (<bold>55)</bold>
.</p>
</caption>
<graphic xlink:href="marinedrugs-17-00551-g010"></graphic>
</fig>
</floats-group>
</pmc>
<affiliations><list></list>
<tree><noCountry><name sortKey="Andrade, Paula B" sort="Andrade, Paula B" uniqKey="Andrade P" first="Paula B." last="Andrade">Paula B. Andrade</name>
<name sortKey="Gomes, Nelson G M" sort="Gomes, Nelson G M" uniqKey="Gomes N" first="Nelson G. M." last="Gomes">Nelson G. M. Gomes</name>
<name sortKey="Pereira, Renato B" sort="Pereira, Renato B" uniqKey="Pereira R" first="Renato B." last="Pereira">Renato B. Pereira</name>
<name sortKey="Valentao, Patricia" sort="Valentao, Patricia" uniqKey="Valentao P" first="Patrícia" last="Valentão">Patrícia Valentão</name>
</noCountry>
</tree>
</affiliations>
</record>
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