Malyngolide Dimer, a Bioactive Symmetric Cyclodepside from the Panamanian Marine Cyanobacterium Lyngbya majuscula
Identifieur interne : 001760 ( Main/Exploration ); précédent : 001759; suivant : 001761Malyngolide Dimer, a Bioactive Symmetric Cyclodepside from the Panamanian Marine Cyanobacterium Lyngbya majuscula
Auteurs : Marcelino Gutierrez [États-Unis, Panama] ; Kevin Tidgewell [États-Unis] ; Todd L. Capson [États-Unis] ; Niclas Engene [États-Unis] ; Alejandro Almanza [Panama] ; Jörg Schemies [Allemagne] ; Manfred Jung [Allemagne] ; William H. Gerwick [États-Unis]Source :
- Journal of natural products : (Print) [ 0163-3864 ] ; 2010.
Descripteurs français
- Pascal (Inist)
- Dimère, Activité biologique, Principe actif, Panama, Milieu marin, Cyanobacteria, Isolement, Configuration absolue, Lactone, Macrocycle, Antipaludique, Plasmodium falciparum, Cytotoxicité, Anticancéreux, Origine microbienne, Analyse structurale, Antiparasitaire, Antiprotozoaire, Lignée cellulaire, Cellule tumorale, Homme, Poumon, Carcinome non petite cellule, Lyngbya, Malyngolide dimère, 1,7-Dioxoacyclododécane-2,8-dione dérivé, Lignée H460.
- Wicri :
- geographic : Panama.
- topic : Milieu marin, Homme.
English descriptors
- KwdEn :
- Absolute configuration, Active ingredient, Antimalarial, Antineoplastic agent, Antiprotozoal agent, Biological activity, Cell line, Cyanobacteria, Cytotoxicity, Dimer, Human, Isolation, Lactone, Lung, Macrocycle, Marine environment, Microbial origin, Non small cell carcinoma, Panama, Parasiticide, Plasmodium falciparum, Structural analysis, Tumor cell.
Abstract
Fractionation of the extract of the marine cyanobacterium Lyngbya majuscula collected from Panama led to the isolation of malyngolide dimer (1). The planar structure of 1 was determined using 1D and 2D NMR spectroscopy and HRESI-TOFMS. The absolute configuration was established by chemical degradation followed by chiral GC-MS analyses and comparisons with an authentic sample of malyngolide seco-acid (4). Compound 1 showed moderate in vitro antimalarial activity against chloroquine-resistant Plasmodium falciparum (W2) (IC50 = 19 μM) but roughly equivalent toxicity against H-460 human lung cell lines. Furthermore, because the closely related cyanobacterial natural product tanikolide dimer (5) was a potent SIRT2 inhibitor, compound 1 was evaluated in this assay but found to be essentially inactive.
Affiliations:
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Gerwick</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego</s1><s2>La Jolla, California 92093</s2><s3>USA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>États-Unis</country><wicri:noRegion>La Jolla, California 92093</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">INIST</idno><idno type="inist">10-0358598</idno><date when="2010">2010</date><idno type="stanalyst">PASCAL 10-0358598 INIST</idno><idno type="RBID">Pascal:10-0358598</idno><idno type="wicri:Area/PascalFrancis/Corpus">000018</idno><idno type="wicri:Area/PascalFrancis/Curation">000048</idno><idno type="wicri:Area/PascalFrancis/Checkpoint">000017</idno><idno type="wicri:explorRef" wicri:stream="PascalFrancis" wicri:step="Checkpoint">000017</idno><idno type="wicri:doubleKey">0163-3864:2010:Gutierrez M:malyngolide:dimer:a</idno><idno type="wicri:Area/Main/Merge">001763</idno><idno type="wicri:Area/Main/Curation">001760</idno><idno type="wicri:Area/Main/Exploration">001760</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">Malyngolide Dimer, a Bioactive Symmetric Cyclodepside from the Panamanian Marine Cyanobacterium Lyngbya majuscula</title><author><name sortKey="Gutierrez, Marcelino" sort="Gutierrez, Marcelino" uniqKey="Gutierrez M" first="Marcelino" last="Gutierrez">Marcelino Gutierrez</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego</s1><s2>La Jolla, California 92093</s2><s3>USA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>États-Unis</country><wicri:noRegion>La Jolla, California 92093</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Instituto de Investigaciones Cientificas y Servicios de Alta Tecnología, Ciudad del Saber</s1><s2>Clayton, 0843-01103</s2><s3>PAN</s3><sZ>1 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Panama</country><wicri:noRegion>Clayton, 0843-01103</wicri:noRegion></affiliation></author><author><name sortKey="Tidgewell, Kevin" sort="Tidgewell, Kevin" uniqKey="Tidgewell K" first="Kevin" last="Tidgewell">Kevin Tidgewell</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego</s1><s2>La Jolla, California 92093</s2><s3>USA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>États-Unis</country><wicri:noRegion>La Jolla, California 92093</wicri:noRegion></affiliation></author><author><name sortKey="Capson, Todd L" sort="Capson, Todd L" uniqKey="Capson T" first="Todd L." last="Capson">Todd L. Capson</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego</s1><s2>La Jolla, California 92093</s2><s3>USA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>États-Unis</country><wicri:noRegion>La Jolla, California 92093</wicri:noRegion></affiliation></author><author><name sortKey="Engene, Niclas" sort="Engene, Niclas" uniqKey="Engene N" first="Niclas" last="Engene">Niclas Engene</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego</s1><s2>La Jolla, California 92093</s2><s3>USA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>États-Unis</country><wicri:noRegion>La Jolla, California 92093</wicri:noRegion></affiliation></author><author><name sortKey="Almanza, Alejandro" sort="Almanza, Alejandro" uniqKey="Almanza A" first="Alejandro" last="Almanza">Alejandro Almanza</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Instituto de Investigaciones Cientificas y Servicios de Alta Tecnología, Ciudad del Saber</s1><s2>Clayton, 0843-01103</s2><s3>PAN</s3><sZ>1 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Panama</country><wicri:noRegion>Clayton, 0843-01103</wicri:noRegion></affiliation></author><author><name sortKey="Schemies, Jorg" sort="Schemies, Jorg" uniqKey="Schemies J" first="Jörg" last="Schemies">Jörg Schemies</name><affiliation wicri:level="3"><inist:fA14 i1="03"><s1>Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Albertstrasse 25</s1><s2>79104 Freiburg</s2><s3>DEU</s3><sZ>6 aut.</sZ><sZ>7 aut.</sZ></inist:fA14><country>Allemagne</country><placeName><region type="land" nuts="1">Bade-Wurtemberg</region><region type="district" nuts="2">District de Fribourg-en-Brisgau</region><settlement type="city">Fribourg-en-Brisgau</settlement></placeName></affiliation></author><author><name sortKey="Jung, Manfred" sort="Jung, Manfred" uniqKey="Jung M" first="Manfred" last="Jung">Manfred Jung</name><affiliation wicri:level="3"><inist:fA14 i1="03"><s1>Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Albertstrasse 25</s1><s2>79104 Freiburg</s2><s3>DEU</s3><sZ>6 aut.</sZ><sZ>7 aut.</sZ></inist:fA14><country>Allemagne</country><placeName><region type="land" nuts="1">Bade-Wurtemberg</region><region type="district" nuts="2">District de Fribourg-en-Brisgau</region><settlement type="city">Fribourg-en-Brisgau</settlement></placeName></affiliation></author><author><name sortKey="Gerwick, William H" sort="Gerwick, William H" uniqKey="Gerwick W" first="William H." last="Gerwick">William H. Gerwick</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego</s1><s2>La Jolla, California 92093</s2><s3>USA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>États-Unis</country><wicri:noRegion>La Jolla, California 92093</wicri:noRegion></affiliation></author></analytic><series><title level="j" type="main">Journal of natural products : (Print)</title><title level="j" type="abbreviated">J. nat. prod. : (Print)</title><idno type="ISSN">0163-3864</idno><imprint><date when="2010">2010</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Journal of natural products : (Print)</title><title level="j" type="abbreviated">J. nat. prod. : (Print)</title><idno type="ISSN">0163-3864</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Absolute configuration</term><term>Active ingredient</term><term>Antimalarial</term><term>Antineoplastic agent</term><term>Antiprotozoal agent</term><term>Biological activity</term><term>Cell line</term><term>Cyanobacteria</term><term>Cytotoxicity</term><term>Dimer</term><term>Human</term><term>Isolation</term><term>Lactone</term><term>Lung</term><term>Macrocycle</term><term>Marine environment</term><term>Microbial origin</term><term>Non small cell carcinoma</term><term>Panama</term><term>Parasiticide</term><term>Plasmodium falciparum</term><term>Structural analysis</term><term>Tumor cell</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Dimère</term><term>Activité biologique</term><term>Principe actif</term><term>Panama</term><term>Milieu marin</term><term>Cyanobacteria</term><term>Isolement</term><term>Configuration absolue</term><term>Lactone</term><term>Macrocycle</term><term>Antipaludique</term><term>Plasmodium falciparum</term><term>Cytotoxicité</term><term>Anticancéreux</term><term>Origine microbienne</term><term>Analyse structurale</term><term>Antiparasitaire</term><term>Antiprotozoaire</term><term>Lignée cellulaire</term><term>Cellule tumorale</term><term>Homme</term><term>Poumon</term><term>Carcinome non petite cellule</term><term>Lyngbya</term><term>Malyngolide dimère</term><term>1,7-Dioxoacyclododécane-2,8-dione dérivé</term><term>Lignée H460</term></keywords><keywords scheme="Wicri" type="geographic" xml:lang="fr"><term>Panama</term></keywords><keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Milieu marin</term><term>Homme</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Fractionation of the extract of the marine cyanobacterium Lyngbya majuscula collected from Panama led to the isolation of malyngolide dimer (1). The planar structure of 1 was determined using 1D and 2D NMR spectroscopy and HRESI-TOFMS. The absolute configuration was established by chemical degradation followed by chiral GC-MS analyses and comparisons with an authentic sample of malyngolide seco-acid (4). Compound 1 showed moderate in vitro antimalarial activity against chloroquine-resistant Plasmodium falciparum (W2) (IC<sub>50</sub> = 19 μM) but roughly equivalent toxicity against H-460 human lung cell lines. Furthermore, because the closely related cyanobacterial natural product tanikolide dimer (5) was a potent SIRT2 inhibitor, compound 1 was evaluated in this assay but found to be essentially inactive.</div></front></TEI><affiliations><list><country><li>Allemagne</li><li>Panama</li><li>États-Unis</li></country><region><li>Bade-Wurtemberg</li><li>District de Fribourg-en-Brisgau</li></region><settlement><li>Fribourg-en-Brisgau</li></settlement></list><tree><country name="États-Unis"><noRegion><name sortKey="Gutierrez, Marcelino" sort="Gutierrez, Marcelino" uniqKey="Gutierrez M" first="Marcelino" last="Gutierrez">Marcelino Gutierrez</name></noRegion><name sortKey="Capson, Todd L" sort="Capson, Todd L" uniqKey="Capson T" first="Todd L." last="Capson">Todd L. Capson</name><name sortKey="Engene, Niclas" sort="Engene, Niclas" uniqKey="Engene N" first="Niclas" last="Engene">Niclas Engene</name><name sortKey="Gerwick, William H" sort="Gerwick, William H" uniqKey="Gerwick W" first="William H." last="Gerwick">William H. Gerwick</name><name sortKey="Tidgewell, Kevin" sort="Tidgewell, Kevin" uniqKey="Tidgewell K" first="Kevin" last="Tidgewell">Kevin Tidgewell</name></country><country name="Panama"><noRegion><name sortKey="Gutierrez, Marcelino" sort="Gutierrez, Marcelino" uniqKey="Gutierrez M" first="Marcelino" last="Gutierrez">Marcelino Gutierrez</name></noRegion><name sortKey="Almanza, Alejandro" sort="Almanza, Alejandro" uniqKey="Almanza A" first="Alejandro" last="Almanza">Alejandro Almanza</name></country><country name="Allemagne"><region name="Bade-Wurtemberg"><name sortKey="Schemies, Jorg" sort="Schemies, Jorg" uniqKey="Schemies J" first="Jörg" last="Schemies">Jörg Schemies</name></region><name sortKey="Jung, Manfred" sort="Jung, Manfred" uniqKey="Jung M" first="Manfred" last="Jung">Manfred Jung</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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