Malyngolide dimer, a bioactive symmetric cyclodepside from the panamanian marine cyanobacterium Lyngbya majuscula.
Identifieur interne : 001620 ( Main/Exploration ); précédent : 001619; suivant : 001621Malyngolide dimer, a bioactive symmetric cyclodepside from the panamanian marine cyanobacterium Lyngbya majuscula.
Auteurs : Marcelino Gutiérrez [États-Unis] ; Kevin Tidgewell ; Todd L. Capson ; Niclas Engene ; Alejandro Almanza ; Jörg Schemies ; Manfred Jung ; William H. GerwickSource :
- Journal of natural products [ 1520-6025 ] ; 2010.
Descripteurs français
- KwdFr :
- Biologie marine, Chloroquine (pharmacologie), Cyanobactéries (), Humains, Lactones (), Lactones (isolement et purification), Panama, Plasmodium falciparum (), Pyrones (), Pyrones (isolement et purification), Pyrones (pharmacologie), Relation structure-activité, Résistance aux substances (), Résonance magnétique nucléaire biomoléculaire, Structure moléculaire, Tests de sensibilité parasitaire, Toxines de Lyngbya (), Toxines de Lyngbya (isolement et purification), Toxines de Lyngbya (pharmacologie), Éthers cycliques (), Éthers cycliques (isolement et purification), Éthers cycliques (pharmacologie).
- MESH :
- isolement et purification : Lactones, Pyrones, Toxines de Lyngbya, Éthers cycliques.
- pharmacologie : Chloroquine, Pyrones, Toxines de Lyngbya, Éthers cycliques.
- Biologie marine, Cyanobactéries, Humains, Lactones, Panama, Plasmodium falciparum, Pyrones, Relation structure-activité, Résistance aux substances, Résonance magnétique nucléaire biomoléculaire, Structure moléculaire, Tests de sensibilité parasitaire, Toxines de Lyngbya, Éthers cycliques.
- Wicri :
- geographic : Panama.
English descriptors
- KwdEn :
- Chloroquine (pharmacology), Cyanobacteria (chemistry), Drug Resistance (drug effects), Ethers, Cyclic (chemistry), Ethers, Cyclic (isolation & purification), Ethers, Cyclic (pharmacology), Humans, Lactones (chemistry), Lactones (isolation & purification), Lyngbya Toxins (chemistry), Lyngbya Toxins (isolation & purification), Lyngbya Toxins (pharmacology), Marine Biology, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Panama, Parasitic Sensitivity Tests, Plasmodium falciparum (drug effects), Pyrones (chemistry), Pyrones (isolation & purification), Pyrones (pharmacology), Structure-Activity Relationship.
- MESH :
- chemical , chemistry : Ethers, Cyclic, Lactones, Lyngbya Toxins, Pyrones.
- chemical , isolation & purification : Ethers, Cyclic, Lactones, Lyngbya Toxins, Pyrones.
- chemical , pharmacology : Chloroquine, Ethers, Cyclic, Lyngbya Toxins, Pyrones.
- geographic : Panama.
- chemistry : Cyanobacteria.
- drug effects : Drug Resistance, Plasmodium falciparum.
- Humans, Marine Biology, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Parasitic Sensitivity Tests, Structure-Activity Relationship.
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) (IC(50) = 19 microM) 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.
DOI: 10.1021/np9005184
PubMed: 20158242
Affiliations:
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Le document en format XML
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Capson</name></author><author><name sortKey="Engene, Niclas" sort="Engene, Niclas" uniqKey="Engene N" first="Niclas" last="Engene">Niclas Engene</name></author><author><name sortKey="Almanza, Alejandro" sort="Almanza, Alejandro" uniqKey="Almanza A" first="Alejandro" last="Almanza">Alejandro Almanza</name></author><author><name sortKey="Schemies, Jorg" sort="Schemies, Jorg" uniqKey="Schemies J" first="Jörg" last="Schemies">Jörg Schemies</name></author><author><name sortKey="Jung, Manfred" sort="Jung, Manfred" uniqKey="Jung M" first="Manfred" last="Jung">Manfred Jung</name></author><author><name sortKey="Gerwick, William H" sort="Gerwick, William H" uniqKey="Gerwick W" first="William H" last="Gerwick">William H. Gerwick</name></author></analytic><series><title level="j">Journal of natural products</title><idno type="eISSN">1520-6025</idno><imprint><date when="2010" type="published">2010</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Chloroquine (pharmacology)</term><term>Cyanobacteria (chemistry)</term><term>Drug Resistance (drug effects)</term><term>Ethers, Cyclic (chemistry)</term><term>Ethers, Cyclic (isolation & purification)</term><term>Ethers, Cyclic (pharmacology)</term><term>Humans</term><term>Lactones (chemistry)</term><term>Lactones (isolation & purification)</term><term>Lyngbya Toxins (chemistry)</term><term>Lyngbya Toxins (isolation & purification)</term><term>Lyngbya Toxins (pharmacology)</term><term>Marine Biology</term><term>Molecular Structure</term><term>Nuclear Magnetic Resonance, Biomolecular</term><term>Panama</term><term>Parasitic Sensitivity Tests</term><term>Plasmodium falciparum (drug effects)</term><term>Pyrones (chemistry)</term><term>Pyrones (isolation & purification)</term><term>Pyrones (pharmacology)</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Biologie marine</term><term>Chloroquine (pharmacologie)</term><term>Cyanobactéries ()</term><term>Humains</term><term>Lactones ()</term><term>Lactones (isolement et purification)</term><term>Panama</term><term>Plasmodium falciparum ()</term><term>Pyrones ()</term><term>Pyrones (isolement et purification)</term><term>Pyrones (pharmacologie)</term><term>Relation structure-activité</term><term>Résistance aux substances ()</term><term>Résonance magnétique nucléaire biomoléculaire</term><term>Structure moléculaire</term><term>Tests de sensibilité parasitaire</term><term>Toxines de Lyngbya ()</term><term>Toxines de Lyngbya (isolement et purification)</term><term>Toxines de Lyngbya (pharmacologie)</term><term>Éthers cycliques ()</term><term>Éthers cycliques (isolement et purification)</term><term>Éthers cycliques (pharmacologie)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Ethers, Cyclic</term><term>Lactones</term><term>Lyngbya Toxins</term><term>Pyrones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Ethers, Cyclic</term><term>Lactones</term><term>Lyngbya Toxins</term><term>Pyrones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Chloroquine</term><term>Ethers, Cyclic</term><term>Lyngbya Toxins</term><term>Pyrones</term></keywords><keywords scheme="MESH" type="geographic" xml:lang="en"><term>Panama</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Cyanobacteria</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Drug Resistance</term><term>Plasmodium falciparum</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Lactones</term><term>Pyrones</term><term>Toxines de Lyngbya</term><term>Éthers cycliques</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Chloroquine</term><term>Pyrones</term><term>Toxines de Lyngbya</term><term>Éthers cycliques</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Humans</term><term>Marine Biology</term><term>Molecular Structure</term><term>Nuclear Magnetic Resonance, Biomolecular</term><term>Parasitic Sensitivity Tests</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Biologie marine</term><term>Cyanobactéries</term><term>Humains</term><term>Lactones</term><term>Panama</term><term>Plasmodium falciparum</term><term>Pyrones</term><term>Relation structure-activité</term><term>Résistance aux substances</term><term>Résonance magnétique nucléaire biomoléculaire</term><term>Structure moléculaire</term><term>Tests de sensibilité parasitaire</term><term>Toxines de Lyngbya</term><term>Éthers cycliques</term></keywords><keywords scheme="Wicri" type="geographic" xml:lang="fr"><term>Panama</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(50) = 19 microM) 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>États-Unis</li></country></list><tree><noCountry><name sortKey="Almanza, Alejandro" sort="Almanza, Alejandro" uniqKey="Almanza A" first="Alejandro" last="Almanza">Alejandro Almanza</name><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="Jung, Manfred" sort="Jung, Manfred" uniqKey="Jung M" first="Manfred" last="Jung">Manfred Jung</name><name sortKey="Schemies, Jorg" sort="Schemies, Jorg" uniqKey="Schemies J" first="Jörg" last="Schemies">Jörg Schemies</name><name sortKey="Tidgewell, Kevin" sort="Tidgewell, Kevin" uniqKey="Tidgewell K" first="Kevin" last="Tidgewell">Kevin Tidgewell</name></noCountry><country name="États-Unis"><noRegion><name sortKey="Gutierrez, Marcelino" sort="Gutierrez, Marcelino" uniqKey="Gutierrez M" first="Marcelino" last="Gutiérrez">Marcelino Gutiérrez</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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