Antimalarial activity of axidjiferosides, new β-galactosylceramides from the African sponge Axinyssa djiferi.
Identifieur interne : 000338 ( PubMed/Curation ); précédent : 000337; suivant : 000339Antimalarial activity of axidjiferosides, new β-galactosylceramides from the African sponge Axinyssa djiferi.
Auteurs : Fereshteh Farokhi [France] ; Philippe Grellier ; Monique Clément ; Christos Roussakis ; Philippe M. Loiseau ; Emilie Genin-Seward ; Jean-Michel Kornprobst ; Gilles Barnathan ; Gaëtane Wielgosz-CollinSource :
- Marine drugs [ 1660-3397 ] ; 2013.
Descripteurs français
- KwdFr :
- Animaux, Antipaludiques (administration et posologie), Antipaludiques (isolement et purification), Antipaludiques (pharmacologie), Chloroquine (pharmacologie), Concentration inhibitrice 50, Céramides (administration et posologie), Céramides (isolement et purification), Céramides (pharmacologie), Femelle, Galactosylcéramides (administration et posologie), Galactosylcéramides (isolement et purification), Galactosylcéramides (pharmacologie), Glycosphingolipides (administration et posologie), Glycosphingolipides (isolement et purification), Glycosphingolipides (pharmacologie), Humains, Lignée cellulaire tumorale, Oses (administration et posologie), Oses (isolement et purification), Oses (pharmacologie), Plasmodium falciparum (), Porifera (), Résistance aux substances, Souris, Sénégal, Tumeurs (anatomopathologie), Tumeurs (traitement médicamenteux).
- MESH :
- administration et posologie : Antipaludiques, Céramides, Galactosylcéramides, Glycosphingolipides, Oses.
- anatomopathologie : Tumeurs.
- isolement et purification : Antipaludiques, Céramides, Galactosylcéramides, Glycosphingolipides, Oses.
- pharmacologie : Antipaludiques, Chloroquine, Céramides, Galactosylcéramides, Glycosphingolipides, Oses.
- traitement médicamenteux : Tumeurs.
- Animaux, Concentration inhibitrice 50, Femelle, Humains, Lignée cellulaire tumorale, Plasmodium falciparum, Porifera, Résistance aux substances, Souris, Sénégal.
- Wicri :
- geographic : Sénégal.
English descriptors
- KwdEn :
- Animals, Antimalarials (administration & dosage), Antimalarials (isolation & purification), Antimalarials (pharmacology), Cell Line, Tumor, Ceramides (administration & dosage), Ceramides (isolation & purification), Ceramides (pharmacology), Chloroquine (pharmacology), Drug Resistance, Female, Galactosylceramides (administration & dosage), Galactosylceramides (isolation & purification), Galactosylceramides (pharmacology), Glycosphingolipids (administration & dosage), Glycosphingolipids (isolation & purification), Glycosphingolipids (pharmacology), Humans, Inhibitory Concentration 50, Mice, Monosaccharides (administration & dosage), Monosaccharides (isolation & purification), Monosaccharides (pharmacology), Neoplasms (drug therapy), Neoplasms (pathology), Plasmodium falciparum (drug effects), Porifera (chemistry), Senegal.
- MESH :
- chemical , administration & dosage : Antimalarials, Ceramides, Galactosylceramides, Glycosphingolipids, Monosaccharides.
- chemical , isolation & purification : Antimalarials, Ceramides, Galactosylceramides, Glycosphingolipids, Monosaccharides.
- chemical , pharmacology : Antimalarials, Ceramides, Chloroquine, Galactosylceramides, Glycosphingolipids, Monosaccharides.
- geographic : Senegal.
- chemistry : Porifera.
- drug effects : Plasmodium falciparum.
- drug therapy : Neoplasms.
- pathology : Neoplasms.
- Animals, Cell Line, Tumor, Drug Resistance, Female, Humans, Inhibitory Concentration 50, Mice.
Abstract
The marine sponge, Axinyssa djiferi, collected on mangrove tree roots in Senegal, was investigated for glycolipids. A mixture containing new glycosphingolipids, named axidjiferoside-A, -B and -C, accounted for 0.07% of sponge biomass (dry weight) and for 2.16% of total lipids. It showed a significant antimalarial activity, with a 50% inhibitory concentration (IC50) of 0.53 ± 0.2 μM against a chloroquine-resistant strain of Plasmodium falciparum. They were identified as homologous β-galactopyranosylceramides composed of 2-amino-(6E)-octadec-6-en-1,3,4-triol, and the major one, axidjiferoside-A (around 60%), contained 2-hydroxytetracosanoic acid. Cytotoxicity was studied in vitro on human cancer cell lines (multiple myeloma, colorectal adenocarcinoma, glioblastoma and two lung cancer NSCLC-N6 and A549). Results of this investigation showed that axidjiferosides are of interest, because they proved a good antiplasmodial activity, with only a low cytotoxicity against various human cell lines and no significant antitrypanosomal and antileishmanial activity. Thus, it seems that galactosylceramides with a β anomeric configuration may be suitable in searching for new antimalarial drugs.
DOI: 10.3390/md11041304
PubMed: 23595058
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xml:lang="en"><term>Animals</term><term>Antimalarials (administration & dosage)</term><term>Antimalarials (isolation & purification)</term><term>Antimalarials (pharmacology)</term><term>Cell Line, Tumor</term><term>Ceramides (administration & dosage)</term><term>Ceramides (isolation & purification)</term><term>Ceramides (pharmacology)</term><term>Chloroquine (pharmacology)</term><term>Drug Resistance</term><term>Female</term><term>Galactosylceramides (administration & dosage)</term><term>Galactosylceramides (isolation & purification)</term><term>Galactosylceramides (pharmacology)</term><term>Glycosphingolipids (administration & dosage)</term><term>Glycosphingolipids (isolation & purification)</term><term>Glycosphingolipids (pharmacology)</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Mice</term><term>Monosaccharides (administration & dosage)</term><term>Monosaccharides (isolation & purification)</term><term>Monosaccharides (pharmacology)</term><term>Neoplasms (drug therapy)</term><term>Neoplasms (pathology)</term><term>Plasmodium falciparum (drug effects)</term><term>Porifera (chemistry)</term><term>Senegal</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Antipaludiques (administration et posologie)</term><term>Antipaludiques (isolement et purification)</term><term>Antipaludiques (pharmacologie)</term><term>Chloroquine (pharmacologie)</term><term>Concentration inhibitrice 50</term><term>Céramides (administration et posologie)</term><term>Céramides (isolement et purification)</term><term>Céramides (pharmacologie)</term><term>Femelle</term><term>Galactosylcéramides (administration et posologie)</term><term>Galactosylcéramides (isolement et purification)</term><term>Galactosylcéramides (pharmacologie)</term><term>Glycosphingolipides (administration et posologie)</term><term>Glycosphingolipides (isolement et purification)</term><term>Glycosphingolipides (pharmacologie)</term><term>Humains</term><term>Lignée cellulaire tumorale</term><term>Oses (administration et posologie)</term><term>Oses (isolement et purification)</term><term>Oses (pharmacologie)</term><term>Plasmodium falciparum ()</term><term>Porifera ()</term><term>Résistance aux substances</term><term>Souris</term><term>Sénégal</term><term>Tumeurs (anatomopathologie)</term><term>Tumeurs (traitement médicamenteux)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="administration & dosage" xml:lang="en"><term>Antimalarials</term><term>Ceramides</term><term>Galactosylceramides</term><term>Glycosphingolipids</term><term>Monosaccharides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Antimalarials</term><term>Ceramides</term><term>Galactosylceramides</term><term>Glycosphingolipids</term><term>Monosaccharides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" 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xml:lang="fr"><term>Antipaludiques</term><term>Céramides</term><term>Galactosylcéramides</term><term>Glycosphingolipides</term><term>Oses</term></keywords><keywords scheme="MESH" qualifier="pathology" xml:lang="en"><term>Neoplasms</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antipaludiques</term><term>Chloroquine</term><term>Céramides</term><term>Galactosylcéramides</term><term>Glycosphingolipides</term><term>Oses</term></keywords><keywords scheme="MESH" qualifier="traitement médicamenteux" xml:lang="fr"><term>Tumeurs</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Cell Line, Tumor</term><term>Drug Resistance</term><term>Female</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Mice</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Concentration inhibitrice 50</term><term>Femelle</term><term>Humains</term><term>Lignée cellulaire tumorale</term><term>Plasmodium falciparum</term><term>Porifera</term><term>Résistance aux substances</term><term>Souris</term><term>Sénégal</term></keywords><keywords scheme="Wicri" type="geographic" xml:lang="fr"><term>Sénégal</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The marine sponge, Axinyssa djiferi, collected on mangrove tree roots in Senegal, was investigated for glycolipids. A mixture containing new glycosphingolipids, named axidjiferoside-A, -B and -C, accounted for 0.07% of sponge biomass (dry weight) and for 2.16% of total lipids. It showed a significant antimalarial activity, with a 50% inhibitory concentration (IC50) of 0.53 ± 0.2 μM against a chloroquine-resistant strain of Plasmodium falciparum. They were identified as homologous β-galactopyranosylceramides composed of 2-amino-(6E)-octadec-6-en-1,3,4-triol, and the major one, axidjiferoside-A (around 60%), contained 2-hydroxytetracosanoic acid. Cytotoxicity was studied in vitro on human cancer cell lines (multiple myeloma, colorectal adenocarcinoma, glioblastoma and two lung cancer NSCLC-N6 and A549). Results of this investigation showed that axidjiferosides are of interest, because they proved a good antiplasmodial activity, with only a low cytotoxicity against various human cell lines and no significant antitrypanosomal and antileishmanial activity. Thus, it seems that galactosylceramides with a β anomeric configuration may be suitable in searching for new antimalarial drugs.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">23595058</PMID><DateCompleted><Year>2014</Year><Month>01</Month><Day>16</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>13</Day></DateRevised><Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">1660-3397</ISSN><JournalIssue CitedMedium="Internet"><Volume>11</Volume><Issue>4</Issue><PubDate><Year>2013</Year><Month>Apr</Month><Day>17</Day></PubDate></JournalIssue><Title>Marine drugs</Title><ISOAbbreviation>Mar Drugs</ISOAbbreviation></Journal><ArticleTitle>Antimalarial activity of axidjiferosides, new β-galactosylceramides from the African sponge Axinyssa djiferi.</ArticleTitle><Pagination><MedlinePgn>1304-15</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.3390/md11041304</ELocationID><Abstract><AbstractText>The marine sponge, Axinyssa djiferi, collected on mangrove tree roots in Senegal, was investigated for glycolipids. A mixture containing new glycosphingolipids, named axidjiferoside-A, -B and -C, accounted for 0.07% of sponge biomass (dry weight) and for 2.16% of total lipids. It showed a significant antimalarial activity, with a 50% inhibitory concentration (IC50) of 0.53 ± 0.2 μM against a chloroquine-resistant strain of Plasmodium falciparum. They were identified as homologous β-galactopyranosylceramides composed of 2-amino-(6E)-octadec-6-en-1,3,4-triol, and the major one, axidjiferoside-A (around 60%), contained 2-hydroxytetracosanoic acid. Cytotoxicity was studied in vitro on human cancer cell lines (multiple myeloma, colorectal adenocarcinoma, glioblastoma and two lung cancer NSCLC-N6 and A549). Results of this investigation showed that axidjiferosides are of interest, because they proved a good antiplasmodial activity, with only a low cytotoxicity against various human cell lines and no significant antitrypanosomal and antileishmanial activity. Thus, it seems that galactosylceramides with a β anomeric configuration may be suitable in searching for new antimalarial drugs.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Farokhi</LastName><ForeName>Fereshteh</ForeName><Initials>F</Initials><AffiliationInfo><Affiliation>Faculté des Sciences pharmaceutiques et biologiques, LUNAM Université, Université de Nantes, Groupe Mer, Molécules, Santé-EA 2160, Institut Universitaire Mer et Littoral-FR CNRS 3473, Nantes, France. fereshteh.farokhi@univ-nantes.fr</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Grellier</LastName><ForeName>Philippe</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Clément</LastName><ForeName>Monique</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Roussakis</LastName><ForeName>Christos</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Loiseau</LastName><ForeName>Philippe M</ForeName><Initials>PM</Initials></Author><Author ValidYN="Y"><LastName>Genin-Seward</LastName><ForeName>Emilie</ForeName><Initials>E</Initials></Author><Author ValidYN="Y"><LastName>Kornprobst</LastName><ForeName>Jean-Michel</ForeName><Initials>JM</Initials></Author><Author ValidYN="Y"><LastName>Barnathan</LastName><ForeName>Gilles</ForeName><Initials>G</Initials></Author><Author ValidYN="Y"><LastName>Wielgosz-Collin</LastName><ForeName>Gaëtane</ForeName><Initials>G</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2013</Year><Month>04</Month><Day>17</Day></ArticleDate></Article><MedlineJournalInfo><Country>Switzerland</Country><MedlineTA>Mar Drugs</MedlineTA><NlmUniqueID>101213729</NlmUniqueID><ISSNLinking>1660-3397</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000962">Antimalarials</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D002518">Ceramides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005699">Galactosylceramides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D006028">Glycosphingolipids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009005">Monosaccharides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C511581">beta-galactosyl ceramide</NameOfSubstance></Chemical><Chemical><RegistryNumber>886U3H6UFF</RegistryNumber><NameOfSubstance UI="D002738">Chloroquine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000962" MajorTopicYN="N">Antimalarials</DescriptorName><QualifierName UI="Q000008" MajorTopicYN="N">administration & dosage</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045744" MajorTopicYN="N">Cell Line, Tumor</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002518" MajorTopicYN="N">Ceramides</DescriptorName><QualifierName UI="Q000008" MajorTopicYN="N">administration & dosage</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002738" MajorTopicYN="N">Chloroquine</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004351" MajorTopicYN="N">Drug Resistance</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005260" MajorTopicYN="N">Female</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005699" MajorTopicYN="N">Galactosylceramides</DescriptorName><QualifierName UI="Q000008" MajorTopicYN="N">administration & dosage</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006028" MajorTopicYN="N">Glycosphingolipids</DescriptorName><QualifierName UI="Q000008" MajorTopicYN="N">administration & dosage</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D020128" MajorTopicYN="N">Inhibitory Concentration 50</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D051379" MajorTopicYN="N">Mice</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009005" MajorTopicYN="N">Monosaccharides</DescriptorName><QualifierName UI="Q000008" MajorTopicYN="N">administration & dosage</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009369" MajorTopicYN="N">Neoplasms</DescriptorName><QualifierName UI="Q000188" MajorTopicYN="N">drug therapy</QualifierName><QualifierName UI="Q000473" 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