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.
Highlights
Malaria caused by the Anopheles mosquito-transmitted parasite, Plasmodium, is one of the leading causes of mortality and morbidity in more than 100 tropical and subtropical countries of the world, P. falciparum remaining the most dangerous species and causing the most lethal form of malaria [1,2].In spite of some important studies towards the development of an efficient vaccine, there is only a limited number of drugs in widespread use for the treatment of malaria [3,4]
The specimens of the Senegalese sponge, Axinyssa djiferi [25,26], were extracted with dichloromethane-methanol mixtures, and the crude lipids were fractionated on a silica gel column, eluted with chloroform, acetone and, methanol
The chemical structure and composition of axidjiferosides were obtained by electrospray ionization mass spectrometry (ESI-MS) and NMR studies of the peracetylated GL and by controlled chemical degradation
Summary
Malaria caused by the Anopheles mosquito-transmitted parasite, Plasmodium, is one of the leading causes of mortality and morbidity in more than 100 tropical and subtropical countries of the world, P. falciparum remaining the most dangerous species and causing the most lethal form of malaria [1,2]. The new breakthrough in malaria treatment could come with the development of a marine lead compound, taking into account the great potential of marine invertebrates to produce a large array of biological-active metabolites [10,11]. The latter reviews on marine antimalarials published in 2009 did not mention any glycolipid (GL), and it was the same from any other natural sources, including plants [9]. In a previous work on the Senegalese sponge, Axinyssa djiferi [25], we isolated a GSL complex mixture, which included nine principal closely related compounds, named axidjiferosides, responsible for an interesting antimalarial activity [26].
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