RESUMEN
We investigated the three soft corals Sarcophyton stellatum, Capnella fungiformis and Lobophytum crassum and the sponge Pseudoceratina arabica, which have been collected at the coast of Madagascar. In addition to previously known marine natural products, S. stellatum provided the new (+)-enantiomer of the cembranoid (1E,3E,11E)-7,8-epoxycembra-1,3,11,15-tetraene (2). Capnella fungiformis afforded three new natural products, ethyl 5-[(1E,5Z)-2,6-dimethylocta-1,5,7-trienyl]furan-3-carboxylate (6), ethyl 5-[(1E,5E)-2,6-dimethylocta-1,5,7-trienyl]furan-3-carboxylate (7) and the diepoxyguaiane sesquiterpene oxyfungiformin (9a). The extracts of all three soft corals exhibited moderate activities against the malarial parasite Plasmodium falciparum. Extracts of the sponge Pseudoceratina arabica proved to be very active against a series of Gram-positive and Gram-negative bacteria.
Asunto(s)
Productos Biológicos/química , Productos Biológicos/aislamiento & purificación , Poríferos/química , Animales , Antozoos , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Antimaláricos/química , Antimaláricos/aislamiento & purificación , Antimaláricos/farmacología , Productos Biológicos/farmacología , Cristalografía por Rayos X , Madagascar , Modelos Moleculares , Estructura Molecular , Pruebas de Sensibilidad Parasitaria , Plasmodium falciparum/efectos de los fármacosRESUMEN
The crude extracts of the Madagascan soft corals Sinularia vanderlandi and Sinularia gravis (Alcyoniidae) showed activity against Plasmodium falciparum which led us to study their chemical constituents. The new cadinane-type sesquiterpenoid vanderlandin (1) has been obtained from S. vanderlandi along with 24-methylenecholesterol (2). Four new compounds, the spatane-type diterpenoid gravilin (3), the monoalkylmonoacylglycerol 4, the dihomoditerpenoid ketone 5, and isodecaryiol (9), along with the three known compounds (+)-(S)-geranyllinalool (6), (-)-(R)-nephthenol (7), and 11,12-epoxysarcophytol A (8) have been isolated from the methanol extract of S. gravis. The structures were elucidated based on extensive spectroscopic methods, in particular various 2D NMR techniques. The structure of isodecaryiol (9) including its absolute configuration could be confirmed by X-ray diffraction.
Asunto(s)
Antozoos/química , Antiprotozoarios/química , Sesquiterpenos/química , Animales , Antiprotozoarios/análisis , Antiprotozoarios/aislamiento & purificación , Madagascar , Modelos Moleculares , Sesquiterpenos/análisis , Sesquiterpenos/aislamiento & purificaciónRESUMEN
Eight species of brown algae (Phaeophyceae) from the coast of Madagascar have been investigated for their chemical constituents. Fucosterol (3) was obtained as the most abundant compound. The brown alga Sargassum ilicifolium was the source for the first isolation of the terpenoid C27-alcohol 1,1',2-trinorsqualenol (1) from marine sources. From S. incisifolium we isolated the highly unsaturated glycolipid 1-O-palmitoyl-2-O-stearidonoyl-3-O-ß-D-galactopyranosylglycerol (4) and we report the first full assignment of its (1)H and (13)C NMR data. Apo-9'-fucoxanthinone (8) along with 24-ketocholesterol (5), (22E)-3ß-hydroxycholesta-5,22-dien-24-one (6), and saringosterol (7) were obtained from Turbinaria ornata. The crude extracts of all eight species of brown algae exhibited a pronounced antimicrobial activity against the Gram-positive bacteria Bacillus cereus, Staphylococcus aureus, and Streptococcus pneumoniae.
RESUMEN
Several species of red algae (Rhodophyta) from the coastal regions of Madagascar have been investigated for their natural products. The most abundant compound was cholesterol (5) in combination with a series of oxidized congeners. The brominated indoles 1-3 along with the sesquiterpene debilone (4) have been isolated from Laurencia complanata. For the first time, debilone (4) has been obtained from a marine plant. From the methanol extract of Calloseris sp., we have achieved the second isolation of the unusual A-ring contracted steroids (-)-2-ethoxycarbonyl-2ß-hydroxy-A-nor-cholest-5-en-4-one (9) and phorbasterone B (10). The crude extracts of Laurencia complanata exhibited antimicrobial activity against Bacillus cereus, Staphylococcus aureus, Streptococcus pneumoniae, and Candida albicans.
Asunto(s)
Productos Biológicos/aislamiento & purificación , Rhodophyta/química , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Productos Biológicos/farmacología , Bacterias Gramnegativas/efectos de los fármacos , Laurencia/química , Madagascar , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad MicrobianaRESUMEN
Bioassay-guided fractionation of a marine extract from Trididemnum cyclops afforded the new lipopeptide 39-oxobistramide K (1) and the known bistramides A (2) and D (3). Structure elucidation of 1 was carried out by analysis of one- and two-dimensional NMR spectroscopy and HRMS data. Bistramides have been reported to exhibit antiproliferative activity in the nanomolar range against a number of tumor cell lines in vitro and in vivo. The isolate 1 was tested for antiproliferative activity against the A2780 cell line and exhibited an IC(50) value of 0.34 microM.