Bioactive Alkaloids from the Tropical Marine Sponge Axinella carteri

Abstract

Analysis of the tropical marine sponge Axinella carteri afforded six unusual alkaloids, including the new brominated guanidine derivative 3-bromo-hymenialdisine. The structure elucidation of the new alkaloid is described. The alkaloid patterns of sponges collected in Indonesia or in the Philippines were shown to be qualitatively identical suggesting de novo synthesis by the sponge or by endosymbiontic microorganisms rather than uptake by filterfeeding. All alkaloids were screened for insecticidal activity as well as for cytotoxicity. The guanidine alkaloids hymenialdisine and debromohymenialdisine exhibited insecticidal activity towards neonate larvae of the polyphagous pest insect Spodoptera littoralis (LD50s of 88 and 125 ppm, respectively), when incorporated into artificial diet and offered to the larvae in a chronic feeding bioassay. The remaining alkaloids, including the new compound, were inactive in this bioassay. Cytotoxicity was studied in vitro using L5178y mouse lymphoma cells. Debromohymenialdisine was again the most active compound (ED50 1.8 μg/ml) followed by hymenialdisine and 3-bromohymenialdisine, which were essentially equitoxic and exhibited ED50s of 3.9 μg/ml in both cases. The remaining alkaloids were inactive against this cell line

Spatial Variability in Secondary Metabolites of the Indo-Pacific Sponge Stylissa massa

“…Some studies have observed a low variability in sponge metabolite concentrations. The brominated pyrrole alkaloids hymenialdisine, debromohymenialdisine, dibromophakellin, and 3-bromohymenialdisin occur in similar concentrations within specimens of the sponge Axinella carteri, collected from sites over 2000 km (Supriyono et al, 1995). In contrast, a recent study on bromotyrosine derivatives from Aplysina fulva demonstrated chemical variability among specimens collected in multiple locations in Brazil and the United States (Nunez et al, 2008).…”

Antiplasmodial and Cytotoxic Metabolites from the Maltese SpongeAgelas oroides(1)

“…The most abundant isolate found in the dichloromethane solubles of the sponge was oroidin (1) (6, ii). Since the original isolation of oroidin, a number of research groups have reported its presence in samples they have investigated (12)(13)(14). Walker and colleagues proved the structure of 1 by single crystal X-ray analysis (12), but no reference NMR or mass spectral data were given.…”

Quorum Sensing Inhibitors from the Sea Discovered Using Bacterial N-acyl-homoserine Lactone-Based Biosensors

“…Five compounds ( 43 – 47 ) (Figure 9), deriving from various sponges were able to inhibit QS of C. violaceum CV017. Hymenialdisin ( 43 ), an alkaloid originally isolated from the sponge Axinella verrucosa [98] inhibited QS dependent luminescence in reporter strain pSB401 and pSB1075 induced by 3-oxo-C 6 -HSL and 3-oxo-C 12 -HSL, respectively. Several other alkaloids, ageliferin ( 44 ) isolated from Agelas conifer , mauritamide B ( 45 ) isolated from A. nakamurai , midpacamide ( 46 ), isolated from A. mauritama [99] and 4-(4,5-dibromo-1-methyl-1 H -pyrrole-2-carboxamido) butanoic acid ( 47 ) isolated from Agelas sp.…”