Three new pentacyclic alkaloids were isolated from different chromotypes of the western Mediterranean ascidian Cystodytes dellechiajei. The purple color morph collected in Catalonia contained the known compounds kuanoniamine D (1), shermilamine B (2), N-deacetylkuanoniamine D (3), and styelsamine C (4) and a new alkaloid named N-deacetylshermilamine B (5). The green color morph collected in the Balearic Islands contained the known compounds 11-hydroxyascididemin (6) and 8,9-dihydro-11-hydroxyascididemin (7) and two new alkaloids named cystodimine A (8) and cystodimine B (9). The blue color morph collected in Catalonia yielded the known compound ascididemin (10). The structures of all compounds were elucidated on the basis of spectroscopic data, mainly 1D and 2D NMR data. The antimicrobial potential of the pyridoacridine alkaloids isolated from each color morph was evaluated and compared.
Several studies report temporal, geographical, and intra-individual variation in sponge metabolite yields. However, the internal and/or external factors that regulate the metabolite production remain poorly understood. Dysidea avara is a demosponge that produces sesquiterpenoids (avarol and derivatives) with interesting medical properties, which has prompted addressed studies to obtain enough amounts of these metabolites for research on drug discovery. Within this framework, specimens of Dysidea avara from apopulation of the Northwest Mediterranean were sampled and their secondary metabolites quantified to assess their variability and the possible relationship with external (seasonality, interactions with neighbors) and internal (reproductive stages) factors. The results show a variation of the amount of both avarol and its monoacetate derivative with time, with no clear relationship with seawater temperature. A trade-off with sponge reproduction was not found either. However, our results showed for the first time that sponges are able to increase production or accumulation of secondary metabolites in their peripheral zone depending on the nature of their neighbors. This finding could explain part of the high variability in the amount of secondary metabolites usually found in chemical ecology studies on sponges and opens new biotechnological approaches to enhance the metabolite yield in sponge cultures.
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