Bromopyrrole carboxamide biosynthetic products from the Caribbean sponge Agelas dispar.

Two new bromopyrrole alkaloids, dispyrin (6) and dibromoagelaspongin methyl ether (12), were isolated from the Caribbean sponge Agelas dispar, collected near the Venezuelan island La Blanquilla, and their structures were elucidated from spectroscopic data analysis. Dispyrin (6) contains a novel bromopyrrole tyramine motif that has no precedent in marine natural products chemistry and represents a notable variation from the oroidin class compounds consistently produced by species of Agelas in general. Compounds isolated from Caribbean Agelas species were found to possess a unique biogeographical bromination trend.