Bioactive bromopyrrole metabolites from the Caribbean sponge Agelas conifera

The Journal of Organic Chemistry
1991.0

Abstract

During studies of bioactive marine natural products we found that extracts of some Caribbean Agelas sponges possessed activity in antiviral and antibacterial assays.2 Subsequent exhaustive attempts to isolate the active components resulted in the isolation of numerous biologically active compounds. Reported here are the structures and biological activities of seven new bromopyrrole metabolites isolated as acetate salts 1 and 3-8, along with sceptrin diacetate (2),9 from the Caribbean sponges Agelas conifera and Agelas n. sp. (family Agelasidae, order Axinellidas). Biologically active extracts of the Caribbean sponge Agelas conifera have yielded, in exhaustive studies, the diacetate salts of seven new bromopyrroles (1,3-8), as well as that of the known debromooroidin dimer sceptrin (2). These compounds were found to be antiviral and antibacterial and were active in barnacle settlement and biochemical prophage induction assays. The structures assigned were based on spectroscopic comparisons to sceptrin and two-dimensional NMR data. Synthetic bromopyrroles were used to verify bromine substitution patterns. The oxysceptrins (4,5) are characterized by their aminoimidazolinone group, the ageliferins (6-8) by a unique cyclohexene-based skeleton.

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