A detailed analysis of the chemical constituents of a specimen of Agelas wiedenmayeri (Alcolado, 1984) was performed. Four brominated alkaloids (1−4) were isolated and one was identified as a new bromopyrrole metabolite. The structure of the new compound, 1, was assigned using spectroscopic methods. Compounds 2 and 3, which are the major brominated metabolites, have been previously described from other Agelas sponges. The new compound, 1, may be a biosynthetic precursor for oroidin-like derivatives.Bromopyrrole-derived alkaloids are well-known in marine sponges of the genus Agelas. 1 In our search for bioactive substances from marine organisms, a series of brominated pyrrole alkaloids have been isolated from a specimen of the sponge Agelas wiedenmayeri (Alcolado, 1984) collected off the coast of the Florida Keys, FL. Examination of the methanol/dichloromethane extract of this sponge resulted in isolation of the known alkaloids 4,5-dibromopyrrole-2-carboxylic acid 2, oroidin 3, and bromoageliferin 4 as well as of the new bromopyrrole-derived alkaloid, 4-bromopyrrole-2-carboxyhomoarginine 1 (5 mg, 0.005% of dry weight) (Figure 1). In this communication we describe the isolation and structural elucidation of the new bromopyrrole alkaloid 1. To the best of our knowledge, this is the first report on the chemistry of Agelas wiedenmayeri.The marine sponge Agelas wiedenmayeri (Alcolado, 1984)
A detailed analysis of the chemical constituents of a Caribbean specimen of Aiolochroia crassa was performed. Five brominated products ( 1 -5 ) were isolated and one of these was a new bromotyrosine metabolite. The structure of the new compound 1 has been established from spectral studies. Compounds 1 and 2, which are the major brominated metabolites and have not been previously identified in any Aiolochroia species, could be usefully employed as chemotaxonomic markers.
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