Chlorinated Thiazole-Containing Polyketide-Peptides from the Caribbean Sponge Smenospongia conulosa: Structure Elucidation on Microgram Scale

Studies of non-ribosomal peptide/polyketide (NRP/PK) hybrid compounds in the holobiome of the Caribbean marine sponge Smenospongia conulosa led to the isolation of two new chlorinated thiazole-containing metabolites, conulothiazoles A (5) and B (6), along with four NRP/PK hybrids previously isolated from a different Smenospongia species. Structural elucidation was accomplished on a few micrograms of pure compounds using extensive NMR and MS studies, whereas determination of the absolute configuration of the amino acid moiety was achieved by degradation and by high-resolution LC-Ms analysis using only 4 µg of each compound.

Conulothiazoles A and B are two new chlorinated non-ribosomal peptide/polyketide (NRP/PK) hybrids that were isolated from the Caribbean sponge Smenospongia conulosa. Structural elucidation was accomplished on a few micrograms of pure compounds using extensive NMR and MS studies and nanomol-scale chemical degradation studies.

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