Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti

Natural product discovery by isolation and structure elucidation is a laborious task often requiring ample quantities of biological starting material and frequently resulting in the rediscovery of previously known compounds. However, peptides are a compound class amenable to an alternative genomic,...

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Bibliographic Details
Main Authors: Karin Steffen (5031989), Quentin Laborde (11341406), Sunithi Gunasekera (1364190), Colton D. Payne (6635933), K. Johan Rosengren (1346457), Ana Riesgo (276019), Ulf Göransson (1364202), Paco Cárdenas (11804556)
Format: Other Non-Article Part of Journal/Newspaper
Language:unknown
Published: 1753
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Online Access:https://doi.org/10.1021/acs.jnatprod.1c00938.s001
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Summary:Natural product discovery by isolation and structure elucidation is a laborious task often requiring ample quantities of biological starting material and frequently resulting in the rediscovery of previously known compounds. However, peptides are a compound class amenable to an alternative genomic, transcriptomic, and in silico discovery route by similarity searches of known peptide sequences against sequencing data. Based on the sequences of barrettides A and B, we identified five new barrettide sequences (barrettides C–G) predicted from the North Atlantic deep-sea demosponge Geodia barretti (Geodiidae). We synthesized, folded, and investigated one of the newly described barrettides, barrettide C (NVVPCFCVED­ETSGAKTCIP­DNCDAS­RGTNP, disulfide connectivity I–IV, II–III). Co-elution experiments of synthetic and sponge-derived barrettide C confirmed its native conformation. NMR spectroscopy and the anti-biofouling activity on larval settlement of the bay barnacle Amphibalanus improvisus (IC 50 0.64 μM) show that barrettide C is highly similar to barrettides A and B in both structure and function. Several lines of evidence suggest that barrettides are produced by the sponge itself and not one of its microbial symbionts.