Polytheonamides, unprecedented highly cytotoxic polypeptides from the marine sponge Theonella swinhoei 2. Structure elucidation

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Abstract

The structures of polytheonamides A–C were assigned to be linear 48-residue peptides with N-terminus blocked by a carbamoyl group mainly by interpretation of spectral data.

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    Here, we applied the cytotoxic peptide, polytheonamide B (pTB), among other membrane-targeting peptides to understand the dynamic elementary processes of vectorial insertion. The 48-residue pTB is a cytotoxin obtained from the marine sponge Theonella swinhoei (14–23). The potent cytotoxicity of pTB is related to its channel-forming activity across the target cell membrane by spontaneously inserting into the membrane (15,18).

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    Most notably, the cytotoxic membrane-spanning peptides the polytheonamides are posttranslationally tailored with 17 C-methylations at nearly all unactivated sp3 carbon centers (Freeman et al., 2012; Hamada et al., 2010). Isolated from the Japanese sponge Theonella swinhoei (Hamada, Sugawara, Matsunaga, & Fusetani, 1994a, 1994b) and produced by the uncultivated bacterial symbiont “Candidatus Entotheonella factor” (Wilson et al., 2014), polytheonamides were found to be synthesized, in part, by two B12-dependent rSAM C-methyltransferases encoded in their biosynthetic gene cluster (Freeman, Helf, Bhushan, Morinaka, & Piel, 2017). Much like polytheonamides, many putative natural product pathways discovered from either uncultivated or genetically intractable microbes ultimately require heterologous expression to probe the biosynthesis of the encoded metabolite in entirety.

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Bioactive Marine Metabolites. 56. Part 55: Fusetani, N.; Hamada, T.; Sugawara, T.; Matsunaga, S., a proceeding paper in this issue.

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