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Two new cyclic depsipeptides named swinhopeptolides A ( 1 ) and B ( 2 ) have been isolated from the marine sponge Theonella swinhoei cf. verrucosa , collected from Papua New Guinea. They each contain 11 diverse amino acid residues and 13-carbon polyketide moieties attached at the N -terminus. Compounds 1 and 2 each exist as two conformers in DMSO- d  6 due to cis / trans isomerism of the proline residue, and their structures were successfully assigned by extensive NMR analyses complemented by chemical degradation and derivatization studies. Swinhopeptolide B ( 2 ) contains a previously undescribed 2,6,8-trimethyldeca-(2 E ,4 E ,6 E )-trienoic acid moiety N -linked to a terminal serine residue. Swinhopeptolides A ( 1 ) and B ( 2 ) showed significant inhibition of the Ras/Raf signaling pathway with IC 50 values of 5.8 and 8.5 μM, respectively.

Swinhopeptolides A and B: Cyclic Depsipeptides from the Sponge Theonella swinhoei That Inhibit Ras/Raf Interaction