Cyclopsammocinamides A and B, Enantiomeric Cyclic Peptides of Cyclocinamide A, from the Marine Sponge Psammocinia sp.

Abstract

LC-MS and molecular networking analyses of the extract of the marine sponge Psammocinia sp. indicated the presence of two new compounds with multiple halogens. LC-MS-guided isolation yielded cyclic peptides, cyclopsammocinamides A (1) and B (2), in an enantiomeric relationship to cyclocinamide A (3). Planar structures of 1 and 2 were elucidated by NMR and mass spectroscopic analyses and the absolute configurations of the amino acid residues were determined using Marfey’s method with their acid hydrolysates. The sponge extract exhibited cytotoxicity and the bioassay-guided isolation afforded a dimeric dilac-tone macrolide, swinholide A, as the cytotoxic compound.