Cavomycins A−C, Linear Oligomer Depsipeptides from an Annelid-Associated Streptomyces cavourensis

Abstract

Three unique linear oligomeric depsipeptides, designated as cavomycins A−C (1−3), were identified from Streptomyces cavourensis, a gut bacterium associated with the annelid Paraleonnates uschakovi. The structures of these depsipeptides were determined through a combination of spectroscopic methods and chemical derivatization techniques, including methanolysis, the modified Moshers method, advanced Marfeys methods, and phenylglycine methyl ester derivatization. The unique dipeptidyl residue arrangements in compounds 1−3 indicate that they are not degradation products of valinomycin. Compound 2 and its methylation derivative 2a exhibited antiproliferative activity against PANC-1 pancreatic cancer cells with IC50 values of 1.2 and 1.7 μM, respectively.