Fast Detection of Two Smenamide Family Members Using Molecular Networking

Abstract

Caribbean sponges of the genus <i>Smenospongia</i> are a prolific source of chlorinated secondary metabolites. The use of molecular networking as a powerful dereplication tool revealed in the metabolome of <i>S. aurea</i> two new members of the smenamide family, namely smenamide F (<b>1</b>) and G (<b>2</b>). The structure of smenamide F (<b>1</b>) and G (<b>2</b>) was determined by spectroscopic analysis (NMR, MS, ECD). The relative and the absolute configuration at C-13, C-15, and C-16 was determined on the basis of the conformational rigidity of a 1,3-disubstituted alkyl chain system (i.e., the C-12/C-18 segment of compound (<b>1</b>). Smenamide F (<b>1</b>) and G (<b>2</b>) were shown to exert a selective moderate antiproliferative activity against cancer cell lines MCF-7 and MDA-MB-231, while being inactive against MG-63.