Abstract
Caribbean sponges of the genus Smenospongia are a prolific source of chlorinated secondary metabolites. The use of molecular networking as a powerful dereplication tool revealed in the metabolome of S. aurea two new members of the smenamide family, namely smenamide F (1) and G (2). The structure of smenamide F (1) and G (2) 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 (1). Smenamide F (1) and G (2) 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.
Highlights
Marine organisms are a source of compounds with enormous chemical diversity, which, in turn, translates to a wide variety of biological activities
Paper, we we report report on on the the use use of of aa molecular molecular networking networking dereplication dereplication strategy strategy which which resulted in the rapid detection from extracts of aurea of two new members of the smenamide family, resulted in the rapid detection from extracts of S. aurea of two new members of the smenamide family, smenamide smenamide F
The use of molecular networking as a dereplication strategy allowed for the rapid detection of two new members of the smenamide family of compounds, smenamide F (1) and G (2)
Summary
Marine organisms are a source of compounds with enormous chemical diversity, which, in turn, translates to a wide variety of biological activities. Many marine natural products show unusual and unique chemical structures, often containing halogen atoms. Halogenated natural products are widely present in nature. More than 5000 compounds are reported in the literature and most of them have a marine origin [1,2]. Our research program, aimed at discovering new bioactive compounds from marine organisms, focused in recent years on the metabolome of Caribbean sponges of the genus Smenospongia, which have proven to be very rich in new chlorinated secondary metabolites. Among them are smenamides [3], smenothiazoles [4] and conulothiazoles [5], belonging to the hybrid peptide/polyketide chlorinated class of compounds; smenolactones, four chlorinated compounds with a polyketide structure [6]; and smenopyrone, a biogenetically different compound with a polypropionate structure containing two γ-pyrone rings [7]
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