Preprint Article Version 1 This version is not peer-reviewed

Fast Detection of Two Smenamide Family-Members Using Molecular Networking

Version 1 : Received: 7 October 2019 / Approved: 8 October 2019 / Online: 8 October 2019 (11:08:05 CEST)

How to cite: Caso, A.; Esposito, G.; Della Sala, G.; Pawlik, J.R.; Teta, R.; Mangoni, A.; Costantino, V. Fast Detection of Two Smenamide Family-Members Using Molecular Networking. Preprints 2019, 2019100091 (doi: 10.20944/preprints201910.0091.v1). Caso, A.; Esposito, G.; Della Sala, G.; Pawlik, J.R.; Teta, R.; Mangoni, A.; Costantino, V. Fast Detection of Two Smenamide Family-Members Using Molecular Networking. Preprints 2019, 2019100091 (doi: 10.20944/preprints201910.0091.v1).

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 the presence in the metabolome of S. aurea of 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.

Subject Areas

smenospongia aurea; marine natural products; structure elucidation; anti-tumor lead molecules; smenamides; solid tumor cell lines; conformational analysis

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