Fast detection of two smenamide family members using molecular networking

Alessia Caso; Germana Esposito; Gerardo Della Sala; Joseph R. Pawlik; Roberta Teta; Alfonso Mangoni; Valeria Costantino

doi:10.3390/md17110618

Fast detection of two smenamide family members using molecular networking

Alessia Caso, Germana Esposito, Gerardo Della Sala, Joseph R. Pawlik, Roberta Teta, Alfonso Mangoni, Valeria Costantino

IRCCS Centro di Riferimento Oncologico della Basilicata (CROB)

Research output: Contribution to journal › Article

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.

Original language	English
Article number	618
Journal	Marine Drugs
Volume	17
Issue number	11
DOIs	https://doi.org/10.3390/md17110618
Publication status	Published - Oct 30 2019

Keywords

Anti-tumor lead molecules
Conformational analysis
Marine natural products
Smenamides
Smenospongia aurea
Solid tumor cell lines
Structure elucidation

ASJC Scopus subject areas

Drug Discovery

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10.3390/md17110618

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Caso, A., Esposito, G., Sala, G. D., Pawlik, J. R., Teta, R., Mangoni, A., & Costantino, V. (2019). Fast detection of two smenamide family members using molecular networking. Marine Drugs, 17(11), [618]. https://doi.org/10.3390/md17110618

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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.",

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AU - Caso, Alessia

AU - Esposito, Germana

AU - Sala, Gerardo Della

AU - Pawlik, Joseph R.

AU - Teta, Roberta

AU - Mangoni, Alfonso

AU - Costantino, Valeria

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N2 - 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.

AB - 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.

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