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

Research output: Contribution to journalArticle

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 languageEnglish
Article number618
JournalMarine Drugs
Volume17
Issue number11
DOIs
Publication statusPublished - 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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  • Cite this

    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