Smenamides A and B, chlorinated peptide/polyketide hybrids containing a dolapyrrolidinone unit from the Caribbean sponge Smenospongia aurea. Evaluation of their role as leads in antitumor drug research

Roberta Teta, Elena Irollo, Gerardo Della Sala, Giuseppe Pirozzi, Alfonso Mangoni, Valeria Costantino

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

An in-depth study of the secondary metabolites contained in the Caribbean sponge Smenospongia aurea led to the isolation of smenamide A (1) and B (2), hybrid peptide/polyketide compounds containing a dolapyrrolidinone unit. Their structures were elucidated using high-resolution ESI-MS/MS and homo- and heteronuclear 2D NMR experiments. Structures of smenamides suggested that they are products of the cyanobacterial metabolism, and 16S rRNA metagenomic analysis detected Synechococcus spongiarum as the only cyanobacterium present in S. aurea. Smenamides showed potent cytotoxic activity at nanomolar levels on lung cancer Calu-1 cells, which for compound 1 is exerted through a clear pro-apoptotic mechanism. This makes smenamides promising leads for antitumor drug design.

Original languageEnglish
Pages (from-to)4451-4463
Number of pages13
JournalMarine Drugs
Volume11
Issue number11
DOIs
Publication statusPublished - Nov 2013

Fingerprint

Biomolecular Nuclear Magnetic Resonance
Synechococcus
Polyketides
Metagenomics
Drug Design
Cyanobacteria
Porifera
Antineoplastic Agents
Lung Neoplasms
Research
arginyl-leucyl-cysteinyl-arginyl-isoleucyl-valyl-valyl-isoleucyl-arginyl-valyl-cysteinyl-arginyl-aspartyl-aspartyl-aspartyl-aspartyl-glutamyl-glutamic acid (3-11)disulfide
peptide B

Keywords

  • Antitumor activity
  • Marine natural products
  • Peptide/polyketides hybrids
  • Smenospongia aurea
  • Structure elucidation

ASJC Scopus subject areas

  • Drug Discovery

Cite this

Smenamides A and B, chlorinated peptide/polyketide hybrids containing a dolapyrrolidinone unit from the Caribbean sponge Smenospongia aurea. Evaluation of their role as leads in antitumor drug research. / Teta, Roberta; Irollo, Elena; Della Sala, Gerardo; Pirozzi, Giuseppe; Mangoni, Alfonso; Costantino, Valeria.

In: Marine Drugs, Vol. 11, No. 11, 11.2013, p. 4451-4463.

Research output: Contribution to journalArticle

Teta, Roberta ; Irollo, Elena ; Della Sala, Gerardo ; Pirozzi, Giuseppe ; Mangoni, Alfonso ; Costantino, Valeria. / Smenamides A and B, chlorinated peptide/polyketide hybrids containing a dolapyrrolidinone unit from the Caribbean sponge Smenospongia aurea. Evaluation of their role as leads in antitumor drug research. In: Marine Drugs. 2013 ; Vol. 11, No. 11. pp. 4451-4463.
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