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Mar. Drugs 2013, 11(11), 4451-4463; doi:10.3390/md11114451

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

1
The NeaNat Group, Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, via D. Montesano 49, Napoli 80131, Italy
2
Department of Experimental Oncology, Istituto Nazionale Tumori Fondazione "G. Pascale", Via M. Semmola, Napoli 80131, Italy
*
Author to whom correspondence should be addressed.
Received: 27 September 2013 / Revised: 25 October 2013 / Accepted: 25 October 2013 / Published: 8 November 2013
(This article belongs to the Special Issue Marine Secondary Metabolites)
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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.
Keywords: Smenospongia aurea; marine natural products; peptide/polyketides hybrids; structure elucidation; antitumor activity Smenospongia aurea; marine natural products; peptide/polyketides hybrids; structure elucidation; antitumor activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Teta, R.; Irollo, E.; Della Sala, G.; Pirozzi, G.; Mangoni, A.; Costantino, V. 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. Mar. Drugs 2013, 11, 4451-4463.

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