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

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

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Received: 27 September 2013; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA 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. Marine Drugs. 2013; 11(11):4451-4463.

Chicago/Turabian Style

Teta, Roberta; Irollo, Elena; Della Sala, Gerardo; Pirozzi, Giuseppe; Mangoni, Alfonso; Costantino, Valeria. 2013. "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 11, no. 11: 4451-4463.


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