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

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- a...

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Bibliographic Details
Published in:Marine drugs 2013-11, Vol.11 (11), p.4451-4463
Main Authors: Teta, Roberta, Irollo, Elena, Della Sala, Gerardo, Pirozzi, Giuseppe, Mangoni, Alfonso, Costantino, Valeria
Format: Article
Language:English
Subjects:
Animals
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
antitumor activity
Base Sequence
Caribbean Region
Cell Line, Tumor
Cyanobacteria - genetics
Cyanobacteria - metabolism
Drug Screening Assays, Antitumor - methods
Halogenation
Humans
marine natural products
Molecular Sequence Data
peptide/polyketides hybrids
Peptides - chemistry
Peptides - pharmacology
Polyketides - chemistry
Polyketides - pharmacology
Porifera - chemistry
Porifera - microbiology
RNA, Ribosomal, 16S - genetics
Smenospongia aurea
structure elucidation
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Summary: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.
ISSN:1660-3397
1660-3397
DOI:10.3390/md11114451