Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 6, Issue 11, Pages 1762-1774Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9qo00074g
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Funding
- Regione Campania, POR Campania FESR 2014-2020, O.S. 1.2, Project Campania Oncoterapie [B61G18000470007]
- US-NSF Biological Oceanography Programme [OCE 1029515]
- Institutional Development Award (IDeA) Network for Biomedical Research Excellence from the National Institute of General Medical Sciences of the National Institutes of Health [P20GM103430]
- National Science Foundation EPSCoR Cooperative Agreement [EPS-1004057]
- American Society of Pharmacognosy Starter Grant
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The bloom-forming cyanobacterium Trichodesmium sp. has been recently shown to produce some of the chlorinated peptides/polyketides previously isolated from the marine sponge Smenospongia aurea. A comparative analysis of extracts from S. aurea and Trichodesmium sp. was performed using tandem mass spectrometry-based molecular networking. The analysis, specifically targeted to chlorinated metabolites, showed that many of them are common to the two organisms, but also that some general differences exist between the two metabolomes. Following this analysis, six new chlorinated metabolites were isolated and their structures were elucidated: four polyketides, smenolactones A-D (1-4) fromS. aurea, and two new conulothiazole analogues, isoconulothiazole B (5) and conulothiazole C (6) from Trichodesmium sp. The absolute configuration of smenolactone C (3) was determined by taking advantage of the conformational rigidity of open 1,3-disubstituted alkyl chains. The antiproliferative activity of smenolactones was evaluated on three tumor cell lines, and they were active at low-micromolar or submicromolar concentrations.
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