A joint molecular networking study of a Smenospongia sponge and a cyanobacterial bloom revealed new antiproliferative chlorinated polyketides

Roberta Teta, Gerardo Della Sala, Germana Esposito, Christopher W Via, Carmela Mazzoccoli, Claudia Piccoli, Matthew J Bertin, Valeria Costantino, Alfonso Mangoni

Research output: Contribution to journalArticle

Abstract

The bloom-forming cyanobacteria Trichodesmium sp. have 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 elucidated: four polyketides, smenolactones A-D (1-4) from S. 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 sub-micromolar concentrations.

Original languageEnglish
Pages (from-to)1762-1774
Number of pages13
JournalOrganic Chemistry Frontiers
Volume6
Issue number11
DOIs
Publication statusPublished - Jun 7 2019

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