Abstract
Muscotoxins are cyanobacterial cyclic lipopeptides with potential applications in biomedicine and biotechnology. In this study, Desmonostoc muscorum CCALA125 strain extracts were enriched by polymeric resin treatment, and subjected to HPCCC affording three cyclic lipopeptides (1–3), which were further repurified by semi-preparative HPLC, affording 1, 2, and 3, with a purity of 86%, 92%, and 90%, respectively. The chemical identities of 2–3 were determined as muscotoxins A and B, respectively, by comparison with previously reported ESI-HRMS/MS data, whereas 1 was determined as a novel muscotoxin variant (muscotoxin C) using NMR and ESI-HRMS/MS data. Owing to the high yield (50 mg), compound 2 was broadly screened for its antimicrobial potential exhibiting a strong antifungal activity against Alternaria alternata, Monographella cucumerina, and Aspergillus fumigatus, with minimum inhibitory concentration (MIC) values of 0.58, 2.34, and 2.34 µg/mL; respectively, and weak antibacterial activity against Bacillus subtilis with a MIC value of 37.5 µg/mL. Compounds 1 and 3 were tested only against the plant pathogenic fungus Sclerotinia sclerotiorum due to their low yield, displaying a moderate antifungal activity. The developed chromatographic method proved to be an efficient tool for obtaining muscotoxins with potent antifungal properties.
Highlights
Cyanobacteria are Gram-negative photosynthetic microorganisms that have gained attention as a source of potential therapeutically useful compounds [1]. One group of these compounds is represented by cyclic lipopeptides (CLPs), which have been found to comprise up to 14 amino
CLPs are biosynthesized by multifunctional protein complexes called polyketide synthases (PKS) and non-ribosomal peptide synthetases (NRPS) [2]
D. muscorum CCALA125 (a,d), the muscotoxin-enriched extract obtained by consecutive treatment on muscorum CCALA125 (a,d), the muscotoxin-enriched extract obtained by consecutive treatment on Amberlite XAD-16 (b,e) and Amberlite XAD-7 (c,f) adsorption resins
Summary
Cyanobacteria are Gram-negative photosynthetic microorganisms that have gained attention as a source of potential therapeutically useful compounds [1] One group of these compounds is represented by cyclic lipopeptides (CLPs), which have been found to comprise up to 14 amino. CLPs are biosynthesized by multifunctional protein complexes called polyketide synthases (PKS) and non-ribosomal peptide synthetases (NRPS) [2]. In these structures, a modified fatty acid tail is linked to the peptidic macrocycle leading to the formation of CLPs. The pharmacological potential of CLPs is represented by their antifungal [3], antibiotic [4], cytotoxic [5], and antiproliferative activities [6,7]. Caspofungin, cyclosporine A, and daptomycin are three successful examples of CLPs that have been approved for clinical use as antifungal [8], immunosuppressant [9], and antibiotic agents in humans [10], respectively
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