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Phytochemistry ; 124: 79-85, 2016 Apr.
Article in English | MEDLINE | ID: mdl-26743853

ABSTRACT

Eighteen natural products sourced from Australian micro- or macro-fungi were screened for antibacterial and antifungal activity. This focused library was comprised of caprolactams, polyamines, quinones, and polyketides, with additional large-scale isolation studies undertaken in order to resupply previously identified compounds. Chemical investigations of the re-fermented culture from the endophytic fungus Pestalotiopsis sp. yielded three caprolactam analogues, pestalactams D-F, along with larger quantities of the known metabolite pestalactam A, which was methylated using diazomethane to yield 4-O-methylpestalactam A. The chemical structures of the previously undescribed fungal metabolites were determined by analysis of 1D/2D NMR and MS data. The structure of 4-O-methylpestalactam A was confirmed following single crystal X-ray diffraction analysis. The antibacterial and antifungal activity of all compounds was assessed, which identified three compounds, (1S,3R)-austrocortirubin, (1S,3S)-austrocortirubin, and 1-deoxyaustrocortirubin with mild activity (100 µM) against Gram-positive isolates and one compound, 2-hydroxy-6-methyl-8-methoxy-9-oxo-9H-xanthene-1-carboxylic acid, with activity against Cryptococcus neoformans and Cryptococcus gattii at 50 µM.


Subject(s)
Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Antifungal Agents/isolation & purification , Antifungal Agents/pharmacology , Biological Products/isolation & purification , Biological Products/pharmacology , Caprolactam , Xylariales/chemistry , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemistry , Australia , Biological Products/chemistry , Caprolactam/analogs & derivatives , Caprolactam/chemistry , Caprolactam/isolation & purification , Caprolactam/pharmacology , Cryptococcus neoformans/drug effects , Crystallography, X-Ray , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular
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