Biologically Active Metabolites Produced by the Basidiomycete Quambalaria cyanescens |
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Authors: | Eva Stod?lková Ivana Císa?ová Miroslav Kola?ík Milada Chudí?ková Petr Novák Petr Man Marek Kuzma Barbora Pavl? Jan ?erny Miroslav Flieger |
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Affiliation: | 1Institute of Microbiology of the ASCR, v.v.i., Prague, Czech Republic;2Department of Inorganic Chemistry, Faculty of Science, Charles University, Prague, Czech Republic;3Department of Cell Biology, Faculty of Science, Charles University, Praha, Czech Republic;Umeå Plant Science Centre, Umeå University, SWEDEN |
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Abstract: | Four strains of the fungus Quambalaria cyanescens (Basidiomycota: Microstromatales), were used for the determination of secondary metabolites production and their antimicrobial and biological activities. A new naphthoquinone named quambalarine A, (S)-(+)-3-(5-ethyl-tetrahydrofuran-2-yliden)-5,7,8-trihydroxy-2-oxo-1,4-naphthoquinone (1), together with two known naphthoquinones, 3-hexanoyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone (named here as quambalarine B, 2) and mompain, 2,5,7,8-tetrahydroxy-1,4-naphthoquinone (3) were isolated. Their structures were determined by single-crystal X-ray diffraction crystallography, NMR and MS spectrometry. Quambalarine A (1) had a broad antifungal and antibacterial activity and is able inhibit growth of human pathogenic fungus Aspergillus fumigatus and fungi co-occurring with Q. cyanescens in bark beetle galleries including insect pathogenic species Beauveria bassiana. Quambalarine B (2) was active against several fungi and mompain mainly against bacteria. The biological activity against human-derived cell lines was selective towards mitochondria (2 and 3); after long-term incubation with 2, mitochondria were undetectable using a mitochondrial probe. A similar effect on mitochondria was observed also for environmental competitors of Q. cyanescens from the genus Geosmithia. |
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