Biologically active metabolites produced by the basidiomycete Quambalaria cyanescens.
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.
Institute of Microbiology of the ASCR, v.v.i., Prague, Czech Republic.
Eva
E
Stodůlková
Department of Inorganic Chemistry, Faculty of Science, Charles University, Prague, Czech Republic.
Ivana
I
Císařová
Institute of Microbiology of the ASCR, v.v.i., Prague, Czech Republic.
Miroslav
M
Kolařík
Institute of Microbiology of the ASCR, v.v.i., Prague, Czech Republic.
Milada
M
Chudíčková
Institute of Microbiology of the ASCR, v.v.i., Prague, Czech Republic.
Petr
P
Novák
Institute of Microbiology of the ASCR, v.v.i., Prague, Czech Republic.
Petr
P
Man
Institute of Microbiology of the ASCR, v.v.i., Prague, Czech Republic.
Marek
M
Kuzma
Department of Cell Biology, Faculty of Science, Charles University, Praha, Czech Republic.
Barbora
B
Pavlů
Department of Cell Biology, Faculty of Science, Charles University, Praha, Czech Republic.
Jan
J
Černý
Institute of Microbiology of the ASCR, v.v.i., Prague, Czech Republic.
Miroslav
M
Flieger
D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D001487:Basidiomycota / Q000378:metabolism*; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism* / Q000494:pharmacology; D002460:Cell Line; D005285:Fermentation; D006801:Humans; D008826:Microbial Sensitivity Tests
D000890:Anti-Infective Agents; D001688:Biological Products