Isochromenones, isobenzofuranone, and tetrahydronaphthalenes produced by Paraphoma radicina, a fungus isolated from a freshwater habitat.
Six isochromenones (1-6), clearanols F (5) and G (6), one isobenzofuranone (7), and two tetrahydronaphthalene derivatives (8 and radinaphthalenone (9)), were isolated and identified from a culture of the fungus Paraphoma radicina, which was isolated from submerged wood in a freshwater lake. Compounds 5, 6 and 9 were previously unknown. The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configurations of compounds 5 and 6 were determined by comparison of their experimental ECD measurements with values predicted by TDDFT calculations. Compounds 1-9 were evaluated for antimicrobial activity against an array of bacteria and fungi. The inhibitory activity of compound 4 against Staphylococcus aureus biofilm formation was evaluated.
University of North Carolina at Greensboro, Department of Chemistry and Biochemistry, Greensboro, NC 27402, United States.
Tamam
T
El-Elimat
University of North Carolina at Greensboro, Department of Chemistry and Biochemistry, Greensboro, NC 27402, United States.
Huzefa A
HA
Raja
Facultad de Química, Universidad Nacional Autónoma de México, Mexico DF 04510, Mexico.
Mario
M
Figueroa
Department of Biological Sciences, Virginia Polytechnic Institute and State University, Blacksburg, VA 24061, United States.
Joseph O
JO
Falkinham
University of North Carolina at Greensboro, Department of Chemistry and Biochemistry, Greensboro, NC 27402, United States. Electronic address: nicholas_oberlies@uncg.edu.
Nicholas H
NH
Oberlies
D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry* / Q000302:isolation & purification; D001419:Bacteria / Q000187:drug effects; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018441:Biofilms / Q000187:drug effects; D005285:Fermentation; D005618:Fresh Water; D005658:Fungi / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D013211:Staphylococcus aureus / Q000187:drug effects; D013764:Tetrahydronaphthalenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014934:Wood / Q000382:microbiology
D000890:Anti-Infective Agents; D001572:Benzofurans; D001578:Benzopyrans; D013764:Tetrahydronaphthalenes; C000594456:clearanol F; C000594457:clearanol G
Isobenzofuranone; Isochromenones; Paraphoma radicina; Tetrahydronaphthalenes