ABSTRACT
Three new p-terphenyls (1-3), a new xanthone derivative (4), and two known fungal metabolites (5 and 6) have been isolated from the sclerotia of Penicillium raistrickii (NRRL 2039). The structures for 3,3"-dihydroxy-6'-desmethylterphenyllin (1); 3'-demethoxy-6'-desmethyl-5'-methoxycandidusin B (2); 6'-desmethylcandidusin B (3); and 1,3,5, 6-tetrahydroxy-8-methylxanthone (4) were determined on the basis of HRMS and NMR data. Although compounds 1 and 4 exhibited mild antiinsectan and antibacterial activity, griseofulvin (5) was responsible for most of the activity of the sclerotial extract in dietary assays against the corn earworm Helicoverpa zea.
Subject(s)
Insecticides/isolation & purification , Penicillins/isolation & purification , Penicillium/chemistry , Animals , Chromatography, High Pressure Liquid , Insecticides/chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Microbial Sensitivity Tests , Moths , Penicillins/chemistry , Penicillins/pharmacology , Spectrophotometry, UltravioletABSTRACT
Two new benzoquinones with antifungal, antibacterial, and cytotoxic activities have been isolated from liquid cultures of the coprophilous fungus Podospora anserina. The structures of anserinones A (1) and B (2) were assigned on the basis of MS and NMR results, and the absolute stereochemistry of 2 was deduced by analysis of 1H-NMR data for its (R)- and (S)-2-phenylbutyryl ester derivatives.
Subject(s)
Anti-Infective Agents/isolation & purification , Antifungal Agents/isolation & purification , Benzoquinones/isolation & purification , Anti-Bacterial Agents , Anti-Infective Agents/pharmacology , Antifungal Agents/pharmacology , Bacteria/drug effects , Benzoquinones/pharmacology , Fungi/drug effects , Magnetic Resonance Spectroscopy , Mass Spectrometry , Microbial Sensitivity Tests , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Xylariales/drug effectsABSTRACT
Four new prenylated bis-indolyl benzenoid metabolites (ochrindoles A-D; 1-4) were isolated from antiinsectan organic extracts of the sclerotia of Aspergillus ochraceus (NRRL 3519). The structures of these compounds were determined primarily through HMBC, selective INEPT, and NOESY experiments. These compounds displayed moderate activity in feeding assays against the corn earworm Helicoverpa zea and the driedfruit beetle Carpophilus hemipterus. Compounds 1-4 also exhibited activity against Gram-positive bacteria.
