title: Berkeleydione and berkeleytrione, new bioactive metabolites from an acid mine organism.
abstract: [structure: see text] Two novel hybrid polyketide-terpenoid metabolites were isolated from a Penicillium sp. growing in the Berkeley Pit Lake of Butte, Montana. Their structures were deduced by spectroscopic analysis and confirmed by single-crystal X-ray analysis on berkeleydione (1). Both compounds inhibited matrix metalloproteinase-3 and caspase-1, and berkeleydione showed activity toward non-small-cell lung cancer in NCI's human cell line antitumor screen.
authors.affiliation: Department of Chemistry, Montana Tech of the University of Montana, Butte, Montana 59701, USA. dstierle@mtech.edu
authors.forename: Donald B
authors.initials: DB
authors.lastname: Stierle
authors.forename: Andrea A
authors.initials: AA
authors.lastname: Stierle
authors.forename: J David
authors.initials: JD
authors.lastname: Hobbs
authors.forename: Janalee
authors.initials: J
authors.lastname: Stokken
authors.forename: Jon
authors.initials: J
authors.lastname: Clardy
mesh_terms: D000143:Acids; D061945:Caspase Inhibitors; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D004353:Drug Evaluation, Preclinical; D004791:Enzyme Inhibitors / Q000032:analysis / Q000302:isolation & purification*; D005618:Fresh Water / Q000382:microbiology; D006801:Humans; D018942:Macrolides / Q000032:analysis / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D061965:Matrix Metalloproteinase Inhibitors; D008906:Mining; D015394:Molecular Structure; D009009:Montana; D010408:Penicillium chrysogenum / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D013729:Terpenes / Q000032:analysis / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000143:Acids; D061945:Caspase Inhibitors; D004791:Enzyme Inhibitors; D018942:Macrolides; D061965:Matrix Metalloproteinase Inhibitors; D013729:Terpenes; C493366:berkeleydione; C493367:berkeleytrione