title: Antifungal metabolites from fungal endophytes of Pinus strobus.
abstract: The extracts of five foliar fungal endophytes isolated from Pinus strobus (eastern white pine) that showed antifungal activity in disc diffusion assays were selected for further study. From these strains, the aliphatic polyketide compound 1 and three related sesquiterpenes 2-4 were isolated and characterized. Compound 2 is reported for the first time as a natural product and the E/Z conformational isomers 3 and 4 were hitherto unknown. Additionally, the three known macrolides; pyrenophorol (5), dihydropyrenophorin (6), and pyrenophorin (7) were isolated and identified. Their structures were elucidated by spectroscopic analyses including 2D NMR, HRMS and by comparison to literature data where available. The isolated compounds 1, 2, and 5 were antifungal against both the rust Microbotryum violaceum and Saccharomyces cerevisae.
authors.affiliation: Department of Chemistry, Carleton University, 1125 Colonel By Drive, Ottawa, Ontario K1S5B6, Canada.
authors.forename: Mark W
authors.initials: MW
authors.lastname: Sumarah
authors.forename: Julie R
authors.initials: JR
authors.lastname: Kesting
authors.forename: Dan
authors.initials: D
authors.lastname: Sørensen
authors.forename: J David
authors.initials: JD
authors.lastname: Miller
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry*; D001483:Base Sequence; D001487:Basidiomycota / Q000187:drug effects; D060026:Endophytes / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007659:Ketones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification; D018942:Macrolides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D028223:Pinus / Q000382:microbiology*; D018515:Plant Leaves / Q000737:chemistry; D061065:Polyketides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D012440:Saccharomyces / Q000187:drug effects; D017422:Sequence Analysis, DNA; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: C582843:5-(hydroxymethyl)-2-(2',6',6'-trimethyltetrahydro-2H-pyran-2-yl)phenol; D000935:Antifungal Agents; D006571:Heterocyclic Compounds; D007659:Ketones; D007783:Lactones; D018942:Macrolides; D061065:Polyketides; D012717:Sesquiterpenes; C582842:methyl 6-(acetyloxy)-5-formyl-7-oxoocta-2,4-dienoate; C509954:pyrenophorol; C013228:pyrenophorin