title: Trienylfuranol A and trienylfuranone A-B: metabolites isolated from an endophytic fungus, Hypoxylon submoniticulosum, in the raspberry Rubus idaeus.
abstract: A strain of Hypoxylon submonticulosum was isolated as an endophyte from a surface-sterilized leaf of a cultivated raspberry (Rubus idaeus). The liquid culture extract displayed growth inhibition activity against Saccharomyces cerevisiae using a disc diffusion assay. The extract's major component was identified as a new natural product, trienylfuranol A (1S,2S,4R)-1-((1'E,3'E)-hexa-1',3',5'-trienyl)-tetrahydro-4-methylfuran-2-ol (1), by high-resolution LC-MS and 1D and 2D NMR spectroscopy. Two additional new metabolites, trienylfuranones A (2) and B (3), were isolated as minor components of the extract and their structure elucidation revealed that they were biosynthetically related to 1. Absolute stereochemical configurations of compounds 1-3 were confirmed by NOE NMR experiments and by the preparation of Mosher esters. Complete hydrogenation of 1 yielded tetrahydrofuran 7 that was used for stereochemical characterization and assessment of antifungal activity.
authors.affiliation: London Research and Development Centre, Agriculture and Agri-Food Canada, London, Ontario, Canada.
authors.forename: Kevin M N
authors.initials: KMN
authors.lastname: Burgess
authors.affiliation: Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada.
authors.forename: Ashraf
authors.identifier: http://orcid.org/0000-0001-5775-7037
authors.initials: A
authors.lastname: Ibrahim
authors.affiliation: Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada.
authors.forename: Dan
authors.initials: D
authors.lastname: Sørensen
authors.affiliation: London Research and Development Centre, Agriculture and Agri-Food Canada, London, Ontario, Canada.
authors.forename: Mark W
authors.initials: MW
authors.lastname: Sumarah
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002853:Chromatography, Liquid; D060026:Endophytes / Q000302:isolation & purification / Q000378:metabolism; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D018515:Plant Leaves; D065856:Rubus / Q000382:microbiology*; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013098:Xylariales / Q000302:isolation & purification / Q000378:metabolism*
chemical_list: D000935:Antifungal Agents; D005663:Furans; C000620988:trienylfuranol A; C000620989:trienylfuranone A; C000620991:trienylfuranone B; D015107:4-Butyrolactone