title: Novel beta-methoxyacrylates of the 9-methoxystrobilurin and oudesmansin classes produced by the basidiomycete Favolaschia pustulosa.
abstract: Submerged liquid cultures of the basidiomycete Favolaschia pustulosa (Xenova culture collection no. X27732) afforded the novel 9-methoxystrobilurin derivatives, 9-methoxystrobilurin L (1) and 9-methoxystrobilurin E (2), and the related oudemansin derivative, oudemansin L (3). Their structures were established by 2D NMR experiments. Compounds 1 and 3 possess a novel arrangement of two isoprenoid units fused to the aromatic nucleus. Both 1 and 2 have the EEE-configuration in the pentadienyl side chain as reported previously for 9-methoxystrobilurins. Compound 1 was cytotoxic to cells of the human B lymphoblastoid cell line (Jijoye), with an IC50 of 1.8 nM. This cytotoxicity was observed in a 5- day assay only and was not apparent after 2 days. Compound 1 showed some antibacterial activity against Bacillus subtilis (MIC = 0.9 microM) and antifungal activity against Candida albicans (MIC = 6 microM).
authors.affiliation: Senova, Ltd., Berkshire, U.K.
authors.forename: K A
authors.initials: KA
authors.lastname: Wood
authors.forename: D A
authors.initials: DA
authors.lastname: Kau
authors.forename: S K
authors.initials: SK
authors.lastname: Wrigley
authors.forename: R
authors.initials: R
authors.lastname: Beneyto
authors.forename: D V
authors.initials: DV
authors.lastname: Renno
authors.forename: A M
authors.initials: AM
authors.lastname: Ainsworth
authors.forename: J
authors.initials: J
authors.lastname: Penn
authors.forename: D
authors.initials: D
authors.lastname: Hill
authors.forename: J
authors.initials: J
authors.lastname: Killacky
authors.forename: P
authors.initials: P
authors.lastname: Depledge
mesh_terms: D000179:Acrylates / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000302:isolation & purification / Q000494:pharmacology; D000935:Antifungal Agents / Q000302:isolation & purification / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000302:isolation & purification / Q000494:pharmacology*; D001487:Basidiomycota / Q000378:metabolism*; D004148:Dioxolanes / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005285:Fermentation; D006801:Humans; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D014407:Tumor Cells, Cultured
chemical_list: C101803:9-methoxystrobilurin E; C101802:9-methoxystrobilurin L; D000179:Acrylates; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D004148:Dioxolanes; C101804:oudemansin L; C023324:oudemansin