Novel beta-methoxyacrylates of the 9-methoxystrobilurin and oudesmansin classes produced by the basidiomycete Favolaschia pustulosa.
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).
Wood
K A
KA
Senova, Ltd., Berkshire, U.K.
Kau
D A
DA
Wrigley
S K
SK
Beneyto
R
R
Renno
D V
DV
Ainsworth
A M
AM
Penn
J
J
Hill
D
D
Killacky
J
J
Depledge
P
P
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
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