New alkenylated tetrahydropyran derivatives from the marine sediment-derived fungus Westerdykella dispersa and their bioactivities

Six new alkenylated tetrahydropyran derivatives belonged to polyketides, designated as (12R,13R)-dihydroxylanomycinol (1), (12S,13S)-dihydroxylanomycinol (2), (12R,13S)-dihydroxylanomycinol (3) and (12S,13R)-dihydroxylanomycinol (4), (12S,13R)-N-acetyl-dihydroxylanomycin (5) and (12S,13S)-N-acetyl-dihydroxylanomycin (6), together with one related known compound lanomycinol (7) were isolated from the liquid cultures of Westerdykella dispersa obtained from the marine sediments. Their structures and absolute configurations were determined on the basis of extensive analysis of NMR spectra combined with comparison of NMR data to those of known compound, and computational method via calculation of the electronic circular dichroism (ECD). The anti-agricultural pathogenic fungal and antibacterial activities of all isolated compounds were evaluated. Compounds 1-7 exhibited moderate antifungal activities selectively against tested fungal strains with minimum inhibitory concentration (MIC) values ranging from 12.5 to 50 μg/mL, and weak antibacterial activities selectively against tested antibacterial strains with MIC value at 100 μg/mL.

Graphical abstractSix new alkenylated tetrahydropyran derivatives belonged to polyketides, designated as (12R, 13R)-dihydroxylanomycinol (1), (12S, 13S)-dihydroxylanomycinol (2), (12R, 13S)-dihydroxylanomycinol (3) and (12S, 13R)-dihydroxylanomycinol (4), (12S, 13R)-N-acetyl-dihydroxylanomycin (5) and (12S, 13S)-N-acetyl-dihydroxylanomycin (6), together with one related known compound lanomycinol (7) were isolated from the liquid cultures of Westerdykella dispersa obtained from the marine sediments. Their structures and absolute configurations were determined on the basis of extensive analysis of NMR spectra combined with comparison of NMR data to those of known compound, and computational method via calculation of the electronic circular dichroism (ECD). The anti-agricultural pathogenic fungal and antibacterial activities of all isolated compounds were evaluated. Compounds 1-7 exhibited moderate antifungal activities selectively against tested fungal strains with minimum inhibitory concentration (MIC) values ranging from 12.5 to 50 μg/mL, and weak antibacterial activities selectively against tested antibacterial strains with MIC value at 100 μg/mL.Download high-res image (179KB)Download full-size image