Antibacterial meroterpenoids, merochlorins g–j from the marine bacterium streptomyces sp.

Abstract

Four new chlorinated meroterpenoids, merochlorins G−J (1−4), and 10, a dihydronaph-thalenedione precursor, along with known merochlorins A (5) and C−F (6−9), were obtained from cultivation of the bacterium strain Streptomyces sp. CNH-189, which was isolated from marine sediment. The planar structures of compounds 1−4 and 10 were elucidated by interpretation of MS, UV, and NMR spectroscopic data. The relative configurations of compounds 1−4 were deter-mined via analysis of nuclear Overhauser effect (NOE) spectroscopic data, after which their absolute configurations were established by comparing the experimental electronic circular dichroism (ECD) spectra of compounds 1−4 to those of previously reported possible enantiomer models and DP4 calculations. Compound 3 displayed strong antibacterial activities against Bacillus subtilis, Kocuria rhizophila, and Staphylococcus aureus, with MIC values of 1, 2, and 2 µg/mL, respectively, whereas compound 1 exhibited weak antibacterial effects on these three strains, with a 16−32 µg/mL MIC value range.