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Four new chlorinated meroterpenoids, merochlorins G-J ( 1 - 4 ), and 10 , a dihydronaphthalenedione 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 determined 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.

Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp.