학술논문

Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp.
Document Type
article
Source
Marine Drugs. 19(11)
Subject
Chemical Sciences
Physical Chemistry
Infectious Diseases
Animals
Anti-Bacterial Agents
Aquatic Organisms
Bacillus subtilis
Microbial Sensitivity Tests
Micrococcaceae
Staphylococcus aureus
Streptomyces
Terpenes
chlorinated meroterpenoid
merochlorins G J
dihydronaphthalenedione precursor
ECD
DP4
antibacterial
merochlorins G−J
Physical Chemistry (incl. Structural)
Pharmacology and Pharmaceutical Sciences
Medicinal & Biomolecular Chemistry
Pharmacology and pharmaceutical sciences
Physical chemistry
Language
Abstract
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.