Antibacterial Gilvocarcin-Type Aryl-C-Glycosides from a Soil-Derived Streptomyces Species

Seven new gilvocarcin-type aryl -C-glycosides (1-7) and six known analogues (8-13) were isolated from the soil-derived Streptomyces sp. OUCMDZ-945. Their structures including absolute configurations were determined based on detailed spectroscopic analysis, chemical methods, ECD curves, and quantum chemical calculations. Compound 1, which we named digilvocarcin A, is the first reported bis-gilvocarcin derivative possessing a novel cyclobutane moiety. This dimeric skeleton was confirmed to be formed from gilvocarcin V (8) through a light-induced [2 + 2] cycloaddition. Compounds 1, 2, 5-8, and 11 showed antibacterial activity against Staphylococcus aureus ATCC 6538 and methicillin-resistant Staphylococcus aureus subsp. aureus ATCC 43300 (MIC values: 0.25-64 mu g/mL).