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Seventeen new compounds, naphthacemycins A 1 -A 11 , B 1 -B 4 and C 1 -C 2 , were isolated from a cultured broth of Streptomyces sp. KB-3346-5 during screening for circumventors of β-lactam resistance in methicillin-resistant Staphylococcus aureus. Their structures were elucidated by spectroscopic studies, including NMR and X-ray crystallographic analysis. The naphthacemycin A series has a new skeleton displaying a 7-phenylnaphthacene-5,6,11(12H)-trione. In contrast, the quinone moiety of the A series is changed to dehydroxyquinol in the B series and to a semiquinone-like structure in the C series.

Naphthacemycins, novel circumventors of β-lactam resistance in MRSA, produced by Streptomyces sp. KB-3346-5. II. Structure elucidation