The mode of action of nanaomycins D and A on a gram-negative marine bacterium Vibrio alginolyticus.

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Abstract
Nanaomycin (NNM) D had a higher growth inhibitory activity than NNM-A against a gram-negative marine bacterium, V. alginolyticus. These quinone antibiotics were reduced by the respiratory chain-linked flavin dehydrogenase of the organism and the reduced forms of NNMs were quickly autoxidized by molecular O to produce superoxide radicals (O2-). NNM-D was more effective than NNM-A both in the induction of KCN-insensitive O2 consumption with the intact cells and in the production of O2- by the redox cycling. The growth inhibitory activities of NNM-D and A were partly reduced by raising the superoxide dismutase level of the cells. The ability to produce O2- at the cell membrane was correlated to the antibacterial activities of NNM-D and A.