Structure of a naturally occurring antagonist of dihydrostreptomycin

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Abstract
A chemical examination has been made of a crystalline product from Pseudomonas pyocyanea (= P. aeruginosa) having the property of antagonizing the antibacterial action of dihydrostreptomycin. The product is a mixture containing as major components 2-n-heptyl-4-hydroxy-quinoline N-oxide and 2-n-nonyl-4-hydroxyquinoline N-oxide in the approximate proportion 21, along with a small proportion of 2-n-undecyl-4-hydroxyquinoline N-oxide. Traces of 2-n-octyl-4-hydroxy-quinoline N-oxide and of higher homologues may also be present. 2-n-Heptyl-, 2-n-nonyl- and 2-n-undecyl-4-hydroxyquinoline N-oxides have been synthesized. Of these, the 2-n-nonyl compound has the highest activity against dihydrostreptomycin.