Microbial Metabolism of Quinoline and Related Compounds. XIX. Degradation of 4-Methylquinoline and Quinoline byPseudomonas putidaK1

A bacterial strain, designated K1, which utilizes 4-methylquinoline and quinoline as sole source of carbon, nitrogen and energy was isolated from soil. Based on its morphological and physiological characteristics, it was classified as Pseudomonas putida biovar B. Four metabolites of 4-methylquinoline degradation were isolated from the culture supernatant and identified as 4-methyl-2-oxo-1,2-dihydroquinoline, 8-hydroxy-4-methyl-2-oxo-1,2-dihydroquinoline, 7,8-dihydroxy-4-methyl-2-oxo-1,2-dihydroquinoline and 6-hydroxy-5-(2-carboxyethenyl)-4-methyl-1H-2-pyridone. Formation of the latter compound is suggested to proceed by decarbonylation of a putative meta-cleavage product of the 7,8-dihydroxy derivative. During growth on quinoline four compounds were released into the culture fluid, too. Upon isolation they were identified as 2-oxo-1,2-dihydroquinoline, 6-hydroxy-2-oxo-1,2-dihydroquinoline, 5-hydroxy-6-(3-carboxy-3-oxopropenyl)-1H-2-pyridone and 2H-pyran-2-on-[3,2b]-5H-6-pyridone. Thus it is proved, that Pseudomonas putida possesses two different catabolic pathways for various quinoline derivatives, which are induced selectively depending on the growth substrate.