Pfizer Handbook of Microbial Metabolites 



492 



H. von Euler and F. Schlenk, Z. physiol. Chem. 246 64 

 (1937). (Structure) 



Arthur Kornberg and W. E. Pricer, Jr., /. Biol. Chem. 186 

 557 (1950). 



;. QUINOLINES 



Quinolines are produced by bacteria and molds, but ap- 

 parently none has been reported from streptomycetes or 

 lichens. A complex of seven related 4-oxyquinolines is 

 elaborated by the oxidative bacterium Pseudomonas aeru- 

 ginosa (Bacillus pyocyaneus). These are commonly 

 called "pyo" compounds. 



Evidently no investigations have been made on the 

 mode of biosynthesis of microbial quinolines. The isola- 

 tion of anthranilic acid and of 2-n-heptyl-3-oxy-4-quino- 

 lone from "pyo" fermentation broths is suggestive, how- 

 ever.^ It seems probable that the "pyo" compounds could 



COOH 



NH2 

 Anthranilic 

 Acid 



OH 



N' 



H CH2CH2CH2CH2CH2CH2CH3 

 2-n-Heptyl-3-oxy-4-quinolone 



be formed essentially by condensation of anthranilic acid 

 or a biosynthetic precursor with a fatty acid or a fatty 

 acid precursor: 



O 



II 

 C— OH 



COOH 



+ 



NH2 



H2C 



c 



/\ 



O R 



O 



/ CH 



COOH 



.C— OH 



1. Oxidative 

 decarboxylation 



2. Dehydration 



OH 



IH] 



iRokuro Takeda, J. fermentation Technol. 37 59 (1959). 



