N-(3-aminopropyl)pyrrolidin-2-one, a product of spermidine catabolism in vivo

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Abstract
A high-pressure-liquid-chromatographic method suitable for the separation and sensitive detection of putreanine and isoputreanine is described. This method was used to study the formation of the metabolites of the oxidative deamination of spermidine and N1-acetylspermidine. Administration of spermidine trishydrochloride to mice causes a time-dependent accumulation of putreanine and N-(3-aminopropyl)pyrrolidin-2-one in various organs. The latter compound yields isoputreanine by hydrolysis. The analogous lactam, N-(3-acetamidopropyl)pyrrolidin-2-one is probably formed from N1-acetylspermidine, since hydrolysis of tissue extracts of N1-acetylspermidine-treated mice produced isoputreanine. No putreanine is formed under these conditions. Pretreatment of the animals with 25 mg of aminoguanidine sulfate/kg body wt completely inhibits the formation of putreanine and of the respective isoputreanine precursor from spermidine and N1-acetylspermidine. This suggests a role for a diamine oxidase-like enzyme in the oxidative deamination of spermidine and N1-acetylspermidine.