N-(3-aminopropyl)pyrrolidin-2-one: A physiological excretory product deriving from spermidine

Add time:08/02/2019    Source:sciencedirect.com

1.1. Normal human and rat urine contain N-(3-aminopropyl)pyrrolidin-2-one. This compound was identified by its Chromatographic behaviour on a reversed phase column, by thin-layer chromatography of its dansyl derivative, and by mass spectrometry.2.2. Evidence for the presence of conjugates of N-(3-aminopropyl)pyrrolidin-2-one in urine was obtained by the fact that partial acid hydrolysis increases the amount of this compound, whereas prolonged hydrolysis leads to its transformation into isoputreanine (N1-carboxypropyll-1,3-diaminopropane).3.3. Although it is likely that the monoacetylderivative of N-(3-aminopropyl)pyrrolidin-2-one is prominent among the conjugates, since this compound can be formed from N1-acetylspermidine, other types of conjugates are also likely.4.4. A method is reported suitable for the measurement of N-(3-aminopropyl)pyrrolidin-2-one and of isoputreanine in urine and urine hydrolysates, respectively.5.5. Administration of spermidine enhances the amount of urinary excretion of N-(3-aminopropyl)pyrrolidin-2-one. Of 0.1 mmol·kg−1 of spermidine administered intraperitoneally to rats around 12% are transformed into this compound and its conjugates.6.6. Treatment of rats with aminoguanidine sulfate, an inhibitor of diamine oxidase, causes a decrease in the excretion of N-(3-aminopropyl)pyrrolidin-2-one and its derivatives.7.7. These findings are in agreement with the assumption that N-(3-aminopropyl)pyrrolidin-2-one, the γ-lactam of isoputreanine, is a physiological degradation product of spermidine. Its formation is catalyzed by an aminoguanidine sensitive, diamine oxidase-like enzyme.

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