Путресцин: Свойства, синтез и роль в биологических процессах

Foul smelling organic chemical compound

Putrescine is an organic compound with the formula (CH2)4(NH2)2. It is a colorless solid that melts near room temperature. It is classified as a diamine. Together with cadaverine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

Putrescine is produced on an industrial scale by the hydrogenation of succinonitrile.

Spermidine synthase uses putrescine and S adenosylmethioninamine (decarboxylated S adenosyl methionine) to produce spermidine. Spermidine in turn is combined with another S adenosylmethioninamine and gets converted to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. Putrescine is synthesized biologically via two different pathways, both starting from arginine. In one pathway, arginine is converted into agmatine. The conversion is catalyzed by the enzyme arginine decarboxylase (ADC). Agmatine is transformed into N carbamoylputrescine by agmatine imino hydroxylase (AIH). Finally, N carbamoylputrescine is hydrolyzed to give putrescine. In the second pathway, arginine is converted into ornithine and then ornithine is converted into putrescine by ornithine decarboxylase (ODC).

Putrescine is found in all organisms. Putrescine is widely found in plant tissues, The absence of putrescine in plants is associated with an increase in both parasite and fungal population in plants. Putrescine serves an important role in a multitude of ways, which include: a cation substitute, an osmolyte, or a transport protein. Piriformospora indica (P. indica) is one such fungus, found to promote putrescine production in Arabidopsis and common garden tomato plants. In a 2022 study it was shown that the presence of this fungus had a promotional effect on the growth of the root structure of plants. After gas chromatography testing, putrescine was found in higher amounts in these root structures. Plants that had been inoculated with P. indica had presented an excess of arginine decarboxylase. It is also found in semen and some microalgae, together with spermine and spermidine.

Putrescine reacts with adipic acid to yield the polyamide nylon 46, which is marketed by DSM under the trade name Stanyl. Application of putrescine, along with other polyamines, can be used to extend the shelf life of fruits by delaying the ripening process. Pre harvest application of putrescine has been shown to increase plant resistance to high temperatures and drought. Both of these effects seem to result from lowered ethylene production following exogenous putrescine exposure. Due to its role in putrification, putrescine has also been proposed as a biochemical marker for determining how long a corpse has been decomposing.

Putrescine and cadaverine were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).

In rats, putrescine has a low acute oral toxicity of 2000 mg/kg body weight, with no observed adverse effect level of 2000 ppm (180 mg/kg body weight/day).