Polyamine alkaloids, putrescine, spermidine, spermine

PUTRESCINE, SPERMIDINE, SPERMINE, AND RELATED POLYAMINE ALKALOIDS... 

The naturally occurring di- and polyamine alkaloids are listed in the tables of Section V. At present, nearly 100 compounds have been reported. They were isolated from 56 genera in 30 plant and animal families. Some of the plants contain all three kinds of alkaloids (putrescine, spermidine, and spermine), e.g., Ananas comosus Merill. (Bromeliaceae). Intensive investigations of alkaloids were performed in some genera, e.g., Aphelandra, Chaenorhinum, Equisetum, Maytenus. The reasons were commercial availability and pharmacological interest (Maytenus). 

Chapter 3. Putrescine, Spermidine, Spermine, and Related Polyamine Alkaloids Armin Guggisberg and Manfred Hesse... 

An interesting group of alkaloid substances, not previously discussed in these volumes, are the polyamine alkaloids they are reviewed in a chapter entitled Putrescine, Spermidine, Spermine, and Related Polyamine Alkaloids. Recently available books on alkaloids of a general nature, primarily intended for students of natural products, are not going to replace a treatise that continues to be detailed, complete, and up-to-date. 

Putrescine, spermidine, spermine, and related polyamine alkaloids 02MI25. 

Guggisberg, a. and M. Hesse, Putrescine, spermidine, spermine, and related polyamine alkaloids, in The Alkaloids, Vol. 22 (A. Brossi, ed.), 85-188, Academic Press, New York, 1983. 

Concerning the nature of the polyamine alkaloids, characteristic differences exist. In the case of putrescine alkaloids the base is always a chain in spermidine and spermine alkaloids the cyclic form is predominant. The 13-membered and 17-membered lactams are the preferred rings in the spermidine and spermine alkaloids, respectively. As shown in Scheme 41... 

An investigation of the spermine alkaloids present in the roots of several Aphelandra species has indicated that the polyamines putrescine, spermidine, and spermine interconvert, whereas the alkaloid (- -)-aphelandrine (98) content varies considerably during the first year. This is presumed to be due to the need for the diamine precursors to be used to transport cations, especially during bud formation (55). 

Putrescine is an important intermediate in the biosynthesis of tropane alkaloids acting also as a precursor for polyamines, spermine and spermidine, and also for the biosynthesis of nicotine [111, 122]. 

Incorporations, similar to that for putrescine, were observed for spermine (46) and spermidine (47) (also measured against arginine C-labels on asterisked carbons), and there was a similar distribution of the label. These amines can, like putrescine, then be converted into pyrrolizidine alkaloids via the hypothetical (44) both polyamines are known to be degraded to pyrrolines, resembling (44), plus 1,3-diaminopropane on oxidation with plant polyamine oxidases. 

Chemical compounds such as spermine are called polyamines, and among them are spermidine and putrescine, in addition to spermine. Spermidine is also present in semen. Various biological activities are known for these alkaloids [3,4]. 

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