Isolation, structural elucidation, and synthesis of solapalmitine and solapalmitenine, two novel alkaloid tumor inhibitors from Solanum tripartitum

New chemistry of naturally occurring polyamines

“…13 homospermidines active against Herpes simplex, Bacillus subtilis, and Pseudomonas atrovenetum,38 Solapalmitine (11) and solapalmitenine (12), are two tetramethylated acyl derivatives of bis (4-aminobutyl)amine (13) that were shown by Kupchan to possess significant tumor-inhibitory activity. 39 Like 13, many of the more specialized polyamines with unusual carbon-nitrogen frameworks often surface as conjugates, the polyamino acid hypusine (14), found in various animal tissues40 and recently in human lymphocytes,41 would seem to be the product of coupling L-lysine with the known diamine hydroxyputrescine.42 However labeling studies reveal a more roundabout biogenesis in which spermidine provides hypusine's aminobutyl carbons.41 Two relatively new polyamines, thermospermine (15) and thermine (16), were discovered in the extreme thermophile Thermus thermophilus, a bacterium which grows normally at 75 °C.43,44 and are apparently the first spermidine metabolites to be discovered in marine organisms. Other acylated spermidines include many different classes of siderophores (or siderochromes)-iron-chelating substances that utilize hydroxamate.or catecholate groups to transport or sequester iron(III).…”

Synthesis of New Polyamine Derivatives for Cancer Chemotherapeutic Studies

“…This concept was substantiated by previous reports (26)(27)(28)(29) The urea derivative IVQ was prepared as follows. p-Nitrotrifluoroacetanilide (XVa), prepared from p-nitroaniline and trifluoroacetic anhydride, was reduced to the corresponding amino derivative XVb.…”

sym-Homospermidine, a naturally occurring polyamine

“…Two tetramethyl, acylated derivatives of iyw-homospermidine, Solapalmitine (10) and Solapalmitenine (11), have recently been discovered in Solanum tripartitum. These new alkaloids were reported to have significant tumor-inhibiting activity (Kupchan et al, 1967(Kupchan et al, , 1969. In an earlier and related report Israel and coworkers demonstrated (1964) antitumor activity in a series of synthetic spermidine and spermine analogs, though iym-homospermidine was not studied.…”