Pentaclethra macrophylla

A number of putrescine derivatives have been detected in nature for which one or two cinnamic acid analogs with amide linkages are known 4-coumaroylputrescine (2), di-4-coumaroylputrescine (3), feruloylpu-trescine (4) (subaphylline), diferuloylputrescine (5), caffeoylputrescine (6) (paucine), dicaffeoylputrescine (7), sinapoylputrescine (8), and disinapoyl-putrescine (9). Paucine, one of the first diaminoalkane alkaloids known since 1894 as a component of the seed of Pentaclethra macrophylla, was hydrolyzed (40% KOH - H20) to give putrescine and caffeic acid. Structure 6 was deduced (37) from this data together with spectroscopic data, especially mass spectra. Another derivative of putrescine, subaphylline (4), first isolated from Salsola subaphylla, was shown to be the monoferuloyl derivative of putrescine by hydrolysis (30% K0H-H20) (38). The structure elucidation of the other derivatives of putrescine (2, 3, 5, 7-9) mentioned before was undertaken in a manner similar to that of 4 and 6. Several compounds were synthesized and compared to the natural products and are summarized in Table II of Section V. 

A/-Ca feoylputrescine [discovered in Pentaclethra macrophylla Benth. (Fabaceae)] named pancine (Hesse 2000 and references therein), in N. tabacum and P. X hybrida... 

Jones, A.C., Robinson, J.M. and Southwell, K.H. (1987) Investigation into Pentaclethra macrophylla seed oil identification of hexacosanoic and octacosanoic fatty acids. J. ScL Food Agric. 40, 189-194. 

Mbadiwe, E. L Caffeoylputrescine from Pentaclethra macrophylla. Phytochemistry 12, 2546 (1973). 

In some plants, putrescine, agmatine, spermidine, and spermine are bound in amide linkage with one or two molecules of coumaric, caffeic, and/or fenilic acids, forming hydroxycinnamoyl acid amides. Caffeoylputrescine (paucine for structure see Fig. 7), known since 1894 as a component of the leguminous seed of Pentaclethra macrophylla (reviewed in Guggisberg and Hesse, 1983),... 

---