Pilocarpus microphyllus Pilocarpine

Jaborandi leaves (Pilocarpus microphyllus and P. jaborandi Rutaceae) are also probably derived from histidine, but experimental data are lacking. Jaborandi leaves contain primarily pilocarpine and pilosine (Figure 6.112). Pilocarpine is valuable in... 

The pilocarpine used in medicine is of natural origin, which means it is being produced by extraction only as far as known, the leaves of Pilocarpus microphyllus are used at present. The syntheses reported (Section 1II,F) apparently cannot compete with the cheaper natural product. This is probably explained by the intricate stereochemical problems involved (Sections III,D and F). In 1928 Chemnitius described a typical large-scale extraction procedure (34). It is believed that this publication is the basis for later industrial manufacturing processes. Some older modifications or otherwise... 

The minor alkaloid pilosine was isolated irom Pilocarpus microphyllus by F. L. Pyman (46) and independently by E. Leger and F. Roques (116, 117) who named it carpiline. The crude alkaloid was obtained by fractional precipitation of the bases remaining in the mother liquor after the removal of pilocarpine and isopilocarpine, and it was purified by crystallization from 90% alcohol. The yield corresponded to a content of only 0.007 % of the leaves, and it was established that no other alkaloid was present in the leaves in quantity greater than 0.003% (46). 

Pilosine occurs in Pilocarpus microphyllus and P. jaborandi. The natural product consists of a 1 1 mixture of the epimers pilosine [carpidine, [a] +83.9° (C2H5OH)) and isopilosine [camiline, [a]p +37.6 (C2H5OH). Epiisopilosine ([aJo-44°(C2H50H) occurs in P. jaborandi. The effects of pilosine in mammals are similar but not so pronounced as those of pilocarpine. 

Abreu IN, Sawaya ACHF, Eberlin MN, Mazzafera P (2005) Production of pilocarpine in callus of jaborandi (Pilocarpus microphyllus Staph.). In vitro Cell Dev Biol Plant 41 806-811. doi 10.1079/IVP2005711... 

A cell suspension study with P. microphyllus recorded after several subcultures a stable cell line in pilocarpine and other imidazole alkaloids production and the same alkaloid profile found in leaves [41], This study also characterized three new alkaloids with imidazole ring in this plant species for the first time, by means of ESI-MS. Posterior studies using the same technique in leaves of several samples of Pilocarpus suggested three different pathways may occur in imidazole alkaloids biosynthesis [27, 41],... 

---