Pilocarpus microphyllus

By extraction of Jaborandi leaves (especially Pilocarpus microphyllus Stapf.) and isolation as hydrochloride. 

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, isolated in 1912 by Pyman and by Leger and Roques (1) from Pilocarpus microphyllus, was named isopilosine (50) by Voigtlander and Rosenberg in 1959 (108). The latter authors isolated from the same plant another alkaloid and named it pilosine (51). Repetition of this work by Lowe and Pouk in 1973 (109) showed that the pilosine described by Voigtlander and Rosenberg was found to be a 1 1 mixture of pilosine and isopilosine. The two bases were separated by crystallization of pilosine as the salicylate isopilosine was isolated from the mother liquors. 

An alkaloid obtained from the leaflets of Pilocarpus microphyllus (Rutaceae) and other species of Pilocarpus. 

Pilocarpus Leaflets Pilocarpus [ microphyllus J Barosma betulina 1 Brazil... 

Pilosine, which was originally isolated from Pilocarpus microphyllus and P. jaborandi, has been shown to be a 1 1 molecular compound composed of (-1-)-pilosine (15) and (-I-)-isopilosine (14a). The mass spectra of (14a), (14b), and (15) have been studied. This report also describes a detailed investigation of the aldol condensation between pilosinine (10) and benzaldehyde and its 2- and 4-fluoro-derivatives. ... 

The dried and powdered leaves of Pilocarpus microphyllus is subjected to extraction for total alkaloids with ethanol acidified with hydrochloric acid. The solvent is removed under reduced pressure and the resulting aqueous residue is neutralized with ammonia and kept aside till all the resins settle down completely. It is subsequently filtered and the filtrate concentrated by evaporation to a small volume, made alkaline with ammonia and finally extracted with chloroform. The solvent is removed under reduced pressure and the contents dissolved in a minimum quantity of dilute nitric acid and the product is crystallized. 

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). 

A new Pilocarpus alkaloid, epi-isopiloturine, has been isolated from Pilocarpus microphyllus -, its structure (15) was elucidated by C n.m.r. spectroscopy and by its conversion into neopilosine and anhydropitoturine. N-Methylmurexine (16 R = Me) has been reported to occur in the marine gastropod mollusc Nucella... 

Pilocarpus jaborandi leaf Pilocarpus microphyllus leaf Pilocarpus pennatifolius leaf Piper longum fruit Piper methysticum rhizome, root Piper nigrum fruit Scutellaria baicalensis root... 

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, Mazzafera P, Eberlin MN, Zullo MAT, Sawaya ACHE (2007) Characterization of the variation in the imidazole alkaloid profile of Pilocarpus microphyllus in different seasons and parts of the plant by electrospray ionization mass spectrometry fingerprinting and identification of novel alkaloids by tandem mass spectrometry. Rapid Commun Mass Spectrom 21 1205-1213. doi 10.1002/rcm.2942... 

Sawaya ACHE, Abreu IN, Andreazza NL, Eberlin MN, Mazzafera P (2008) EIPLC-ESI-MS/MS of imidazole alkaloids in Pilocarpus microphyllus. Molecules 13 1518-1529. doi 10.3390/moleculesl3071518... 

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... 

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