Pilocarpus

The principal facts relating to the alkaloidal constituents of the leaves of Pilocarpus spp. arc shown in the following table. 

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

Examples of alkaloid of relative pharmaceutical usefulness so far characterized from Rutaceae are pilocarpine from Pilocarpus jaborandi Holmes. This imidazole alkaloid is occasionally used to treat glaucoma. 

The choline ester, carbachol, activates M-cholinoceptors, but is not hydrolyzed by AChE. Carbachol can thus be effectively employed for local application to the eye (glaucoma) and systemic administration (bowel atonia, bladder ato-nia). The alkaloids, pilocarpine (from Pilocarpus jaborandi) and arecoline (from Areca catechu betel nut) also act as direct parasympathomimetics. As tertiary amines, they moreover exert central effects. The central effect of muscarinelike substances consists of an enlivening, mild stimulation that is probably the effect desired in betel chewing, a widespread habit in South Asia. Of this group, only pilocarpine enjoys therapeutic use, which is limited to local application to the eye in glaucoma... 

Pilocarpine (15) Pilocarpus jaborandi Holmes (jaborandi), and related species Cholinergic (parasympathomimetic)... 

Pilocarpine (30) is one of a series of related alkaloids found in the South American plant genus Pilocarpus, known commonly as Jaborandi leaf, which was used in traditional medicine to induce sweating and urination. The molecular structure of (30) bears similarities to ACh (2) since the positively-charged N-atom and the lactone binding to the serine are about the same distance apart. Chewing the leaf results in typical features... 

The basic alkaloid in Pilocarpus jaborandi (Rutaceae) is pilocarpine, a molecule of which contains an imidazole nucleus and is also used as a clinical drug. During alkaloid synthesis, L-histidine can produce the manzamine nucleus (Figure 27). These alkaloids are quite widespread, though they were first isolated in the late 1980s in marine sponges. They have an unusual polycyclic system and a very broad range of bioactivities. Common alkaloids with this nucleus include manzamine A, manzamine B, manzamine X, manzamine Y, sextomanzamine A and so on. 

Almocarpine/ Brazilian Pilocarpus Ayerst jaborandi Holmes,... 

Source leaflets of South American shrub Pilocarpus jaborandi Uses treatment of open-angle glaucoma... 

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... 

Imidazole (glyoxaline) is the principal nucleus in histamine from ergot and pilocarpine from pilocarpus (Figure 11.6). 

The NMR spectra of some Pilocarpus alkaloids, pilosinine, iso-pilosine, and epi-isopilosine, are summarized in structures [318], [319],... 

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