Pilocarpus jaborandi Pilocarpine

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)... 

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. 

Histidine is a precursor of a very limited number of alkaloids. The most well-known is pilocarpine from Pilocarpus jaborandi. The plant was formerly used as a truth serum (diaphoretic activity), and the alkaloid is used to counter the mydriatic effects of atropine. 

Pilocarpine Cholinergic agent used for glaucoma Pilocarpus jaborandi Jaborandi tree... 

The leaves of Pilocarpus species, including Pilocarpus jaborandi (jaborandi) and Pilocarpus racemosus (acei-tillo), contain pilocarpine or isopilocarpine as major alkaloids as well as a variety of minor alkaloids. Pilocarpine (see separate monograph) is an agonist at acetylcholine receptors, which enhances salivary flow, sweating, and gastrointestinal motility. It can interfere with asthma therapy and the effect of anticholinergic drugs. 

Pilocarpine Hydrochloride, USP. Pilocarpine mono-hydrochloride is the hydrochloride of an alkaloid oblaineil from the dried leaflets of Pilocarpus jaborandi or P. micro-pliylltis, in which it occurs to the extent of about 0.39 together with other alkaloids. 

Pilocarpine, the salt of an alkaloid obtained from Pilocarpus Jaborandi, is an example of a muscarinic agonist that does not adhere to the traditional SAR. In 1876, Langley reported that extracts containing the alkaloid stimulated the end organs of parasympathetic neurons. The structure of pilocarpine was reported in 1901. 

Jaborandi is the name of the crude drug prepared from the evergreen plants Pilocarpus jaborandi and Pilocarpus pinnatifolius, which grow wild in South America, especially in Brazil. In South America, 13 plants in this genus are known, and all are used as the material for Jaborandi, which is important as the material for the extraction of pilocarpine. 

Imidazole (glyoxaline) Pilocarpine Pilocarpus jaborandi Rutaceae... 

Jaborandi, as met with in commerce, consists of the dried leaflets of Pilocarpus jaborandi and other species of Pilocarpus and contains a number of associated alkaloids, among which are pilocarpine, /yopilocarpine and pilocarpidine. The method for the determination of total alkaloids described below is that recommended by the Analytical Methods Committee of the S,A,C, and was official in the B.P.C, 1949. 

Pilocarpine Pilocarpus jaborandi (Rutaceae) Substrate of CYP2A6 CYP2B (137,357)... 

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... 

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... 

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. 

This is undoubtedly the most important class of L-histidine derivatives only because of pilocarpine s (27) therapeutic uses [8, 23, 24]. Since Byasson s first report of jaborandi alkaloids isolation from the leaves of Pilocarpus spp. (Rutaceae) [8], in 1875, several other imidazole alkaloids have been reported in this genus. The identification of these was facilitated due to recent advances in hyphenated chromatographic techniques such as HPLC—ESI—MS/MS (high performance liquid chromatography with electrospray ionization tandem mass spectrometry). 

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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