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HPLC-ESI-MS/MS of Imidazole Alkaloids in Pilocarpus microphyllus
ThoMSon Mass Spectrometry Laboratory, Institute of Chemistry, State University of Campinas - UNICAMP, Campinas, SP, Brazil
Bandeirante University of São Paulo, UNIBAN, São Paulo, SP, Brazil
Department of Plant Physiology, Institute of Biology, State University of Campinas - UNICAMP, Campinas, SP, Brazil
Umeå Plant Science Centre – Umeå – Sweden
* Author to whom correspondence should be addressed.
Received: 28 May 2008; in revised form: 22 June 2008 / Accepted: 18 July 2008 / Published: 30 July 2008
(This article belongs to the Special Issue Alkaloids
Abstract: Pilocarpine, an important imidazole alkaloid, is extracted from the leaves of Pilocarpus microphyllus (Rutaceae), known in Brazil as jaborandi and used mainly for the treatment of glaucoma. Jaborandi leaves also contain other imidazole alkaloids, whose pharmacological and physiological properties are unknown, and whose biosynthetic pathways are under investigation. In the present study, a HPLC method coupled with ESI-MSn was developed for their qualitative and quantitative analysis. This method permits the chromatographic separation of the imidazole alkaloids found in extracts of jaborandi, as well as the MS/MS analysis of the individual compounds. Thus two samples: leaves of P. microphyllus and a paste that is left over after the industrial extraction of pilocarpine; were compared. The paste was found to contain significant amounts of pilocarpine and other imidazole alkaloids, but had a slightly different alkaloid profile than the leaf extract. The method is suitable for the routine analysis of samples containing these alkaloids, as well as for the separation and identification of known and novel alkaloids from this family, and may be applied to further studies of the biosynthetic pathway of pilocarpine in P. microphyllus.
Keywords: Jaborandi; Pilocarpus microphyllus; imidazole alkaloids; pilocarpine; HPLCESI- MS/MS.
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Sawaya, A.; Abreu, I.N.; Andreazza, N.L.; Eberlin, M.N.; Mazzafera, P. HPLC-ESI-MS/MS of Imidazole Alkaloids in Pilocarpus microphyllus. Molecules 2008, 13, 1518-1529.
Sawaya A, Abreu IN, Andreazza NL, Eberlin MN, Mazzafera P. HPLC-ESI-MS/MS of Imidazole Alkaloids in Pilocarpus microphyllus. Molecules. 2008; 13(7):1518-1529.
Sawaya, Alexandra; Abreu, Ilka N.; Andreazza, Nathalia L.; Eberlin, Marcos N.; Mazzafera, Paulo. 2008. "HPLC-ESI-MS/MS of Imidazole Alkaloids in Pilocarpus microphyllus." Molecules 13, no. 7: 1518-1529.