HPLC-ESI-MS/MS of Imidazole Alkaloids in Pilocarpus microphyllus

Sawaya, Alexandra Christine Helena Frankland; Abreu, Ilka Nacif; Andreazza, Nathalia Luiza; Eberlin, Marcos N.; Mazzafera, Paulo

doi:10.3390/molecules13071518

Cited by 24 publications

(21 citation statements)

References 16 publications

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“…Therefore, lineage P would be interesting for commercial exploration using bioreactors, since it is friable and produces and excretes exclusively pilocarpine. In contrast, although lineage PP produces pilosine and pilocarpine, it is an interesting model to study the biosynthesis of imidazole alkaloids in jaborandi since the biosynthesis routes of pilocarpine and pilosine seem to be related (Abreu et al 2007b;Sawaya et al 2008).…”

Section: ) Andmentioning

confidence: 89%

“…In aqueous solution, pilocarpine may epimerize to isopilocarpine which, in turn, hydrolyzes to isopilocarpic acid (Abreu et al 2007b). Unfortunately, diastereoisomers cannot be distinguished from their original structures by the ESI-MS method used here (Abreu et al 2007a;Sawaya et al 2008). Together with the other alkaloids detected in the cell and in the media, the pH might be controlled by alkaloid production, release and/or modification of the acidic form.…”

Section: ) Andmentioning

confidence: 92%

“…Although information on the content of pilocarpine in jaborandi is available (Pinheiro 1997;Andrade-Neto et al 1996), very little is known about its biosynthesis (Avancini et al 2003;Abreu et al 2005Abreu et al , 2007aSandhu et al 2006;Sawaya et al 2008).…”

Section: Introductionmentioning

confidence: 99%

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Production of imidazole alkaloids in cell cultures of jaborandi as affected by the medium pH

et al. 2008

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The effect of pH (from 4.8 to 9.8) on the production of pilosine and pilocarpine and on their partition between cell and medium was studied in two lineages (P and PP) of Pilocarpus microphyllus cell suspension cultures. Highest mass accumulation was observed at high pHs and both lineages produced pilocarpine while only lineage PP produced pilosine. Both alkaloids were released in the medium but higher accumulation occurred in the cells. The highest production of pilocarpine was at pH 8.8-9.8 in both cell lineages. Other imidazole alkaloids were also identified in both lineages. At all pHs tested, the pH in the media cultures tended to stabilize around 6 after 10-15 days of cultivation. NO 3 -and NH 4 ? variation in the media might partially explain the pH stabilization.

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Section: ) Andmentioning

confidence: 89%

Section: ) Andmentioning

confidence: 92%

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Production of imidazole alkaloids in cell cultures of jaborandi as affected by the medium pH

et al. 2008

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“…Recently, a high performance liquid chromatography method compatible with electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) was developed and used to study alkaloids in P. microphyllus (Sawaya et al 2008). This method reduces the possibility of degradation, isomerisation and artifacts which haunt classical phytochemical techniques.…”

Section: Introductionmentioning

confidence: 99%

Screening species of Pilocarpus (Rutaceae) as sources of pilocarpine and other imidazole alkaloids

Sawaya

Vaz

Eberlin

et al. 2011

Genet Resour Crop Evol

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Plants of the Pilocarpus genus (Rutaceae) are popularly known as jaborandi and are the only source of pilocarpine, an imidazole alkaloid used in eye-drops for the treatment of glaucoma as well as for the stimulation of sweat and lachrymal glands. Alkaloid extracts from leaf samples of seven species of Pilocarpus, from the states of São Paulo and Maranhão in Brazil, were analyzed using HPLC-ESI-MS/MS. The samples contained between 0.88 ± 0.04 and 1.00 ± 0.14% of alkaloids in relation to the dry weight of their leaves, with significant differences in results (P B 0.05) found only between Pilocarpus microphyllus planted in the state of Maranhão and Pilocarpus spicatus, Pilocarpus trachyllophus, Pilocarpus pennatifolius and Pilocarpus jaborandi; as well as between Pilocarpus spicatus and Pilocarpus racemosus. Pilocarpine was not found in P. spicatus, whereas in the other species it ranged from 2.6 ± 0.1 to 70.8 ± 1.2% of total alkaloids. P. microphyllus planted in the state of Maranhão for pilocarpine extraction had the highest total alkaloid content, but it had only 35% of pilocarpine in relation to total alkaloids. Three other species contained more pilocarpine in relation to total alkaloids: P. jaborandi (70.8%), P. racemosus (45.6%) and P. trachyllophus (38.7%); and could be candidates for pilocarpine extraction. Differences in alkaloid content were significant for all these samples (P B 0.05). Imidazole alkaloids were observed and partially characterized based on their retention times and high resolution mass. The seven species analyzed had different imidazole alkaloid profiles, but only one did not present quantifiable pilocarpine contents in its leaves. The Pilocarpus genus shows potential for the prospection of novel alkaloids.

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“…Plants of this genus are characterized by the natural presence of pilocarpine in their leaves. This imidazole alkaloid is used to treat glaucoma and xerostomia by the pharmaceutical industry (Sawaya et al, 2008). One of the most important drugs in ophthalmology is derived from the leaves of this shrub, which is harvested by the indigenous and peasants in the forests of Brazil.…”

Section: Discussionmentioning

confidence: 99%

Medicinal plants used in Rondônia, Western Amazon, Brazil

Santos

Lima

Oliveira

2014

Rev. bras. plantas med.

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ABSTRACT:This study refers to the use of medicinal plants by populations in the Western Amazon and provides information that can be used in phytochemical studies. It draws upon the traditional knowledge regarding the use of medicinal plants in five regions of the state of Rondônia, in the Brazilian Amazon, focusing on native species. The field research was carried out in five municipalities of the state of Rondônia: Ariquemes, Buritis, Candeias do Jamari, Cujubim and Itapoa do Oeste, characterized by primary economic sectors: agriculture, cattle farming, plant extraction and mineral exploration. Structured interviews were applied to 227 persons chosen because of their prestige in the communities in relation to the knowledge and use of medicinal plants, identifying the therapeutic purpose, parts of the plant used and methods of preparation. The species were taxonomically identified. The ethnobotanic knowledge (inferred by the number of uses of medicinal plants per person) was correlated with the Brazilian region of origin, age, and gender of the interviewees. According to the collected data, 34 botanical families and 53 native species were identified. Of the 53 species, only 7 occur exclusively in the Amazon Forest: Theobroma grandiflorum (Willd. ex Spreng.) K. Schum., Psidium densicomum Mart. ex DC, Piper cavalcantei Yunck., Pilocarpus microphyllus Stapf ex Wardlew., Euterpe oleracea Mart., Croton cajucara Benth., Baccharis altimontana G. Heiden. The most common disorders treated with the plants were kidney problems, influenza, generalized infections and inflammations, malaria and high blood pressure. Leaves were the most used parts in preparations. Barks, fruits, roots, flowers, stems, seeds, oils, buds, tubercles, and rhizomes were also mentioned. Thirteen forms of preparations were recorded, and infusion and decoction were the most used. Syrups, juices, flour, sap, oil and parts of the plant blended with milk, honey and coffee or flamed, macerated and in the form of poultice, were also found. Persons from the Southeast region had more information compared with persons from the other regions; persons in the age groups between 50-59, 60-69 and 70-79 had more information in comparison with the other age groups; and the female interviewees mentioned significantly more uses of medicinal plants than the male ones. The relatively small number of native Amazon species identified can be the result of the loss of knowledge about medicinal plants in the Amazon because of internal migration, extinction of local indigenous groups, increasing urbanization and consequent globalization of the lifestyles. Keywords: Ethnobotany, Phytotherapy, Traditional Medicine.RESUMO: Plantas medicinais usadas em Rondônia, Amazônia Ocidental, Brasil. Este estudo se refere ao uso de plantas medicinais por populações da Amazônia Ocidental, fornece informações passíveis de utilização em estudos fitoquímicos e resgata o conhecimento tradicional a respeito do uso de plantas medicinais em cinco regiões do estado de Rondônia na Amazônia Brasileira...

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HPLC-ESI-MS/MS of Imidazole Alkaloids in Pilocarpus microphyllus

Cited by 24 publications

References 16 publications

Production of imidazole alkaloids in cell cultures of jaborandi as affected by the medium pH

Production of imidazole alkaloids in cell cultures of jaborandi as affected by the medium pH

Screening species of Pilocarpus (Rutaceae) as sources of pilocarpine and other imidazole alkaloids

Medicinal plants used in Rondônia, Western Amazon, Brazil

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