Über die Synthese der <i>Pilocarpus</i>‐Alkaloide Isopilosin und Pilocarpin, sowie die absolute Konfiguration des (+)‐Isopilosins

Link, Helmut; Bernauer, Karl

doi:10.1002/hlca.19720550402

Cited by 36 publications

(8 citation statements)

References 7 publications

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“…1 C and D); 1tyrosine (δ 7.22 -H-2 and 6), 2 -β glucose (δ 4.58), and 3lactone ring (δ 4.18, H-8). compounds 6 (m/z 241) or 8 (m/z 285), as previously described in imidazole alkaloid synthesis [4]. In this study we have shown that NMR and MS are complementary techniques for the identification of different classes of metabolites in P. microphyllus.…”

Section: Compoundsupporting

confidence: 56%

“…P. microphyllus is economically the most important representative of jaborandi because it contains high concentrations of the imidazole alkaloid, pilocarpine, which is used to treat glaucoma as a stimulant of lachrymal and sweat glands and in the control of xerostomia [1]. In addition to pilocarpine, other imidazole alkaloids such as 3-nor-8 (11)-dihydropilocarpine, anhydropilosine, pilosine, and pilosinine have also been found in jaborandi leaf extracts [2][3][4][5]. However, of all these imidazole alkaloids produced in P. microphyllus, only pilocarpine has pharmaceutical applications.…”

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confidence: 99%

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Metabolic Alterations in Different Developmental Stages ofPilocarpus microphyllus

Abreu¹,

Choi

Sawaya

et al. 2010

Planta Med

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Pilocarpine is an imidazole alkaloid that has been used for more than a century in glaucoma treatment. It is present in several species of the Pilocarpus genus (jaborandi), with its highest concentrations in P. microphyllus. In addition to pilocarpine, pilosine--an imidazole alkaloid without pharmacological use--is produced in high concentrations in mature plants. A metabolomic study was carried out on juvenile and mature plants to obtain information about pilocarpine metabolism at different developmental stages. Methanol-water and alkaloid extracts were analyzed by ¹H NMR and ESI-MS. Metabolic profiles from both techniques showed clear differences between various developmental stages. Intense signals in the aromatic region of the ¹H NMR spectrum and ions from pilosine and related alkaloids by ESI/MS were found only in extracts from mature plant. Two new imidazole alkaloids were identified by MS(n). Our results suggest that pilosine is produced exclusively in mature developmental stage, and juvenile plant material seems to be appropriate for further studies on pilocarpine biosynthesis.

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Section: Compoundsupporting

confidence: 56%

mentioning

confidence: 99%

Metabolic Alterations in Different Developmental Stages ofPilocarpus microphyllus

Abreu¹,

Choi

Sawaya

et al. 2010

Planta Med

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“…2) has high resolution mass and fragmentation compatible with dehydropilosinine, reported in the synthesis of pilocarpine proposed by Link and Bernauer (1972). This alkaloid was found in six of the species: P. carajaensis, P. spicatus, P. trachyllophus, P. pennatifolius, P. jaborandi and P. racemosus, indicating that it is also quite common in this genus.…”

Section: Alkaloid Profile In Different Speciesmentioning

confidence: 87%

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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“…Pilocarpus microphyllus is the species of the genus which accumulates the largest amount of pilocarpine in leaves and is found mainly in the Amazon region of Brazil (Pinheiro, 1997). In addition to pilocarpine, leaf extracts from this species also contain other alkaloids, such as 3-nor-8(11)-dihydropilocarpine, anhydropilosine and pilosine, pharmacological activity of which is still unknown (Andrade Neto et al, 1996;Link and Bernauer, 1972;Voigtlander, 1978). Similar to other species from this region, it has been extensively exploited and, as a result, it was included a few years ago in the list of Brazilian endangered plant spe-cies (Pinheiro, 1997).…”

Section: Introductionmentioning

confidence: 99%

Cell Suspension as a Tool to Study the Biosynthesis of Pilocarpine in Jaborandi

et al. 2007

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Jaborandi (Pilocarpus microphyllus) is a species that naturally occurs in the North and Northeast of Brazil, whose leaves produce pilocarpine (an imidazole alkaloid that has been used to treat glaucoma and xerostomy), the biosynthesis of which is still uncertain. The aim of this work was to establish cell lineages and select them according to an alkaloid profile similar to the one from Jaborandi leaves. The induction of callus was done in different culture media and growth regulators. Calluses from primary cultures or those subcultured several times were used as explants for the obtainment of six cell lineages. Alkaloids content analyses and growth curves showed that lines obtained from primary cultures produced more alkaloids and a better development. Cell lines from 12 subcultures presented a decrease in pilocarpine and pilosine production. After 24 subcultures, the production of alkaloids remained constant. ESI-MS analysis showed that cell culture extracts have the same alkaloid composition as extracts made from leaves. The results indicate that cell suspensions can be used as a model to study the biosynthesis of the imidazole alkaloid in P. microphyllus.

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Über die Synthese der Pilocarpus‐Alkaloide Isopilosin und Pilocarpin, sowie die absolute Konfiguration des (+)‐Isopilosins

Cited by 36 publications

References 7 publications

Metabolic Alterations in Different Developmental Stages ofPilocarpus microphyllus

Metabolic Alterations in Different Developmental Stages ofPilocarpus microphyllus

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

Cell Suspension as a Tool to Study the Biosynthesis of Pilocarpine in Jaborandi

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