Epiisopiloturin, ein neues Pilocarpus‐Alkaloid

Voigtländer, H. W.; Balsam, G.; Engelhardt, M.; Pohl, L.

doi:10.1002/ardp.19783111106

Cited by 19 publications

(25 citation statements)

References 14 publications

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“…Anhydropilosine (17) was reported previously (Voigtländer et al 1978) and was detected in samples of P. microphyllus from São Paulo and Maranhão states as well as in previous studies (Abreu et al 2007;Sawaya et al 2008). Here it was also observed in P. spicatus and in P. carajaensis, along with two other isomers (21, 22) with the same high resolution mass but with longer retention times.…”

Section: Alkaloid Profile In Different Speciessupporting

confidence: 70%

“…The next four peaks in the sample of P. microphyllus from Maranhão state (7, 9, 10 and 12) have the same mass and molecular formula and are isomers of pilosine, found in a previous study (Sawaya et al 2008), with slight differences in their ESI-MS/MS. Several epimers and isomers have been reported (Tedeschi et al 1974;Voigtländer et al 1978) with the same molecular formula. Of these isomers; pilosine has been reported in P. microphyllus and pilosine, isopilosine, epiisopilosine and epiisopiloturine in P. jaborandi (Santos and Moreno 2004).…”

Section: Alkaloid Profile In Different Speciesmentioning

confidence: 96%

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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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Section: Alkaloid Profile In Different Speciessupporting

confidence: 70%

Section: Alkaloid Profile In Different Speciesmentioning

confidence: 96%

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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“…The standard way of chemical shift assignments [22] was compared with theoretical DFT calculations for the isolated molecule and can be seen in Supporting Information S1 . The 1 H NMR data obtained in this work are in conformity with seminal results reported by Voigtlander et al [6].…”

Section: Resultssupporting

confidence: 92%

“…This “molecular fingerprint” of EPI has been previously reported in the literature[6]. Structural and spectroscopic characterizations were also performed to assure the integrity of the EPI molecule.…”

Section: Resultsmentioning

confidence: 77%

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Industrial Scale Isolation, Structural and Spectroscopic Characterization of Epiisopiloturine from Pilocarpus microphyllus Stapf Leaves: A Promising Alkaloid against Schistosomiasis

et al. 2013

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This paper presents an industrial scale process for extraction, purification, and isolation of epiisopiloturine (EPI) (2(3H)-Furanone,dihydro-3-(hydroxyphenylmethyl)-4-[(1-methyl-1H-imidazol-4-yl)methyl]-, [3S-[3a(R*),4b]]), which is an alkaloid from jaborandi leaves (Pilocarpus microphyllus Stapf). Additionally for the first time a set of structural and spectroscopic techniques were used to characterize this alkaloid. EPI has shown schistomicidal activity against adults and young forms, as well as the reduction of the egg laying adult worms and low toxicity to mammalian cells (in vitro). At first, the extraction of EPI was done with toluene and methylene chloride to obtain a solution that was alkalinized with ammonium carbonate. The remaining solution was treated in sequence by acidification, filtration and alkalinization. These industrial procedures are necessary in order to remove impurities and subsequent application of the high performance liquid chromatography (HPLC). The HPLC was employed also to remove other alkaloids, to obtain EPI purity higher than 98%. The viability of the method was confirmed through HPLC and electrospray mass spectrometry, that yielded a pseudo molecular ion of m/z equal to 287.1 Da. EPI structure was characterized by single crystal X-ray diffraction (XRD), 1H and 13C nuclear magnetic resonance (NMR) in deuterated methanol/chloroform solution, vibrational spectroscopy and mass coupled thermal analyses. EPI molecule presents a parallel alignment of the benzene and the methyl imidazol ring separated by an interplanar spacing of 3.758 Å indicating a π-π bond interaction. The imidazole alkaloid melts at 225°C and decomposes above 230°C under air. EPI structure was used in theoretical Density Functional Theory calculations, considering the single crystal XRD data in order to simulate the NMR, infrared and Raman spectra of the molecule, and performs the signals attribution.

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Anthelmintic, Antibacterial and Cytotoxicity Activity of Imidazole Alkaloids fromPilocarpus microphyllusLeaves

et al. 2017

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Pilocarpus microphyllus Stapf ex Wardlew (Rutaceae), popularly known as jaborandi, is a plant native to the northern and northeastern macroregions of Brazil. Several alkaloids from this species have been isolated. There are few reports of antibacterial and anthelmintic activities for these compounds. In this work, we report the antibacterial and anthelmintic activity of five alkaloids found in P. microphyllus leaves, namely, pilosine, epiisopilosine, isopilosine, epiisopiloturine and macaubine. Of these, only anthelmintic activity of one of the compounds has been previously reported. Nuclear magnetic resonance, HPLC and mass spectrometry were combined and used to identify and confirm the structure of the five compounds. As regards the anthelmintic activity, the alkaloids were studied using in vitro assays to evaluate survival time and damaged teguments for Schistosoma mansoni adult worms. We found epiisopilosine to have anthelmintic activity at very low concentrations (3.125 μg mL ); at this concentration, it prevented mating, oviposition, reducing motor activity and altered the tegument of these worms. In contrast, none of the alkaloids showed antibacterial activity. Additionally, alkaloids displayed no cytotoxic effect on vero cells. The potent anthelmintic activity of epiisopilosine indicates the potential of this natural compound as an antiparasitic agent. Copyright © 2017 John Wiley & Sons, Ltd.

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Epiisopiloturin, ein neues Pilocarpus‐Alkaloid

Cited by 19 publications

References 14 publications

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

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

Industrial Scale Isolation, Structural and Spectroscopic Characterization of Epiisopiloturine from Pilocarpus microphyllus Stapf Leaves: A Promising Alkaloid against Schistosomiasis

Anthelmintic, Antibacterial and Cytotoxicity Activity of Imidazole Alkaloids fromPilocarpus microphyllusLeaves

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