Comparative vibrational spectra of pilosine and epiisopilosine crystals

Abstract

This paper describes the study of two alkaloids extracted from Pilocarpus Microphyllus (Rutaceae): pilosine and epiisopilosine. These substances have potential application in the treatment of several diseases. In this work FT-Raman and the FT-IR spectra of pilosine and epiisopilosine were investigated at 300 K. Vibrational wavenumber and wave vector have been predicted using density functional theory (B3LYP) calculations with the 6-31 G(d,p) basis set. A comparison with experiment, allowed us to assign most of the normal modes of the crystals.

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

“…The vibrational band assignments, presented in Table 3 , were proposed based on general literature about organic molecules [22]–[25] and a study reported about an isomer of EPI named epiisopilosine [26]. The vibrational assignments were supported by DFT calculations performed in this work as can be seen in Table 3 .…”

Imidazole alkaloids inhibit the pro-inflammatory mechanisms of human neutrophil and exhibit anti-inflammatory propertiesin vivo

“…[6] In Brazil, the Pilocarpus microphyllus Stapf ex Wardleworth leaves have been explored as a source of pilocarpine by the industry. Recently, a chemical study of the waste produced by pilocarpine extraction from P. microphyllus allowed the isolation of two imidazole alkaloids structurally similar: epiisopilosine (EPIIS) [7,8] and epiisopiloturine (EPI) [9,10] (Figure 1). EPI has several pharmacological properties, including antiparasitic, [9,11] antibacterial, antiproliferative activities.…”

Anthelmintic, Antibacterial and Cytotoxicity Activity of Imidazole Alkaloids fromPilocarpus microphyllusLeaves

“…Besides pilocarpine, as many as 15 other alkaloids have been isolated from P. microphyllus including pilosine (Bento et al, 2010), isopilosine (Santos and Moreno, 2004), epiisopilosine (Bento et al, 2010 ;Lucio et al, 2000), epiisopiloturine (Veras et al, 2013;Voigtlander et al, 1978) and macaubine (Santos and Moreno, 2004).…”

“…Epiisopiloturine has demonstrated effective activity against Schistosoma mansoni (Veras et al, 2013). Other studies reported that epiisopilosine is a peripheral parasympathetic nervous system stimulant (Lucio et al, 2000), and the physical properties of pilosine and epiisopilosine have been studied by Bento et al (2010) using Raman spectroscopy. These alkaloids are structurally similar, and there are some studies demonstrating their biological activity (Santos and Moreno, 2004).…”