Crystal structure and theoretical calculations of Julocrotine, a natural product with antileishmanial activity

Abstract

Julocrotine,forms of Leishmania amazonensis (L.). In this work, the crystal structure of Julocrotine was solved by X-ray diffraction, and its geometrical parameters were compared with theoretical calculations at the B3LYP and HF level of theory. IR and NMR spectra also have been obtained and compared with theoretical calculations. IR absorptions calculated with the B3LYP level of theory employed together with the 6-311Gϩ(d,p) basis set, are close to those observed experimentally. Theoretical NMR calculations show little deviation from experimental results. The results show that the theory is in accordance with the experimental data.

Activity of the julocrotine, a glutarimide alkaloid from Croton pullei var. glabrior, on Leishmania (L.) amazonensis

“…Part of the hexane extract of the stem (20 g) was subjected to several column chromatography and thin layer chromatography on silica gel and eluted with hexane, EtOAc, and MeOH in increasing order of polarity, yielding 994 mg of Julocrotine. An alkaloid, julocrotine (2-[N-(2-methylbutanolyl)]-N-phenylethylglutarimide) (Fig.1), was one of the compounds isolated during plant extraction and fractioning (Barbosa et al 2007;Moreira et al 2008). One milligram of the drug was dissolved in 10 μL of chloroform and diluted in the culture medium (DMEM) and 1 mg/mL was used as the standard solution for the assay.…”

Synthesis of N-[(3S)-2,6-Dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2S)-2-methylbutanamide ((−)-Julocrotine)

“…The identity of 1 was confirmed on the basis of comparison of its NMR, IR, optical rotation, and melting point data with literature values. 4,5,19,20 The NMR description of 1 has been ameliorated in comparison to previous descriptions. 19,20 In conclusion, the total synthesis of optically active julocrotine (1) has been achieved in six steps with good overall yield (41%).…”

Volatiles, A Glutarimide Alkaloid and Antimicrobial Effects of Croton pullei (Euphorbiaceae)

“…Glutarimide alkaloids, among them julocrotine ( 1 ) and crotonimides B ( 2 ) and A ( 3 ) (Figure 1), terpenoids, flavonoids and a ferulamide derivative were previously isolated from C. pullei [7,8]. The structure of julocrotine was confirmed by X-ray analysis [9]. These glutarimide alkaloids were restricted to a small group of Euphorbiaceae, including Julocroton and some Croton species [10,11,12,13,14,15], but recently, julocrotine together with two other compounds of this class of substances were isolated from Cordia (Boraginaceae) [16].…”