Context: 'Carnauba' wax is a natural product obtained from the processing of the powder exuded from Copernicia prunifera (Miller) H. E. Moore (Arecaceae). This material is widely used in the Brazilian folk medicine, including the treatment of rheumatism and syphilis. Objective: To investigate the antiprotozoal activity of hexane and EtOH extracts from the 'carnauba' wax as well as from the isolated compounds from the bioactive extracts. Material and methods: Two different samples of 'carnauba' (C. prunifera) waxes -types 1 and 4 -were individually extracted using hexane (EH) and EtOH (EE). Aliquots of hexane (type 1 -EH-1 and EH-4) and EtOH (type 4 -EE-1 and EE-4) extracts were tested against promastigote (2-200 lg/mL in DMSO during 48 h at 24 C) and amastigote (3-150 lg/mL in DMSO during 120 h at 37 C) forms of Leishmania infantum as well as against trypomastigote (3-150 lg/mL in DMSO during 24 h at 37 C) forms of Trypanosoma cruzi. Bioactive extracts EH-1 and EE-4 were subjected to a bioactivity-guided fractionation to afford three dammarane-type triterpenoids (1-3). The in vitro antiprotozoal activities of the obtained compounds were evaluated as described above. Additionally, the cytotoxicity activity of compounds 1-3 against mammalian conjunctive cells (NCTC -2-200 lg/mL in DMSO during 48 h at 37 C) was determined. Results: From the bioactive hexane and EtOH extracts from the 'carnauba' (C. prunifera) wax, were isolated three dammarane-type triterpenoids: (24R Ã )-methyldammar-25-ene-3b,20-diol (carnaubadiol, 1), (24R Ã )-methyldammara-20,25-dien-3-one (2) and (24R Ã )-methyldammara-20,25-dien-3a-ol (3). These compounds were identified based on the analysis of NMR and MS spectroscopic data. Compounds 1-3 were effective against the intracellular amastigotes of L. infantum, with IC 50 values ranging from 8 to 52 lM, while compounds 1 and 3 displayed activity against trypomastigote forms of T. cruzi with IC 50 values of 15 and 35 lM, respectively. The mammalian cytotoxicity assay demonstrated no damage to NCTC conjunctive cells up to 200 lM, except for compound 1, which demonstrated a CC 50 value of 34 lM. Conclusion: Based on the results, it was possible to conclude that the detected antiprotozoal bioactivity of 'carnauba' (C. prunifera) wax extracts could be related to the presence of the natural dammarane triterpenoid derivatives. The results suggested that these compounds could be used as promising scaffolds for drug design studies for leishmaniasis and Chagas disease. ARTICLE HISTORY
Platonia insignis Mart., popularly known as “bacurizeiro,” is used in traditional medical practices based on its diverse biological properties. This study was aimed at evaluating the antileishmanial effects of the ethanol extract (EtOH-Ext), hexane fraction (Hex-F), and its main isolated Lupeol obtained from stem barks of P. insignis against Leishmania (Leishmania) amazonensis, as well as their cytotoxicity and possible mechanisms of action. The EtOH-Ext, Hex-F, and Lupeol inhibited the growth of L. amazonensis promastigote forms at IC50 of 174.24, 45.23, and 39.06 µg/mL, respectively, as well as L. amazonensis axenic amastigote forms at IC50 of 40.58, 35.87, and 44.10 µg/mL, respectively. The mean cytotoxic concentrations for macrophages (CC50) were higher than those for amastigotes (341.95, 71.65, and 144.0 µg/mL, resp.), indicating a selective cytotoxicity towards the parasite rather than the macrophages. Interestingly, all treatments promoted antileishmanial effect against macrophage-internalized amastigotes at concentrations lower than CC50. Furthermore, increases of lysosomal volume of macrophages treated with EtOH-Ext, Hex-F, and Lupeol were observed. On the other hand, only Lupeol stimulated increase of phagocytic capability of macrophages, suggesting this compound might be characterized as the biomarker for the antileishmanial effect of P. insignis stem bark, as well as the involvement of immunomodulatory mechanisms in this effect.
Phytochemical investigation from carnauba (Copernicia prunifera) wax led to the identification of sixteen dammarane-type triterpenes, including thirteen new characterized as: (24R*)-methyldammara-20,25-dien-3α-ol and a mixture of alkyl (24R*)-methyldammar-25-en-20-ol-3β-carboxylates, together with three previously described triterpenes: carnaubadiol, (24R*)-methyldammara-20,25-dien-3β-ol and (24R*)-24-methyldammara-20,25-dien-3-one. Moreover, four fatty alcohols (eicosanol, docosanol, tetracosanol and hexacosanol) as well as four sterols (cholesterol, campesterol, stigmasterol, and sitosterol) were also obtained. These compounds were isolated using classical chromatographic methods and their structures were determined by spectroscopic and chemical methods.
Abstract:Previous investigations of H. oreadica reported the presence of a wide spectrum of complex limonoids and dihydrocinnamic acids. Our interest in the Rutaceae motivated a reinvestigation of H. oreadica, H. brasiliana and H. superba searching for other secondary metabolites present in substantial amounts for taxonomic analysis. In a continuation of the investigation of the H. oreadica, three new limonoids have now been isolated 9α-hydroxyhortiolide A, 11β-hydroxyhortiolide C and 1(S*)-acetoxy-7(R*)-hydroxy-7-deoxoinchangin. All the isolated compounds from the Hortia species reinforce its position in the Rutaceae. With regard to limonoids the genus produces highly specialized compounds, whose structural variations do not occur in any other member of the Rutaceae, thus, it is evident from limonoid data that Hortia takes an isolated position within the family. In addition, H. superba afforded the unexpected coumarin 5-chloro-8-methoxy-psoralen, which may not be a genuine natural product. Solid-state cross-polarisation/magic-anglespinning 13 C nuclear magnetic resonance, X-Ray fluorescence and Field-emission gun scanning electron microscopy experiments show that the Sephadex LH-20 was modified after treatment with NaOCl, suggesting that when xanthotoxin (8-methoxy-psoralen) was extracted from cleaning of the gel column, chlorination of the aromatic system occurred.
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