title: Antiprotozoal activity of extracts and isolated triterpenoids of 'carnauba' (Copernicia prunifera) wax from Brazil.
abstract: BACKGROUND
  '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.
  
  
  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 μg/mL in DMSO during 48 h at 24 °C) and amastigote (3-150 μg/mL in DMSO during 120 h at 37 °C) forms of Leishmania infantum as well as against trypomastigote (3-150 μg/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 μg/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*)-methyldammar-25-ene-3β,20-diol (carnaubadiol, 1), (24R*)-methyldammara-20,25-dien-3-one (2) and (24R*)-methyldammara-20,25-dien-3α-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 IC50values ranging from 8 to 52 μM, while compounds 1 and 3 displayed activity against trypomastigote forms of T. cruzi with IC50values of 15 and 35 μM, respectively. The mammalian cytotoxicity assay demonstrated no damage to NCTC conjunctive cells up to 200 μM, except for compound 1, which demonstrated a CC50value of 34 μM.
  
  
  CONCLUSIONS
  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.
authors: a Department of Chemistry , Federal University of Piauí , Teresina , PI , Brazil.
authors: Buana C
authors: BC
authors: de Almeida
authors: a Department of Chemistry , Federal University of Piauí , Teresina , PI , Brazil.
authors: Bruno Q
authors: BQ
authors: Araújo
authors: a Department of Chemistry , Federal University of Piauí , Teresina , PI , Brazil.
authors: Adonias A
authors: AA
authors: Carvalho
authors: a Department of Chemistry , Federal University of Piauí , Teresina , PI , Brazil.
authors: Sâmya Danielle L
authors: SD
authors: Freitas
authors: b Center of Natural Sciences and Humanities , Federal University of ABC , SP , Brazil.
authors: Dayany da S Alves
authors: DD
authors: Maciel
authors: c Chemical Studies Centre , University Centre of Osasco Teaching Institute Foundation , São Paulo , SP , Brazil.
authors: Ari José S
authors: AJ
authors: Ferreira
authors: d Centre for Parasitology and Mycology , Adolfo Lutz Institute , São Paulo , SP , Brazil.
authors: Andre G
authors: AG
authors: Tempone
authors: d Centre for Parasitology and Mycology , Adolfo Lutz Institute , São Paulo , SP , Brazil.
authors: Ligia F
authors: LF
authors: Martins
authors: d Centre for Parasitology and Mycology , Adolfo Lutz Institute , São Paulo , SP , Brazil.
authors: Tatiana R
authors: TR
authors: Alexandre
authors: a Department of Chemistry , Federal University of Piauí , Teresina , PI , Brazil.
authors: Mariana H
authors: MH
authors: Chaves
authors: b Center of Natural Sciences and Humanities , Federal University of ABC , SP , Brazil.
authors: João Henrique G
authors: JH
authors: Lago
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000302:isolation & purification / Q000494:pharmacology*; D001938:Brazil; D005260:Female; D018314:Leishmania infantum / Q000187:drug effects* / Q000502:physiology; D008647:Mesocricetus; D051379:Mice; D008807:Mice, Inbred BALB C; D010936:Plant Extracts / Q000302:isolation & purification / Q000494:pharmacology*; D014315:Triterpenes / Q000302:isolation & purification / Q000494:pharmacology*; D014885:Waxes / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D000981:Antiprotozoal Agents; D010936:Plant Extracts; D014315:Triterpenes; D014885:Waxes; C026344:carnauba wax
keywords: Chagas disease; Dammarane triterpenoids; Leishmania infantum; Trypanosoma cruzi; leishmaniasis