2. Academic Validation
  3. Caatinga plants: Natural and semi-synthetic compounds potentially active against Trichomonas vaginalis

Caatinga plants: Natural and semi-synthetic compounds potentially active against Trichomonas vaginalis

  • Bioorg Med Chem Lett. 2016 May 1;26(9):2229-36. doi: 10.1016/j.bmcl.2016.03.061.
Patrícia de Brum Vieira 1,  Nícolas Luiz Feijó Silva 2,  Gloria Narjara Santos da Silva 3,  Denise Brentan Silva 4,  Norberto Peporine Lopes 5,  Simone Cristina Baggio Gnoatto 6,  Márcia Vanusa da Silva 7,  Alexandre José Macedo 8,  Jaume Bastida 9,  Tiana Tasca 10
Affiliations

Affiliations

  • 1 Laboratório de Pesquisa em Parasitologia, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS 90610-000, Brazil. Electronic address: patriciasbrum@yahoo.com.br.
  • 2 Laboratório de Pesquisa em Parasitologia, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS 90610-000, Brazil. Electronic address: nicolaslfsilva@gmail.com.
  • 3 Laboratório de Fitoquímica e Síntese Orgânica, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS 90610-000, Brazil. Electronic address: narjarags@gmail.com.
  • 4 Laboratório de Produtos Naturais e Espectrometria de Massas (LAPNEM), Universidade Federal de Mato Grosso do Sul (UFMS), Campo Grande, MS 79090-900, Brazil; Núcleo de Pesquisas em Produtos Naturais e Sintéticos, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP 14040-903, Brazil. Electronic address: denise.brentan@ufms.com.
  • 5 Núcleo de Pesquisas em Produtos Naturais e Sintéticos, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP 14040-903, Brazil. Electronic address: npelopes@fcfrp.usp.b.
  • 6 Laboratório de Fitoquímica e Síntese Orgânica, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS 90610-000, Brazil. Electronic address: simone.gnoatto@ufrgs.br.
  • 7 Centro de Ciências Biológicas e Departamento de Bioquímica, Universidade Federal de Pernambuco, Recife, PE 50670-901, Brazil. Electronic address: Marcia.vanusa@ufpe.br.
  • 8 Faculdade de Farmácia e Centro de Biotecnologia, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS 90610-000, Brazil; Instituto Nacional do Semi-Árido (INSA), Núcleo de Biprospecção da Caatinga (NBioCaat), Campina Grande, Pernambuco, Brazil. Electronic address: Alexandre.jose.macedo@gmail.com.
  • 9 Department of Natural Products, Plant Biology and Soil Science, Faculty of Pharmacy, University of Barcelona, Barcelona, Catalonia 08028, Spain. Electronic address: jaumebastida@ub.edu.
  • 10 Laboratório de Pesquisa em Parasitologia, Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS 90610-000, Brazil; Instituto Nacional do Semi-Árido (INSA), Núcleo de Biprospecção da Caatinga (NBioCaat), Campina Grande, Pernambuco, Brazil. Electronic address: tiana.tasca@ufrgs.br.
PMID: 27020521 DOI: 10.1016/j.bmcl.2016.03.061
Abstract

Trichomonas vaginalis causes trichomoniasis; the most common but overlooked non-viral sexually transmitted disease worldwide. The treatment is based at 5'-nitroimidazoles, however, failure are related to resistance of T. vaginalis to chemotherapy. Caatinga is a uniquely Brazilian region representing a biome with type desert vegetation and Plants present diverse biological activity, however, with few studies. The aim of this study was to investigate the activity against T. vaginalis of different Plants from Caatinga and identify the compounds responsible by the activity. A bioguided fractionation of Manilkara rufula was performed and four major compounds were identified: caproate of α-amyrin (1b), acetate of β-amyrin (2a), caproate of β-amyrin (2b), and acetate of lupeol (3a). In addition, six derivatives of α-amyrin (1), β-amyrin (2) and lupeol (3) were synthesized and tested against the Parasite. Ursolic acid (5) reduced about 98% of Parasite viability after 2h of incubation and drastic ultrastructural alterations were observed by scanning electron microscopy. Moreover, 5 presented high cytotoxicity to HMVII and HeLa cell line and low cytotoxicity against Vero line at 50 μM (MIC against the Parasite). Metronidazole effect against T. vaginalis resistant isolate was improved when in association with 5.

Keywords

Caatinga plants; Cytotoxicity; Trichomonas vaginalis; Triterpenes; Ursolic acid.

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