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Production of Highly Active Antiparasitic Compounds from the Controlled Halogenation of the Arrabidaea brachypoda Crude Plant Extract.
Journal article

Production of Highly Active Antiparasitic Compounds from the Controlled Halogenation of the Arrabidaea brachypoda Crude Plant Extract.

  • Neuenschwander A School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland (ISPSW), University of Geneva, CMU, Rue Michel Servet 1, 1211 Geneva 4, Switzerland.
  • Rocha VPC Laboratório de Engenharia Tecidual e Imunofarmacologia. Instituto Gonçalo Moniz, FIOCRUZ, Rua Waldemar Falcão, 121, Candeal, Salvador, BA 40296-710, Brazil.
  • Bastos TM Laboratório de Engenharia Tecidual e Imunofarmacologia. Instituto Gonçalo Moniz, FIOCRUZ, Rua Waldemar Falcão, 121, Candeal, Salvador, BA 40296-710, Brazil.
  • Marcourt L School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland (ISPSW), University of Geneva, CMU, Rue Michel Servet 1, 1211 Geneva 4, Switzerland.
  • Morin H School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland (ISPSW), University of Geneva, CMU, Rue Michel Servet 1, 1211 Geneva 4, Switzerland.
  • da Rocha CQ Laboratório de Produtos Naturais, Centro de Ciência Exatas e Tecnologia, Departamento de Química, Avenida dos Portugueses 1966, Bacanga, São Luís, Maranhão, MA 65080-805, Brazil.
  • Grimaldi GB Laboratório de Engenharia Tecidual e Imunofarmacologia. Instituto Gonçalo Moniz, FIOCRUZ, Rua Waldemar Falcão, 121, Candeal, Salvador, BA 40296-710, Brazil.
  • de Sousa KAF Laboratório de Engenharia Tecidual e Imunofarmacologia. Instituto Gonçalo Moniz, FIOCRUZ, Rua Waldemar Falcão, 121, Candeal, Salvador, BA 40296-710, Brazil.
  • Borges JN Laboratório de Engenharia Tecidual e Imunofarmacologia. Instituto Gonçalo Moniz, FIOCRUZ, Rua Waldemar Falcão, 121, Candeal, Salvador, BA 40296-710, Brazil.
  • Rivara-Minten E School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland (ISPSW), University of Geneva, CMU, Rue Michel Servet 1, 1211 Geneva 4, Switzerland.
  • Wolfender JL School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland (ISPSW), University of Geneva, CMU, Rue Michel Servet 1, 1211 Geneva 4, Switzerland.
  • Soares MBP Laboratório de Engenharia Tecidual e Imunofarmacologia. Instituto Gonçalo Moniz, FIOCRUZ, Rua Waldemar Falcão, 121, Candeal, Salvador, BA 40296-710, Brazil.
  • Queiroz EF School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland (ISPSW), University of Geneva, CMU, Rue Michel Servet 1, 1211 Geneva 4, Switzerland.
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  • 2020-09-09
Published in:
  • Journal of natural products. - 2020
Organic Chemistry
Complementary and alternative medicine
Analytical Chemistry
Molecular Medicine
Pharmacology
Drug Discovery
Pharmaceutical Science
English Direct halogenation of phenolic compounds present in the CH2Cl2 extract of the roots of Arrabidaea brachypoda was investigated to enhance chemodiversity. The approach is based on eco-friendly reactions using NaBr, NaI, and NaCl in aqueous media to generate multiple "unnatural" halogenated natural products from crude extracts. The halogenation reactions, monitored by UHPLC-PDA-ELSD-MS, were optimized to generate mono-, di-, or trihalogenated derivatives. To isolate these compounds, the reactions were scaled up and the halogenated analogues were isolated by semipreparative HPLC-UV and fully characterized by NMR and HR-MS data. All of the original 16 halogenated derivatives were evaluated for their antiparasitic activities against the parasites Leishmania amazonensis and Trypanosoma cruzi. Compounds presenting selective antiparasitic activities against one or both parasites with IC50 values comparable to the reference were identified.
Language
  • English
Open access status
closed
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Persistent URL
https://sonar.ch/global/documents/252285
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