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

Alexandra Neuenschwander | Zendy; Vinícius Pinto Costa Rocha | Zendy; Tanira Matutino Bastos | Zendy; Laurence Marcourt | Zendy; Hugo Morin | Zendy; Cláudia Quintino da Rocha | Zendy; G. Grimaldi | Zendy; Karoline Almeida Félix de Sousa | Zendy; Jadson N. Borges | Zendy; Elisabeth RivaraMinten | Zendy; JeanLuc Wolfender | Zendy; Milena Botelho Pereira Soares | Zendy; Emerson Ferreira Queiroz | Zendy

Open Access

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

Author(s) -

Alexandra Neuenschwander,

Vinícius Pinto Costa Rocha,

Tanira Matutino Bastos,

Laurence Marcourt,

Hugo Morin,

Cláudia Quintino da Rocha,

G. Grimaldi,

Karoline Almeida Félix de Sousa,

Jadson N. Borges,

Elisabeth RivaraMinten,

JeanLuc Wolfender,

Milena Botelho Pereira Soares,

Emerson Ferreira Queiroz

Publication year - 2020

Publication title -

journal of natural products

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.976

H-Index - 139

eISSN - 1520-6025

pISSN - 0163-3864

DOI - 10.1021/acs.jnatprod.0c00433

Subject(s) - halogenation , antiparasitic , antiparasitic agent , chemistry , organic chemistry , chromatography , anthraquinones , biology , botany , medicine , pathology , pharmacology

Direct halogenation of phenolic compounds present in the CH 2 Cl 2 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 IC 50 values comparable to the reference were identified.

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