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Title

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

Authors
Rocha, Vinicius P. C.
Bastos, Tanira M.
da Rocha, Cláudia Q.
Grimaldi, Gabriela B.
de Sousa, Karoline A. F.
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Published in Journal of Natural Products. 2020, vol. 83, no. 9, p. 2631-2640
Abstract 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.
Keywords Natural productsArrabidaea brachypodaHalogenationUHPLC-PDA-ELSD-MSIsolationStructural elucidationLeishmania amazonensisTrypanosoma cruzi
Identifiers
PMID: 32902988
Full text
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Other version: https://pubs.acs.org/doi/10.1021/acs.jnatprod.0c00433
Structures
Research group Phytochimie et produits naturels bioactifs
Project
FNS: 205321_182438/1
Citation
(ISO format)
NEUENSCHWANDER, Alexandra et al. Production of Highly Active Antiparasitic Compounds from the Controlled Halogenation of the Arrabidaea brachypoda Crude Plant Extract. In: Journal of Natural Products, 2020, vol. 83, n° 9, p. 2631-2640. doi: 10.1021/acs.jnatprod.0c00433 https://archive-ouverte.unige.ch/unige:144728

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Deposited on : 2020-11-16

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