Production of Highly Active Antiparasitic Compounds from the Controlled Halogenation of the <i>Arrabidaea brachypoda</i> Crude Plant Extract

Article Article scientifique Article Production of Highly Active Antiparasitic Compounds from the Controlled Halogenation of the <i>Arrabidaea brachypoda</i> Crude Plant Extract eng 2020 author Neuenschwander Alexandra 755148 author Rocha Vinicius P. C. author Bastos Tanira M. author Marcourt Laurence 729234 author Morin Hugo 0000-0003-3969-2406 855532 author da Rocha Cláudia Q. author Grimaldi Gabriela B. author de Sousa Karoline A. F. author Borges Jadson N. author Rivara-Minten Elisabeth 23985 author Wolfender Jean-Luc 135649 author Soares Milena B. P. author Ferreira Queiroz Emerson 135675 2631-2640 10.1021/acs.jnatprod.0c00433 32902988 0163-3864 https://pubs.acs.org/doi/10.1021/acs.jnatprod.0c00433 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. Natural products Arrabidaea brachypoda Halogenation UHPLC-PDA-ELSD-MS Isolation Structural elucidation Leishmania amazonensis Trypanosoma cruzi Dewey 615 Swiss National Science Foundation Improving natural products chemical biodiversity for drug discovery by fungal secretome assisted biotransformation 205321_182438 CH Project funding 31 Section des sciences pharmaceutiques 17 false 882 Phytochimie et produits naturels bioactifs Journal of Natural Products 83 9 8ddef963-4c1d-4b86-950d-8945ff6bcfab Article (Accepted version) Public NeuenschwanderJNP2020.pdf 1236741 application/pdf Restricted 2021-09-28 69cea02f-f74b-44a1-968a-b81acbfaa23b Article (Published version) Restricted Neuenschwander2020.pdf 1457532 application/pdf openAccess Faculté des sciences / Section des sciences pharmaceutiques

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Production of Highly Active Antiparasitic Compounds from the Controlled Halogenation of the Arrabidaea brachypoda Crude Plant Extract	Journal of Natural Products			2020	278	297

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Neuenschwander, Alexandra