{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,22]],"date-time":"2025-11-22T11:13:07Z","timestamp":1763809987615,"version":"build-2065373602"},"reference-count":52,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2019,2,21]],"date-time":"2019-02-21T00:00:00Z","timestamp":1550707200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","award":["310608\/2013-9","Universal; 483894\/2012-5"],"award-info":[{"award-number":["310608\/2013-9","Universal; 483894\/2012-5"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Chemotherapy is limited in the treatment of leishmaniasis due to the toxic effects of drugs, low efficacy of alternative treatments, and resistance of the parasite. This work assesses the in vitro activity of flavopereirine on promastigote cultures of Leishmania amazonensis. In addition, an in silico evaluation of the physicochemical characteristics of this alkaloid is performed. The extract and fractions were characterized by thin-layer chromatography and HPLC-DAD, yielding an alkaloid identified by NMR. The antileishmanial activity and cytotoxicity were assayed by cell viability test (MTT). The theoretical molecular properties were calculated on the Molinspiration website. The fractionation made it possible to isolate a beta-carboline alkaloid (flavopereirine) in the alkaloid fraction. Moreover, it led to obtaining a fraction with greater antileishmanial activity, since flavopereirine is very active. Regarding the exposure time, a greater inhibitory effect of flavopereirine was observed at 24 h and 72 h (IC50 of 0.23 and 0.15 \u03bcg\/mL, respectively). The extract, fractions, and flavopereirine presented low toxicity, with high selectivity for the alkaloid. Furthermore, flavopereirine showed no violation of Lipinski\u2019s rule of five, showing even better results than the known inhibitor of oligopeptidase B, antipain, with three violations. Flavopereirine also interacted with residue Tyr-499 of oligopeptidase B during the molecular dynamics simulations, giving a few insights of a possible favorable mechanism of interaction and a possible inhibitory pathway. Flavopereirine proved to be a promising molecule for its antileishmanial activity.<\/jats:p>","DOI":"10.3390\/molecules24040785","type":"journal-article","created":{"date-parts":[[2019,2,22]],"date-time":"2019-02-22T03:49:44Z","timestamp":1550807384000},"page":"785","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Flavopereirine\u2014An Alkaloid Derived from Geissospermum vellosii\u2014Presents Leishmanicidal Activity In Vitro"],"prefix":"10.3390","volume":"24","author":[{"given":"Jo\u00e3o Victor","family":"da Silva e Silva","sequence":"first","affiliation":[{"name":"Post-Graduate Program in Pharmaceutical Sciences, Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"},{"name":"Laboratory of Immunomodulation and Protozoology, Oswaldo Cruz Institute, FIOCRUZ, Rio de Janeiro,  RJ 21040-900, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Helliton Patrick","family":"Cordovil Brigido","sequence":"additional","affiliation":[{"name":"Post-Graduate Program in Pharmaceutical Innovation, Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kelly Cristina","family":"Oliveira de Albuquerque","sequence":"additional","affiliation":[{"name":"Post-Graduate Program in Pharmaceutical Sciences, Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Josiwander","family":"Miranda Carvalho","sequence":"additional","affiliation":[{"name":"College of Chemistry, Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6969-6067","authenticated-orcid":false,"given":"Jordano","family":"Ferreira Reis","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lara","family":"Vinhal Faria","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"M\u00e1rlia Regina","family":"Coelho-Ferreira","sequence":"additional","affiliation":[{"name":"Em\u00edlio Goeldi Paraense Museum, Coordination of Botany, Ministry of Science, Technology, Innovation and Communications, Bel\u00e9m,  PA 66077-530, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fernando Tobias","family":"Silveira","sequence":"additional","affiliation":[{"name":"Evandro Chagas Institute, National Health Foundation, BR-316 Highway km 7, Ananindeua,  PA 67030-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Agnaldo","family":"da Silva Carneiro","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sandro","family":"Perc\u00e1rio","sequence":"additional","affiliation":[{"name":"US Centers for Disease Control and Prevention (CDC), Atlanta,  GA 30329, USA"},{"name":"Oxidative Stress Research Lab, Institute of Biological Sciences (ICB), Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrey Moacir","family":"do Ros\u00e1rio Marinho","sequence":"additional","affiliation":[{"name":"College of Chemistry, Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0804-5804","authenticated-orcid":false,"given":"Maria F\u00e2ni","family":"Dolabela","sequence":"additional","affiliation":[{"name":"Post-Graduate Program in Pharmaceutical Sciences, Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"},{"name":"Post-Graduate Program in Pharmaceutical Innovation, Federal University of Par\u00e1, Bel\u00e9m,  PA 66075-110, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,2,21]]},"reference":[{"key":"ref_1","first-page":"87f","article-title":"Conhecimento, uso e conserva\u00e7\u00e3o da diversidade vegetal em quatro comunidades ribeirinhas no munic\u00edpio Manacapuru, Amazonas","volume":"xiv","year":"2014","journal-title":"Instituto Nacional de Pesquisas da Amaz\u00f4nia"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"325","DOI":"10.1590\/S0074-02762004000300015","article-title":"Anti-leishmanial activity of alkaloidal extract from Aspidosperma ramiflorum","volume":"99","author":"Ferreira","year":"2004","journal-title":"Mem. 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