Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/33251
Title: Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis
Authors: Cargnin, Simone Tasca
Staudt, Andressa Finkler
Santos, Ana Paula de Azevedo dos
Gosmann, Grace
Teles, Carolina Bioni Garcia
Gnoatto, Simone Baggio
Affilliation: Universidade Federal do Rio Grande do Sul. Laboratório de Fitoquímica e Síntese Orgânica. Porto Alegre, RS, Brasil.
Universidade Federal do Rio Grande do Sul. Laboratório de Fitoquímica e Síntese Orgânica. Porto Alegre, RS, Brasil.
Fundação Oswaldo Cruz. Fiocruz Rondônia. Laboratório da Plataforma de Bioensaios de Malária e Leishmaniose. Porto Velho, RO, Brasil.
Universidade Federal do Rio Grande do Sul. Laboratório de Fitoquímica e Síntese Orgânica. Porto Alegre, RS, Brasil.
Fundação Oswaldo Cruz. Fiocruz Rondônia. Laboratório da Plataforma de Bioensaios de Malária e Leishmaniose. Porto Velho, RO, Brasil.
Universidade Federal do Rio Grande do Sul. Laboratório de Fitoquímica e Síntese Orgânica. Porto Alegre, RS, Brasil.
Abstract: Pentacyclic triterpenes, especially ursolic and betulinic acid, are extracted eco-friendly from natural sources and are biologically active compounds. Semisynthesis tools have been employed in order to improve their biological activities. The bromination reaction could influence in the conformational structure of triterpenes skeleton and consequently, in their biological activity. In this work, we aim to survey and discuss an effective approach for semi-synthesis reactions to obtain betulinic acid (BA) and ursolic acid (UA) brominated derivatives and to evaluate their effects on viability of promastigote forms of Leishmania amazonensis. The bromination reaction protocol using N-bromosuccinimide (NBS) reagent was adapted for both triterpenes, aiming to obtain UA C12-Br and BA C30-Br modifications. The evaluation of leishmanicidal potential was performed using promastigotes forms of Leishmania (Leishmania) amazonensis and the viability was measured by MTT assay. According to spectroscopic data, the semi-synthesis of brominated triterpene derivatives using the methodology proposed was successfully accomplished. Bromination of the triterpene structures resulted in an increased antileishmanial activity comparing with the natural precursors, UA and BA. This report brings forth the discussion about the UA bromolactonization and BA C30-Br derivative semi-synthesis and characterization, and reports for the first time the activity of these derivatives on the viability of L. amazonensis, causative agent of leishmaniasis, a neglected tropical disease.
Keywords: Triterpenes
Ursolic acid
Betulinic acid
Bromination reaction
Leishmania amazonensis
Issue Date: 2017
Publisher: Annals of Medicinal Chemistry and Research
Citation: CARGNIN, Simone Tasca et al. Effective Approach to Semi-Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis. Annals of Medicinal Chemistry and Research, p. 1-5, 2017.
ISSN: 2378-9336
Copyright: open access
Appears in Collections:RO - Artigos de Periódicos




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