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EtOH extracts from the leaves and twigs of  Nectandra oppositifolia  Nees & Mart. shown activity against amastigote forms of  Trypanosoma cruzi . These extracts were subjected to successive liquid-liquid partitioning to afford bioactive CH 2 Cl 2  fractions. UHPLC-TOF-HRMS/MS and molecular networking were used to obtain an overview of the phytochemical composition of these active fractions. Aiming to isolate the active compounds, both CH 2 Cl 2  fractions were subjected to fractionation using medium pressure chromatography combined with semi-preparative HPLC-UV. Using this approach, twelve compounds ( 1 – 12 ) were isolated and identified by NMR and HRMS analysis. Several isolated compounds displayed activity against the amastigote forms of  T .  cruzi , especially ethyl protocatechuate ( 7 ) with EC 50  value of 18.1 μM, similar to positive control benznidazole (18.7 μM). Considering the potential of compound  7 , protocatechuic acid and its respective methyl ( 7a ),  n -propyl ( 7b ),  n -butyl ( 7c ),  n -pentyl ( 7d ), and  n -hexyl ( 7e ) esters were tested. Regarding antitrypanosomal activity, protocatechuic acid and compound  7a  were inactive, while  7b-7e  exhibited EC 50  values from 20.4 to 11.7 μM, without cytotoxicity to mammalian cells. These results suggest that lipophilicity and molecular complexity play an important role in the activity while efficiency analysis indicates that the natural compound  7  is a promising prototype for further modifications to obtain compounds effective against the intracellular forms of  T .  cruzi .

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Metabolite profile of Nectandra oppositifolia Nees &amp; Mart. and assessment of antitrypanosomal activity of bioactive compounds through efficiency analyses