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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Alves Conserva, Geanne A. [1] ; Quiros-Guerrero, Luis M. [2, 3] ; Costa-Silva, Thais A. [1] ; Marcourt, Laurence [2, 3] ; Pinto, Erika G. [4] ; Tempone, Andre G. [5] ; Fernandes, Joao Paulo S. [6] ; Wolfender, Jean-Luc [2, 3] ; Queiroz, Emerson F. [2, 3] ; Lago, Joao Henrique G. [1]
Total Authors: 10
[1] Fed Univ ABC, Ctr Nat Sci & Humanities, Santo Andre, SP - Brazil
[2] Univ Geneva, Sch Pharmaceut Sci, Geneva - Switzerland
[3] Univ Geneva, Inst Pharmaceut Sci Western Switzerland, Geneva - Switzerland
[4] Univ Dundee, Sch Life Sci, Drug Discovery Unit, Dundee - Scotland
[5] Adolfo Lutz Inst, Ctr Parasitol & Mycol, Sao Paulo - Brazil
[6] Univ Fed Sao Paulo, Dept Pharmaceut Sci, Diadema, SP - Brazil
Total Affiliations: 6
Document type: Journal article
Source: PLoS One; v. 16, n. 2 FEB 25 2021.
Web of Science Citations: 1

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 CH2Cl2 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 CH2Cl2 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 EC50 value of 18.1 mu M, similar to positive control benznidazole (18.7 mu M). 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 EC50 values from 20.4 to 11.7 mu M, 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. (AU)

FAPESP's process: 18/18975-1 - Dereplication profile of Nectandra oppositifolia Nees & Mart. (Lauraceae): identification and molecular characterization of antiparasitic metabolites
Grantee:Geanne Alexsandra Alves Conserva
Support Opportunities: Scholarships abroad - Research Internship - Doctorate
FAPESP's process: 18/07885-1 - Biomolecules from plant species of remnant areas of the Atlantic Forest and Cerrado to treat neglected tropical diseases - chemical and pharmacological aspects
Grantee:João Henrique Ghilardi Lago
Support Opportunities: BIOTA-FAPESP Program - Regular Research Grants
FAPESP's process: 16/20633-6 - Bioactive metabolites from Nectandra oppositifolia Nees & Mart. (Lauraceae): molecular characterization, in vitro and in vivo antiparasitic potential evaluation and determination of mechanism of action
Grantee:Geanne Alexsandra Alves Conserva
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 18/10279-6 - Selection and Optimization of New Drug Candidates for Leishmaniasis and Chagas Disease
Grantee:André Gustavo Tempone Cardoso
Support Opportunities: Regular Research Grants
FAPESP's process: 15/23403-9 - Rational Pre-Clinical Study of New Drug Candidates Against Neglected Protozoan Diseases Using Pharmacokinetic Approaches
Grantee:André Gustavo Tempone Cardoso
Support Opportunities: Regular Research Grants