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

Antileishmanial Acetylene Fatty Acid and Acetogenins from Seeds of Porcelia macrocarpa

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Author(s):
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Ivanildo A. Brito [1] ; Emerson A. Oliveira [2] ; Mariana H. Chaves [3] ; Fernanda Thevenard [4] ; André F. Rodrigues-Oliveira [5] ; Gustavo Barbosa-Reis [6] ; Patricia Sartorelli [7] ; Diogo Oliveira-Silva [8] ; Andre G. Tempone [9] ; Thais A. Costa-Silva [10] ; João Henrique G. Lago [11]
Total Authors: 11
Affiliation:
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[1] Universidade Federal do ABC. Centro de Ciências Naturais e Humanas - Brasil
[2] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Química - Brasil
[3] Universidade Federal do Piauí. Departamento de Química - Brasil
[4] Universidade Federal do ABC. Centro de Ciências Naturais e Humanas - Brasil
[5] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Química - Brasil
[6] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Química - Brasil
[7] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Química - Brasil
[8] Universidade Federal de São Paulo. Instituto de Ciências Ambientais, Químicas e Farmacêuticas. Departamento de Química - Brasil
[9] Instituto Adolfo Lutz. Centro de Parasitologia e Micologia - Brasil
[10] Universidade Federal do ABC. Centro de Ciências Naturais e Humanas - Brasil
[11] Universidade Federal do ABC. Centro de Ciências Naturais e Humanas - Brasil
Total Affiliations: 11
Document type: Journal article
Source: Journal of the Brazilian Chemical Society; v. 32, n. 2, p. 447-453, 2021-02-01.
Abstract

In the present work five acetylene derivatives (1-5), including three unknowns (1, 3 and 4), were isolated from seeds of Porcelia macrocarpa (Annonaceae). The structures of isolated compounds were determined as docos-13-yn-21-enoic acid (1), 3-hydroxy-4-methylene-2-(eicos-11’-yn-19’-enyl)but-2-enolide (2), 3-hydroxy-4-methylene-2-(octadec-9’-yn-17’-enyl)but-2-enolide (3), 3-hydroxy-4-methylene-2-(hexadec-7’-yn-15’-enyl)but-2-enolide (4), and (2S,3R,4R)-3-hydroxy-4-methyl-2-(eicos-11’-yn-19’-enyl)butanolide (5) by analysis of nuclear magnetic resonance (NMR) and electrospray ionization high-resolution mass spectrometry (ESI-HRMS) data. Moreover, all isolated compounds demonstrated selectivity towards intracellular amastigotes of Leishmania (L.) infantum, especially 2-4 with 50% inhibitory concentration (IC50) values of 9.2, 10.4 and 11.0 µM, respectively, indicating superior activity of that determined to positive control miltefosine (IC50 of 17.8 µM). Furthermore, these compounds showed higher selectivity index (SI) in comparison with miltefosine. Since related acetylene fatty acid 1 displayed reduced antiparasitic potential (IC50 of 48.5 µM), the obtained results suggested that the γ-lactone plays an important role in the antileishmanial activity. However, 2-4 exhibited cytotoxicity to mammalian NCTC cells (CC50 ca. 80 µM), which could be a result of the presence of a conjugated carbonyl system in the lactone ring, since 5, the only acetogenin that presents the saturated ring, lacked mammalian cytotoxicity (CC50 > 200 µM). (AU)

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: 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