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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.)

Antitrypanosomal Lactones from Nectandra barbellata

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Author(s):
Londero, Vinicius S. [1] ; Costa-Silva, Thais A. [2] ; Antar, Guilherme M. [3] ; Baitello, Joao B. [4] ; de Oliveira, Larissa V. F. [1] ; Camilo, Fernanda F. [1] ; Batista, Andrea N. L. [5] ; Batista, Jr., Joao M. [6] ; Tempone, Andre G. [7] ; Lago, Joao Henrique G. [2]
Total Authors: 10
Affiliation:
[1] Univ Fed Sao Paulo, Inst Environm Chem & Pharmaceut Sci, BR-05508000 Sao Paulo - Brazil
[2] Fed Univ ABC, Ctr Nat & Human Sci, BR-09210170 Sao Paulo - Brazil
[3] Univ Sao Paulo, Inst Biosci, Dept Bot, BR-05508090 Sao Paulo - Brazil
[4] Inst Florestal, Dason Div, BR-02377000 Sao Paulo - Brazil
[5] Fluminense Fed Univ, Inst Chem, BR-24220900 Rio De Janeiro - Brazil
[6] Univ Fed Sao Paulo, Inst Sci & Technol, BR-12231280 Sao Paulo - Brazil
[7] Adolfo Lutz Inst, Ctr Parasitol & Mycol, BR-01246902 Sao Paulo - Brazil
Total Affiliations: 7
Document type: Journal article
Source: Journal of Natural Products; v. 84, n. 5, p. 1489-1497, MAY 28 2021.
Web of Science Citations: 1
Abstract

Twigs of Nectandra barbellata were extracted using a solution of the ionic liquid 1-butyl-3-methylimidazolium bromide (BMImBr) in H2YO, assisted by microwave (MAE). After successive chromatographic steps, one sesquiterpene, costic acid, and three new related lactones, (R)-3(7)-Z-3-hexadec-21-enylidene-5-(hydroxymethyl)tetrahydrofuran-2-one (1), (R)-3(7)-Z-3-hexadecylidene-5-(hydroxymethyl)tetrahydrofuran-2-one (2), and ( R)-3(7)-Z-3-docosylidene-5-(hydroxymethyl) tetrahydrofuran-2-one (3), were isolated. After structural elucidation using IR, UV, HRESIMS, NMR, ECD, and VCD, compounds 1-3 were tested against trypomastigote forms of Trypanosoma cruzi. The mechanism of action of bioactive isolated compounds was studied using different fluorescent-based approaches to investigate alterations of the plasma membrane, permeability/electric potential (Delta Psi(p)), reactive oxygen species levels, mitochondria (electric membrane potential, Delta Psi(m)/ATP levels), Ca2+ levels, and pH of the acidocalcisomes. In addition, in silico studies predicted no resemblance to pan assay interference compounds (PAINS). (AU)

FAPESP's process: 14/25222-9 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
Grantee:João Marcos Batista Junior
Support type: Research Grants - Young Investigators 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 type: BIOTA-FAPESP Program - Regular Research Grants
FAPESP's process: 17/17044-1 - Biomolecules from Nectandra barbellata Coe-Teixeira (Lauraceae): use of a sustainable alternative method for extraction, molecular characterization and evaluation of antiparasitic potential
Grantee:Vinicius Silva Londero
Support type: 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 type: Regular Research Grants
FAPESP's process: 21/02789-7 - Search for bioactive metabolites with antiparasitic action in plant species from Atlantic Forest and Cerrado regions - a chemical, phenotypical, and metabolomic approach
Grantee:João Henrique Ghilardi Lago
Support type: BIOTA-FAPESP Program - Regular Research Grants