Twigs of were extracted using a solution of the ionic liquid 1-butyl-3-methylimidazolium bromide (BMImBr) in HO, assisted by microwave (MAE). After successive chromatographic steps, one sesquiterpene, costic acid, and three new related lactones, 3(7)--3-hexadec-21-enylidene-5-(hydroxymethyl)tetrahydrofuran-2-one (), 3(7)--3-hexadecylidene-5-(hydroxymethyl)tetrahydrofuran-2-one (), and 3(7)--3-docosylidene-5-(hydroxymethyl)tetrahydrofuran-2-one (), were isolated. After structural elucidation using IR, UV, HRESIMS, NMR, ECD, and VCD, compounds were tested against trypomastigote forms of . 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 (ΔΨ), reactive oxygen species levels, mitochondria (electric membrane potential, ΔΨ/ATP levels), Ca levels, and pH of the acidocalcisomes. In addition, in silico studies predicted no resemblance to pan assay interference compounds (PAINS).
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http://dx.doi.org/10.1021/acs.jnatprod.0c01303 | DOI Listing |
Phytochemistry
December 2024
Centre for Natural and Human Sciences, Federal University of ABC, Santo Andre, SP, 09280-560, Brazil. Electronic address:
As part of our continuous study on the Annonaceae species Porcelia macrocarpa, in the present work, eight chemically related 2-alkyl-3-hydroxy-4-methyl-γ-lactones (1-8) were isolated. Their structures were characterised by NMR, MS, and VCD. Their antitrypanosomal activity was evaluated in vitro against intracellular amastigotes with EC values ranged from 13.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
Max-Planck-Institut für Kohlenforschung, 45470, Mülheim/Ruhr, Germany.
The strasseriolide macrolides show promising in vitro and in vivo activities against P. falciparum and T. cruzi, the parasites causing malaria and Chagas disease, respectively.
View Article and Find Full Text PDFChem Biodivers
March 2024
Departamento de Química, Universidade Estadual de Maringá, 87020-900, Maringá - PR, Brasil.
Sesquiterpene lactones are an important class of secondary metabolites frequently isolated from Lessingianthus genus that present a variety of biological properties, such as antimalarial, anti-inflammatory, antileishmanial, antitrypanosomal and anticancer. The limited phytochemical studies and the importance of this class of compounds isolated from Lessingianthus led us to study this genus. In this work, we focused on the phytochemical investigation and dereplication based on UHPLC-HRMS/MS and molecular networking of L.
View Article and Find Full Text PDFJ Nat Prod
November 2023
Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
Vet Med Sci
November 2022
Faculty of Veterinary Medicine, Shahrekord Branch, Islamic Azad University, Shahrekord, Iran.
Background: The existing drug treatments for trypanosomiases are limited and suffer from shortcomings due to their toxicity and the emergence of resistant parasites. Developing anti-trypanosomal compounds based on natural products is a promising way of fighting trypanosomiases.
Objectives: This study aims to identify through scientific review a large variety of medicinal plants (anti-trypanosomal) used worldwide and scientifically shown to display anti-trypanosomal effects.
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