Psilostachyins as trypanocidal compounds: Bioguided fractionation of Ambrosia tenuifolia chemically modified extract

This work focusses on the chemical diversification of an Ambrosia tenuifolia extract and its bioguided fractionation, aiming to unveil the chemical entity responsible for the trypanocidal activity. Besides, a revision of the phytochemical study of this species, based on previous reports of the antip...

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Published in:Phytochemistry (Oxford) 2022-02, Vol.194, p.113014-113014, Article 113014
Main Authors: Adessi, Tonino G., Ana, Yamile, Stempin, Cinthia C., García, Mónica C., Bisogno, Fabricio R., Nicotra, Viviana E., García, Manuela E.
Format: Article
Language:English
Subjects:
Ambrosia
Ambrosia tenuifolia
Asteraceae
Bioguided fractionation
Extract modifications
Plant Extracts
Psilostachyins
Sesquiterpene lactones
Structure activity relationships
Trypanocidal compounds
Trypanosoma cruzi
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Summary:This work focusses on the chemical diversification of an Ambrosia tenuifolia extract and its bioguided fractionation, aiming to unveil the chemical entity responsible for the trypanocidal activity. Besides, a revision of the phytochemical study of this species, based on previous reports of the antiparasitic psilostachyins A and C as main compounds, was conducted. To improve the biological properties of a plant extract through a simple chemical reaction, the oxidative diversification of the dichloromethane extract of this plant species was carried out. A bioguided fractionation of a chemically modified extract was performed by evaluating the inhibitory activity against Trypanosoma cruzi trypomastigotes. This experiment led to the isolation of one of the most active compounds. In general terms, epoxidized metabolites were obtained as a result of the oxidation of the major metabolite of the species. The trypanocidal activity of some tested metabolites overperformed the reference drug, benznidazole, displaying no cytotoxicity at trypanocidal concentrations. Key structure-activity relationships were obtained for designing previously undescribed antiparasitic sesquiterpene lactones. [Display omitted] •Chemical diversification and bioguided fractionation of Ambrosia tenuifolia extract.•Evaluation of inhibitory activity against Trypanosoma cruzi trypomastigotes.•The trypanocidal activity of some metabolites over performed the reference drug.•The configuration of the epoxidized derivatives is key to increases the inhibition.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2021.113014