Article Dans Une Revue Phytochemistry Année : 2026

Targeted discovery of sesquiterpene indole alkaloids from Greenwayodendron suaveolens

Résumé

Throughout the past decades, annonaceous plants have been of particular interest to the natural product community because of their therapeutic value and their richness in isoquinoline alkaloids. Taking advantage from our laboratory historical collection of these compounds, a MS/MS database of 322 isoquinolines and other metabolites from Annonaceae was implemented and named IQAMDB. The present report describes the dereplication of known alkaloids from stem barks of Greenwayodendron suaveolens (Engl. & Diels) Verdc. leveraging IQAMDB-informed feature-based molecular networking further refined by in silico annotation and taxonomic weighting. This strategy annotated over 30 compounds and streamlined the isolation of three sesquiterpene indole alkaloids (SIA) (1–3). Structure elucidation and absolute configuration assignment by a combination of NMR, TDDFT-ECD or X-ray diffraction determined these compounds to be greenwaylactam D (1) and greenwaylactam E (2), previously undescribed Witkop-Winterfeldt oxidized diastereoisomers of the previously reported greenwaylactam A, and polyveodrine (3), that discloses an unprecedented relative configuration for a SIA. The isolated compounds were evaluated for their antibacterial and antifungal activities against Staphylococcus aureus, Pseudomonas aeruginosa, Candida albicans, Mycobacterium marinum as well as their antiviral activity against Zika virus. Polyveodrine exhibited moderate antimycobacterial activity against M. marinum, whereas greenwaylactam D (1) demonstrated moderate antiviral activity against Zika virus under non-cytotoxic concentrations. Graphical abstract Three new sesquiterpene indole alkaloids were targeted following a MS-based dereplicative logic and subsequently isolated from stem barks of Greenwayodendron suaveolens. The structure elucidation relied on a combination of spectroscopic techniques and computational methods. The isolated compounds were evaluated for their anti-infective activity.

DOI

Cite 10.5281/zenodo.15789673 Jeu de données Beniddir, M., & Mbeng Obame, R. B. (2025). TIMA annotation of Greenwayodendron suaveolens stem bark extract (DCM-MeOH) [Data set]. Zenodo. https://doi.org/10.5281/ZENODO.15789673

Tima parameters and annotation results are accessible on the Zenodo repository under the identifier
DOI

Cite 10.5281/zenodo.15789976 Jeu de données Beniddir, M. (2025). Sesquiterpene indole alkaloids geometric and frequency calculation Gaussian files [Data set]. Zenodo. https://doi.org/10.5281/ZENODO.15789976

Cartesian coordinates of the conformations generated for compounds 1–3 are accessible as genuine Gaussian file outputs (.log) on the Zenodo repository under the identifier
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Dates et versions

hal-05327820 , version 1 (23-10-2025)

Identifiants

Citer

Rany Mbeng Obame, Pierre Le Pogam, Karine Leblanc, Somia Rharrabti, Evodie Numbi Wa Ilunga, et al.. Targeted discovery of sesquiterpene indole alkaloids from Greenwayodendron suaveolens. Phytochemistry, 2026, 241, pp.114664. ⟨10.1016/j.phytochem.2025.114664⟩. ⟨hal-05327820⟩
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