Sylla, Balla; Jost, Gilles; Lavoie, Serge; Legault, Jean; Gauthier, Charles 
ORCID: https://orcid.org/0000-0002-2475-2050 et Pichette, Andre
(2024).
Synthesis and cytotoxicity evaluation of D- and L-sugar-containing mono- and bidesmosidic ursane-type saponins
Bioorganic and Medicinal Chemistry
, vol. 106
, nº 117737.
pp. 1-15.
DOI: 10.1016/j.bmc.2024.117737.
Résumé
Ursolic acid and uvaol are naturally occurring triterpenoids that exhibit a broad spectrum of pharmacological activities, including cytotoxicity. However, a primary challenge in the development of ursane-type pentacyclic triterpenoids for pharmacological use is their poor aqueous solubility, which can impede their effectiveness as therapeutics agents. In this study, we present the facile synthesis of ursolic acid monodesmosides and uvaol bidesmosides, incorporating naturally occurring and water-soluble pentoses and deoxyhexose sugar moieties of opposite D- and L-configurations at the C3 or C3/C28 positions of the ursane core. The twenty synthetic saponins were evaluated in vitro for their cytotoxicity against lung carcinoma (A549) and colorectal adenocarcinoma (DLD-1) cell lines. Notably, all the bidesmosidic uvaol saponins were shown to be cytotoxic as compared to their non-cytotoxic parent triterpenoid. For each series of ursane-type saponins, the most active compounds were 3-O-α-L-arabinopyranosyl ursolic acid (3h) and 3,28-di-O-α-L-rhamnopyranosyl uvaol (4f), showing IC50 values in the low micromolar range against A549 and DLD-1 cancer lines.
| Type de document: | Article |
|---|---|
| Mots-clés libres: | Ursolic acid; Uvaol; Saponins; Monodesmosides; Bidesmosides; Cytotoxicity |
| Centre: | Centre INRS-Institut Armand Frappier |
| Date de dépôt: | 12 mai 2024 14:56 |
| Dernière modification: | 12 mai 2024 14:56 |
| URI: | https://espace.inrs.ca/id/eprint/15663 |
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