2. Academic Validation
  3. Synthesis and cytotoxicity evaluation of d- and l-sugar-containing mono- and bidesmosidic ursane-type saponins

Synthesis and cytotoxicity evaluation of d- and l-sugar-containing mono- and bidesmosidic ursane-type saponins

  • Bioorg Med Chem. 2024 May 15:106:117737. doi: 10.1016/j.bmc.2024.117737.
Balla Sylla 1,  Gilles Jost 1,  Serge Lavoie 1,  Jean Legault 2,  Charles Gauthier 3,  André Pichette 4
Affiliations

Affiliations

  • 1 Centre de Recherche sur La Boréalie (CREB), Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boulevard de l'Université, Chicoutimi, Québec G7H 2B1, Canada.
  • 2 Centre de Recherche sur La Boréalie (CREB), Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boulevard de l'Université, Chicoutimi, Québec G7H 2B1, Canada; Unité Mixte de Recherche (UMR) INRS-UQAC, Centre Armand-Frappier Santé Biotechnologie, Institut National de la Recherche Scientifique (INRS), Chicoutimi & Laval, Québec G7H 2B1, Canada.
  • 3 Centre de Recherche sur La Boréalie (CREB), Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boulevard de l'Université, Chicoutimi, Québec G7H 2B1, Canada; Unité Mixte de Recherche (UMR) INRS-UQAC, Centre Armand-Frappier Santé Biotechnologie, Institut National de la Recherche Scientifique (INRS), Chicoutimi & Laval, Québec G7H 2B1, Canada. Electronic address: charles.gauthier@inrs.ca.
  • 4 Centre de Recherche sur La Boréalie (CREB), Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boulevard de l'Université, Chicoutimi, Québec G7H 2B1, Canada. Electronic address: andre.pichette@uqac.ca.
PMID: 38718553 DOI: 10.1016/j.bmc.2024.117737
Abstract

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.

Keywords

Bidesmosides; Cytotoxicity; Monodesmosides; Saponins; Ursolic acid; Uvaol.

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