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Synthesis, cytotoxicity and anti-inflammatory activity of rhamnose-containing ursolic and betulinic acid saponins

Sylla Balla, Lavoie Serge, Legault Jean, Gauthier Charles et Pichette André. (2019). Synthesis, cytotoxicity and anti-inflammatory activity of rhamnose-containing ursolic and betulinic acid saponins. RSC Advances, 9, (68), p. 39743-39757.

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URL officielle: http://dx.doi.org/doi:10.1039/C9RA09389C

Résumé

Betulinic acid and ursolic acid are ubiquitous, naturally-occurring triterpenoids exhibiting various pharmacological activities including cytotoxic and anti-inflammatory activities. However, these triterpenoids display unfavorable pharmacokinetic properties as well as low aqueous solubility. It has been shown that the presence of α-L-rhamnose moieties positively modulates the anticancer activity of secondary metabolites. Herein we report the synthesis and in vitro evaluation of cytotoxic and anti-inflammatory activities of a series of rhamnose-containing ursolic and betulinic acid saponins. Relying on Schmidt's normal and inverse procedures, monorhamnosides, (1→4)-linked dirhamnosides as well as branched trirhamnosides and tetrarhamnosides were synthesized in high yields with full control of stereoselectivity. A betulinic acid saponin bearing a 3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl residue was found to be a potent cytotoxic agent against human colorectal adenocarcinoma cells without damaging the healthy cells (selectivity ratio > 20) whereas rhamnose-containing ursolic acid saponins potently inhibited NO overproduction induced by LPS-stimulated macrophages. Our results reveal that rhamnose-containing ursolic and betulinic acid saponins represent promising therapeutic agents.

Type de document:Article publié dans une revue avec comité d'évaluation
ISSN:2046-2069
Volume:9
Numéro:68
Pages:p. 39743-39757
Version évaluée par les pairs:Oui
Date:2019
Identifiant unique:10.1039/C9RA09389C
Sujets:Sciences naturelles et génie > Sciences naturelles > Biologie et autres sciences connexes
Sciences naturelles et génie > Sciences naturelles > Chimie
Sciences de la santé > Sciences médicales > Pharmacologie
Département, module, service et unité de recherche:Départements et modules > Département des sciences fondamentales
Mots-clés:Betulinic acid, ursolic acid, synthesis, cytotoxicity, anti-inflammatory activity, rhamnose, therapeutic agents
Déposé le:10 nov. 2021 22:05
Dernière modification:10 nov. 2021 22:05
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Creative Commons LicenseSauf indication contraire, les documents archivés dans Constellation sont rendus disponibles selon les termes de la licence Creative Commons "Paternité, pas d'utilisation commerciale, pas de modification" 2.5 Canada.

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