Abstract
Saponins are a structurally diverse class of natural glycosides that possess a broad spectrum of biological activities. They are composed of hydrophilic carbohydrate moiety and hydrophobic triterpenoid or steroid aglycon. Naturally occurring diosgenyl glycosides are the most abundant steroid saponins, and many of them exhibit various pharmacological properties. Herein, we present an overview of semisynthetic saponins syntheses–diosgenyl β-d-glycosaminosides (d-gluco and d-galacto). These glycosides possess a 2-amino group, which creates great possibilities for further modifications. A wide group of glycosyl donors, different N-protecting groups and various reaction conditions used for their synthesis are presented. In addition, this paper demonstrates the possibilities of chemical modifications of diosgenyl β-d-glycosaminosides, associated with functionalisation of the amino group. These provide N-acyl, N-alkyl, N,N-dialkyl, N-cinnamoyl, 2-ureido and 2-thiosemicarbazonyl derivatives of diosgenyl β-d-glycosaminosides, for which the results of biological activity tests (antifungal, antibacterial, anti-cancer and hemolytic) are presented.
Highlights
The aim of this review is to provide information on the methods of synthesis and biological activity of diosgenyl β-d-glycosaminosides and their derivatives
This review presents various synthetic approaches for obtaining diosgenyl β-d-glycosaminosides
A properly protected amino group located at the C-2 atom of the glycosyl donor can play a key role in a glycosidic coupling, e.g., amide-type groups participate in the process of bond forming as the neighbouring group, which favours the formation of a 1,2-trans-glycosidic bond [38]
Summary
The aim of this review is to provide information on the methods of synthesis and biological activity of diosgenyl β-d-glycosaminosides and their derivatives. These are semisynthetic saponins with proven antimicrobial and antitumor activity. This makes them very promising candidates for use as an antifungal or antibacterial drug. A significant advantage of these compounds is that they are not toxic. The toxicity of saponins is a particular limitation in the clinical application of this group of compounds.
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