Synthesis, Modification and Biological Activity of Diosgenyl β-d-Glycosaminosides: An Overview

• Published in: Molecules (Basel, Switzerland) Switzerland), 2020-11, Vol.25 (22), p.5433
• Main Authors: Grzywacz, Daria, Liberek, Beata, Myszka, Henryk
• Format: Article
• Language: English
• Subjects: amine group modifications; Amines - chemistry; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; antimicrobial activity; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Biological activity; Biological effects; Cancer; Carbohydrates; Carbon; Chemical Phenomena; Chemistry Techniques, Synthetic; Chromatography; diosgenin glycosides; diosgenyl β- d -galactosaminoside; diosgenyl β- d -glucosaminoside; Folk medicine; Fungicides; Glucose; Glycosides; Hemolysis; Humans; Hydrophobicity; Molecular Structure; Protecting groups; Review; Saponins; Saponins - chemical synthesis; Saponins - chemistry; Saponins - pharmacology; Solvent extraction processes; steroid saponin; Steroids; Structure-Activity Relationship
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules25225433

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 -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 -acyl, -alkyl, -dialkyl, -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.