Low-Molecular Arylglycosides: From Nature to Synthesis

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Low-Molecular Arylglycosides: From Nature to Synthesis

Elena Stepanova 1

1 Tomsk Polytechnic university, Tomsk, Russian Federation

Low-molecular arylglycosides are common plant metabolites. The first reported arylglycoside salicin – glucoside of salicylic alcohol – was isolated from white willow (Salix alba) bark in 1828. Salicin and have become the prototype for such widely used and studied drug as “Aspirin” [1]. Further, Salicin was found in many species of various medicinal plants and now considered as one of the most abandoned secondary metabolites of plants. A number of salicin derivatives were isolated along with the parent compound, mainly esterified with different benzoic or cinnamic acids. Many glycosides bearing different phenolic aglycns were found in nature [2]. Though, low-molecular arylglycosides are now known for many decades, only few syntheses of such compounds were described [3]. In the preset research, we seek for the way of synthesis of salicin-like low-molecular arylglycosides aiming to find an easy way for producing these compounds. The study of low-molecular arylglycosides is funded by RFBR according to the research project № 18-33-00365.

Figure 1 – Salicin and its derivatives in plants as synthetic challenges

Shara M, Stohs SJ. Efficacy and safety of white willow bark (Salix alba) extracts. Phytother Res. 2015, 29(8):1112-6.

Boeckler GA, Gershenzon J, Unsicker SB. Phenolic glycosides of the Salicaceae and their role as anti-herbivore defenses. Phytochem. 2011, 72(13):1497-509

Belyanin ML, Stepanova EV, Ogorodnikov VD. First total chemical synthesis of natural acyl derivatives of some phenolglycosides of the family Salicaceae. Carbohydr Res. 2012, 363:66-72.

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