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Review
. 2021 Mar 31:9:637994.
doi: 10.3389/fchem.2021.637994. eCollection 2021.

Progress and Achievements in Glycosylation of Flavonoids

Ruslana S Khodzhaieva  1 , Eugene S Gladkov  1 , Alexander Kyrychenko  1 , Alexander D Roshal  1
Affiliations
Review

Progress and Achievements in Glycosylation of Flavonoids

Ruslana S Khodzhaieva et al. Front Chem. .

Abstract

In recent years, the chemistry of flavonoid glycosylation has undergone significant developments. This mini-review is devoted to summarizing existing strategies and methods for glycosylation of natural and synthetic flavonoids. Herein we overviewed the reaction conditions of flavonoid glycosylation depending on the position of hydroxyl groups in a parent molecule, the degree of it conjugation with the π-system, the presence of steric factors, the formation of intramolecular hydrogen bonds, etc. Especial attention was given to the choice of the glycosyl donor moiety, which has a significant effect on the yield of the final glycosidated products. Finally, a general strategy for regioselective glycosylation of flavonoids containing several hydroxyl groups is outlined.

Keywords: chromone; flavonoid; glycosidic group; glycosylation; regioselectivity.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

GRAPHICAL ABSTRACT
GRAPHICAL ABSTRACT
FIGURE 1
FIGURE 1
Three strategies of flavonoid glycosylation. (A)—glycosylation of starting reagents: anthocyanidine synthesis (regioselectivity of flavonoid synthesis is determined by glycosylation of one of the starting products). (B)—glycosylation of intermediate products: isoflavone synthesis (the regioselectivity of synthesis is determined by the direction of glycosylation of the intermediate). (C)—glycosylation of synthesis products: obtaining flavonol glucosides (the direction of glycosylation is regulated by the preliminary protection of certain hydroxyl groups of flavonol). formula image- β-D-glycosyl fragment with protected hydroxyl groups.
FIGURE 2
FIGURE 2
Main pathways of flavonoid synthesis.
See this image and copyright information in PMC

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