Glycosylation Reactions in the Synthesis of Flavonoid Glycosides

Sun, Jiansong; Laval, S.; Yu, Biao

doi:10.1055/s-0033-1341052

Cited by 19 publications

(2 citation statements)

References 42 publications

(48 reference statements)

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“…With the tactic-I approach, a sugar moiety is directly attached to the desired flavonoid and tactic-II involves the development of flavonoid moiety after the establishment of glycosidic bonds. Many protocols have been developed since then, such as Koenigs-Knoor, PTC-Protocol or the recent Kondo et al methods; however, they all have drawbacks, such as low yield, the requirement for hazardous and expensive reagents and constant coupling, decoupling and protective steps, making the synthesis elaborate and expensive [65,66]. Even with all these shortcomings, synthetic approaches have yet to come up with approaches to form complex glycosides and glycoside with unusual bonds.…”

Section: Chemical Synthesis Of Flavonoids and Flavonoid Derivativementioning

confidence: 99%

Synthetic Biology towards Improved Flavonoid Pharmacokinetics

et al. 2021

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Flavonoids are a structurally diverse class of natural products that have been found to have a range of beneficial activities in humans. However, the clinical utilisation of these molecules has been limited due to their low solubility, chemical stability, bioavailability and extensive intestinal metabolism in vivo. Recently, the view has been formed that site-specific modification of flavonoids by methylation and/or glycosylation, processes that occur in plants endogenously, can be used to improve and adapt their biophysical and pharmacokinetic properties. The traditional source of flavonoids and their modified forms is from plants and is limited due to the low amounts present in biomass, intrinsic to the nature of secondary metabolite biosynthesis. Access to greater amounts of flavonoids, and understanding of the impact of modifications, requires a rethink in terms of production, more specifically towards the adoption of plant biosynthetic pathways into ex planta synthesis approaches. Advances in synthetic biology and metabolic engineering, aided by protein engineering and machine learning methods, offer attractive and exciting avenues for ex planta flavonoid synthesis. This review seeks to explore the applications of synthetic biology towards the ex planta biosynthesis of flavonoids, and how the natural plant methylation and glycosylation pathways can be harnessed to produce modified flavonoids with more favourable biophysical and pharmacokinetic properties for clinical use. It is envisaged that the development of viable alternative production systems for the synthesis of flavonoids and their methylated and glycosylated forms will help facilitate their greater clinical application.

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Section: Chemical Synthesis Of Flavonoids and Flavonoid Derivativementioning

confidence: 99%

Synthetic Biology towards Improved Flavonoid Pharmacokinetics

et al. 2021

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“…A detailed description of the mechanisms of glycosylation reactions can be found elsewhere (Jensen, 2002;Das and Mukhopadhyay, 2016). Specific examples of glycosylation reactions of flavonoids are given in the following studies (Sun et al, 2014;Huanji et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Progress and Achievements in Glycosylation of Flavonoids

et al. 2021

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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.

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Flavonoid Glycosides

2024

Carbohydrate Chemistry in the Total Synthesis of Naturally Occurring Glycosides

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Glycosylation Reactions in the Synthesis of Flavonoid Glycosides

Abstract: An overview of flavonoid glycoside synthesis has been provided with an emphasis on the construction of the glycosidic linkages.

Cited by 19 publications

References 42 publications

Synthetic Biology towards Improved Flavonoid Pharmacokinetics

Synthetic Biology towards Improved Flavonoid Pharmacokinetics

Progress and Achievements in Glycosylation of Flavonoids

Flavonoid Glycosides

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