Recent Advances on Natural Aryl-C-glycoside Scaffolds: Structure, Bioactivities, and Synthesis—A Comprehensive Review

Abstract

Aryl-C-glycosides, of both synthetic and natural origin, are of great significance in medicinal chemistry owing to their unique structures and stability towards enzymatic and chemical hydrolysis as compared to O-glycosides. They are well-known antibiotics and potent enzyme inhibitors and possess a wide range of biological activities such as anticancer, antioxidant, antiviral, hypoglycemic effects, and so on. Currently, a number of aryl-C-glycoside drugs are on sale for the treatment of diabetes and related complications. This review summarizes the findings on aryl-C-glycoside scaffolds over the past 20 years, concerning new structures (over 200 molecules), their bioactivities—including anticancer, anti-inflammatory, antioxidant, antivirus, glycation inhibitory activities and other pharmacological effects—as well as their synthesis.

Recent Advances on the Synthesis of C-Glycosides from 1,2-Glycals

“…al in 2018, 30 and Liu in 2022 has also comprehensively reviewed the area of synthesis and biological activities of C-aryl glycosides. 31 Recently, Liang et al discussed C-H activation for the synthesis of C-glycoside. 32 Recently, Hussain et al discussed the advancement for the synthesis of natural products particularly from glycal.…”

“…29 Suzuki et al (2018) 30 and Liu (2022) have also comprehensively reviewed the synthesis and biological activities of C-aryl glycosides. 31 Recently, Liang et al reported C-H activation for the synthesis of C-glycosides, 32 whilst Hussain and co-workers discussed advancements for the synthesis of natural products from glycals. 33 Expanding the horizon of synthetic routes to Cglycosides, in the last few years, glycosyl radicals have emerged as very important precursors for constructing the C-glycosidic linkage.…”

Reaction intensification for biocatalytic production of polyphenolic natural product di‐C‐β‐glucosides

“…This involves two sugars individually linked to the same benzene ring of the polyphenol via a C ‐glycosidic bond (Kitamura et al, 2018; Y. Q. Zhang et al, 2022). The type of glycosylation most often used is that of C ‐β‐ d ‐glucosyl (Figure 1) (C. F. Liu, 2022; Y. Q. Zhang et al, 2022).…”

“…Zhang et al, 2022). The type of glycosylation most often used is that of C-β-D-glucosyl (Figure 1) (C. F. Liu, 2022;Y. Q. Zhang et al, 2022).…”

Studies on the synthesis of sugar chalcone derivatives for protein binding

“…Physicochemical and spectral data of (E)-1-(4,6-O-butylideneβ-D-glucopyranosyl)-4-(4-hydroxyphenyl)-but-3-en-2-one (4)Colourless solid, M.pt. 188-190 °C,Yield 87 %,1 H NMR(300 MHz, CDCl 3 + DMSO-d 6 ): δ 9.50 (s, 1H, Ph-OH), 7.53-7.40 (m, 3H, ArÀ H), 6.86 (d, J = 8.4 Hz, 2H, ArÀ H), 6.60 (d, J = 15.9 Hz, 1H, Alk-H), 4.76 (s,…”