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Updated: Feb 19, 2026

Structural Biology and Analytical Chemistry Approaches for Characterizing C-Glycoside Metabolic Enzymes in Human Gut Microbiota
Published on: May 23, 2025
General chemical synthesis of cyanidin-3-O-glycosides: configuration determination and structure-activity
Zipeng Zheng1, Jun Hu2, Weijie Zhou1
1Department of Food Science and Engineering, Institute of Food Safety and Nutrition, Guangdong Engineering Technology Center of Food Safety Molecular Rapid Detection, Jinan University, Guangzhou 510632, China.
Abstract:
Anthocyanins are a class of water-soluble flavonoid pigments widely distributed in plants, characterized by their flavylium cation core. Glycosylation modifications exert significant effects on the biological activities of anthocyanins with identical aglycones. This study accomplished the first chemical syntheses of cyanidin-3-O-galactoside (C3Gal) and cyanidin-3-O-arabinoside (C3Ara), providing a general glycosylation strategy. The configurations of β-D-galactopyranoside and α-L-arabinopyranoside were determined by 2D NMR. Comparative analysis of cyanidin-3-O-glucoside (C3Glu), C3Gal, and C3Ara revealed that C3Glu was the most stable, whereas C3Ara and C3Gal exhibited superior antioxidant activity. C3Ara also showed the strongest inhibition against α-amylase (IC50 = 98.16 μM), consistent with molecular docking predictions. These results reveal the key structure-activity: hexoses (glucose, galactose) have higher stability and reduced activity. Pentosyl arabinosides have higher biological activity. This work provides a reliable preparation method and research direction for anthocyanin glycosides.
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