Scope: Glycosylation is a way to increase structure-stability of anthocyanins, yet compromises their bioactivity. The study investigates the antioxidant activity of purified cyanidin (Cy)-based anthocyanins and respective degradation products in Caco-2 clone C2BBe1 aiming to identify structure-activity relationships. Results and Methods: Cyanidin 3-O-glucoside (Cy-3-glc) and cyanidin 3-O-sambubioside (Cy-3-sam) proved to be most potent regarding antioxidant properties and protection against hydrogen peroxide (H 2 O 2 )-induced reactive oxygen species (ROS)-levels measured with the dichloro-fluorescein (DCF) assay. Cyanidin 3-O-sambubioside-5-O-glucoside (Cy-3-sam-5-glc) and cyanidin 3-O-rutinoside (Cy-3-rut) were less efficient and not protective, reflecting potential differences in uptake and/or degradation. Following ranking in antioxidant efficiency is suggested: (concentrations ≤10 × 10 −6 M) Cy-3-glc ≥ Cy-3-sam > Cy-3-sam-5-glc ≈ Cy-3-rut ≈ Cy; (concentrations ≥50 × 10 −6 M) Cy-3-glc ≈ Cy-3-sam ≥ Cy > Cy-3-sam-5-glc ≈ Cy-3-rut. Cy and protocatechuic acid (PCA) reduced ROS-levels as potent as the mono-and di-glycoside, whereas phloroglucinol aldehyde (PGA) displayed pro-oxidant properties. None of the degradation products protected from oxidative stress.Gene transcription analysis of catalase (CAT), superoxide-dismutase (SOD), glutathione-peroxidase (GPx), heme-oxygenase-1 (HO-1), and glutamate-cysteine-ligase ( GCL) suggest no activation of nuclear factor erythroid 2-related factor 2 (Nrf2). Conclusion: More complex residues and numbers of sugar moieties appear to be counterproductive for antioxidant activity. Other mechanisms than Nrf2-activation should be considered for protective effects.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.