The Impact of O-Glycosylation on Cyanidin Interaction with RBCs and HMEC-1 Cells—Structure–Activity Relationships

Abstract

With the aim of contributing to the knowledge about their potential therapeutic activity, we determined the biological activities of cyanidin and its selected O-glycosides in relation to erythrocytes (RBCs) and human dermal vascular endothelial cells (HMEC-1). Furthermore, on the basis of changes in the physical/functional properties of the cells, the structure–activity relationships of the compounds were determined. Concerning erythrocytes, we analyzed the antioxidant activity of the compounds and their impact on the RBCs’ shape and transmembrane potential. The compounds’ cytotoxic activity, ability to modulate apoptosis, cell cycle, and intracellular ROS generation, as well as inhibitory activity against AAPH-inducted oxidative stress, were determined in relation to HMEC-1 cells. We demonstrated that biological activity of cyanidin and its O-glycosides strongly depends on the number and type of sugar substituents, and varies depending on the extracellular environment and type of cells. The compounds are practically non-cytotoxic, and do not induce apoptosis or disturb the progression of the cell cycle. Additionally, the compounds alter the shape of RBCs, but they do not affect their transmembrane potential. They effectively protect erythrocytes against free radicals and affect intracellular reactive oxygen spices (ROS) generation under physiological and AAPH-induced oxidative stress conditions. Our results suggest a potential beneficial effect of cyanidin on the cardiovascular system.

Anthocyanins: Traditional Uses, Structural and Functional Variations, Approaches to Increase Yields and Products’ Quality, Hepatoprotection, Liver Longevity, and Commercial Products

“…It seemed that the addition of more sugar units inversely affected the antioxidant activity of the cyanidin [322]. Similar conclusions were drawn for the glycosylation effects on the antioxidant potentials of the cyanidin-based structures as observed on the RBCs in presence of AAPH-induced oxidative stress conditions [323]. The level of ROS was significantly decreased as observed for the aglycone, cyanidin, as well as the glycosides, cyanidin-3-O-arabinoside, cyanidin-3-O-galactoside, and cyanidin-3-5-O-di-glucoside.…”

“…The level of ROS was significantly decreased as observed for the aglycone, cyanidin, as well as the glycosides, cyanidin-3-O-arabinoside, cyanidin-3-O-galactoside, and cyanidin-3-5-O-di-glucoside. However, the cyanidin-3-O-rutinoside and cyanidin-3-O-β-glucoside have showed no significant effects [323]. The importance of 3-OH group of the anthocyanidins, and corresponding anthocyanins for the antioxidant activity of these compounds has been demonstrated by Ali et al, using eight different anthocyanidins, and seven anthocyanins, as well as two synthetic products based on 4 -hydroxy flavylium compounds, which were examined for their scavenging activity by the DPPH and ABTS (2,2 -azino-bis(3-ethylbenzothiazoline-6sulphonic acid)) radicals, as well as their reducing power for the ferric ions using FRAP assay [153].…”

Antioxidant Effects of Elderberry Anthocyanins in Human Colon Carcinoma Cells: A Study on Structure–Activity Relationships

“…Further studies in this regard are highly recommended. Disregarding size and type of the sugar moiety for effective uptake, the impact on membrane fluidity and/or interaction, in particular of anthocyanins with complex glycosyl moieties, might play a role as well, as has been shown by studies of Cyboran‐Mikolajczyk et al., [ 50 ] thus leading to alteration of cell response.…”

Comparison of Osmotic Resistance, Shape and Transmembrane Potential of Erythrocytes Collected from Healthy and Fed with High Fat-Carbohydrates Diet (HF-CD) Pigs—Protective Effect of Cistus incanus L. Extracts

“…It is possible, because extracts components such us glycosylated derivatives of myricetin, quercetin and kaempferol are rather hydrophilic. It is already known that hydrophilic flavonoids and oligomers interact with the area of head groups of lipids at the lipid–water interface, and this interaction may be associated with the formation of hydrogen bonds or have an electrostatic nature [ 37 , 38 , 39 ]. Their presence in this area may partially disrupts the interactions between lipid and/or protein and lipid molecules and consequently cause the observed changes in the physical properties of RBCs.…”

“…EC2 extract was prepared according to the method described earlier in [ 23 ]. In this method ethyl acetate extraction was used, which causes selective precipitation of catechin and procyanidin groups [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ]. Polyphenols contained in the extracts were added to the Table 2 .…”