Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects
AbstractAnthocyanins (ACNs) are plant secondary metabolites from the flavonoid family. Red to blue fruits are major dietary sources of ACNs (up to 1 g/100 g FW), being cyanidin-3-O-glucoside (Cy3G) one of the most widely distributed. Cy3G confers a red hue to fruits, but its content in raspberries and strawberries is low. It has a good radical scavenging capacity (RSC) against superoxide but not hydroxyl radicals, and its oxidative potential is pH-dependent (58 mV/pH unit). After intake, Cy3G can be metabolized (phases I, II) by oral epithelial cells, absorbed by the gastric epithelium (1%–10%) and it is gut-transformed (phase II & microbial metabolism), reaching the bloodstream (<1%) and urine (about 0.02%) in low amounts. In humans and Caco-2 cells, Cy3G’s major metabolites are protocatechuic acid and phloroglucinaldehyde which are also subjected to entero-hepatic recycling, although caffeic acid and peonidin-3-glucoside seem to be strictly produced in the large bowel and renal tissues. Solid evidence supports Cy3G’s bioactivity as DNA-RSC, gastro protective, anti-inflammatory, anti-thrombotic chemo-preventive and as an epigenetic factor, exerting protection against Helicobacter pylori infection, age-related diseases, type 2 diabetes, cardiovascular disease, metabolic syndrome and oral cancer. Most relevant mechanisms include RSC, epigenetic action, competitive protein-binding and enzyme inhibition. These and other novel aspects on Cy3G’s physical-chemistry, foodomics, and health effects are discussed. View Full-Text
Share & Cite This Article
Olivas-Aguirre, F.J.; Rodrigo-García, J.; Martínez-Ruiz, N.R.; Cárdenas-Robles, A.I.; Mendoza-Díaz, S.O.; Álvarez-Parrilla, E.; González-Aguilar, G.A.; de la Rosa, L.A.; Ramos-Jiménez, A.; Wall-Medrano, A. Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects. Molecules 2016, 21, 1264.
Olivas-Aguirre FJ, Rodrigo-García J, Martínez-Ruiz NR, Cárdenas-Robles AI, Mendoza-Díaz SO, Álvarez-Parrilla E, González-Aguilar GA, de la Rosa LA, Ramos-Jiménez A, Wall-Medrano A. Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects. Molecules. 2016; 21(9):1264.Chicago/Turabian Style
Olivas-Aguirre, Francisco J.; Rodrigo-García, Joaquín; Martínez-Ruiz, Nina R.; Cárdenas-Robles, Arely I.; Mendoza-Díaz, Sandra O.; Álvarez-Parrilla, Emilio; González-Aguilar, Gustavo A.; de la Rosa, Laura A.; Ramos-Jiménez, Arnulfo; Wall-Medrano, Abraham. 2016. "Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects." Molecules 21, no. 9: 1264.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.