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Molecules 2016, 21(9), 1264; doi:10.3390/molecules21091264

Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects

1
Instituto de Ciencias Biomédicas, Departamento de Ciencias Químico-Biológicas, Universidad Autónoma de Ciudad Juárez, Anillo Envolvente del PRONAF y Estocolmo s/n, Ciudad Juárez 32310, Chihuahua, Mexico
2
Departamento de Investigación y Posgrado en Alimentos, Facultad de Química, Universidad Autónoma de Querétaro, Cerro de las Campanas s/n, Querétaro 76010, Querétaro, Mexico
3
Coordinación de Tecnología de Alimentos de Origen Vegetal, Centro de Investigación en Alimentación y Desarrollo, AC. Carretera a la Victoria km. 0.6, AP 1735, Hermosillo 83000, Sonora, Mexico
*
Author to whom correspondence should be addressed.
Academic Editors: Celestino Santos-Buelga and Arturo San Feliciano
Received: 15 August 2016 / Revised: 9 September 2016 / Accepted: 13 September 2016 / Published: 21 September 2016
(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues)
View Full-Text   |   Download PDF [2279 KB, uploaded 21 September 2016]   |  

Abstract

Anthocyanins (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
Keywords: anthocyanin; cyanidin 3-O-glucoside; cyanidin; antioxidant; bioaccessibility; berries; phenolic compounds; foodomics; splanchnic metabolism anthocyanin; cyanidin 3-O-glucoside; cyanidin; antioxidant; bioaccessibility; berries; phenolic compounds; foodomics; splanchnic metabolism
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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.

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