title: Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects.
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 &amp; 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 againstHelicobacter pyloriinfection, 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.
authors.affiliation: 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. Javier_Olivas22_09@hotmail.com.
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Olivas-Aguirre
authors.affiliation: 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. Jogarcia@uacj.mx.
authors.forename: Joaquín
authors.initials: J
authors.lastname: Rodrigo-García
authors.affiliation: 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. nmartine@uacj.mx.
authors.forename: Nina Del R
authors.initials: ND
authors.lastname: Martínez-Ruiz
authors.affiliation: Departamento de Investigación y Posgrado en Alimentos, Facultad de Química, Universidad Autónoma de Querétaro, Cerro de las Campanas s/n, Querétaro 76010, Querétaro, Mexico. smendoza@uaq.mx.
authors.forename: Arely I
authors.initials: AI
authors.lastname: Cárdenas-Robles
authors.affiliation: Departamento de Investigación y Posgrado en Alimentos, Facultad de Química, Universidad Autónoma de Querétaro, Cerro de las Campanas s/n, Querétaro 76010, Querétaro, Mexico. cardenas.arely.i@gmail.com.
authors.forename: Sandra O
authors.initials: SO
authors.lastname: Mendoza-Díaz
authors.affiliation: 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. ealvarez@uacj.mx.
authors.forename: Emilio
authors.initials: E
authors.lastname: Álvarez-Parrilla
authors.affiliation: 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. gustavo@ciad.mx.
authors.forename: Gustavo A
authors.initials: GA
authors.lastname: González-Aguilar
authors.affiliation: 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. ldelaros@uacj.mx.
authors.forename: Laura A
authors.initials: LA
authors.lastname: de la Rosa
authors.affiliation: 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. aramos@uacj.mx.
authors.forename: Arnulfo
authors.initials: A
authors.lastname: Ramos-Jiménez
authors.affiliation: 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. awall@uacj.mx.
authors.forename: Abraham
authors.initials: A
authors.lastname: Wall-Medrano
keywords: anthocyanin; antioxidant; berries; bioaccessibility; cyanidin; cyanidin 3-O-glucoside; foodomics; phenolic compounds; splanchnic metabolism