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 & 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.

Antioxidant Capacity of Anthocyanin Pigments

“…Anthocyanins [13,14,17,293,[343][344][345][346] are members of the flavonoid group of phytochemicals, a group predominant in fruits and vegetables, especially in berries. Recent research raised awareness of the importance [347,348] of anthocyanins in the diet.…”

Simple and Fast Method for Identification and Quantification of Anthocyanidins in Berries by Ultra Performance Liquid Chromatography-Mass Spectrometry

“…This result demonstrates that the separation of anthocyanidins can be achieved in a much smaller period of time (1.30 min) when compared to the conventional high pressure liquid chromatography (HPLC) runs, which are the most used for this purpose, with analytical runs of approximately 20 to 60 min. 11,[13][14][15] The spectra of fragmentation and product ion spectra obtained by direct infusion of analytical standards of anthocyanidins delphinidin, cyanidin and pelargonidin are shown in Supplementary Information. The mass/charge ratio (m/z) values of these compounds, as well as the fragments resulting from electrospray ionization, were subsequently used in the quantification of these compounds in the samples.…”

“…14 The information regarding the concentrations, the structure and the possible fragments coming from these flavonoids is important for the fields of analytical chemistry, food industry and food science, because anthocyanidins are natural pigments capable of being inserted into formulations in novel foods, and have different biological functions (antiinflammatory, anti-microbial, neuroprotective). 15 Cyanidin is a potential protective agent against neurodegenerative diseases 20 by protecting the neuronal cells against oxidative processes, and this anthocyanin RSD: relative standard deviation; LOD: limit of detection; LOQ: limit of quantification. occurs with the highest frequency in edible fruits.…”

“…occurs with the highest frequency in edible fruits. 15 Anthocyanidins are able to cross the blood-brain barrier, being promising in the prevention and treatment of brain cancer arising from alterations induced by epithelialmesenchymal transition. 7 The antioxidant power of different anthocyanidins depends on the structure of each compound.…”

Cyanidin Curtails Renal Cell Carcinoma Tumorigenesis

“…Cyanidin is not the most common dietary anthocyanidin, however, and it occurs naturally in its glycosylated form, namely, cyanidin-3-glucoside (C3G). After intake, C3G can be metabolized by oral epithelial cells and absorbed by the gastric epithelium (1-10%), where it is gut-transformed and enters the bloodstream (< 1%) and urine (about 0.02%) [18]. After oral administration, the predominant flavonoid species in the gastrointestinal (GI) mucosa and liver is C3G, whilst after IV dosing the majority of anthocyanins are C3G metabolites, which are mostly products of methylation and glucuronidation.…”