Human metabolism and elimination of the anthocyanin, cyanidin-3-glucoside: a 13C-tracer study
01 May 2013-The American Journal of Clinical Nutrition (American Society for Nutrition)-Vol. 97, Iss: 5, pp 995-1003
TL;DR: Anthocyanins are more bioavailable than previously perceived, and their metabolites are present in the circulation for ≤48 h after ingestion, as investigated in humans.
About: This article is published in The American Journal of Clinical Nutrition.The article was published on 2013-05-01 and is currently open access. It has received 492 citations till now. The article focuses on the topics: Metabolite.
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TL;DR: Scientific studies show that anthocyanidins and Anthocyanins possess antioxidative and antimicrobial activities, improve visual and neurological health, and protect against various non-communicable diseases.
Abstract: Anthocyanins are colored water-soluble pigments belonging to the phenolic group. The pigments are in glycosylated forms. Anthocyanins responsible for the colors, red, purple, and blue, are in fruits and vegetables. Berries, currants, grapes, and some tropical fruits have high anthocyanins content. Red to purplish blue-colored leafy vegetables, grains, roots, and tubers are the edible vegetables that contain a high level of anthocyanins. Among the anthocyanin pigments, cyanidin-3-glucoside is the major anthocyanin found in most of the plants. The colored anthocyanin pigments have been traditionally used as a natural food colorant. The color and stability of these pigments are influenced by pH, light, temperature, and structure. In acidic condition, anthocyanins appear as red but turn blue when the pH increases. Chromatography has been largely applied in extraction, separation, and quantification of anthocyanins. Besides the use of anthocyanidins and anthocyanins as natural dyes, these colored pigments are potential pharmaceutical ingredients that give various beneficial health effects. Scientific studies, such as cell culture studies, animal models, and human clinical trials, show that anthocyanidins and anthocyanins possess antioxidative and antimicrobial activities, improve visual and neurological health, and protect against various non-communicable diseases. These studies confer the health effects of anthocyanidins and anthocyanins, which are due to their potent antioxidant properties. Different mechanisms and pathways are involved in the protective effects, including free-radical scavenging pathway, cyclooxygenase pathway, mitogen-activated protein kinase pathway, and inflammatory cytokines signaling. Therefore, this review focuses on the role of anthocyanidins and anthocyanins as natural food colorants and their nutraceutical properties for health. Abbreviations: CVD: Cardiovascular disease VEGF: Vascular endothelial growth factor.
1,411 citations
TL;DR: The interactions between phenolic compounds and lipids, carbohydrates and proteins and their impact on polyphenol activity are reviewed.
763 citations
TL;DR: It is suggested that GP act in the intestine to modify gut microbial community structure, resulting in lower intestinal and systemic inflammation and improved metabolic outcomes, and the gut microbiota may provide the missing link in the mechanism of action of poorly absorbed dietary polyphenols.
Abstract: Dietary polyphenols protect against metabolic syndrome, despite limited absorption and digestion, raising questions about their mechanism of action. We hypothesized that one mechanism may involve the gut microbiota. To test this hypothesis, C57BL/6J mice were fed a high-fat diet (HFD) containing 1% Concord grape polyphenols (GP). Relative to vehicle controls, GP attenuated several effects of HFD feeding, including weight gain, adiposity, serum inflammatory markers (tumor necrosis factor [TNF]α, interleukin [IL]-6, and lipopolysaccharide), and glucose intolerance. GP lowered intestinal expression of inflammatory markers (TNFα, IL-6, inducible nitric oxide synthase) and a gene for glucose absorption (Glut2). GP increased intestinal expression of genes involved in barrier function (occludin) and limiting triglyceride storage (fasting-induced adipocyte factor). GP also increased intestinal gene expression of proglucagon, a precursor of proteins that promote insulin production and gut barrier integrity. 16S rRNA gene sequencing and quantitative PCR of cecal and fecal samples demonstrated that GP dramatically increased the growth of Akkermansia muciniphila and decreased the proportion of Firmicutes to Bacteroidetes, consistent with prior reports that similar changes in microbial community structure can protect from diet-induced obesity and metabolic disease. These data suggest that GP act in the intestine to modify gut microbial community structure, resulting in lower intestinal and systemic inflammation and improved metabolic outcomes. The gut microbiota may thus provide the missing link in the mechanism of action of poorly absorbed dietary polyphenols.
509 citations
TL;DR: Recent findings on the bioavailability and biological activity of (poly)phenols are summarized, focusing on the epidemiological and clinical evidence of beneficial effects of flavonoids and related compounds on urinary tract infections, cognitive function and age-related cognitive decline, cancer and cardiovascular disease.
Abstract: There is substantial interest in the role of plant secondary metabolites as protective dietary agents. In particular, the involvement of flavonoids and related compounds has become a major topic in human nutrition research. Evidence from epidemiological and human intervention studies is emerging regarding the protective effects of various (poly)phenol-rich foods against several chronic diseases, including neurodegeneration, cancer and cardiovascular diseases. In recent years, the use of HPLC-MS for the analysis of flavonoids and related compounds in foods and biological samples has significantly enhanced our understanding of (poly)phenol bioavailability. These advancements have also led to improvements in the available food composition and metabolomic databases, and consequently in the development of biomarkers of (poly)phenol intake to use in epidemiological studies. Efforts to create adequate standardised materials and well-matched controls to use in randomised controlled trials have also improved the quality of the available data. In vitro investigations using physiologically achievable concentrations of (poly)phenol metabolites and catabolites with appropriate model test systems have provided new and interesting insights on potential mechanisms of actions. This article will summarise recent findings on the bioavailability and biological activity of (poly)phenols, focusing on the epidemiological and clinical evidence of beneficial effects of flavonoids and related compounds on urinary tract infections, cognitive function and age-related cognitive decline, cancer and cardiovascular disease.
466 citations
Cites background or methods from "Human metabolism and elimination of..."
...…ingested 0.5 g (1,114 μmol) of 13c5-labelled cyanidin-3-O-glucoside and after 48 h, relative bioavailability was assessed to be as 12 % of the 13c dose with 5.4 % excreted in urine and 6.9 % in breath, while faeces accounted for a further 32 % of the administered 13c-label (czank et al. 2013)....
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...A portion of an ingested dose of anthocyanins reaches the large intestine and is further metabolised by gut microbiota (González-Barrio et al. 2011a; czank et al. 2013; de Ferrars et al. 2014)....
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...In addition, more than half the carbon of glycosides and the flavonoid A ring may be metabolised to short chain fatty acids and, therefore, be available for energy metabolism by the host and ultimately be exhaled as cO2 (czank et al. 2013)....
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...1 3 considering the 32 % faecal recovery of 13c-label from ingested [13c5]cyanidin-3-O-glucoside (czank et al. 2013), microbial anthocyanin catabolites might not be absorbed extensively into the bloodstream. consequently, the upper part of the GI tract could be a more important site of absorption…...
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...7 for structures) (González-Barrio et al. 2011a; czank et al. 2013; Rodriguez-Mateos et al. 2013; de Ferrars et al. 2014)....
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TL;DR: Increased knowledge of the factors affecting polyphenol bioavailability, including dietary factors, is paramount and polyphenols may act synergistically due to their influence on efflux transporters such as p-glycoprotein.
Abstract: While many epidemiological studies have associated the consumption of polyphenols within fruits and vegetables with a decreased risk of developing several chronic diseases, intervention studies have generally not confirmed these beneficial effects. The reasons for this discrepancy are not fully understood but include potential differences in dosing, interaction with the food matrix, and differences in polyphenol bioavailability. In addition to endogenous factors such as microbiota and digestive enzymes, the food matrix can also considerably affect bioaccessibility, uptake, and further metabolism of polyphenols. While dietary fiber (such as hemicellulose), divalent minerals, and viscous and protein-rich meals are likely to cause detrimental effects on polyphenol bioaccessibility, digestible carbohydrates, dietary lipids (especially for hydrophobic polyphenols, e.g., curcumin), and additional antioxidants may enhance polyphenol availability. Following epithelial uptake, polyphenols such as flavonoids may reduce phase II metabolism and excretion, enhancing polyphenol bioavailability. Furthermore, polyphenols may act synergistically due to their influence on efflux transporters such as p-glycoprotein. In order to understand polyphenol bioactivity, increased knowledge of the factors affecting polyphenol bioavailability, including dietary factors, is paramount.
396 citations
References
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TL;DR: Gallic acid and isoflavones are the most well-absorbed polyphenols, followed by catechins, flavanones, and quercetin glucosides, but with different kinetics, and the least well- absorption polyphenol are the proanthocyanidins, the galloylated tea catech ins, andThe anthocyanins.
3,534 citations
"Human metabolism and elimination of..." refers result in this paper
...Serum concentrations of C3G that we observed were similar to those previously reported (6, 7); however, degradation products of C3G (PCA and phloroglucinaldehyde) reached collective peak serum concentrations of 0....
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TL;DR: Estimates of body surface area were made based on measurement of 81 subjects, ranging from premature infants to adults, and closer agreement was obtained with the equations and nomograms of Body, Brody, Faber and Melcher, and Sendroy and Cecchini, although minor deviations were noted in some age ranges.
1,561 citations
"Human metabolism and elimination of..." refers methods in this paper
...Absolute tracer excretion in the breath was calculated by estimating the CO2 production rate (27) from the body surface area (28) by using an estimated correction of physical activity levels (of 1....
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TL;DR: The PKSolver provided pharmacokinetic researchers with a fast and easy-to-use tool for routine and basic PK and PD data analysis with a more user-friendly interface and its output could be generated in Microsoft Word in the form of an integrated report.
1,493 citations
"Human metabolism and elimination of..." refers methods in this paper
...Pharmacokinetic modeling of metabolite concentrations was performed with the program PKSolver (29) for Excel 2007 (Microsoft) by using noncompartmental analysis....
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TL;DR: It is time to rethink the design of in vitro and in vivo studies, so that these issues are carefully considered, and the length of human intervention studies should be increased, to more closely reflect the long-term dietary consumption of polyphenols.
1,409 citations
TL;DR: Phenol-Explorer is the first comprehensive web-based database on polyphenol content in foods and should help researchers to better understand the role of phytochemicals in the technical and nutritional quality of food, and food manufacturers to develop tailor-made healthy foods.
Abstract: A number of databases on the plant metabolome describe the chemistry and biosynthesis of plant chemicals. However, no such database is specifically focused on foods and more precisely on polyphenols, one of the major classes of phytochemicals. As antoxidants, polyphenols influence human health and may play a role in the prevention of a number of chronic diseases such as cardiovascular diseases, some cancers or type 2 diabetes. To determine polyphenol intake in populations and study their association with health, it is essential to have detailed information on their content in foods. However this information is not easily collected due to the variety of their chemical structures and the variability of their content in a given food. Phenol-Explorer is the first comprehensive web-based database on polyphenol content in foods. It contains more than 37 000 original data points collected from 638 scientific articles published in peer-reviewed journals. The quality of these data has been evaluated before they were aggregated to produce final representative mean content values for 502 polyphenols in 452 foods. The web interface allows making various queries on the aggregated data to identify foods containing a given polyphenol or polyphenols present in a given food. For each mean content value, it is possible to trace all original content values and their literature sources. Phenol-Explorer is a major step forward in the development of databases on food constituents and the food metabolome. It should help researchers to better understand the role of phytochemicals in the technical and nutritional quality of food, and food manufacturers to develop tailor-made healthy foods. Database URL: http://www.phenol-explorer.eu
1,097 citations