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Journal of Agricultural and Food... Jan 2021Anthocyanins have been known for their health benefits. However, the digestion and absorption of anthocyanins through the gastrointestinal tract have not been fully...
Anthocyanins have been known for their health benefits. However, the digestion and absorption of anthocyanins through the gastrointestinal tract have not been fully clarified, creating challenges for understanding why anthocyanins have high biological activities and purported low bioavailability . Twenty-seven male rats were intubated with a 500 mg/kg dose of cyanidin-3-glucoside (C3G). Samples from rats' stomach, duodenum, jejunum, ileum, colon, and serum were collected at 0.5, 1, 2, 3, 4, 5, 6, 12, and 24 h after intubation. Three rats without C3G were used as the control with samples collected at 0 h. C3G and its metabolites in each sample were analyzed using high-performance liquid chromatography-PDA-electrospray ionization-MS/MS. These studies' results unequivocally demonstrated that cyanidin and phenolic acids were the primary C3G metabolites absorbed, mainly in the jejunum and ileum, between 1 and 5 h post-ingestion. We speculate that C3G uses phloroglucinaldehyde and protocatechuic acid metabolic pathways in its metabolism .
Topics: Animals; Anthocyanins; Biological Availability; Chromatography, High Pressure Liquid; Colon; Hydroxybenzoates; Ileum; Jejunum; Male; Rats; Rats, Sprague-Dawley; Tandem Mass Spectrometry
PubMed: 33428422
DOI: 10.1021/acs.jafc.0c07771 -
The Journal of Nutrition Feb 2024Berries are foods that are abundant in nutrients, especially flavonoids, that promote good health; however, the effects of total berries on mortality are not well...
BACKGROUND
Berries are foods that are abundant in nutrients, especially flavonoids, that promote good health; however, the effects of total berries on mortality are not well characterized.
OBJECTIVES
We evaluated whether intakes of total berries and specific berry types including blueberries, strawberries, cranberries, flavonoids, and subclasses of flavonoids (anthocyanidins, flavonols, flavones, flavanones, flavan-3-ols, and isoflavones) in relation to mortality risk in United States adults.
METHODS
A nationally representative sample of the United States adult population was obtained using data from the 1994-2014 NHANES (n = 37,232). Intake of berries was estimated using 24-h food recalls (1999-2014), and flavonoids intake was calculated using the matched USDA's expanded flavonoid database. Mortality outcomes based on 8 y of follow-up were obtained using linked death certificates.
RESULTS
Compared with nonconsumers, the multivariable-adjusted hazard ratio for all-cause mortality was 0.79 [95% confidence intervals (CI): 0.7, 0.89] for any berry consumption, 0.86 (0.75, 0.99) for strawberry consumption 0.79 (0.66, 0.95) for blueberries, and 0.69 (0.51, 0.93) for cranberries. Compared with the lower median of intake, risk of all-cause mortality for greater intake was 0.85 (0.74, 0.97) for total flavonoids, 0.85 (0.76, 0.95) for anthocyanidins, 0.9 (0.82, 0.99) for flavan-3-ols, 0.89 (0.79, 0.9) for flavanols, and 0.89 (0.8, 0.99) for flavones. There was a dose-response relationship between intakes of total flavonoids, anthocyanidins, and flavones and lower all-cause mortality risks (P < 0.05). Risk for cardiometabolic mortality was 0.75 (0.58, 0.98) for berry consumers and 0.49 (0.25, 0.98) for cranberry consumers. For respiratory disease mortality, risk was 0.41 (0.2, 0.86), compared with blueberry nonconsumers.
CONCLUSION
Higher intakes of berries and flavonoids were associated with a lower overall mortality risk in adult Americans. Few adults regularly consume berries, indicating that increased intake of berries and flavonoid-rich foods may be beneficial to health.
Topics: Adult; Humans; United States; Flavonoids; Fruit; Nutrition Surveys; Anthocyanins; Diet; Flavones; Risk Factors
PubMed: 38184200
DOI: 10.1016/j.tjnut.2024.01.002 -
Associations of Dietary Anthocyanidins Intake with Bone Health in Children: A Cross-Sectional Study.Calcified Tissue International Oct 2023Bone health and body composition share several common mechanisms like oxidative stress and inflammation. Anthocyanins have antioxidant and anti-inflammatory properties....
PURPOSE
Bone health and body composition share several common mechanisms like oxidative stress and inflammation. Anthocyanins have antioxidant and anti-inflammatory properties. We have reported that anthocyanins are associated with better body composition in children, but the associations with bone health have not been elucidated. We aimed to explore the association of anthocyanins with bone mineral content (BMC) and bone mineral density (BMD) at multiple sites in children.
METHODS
In this cross-sectional study, 452 Chinese children aged 6-9 years were recruited. A validated 79-item food frequency questionnaire was used to collect dietary information. BMC and BMD at multiple sites (whole body; whole body excluding head, WBEH; limbs; arms; legs) were measured by dual-energy X-ray.
RESULTS
Higher dietary intake of total anthocyanidins (per one standard deviation increase) was associated with a 1.28-13.6 g (1.31-1.60%, compared to median) higher BMC at all sites and a 3.61-6.96 mg (0.65-0.90%) higher BMD at the whole body, WBEH, and arm sites after controlling for a number of possible covariates. The results were similar and more pronounced for cyanidin, but not for delphinidin and peonidin. Higher dietary intake of cyanidin (per one standard deviation increase) was associated with a 1.33-15.4 g (1.48-1.68%) higher BMC at all sites and a 4.15-7.77 mg (0.66-1.00%) higher BMD at all sites except the legs. No statistically significant associations with BMC or BMD were found for dietary intake of delphinidin and peonidin.
CONCLUSIONS
Higher dietary intake of total anthocyanidins and cyanidins were associated with higher BMC and BMD in Chinese children.
Topics: Humans; Child; Bone Density; Anthocyanins; Cross-Sectional Studies; Antioxidants; Eating
PubMed: 37656219
DOI: 10.1007/s00223-023-01128-6 -
Mini Reviews in Medicinal Chemistry 2021The Mediterranean diet (MD) is becoming a milestone for the prevention of chronic diseases, such as cardiovascular diseases (CVDs), Alzheimer's and Parkinson's disease.... (Review)
Review
The Mediterranean diet (MD) is becoming a milestone for the prevention of chronic diseases, such as cardiovascular diseases (CVDs), Alzheimer's and Parkinson's disease. Ancel Keys in the 1950's showed a low mortality rate, particularly for coronary heart disease, among people resident in the Mediterranean area. The MD is characterized by the intake of the high amount of vegetables, fruit, and cereals and regular but moderate consumption of wine, fish, and dairy products, while olive oil is the main source of culinary fat. Therefore, it is principally a plant-based diet rich in polyphenols, a heterogeneous category of compounds with different properties and bioavailabilities. Among polyphenols, anthocyanins have been combined into the human food regime for centuries. They have been utilized as traditional herbal remedies for their ability to treat several conditions, as potent anti-oxidants, anti-diabetic and anti-carcinogenic compounds. This review summarizes our knowledge on the health-enhancing component of the anthocyanins-rich diet.
Topics: Animals; Anthocyanins; Antidiuretic Agents; Bacteria; Cardiovascular Diseases; Diabetes Mellitus, Experimental; Diet, Mediterranean; Humans; Polyphenols; Protective Agents
PubMed: 33390135
DOI: 10.2174/1389557521999201230200813 -
International Journal of Molecular... Jul 2022Anthocyanidins, the aglycons of anthocyanins, are known, beyond their function in plants, also as compounds with a wide range of biological and pharmacological...
Anthocyanidins, the aglycons of anthocyanins, are known, beyond their function in plants, also as compounds with a wide range of biological and pharmacological activities, including cytostatic effect against various cancer cells. The nature and position of the substituents in the flavylium cation is essential for such biological properties, as well as the equilibrium between the multistate of the different chemical species that are generated by the flavylium cation, including quinoidal base, hemiketal, and - and -chalcones. In this work, eight new flavylium derivatives were synthesized, characterized for confirmation of the structure by FT-IR and 2D-NMR, and investigated in vitro as possible cytostatic compounds against HCT116 and HepG2 cancer cells. The most active two compounds were explored for their halochromic properties that can influence the biological activity and subjected to molecular encapsulation in β-cyclodextrin derivatives in order to increase their solubility in water and bioavailability. The anticancer effect was influenced by the position (6-, 7-, or 8-) of the methoxy group in the β-ring of the methoxy-4'-hydroxy-3'-methoxyflavylium cation, while the study of the halochromic properties revealed the important role played by the chalcone species of the pH-dependent multistate in both the uncomplexed and inclusion complex forms of these anthocyanidins.
Topics: Anthocyanins; Cations; Chalcone; Cytostatic Agents; Spectroscopy, Fourier Transform Infrared
PubMed: 35897679
DOI: 10.3390/ijms23158103 -
Comprehensive Reviews in Food Science... Sep 2022The health benefits of anthocyanins are compromised by their chemical instability and susceptibility to external stress. Researchers found that the interaction between... (Review)
Review
The health benefits of anthocyanins are compromised by their chemical instability and susceptibility to external stress. Researchers found that the interaction between anthocyanins and macromolecular components such as proteins and polysaccharides substantially determines the stability of anthocyanins during food processing and storage. The topic thus has attracted much attention in recent years. This review underlines the new insights gained in our current study of physical and chemical properties and functional properties in complex food systems. It examines the interaction between anthocyanins and food proteins or polysaccharides by focusing on the "structure-stability" relationship. Furthermore, multispectral and molecular computing simulations are used as the chief instruments to explore the interaction's mechanism. During processing and storage, the stability of anthocyanins is generally influenced by the adverse characteristics of food and beverage, including temperature, light, oxygen, enzymes, pH. While the action modes and types between protein/polysaccharide and anthocyanins mainly depend on their structures, the noncovalent interaction between them is the key intermolecular force that increases the stability of anthocyanins. Our goal is to provide the latest understanding of the stability of anthocyanins under food processing conditions and further improve their utilization in food industries. Practical Application: This review provides support for the steady-state protection of active substances.
Topics: Anthocyanins; Beverages; Food; Oxygen; Polysaccharides
PubMed: 36018502
DOI: 10.1111/1541-4337.13026 -
Biomedicine & Pharmacotherapy =... Jul 2023Anthocyanins are colored polyphenolic compounds that belong to the flavonoids family and are largely present in many vegetables and fruits. They have been used in... (Review)
Review
Anthocyanins are colored polyphenolic compounds that belong to the flavonoids family and are largely present in many vegetables and fruits. They have been used in traditional medicine in many cultures for a long time. The most common and abundant anthocyanins are those presenting an O-glycosylation at C-3 (C ring) of the flavonoid skeleton to form -O-β-glucoside derivatives. The present comprehensive review summarized recent data on the anticancer properties of cyanidings along with natural sources, phytochemical data, traditional medical applications, molecular mechanisms and recent nanostrategies to increase the bioavailability and anticancer effects of cyanidins. For this analysis, in vitro, in vivo and clinical studies published up to the year 2022 were sourced from scientific databases and search engines such as PubMed/Medline, Google scholar, Web of Science, Scopus, Wiley and TRIP database. Cyanidins' antitumor properties are exerted during different stages of carcinogenesis and are based on a wide variety of biological activities. The data gathered and discussed in this review allows for affirming that cyanidins have relevant anticancer activity in vitro, in vivo and clinical studies. Future research should focus on studies that bring new data on improving the bioavailability of anthocyanins and on conducting detailed translational pharmacological studies to accurately establish the effective anticancer dose in humans as well as the correct route of administration.
Topics: Humans; Anthocyanins; Phytotherapy; Flavonoids; Phytochemicals; Chemoprevention; Neoplasms; Plant Extracts
PubMed: 37121149
DOI: 10.1016/j.biopha.2023.114783 -
Food Research International (Ottawa,... Dec 2023The absorption and metabolism of bioactive compounds (BCs) in a Hibiscus sabdariffa drink (HbD) were evaluated by the in vivo bioavailability of organic acids (OA) and... (Clinical Trial)
Clinical Trial
The absorption and metabolism of bioactive compounds (BCs) in a Hibiscus sabdariffa drink (HbD) were evaluated by the in vivo bioavailability of organic acids (OA) and phenolic compounds (PC's). An acute single-blind clinical study in humans was conducted. Twelve volunteers consumed a HbD and a control drink (CD). Urine and plasma samples were taken after consuming both beverages. OA and PC's of the beverages (HbD and CD) and the biological samples (urine and plasma) were characterized by HPLC-DAD-MS. Thirthy-eight compounds in HbD and four CD were detected and quantified, equivalent to 937.37 mg and 1.22 mg per 60 mL, respectively. Hibiscus acid was the most abundant OA in both drinks. Additionally, hydroxycinnamic acids, flavonoids, anthocyanins, and anthocyanidins were also detected in HbD, although their amount represented 10% of the total BCs. 25 different metabolites were identified, 15 in urine and 23 in plasma. The microbiota extensively biotransformed PCs and their amount was lower than organic acids, particularly hibiscus acid and hydroxycitric acid. The colonic metabolites derived from PCs and organic acids would be behind the anti-inflammatory bioactivity described for Hibiscus sabdariffa L. (Malvaceae family). However, further studies are necessary to evaluate the metabolites responsible for their anti-inflammatory activity.
Topics: Humans; Anthocyanins; Anti-Inflammatory Agents; Beverages; Biological Availability; Hibiscus; Plant Extracts; Single-Blind Method
PubMed: 37986526
DOI: 10.1016/j.foodres.2023.113581 -
PloS One 2023Computational methods were used to investigate six anthocyanidins exhibiting antidiabetic activity by inhibiting glucokinase regulatory protein (GKRP) activity. Density...
Computational methods were used to investigate six anthocyanidins exhibiting antidiabetic activity by inhibiting glucokinase regulatory protein (GKRP) activity. Density functional theory was used to optimise the geometry of anthocyanidins and calculate their quantum chemical properties. A blind docking method was employed to conduct a molecular docking study, which revealed that delphinidin (Del), cyanidin (Cya), and pelargonidin (Pel) as potential GKRP inhibitors with the lowest binding free energy of -8.7, -8.6, and -8.6 kcal/mol, corresponding to high binding affinity. The molecular dynamics study further verified the blind docking results by showing high GKRP-F1P complex stability and high binding affinity calculated through the MM/GBSA method, upon the binding of pelargonidin. The lower RMSF values of pivotal GK-interacting residues for GKRP-F1P-Pel compared to GKRP-F1P, as a positive control, indicating pelargonidin ability to maintain the inactive conformation of GKRP through the inhibition of GK binding. The key residues that control the binding of the F1P to GKRP and anthocyanidin to GKRP-F1P were also identified in this study. Altogether, pelargonidin is anthocyanidins-derived natural products that have the most potential to act as inhibitors of GKRP and as antidiabetic nutraceuticals.
Topics: Anthocyanins; Molecular Docking Simulation; Carrier Proteins; Hypoglycemic Agents; Glucokinase
PubMed: 37467274
DOI: 10.1371/journal.pone.0288810 -
Comprehensive Reviews in Food Science... Jan 2023Color is an important characteristic of food. Over the last 15 years, more attention has been paid to natural colorants because of the rising demand for clean-label food... (Review)
Review
Color is an important characteristic of food. Over the last 15 years, more attention has been paid to natural colorants because of the rising demand for clean-label food products. Anthocyanins, which are a group of phytochemicals responsible for the purple, blue or red hues of many plants, offer a market advantage. In addition, anthocyanin-rich foods are associated with protection against cardiovascular disease, thrombosis, diabetes, cancer, microbial-based disorders, neurological disorders, and vision ailments. However, the real health value of anthocyanins, whether as a natural colorant or a functional ingredient, is dependent on the ultimate bioaccessibility and bioavailability in the human body. Many animal and human clinical studies revealed that, after intake of anthocyanin-rich foods or anthocyanin extracts, only trace amounts (< 1% of ingested content) of anthocyanins or their predicted metabolites were detected in plasma after a standard blood draw, which was indicative of low bioavailability of anthocyanins. Protein binding to anthocyanins is a strategy that has recently been reported to enhance the ultimate bioactivity, bioaccessibility, and bioavailability of anthocyanins as compared to anthocyanins delivered without a protein carrier. Therefore, in this review, we address anthocyanin properties in food processing and digestion, anthocyanin-protein complexes used in food matrices, and changes in the bioaccessibility and bioavailability of anthocyanins when bound into anthocyanin-protein complexes in foods. Finally, we summarize the challenges and prospects of this delivery system for anthocyanin pigments.
Topics: Animals; Humans; Anthocyanins; Biological Availability; Protein Binding; Food
PubMed: 36398759
DOI: 10.1111/1541-4337.13070