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Oxidative Medicine and Cellular... 2017The natural phytochemicals present in foods, including anthocyanins, might play a role in attenuating obesity by producing a decrease in weight and adipose tissue. This... (Review)
Review
The natural phytochemicals present in foods, including anthocyanins, might play a role in attenuating obesity by producing a decrease in weight and adipose tissue. This review focused on current knowledge about anthocyanins' role in obesity and its related comorbidities reported in animal models and humans. We summarized their target identification and mechanism of action through several pathways and their final effects on health and well-being. Into consideration of ongoing researches, we highlighted the following key points: a healthy relationship between anthocyanin supplementation and antiobesity effects suffers of the same pros and cons evidenced when the beneficial responses to other phytochemical treatments towards different degenerative diseases have been considered; the different dosage applied in animal versus clinical studies; the complex metabolism and biotransformation to which anthocyanins and phytochemicals are subjected in the intestine and tissues; the possibility that different components present in the supplemented mixtures can interact generating antagonistic, synergistic, or additive effects difficult to predict, and the difference between prevention and therapy. The evolution of the field must seriously consider the need to establish new and adequate cellular and animal models which may, in turn, allow the design of more efficient and prevention-targeted clinical studies.
Topics: Animals; Anthocyanins; Clinical Trials as Topic; Disease Models, Animal; Humans; Obesity
PubMed: 28785373
DOI: 10.1155/2017/2740364 -
The Journal of Nutritional Biochemistry Apr 2023Flavonoids are a major group of phytoestrogens associated with physiological effects, and ecological and social impacts. Although the estrogenic activity of flavonoids... (Review)
Review
Flavonoids are a major group of phytoestrogens associated with physiological effects, and ecological and social impacts. Although the estrogenic activity of flavonoids was reported by researchers in the fields of medical, environmental and food studies, their molecular mechanisms of action have not been comprehensively reviewed. The estrogenic activity of the respective classes of flavonoids, anthocyanidins/anthocyanins, 2-arylbenzofurans/3-arylcoumarins/α-methyldeoxybenzoins, aurones/chalcones/dihydrochalcones, coumaronochromones, coumestans, flavans/flavan-3-ols/flavan-4-ols, flavanones/dihydroflavonols, flavones/flavonols, homoisoflavonoids, isoflavans, isoflavanones, isoflavenes, isoflavones, neoflavonoids, oligoflavonoids, pterocarpans/pterocarpenes, and rotenone/rotenoids, was summarized through a comprehensive literature search, and their structure-activity relationship, biological activities, signaling pathways, and applications were discussed. Although the respective classes of flavonoids contained at least one chemical mimicking estrogen, the mechanisms varied, such as those with estrogenic, anti-estrogenic, non-estrogenic, and biphasic activities, and additional activities through crosstalk/bypassing, which exert biological activities through cell signaling pathways. Such mechanistic variations of estrogen action are not limited to flavonoids and are observed among other broad categories of chemicals, thus this group of chemicals can be termed as the "estrogenome". This review article focuses on the connection of estrogen action mainly between the outer and the inner environments, which represent variations of chemicals and biological activities/signaling pathways, respectively, and form the basis to understand their applications. The applications of chemicals will markedly progress due to emerging technologies, such as artificial intelligence for precision medicine, which is also true of the study of the estrogenome including estrogenic flavonoids.
Topics: Flavonoids; Anthocyanins; Artificial Intelligence; Estrogens; Isoflavones
PubMed: 36509337
DOI: 10.1016/j.jnutbio.2022.109250 -
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 -
Chemical Reviews May 2016Natural anthocyanin pigments/dyes and phenolic copigments/co-dyes form noncovalent complexes, which stabilize and modulate (in particular blue, violet, and red) colors... (Review)
Review
Natural anthocyanin pigments/dyes and phenolic copigments/co-dyes form noncovalent complexes, which stabilize and modulate (in particular blue, violet, and red) colors in flowers, berries, and food products derived from them (including wines, jams, purees, and syrups). This noncovalent association and their electronic and optical implications constitute the copigmentation phenomenon. Over the past decade, experimental and theoretical studies have enabled a molecular understanding of copigmentation. This review revisits this phenomenon to provide a comprehensive description of the nature of binding (the dispersion and electrostatic components of π-π stacking, the hydrophobic effect, and possible hydrogen-bonding between pigment and copigment) and of spectral modifications occurring in copigmentation complexes, in which charge transfer plays an important role. Particular attention is paid to applications of copigmentation in food chemistry.
Topics: Anthocyanins; Color; Coloring Agents; Hydrogen Bonding; Phenols; Pigments, Biological
PubMed: 26959943
DOI: 10.1021/acs.chemrev.5b00507 -
International Journal of Molecular... May 2019Ulcerative colitis (UC), which is a major form of inflammatory bowel disease (IBD), is a chronic relapsing disorder of the gastrointestinal tract affecting millions of... (Review)
Review
Ulcerative colitis (UC), which is a major form of inflammatory bowel disease (IBD), is a chronic relapsing disorder of the gastrointestinal tract affecting millions of people worldwide. Alternative natural therapies, including dietary changes, are being investigated to manage or treat UC since current treatment options have serious negative side effects. There is growing evidence from animal studies and human clinical trials that diets rich in anthocyanins, which are pigments in fruits and vegetables, protect against inflammation and increased gut permeability as well as improve colon health through their ability to alter bacterial metabolism and the microbial milieu within the intestines. In this review, the structure and bioactivity of anthocyanins, the role of inflammation and gut bacterial dysbiosis in UC pathogenesis, and their regulation by the dietary anthocyanins are discussed, which suggests the feasibility of dietary strategies for UC mitigation.
Topics: Animals; Anthocyanins; Anti-Inflammatory Agents; Colitis, Ulcerative; Dietary Supplements; Humans
PubMed: 31137777
DOI: 10.3390/ijms20102588 -
Molecules (Basel, Switzerland) Jan 2021Wine is one of the most consumed beverages around the world. It is composed of alcohols, sugars, acids, minerals, proteins and other compounds, such as organic acids and... (Review)
Review
Wine is one of the most consumed beverages around the world. It is composed of alcohols, sugars, acids, minerals, proteins and other compounds, such as organic acids and volatile and phenolic compounds (also called polyphenols). Polyphenols have been shown to be highly related to both (i) wine quality (color, flavor, and taste) and (ii) health-promoting properties (antioxidant and cardioprotective among others). Polyphenols can be grouped into two big families: (i) Flavonoids, including anthocyanidins, flavonols, flavanols, hydrolysable and condensed tannins, flavanones, flavones and chalcones; and (ii) Non-flavonoids, including hydroxycinnamic acids, hydroxybenzoic acids, stilbenes, tyrosol and hydroxytyrosol. Each group affects in some way the different properties of wine to a greater or a lesser extent. For that reason, the phenolic composition can be managed to obtain singular wines with specific, desirable characteristics. The current review presents a summary of the ways in which the phenolic composition of wine can be modulated, including (a) invariable factors such as variety, field management or climatic conditions; (b) pre-fermentative strategies such as maceration, thermovinification and pulsed electric field; (c) fermentative strategies such as the use of different yeasts and bacteria; and (d) post-fermentative strategies such as maceration, fining agents and aging. Finally, the different extraction methods and analytical techniques used for polyphenol detection and quantification have been also reviewed.
Topics: Alcohols; Anthocyanins; Antioxidants; Flavonoids; Flavonols; Polyphenols; Taste; Wine
PubMed: 33573150
DOI: 10.3390/molecules26030718 -
Molecules (Basel, Switzerland) Jul 2022Anthocyanins are water-soluble pigments present in fruits and vegetables, which render them an extensive range of colors. They have a wide distribution in the human... (Review)
Review
Anthocyanins are water-soluble pigments present in fruits and vegetables, which render them an extensive range of colors. They have a wide distribution in the human diet, are innocuous, and, based on numerous studies, have supposed preventive and therapeutical benefits against chronic affections such as inflammatory, neurological, cardiovascular, digestive disorders, diabetes, and cancer, mostly due to their antioxidant action. Despite their great potential as pharmaceutical applications, they have a rather limited use because of their rather low stability to environmental variations. Their absorption was noticed to occur best in the stomach and small intestine, but the pH fluctuation of the digestive system impacts their rapid degradation. Urine excretion and tissue distribution also occur at low rates. The aim of this review is to highlight the chemical characteristics of anthocyanins and emphasize their weaknesses regarding bioavailability. It also targets to deliver an update on the recent advances in the involvement of anthocyanins in different pathologies with a focus on in vivo, in vitro, animal, and human clinical trials.
Topics: Animals; Anthocyanins; Cardiovascular Diseases; Diabetes Mellitus; Fruit; Phytochemicals; Vegetables
PubMed: 35807504
DOI: 10.3390/molecules27134254 -
Cancer Letters May 2017Over the last two decades, berries and berry bioactives, particularly anthocyanins and their aglycones anthocyanidins (Anthos) have demonstrated excellent anti-oxidant,... (Comparative Study)
Comparative Study
Over the last two decades, berries and berry bioactives, particularly anthocyanins and their aglycones anthocyanidins (Anthos) have demonstrated excellent anti-oxidant, anti-proliferative, apoptotic and anti-inflammatory properties. However, their physicochemical and pharmacokinetic limitations such as, low permeability, and poor oral bioavailability are considered as unfavorable properties for development as drugs. Therefore there is a need to develop systems for efficient systemic delivery and robust bioavailability. In this study we prepared nano-formulation of bilberry-derived Anthos using exosomes harvested from raw bovine milk. Exosomal formulation of Anthos enhanced antiproliferative and anti-inflammatory effects compared with the free Anthos against various cancer cells in vitro. Our data also showed significantly enhanced therapeutic response of exosomal-Anthos formulation compared with the free Anthos against lung cancer tumor xenograft in nude mice. The Anthos showed no signs of gross or systemic toxicity in wild-type mice. Thus, exosomes provide an effective alternative for oral delivery of Anthos that is efficacious, cost-effective, and safe, and this regimen can be developed as a non-toxic, widely applicable therapeutic agent.
Topics: A549 Cells; Administration, Oral; Animals; Anthocyanins; Anti-Inflammatory Agents; Antineoplastic Agents, Phytogenic; Cell Proliferation; Dose-Response Relationship, Drug; Drug Carriers; Drug Compounding; Exosomes; Female; HCT116 Cells; Humans; MCF-7 Cells; Male; Mice, Nude; Milk; Nanoparticles; Time Factors; Tumor Burden; Xenograft Model Antitumor Assays
PubMed: 28202351
DOI: 10.1016/j.canlet.2017.02.004 -
Journal of Agricultural and Food... May 2014Dietary polyphenols may contribute to the prevention of several degenerative diseases, including cancer. Anthocyanins have been shown to possess potential anticancer...
Dietary polyphenols may contribute to the prevention of several degenerative diseases, including cancer. Anthocyanins have been shown to possess potential anticancer activity. The aim of this study was to determine anthocyanin bioavailability in lung tissue of mice fed a blueberry diet (5% w/w) for 10 days or a bolus dose (10 mg/mouse; po) of a native mixture of bilberry anthocyanidins. All five anthocyanidins present in the blueberry were detected in the lung tissue using improved methods. The effect of various solvents on the stability of anthocyanins and their recovery from the biomatrix was analyzed. Detection of anthocyanins and their metabolites was performed by UPLC and LC-MS. Although anthocyanins were not detected, cyanidin was detected by UPLC-PDA and other anthocyanidins were detected by LC-MS, following conversion to anthocyanidins and selective extraction in isoamyl alcohol. The results show that anthocyanins can be detected in lung tissue of blueberry-fed mice and thus are bioavailable beyond the gastrointestinal tract.
Topics: Animals; Anthocyanins; Blueberry Plants; Chromatography, High Pressure Liquid; Female; Lung; Mass Spectrometry; Mice; Mice, Nude; Plant Extracts
PubMed: 24650213
DOI: 10.1021/jf500467b -
Redox Biology May 2022This study investigated the effects of supplementation with a cyanidin- and delphinidin-rich extract (CDRE) on the postprandial dysmetabolism, inflammation, and redox... (Randomized Controlled Trial)
Randomized Controlled Trial
This study investigated the effects of supplementation with a cyanidin- and delphinidin-rich extract (CDRE) on the postprandial dysmetabolism, inflammation, and redox and insulin signaling, triggered by the consumption of a high fat meal (HFM) in healthy individuals. Participants (n = 25) consumed a 1026-kcal HFM simultaneously with either the CDRE providing 320.4 mg of anthocyanins (90% cyanidin and delphinidin) or placebo. Diets were randomly assigned in a double blind, placebo-controlled crossover design. Blood was collected prior to (fasted, time 0), and for 5 h after meal consumption; plasma, serum, and peripheral blood mononuclear cells (PBMC) were isolated. AC metabolites were detected in serum as early as 30 min after CDRE consumption. The CDRE mitigated HFM-induced endotoxemia, reducing increases in plasma LPS and LPS-binding protein. The CDRE also reduced other events associated with HFM-triggered postprandial dysmetabolism including: i) plasma glucose and triglyceride increases; ii) TNFα and NOX4 upregulation in PBMC; and iii) JNK1/2 activation in PBMC. The CDRE did not significantly affect HFM-mediated increases in plasma insulin, GLP-1, GLP-2, GIP, and LDL- and HDL-cholesterol, and IKK phosphorylation in PBMC. In summary, dietary AC, i.e. cyanidin and delphinidin, exerted beneficial actions against unhealthy diets by modulating the associated postprandial dysmetabolism, endotoxemia, alterations of glycemia and lipidemia, and redox and insulin signaling.
Topics: Anthocyanins; Blood Glucose; Cross-Over Studies; Diet, High-Fat; Endotoxemia; Healthy Volunteers; Humans; Insulin; Leukocytes, Mononuclear
PubMed: 35255426
DOI: 10.1016/j.redox.2022.102273