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Food Chemistry Aug 2019Using simple solvent extraction and enzymatic hydrolysis, a rapid LC-MS/MS method for quantification of free and conjugated forms of anthocyanidins and anthocyanins in...
Using simple solvent extraction and enzymatic hydrolysis, a rapid LC-MS/MS method for quantification of free and conjugated forms of anthocyanidins and anthocyanins in plasma and urine samples was developed and validated. A mixed enzymatic treatment containing β-glucuronidase (100 U mL) and sulfatase (2.5 U mL) for 5 min (37 °C; pH 6) was optimal condition for deconjugation of anthocyanidins and anthocyanins in urine and plasma samples. The LC-MS/MS allowed quantifying thirteen different anthocyanidins and anthocyanins simultaneously. The developed LC-MS/MS method was precise and accurate over multiple days and nominal concentrations. The stability assessment study confirmed that the long-term storage and/or periodic use of plasma and urine samples might have a considerable impact on the stability of some anthocyanidins. The method was successfully applied to measure anthocyanidins and anthocyanins in plasma and urine samples following consumption of acute blueberry test meals.
Topics: Anthocyanins; Blood Chemical Analysis; Blueberry Plants; Chromatography, Liquid; Humans; Tandem Mass Spectrometry; Time Factors; Urinalysis
PubMed: 31000056
DOI: 10.1016/j.foodchem.2019.03.109 -
Chemopreventive and therapeutic properties of anthocyanins in breast cancer: A comprehensive review.Nutrition Research (New York, N.Y.) Nov 2022Anthocyanins have received the attention of the scientific community because of their antioxidant, antimetastatic, and cancer-inhibitory properties. The aim of this... (Review)
Review
Anthocyanins have received the attention of the scientific community because of their antioxidant, antimetastatic, and cancer-inhibitory properties. The aim of this review is to comprehensively summarize the possible mechanisms by which anthocyanins exhibit anticarcinogenic properties in breast cancer (BC) cell lines and animal models. Anthocyanins inhibit proinflammatory, signal transducer and activator of transcription 3, and nuclear factor kappa-light-chain-enhancer of activated B cell pathways and increase the activities of detoxification enzymes. In addition, downregulation of metalloproteinases by anthocyanins inhibits tumor invasion and metastatic processes in experimental systems. Anthocyanins mediate anticancer and angiogenic effects by modifying multiple receptor families. Furthermore, inhibition of cell-cycle upstream polo-like kinase signaling, the chromosomal replication checkpoint, and ataxia telangiectasia mutated signaling may contribute to the anticarcinogenic effects of anthocyanins. Finally, anthocyanins induce mitochondrial-mediated apoptosis and downregulate the phosphatidylinositol-3-kinase/AKT/mTOR pathway. In conclusion, anthocyanins have been shown to exert potential antitumor effects against breast carcinogenesis in vitro and in vivo, providing insights into the use of anthocyanins as a natural chemopreventive intervention in BC.
Topics: Animals; Anthocyanins; Signal Transduction; Apoptosis; Anticarcinogenic Agents; Neoplasms
PubMed: 36179643
DOI: 10.1016/j.nutres.2022.08.005 -
Chemical Biology & Drug Design Feb 2023A natural compound cyanidin, which is a type of anthocyanin present in pigmented leaves, fruits, and flowers; distributed widely in berries, apples, and oranges possess... (Review)
Review
A natural compound cyanidin, which is a type of anthocyanin present in pigmented leaves, fruits, and flowers; distributed widely in berries, apples, and oranges possess anticancer activities, thus curing various types of cancer such as breast, liver, lung, prostate, and thyroid cancer. The article provides an insight into the potential of using a single phytochemical, cyanidin to treat various cancer types including breast, liver, lung, prostate, and thyroid cancer. Information about cyanidin and its pharmacological impact on cancer was collected from books, scientific journals, and reports through electronic data search (Web of Science, Scifinder, PubMed, Scopus, Google Scholar, Elsevier, Springer, Wiley, ACS, Science Direct, CNKI as well as Kew Plants of the Word Online) and library. Cyanidin produces its effects against cancer probably by inhibiting (RAS, MAPK) and activating (caspases-3 and P-38) innovative molecular pathways. It may cause cell cycle arrest, cell differentiation processes and changes in redox status which trigger the cytotoxic chemotherapeutic effects. However, it also optimizes the chemotherapeutic targets which are cancer cells less responsive to chemotherapy. Cancer is considered the most widely spread disease and cyanidin from natural origin provides an essential role in treatment of cancer by approaching various mechanistic pathways.
Topics: Humans; Anthocyanins; Medicine, Traditional; Antineoplastic Agents; Thyroid Neoplasms; Plant Extracts
PubMed: 36326796
DOI: 10.1111/cbdd.14173 -
Nutrition Research (New York, N.Y.) Jun 2023The growing rates of obesity worldwide call for intervention strategies to help control the pathophysiological consequences of weight gain. The use of natural foods and... (Review)
Review
The growing rates of obesity worldwide call for intervention strategies to help control the pathophysiological consequences of weight gain. The use of natural foods and bioactive compounds has been suggested as such a strategy because of their recognized antioxidant and anti-inflammatory properties. For example, polyphenols, especially anthocyanins, are candidates for managing obesity and its related metabolic disorders. Obesity is well known for the presence of metainflammation, which has been labeled as an inflammatory activation that leads to a variety of metabolic disorders, usually related to increased oxidative stress. Considering this, anthocyanins may be promising natural compounds able to modulate several intracellular mechanisms, mitigating oxidative stress and metainflammation. A wide variety of foods and extracts rich in anthocyanins have become the focus of research in the field of obesity. Here, we bring together the current knowledge regarding the use of anthocyanins as an intervention tested in vitro, in vivo, and in clinical trials to modulate metainflammation. Most recent research applies a wide variety of extracts and natural sources of anthocyanins, in diverse experimental models, which represents a limitation of the research field. However, the literature is sufficiently consistent to establish that the in-depth molecular analysis of gut microbiota, insulin signaling, TLR4-triggered inflammation, and oxidative stress pathways reveals their modulation by anthocyanins. These targets are interconnected at the cellular level and interact with one another, leading to obesity-associated metainflammation. Thus, the positive findings with anthocyanins observed in preclinical models might directly relate to the positive outcomes in clinical studies. In summary and based on the entirety of the relevant literature, anthocyanins can mitigate obesity-related perturbations in gut microbiota, insulin resistance, oxidative stress and inflammation and therefore may contribute as a therapeutic tool in people living with obesity.
Topics: Humans; Anthocyanins; Obesity; Antioxidants; Insulin Resistance; Inflammation
PubMed: 37201432
DOI: 10.1016/j.nutres.2023.04.004 -
Molecules (Basel, Switzerland) Sep 2019Anthocyanin (AC) is widely used as supplement of eye health in Europe and in East Asia. In this review, I describe AC effects to clarify the mechanism is important in... (Review)
Review
Anthocyanin (AC) is widely used as supplement of eye health in Europe and in East Asia. In this review, I describe AC effects to clarify the mechanism is important in order to understand the effects of AC on vision health. The bioavailability of AC is quite low but, reported as intact form and many kinds of metabolite. And AC passes through the blood-aqueous fluid barrier and blood-retinal barrier. In vitro study, AC had a relaxing effect on ciliary muscle which is important to treat both myopia and glaucoma. And AC stimulate the regeneration of rhodopsin in frog rod outer segment. Furthermore, AC could inhibit the axial length and ocular length elongation in a negative lens-induced chick myopia model. In addition, we summarized clinical studies of AC intake improved dark adaptation and transient myopic shift and the improvement on retinal blood circulation in normal tension glaucoma patients.
Topics: Animals; Anthocyanins; Biological Availability; Dark Adaptation; Eye; Tissue Distribution; Vision, Ocular
PubMed: 31514422
DOI: 10.3390/molecules24183311 -
Chemical Reviews Jan 2022Flavylium compounds are a well-known family of pigments because they are prevalent in the plant kingdom, contributing to colors over a wide range from shades of... (Review)
Review
Flavylium compounds are a well-known family of pigments because they are prevalent in the plant kingdom, contributing to colors over a wide range from shades of yellow-red to blue in fruits, flowers, leaves, and other plant parts. Flavylium compounds include a large variety of natural compound classes, namely, anthocyanins, 3-deoxyanthocyanidins, auronidins, and their respective aglycones as well as anthocyanin-derived pigments (e.g., pyranoanthocyanins, anthocyanin-flavan-3-ol dimers). During the past few decades, there has been increasing interest among chemists in synthesizing different flavylium compounds that mimic natural structures but with different substitution patterns that present a variety of spectroscopic characteristics in view of their applications in different industrial fields. This Review provides an overview of the chemistry of flavylium-based compounds, in particular, the synthetic and enzymatic approaches and mechanisms reported in the literature for obtaining different classes of pigments, their physical-chemical properties in relation to their pH-dependent equilibria network, and their chemical and enzymatic degradation. The development of flavylium-based systems is also described throughout this Review for emergent applications to explore some of the physical-chemical properties of the multistate of species generated by these compounds.
Topics: Anthocyanins; Color; Coloring Agents; Plants; Spectrum Analysis
PubMed: 34843220
DOI: 10.1021/acs.chemrev.1c00399 -
Food Chemistry Nov 2019The chemical compositions and α-glucosidase inhibitory activities of anthocyanins extracted from blueberry, blackcurrant and blue honeysuckle fruits and their acid...
The chemical compositions and α-glucosidase inhibitory activities of anthocyanins extracted from blueberry, blackcurrant and blue honeysuckle fruits and their acid hydrolysates (anthocyanidins) were analysed. Those anthocyanins were glycosidic anthocyanins that converted to anthocyanidins during acid hydrolysis, leading to increases in their α-glucosidase inhibitory activities (expressed as IC values) from 0.232, 0.152 and 0.188 to 0.113 to 0.005 and 0.025 mg/mL. The potential inhibitory mechanism of these anthocyanidins was then investigated through inhibition kinetics, fluorescence quenching and docking simulations. The results showed the following: 1) all anthocyanidins were mixed-type inhibitors of α-glucosidase and they bind more tightly to free α-glucosidase as compared to the α-glucosidase-substrate complex; 2) anthocyanidin inhibition of α-glucosidase was a static procedure, presumably driven by hydrophobic associations and hydrogen bonding; and 3) all anthocyanidins were inserted into the active site of α-glucosidase and avoided the entrance of p-nitrophenyl-a-D-glucopyranoside. This study is valuable for anthocyanidins as potential α-glucosidase inhibitors.
Topics: Anthocyanins; Blueberry Plants; Fluorescence; Fruit; Glycoside Hydrolase Inhibitors; Hydrogen Bonding; Hydrophobic and Hydrophilic Interactions; Kinetics; Lonicera; Molecular Docking Simulation; Ribes; alpha-Glucosidases
PubMed: 31279126
DOI: 10.1016/j.foodchem.2019.125102 -
Journal of Agricultural and Food... Oct 2019Delphinidin (Del) and its glycosides are water-soluble pigments, belonging to a subgroup of flavonoids. They are health-promoting candidates for pharmaceutical and... (Review)
Review
Delphinidin (Del) and its glycosides are water-soluble pigments, belonging to a subgroup of flavonoids. They are health-promoting candidates for pharmaceutical and nutraceutical uses, as indicated by exhibiting antioxidation, anti-inflammation, antimicroorganism, antidiabetes, antiobesity, cardiovascular protection, neuroprotection, and anticancer properties. Glycosylation modification of Del is associated with increased stability and reduced biological activity. Del and its glycosides can be the alternative inhibitors of CBRs, ERα/β, EGFR, BCRP, and SGLT-1, and virtual docking indicates that the sugar moiety may not effectively interact with the active sites of the targets. Structure-based characteristics confer the multifunctional properties of Del and its glycosides. Because of their health-promoting effects, Del and its glycosides are promising and have been developed as potential pharmaceuticals. However, more investigation on the underlying mechanisms of Del and its glycosides in mediating cellular processes with high specificity are still needed. The research progression of Del and its glycosides over the last 10 years is comprehensively reviewed in this article.
Topics: Animals; Anthocyanins; Anti-Infective Agents; Anti-Inflammatory Agents; Antioxidants; Glycosides; Humans; Molecular Structure
PubMed: 31557009
DOI: 10.1021/acs.jafc.9b05079 -
Molecules (Basel, Switzerland) Nov 2019Research on the bioavailability of anthocyanins has focused, historically, on the non-flavonoid (C-C) products that arise from anthocyanins in vivo. However, this review... (Review)
Review
Research on the bioavailability of anthocyanins has focused, historically, on the non-flavonoid (C-C) products that arise from anthocyanins in vivo. However, this review focuses on the products of anthocyanins that still possess the flavonoid structure (C-C-C). Described herein are aspects of the in vivo pool of C-C-C anthocyanin-derived intermediates. Properties related to molecular size, shape, and polarity conveyed by six major anthocyanidin structures are discussed. The presence of a glycoside or not, and a variety of possible phase 2 conjugates, gives rise to a chemically diverse pool of C-C-C intermediates. Chemical properties influence the in vivo stability of anthocyanin-derived products, as well as their suitability as a substrate for xenobiotic conjugation and transport, and their association with the biomatrix. The flavonoid structure is associated with bioactivity and the particular properties of these C-C-C products of anthocyanins determines their deposition in the body, which may influence in vivo processes and ultimately health outcomes.
Topics: Animals; Anthocyanins; Biological Availability; Humans; Xenobiotics
PubMed: 31703276
DOI: 10.3390/molecules24224024 -
Current Drug Discovery Technologies 2020Natural compounds have always played a key role in drug discovery. Anthocyanins are secondary metabolites belonging to the flavonoids family responsible for the purple,... (Review)
Review
Natural compounds have always played a key role in drug discovery. Anthocyanins are secondary metabolites belonging to the flavonoids family responsible for the purple, blue, and red colour of many vegetables and fruits. These phytochemicals have attracted the interest of researchers for their important implications in human health and for their use as natural colorants. Many in vitro and in vivo studies demonstrated the potential effects of anthocyanins and anthocyanins-rich foods in the prevention and/or treatment of diabetes, cancer, and cardiovascular and neurodegenerative diseases. This review reports the recent literature data and focuses on the potential role of anthocyanins in drug discovery. Their biological activity, analysis of structure-activity relationships, bioavailability, metabolism, and future prospects of their uses are critically described.
Topics: Anthocyanins; Biological Availability; Cardiovascular Diseases; Diabetes Mellitus; Drug Discovery; Fruit; Humans; Neoplasms; Neurodegenerative Diseases; Plant Extracts; Structure-Activity Relationship; Vegetables
PubMed: 30686260
DOI: 10.2174/1570163816666190125152931