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Coronavirus epidemic 2019 (COVID-19), caused by novel coronavirus (2019-nCoV), is newly increasing worldwide and elevating global health concerns. Similar to SARS-CoV and MERS-CoV, the viral key 3-chymotrypsin-like cysteine protease enzyme (3CLPro), which controls 2019-nCoV duplications and manages its life cycle, could be pointed as a drug discovery target. Herein, we theoretically studied the binding ability of 10 structurally different anthocyanins with the catalytic dyad residues of 3CLpro of 2019-nCoV using molecular docking modelling. The results revealed that the polyacylated anthocyanins, including phacelianin, gentiodelphin, cyanodelphin, and tecophilin, were found to authentically bind with the receptor binding site and catalytic dyad (Cys145 and His41) of 2019-nCoV-3CLpro. Our analyses revealed that the top four hits might serve as potential anti-2019-nCoV leading molecules for further optimization and drug development process to combat COVID-19. This study unleashed that anthocyanins with specific structure could be used as effective anti-COVID-19 natural components.
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.
Overconsumption of energy dense foods and sedentary lifestyle are considered as major causes of obesity-associated insulin resistance and abnormal glucose metabolism. Results from both cohort studies and randomized trials suggested that anthocyanins from berries may lower metabolic risks, however these reports are equivocal. The present study was designed to examine effects of six berries with structurally diverse anthocyanin profiles (normalized to 400 µg/g total anthocyanin content) on development of metabolic risk factors in the C57BL/6 mouse model of polygenic obesity. Diets supplemented with blackberry (mono-glycosylated cyanidins), black raspberry (acylated mono-glycosylated cyanidins), blackcurrant (mono- and di-glycosylated cyanidins and delphinidins), maqui berry (di-glycosylated delphinidins), Concord grape (acylated mono-glycosylated delphinidins and petunidins), and blueberry (mono-glycosylated delphinidins, malvidins, and petunidins) showed a prominent discrepancy between biological activities of delphinidin/malvidin-versus cyanidin-type anthocyanins that could be explained by differences in their structure and metabolism in the gut. Consumption of berries also resulted in a strong shift in the gastrointestinal bacterial communities towards obligate anaerobes that correlated with decrease in the gastrointestinal luminal oxygen and oxidative stress. Further work is needed to understand mechanisms that lead to nearly anoxic conditions in the gut lumens, including the relative contributions of host, diet and/or microbial oxidative activity, and their implication to human health.
Anthocyanins are dietary flavonoids commonly consumed in the diet, which have been suggested to have a preventative effect on cardiovascular disease (CVD) development among epidemiological studies. We systematically reviewed randomized controlled trials (RCTs) testing the effects of purified anthocyanins and anthocyanin-rich extracts on markers of CVD (triglycerides, total cholesterol, low-density lipoprotein (LDL) cholesterol, high-density lipoprotein (HDL) cholesterol, and blood pressure) in both healthy and diseased populations. Eligible studies included RCTs of adults published in English. We searched PubMed, Web of Science Core Collection, and BIOSIS Previews for relevant articles from inception until 1 July 2014. Twelve RCTs representing 10 studies were included in this review. Supplementation with anthocyanins significantly improved LDL cholesterol among diseased individuals or those with elevated biomarkers. Supplementation did not significantly affect other markers of CVD in either healthy individuals or those with elevated markers. No adverse effects of anthocyanins were reported across studies at levels up to 640 mg/day. Limitations of trials in the qualitative analyses include short trial duration and large variability in the dose administered within the trials. Longer-duration trials assessing dose response are needed to adequately determine whether an effect of supplementation exists.
Nonalcoholic fatty liver disease (NAFLD) is a common chronic disease that threatens human health, and present therapies remain limited due to the lack of effective drugs. Lipid metabolic disturbance and oxidative stress have strong links to the development of NAFLD, while autophagy was generally accepted as a key regulatory mechanism on these steps. Our previous studies indicated that cherry anthocyanins (CACN) protected against high fat diet-induced obesity and NALFD in C57BL/6 mice, while the underlying molecule mechanism is still unclear. Thus, in this study, we show that CACN protect against oleic acid- (OA-) induced oxidative stress and attenuate lipid droplet accumulation in NAFLD cell models. According to the results of a transmission electron microscope (TEM), western blot, immunofluorescence (IF), and adenovirus transfection (Ad-mCherry-GFP-LC3B), autophagy is in accordance with the lipid-lowering effect induced by CACN. Further studies illustrate that CACN may activate autophagy via mTOR pathways. In addition, an autophagy inhibitor, 3-methyladenine (3-MA), was applied and the result suggested that autophagy indeed participates in the lipid clearance process in OA-induced lipid accumulation. All these results indicate that the positive effects of CACN on OA-induced hepatic lipid accumulation are mediated via activating autophagy, showing a potential target for the therapeutic strategy of NAFLD.
Isolated anthocyanins have limited colonic bioavailability due to their instability as free forms. Thus, many methods have been fabricated to increase the stability of anthocyanins. Complexation, encapsulation, and co-pigmentation with other pigments, proteins, metal ions, and carbohydrates have been reported to improve the stability and bioavailability of anthocyanins. In this study, anthocyanins extracted from purple potatoes were complexed with four different polysaccharides and their mixture. The anthocyanin-polysaccharide complexes were characterized using a zeta potential analyzer, particle size analyzer, scanning electron microscopy, and Fourier-transform infrared spectroscopy. Complexes were subjected to simulated digestion for assessing the stability of anthocyanins. Furthermore, complexes were subjected to different pH conditions and incubated at high temperatures to monitor color changes. A Caco-2 cell monolayer was used to evaluate the colonic concentrations of anthocyanins. In addition, the bioactivity of complexes was assessed using LPS-treated Caco-2 cell monolayer. Results show that pectin had the best complexation capacity with anthocyanins. The surface morphology of the anthocyanin-pectin complex (APC) was changed after complexation. APC was more resistant to the simulated upper gastrointestinal digestion, and high pH and temperature conditions for a longer duration. Furthermore, APC restored the lipopolysaccharide (LPS)-induced high cell permeability compared to isolated anthocyanins. In conclusion, complexation with pectin increased the stability and colonic bioavailability and the activity of anthocyanins.
Nitrogen (N) is a major nutrient of plants but often a limiting factor for plant growth and crop yield. To adapt to N deficiency, plants have evolved adaptive responses including accumulation of anthocyanins. However, it is still unclear whether the accumulated anthocyanins are part of the components of plant tolerance under low N stress. Here, we demonstrate that low N-induced anthocyanins contribute substantially to the low N tolerance of Arabidopsis thaliana. pap1-1, a mutant defective in MYB75 (PAP1), a MYB-type transcription factor that positively regulates anthocyanin biosynthesis in Arabidopsis, was found to have significantly decreased survival rate to low N stress compared to its wild-type plants. Similarly, tt3, a mutant with severe deficiency in dihydroflavonol 4-reductase (DFR), a key enzyme in anthocyanin biosynthesis, also showed much lower survival rate under low N stress. These results indicate that anthocyanins are substantial contributors of plant tolerance to low N stress. Furthermore, a metabolomics analysis using LC-MS revealed changes in flavonoid profile in the pap1-1 and tt3 plants, which established a causal relationship between plant adaptation to low N stress and these compounds including anthocyanins. Our results showed an important role of anthocyanins rather than flavonols in conferring plant tolerance to low N stress.
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.
Yellow to red colored betalains are a chemotaxonomic feature of Caryophyllales, while in most other plant taxa, anthocyanins are responsible for these colors. The carnivorous plant family Nepenthaceae belongs to Caryophyllales; here, red-pigmented tissues seem to attract insect prey. Strikingly, the chemical nature of red color in Nepenthes has never been elucidated. Although belonging to Caryophyllales, in Nepenthes, some molecular evidence supports the presence of anthocyanins rather than betalains. However, there was previously no direct chemical proof of this. Using ultra-high-performance liquid chromatography-electrospray ionization-high-resolution mass spectrometry, we identified cyanidin glycosides in Nepenthes species and tissues. Further, we reveal the existence of a complete set of constitutively expressed anthocyanin biosynthetic genes in Nepenthes. Thus, here we finally conclude the long-term open question regarding red pigmentation in Nepenthaceae.
Haskap berries are one of the richest natural sources of anthocyanins and their extracts can be used for nutraceuticals and functional food ingredients. Deep eutectic solvents (DES) comprising food-grade or generally recognized as safe (GRAS) components show promise as natural solvents, but have not been applied to haskap berries. Thus, the aim of this study is to investigate the extraction of anthocyanins from haskap berries using a DES consisting of citric acid and d-(+)-maltose.
This study aimed to determine anthocyanins and their antioxidative and cardioprotective properties in defatted dabai parts. Anthocyanins in crude extracts and extract fractions of defatted dabai peel and pericarp were quantified using UHPLC, while their antioxidant capacity and oxidative stress inhibition ability were evaluated by using DPPH and CUPRAC assays as well as linoleic acid oxidation system, hemoglobin oxidation, and PARP-1 inhibition ELISA. Cardioprotective effect of the defatted dabai peel extract was evaluated using hypercholesterolemic-induced New Zealand white rabbits. Six anthocyanins were detected in the defatted dabai peel, with the highest antioxidant capacities and oxidative stress inhibition effect compared to the other part. The defatted dabai peel extract has also inhibited lipid peroxidation (plasma MDA) and elevated cellular antioxidant enzymes (SOD and GPx) in the tested animal model. Major anthocyanin (cyanidin-3-glucoside) and other anthocyanins (pelargonidin-3-glucoside, malvidin-3-glucoside, cyanidin-3-galactoside, cyanidin-3-arabinoside, and peonidin-3-glucoside) detected in the defatted dabai peel are potential future nutraceuticals with promising medicinal properties.
In the present-day scenario, wherein histotechnological laboratory personnel come into contact with numerous hazardous chemicals every day, laboratories are emphasizing on development of safer and environment-friendly alternatives globally which are easily available and feasible. In this context, we have attempted to utilize anthocyanins, a family of pigments naturally occurring in fruits and flowers and which are already used as natural food colorants, for assessing their utility as histological stains.
Over the past decades, there has been a growing interest in using natural molecules with therapeutic potential for biomedical applications. In this context, our aim is focused on anthocyanins (AN) as molecules with anticancer properties that could be used in melanoma local therapies. Due to their susceptibility to environmental changes, current study is based on the design and development of a fluorescent system for carrying and trafficking AN inside melanoma cells. The architectural structure of the proposed system CaCO3(PAH)@RBITC@AN reflects a spherical shape, 1080 nm diameter and a solid groundwork CaCO3(PAH), on which rhodamine B isothiocyanate (RBITC) fluorophore was firstly added; then, poly(acrylic acid) (PAA) polyelectrolytes and poly(allylamine hydrochloride) (PAH) were successfully deposited. Purified AN from chokeberries were entrapped between PAA layers (rate of 94.6%). In vitro tests confirmed that CaCO3(PAH)@RBITC@AN does not affect the proliferation of melanoma B16-F10 cells and proved that their internalization and trafficking can be followed after 24 h of treatment. Data presented here could contribute not only to the existing knowledge about the encapsulation technology of AN but also might bring relevant information for a novel formula to deliver therapeutic molecules or other bio-imaging agents directly into melanoma cells, a strategy that could positively improve tumor therapies.
Roselle is rich in anthocyanins and is traditionally used to prepare a bright red beverage by decoction. However, heat treatment and different pH environments are often encountered during food processing, and these factors are often detrimental to anthocyanins. Therefore, it is very important to understand the influence of pH and heat treatment on anthocyanins for the application of roselle. This study determined the antioxidant properties of roselle extract, explored changes in the color and anthocyanin content in different pH environments, and evaluated the thermal stability of roselle anthocyanins using kinetic equations. The results showed that the roselle extract is rich in anthocyanins and has good antioxidant capacity (DPPH IC50 = 4.06 mg/mL, ABTS IC50 = 3.7 mg/mL). The anthocyanins themselves exhibited a certain degree of heat resistance and good color stability in an acidic environment. In contrast, they degraded very quickly and exhibited significant changes in color in a low-acid environment. The activation energy (Ea) ranges of the anthocyanins in the acidic and low-acid environments were quite different at 55.8⁻95.7 and 31.4⁻74.9 kJ/mol, respectively. Thus, it can be concluded that roselle anthocyanins are susceptible to heat treatment in a low-acid environment, affecting their quality and appearance; however, they can serve as a good source of functional ingredients and color in an acidic environment.
We sought to explore the effect of blueberry anthocyanins-enriched extracts (BAE) on cyclophosphamide (CTX)-induced cardiac injury. The rats were divided randomly into five groups including normal control, CTX 100 mg/kg, BAE 80mg/kg, CTX+BAE 20mg/kg and CTX+BAE 80mg/kg groups. The rats in the three BAE-treated groups were administered BAE for four weeks. Seven days after BAE administration, rats in CTX group and two BAE-treated groups were intraperitoneally injected with a single dose of 100 mg/kg CTX. Cardiac injury was assessed using physiological parameters, Echo, morphological staining, real-time PCR and western blot. In addition, cardiotoxicity indices, inflammatory cytokines expression and oxidative stress markers were also detected. Four weeks 20mg/kg and 80mg/kg dose of BAE treatment following CTX exposure attenuated mean arterial blood pressure, heart rate and activities of heart enzymes, improved cardiac dysfunction, left ventricular hypertrophy and fibrosis. Importantly, BAE also attenuated CTX-induced LV leukocyte infiltration and inflammatory cytokines expression, ameliorated oxidative stress as well as cardiomyocyte apoptosis. In conclusion, BAE attenuated the CTX-induced cardiac injury and the protective mechanisms were related closely to the anti-inflammatory, antioxidant and anti-inflammatory characteristics of BAE.
Elderberries are known for their high anthocyanins content, which have been shown to possess anti-proliferative and anti-cancer effects. Anthocyanins enriched extract (AEE) was obtained from elderberries and was characterized by LC/DAD/ESI-MS analysis. Five cyanidin-based anthocyanins were identified, among which Cy-3-O-samb was the major compound (51%). The total anthocyanins content of AEE was 495 mg Cy-3-O-samb/100 g FW. AEE inhibited proliferation of metastatic B16-F10 murine melanoma cells, in a concentration-dependent manner, with an IC50 of 264.3 μg/mL. LDH (lactate dehydrogenase), as a marker of membrane integrity, increased 74% in B16-F10 cells treated with 250 μg/mL AEE, compared to control. It was observed that apoptosis is the mechanism of melanoma cell death after AEE treatment, confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis. These results indicate that elderberry-derived anthocyanins might be utilized in future applications as topical adjuvant in skin cancer therapy.
The fruits of Aronia melanocarpa are well known due to their high anthocyanin content that may be effective in preventing certain health disorders arising from oxidative stress. Various polyphenolic compounds such as anthocyanins and flavonoids are responsible for the multiple effects of chokeberry. The aim of this study was to determine in vitro how active the black chokeberry anthocyanins are in scavenging radicals and to evaluate in vivo their immunomodulating capacity. Using the method of column chromatography, we extracted the anthocyanins of black chokeberries, i.e., cyanidin-3-O-galactoside with a purity of over 93.7%. Using HPLC and spectrophotometric analysis, the flavonoid content was determined. Following the analysis of the tests with AAPH and DPPH, the chokeberry cyanidin-3-O-galactoside was found much better than individual anthocyanins in regard to antioxidant capacity. The range of concentrations was revealed, showing the protective effect of anthocyanins on the RPMI-1788 cell culture against cyclophosphamide, as well as against osmotic and peroxide hemolysis. An immunomodulating effect on the functional activity of phagocytes was revealed in vivo as a result of oral administration of chokeberry cyanidin-3-O-galactoside and a mixture composed of cyanidin-3-O-glucoside and cyanidin-3-O-galactoside standards. Consequently, anthocyanins, in particular cyanidin-3-O-galactoside, play an important role, demonstrating immunomodulating effects when chokeberries are consumed.
Bestrophin, an integral membrane protein existing in basolateral region of the retina is a propitious target for drug discovery. Mutations in the Bestrophin protein cause Best Vitelliform Macular Dystrophy (BVMD) leading to retinal damages and loss of visual acuity. Owing to the lack of three dimensional structure and related structural homologs in the protein data bank, we modeled the bestrophin protein using Robetta ab initio method. Further, no treatment is available for the disease. In this situation, anthocyanins from natural sources are reported to combat retinal damages. Hence, we identified anthocyanins from Syzygium cumini fruit skin using Electrospray Ionization tandem mass spectrometry. These compounds were docked into the predicted bestrophin model to study the interactions within the active site. The results may provide a valuable insight into the structure of bestrophin and efficacy of anthocyanins in molecular docking studies.
High-fat (HF) diets are thought to disrupt the profile of the gut microbiota in a manner that may contribute to the neuroinflammation and neurobehavioral changes observed in obesity. Accordingly, we hypothesize that by preventing HF-diet induced dysbiosis it is possible to prevent neuroinflammation and the consequent neurological disorders. Anthocyanins are flavonoids found in berries that exhibit anti-neuroinflammatory properties in the context of obesity. Here, we demonstrate that the blackberry anthocyanin-rich extract (BE) can modulate gut microbiota composition and counteract some of the features of HF-diet induced dysbiosis. In addition, we show that the modifications in gut microbial environment are partially linked with the anti-neuroinflammatory properties of BE. Through fecal metabolome analysis, we unravel the mechanism by which BE participates in the bilateral communication between the gut and the brain. BE alters host tryptophan metabolism, increasing the production of the neuroprotective metabolite kynurenic acid. These findings strongly suggest that dietary manipulation of the gut microbiota with anthocyanins can attenuate the neurologic complications of obesity, thus expanding the classification of psychobiotics to anthocyanins.
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