Academic literature on the topic 'Cyanidin-3-O-β-glucoside'

Six new acylated cyanidin glycosides, cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)-(1→2)- O-β-galactopyranoside (1), cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)-(1→2)- O-β-(6′′-malonylgalactopyranoside) (2), cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)- (1→2)- O-β-(6″-succinylgalactopyranoside) (3), cyanidin 3- O-β-(2′'- E-caffeoylglucopyranosyl)-(1→2)- O-β-galactopyranoside-3′- O-β-glucuronopyranoside (4), cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)-(1→2)- O-β-(6′'-malonylgalactopyranoside)-3′- O-β-glucuronopyranoside (5), and cyanidin 3- O-β-(2′'- E-feruloylglucopyranosyl)-(1→2)- O-β-(6′'-malonylgalactoside)-3′- O-β-glucuronopyranoside (6), were isolated from the red flowers of two Clematis cultivars, ‘Niobe'and ‘Madame Julia Correvon'. The chemical structures of the isolated anthocyanins were determined by UV, LC-MS, HPLC, TLC, characterization of hydrolysates, and 1H and 13C NMR spectroscopy, including H-H COSY, C-H COSY, HMBC, HMQC and NOESY. The last three anthocyanins were widely distributed in 37 red flower Clematis cultivars. On the other hand, the first three compounds were found only in two cultivars. Five known flavonol glycosides, kaempferol 3- O-glucoside, kaempferol 3- O-rutinoside, quercetin 3- O-galactoside, quercetin 3- O-glucoside and quercetin 3- O-rutinoside, were isolated from the flowers of ‘Madame Julia Correvon'.

AbstractThe interactions between six anthocyans (cyanidin-3-O-glucoside, delphinidin-3-O-glucoside, malvidin-3-O-glucoside, cyanidin-3-O-rutinoside, delphinidin-3-O-rutinoside, malvidin-3-O-rutinoside) and cyclodextrins were investigated by means of computational techniques. Four different structures of the aforementioned anthocyans were considered, as a result of the dependence structure – pH value (flavylium cations in acidic medium, hemiketals in neutral solutions and two tautomeric quinones in alkaline environment). The results outlined that the anthocyanidin-3-O-rutinoside are favored for the obtaining of inclusion complexes with the cyclodextrins, mostly due to the larger number of OH groups involved in the formation of hydrogen bonds. For all the four types of structures, best results have been obtained for β- and γ-cyclodextrins.

This study investigated the effect of cyanidin-3-O-β-glucoside on an experimental model of partial/transient cerebral ischemia in the rats in order to verify the effectiveness of both pre- and posttreatments. Cyanidin-3-O-β-glucoside-pretreated rats were injected with 10 mg/Kg i.p. 1 h before the induction of cerebral ischemia; in posttreated rats, the same dosage was injected during reperfusion (30 min after restoring blood flow). Cerebral ischemia was induced by bilateral clamping of common carotid arteries for 20 min. Ischemic rats were sacrificed immediately after 20 min ischemia; postischemic reperfused animals were sacrificed after 3 or 24 h of restoring blood flow. Results showed that treatment with cyanidin increased the levels of nonproteic thiol groups after 24 h of postischemic reperfusion, significantly reduced the lipid hydroperoxides, and increased the expression of heme oxygenase andγ-glutamyl cysteine synthase; a significant reduction in the expression of neuronal and inducible nitric oxide synthases and the equally significant increase in the endothelial isoform were observed. Significant modifications were also detected in enzymes involved in metabolism of endogenous inhibitors of nitric oxide. Most of the effects were observed with both pre- and posttreatments with cyanidin-3-O-β-glucoside suggesting a role of anthocyanin in both prevention and treatment of postischemic reperfusion brain damage.

Abstract A new acylated anthocyanin has been isolated from flowers of Nigritella and Orchis and identified as cyanidin 3-O-β-(6”-O-oxalyl)-glucoside on the basis of TLC , HPLC , FABMS, 1H and 13C NMR . This pigment was found to be present in various members of the Orchidaceae.

We investigated the influence of different rootstocks on the content of sugars, organic acids, and antioxidant phenolic compounds in the whole fruit and fruit skin of the European plum cultivar “Čačanska Lepotica”. 1H NMR of the fruit extracts allowed for the identification of sucrose, α- and β-glucose, sorbitol, fructose, and malic and quinic acids, while LC–DAD–ESIMS showed the presence of neochlorogenic and chlorogenic acids, cyanidin-3-O-glucoside, cyanidin-3-O-rutinoside, peonidin-3-O-glucoside, peonidin-3-O-rutinoside, hyperoside, isoquercitrin, rutin, and unidentified quercetin-3-diglycoside. The quantitation of the sugars, malic and quinic acids by 1H NMR and phenolic compounds by HPLC–DAD revealed that the rootstock significantly influenced the content of the individual compounds in the fruit skin and fruit. The fruit grafted on “Wavit” rootstock was characterized by significant amounts of neochlorogenic acid, peonidin-3-O-rutinoside, cyanidin-3-O-rutinoside, and sucrose, while the fruit on “GXN-15” was characterized by high levels of sugars, cyanidin-3-O-glucoside, and malic and chlorogenic acids. The fruit skins of plums grafted on “Wavit” were the richest in sugars, organic acids, and phenolic compounds. A good correlation was observed between the content of total phenolics (TPC), flavonoids (TFC), anthocyanins (TAC), and individual phenolic compounds in the extracts of the fruit and the fruit skins and their antioxidant capacity (DPPH, ABTS, and FRAP).

Li, J., Percival, D., Hoyle, J., Yue, J., White, J., Head, K. and Pruski, K. 2015. Environmental effects on fruit composition of cloudberry/bakeapple (Rubus chamaemorus L.) grown in southern Labrador, Canada. Can. J. Plant Sci. 95: 1167–1175. The composition of fruit collected from three fields located near Lanse'au Clair, Red Bay and Cartwright in southern Labrador, Canada, was analyzed over the 2011 and 2012 growing seasons. Soluble solids, titratable acidity, total phenolics, total anthocyanins, chlorogenic acid, caffeic acid, quercetin-3-glucoside, cyanidin-3-glucoside and ellagic acid were determined after each harvest using standard laboratory procedures. Temperature, precipitation, wind and other environmental factors affected growth and deposition of nutrients in harvested fruit. Soluble solids content (TSS), titratable acidity (TA), total anthocyanin, chlorogenic acid, cyanidin, total phenolic compounds and total anthocyanins of cloudberry fruit were significantly (P<0.05) affected by the combination of the growing season and the location. The TSS, TA and total phenolics were higher in fruits from Cartwright (most northern location) in both seasons compared with the other two locations. The HPLC analysis of compounds showed the ellagic acid and quercetin 3-o-β-D-glucoside contents of fruits were significantly affected by the location and the growing season (higher in 2012 compared with 2011), while contents of chlorogenic acid, caffeic acids, and cyanidin-3-o-β-glucoside were not. To our knowledge this is the most comprehensive study of fruit composition of bakeapple conducted in southern Labrador, Canada.

Obesity is a leading global health problem contributing to various comorbidities, including cardiovascular disease, type II diabetes mellitus (T2DM) and hypertension. Current conventional medical interventions for the treatment of these diseases are limited with varied efficacy and associated side effects. Thus complementary dietary or alternative therapies have become increasingly popular as alternative treatment methods for obesity and its related comorbidities. There is an immense diversity of plant and animal products, which may be effective agents for attenuating the development of obesity, T2DM and hypertension as they often contain a vast array of bioactive compounds that have been associated with significantly positive health outcomes with minimal side effects. However, the effectiveness of many of these foods and their bioactive molecules in the treatment of human diseases has yet to be fully explored. The overall focus of this thesis was to determine the effectiveness of supplementation with blueberry, yoghurt and their important respective bioactive components, cyanidin-3-O-βglucoside (C3G) and peptides, alone or in combination, on the risk factors of obesity and its related comorbidities. To undertake the overall focus of this thesis, the bioactive peptides were extracted from yoghurt and then these peptides as well as C3G were utilised in a human primary skeletal muscle cell culture experiment. This work was further developed with experimentation with these compounds in addition to supplementation with blueberry and yoghurt in isolation and in combination in a high-fat-high-carbohydrate (HFHC) induced obese mouse model. In order to produce bioactive peptides with angiotensin converting enzyme (ACE) inhibitory activity from yoghurt, the optimal fermentation conditions were determined. The results showed that peptides with ACE inhibitory activity (1.47 ± 0.04 mg/mL of IC50 values) were those obtained from yoghurt fermented by 1% of L. helveticus with Flavourzyme® for 12 h. After further separation, one fraction of peptides showed the highest ACE inhibitory activity with an IC50 of 35.75 ± 5.48 μg/mL. The total content of anthocyanidins and C3G in thirteen brands of blueberry samples were also analysed in order to choose the suitable brand for animal experimentation. Based on these results, Bhatti & Manj blueberries were selected attributed to their higher content of total cyanidin. In order to determine the effects of C3G and peptides on the regulation of glucose metabolism, different concentrations of C3G and peptides, alone or in combination, on glucose uptake and mRNA expression of key genes were investigated in human primary skeletal muscle cells derived from obese and obese diabetic (obese T2DM) individuals. The results showed that both low and high concentration of peptides and the combination of these peptides with high C3G concentration significantly enhanced glucose uptake in the presence or absence of insulin in the human primary skeletal muscle cells derived from obese individuals. However, high peptide concentration only increased glucose uptake in the absence of insulin in the obese T2DM group. In the obese group, high concentration of peptide alone and its combination with low C3G down-regulated the mRNA expression of angiotensin II receptor, type 1 (AGTR-1), and up-regulated the mRNA expression of insulin receptor substrate 1 (IRS-1), and glucose transporter 4 (GLUT4). In the obese T2DM group, the expression of AGTR-1 was decreased at high peptide concentration and its combinations with C3G. To further determine whether C3G and peptides, and their original food sources, blueberries and yoghurt, could attenuate obesity and its related comorbidities, a 16-week animal study using HFHC diet induced obese male C57BL/6 mice was conducted. It was found that blueberry and yoghurt alone, and the combination of peptides and C3G significantly reduced both systolic and diastolic blood pressure. Moreover, yoghurt significantly reduced body weight, percentage body fat and improved intraperitoneal glucose tolerance compared to the HFHC (control) group. Furthermore, peptides and its combination with C3G resulted in a significant reduction in percentage body fat and improvement of intraperitoneal glucose tolerance. However, energy expenditure and locomotor behaviour did not alter in any treatment groups compared to the HFHC group. The mRNA expression of multiple genes related to glucose metabolism in the skeletal muscle (extensor digitorum longus (EDL) and soleus) of mice supplemented as detailed above was determined by quantitative ’real-time’ polymerase chain reaction (PCR). In EDL, yoghurt alone up-regulated the expression of AMPK, IRS-1, PI3K and GLUT4, and down-regulated the expression of AGTR-1. The combination of blueberry and yoghurt down-regulated the mRNA expression of AGTR-1 and FoxO1 in EDL. Furthermore, the combination of C3G and peptides also down-regulated the mRNA expression of AGTR-1 and up-regulated the mRNA expression of GLUT4 in EDL. In soleus, blueberry and yoghurt supplementation alone and their combination down-regulated the mRNA expression of AGTR-1, and upregulated the mRNA expression of GLUT4. Therefore, the outcomes of this thesis highlight that yoghurt and its peptides have the potential to reverse or attenuate metabolic disturbances associated with developing obesity, diabetes and hypertension. Blueberries reduced blood pressure while no inhibition on body weight and body fat gain was observed. Furthermore, C3G may not be effective in eliciting beneficial effects on obesity, diabetes and hypertension possibly due to the low dosage utilised. In conclusion, the results presented within the current thesis support that yoghurt as a fermented dairy product may be a beneficial additive to functional foods or utilized as a dietary component. Blueberry plays a significant role in the treatment of hypertension, which represents a potentially promising dietary intervention worthy of further investigation.

This study was conducted to first determine the nutritional potential and the antioxidant activity of black plum fruit pulp and peel. For these characterizations, classic methods were used. The results indicated high fibre and ash contents of black plum from all localities studied, ranging, respectively, from 34.79 ± 0.07–39.83 ± 1.85% and 4.91 ± 0.45–5.91 ± 0.41% for pulp, and 46.38 ± 0.09–50.21 ± 1.07% and 4.16 ± 0.81–4.28 ± 0.20% for peel. The mineral analysis revealed that Black plum pulp and peel are high in potassium (1863.00 ± 1.4–2584.55 ± 3.54 mg/100 g dry weight [DW]) and calcium (355.30 ± 2.52–389.52 ± 3.54 mg/100 g DW). Both the peel and pulp are characterised by a good essential amino acids profile of the protein. The total polyphenol, flavonoid and anthocyanin contents of pulp and peel ranged from 202.51 ± 4.19 to 463.45 ± 6.85 mg gallic acid equivalent (GAE)/100 g of Dry Weight (DW), 75.71 ± 1.03 to 145.55 ± 1.03 mg quercetin equivalent (QE)/100 g DW, and from 1.91 ± 0.08 to 8.28 ± 0.83 mg cyanidin 3-O-β-D-glucoside equivalent (C3GE)/100 g DW respectively. Thus, these fruits constitute a good source of important nutrients for health.