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The use of kinetic modeling data for the extraction of bioactive compounds is essential for food industries. This work aimed to investigate which mathematical model best fits the extraction of bioactive compounds from camu-camu peel and to evaluate the effect of drying by hot air convection (60 ºC). Four mathematical models (parabolic diffusion, power law, hyperbolic and pseudo-second order) were applied to assess the extraction conditions. To describe the kinetics and data modeling the peels went through ultrasound-assisted extraction (UAE) for 1 h, 6 h, 12 h, and 24 h with water and water-ethanol (50:50 v/v) as solvents. The hyperbolic and pseudo-second order mathematical models presented the best fitting to the experimental data with lower values of γ ², MSE, RMSE, and NRMSE, in addition to values closer to 1 for EF. The extracts went through UPLC-MS/MS and nine compounds were identified in the peels: cyanidin 3-o-glucoside, delphinidin, quercetin, myricetin, rutin, gallic acid, chlorogenic acid p-coumaric and ellagic acid. Therefore, dried camu-camu peels still have antioxidant potential, especially when extracted for 12 h with water-ethanol (50:50 v/v) as solvent. [Display omitted] • The selection of fruits was based on the color of the peel: green and red. • Extraction was performed in an ultrasonic bath in indirect contact. • Best results were obtained with ethanol/water (v/v) and extraction times of 12 and 24 h. • Hyperbolic and pseudo-second kinetic model presented the best fits. • The use of UPLC-MS/MS resulted in the determination of 9 bioactive compounds types. [ABSTRACT FROM AUTHOR]

Veggie chips have gained popularity in the European market. These are considered healthier than potato chips by consumers. However, few works evaluate their nutritional and digestibility. The current work aimed to evaluate the effect of four pre-frying treatments (soaking, blanching, pulsed electric field (PEF) and PEF + blanching combination (PEF B)) on the chemical composition, anthocyanins, acrylamide, and digestive behavior (starch hydrolysis and anthocyanins bioaccessibility) of purple sweet potato deep-fried chips. In total 15 independent batches were made, three for each studied treatment (also a control without pretreatment was developed). The studied pretreatments impacted on fat and starch content, especially blanching and PEF B, which caused an increase in fat absorption and break starch, generating maltodextrins. Nineteen anthocyanins were detected, mainly cyanidin and peonidin derivatives, but a drastic loss was observed in blanched, PEF-treated and PEF-B-Treated chips. Acrylamide values ranged from 504.11 to 6350.0- μg/kg, with the highest values reported by untreated chips and the lowest by PEF-B-treated chips (p < 0.05). The anthocyanin's bioaccessibility ranged between 66.57 and 92.88%, with soaked chips that showed the highest values. • Pretreatments modified starch content, blanching caused loss and hydrolysis, whereas PEF prevented hydrolysis • Blanching and PEF+ Blanching promotes oil updates in purple sweet potato chips • PEF+ Blanching reduced around 76.5% the amount of acrylamide in purple sweet potato chips • Soaking improves mineral and anthocyanin content, whereas blanching and PEF promote dramatic loose • All pretreatments increase starch hydrolysis after in vitro gastrointestinal digestion • Purple sweet potato chips presented the highest anthocyanins bioaccessibility, up to 65% [ABSTRACT FROM AUTHOR]

Alicyclobacillus acidoterrestris is a bacterium known for causing spoilage in the taste and odour of fruit juices due to its thermoacidophilic nature. Its spoilage is attributed to the formation of guaiacol, which requires the presence of suitable precursors in the juices that A. acidoterrestris can metabolize. Therefore, A. acidoterrestris could exhibit different behaviour depending on the physicochemical characteristics the juice. In this study, we aimed to evaluate the behaviour of five A. acidoterrestris strains in seven different fruit juices by monitoring total cell and spore populations and quantifying guaiacol production. Also, physicochemical and phenolic profile, focusing on antimicrobials and guaiacol precursors, were analysed to better understand differences. Results showed growth in orange, apple, and plum juices for all the tested strains, with total cell populations reaching approximately 7 log cfu/mL, except for plum juice. In persimmon juice, growth was only observed in 3 out of 5 strains, for both total cells and spores. In contrast, all strains were inhibited in peach, black grape, and strawberry juices, maintaining a consistent population around 4 log cfu/mL. A strong negative correlation was observed between bacterial population and compounds such as kaempferol (for strains R3, R111, and P1), cyanidin chloride (for strains R111 and P1), and p-coumaric acid (for strain 7094 T). Regarding guaiacol production, orange and persimmon juices exhibited the highest guaiacol levels, with strain P1 (362.3 ± 12.6 ng/mL) and strain EC1 (325.1 ± 1.4 ng/mL) as the top producers, respectively. Plum, black grape, and strawberry juices showed similar guaiacol concentrations (16.9 ± 2.8 to 105.0 ± 33.7 ng/mL). Vanillin was showed positive correlations with guaiacol production in almost all strains (7094 T, R3, R111, and P1), with correlation coefficients of 0.97, 0.99, 0.82, and 0.87, respectively. We have reported different behaviour of A. acidoterrestris strains depending on juice type. Despite growth inhibition observed in some juices, enough guaiacol quantities to spoil the juice can be produced. This highlights the necessity of exploring strategies to prevent guaiacol production, even under growth restriction. • All A. acidoterrestris tested strains grew in orange, apple, and plum juices. • In persimmon juice, only strains R111, P1, and EC1 were able to grow. • Strains P1 and EC1 were the top guaiacol producers in orange and persimmon juices. • Kaempferol, cyanidin chloride, and p-coumaric acid correlated negatively with growth. • Vanillin correlated with guaiacol production in strains 7094 T, R3, R111, and P1. [ABSTRACT FROM AUTHOR]

Anthocyanins are important naturally occurring flavyliums with antioxidant activity produced by many plant species. In recent years there has been growing interest in the use of anthocyanin extracts as nutraceutical supplements, and as additives for dried food formulations and smart packaging. While many studies have reported on the stability of anthocyanins in solution, there is limited information about their stability in the solid state, which is important for the aforementioned applications. Herein, we investigated the solid-state stability of a common anthocyanin, kuromanin chloride (KC), and its saccharide-free (aglycone) anthocyanidin derivative, cyanidin chloride (CC), under a range of storage conditions. Samples were analysed periodically via high-performance liquid chromatography (HPLC) to assess the percentage degradation. In the absence of light, KC and CC were found to be stable under atmospheric conditions at 22 °C (40 % relative humidity (RH)), but gradually degraded at elevated temperatures and humidity (e.g., 37 °C, 80 % RH) with a reduction by 30 % after 18 days. In contrast, KC and CC stored under argon or oxygen in the dark at 37 °C were completely stable. KC and CC exposed to white light at 22 °C displayed significant degradation after 18 d (∼40 and 60 %, respectively), regardless of whether exposed to the atmosphere, argon or oxygen. These results indicate that when stored in the solid state, anthocyanins are highly photosensitive and susceptible to hydrolytic degradation at elevated temperatures in the presence of moisture when stored in the dark. • The solid state-stability of anthocyanins was studied to inform storage conditions. • In the dark, anthocyanins were stable under standard atmospheric conditions. • Exposure to visible light under argon resulted in direct photochemical degradation. • Upon irradiation in the presence oxygen, photooxidative processes dominated. • Protection from light is critical for packaging and storage of anthocyanins. [ABSTRACT FROM AUTHOR]

Rosa rugosa is limited in landscaping applications due to its monotonous color, especially the lack of red-flowered varieties. Comprehensive assessment of petal color diversity in R. rugosa could promote to explore the mechanism of flower color formation. In this study, the variation and diversity of petal coloring of 193 R. rugosa germplasms were assessed by chromatic values (L∗ , a∗ , and b∗), and then divided into seven clusters belonging to three groups with pinkish-purple (185 individuals), white (6), and red (2) petals, respectively. Total anthocyanin content was the most important factor affecting flower color diversity and red hue formation of R. rugosa petals. There were significant correlations between petal color chromatic indexes and the sum content and the ratio of two major anthocyanin, namely cyanidin 3,5- O -diglucoside (Cy3G5G), peonidin 3,5- O -diglucoside (Pn3G5G). Both high levels of Cy3G5G + Pn3G5G and Cy3G5G/Pn3G5G were necessary conditions for red phenotype formation. Five cyanidin up-stream structural genes (RrF3′H1 , RrDFR1 , RrANS1 , RrUF3GT1 , RrUF35GT1) and one cyanidin down-stream structural gene (RrCCoAOMT1) were the key indicators which contributed to Cy3G5G + Pn3G5G and Cy3G5G/Pn3G5G, respectively. Functional verification showed that overexpression of RrDFR1 , combined with silent expression of RrCCoAOMT1 , could make R. rugosa petals redder by increasing the levels of Cy3G5G + Pn3G5G and Cy3G5G/Pn3G5G. These results provided a robust theoretical basis for further revealing the molecular mechanism of red petals coloration in R. rugosa. • Rosa rugosa germplasms were grouped into three groups based on chromatic values. • High levels of Cy3G5G + Pn3G5G and Cy3G5G/Pn3G5G are necessary for red color formation. • RrDFR1 and RrCCoAOMT1 are key genes for Cy3G5G + Pn3G5G and Cy3G5G/Pn3G5G respectively. • The co-expression of RrDFR1 and RrCCoAOMT1 resulted in red phenotype. [ABSTRACT FROM AUTHOR]

• The new LC-MS/MS strategy detects polyphenol metabolites in edible flowers. • The pseudo-targeted screening method enables accuracy and quantification. • Using the new strategy, 43 polyphenol metabolites were detected in 27 edible flowers. • Significant variations in polyphenol types and levels among the 27 flowers. • Enriched research on polyphenols in edible flowers;model applicable to other species. Edible flowers, as a food ingredient, are rich in bioactive substance and have received a lot of attention. In this study, we have established a pseudo-targeting method based on Multi Reaction Monitoring (MRM) - Enhanced Product Ions (EPI) in the Information Dependent Acquisition (IDA) mode. The results showed that a total of 43 metabolites, including flavonoids, phenolic acids, and terpenes were detected in 27 edible flowers using integrated liquid chromatography-tandem mass spectrometry (LC-MS/MS) strategy. Rutin was measured in all edible flowers, but the levels varied significantly among the different varieties of flowers, with the highest being about 3500 times the lowest. Albiflorin and paeoniflorin are polyphenolic substance unique to Paeonia suffruticosa. The cyanidin 3-O-glucoside chloride content in reddish-purple flowers is higher than that of other colors. Dicoumarin and 4-hydroxycoumarin were discovered in edible flowers for the first time. This study established a pseudo-targeted detection method to reveal the distribution of polyphenolic metabolites and enriched the research on polyphenolic metabolites in edible flowers. It can also serve as a general strategy to detect metabolites in other agricultural products, providing valuable information about potential metabolites for consumers. [ABSTRACT FROM AUTHOR]

Dendrobium officinale Kimura & Migo (D. officinale) has been widely used as Chinese medicine and functional food. In present study, the structural characteristics of anthocyanins in D. officinale were investigated by ultra-performance liquid chromatography with diode array detector (UPLC-DAD) and ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry (UPLC-Q-TOF-MS/MS). Totally, 14 anthocyanins were detected and identified, and 13 of them were first reported in D. officinale. Results showed that the vast majority of anthocyanins had multi-glycosylated cyanidin core, with variable acylation pattern mainly comprising phenolic acids. The composition and content of anthocyanins in D. officinale stems with different cultivation modes and years have been compared. The anthocyanins showed potent antioxidant activity in terms of radicals scavenging capacity and reducing power, as well as superior α-amylase and α-glucosidase inhibitory activity. The results provided a complete profile of anthocyanins in D. officinale and laid a foundation for further utilizing them as functional foods. [Display omitted] • 14 acylated anthocyanins (13 new) were detected in the Dendrobium officinale stems. • Their structure was elucidated by combining UPLC-DAD and UPLC-Q-TOF-MS/MS analysis. • The anthocyanin composition of different Dendrobium officinale stems was compared. • The anthocyanins showed excellent antioxidant and hypoglycemic activities. [ABSTRACT FROM AUTHOR]

[Display omitted] • Choline chloride: glycerol is a promising NADES for the extraction of anthocyanins from blackberry. • Ultrasound-assisted extraction is the most efficient compared to maceration and homogenization-assisted extraction techniques. • CHGLY extract provided high bioavailability of anthocyanins. • Two-aqueous phase method was successful for the purification of anthocyanins extracted in NADES. Natural deep eutectic solvents (NADESs) are a sustainable and green solution for the recovery of food ingredients such as pigments. In this work, the extraction conditions to obtain the maximum anthocyanins from blackberry fruit were investigated using NADES composed of choline chloride-acetic acid (CHAC) as the green solvent. The central composite design was used conseidering molar ratio, water content, solvent ratio and extraction time as independent variables and total anthocyanin content (TAC), cyanidin-3-glucoside, cyanidin-3-rutinoside, pelargonidin-3-glucoside and cyanidin chloride as responses. The results showed that the independent variables significantly affected the responses. The optimum conditions for CHAC were 1:3.5 M, 40 %, 30 g and 15 min for molar ratio, water content, solvent ratio and extraction time, respectively. Under these conditions, the experimental responses were 131.54 ± 7.89 mg CGE/100 g, 1208.08 ± 13.76 mg/kg, 163.43 ± 1.72 mg/kg, 53.78 ± 1.37 mg/kg and 91.98 ± 0.62 mg/kg for TAC, cyanidin-3-glucoside, cyanidin-3-rutinoside, pelargonidin-3-glucoside and cyanidin chloride, respectively. The pH, viscosity and electric conductivity of CHAC were determined as 1.24 ± 0.03, 1.21 ± 0.17 and 7.50 ± 0.55 mPa and 4675.33 ± 57.74 µS.cm−1, respectively. After storing the NADES extract for 28 days in the dark, cyanidin-3-glucoside, cyanidin-3-rutinoside, pelargonidin-3-glucoside and cyanidin chloride remained 71.57 ± 0.64 %, 75.00 ± 0.26 %, 33.42 ± 0.41 % and 71.45 ± 0.21 %, respectively. Over the 28-day exposure of the NADES extract to light, the cyanidin-3-glucoside, cyanidin-3-rutinoside, pelargonidin-3-glucoside and cyanidin chloride remained 19.09 ± 0.10 %, 34.89 ± 2.28, 13.28 ± 0.25 and 30.97 ± 1.10, respectively. The application of the aqueous two-phase system resulted in the preliminary purification of the NADES extract, providing the highest purity in the top phase for cyanidin-3-glucoside (68.85 ± 1.05 %). The findings revealed that CHAC is a promising green medium for the industrial extraction of anthocyanins, and the aqueous two-phase is suitable for the purification of the anthocyanin-rich extract obtained with NADES. [ABSTRACT FROM AUTHOR]

Insulin fibril formation decreases the effectiveness of insulin therapy and causes amyloidosis in diabetes. Studies suggest that phytochemicals are capable of inhibiting fibril formation. Herein, we investigated the inhibitory effects of anthocyanins, including cyanidin, cyanidin-3-glucoside (C3G), cyanidin-3-rutinoside (C3R), malvidin, and malvidin-3-glucoside (M3G) on fibril formation. Our results revealed that anthocyanins (50–200 μM) significantly reduced the formation of insulin fibrils by increasing lag times and decreasing ThT fluorescence at the plateau phase. These findings were confirmed by TEM images, which showed reduced fibril length and number. Furthermore, FTIR analysis indicated that anthocyanins reduced the secondary structure transition of insulin from α-helix to β-sheet. Anthocyanins interacted with monomeric insulin (residues B8–B30) via H-bonds, van der Waals, and hydrophobic interactions, covering the fibril-prone segments of insulin (residues B12–B17). Based on the structure-activity analysis, the presence of glycosides and hydroxyl groups on phenyl rings increased intermolecular interaction, mediating the inhibitory effect of anthocyanins on fibril formation in the order of malvidin < cyanidin < M3G < C3G < C3R. Moreover, anthocyanins formed H-bonds with preformed insulin fibrils, except for malvidin. In preadipocytes, C3R, C3G, and cyanidin attenuated insulin fibril-induced cytotoxicity. In conclusion, anthocyanins are effective inhibitors of insulin fibril formation and cytotoxicity. • Anthocyanins inhibit insulin fibrillation in vitro. • Anthocyanins significantly extend the lag time of insulin fibril formation. • All anthocyanins share the same interacting site at Val12 of insulin B-chain. • The inhibitory effect is due to H-bond formation between insulin and anthocyanins. • Anthocyanins decrease insulin fibril-induced cytotoxicity in 3T3-L1 preadipocytes. [ABSTRACT FROM AUTHOR]

• Anthocyanins in China aster of different colours were analyzed qualitatively and quantitatively for the first time. • 2. Genotype 'Arka violet Cushion' was the richest source of anthocyanins (469.36 mg/100 g FW), with delphinidin and cyanidin as major compounds. • Anthocyanin content of Arka violet cushion was 2–3 times that of Clitorea ternatea, Centaurea cyanus and hibiscus rosa-sinensis, which can be exploited commercially for bio-color synthesis. Anthocyanins are biocolorants which have gained momentum owing to their extensive range of colors and antioxidant activity which has great potential in food, pharmaceutical, textile and cosmetic industries. China aster became popular among the consumers due to its myriad colors. To find out the pigment composition responsible for flower color, fifteen genotypes of China aster were studied using liquid chromatography- mass spectrometry (LC-MS/MS). The flower color analysis indicated that the 15 genotypes of China aster grouped into seven groups viz., red purple, red, purple, purple violet, violet, white and yellow. Flower petals were evaluated for color through Royal Horticultural Society Color Chart (RHSCC) and calorimeter that resulted in most of the genotypes were categorized under red purple group. The flower color in China aster is due to the presence of three primary anthocyanidins namely cyanidin, pelargonidin and delphinidin. A total of 4 anthocyanins namely cyanidin, pelargonidin, delphinidin and malvidin were identified and quantified. The genotype Arka Violet Cushion was the richest source of anthocyanins (469.36 mg/100 g FW) and IIHRJ22, the poorest (1.17 mg/100 g FW). Genotype Arka Violet Cushion recorded highest for both the cyanidin and delphinidin, however, pelargonidin was recorded highest in Matsumoto Red. The genotype Arka Violet Cushion has been identified with highest anthocyanin can be exploited commercially for bio-color synthesis. The trend of decreased L* value of Color Reader with increased total anthocyanin content was observed in red purple and purple group. The correlation between L* value and total anthocyanin content was not observed in white and violet group. The results revealed that the white and yellow group has very low anthocyanin content which indicates the presence of co-pigmentation in China aster. Arka Violet Cushion recorded 2–3 times higher anthocyanin content than the commercial sources viz., Clitorea ternatea, Centaurea cyanus and Hibiscus rosa-sinensis , which can be exploited commercially for bio color synthesis. [ABSTRACT FROM AUTHOR]

The occurring of glycation reaction and protein-protein interaction in the energy appetizers caused browning and hardness instability while storing these appetizers, leading to the loss of consumer acceptability. Amassing among anthocyanins and proteins could mitigate the appetizers' instability. We, therefore, investigated the anti-aggregation and ant-glycoxidation impacts of mulberry anthocyanins combined with ultrasonic treatment (UT) pre-texturization in an energy appetizer model throughout storage via multi-dimensional methods, containing UPLC-ESI-MS/MS, SDS-PAGE, FTIR, texture analyser, and a molecular docking analysis. Results noted that UT-anthocyanins significantly downgraded the browning progress, advanced glycation end-products, and/or N-(carboxymethyl)- l -lysine intensities of energy appetizers after 45 d of storage at 45 °C. UT-anthocyanins also relegated the protein insolubility, accumulation, oligomerization, and glycoxidation throughout the late storage. A molecular docking analysis evidenced that cyanidin 3- O -glucoside and cyanidin 3- O -rutinoside networked with β-lactoglobulin subunits via H-bonding and π-π forces. This binding hindered some glycoxidation residues of β-lactoglobulin the lysyl residues. Finally, these findings recommended that the UT-anthocyanins could be employed as an encouraging antiglycative approach to alleviate AGEs-creation and other consequent undesirable fluctuations in protein-rich food patterns, thereby enhancing the energy appetizer's post-processing stability during storage. [Display omitted] • UT-anthocyanins mitigated the hardening of energy appetizers. • UT-anthocyanins showed anti-browning effects during store the energy appetizers. • The binding between anthocyanins and proteins enhanced the energy appetizers stability. • The pre-texturization of proteins by ultrasonic also enhanced the energy appetizers stability. [ABSTRACT FROM AUTHOR]

• The yellow color of Mint was mainly affected by the conversion of dihydroquercetin to quercetin by the effect of FLS, and the PH, iron ions and CCD1 could also affect its flower color. • The red color of Mpun was mainly presented by the glycosylation of cyanidin and cyanidin, and copper ions, ZDS, and CCD1 could also affect its flower color. • The blue flower color of Mwil was resulted by the glycosylation of cyanidin, iron ion, oxidation, phosphate ion and other factors. Meconopsis (Meconopsis spp.) belongs to the family Papaveraceae and is the representative alpine flora in the Pan Himalaya region. Diversity in color is a key taxonomic feature of Meconopsis species, which makes it to be an ideal material for mechanism analysis of petals coloration; however, few studies have focused on this topic. In this study, we selected three Meconopsis species with different flower colors, including M. punicea with red flowers, Meconpsis integrifolia with yellow-green mix flowers, and M. wilsonnii with blue-violet mix flowers. To reveal the coloration mechanisms in Meconopsis , petal samples were collected from each species at three developmental time points (initial, middle, and mature) for RNA sequencing and identification of anthocyanins and flavonoids. Our results showed that the mechanisms of petal coloration were different in selected species, and cyanidin and flavonols were the main factors affecting their coloration. The yellow-green mix petal of M. integrifolia was mainly presented by flavonols and chlorophyll, the red petal of M. punicea was presented by cyanidin, and the blue-violet mix petal of M. wilsonnii was mainly composed of a complex formed by cyanidin and other substances. Some stress resistances were also found in these three species. M. integrifolia could better maintain the stability of the transition metal ions in cells, and M. punicea showed a better ability on the defense to bacteria and dryness. Both the flowers of M. integrifolia and M. wilsonnii could better remove superoxide. Our analysis revealed the coloration mechanisms in three Meconopsis species and provided precious genetic resources for further analysis. [ABSTRACT FROM AUTHOR]

Acer rubrum L. is one of the most prevalent ornamental species of the genus Acer, due to its straight and tall stems and beautiful leaf colors. For this study, the Oxford Nanopore platform and Hi-C technology were employed to obtain a chromosome-scale genome for A. rubrum. The genome size of A. rubrum was 1.69 Gb with an N50 of 549.44 Kb, and a total of 39 pseudochromosomes were generated with a 99.61% genome. The A. rubrum genome was predicted to have 64644 genes, of which 97.34% were functionally annotated. Genome annotation identified 67.14% as the transposable element (TE) repeat sequence, with long terminal repeats (LTR) being the richest (55.68%). Genome evolution analysis indicated that A. rubrum diverged from A. yangbiense ∼6.34 million years ago. We identified 13 genes related to pigment synthesis in A. rubrum leaves, where the expressions of four ArF3′H genes were consistent with the synthesis of cyanidin (a key pigment) in red leaves. Correlation analysis verified that the pigmentation of A. rubrum leaves was under the coordinated regulation of non-structural carbohydrates and hormones. The genomic sequence of A. rubrum will facilitate genomic breeding research for this species, while providing the valuable utilization of Aceraceae resources. • The chromosome-scale genome of A. rubrum was obtained. • An advance in the determination of complex genomes in polyploid plants. • Regulatory among pigments, hormones, and carbohydrates in A. rubrum leaves. [ABSTRACT FROM AUTHOR]

Consumption of high fat diets (HFD) mimics a modern or "Western style" diet pattern and can impair intestinal barrier integrity, leading to endotoxemia and associated unhealthy conditions. This study investigated if supplementation with an anthocyanin (cyanidin and delphinidin glucosides)-rich extract (CDRE) could revert or mitigate HFD-induced alterations of colonic physiology in part through the regulation of Toll-Like Receptor 4 (TLR-4)- and redox-regulated signaling. C57BL/6J male mice were fed for 4 weeks with a control or an HFD. Then, mice were divided in four groups fed either control or HFD, or these diets supplemented with CDRE for the subsequent 4 weeks. After 8 weeks on the HFD we observed in the colon: i) disruption of tight junction structure and function; ii) increased TLR-4 expression; iii) increased NADPH oxidase NOX1 expression, and iv) activation of redox-sensitive and TLR-4-triggered pathways, i.e. NF-κB, ERK1/2, JNK1/2, PI3K/Akt. All these events were prevented or reverted by CDRE supplementation. Supporting the relevance of CDRE-mediated downregulation of TLR-4 on its colon beneficial effect; in vitro (Caco-2 cell monolayers), cyanidin, delphinidin and their metabolites protocatechuic and gallic acid, mitigated lipopolysaccharide (LPS)-induced monolayer permeabilization by restoring tight junction structure and dynamics and preventing lipid/protein oxidation. The CDRE also mitigated HFD-mediated alterations in parameters of goblet cell differentiation and function, including the downregulation of markers of goblet cell differentiation (Klf4), and intestinal mucosa healing (Tff3). Results show that a short-term supplementation with cyanidin and delphinidin, protect from HFD-induced alterations in colon physiology in part through the modulation of TLR-4- and redox-regulated signaling. [Display omitted] • Anthocyanins mitigate high fat diet-induced alteration in colonic physiology. • Cyanidin and delphinidin mitigate high fat diet/LPS-induced barrier integrity loss. • Anthocyanins actions are in part mediated by redox-regulated mechanisms. • Anthocyanins actions are in part mediated by TLR-4-regulated mechanisms. [ABSTRACT FROM AUTHOR]

• 16 h day/8 h dark can significantly shorten the maturity period in pepper. • Color in fruit skin is the combined result of various species from anthocyanins and carotenods. • Anthocyanin synthesis did not cease, and its degradation and accumulation of carotenoids proceeded simultaneously as the fruits matured. The need for a lengthy maturation period and delayed changes in color are the key factors that reduce the market value of hot peppers (Capsicum annuum L.). This study assessed the effects of different photoperiods on the reduction of the maturation period and changes in color of hot peppers. The use of a photoperiod of 16 h day/8 h night (the T4 group) resulted in a higher percentage of red hot peppers, earlier seed maturity and shorter days for the hot peppers to mature compared to the control. This suggests that the T4 group reduced the period of hot pepper maturity. An additional analysis found that the promotion of the process of changes in the color and the formation of red color in the fruits that is owing to the T4 group is the result of a combination of α-carotene, β-carotene, γ-carotene, and capsorubin. In addition, anthocyanins, including delphinidin, malvidin, and cyanidin, played a key role in the formation of purple in the hot peppers, and these pigments were related to some key differentially expressed genes. Interestingly, the biosynthesis of anthocyanins did not stop as the hot peppers matured, and the degradation and accumulation of the carotenoids proceeded simultaneously. The T4 treatment inhibited the degradation of anthocyanins, which indicated that the color of the hot peppers is owing to a mixture of anthocyanins and carotenoids. This study provides insight into the mechanism of pigment biosynthesis and the potential use of photoperiods in the process of speed breeding peppers. [ABSTRACT FROM AUTHOR]

• Anthocyanin determined sepal color in Aquilegia oxysepala. • Flavones determined sepal color in Aquilegia oxysepala f. pallidiflora. • Transcriptome identified anthocyanin biosynthesis structural genes. • Broad-target metabolome revealed secondary substances profiles. • Integration analysis predicted key regulatory networks and transcription factors. Aquilegia oxysepala is a perennial native to northeast China with widespread practical uses and exhibiting dark red sepals. A. oxysepala f. pallidiflora is a natural variant of A. oxysepala with pale yellow sepals. To reveal the regulatory mechanisms involved in sepal color evolution, sepals of two Aquilegia species were subjected to transcriptome and broad-target metabolome analyses. Key regulatory networks were predicted to correlate with the anthocyanin biosynthesis pathway, based on co-joint and weighted gene co-expression network analyses. In total of 9000 differentially expressed genes and 1159 metabolites were identified. Using Kyoto Encyclopedia of Genes and Genomes enrichment analysis, 15 structural genes and 8 anthocyanins were annotated in the pathways of anthocyanin biosynthesis. Anthocyanins were detected in both A. oxysepala species. Cyanidin and delphinidin glucoside were the main substances that determined sepal color in A. oxysepala , and apigenin glucoside was the main respective compound in A. oxysepala f. pallidiflora. Compared with A. oxysepala, A. oxysepala f. pallidiflora exhibited downregulation of anthocyanin biosynthesis and transport genes. ERF, bHLH, B3, C2H2, HB_PHD, Trihelix, WRKY, MYB, NAC, Whirly, and M-type_MADS played key roles in anthocyanin biosynthesis. This study elucidated the molecular characteristics of color variation in A. oxysepala , providing new insights into adaptive evolution of Aquilegia and a theoretical basis for innovative breeding of Aquilegia. [ABSTRACT FROM AUTHOR]

• Disruption of IL-17A interaction with IL-17RA restored efferocytosis in an adjuvant model of RA. • IL-17A suppressed efferocytosis via ADAM17 mediated cleavage of MERTK. • IL-17A driven defective efferocytosis was also dependent on drp-1 mediated mitochondrial fission. • Inhibition of IL-17A binding to IL-17RA sensitized macrophages to immunosuppressive PD-L1 signaling. • Molecular switching of STAT-3 to STAT-5 activation abrogates negative impact of IL-17A signaling on efferocytosis. Defective clearance of apoptotic cells due to impaired efferocytosis sustains error in self-tolerance that exacerbates rheumatoid arthritis (RA). However, the molecular determinant that directly or specifically impairs efferocytosis in RA is not yet studied. We identified a new perspective that IL-17A significantly impedes efferocytosis via preferential activation of the JAK/STAT-3/ADAM17 signaling axis. In contrast, disruption of the IL-17A/IL-17RA interaction using cyanidin or silencing of IL-17RA obstructed JAK/STAT-3 activation that further abolished ADAM17 expression. Subsequent depletion of ADAM17 inhibited the shedding of Mer tyrosine kinase receptor (MERTK), which significantly increased apoptotic cell intake and restored efferocytosis in adjuvant-induced arthritic (AA) model. Concomitantly, the amplification of the efferocytosis process due to IL-17A/IL-17RA interaction disruption was sensitive to mitochondrial fission mediated via Drp-1 phosphorylation downstream of STAT-3 inhibition. As expected, cyanidin treated AA synovial macrophages that exhibited increased efferocytosis demonstrated a phenotypic shift towards CD163 anti-inflammatory phenotype in a STAT-5 dependent manner. Similar results were obtained in IL-17A-sensitized AA synovial macrophages treated with S3I-201 (a STAT-3 inhibitor) indicating that IL-17A influences efferocytosis via the STAT-3 pathway. In view of our previous work where cyanidin restored Th17/Treg balance, our present investigation fulfils a critical gap by providing scientific validation that cyanidin escalated PD-L1 expression during the efferocytosis process that could have impacted the restoration of Th17/Treg balance in an AA model. Together, these data corroborate the hypothesis that IL-17A signaling can impair efferocytosis via regulating STAT-3/ADAM17/FL-MERTK axis and that its inhibition can amplify a pro-resolution signal against RA progression. [ABSTRACT FROM AUTHOR]

• Chiral CNC-cyanidin films with multiple stimulus responses for freshness monitoring. • CNC and cyanidins are ecologically-friendly natural substances with no toxicity. • The samples with enhanced strength exhibit good flexibility under bended states. • CNC-cyanidin films displayed significant color variation over the pH range of 2–13. • The sample could be a convenient and visual diagnostic freshness monitor in real-time. Biobased multi-stimulation materials have received considerable attention for intelligent packaging and anti-counterfeiting applications. Cellulose nanocrystals (CNCs) and cyanidins are good material candidates for monitoring food freshness as they are eco-friendly natural substances. This work incorporated cyanidin with a CNC-hosting substrate to develop a simple, environment-friendly colorimetric device to visualize food freshness. Across the pH range of 2–13, the indicator exhibited noticeable color changes ranging from red to gray and eventually to orange. The CNC-cyanidin (CC) film exhibited a dramatic color change from blue to dark red and high sensitivity at a relative humidity of 30 %–100 %. In corresponding to the total volatile elemental nitrogen (TVB-N) level of shrimp, the indicator showed distinguishable colors at different stages of shrimp. The findings imply that the samples have substantial potential for use as an intelligent indicator for tracking shrimp freshness. [ABSTRACT FROM AUTHOR]

The present study investigated water-soluble pectin (WSP), chelating pectin (CSP), sodium carbonate-soluble pectin (NSP), and cyanidin-3- O -glucoside (C3G). Various ultrasonic treatments (688, 1376, 2064, 2431, and 3437 W/cm2, 10 min) were used to modify the three types of pectin, and the structural changes in pectin and the interaction mechanisms between pectin and cyanidin were analysed. The experimental results indicated that ultrasonic (US) modification reduced the molecular weight and degree of methylation (DE) of pectin. The DE values of WSP and CSP decreased by 24.51% and 80.12%, respectively. US modification disrupted the branched structure of pectin and reduces the ratio of rhamnose/galacturonic acid, which caused an increase in the linearity of pectin. US modification enhanced the interaction between the three pectins and anthocyanins, and the US condition of 2064 W/cm2 for 10 min increased the binding rate by 15.71%–46.18%. NSP had the largest binding rate, and US modification had the greatest improvement in WSP binding rate. After US modification, the particle size of the pectin-cyanidin complex decreased, and the zeta potential increased. After heat treatment, the residual mass percentage of the pectin-C3G complex increased, which suggested that the encapsulation of C3G in pectin improved thermal stability. Therefore, US treatment is a versatile processing tool that reduces the DE of pectin and enhances its linearity, which offers a promising approach to promoting pectin-C3G complexes. [Display omitted] • Ultrasound improved pectin linearity, reduced its molecular weight and methylation. • Ultrasonic modified pectin enhanced its binding ability with cyanidin. • Alkali-soluble pectin had the strongest binding ability for cyanidin. • Binding ability of ultrasonic modified water-soluble pectin was increased the most. • Low methylation and high linearity modification improved pectin binding ability. [ABSTRACT FROM AUTHOR]

[Display omitted] • Freeze-drying increases the extraction rate of anthocyanins from Lycium ruthenicum. • Different drying pretreatment affects anthocyanin composition and concentration. • Ultrasonic-assisted enzymatic extraction of anthocyanins can reach 3.16 g/100 g. • Pretreatments had less effect on the types of anthocyanins, but more on the content. Extraction of anthocyanins from Lycium ruthenicum Murr. (L. ruthenicum) is a notable challenge in food production, requiring methods that balance efficiency and safety. In this study, we conducted a comparative analysis the extraction of anthocyanins by natural air drying (NAD), vacuum freeze drying (VFD), hot air drying (HAD), and vacuum microwave drying (MVD) combined with ultrasonic-assisted enzymolysis extraction (UAEE). The results demonstrated that the extraction yield and antioxidant activity of anthocyanins were significantly higher in VFD. This phenomenon can be attributed to the modification of raw material's microstructure, leading to an increased extraction yield of specific anthocyanins such as Cyanidin-3-galactoside, Delphinidin chloride, Cyanidin, and Petunidin. According to the pretreatment results, the extraction process of anthocyanins was further optimized. The highest yield (3.16 g/100 g) was obtained in following conditions: 0.24 % pectinase, 48 °C, solid:liquid = 1:21, and 21 min ultrasonic time. This study improves the commercial value and potential application of L. ruthenicum in food industry. [ABSTRACT FROM AUTHOR]

[Display omitted] • A methodology combining HPLC-CADD was established to investigate the regulatory effects of food on hepatic glycemic metabolism. • The main components of Chongqing Tuocha, were identified for the first time. These components include catechins, phenolic acids, and flavonols, and a lower amount of anthocyanins. • Our exploration identified Caffeic acid, Pelargonidin, and Cyanidin as potential regulators of liver glucose. We investigated and visualized their mechanisms of action utilizing molecular dynamics simulations. • The constituents identified in Chongqing Tuocha can ultimately influence the expression of the insulin receptor IRS-1 and the glucose receptor GLUT-2 in hepatocytes through FXR/FGF/19, Keap1-Nrf2/OH-1/SOD, and PPAR-α/UCP-2. Chongqing Tuocha (CT) is a regional specialty of southwest China, traditionally believed to have properties that regulate blood sugar levels, although its precise mechanism remains elusive. Our research employed methodologies including HPLC, molecular docking, molecular dynamics simulation, circular dichroism spectrum (CD) and cell experiments to investigate the active compounds and underlying mechanisms of CT in liver glucose metabolism. The findings highlight catechins as the predominant compounds in CT, accompanied by flavonols, glycosides, phenolic acids, and a minor quantity of anthocyanins. Autodock analysis identifies caffeic acid, pelargonin, and cyanidin as showing the highest potential for hypoglycemic effects. Molecular dynamics simulation and CD illustrate intricate binding interactions of small molecular ligands. Cell studies verify the significant impact of these distinctive compounds on downstream proteins associated with critical hypoglycemic pathways. This research elucidates the active compounds and potential mechanisms of CT in managing hypoglycemia, laying the groundwork for forthcoming animal trials and guiding therapeutic interventions. [ABSTRACT FROM AUTHOR]

Environmentally-friendly, cyanidin(Cy)-based anthocyanin isolated from red-cabbage served as a spectroscopic probe imprinted onto chitosan nanoparticles (CsNPs), which were in turn integrated onto cellulose paper strip (CPS) as a host matrix to develop a metallochromic solid state sensor for real-time selective determination of ferric ions in an aqueous medium. The ferric transition metal ions in aqueous environments were detected using a novel, simple, portable, fast responsive, low-cost, real-time, environmentally safe, reversible and colorimetric sensor based on chitosan nanoparticles as a hosting biopolymer and cyanidin phenol chromophore as a biomolecular probe. In order to use the cyanidin biomolecule as a pH indicator and chelating agent, it was purified from red-cabbage and added into the CsNPs biosensor film. The colorimetric shift increased in direct proportion to the ferric ion concentration. As a result, the current research that was both qualitative and quantitative was carried out. While the Cy-CsNPs-CPS sensor showed high selectivity for ferric ions, no color change was detected for other metal cations. It was discovered that the detection process occurred as a result of a coordination complex formed between the active sites of phenolic cyanidin and Fe(III) ions. • Cyanidin extract from red-cabbage was imprinted into nanochitosan. • Cyanidin-nanochitosan was immobilized onto cellulose paper strips by dip-coating. • Sensor strip showed colorimetric sensitivity and selectivity to FeCl 3(aq). • Color shifted from white to pink upon immersion in FeCl 3(aq). • The detection limit was monitored in the concentration range of 10–400 mg/L. [ABSTRACT FROM AUTHOR]

Anthocyanin rich colored wheat with additional health benefits has created interest among breeders, consumers and policy makers to address the prevailing malnutrition in the vulnerable population. Researchers are exploring how colored wheat could perform under different nutrient conditions for the maintenance of growth and development. The present study was aimed to investigate the differential response of phosphorous (Pi) deficiency at the seedling stage using hydroponics. Our results showed that Pi-deficiency triggered typical response in the wheat along with the changes in the plant root morphology, total biomass, micronutrient concentration and distinct anthocyanin accumulation. Our physiological and biochemical data revealed that these parameters were positively altered under stress in the colored wheat and the adaptation followed the trend of white < blue

As a category of natural colourants, anthocyanins are abundant in purple-fleshed sweet potato (PFSP). Recently, anthocyanins from PFSP are proven to have multiple bioactivities, but they are liable to undergo discolouration and degradation upon thermal treatment, light exposure, oxidation, etc. Thus, the destabilisation/stabilisation of PFSP anthocyanins has received extensive attention from both academic and industrial views. This work aims to present an updated overview of the occurrence, destabilisation, and stabilisation of anthocyanins in purple-fleshed sweet potato varieties. In total, forty-two anthocyanin monomers are found in PFSP, and they belong to the glycosylated and acylated derivatives of cyanidin, peonidin, pelargonidin, and delphinidin, with the first two predominating. Notably, PFSP anthocyanins were susceptible to destabilisation (degradation/discolouration) when exposed to acid/alkaline, heat, light, oxygen, ascorbic acid, sulfite, metal ions, and enzymes. Herein, the destabilising mechanism, the loss in food processing and the structure-stability relationship of PFSP anthocyanins were deeply discussed. More importantly, it was of high industrial significance that PFSP anthocyanins could be stabilised or protected by intramolecular or intermolecular copigmentation, encapsulation, and certain protective agents. Intramolecular copigmentation often occurred in acylated anthocyanin molecules, while phenolic acids, metal ions, polysaccharides, and proteins could serve as copigments in intermolecular copigmentation. When embedded in polysaccharide-based microcapsules and hydrogels, trapped in β -cyclodextrin cavities, and loaded in surfactant micelles, PFSP anthocyanins demonstrated enhanced stability. In addition, the replacement of ascorbic acid with its derivatives and the applications of antioxidants and enzyme inhibitors favoured the stabilisation of PFSP anthocyanins. - Anthocyanin is a valuable food ingredient but susceptible to destabilisation. - Purple-fleshed sweet potato (PFSP) is one of popular foods rich in anthocyanins. - Cyanidin and peonidin are the major aglycones in constituting PFSP anthocyanins. - PFSP anthocyanins are sensitive to pH, heat, light, oxygen, ascorbic acid, etc. - Copigmentation, encapsulation and protective agents could stabilise PFSP anthocyanins. [ABSTRACT FROM AUTHOR]

Anthocyanins are a group of natural water-soluble pigments in plants that contribute to the pink-purple color of a range of tissues. Because anthocyanins have various biological activities in human health, there is great research interest in the development of anthocyanin-rich foods and beverages, including purple shoot tea. Anthocyanidin 3- O -galactosides have been identified as one of the main anthocyanin components in purple shoot tea, but the enzyme responsible for their biosynthesis remains unclear. UDP-galactose anthocyanidin 3- O -galactosyltransferase (UA3GalT) is presumed to catalyze the galactosylation of anthocyanidin. Therefore, we assayed the UA3GalT activity in five tea samples with varying degrees of purple color and found that its activity was strongly positively correlated (r = 0.929, p < 0.05) with anthocyanin content. Phylogenetic analysis and sequence alignment suggested that CsUGT78A15 encoded a UA3GalT enzyme. Enzymatic assays indicated that r Cs UGT78A15 could catalyze the synthesis of cyanidin 3- O -galactoside and delphinidin 3- O -galactoside using UDP-galactose as a sugar donor, and it showed higher catalytic efficiency towards delphinidin than cyanidin. These results indicate that Cs UGT78A15 acts as a UA3GalT in vitro. Subcellular localization showed that Cs UGT78A15 was located in the endoplasmic reticulum (ER) and nucleus, consistent with the location of anthocyanin synthesis. Transient overexpression of CsUGT78A15 in the fruit of mature 'Granny Smith' apples showed that the upregulation of CsUGT78A15 promoted cyanidin 3- O -galactoside accumulation in apple skins. These results suggested that Cs UGT78A15 could catalyze galactosylation of anthocyanidins in planta. Our findings provide insight into the biosynthesis of anthocyanins in tea plants. • The UA3GalT activity was positively correlated (r=0.929, p <0.05) with anthocyanin content. • rCsUGT78A15 could catalyze the synthesis of cyanidin 3- O -galactoside and delphinidin 3- O -galactoside • Transient overexpression of CsUGT78A15 promoted the accumulation of anthocyanins in the fruit of 'Granny Smith' apples. [ABSTRACT FROM AUTHOR]

[Display omitted] • Purification of individual anthocyanins from black carrots. • Higher stability of non-acylated anthocyanins than acylated anthocyanins when exposed to light. • Acylated anthocyanins was found to undergo cleavage of the glycosidic bond. Black carrot anthocyanins have gained increasing attention as natural coloring agent, owing to their higher stability than anthocyanins from berries. The stability has been attributed to their higher degree of acylation. This study investigated the impact of acylation on the stability of individual anthocyanins during storage in light and darkness. We hypothesized that the acylated anthocyanins would be more stable than the non-acylated ones. The major five anthocyanins were fractioned by semi-preparative HPLC and stored at pH 4.5 in light and darkness to investigate how acylation affected the stability. The stability was evaluated by absorption spectroscopy and mass spectrometry (MS). Two of the anthocyanins were non-acylated; 3-xylosyl(glucosyl)galactoside and cyanidin 3-xylosylgalactoside, and three were acylated; cyanidin 3-xylosyl(sinapolyglucosyl)galacto-side, cyanidin 3-xylosyl(feruloylglu-cosyl)galactoside, and cyanidin 3-xylosyl(coumaroyl-glucosyl)galactoside. Both methods (spectroscopy and MS) showed a clear effect of acylation when stored in light, but surprisingly the two non-acylated anthocyanins, showed higher stability than the three acylated ones. [ABSTRACT FROM AUTHOR]

[Display omitted] • Double emulsion gels were based on nanoemulsions and Pickering particles. • Hydrophobic quercetin and hydrophilic cyanidin were co-encapsulated. • In-situ hydrophobicity of Pickering particles was weakened by Tween-80. • pH-chromic 3D printing was performed using the pH sensitivity of cyanidin. • Double emulsion gels could co-deliver quercetin/cyanidin in simulated digestion. An O1/W/O2 double emulsion gel, as a functional fat substitute and based on nanoemulsions and hydrophobic Pickering particles, is prepared by two-step emulsification to co-encapsulate hydrophilic cyanidin and hydrophobic quercetin. Nanoemulsions loading quercetin are fabricated by Tween-80 and combining high-speed and high-pressure emulsification. Phytosterol nanoparticles stabilize the W-O2 interface of the secondary emulsion to load cyanidin in the W phase. The concentration of Tween-80 is optimized as 0.3% by the droplet size and viscosity of nanoemulsions. The structural stability of double emulsion gels will be weakened along with the increase of nanoemulsions, showing lower modulus and encapsulation efficiency (EE) and bigger droplets. In double emulsion gels, the EE of quercetin and cyanidin reaches 93% and 85.6%, respectively. Analysis of molecular interaction indicates that Tween-80 would decrease the in-situ hydrophobicity of phytosterol nanoparticles by hydrogen bonding adsorption, thereby weakening the emulsification. The pH-chromic 3D printing of double emulsion gels is designed according to the pH sensitivity of cyanidin. Texture profile analysis is performed to test the textural properties of 3D-printed objects. The simulated digestion is conducted on double emulsion gels. The double emulsion gel with fewer nanoemulsions is beneficial for protecting quercetin and improving the delivery due to the higher structural stability, while that with more nanoemulsions is conducive to the digestion of cyanidin and camellia oil due to weakened semi-solid properties. This double emulsion gel further simulates fat tissues by co-encapsulating hydrophilic and hydrophobic substances, promoting the application of fat substitutes in the food industry. [ABSTRACT FROM AUTHOR]

[Display omitted] High-fat diet (HFD) consumption and excess nutrient availability can cause alterations in mitochondrial function and dynamics. We previously showed that anthocyanins (AC) decreased HFD-induced body weight gain and fat deposition. This study investigated: i) the capacity of AC to mitigate HFD-induced alterations in mitochondrial dynamics, biogenesis, and thermogenesis in mouse subcutaneous white adipose tissue (sWAT), and ii) the underlying mechanisms of action of cyanidin-3- O -glucoside (C3G), delphinidin-3- O -glucoside (D3G), and their gut metabolites on mitochondria function/dynamics in 3T3-L1 adipocytes treated with palmitate. Mice were fed control or HFD diets, added or not with 40 mg AC/kg body weight (BW). Compared to control and AC-supplemented mice, HFD-fed mice had fewer sWAT mitochondria that presented alterations of their architecture. AC supplementation prevented HFD-induced decrease of proteins involved in mitochondria biogenesis (PPARγ, PRDM16 and PGC-1α), and thermogenesis (UCP-1), and decreased AMPK phosphorylation. AC supplementation also restored the alterations in sWAT mitochondrial dynamics (Drp-1, OPA1, MNF-2, and Fis-1) and mitophagy (BNIP3L/NIX) caused by HFD consumption. In mature 3T3-L1, C3G, D3G, and their metabolites protocatechuic acid (PCA), 4-hydroxybenzaldehyde (HB), and gallic acid (GA) differentially affected palmitate-mediated decreased cAMP, PKA, AMPK, and SIRT-1 signaling pathways. C3G, D3G, and metabolites also prevented palmitate-mediated decreased expression of PPARγ, PRDM16, PGC-1α, and UCP1. Results suggest that consumption of select AC, i.e. cyanidin and delphinidin, could promote sWAT mitochondriogenesis and improve mitochondria dynamics in the context of HFD/obesity-induced dysmetabolism in part by regulating PKA, AMPK, and SIRT-1 signaling pathways. [ABSTRACT FROM AUTHOR]

Roses are woody perennial flowering plants cultivated worldwide for several ornamental, cosmetic, and medicinal purposes. Rose flowers are rich in anthocyanins including cyanidin, peonidin, and its derivatives. In this study natural deep eutectic solvent (NADES)-based ultrasound-assisted extraction of anthocyanins was carried out from fresh and dried rose flowers. A total of 12 NADES were prepared based on combinations of organic acid derivatives, mixture of sugars, and choline chloride derivatives for extraction. Conventional solvent-acidified methanol (80 % v/v) was also used as a control to compare the efficiency of solvent systems. Total anthocyanin content was higher in dried rose flower extracts. When using sugar and organic acid-based systems, the highest anthocyanin content was observed in extracts of NADES composed of glucose: citric acid (1:1) (636 ± 26.64 mg/L) and glucose: lactic acid (1:1) (564.73 ± 14 mg/L) based systems. Amongst, the choline chloride derivatives-based solvent systems, highest anthocyanin content (826.59 ± 17.35 mg/L) was observed in a combination of lactic acid-choline chloride (1:1) based system. The anthocyanins extracted in sugar-based NADES systems showed better thermal stability at higher temperatures and when stored at 4 ℃ and −20 ℃. NADES-based extracts (N8) from dried rose flowers also showed higher antioxidant capacity as per DPPH scavenging activity (IC 50 value: 0.0021 ± 0.007 mg/ml) and was in correlation with anthocyanin contents. HPLC analysis of NADES-based and control extracts revealed the presence of cyanidin chloride. The outcome of the study showed efficient ultrasound-assisted extraction of anthocyanins from rose flowers using lactic acid: choline chloride (1:1) and lactic acid: glucose (1:1) based NADES systems. • Natural Deep Eutectic Solvent (NADES)-based extraction of rose anthocyanins • Highest anthocyanin content was in lactic acid and choline chloride based NADES • Cyanidin chloride was detected in NADES-based anthocyanin floral extracts. [ABSTRACT FROM AUTHOR]

Rosa pimpinellifolia L. fruits (RPF) have great industrial potential due to the high presence of anthocyanins. In this work, microwave-assisted aqueous two-phase extraction (MA-ATPE) was applied to simultaneous extraction and purification of anthocyanins from RPF with ethanol/ammonium sulfate aqueous two-phase system (ATPS). MA-ATPE process was optimized by single-factor experiments and response surface methodology. The optimal anthocyanin yields were achieved in conditions of 0% HCl (w:w), 26.85% ethanol (w:w), 19.15% ammonium sulfate (w:w), liquid to solid ratio 40, 17.29 min, 60 °C and 400 W. Predicted anthocyanin yield of MA-ATPE at optimum conditions were determined as 1373.04 mg cyanidin 3-glucoside equivalent/g dry RPF. The purity of anthocyanin rich extract obtained by MA-ATPE was 1.65-fold greater than microwave assisted extraction using 80% ethanol (MAE). The compositional characterization of anthocyanins were carried out with HPLC-QTOF-MS. MA-ATPE had no obvious changes on anthocyanin composition when compared to MAE. Results indicated that the MA-ATPE could be a promising method for the extraction and preliminary purification of anthocyanins from different plant materials. [ABSTRACT FROM AUTHOR]

Findings small molecules with protein disaggregation effects are lately needed. For the first time, we studied the in vitro -antifibrillogenic effects of cyanidin 3-rutinoside (C3R), purified from mulberry fruits, on bovine serum albumin (BSA) under aggregation-promoting conditions, using multispectral, microstructure, and molecular docking approaches. Results showed that C3R dose-dependently inhibited BSA-aggregations under the glycation conditions through separating the size peak, influencing Trp-intensity and hydrophobicity, affecting cross-β-sheet conformations, and microstructural declining the aggregates of glycated-BSA. Throughout the underlying mechanism behind the disaggregation effects, C3R altered the secondary structure, SDS-PAGE-bands, and XRD-peaks of glycated-BSA aggregates, as well as interacted with some of lysyl and arginine (Lys114, Lys431, Arg427, and Arg185) glycation sites of BSA. Overall, these results unleash that monomeric anthocyanins restrict BSA-aggregations under the glycation conditions which can assist in the design of reasonable therapeutics and functional foods. • The defibrillation effects of C3R on glycated-BSA were studied. • C3R dose-dependently disaggregated BSA under the glycation conditions. • C3R altered the secondary structures, particles size, and spectra of glycated-BSA aggregates. • C3R interacted with some of the lysyl and arginine glycation sites of BSA. [ABSTRACT FROM AUTHOR]

• Efficient DES-NPCE method was developed for anthocyanins extraction from blue honeysuckle. • Extraction process parameters were determined by rational experimental design methods. • Yields of anthocyanins and cyanidin-3-glucoside reached 6.601 mg/g and 4.839 mg/g. • Multiple kinetic models were used to analyze the extraction process and thermal stability. • Anthocyanins product exhibited powerful chemical and cellular antioxidant activities. In the present study, an integrated process for preparation of anthocyanins components from blue honeysuckle fruits using deep eutectic solvent-based negative pressure cavitation extraction (DES-NPCE) was explored rationally. Single factor optimization combined with Box-Behnken Design (BBD) were applied to confirm the influential parameters. The maximum extraction yields of total anthocyanins and main constituent cyanidin-3-glucoside (C3G) reached 6.601 mg/g and 4.839 mg/g, which were 1.197–1.565 folds of other conventional methods. Moreover, the anthocyanins products exhibited higher stability from DES-NPCE extraction than that of conventional extraction solvents, which was conducive to the preservation and utilization of anthocyanins. After enrichment with macroporous resin D101, the contents of total anthocyanins and C3G reached 25.72% and 19.05%, and the recovery yields were 81.35% and 82.24%, respectively. Furthermore, the anthocyanins products exhibited more powerful chemical and cellular antioxidant activities, which were similar or stronger than that of positive control Vc or BHT. These results revealed that the proposed process was definitely an efficient and sustainable strategy for the stabilization preparation of thermo sensitive biologically active natural products. The developed method has also proved to have sufficient potential for application in food, nutrition and pharmaceutical industries. [ABSTRACT FROM AUTHOR]

α-Glucosidase inhibitors are widely used to suppress postprandial glycemia in the treatment of type 2 diabetes mellitus. The present study evaluated the in vitro α-glucosidase inhibitory activity of three major pigment constituents of Cinnamomum camphora fruit, namely cyanidin, cyanidin 3-rutinoside, and cyanidin-3-O-glucoside. We found that cyanidin exerted strong inhibitory activity on α-glucosidase, with IC 50 of 5.293 × 10−3 mM, whereas cyanidin 3-rutinoside and cyanidin-3-O-glucoside did not show inhibitory activity on α-glucosidase. The inhibitory activity of cyanidin was stronger than that of acarbose (IC 50 1.644 mM), the current most commonly used drug for postprandial glycemia. Kinetic analysis indicated that cyanidin inhibited α-glucosidase through competition, with a K i value of 0.0183 mM. Fluorescence spectrum titration showed only one binding site between cyanidin and α-glucosidase, and the binding constant was calculated. Further, molecular docking was conducted to simulate the binding interactions between cyanidin and α-glucosidase. Cyanidin was found to interact with several residues close to the catalytic site of α-glucosidase through π-π stack interaction and hydrogen bonds. The calculated binding energy of the cyanidin and enzyme complex was −105.031 kJ/mol. Molecular simulation and calculation showed that the van der Waals force played an essential role in the binding of α-glucosidase and cyanidin. [ABSTRACT FROM AUTHOR]

Cranberry phytochemicals are known to possess antiviral activities. In the current study, we explored the therapeutic potential of cranberry against SARS-CoV-2 by targeting its main protease (Mpro) enzyme. Firstly, phytochemicals of cranberry origin were identified from three independent databases. Subsequently, virtual screening, using molecular docking and molecular dynamics simulation approaches, led to the identification of three lead phytochemicals namely, cyanidin 3-O-galactoside, β-carotene and epicatechin. Furthermore, in vitro enzymatic assays revealed that cyanidin 3-O-galactoside had the highest inhibitory potential with IC 50 of 9.98 μM compared to the other two phytochemicals. Cyanidin 3-O-galactoside belongs to the class of anthocyanins. Anthocyanins extracted from frozen cranberry also exhibited the highest inhibitory potential with IC 50 of 23.58 μg/ml compared to the extracts of carotenoids and flavanols, the class for β-carotene and epicatechin, respectively. Finally, we confirm the presence of the phytochemicals in the cranberry extracts using targeted LC-MS/MS analysis. Our results, therefore, indicate that the identified cranberry-derived bioactive compounds as well as cranberry could be used for therapeutic interventions against SARS-CoV-2. • Main protease (Mpro) is involved in viral replication of SARS-CoV-2 • Virtual screening identified 3 cranberry phytochemicals with strong binding affinity for Mpro • These bioactive compounds were cyanidin 3-O-galactoside, β-carotene and epicatechin • Chemical standards of the phytochemicals showed micromolar IC 50 values in enzymatic assay • Anthocyanins extracted from cranberry showed highest inhibition of Mpro [ABSTRACT FROM AUTHOR]

The accumulation of anthocyanins can be found in both the fruit and petioles of strawberries, but the fruit appears red while the petioles appear purple-red. Additionally, in the white-fruited diploid strawberries, the petioles can accumulate anthocyanins normally, suggesting a different synthesis pattern between the petioles and fruits. We screened the EMS mutagenized population of a red-fruited diploid strawberry 'Ruegen' and discovered a mutant which showed no anthocyanin accumulation in the petioles but normal accumulation in the fruit. Through BSA sequencing and allelic test, it was found that a mutation in FvDFR2 was responsible for this phenotype. Furthermore, the complex formed by the interaction between the petiole-specific FvMYB10L and FvTT8 only binds the promoter of FvDFR2 but not FvDFR1 , resulting in the expression of only FvDFR2 in the petiole. FvDFR2 can catalyze the conversion of DHQ and eventually the formation of cyanidin and peonidin, giving the petiole a purplish-red color. In the fruit, however, both FvDFR1 and FvDFR2 can be expressed, which can mediate the synthesis of cyanidin and pelargonidin. Our study clearly reveals different regulation of FvDFR1 and FvDFR2 in mediating anthocyanin synthesis in petioles and fruits. • Mutations in FvDFR2 result in a phenotype of green petiole in strawberry. • In petioles, only FvDFR2 expressed while both FvDFR1 and FvDFR2 expressed in fruits. • FvMYB10L and FvTT8 selectively binds to the FvDFR2 promoter instead of FvDFR1. • FvDFR1 compensates for the loss of FvDFR2 function in forming cyanidin in fruits. [ABSTRACT FROM AUTHOR]

• We precisely investigated anthocyanin composition using ultra-performance liquid chromatography-mass spectrum in Phalaenopsis -type Dendrobium hybrids (Den-Phals). It suggested that the cyanidin-type anyhocyanin were the major components content over 85 %. Pelargonidin was almost the only pigment in reddish pink flowers. The slightly higher peonidin content contributed to purple-violet flowers. • With the increase of total anthocyanidin and cyanidin pigments, the floral color deepened and turned to purple. Flavones or flavonols as co-pigments contributed to brighter and yellower color. • The varied output from the anthocyanin biosynthetic pathway among Den-Phals was used to identify the rate-limiting steps involved and a strategy for the cultivation of pure red, blue, and violet flowers is proposed. Floral color is an important Phalaenopsis -type Dendrobium hybrids (Den-Phals) trait in the flower markets. Anthocyanins are key pigments contributing to purple, pink, and violet floral color. However, the impact of anthocyanin composition on flower coloration has not yet been fully elucidated. In this study, the flower color characteristics of 62 Den-Phals were evaluated. Most flowers contained purple, while pure blue, orange, and red floral colors were scarce. In total 35 anthocyanins were identified and two acylated pelargonidin glycosides were tentatively characterized using ultra-performance liquid chromatography (UPLC)-mass spectrum (MS) analysis. Unfortunately, the major anthocyanin components remained unidentified. However, the hydrolysis anthocyanins to their anthocyanidins suggested that the cyanidin was the major component in most hybrids with a relative content over 85 %. Pelargonidin was almost the only pigment in reddish pink flowers. The slightly higher peonidin content was found in purple-violet flowers (up to 6.23 %). The trend indicated that with the increase of total anthocyanidin and cyanidin pigments, the floral color deepened and turned to purple. Flavones or flavonols as co-pigments contributed to brighter and yellower color. From the above results, the varied output from the anthocyanin biosynthetic pathway among Den-Phals was used to identify the rate-limiting steps involved and a strategy for the cultivation of pure red, blue, and violet flowers is proposed. The study provides a basis for screening excellent germplasm and improving floral color in Den-Phals. [ABSTRACT FROM AUTHOR]

Alzheimer's disease (AD) is associated with the deposition of amyloid-β (Aβ) fibrillary aggregates. Disaggregation of Aβ fibrils is considered as one of the promising AD treatments. Recent experimental studies showed that anthocyanidins, one type of flavonoids abundant in fruits/vegetables, can disaggregate Aβ fibrillary aggregates. However, their relative disruptive capacities and underlying mechanisms are largely unknown. Herein, we investigated the detailed interactions between five most common anthocyanidins (cyanidin, aurantinidin, peonidin, delphinidin, and pelargonidin) and Aβ protofibril (an intermediate of Aβ fibrillization) by performing microsecond molecular dynamic simulations. We found that all five anthocyanidins can destroy F4-L34-V36 hydrophobic core and K28-A42 salt bridge, leading to Aβ protofibril destabilization. Aurantinidin exhibits the strongest damage to Aβ protofibril (with the most severe disruption on K28-A42 salt bridges), followed by cyanidin (with the most destructive effect on F4-L34-V36 core). Detailed analyses reveal that the protofibril-destruction capacities of anthocyanidins are subtly modulated by the interplay of anthocyanidin-protofibril hydrogen bonding, hydrophobic, aromatic stacking interactions, which are dictated by the number or location of hydroxyl/methyl groups of anthocyanidins. These findings provide important mechanistic insights into Aβ protofibril disaggregation by anthocyanidins, and suggest that aurantinidin/cyanidin may serve as promising starting-points for the development of new drug candidates against AD. [Display omitted] • Five similar anthocyanidin molecules display distinct disruptive effects and mechanisms of action on Aβ 1–42 protofibril. • Aurantinidin and cyanidin exhibit the best performance on Aβ protofibril disruption. • Aurantinidin exhibits the strongest damage to K28-A42 salt bridges, while cyanidin disrupts the F4-L34-V36 core most. • Anthocyanidins' disruptive capacity is modulated by the interplay of H-bonding, hydrophobic, and π-π interactions. [ABSTRACT FROM AUTHOR]

[Display omitted] • Blueberry anthocyanins were encapsulated by ferritin nanocarriers. • The stability of ferritin-encapsulated anthocyanins was enhanced. • Ferritin nanocarriers could prolong gastrointestinal anthocyanin release. Blueberries contain an important amount of anthocyanins, which possess numerous biological properties. Nonetheless, the potential applications of anthocyanins may be constrained due to their limited stability and bioavailability. This study aimed to evaluate the stability and absorption of blueberry anthocyanin extracts (BAE) and anthocyanin standards (malvidin and cyanidin glycosides) when encapsulated using ferritin (FR) nanocarriers or a combination of FR and sodium alginate (SA) under simulated gastrointestinal conditions and Caco-2 cell monolayers. These results indicate that the use of FR nanocarriers resulted in an extended-release of anthocyanins during simulated digestion. Particularly, it was observed that after a period of 2 h in the intestinal phase, the anthocyanin concentration in BAE was greater (38.01 μg/mL, P < 0.05) when FR nanocarriers were employed, in comparison to untreated BAE (4.12 μg/mL). Furthermore, outcomes obtained from the Caco-2 cell monolayer assay revealed that FR-anthocyanin encapsulation resulted in substantially higher (P < 0.05) absorption rates ranging from 25.09 to 44.59 % compared to untreated anthocyanins (10.61–22.95 %). These findings provide evidence of an innovative approach for enhancing the stability and bioavailability of blueberry anthocyanins. [ABSTRACT FROM AUTHOR]

• The flavonoid contents in stored rice were higher than those in fresh rice. • Differential flavonoids at Month 3 and Month 5 of storage were more in composition and concentration. • Flavone, flavonol, isoflavone, and anthocyanidin were the main flavonoids in yellowed rice. • Rutin, farrerol, naringenin, and diosmetin were indicators of rice yellowing. • Anthocyanidin, flavone, flavonol and isoflavone co-determined the yellow color of rice. Flavonoids are the main metabolites responsible for yellowing of rice. However, the accumulation pattern of flavonoids and the metabolic basis of flavonoid biosynthesis during rice yellowing remain unclear. Thus, flavonoid-targeted metabolomics was used to investigate the composition and concentration of flavonoids in rice during yellowing. The results indicated the differential flavonoids at Month 3 and Month 5 of storage were more in composition and concentration with higher antioxidant capacity. Accumulated flavonoids were mainly flavones, flavonols, isoflavones, and anthocyanidins, of which rutin, farrerol, naringenin, cyanidin 3-rutinoside, and diosmetin were the indicators of rice yellowing. Metabolic association among flavonoids demonstrated the formation of yellow pigments was jointly induced by flavones, flavonols, isoflavones, and anthocyanidins metabolism. Examination of flavonoid metabolism presented in this study enhanced current understanding of the relationship between flavonoid metabolites and development of rice yellowing. It also offers a theoretical basis for targeted prediction of rice yellowing in the future. [ABSTRACT FROM AUTHOR]

• Development of a microwave extraction method with a variable input power (VPME). • Improvement of extraction yield and reduction of degradation of anthocyanins in VPME. • Optimization of VPME parameters for the anthocyanins from blueberry powder. A variable power of microwave extraction (VPME) method with two-stage input power is developed to improve the extraction rate and reduce the degradation of anthocyanins from blueberry powder. Microwave powers of 700–1100 W at the 1st stage, microwave powers of 100–500 W at the 2st stage, and transition temperatures of 30–46 °C as medium quantity from 1st stage to 2st stage were selected as influencing factors in the microwave extraction (MAE). Results indicate that high microwave power at the 1st stage of VPME may rupture the cell wall of blueberry to weaken the diffusion resistance of anthocyanins to improve its yield, and low microwave power at the 2st stage reduces the degradation of anthocyanin. The extraction kinetics of anthocyanins considering cell walls broken obeys the exponential function in microwave power of 700–1100 W. The highest anthocyanin acquistion rate of 84.82% and the lowest anthocyanin degradation rate of 8.13% from blueberry powder were achieved under microwave power of 800 W at the 1st stage, the transition temperature of 36 °C and microwave power of 280 W at the 2st stage. Five species of anthocyanin monomers including delphinidin, cyanidin, petunidin, peonidin and malvidin were detected in the extracts from blueberry. The yield of anthocyanin extracted by the VPME was 17.75% higher than that of the microwave extraction of constant power. Microwave extraction with two-stage input power may improve the extraction rate of anthocyanins from blueberry powder with low degradation. [ABSTRACT FROM AUTHOR]

• Cold hardy rye genotypes accumulated the highest amounts and diversity of anthocyanins. • Glycosylated cyanidins were preferentially accumulated in cold hardy genotypes. • Delphinidin and pelargonidin glycosides were unrelated to cold hardiness. • A higher accumulation of anthocyanins in leaves than in crowns upon cold acclimation. Fall-seeded rye improve their frost resistance during a cold acclimation period in the fall, which is often associated with an accumulation of red/purple-colored anthocyanins in plant tissues. The pigments provide antioxidant activity and are proposed to scavenge excess reactive oxygen species (ROS) and mitigate light stress occurring during cold exposure. The relationship between anthocyanin and winter hardiness in rye (Secale cereale L.) was assessed by analyzing 96 genotypes with varying levels of winter survival. HPLC-QTOF MS/MS analyses of tissue extracts prepared from cold-acclimated plants revealed presence of accumulated anthocyanins in leaves of 74 genotypes and 51 of these showed low levels of anthocyanins presence in crown tissues. An overall higher abundance and diversity of anthocyanins was noted for the most cold-hardy as compared to the less hardy genotypes. A total of 18 anthocyanins originating from the pelargonidin, cyanidin, and delphinidin precursors were identified, of which the glycosylated cyanidins were accumulated in 37 of the 39 most winter hardy genotypes, but only detected in six of the 38 most tender genotypes. The link between anthocyanin concentration and profiles with winter-hardiness levels for the 96 rye genotypes suggested a role for cyanidin-derived anthocyanins in mediating enhanced winter hardiness in rye. [ABSTRACT FROM AUTHOR]

Plants belonging to the genus Passiflora produce exuberant flowers with characteristic corona filaments that vary widely in size, morphology and color. This variability is thought to be an adaptation to different animal pollinators. In general, Passiflora flowers are pollinated by bees, hummingbirds and bats. The aim of this study was to identify the anthocyanins present in the corona filaments of two wild parent species, P. incarnata and P. coccinea, that are pollinated by bees and hummingbirds, respectively, and their artificial commercial hybrid P. 'Lady Margaret'. The anthocyanin profiles of the corona filaments were characterized by ultra-high performance chromatography with electrospray ionization and tandem mass spectrometry (UHPLC-ESI-MS/MS). Monoglucosides of two anthocyanidins (cyanidin and pelargonidin) were found in P. coccinea corona filaments, whereas diglucosides of four anthocyanidins (cyanidin, petunidin, peonidin and malvidin) were identified in P. incarnata corona. The P. 'Lady Margaret' hybrid contained both mono and diglucosides of the anthocyanidins identified in the parent species and also novel anthocyanin molecules not found in the parents. The use of UHPLC-ESI-MS/MS was an efficient method to identify the anthocyanins present in the corona of Passiflora species. P. incarnata acquired its red flowers by suppression of the delphinidin pathway. The wide variety of anthocyanins found in the corona filaments of the P. 'Lady Margaret' interspecific hybrid indicated that it inherited the anthocyanidin pathways as well as the glycosylation pattern of both parent species. • Cyanidin and pelargonidin provide the red color of P. coccinea corona. • P. incarnata acquired its red flowers by suppression of the delphinidin pathway. • Cyanidin, petunidin, peonidin and malvidin pigment the corona of P. incarnata. • The interspecific hybrid inherited the anthocyanidins identified in the parentals. • The interspecific hybrid produced novel anthocyanin molecules not found in parentals. [ABSTRACT FROM AUTHOR]

Abstract This work aims to explore the molecular binding mechanisms of two major soy protein fractions, β-conglycinin (7S) and glycinin (11S) with cyanidin-3-O-glucoside (C3G, a representative polyphenol in food) at pH 7.0. Circular dichroism spectroscopy manifested that C3G induced the conversion of β-sheet into α-helix and random coil. Synchronous fluorescence and three-dimensional fluorescence spectroscopy confirmed the unfolding and loosing of protein molecules. Furthermore, the results from fluorescence quenching and isothermal titration calorimetry indicated that C3G quenched fluorescence of two proteins in a static mode, and their interactions were entropically favorable processes driven by a combination of hydrophobic interaction and electrostatic force. 11S had a higher affinity for C3G than 7S, as indicated by the binding constant and binding sites. In addition, the surface hydrophobicity and thermal stability of two proteins were reduced after C3G binding. This study will help further understand the interaction mechanism between 7S/11S and polyphenols. Graphical abstract Image 1 Highlights • The binding interactions between 7S/11S and C3G at neutral pH were investigated for the first time. • Their interactions were entropically favorable processes driven by electrostatic and hydrophobic interaction. • Their interactions changed the secondary and tertiary structure of two proteins. • Their interactions decreased the surface hydrophobicity and thermal stability of two proteins. • 11S had a stronger binding ability and more binding sites for C3G than 7S. [ABSTRACT FROM AUTHOR]

Abstract The structural forms of cyanidin and cyanidin 3- O - β -glucopyranoside (Cy3Glc) were investigated in the pH range from 0.4 to 13.5 for cyanidin and 0.4 to 13.2 for Cy3Glc. The 3-glucosidic substitution in cyanidin 3- O -β-glucopyranoside at pH values lower than 4.0 was manifested in a large hyperchromic effect, while at pH values higher than 4.0 had the opposite effect and resulted in high hypochromic effect. Multivariate data analysis showed that the structural forms of cyanidin and Cy3Glc have numerous bends, which mutually overlap and influence the shape, position, and intensity of their spectrophotometric measurements. For cyanidin seven structural forms were identified, while for Cy3Glc six structural forms were identified, and one was not. To determine the stability of cyanidin and Cy3Glc at different pHs, HPLC–DAD–ESI/MS analysis was performed. The stability was tested in buffers at four pH values between 2 and 9. Degradation products formed from cyanidin and Cy3Glc at different time in the different buffer solutions were tracked and some of them were identified. Cyanidin stability was decreased in the following order pH 7.0, pH 4.0, pH 2.0, pH 9.0. Stability of Cy3Glc was increasing with decreasing the pH. Cy3Glc was the most stable at pH 2.0, and the least stable at pH 9.0. Highlights • At pH < 4, the 3-glucosidic substitution of cyanidin resulted in a very high hyperchromic effect. • At pH > 4 the 3-glucosidic substitution of cyanidin resulted in a very high hypochromic effect. • Cyanidin stability is decreased in the following order pH 7.0, pH 4.0, pH 2.0, pH 9,0. • Stability Cy3Glc was increased with pH decreasing, and was the most stable at pH 2.0, and the most unstable at pH 9.0. • For cyanidin seven structural forms were identified, while for Cy3Glc six structural forms were identified, and one was not. [ABSTRACT FROM AUTHOR]

Highlights • Two major anthocyanins of sour cherries were isolated. • Sucrose led to reduction in the stabilities of both anthocyanins. • Cherry stem extract (CSE) showed copigmentation effects on these anthocyanins. • Cyanidin-3-glucosylrutinoside caused more stable copigmentation with copigments in CSE. • Interaction between cyanidin-3-rutinoside and copigments in CSE was faster. Abstract Cyanidin-3- O -glucosylrutinoside and cyanidin-3- O -rutinoside were isolated from sour cherry juice concentrate (SCJC). Sucrose and copigments [gallic acid (GA), cherry stem extract (CSE) and pomegranate rind extract (PRE)] were added to these anthocyanins. Effects of sucrose and copigments on the isolated anthocyanins were studied during storage at 20 °C for 140 days. All copigment sources provided protection against degradation effect of sucrose on the isolated anthocyanins before storage. Although GA increased the stabilities of both isolated anthocyanins, only CSE had copigmentation effect on both isolated anthocyanins. Copigmentation effect on cyanidin-3- O -glucosylrutinoside continued throughout storage. However, this effect on cyanidin-3- O -rutinoside continued for only 56 days of storage. Cyanidin-3- O -glucosylrutinoside containing three sugar moieties was more prone to copigmentation than cyanidine-3-rutinoside containing two sugar moieties. Results showed that the presence of more than one anthocyanin in a media changed stability of copigmentation. We recommend CSE for enhancement in colour density, but GA for enhancement in anthocyanin stability. [ABSTRACT FROM AUTHOR]

Recent studies suggest that phytochemicals, as part of the food matrix, might alter the toxicity of nanoparticles (NPs); however, relatively few studies have investigated the impact of anthocyanidins on the toxicity of NPs to cells lining the gastrointestinal tract. Therefore, this study used cyanidin chloride (CC) as the model for anthocyanidins and investigated the effects of CC on the toxicity of ZnO or Ag NPs to Caco-2 cells. Exposure to ZnO but not Ag NPs significantly induced cytotoxicity. The presence of CC, but not its analog quercetin (Qu), modestly protected Caco-2 cells from ZnO NP exposure. However, the intracellular superoxide, Zn ions, or release of interleukin-8 after ZnO NP exposure were not significantly affected by the presence of CC. Rather, CC promoted the expression of autophagic genes ATG5 , ATG7 , and BECN1 as well as the ratio of LC3-II/I after exposure to ZnO NPs. Meanwhile, the presence of autophagic inhibitors (chloroquine, NH 4 Cl, bafilomycin A1) significantly promoted the cytotoxicity of ZnO NPs and inhibited the cytoprotective effects of CC. In conclusion, these data suggest that CC could modestly protect Caco-2 cells from ZnO NP exposure, probably through the induction of autophagy. Image 1 • ZnO but not Ag NPs significantly induced cytotoxicity to Caco-2 cells. • Cyanidin chloride (CC)/quercetin (Qu) had minimal impact on colloidal properties of ZnO/Ag NPs. • CC but not Qu modestly protected Caco-2 cells from ZnO NP exposure. • ZnO NP-induced intracellular superoxide, Zn ions and IL-8 release were not affected CC. • CC promoted autophagy activity, which may be responsible for the cytoprotective effects. [ABSTRACT FROM AUTHOR]

Highlights • Stereochemistry and glycosidic linkage of cyanidin-3-glycosides impacted reactivity. • Cyanidin-3-galactoside bleached & hydrated more than cyanidin-3-glucoside. • Cyanidin (Cy) with 1 → 6 disaccharides had higher t 1/2 than with 1 → 2 dissacharides. • 1 → 2 disaccharides resisted hydration & bleaching more than their 1 → 6 counterparts. • Cy with 1 → 2 & 1 → 6 trisaccharide showed greatest stability & intermediate bleaching. Abstract The impact of glycosylation on anthocyanin stability has largely been associated with sugar type, site, and size, with glycosyl stereochemistry being under-explored. Seven cyanidin-3-glycosides were isolated by HPLC, diluted in pH 1–9, mixed with bisulfite or ascorbic acid at pH 3, and stored for 8 weeks (25 °C, dark). Spectral changes, half-lives, and bleaching rates were determined. Cyanidin-3-galactoside was more reactive (susceptible to hydration and bleaching) than cyanidin-3-glucoside. The 1 → 2 disaccharides exhibited greater λ vis-max (≤16 nm), resistance to hydration, and bleaching compared to 1 → 6 disaccharides.The 1 → 6 disaccharides had similar λ vis-max (∼2 nm) to the monosaccharides but slightly improved resistance to hydration and bleaching. The tri-glycosylated anthocyanin had the greatest stability and its spectral and bleaching characteristics was intermediate to 1 → 2 and 1 → 6 disaccharides. The 1 → 2 disaccharides generally exhibited lower half-lives compared to monosaccharides; whereas, 1 → 6 disaccharides exhibited higher stability. These findings highlight the role of glycosyl assembly on anthocyanin reactivity and stability. [ABSTRACT FROM AUTHOR]

Highlights • The serum concentrations of anthocyanin were increased by capsaicin or capsiate. • The intestinal absorption of black chokeberry was lower than that of haskap. • The capsaicin and capsiate may open tight junctions in the rat small intestine. Abstract Recent studies have shown that aronia (black chokeberry) and haskap fruits (contain anthocyanins) have beneficial health effects in animals and humans. However, some reports have shown that anthocyanin is poorly absorbed in the small intestine. In this study, we compared the intestinal absorption of aronia and haskap anthocyanins by using rats with a ligated small intestinal loop and cannulated portal vein. Our results clearly showed that the intestinal absorption of aronia anthocyanins was significantly lower than that of haskap anthocyanins, suggesting that the intestinal absorption of anthocyanins is influenced by the glycoside type (galactoside or glucoside). In addition, we also examined the effects of capsaicin and capsiate on intestinal anthocyanin absorption. The amount of aronia anthocyanins in portal blood was much higher when they were co-administered with capsaicin or capsiate. Our study is the first to show that the intestinal absorption of aronia anthocyanins is promoted by capsaicin and capsiate. [ABSTRACT FROM AUTHOR]

Highlights • Methylpyranocyanidin-3- O -glucoside was increased 32.5% by ultrasonic for 40 min. • Excessive ultrasonic treatment have a negative effect on formation of derivative. • Derivative exhibits a better heat, pH and SO 2 stability than its precursor. Abstract Pyranoanthocyanins are anthocyanin derivatives that are formed during fermentation and oxygenation processes in aged wine. They play a critical role in assessing the aging of wine based on its colour quality. Naturally, the formation process of pyranoanthocyanins is fairly slow. In this respect, the present work studies the role and efficiency of ultrasonic treatment in accelerating the formation of methylpyranocyanidin-3- O -glucoside and investigates the spectral characteristics as well as the stability of this derivative toward heat, bisulfite bleaching and pH variation in a simulation system. Our results showed that the yield of methylpyranocyanidin-3- O -glucoside can be increased by 32.5% by ultrasonic treatment at 100 W for 40 min, and excessive treatment (≥60 min) does not have a positive effect on the yield. Moreover, this derivative exhibits a better stability toward heat, pH variation and bisulfite bleaching than its precursor cyanidin-3- O -glucoside. [ABSTRACT FROM AUTHOR]

Highlights • Hibiscus sabdariffa calyx is a rich source of cyanidin-/delphinidin-based anthocyanins. • Up to 23.83 ± 2.44 mg of the target anthocyanins can be quantified in 1 g of dried calyx. • Two anthocyanins were recovered by heat- and ultrasound-assisted extraction methods. • Time, ethanol proportion, temperature and ultrasonic power were significant variables. • UAE was the most efficient method yielding 51.76 ± 3.70 mg anthocyanins/g extract. Abstract Heat- and ultrasound-assisted extraction methods were applied to recover anthocyanins from Hibiscus sabdariffa calyces. The extraction variables, time (t), ethanol proportion (S), and temperature (T) or ultrasonic power (P), were combined in a 5-level experimental design and analysed by response surface methodology for process optimization. The delphinidin-3- O -sambubioside (C 1) and cyanidin-3- O -sambubioside (C 2) levels were monitored by LC-DAD-ESI/MSn and used as response criteria. The developed models were successfully fitted to the experimental data and used to determine optimal extraction conditions. UAE was the most efficient method yielding 51.76 mg C1 + C 2/g R under optimal conditions (t = 26.1 min, P = 296.6 W and S = 39.1% ethanol, v/v). The dose-response effects of the solid/liquid ratio on the extraction rate were also determined. The anthocyanin levels herein reported are higher than those found in the literature, which support the potential use of H. sabdariffa as a sustainable source of natural colorants with application in different industrial sectors. [ABSTRACT FROM AUTHOR]