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Anthocyanin is an important flavonoid with antioxidant, anticancer, and anti-inflammatory properties. This research investigates the anthocyanin content of Cavendish banana inflorescence, a by-product often discarded as agricultural waste. The study employs two drying methods, namely oven-drying and freeze-drying, followed by accelerated solvent extraction using acidified water and methanol. Liquid chromatography-mass spectroscopy (LC-MS) results confirm banana inflorescence as a rich source of anthocyanins. According to LC-MS analysis, freeze-dried banana inflorescence extracted in methanol at 80 °C exhibits the highest anthocyanin content (130.01 mg/100 g). This sample also demonstrates superior characteristics, including a chroma value of 40.02 ± 0.01, a redness value of 38.09 ± 0.16, 18.46 ± 0.02 °Brix, a total phenolic content of 42.5 ± 1.00 mg/g, expressed as gallic acid equivalents, and a total antioxidant activity of 71.33 ± 0.08% when assessed with the DPPH method. Furthermore, the study identifies the predominant anthocyanin as cyanidin, along with the presence of other anthocyanins such as delphinidin (Dp), malvidin (Mv), petunidin (Pt), pelargonidin (Pg), and peonidin (Pn). Interestingly, the extracted anthocyanins demonstrate pH sensitivity, changing from red to brown as pH increases. These findings highlight the potential of utilizing Cavendish banana inflorescence for anthocyanin extraction, offering sustainable waste valorization methods with promising applications in biomimetics and bioinspiration fields. [ABSTRACT FROM AUTHOR]

Anthocyanins, key quality components of tea, act as an important bridge between plants and the environment due to their function on protecting plants from biotic and abiotic irritants. This study aimed to assess the interactions between anthocyanins metabolism and the environment. Purple (P) and green (G) leaves with different anthocyanin contents were inoculated with tea plant anthracnose. High-throughput metabolomics and 16S microbial diversity sequencing methods were used to screen the anthocyanin fractions of tea plant leaves responsive to anthracnose. The interconnections between metabolites and the resistance of phyllosphere microorganisms to fungal pathogens were then analyzed. The results showed that leaves with high anthocyanin content (0.14% of diseased area ratio) were less impacted by anthracnose infestation than leaves with low anthocyanin (3.12%). The cyanidin content decreased after infection in purple leaves (PR) and increased in green leaves (GR). The relative abundance of Cyanobacteria was suppressed by the significant enrichment of Proteobacteria after anthracnose infection in green leaves. However, there were no significant differences between these two groups of microorganisms in purple leaves. Collinear network analysis revealed a strong correlation between Cyanobacteria and Dihydrosorbinol and between Proteobacteria and cyanidin metabolites. Among them, OTU456 (Bosea) was identified as the key taxonomic group of bacterial communities in the green-infected leaf network. In summary, the anthracnose resistance benefits from cyanidin mediated by proteobacteria in tea plants. These results deepen our understanding of the regulation of secondary metabolism in tea plants and the formation of plant resistance. [ABSTRACT FROM AUTHOR]

The aim of this study is to develop roselle (Hibiscus sabdariffa L.) extracts with high amounts of phytochemicals and in vitro antioxidant and antibacterial effects using green extraction technique. Roselle extract prepared by ultrasonic extraction with 80% ethanol and 1% hydrochloric acid (RSUEH) promoted the highest yield and high total phenolic (5.21 ± 0.05 g% gallic acid equivalent of dried extract), total flavonoid (1.29 ± 0.06 g% quercetin equivalent of dried extract), and total anthocyanin contents (0.21 ± 0.00 and 0.44 ± 0.00 g% cyanidin 3‐glucoside equivalent of dried extract determined by pH‐differential method with standard calculation and pH‐differential method with standard curve of cyanidin 3‐glucoside, respectively). From the validated high‐performance liquid chromatography analysis, delphinidin‐3‐sambubioside, delphinidin‐3‐glucoside, and cyanidin‐3‐glucoside were found to be the major anthocyanins in roselle extract. This extract exhibited moderate 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) scavenging effect (EC50 289.61 ± 0.16 µg/mL) and strong inhibitory effects against Escherichia coli, Staphylococcus aureus, Staphylococcus intermedius, Proteus mirabilis, and Pseudomonas aeruginosa with the inhibitory concentration (IC50) values in the range of 0.15 ± 0.05 to 4.64 ± 0.07 mg/mL and the minimum inhibitory concentration (MIC) values ranged from 1.66 ± 0.06 to 7.11 ± 1.05 mg/mL. From partial purification, fraction 28 (F28) contained higher amounts of all analyzed phytochemicals than roselle extracts and promoted stronger DPPH scavenging effects (EC50 54.88 ± 2.23 µg/mL). F28 showed antibacterial activity with IC50 values against all tested bacteria in the range of 0.19 ± 0.07 to 4.69 ± 0.09 mg/mL, and the MIC values ranged from 2.46 ± 0.08 to 6.24 ± 0.09 mg/mL. [ABSTRACT FROM AUTHOR]

BACKGROUND RESULTS CONCLUSION Soybean reddening during storage and transportation has caused great concern due to the serious economic loss. However, the mechanism of reddening has not been clearly elucidated. In this study, metabolomics was employed to investigate the reasons for soybean reddening during storage.The results of multivariate statistical analysis showed that the metabolite level of red soybean was significantly different from that of normal soybean. The differentially expressed metabolites were mainly enriched by biosynthesis of secondary metabolites and amino acid metabolism. Metabolism analysis showed that the biosynthesis of cyanidin and betalains was enhanced in reddening soybean. In addition, it was found that phenolic and flavonoid compounds decreased, while quinones, furans and 5‐hydroxymethylfurfural increased in reddening soybeans compared to normal soybeans.The upregulation of cyanidin and betalains was the main reason for soybean reddening. Besides, the oxidation of phenols and flavonoids, as well as Maillard reaction, also contributed to the color change. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Background: Spine grape (Vitis davidii) is a promising source of high-quality anthocyanins, with vast potential for application in food, pharmaceutical, and cosmetic industries. However, their availability is limited by resource constraints. Plant cell culture has emerged as a valuable approach for anthocyanin production and serves as an ideal model to investigate the regulation of anthocyanin biosynthesis. Elicitors are employed to achieve targeted enhancement of anthocyanin biosynthesis. The present study investigated the impact of 5-aminolevulinic acid (ALA) as an elicitor on the accumulation of anthocyanins and flavonoids during spine grape callus growth. Specifically, we examined the effects of ALA on anthocyanin and its component accumulation in callus, and biosynthetic anthocyanin gene expression. Results: ALA at 25 µg/L increased the biomass of spine grape callus. ALA induction enhanced the levels of flavonoids, anthocyanins and proanthocyanidins in callus, with maximum values reaching 911.11 mg/100 g DW, 604.60 mg/100 g DW, and 5357.00 mg/100 g DW, respectively, after callus culture for 45 days. Notably, those levels were 1.47-, 1.93- and 1.83-fold higher than controls. ALA induction modulated the flavonoid profile, and among 97 differential flavonoid metabolites differing from controls, 77 were upregulated and 20 were downregulated. Six kinds of anthocyanins, namely cyanidin (8), delphinidin (6), peonidin (5), malvidin (4), petunidin (3) and pelargonidin (3), were detected in callus, with peonidin most abundant. Compared with controls, anthocyanin components were increased in ALA-treated callus. The key genes PAL1, PAL2, PAL4, CHI, CHS3, F3'H, F3H, FLS, DFR, UFGT, MYBA1, LDOX, OMT3, GT1 and ACT involved in anthocyanin biosynthesis were upregulated following ALA treatment, resulting in anthocyanin accumulation. Conclusion: This study revealed a novel mode of ALA-mediated promotion of plant anthocyanin biosynthesis and accumulation at the cellular level, and a strategy for enhancing anthocyanin content in spine grape callus. The findings advance commercial-scale production of anthocyanins via spine grape callus culture. we also explored the accumulation patterns of flavonoids and anthocyanins under ALA treatment. Augmentation of anthocyanins coincided with elevated expression levels of most genes involved in anthocyanin biosynthesis within spine grape callus following ALA treatment. [ABSTRACT FROM AUTHOR]

Green extraction primarily emphasizes developing new extraction techniques that consume less energy. It involves using safe, non‐toxic alternative solvents and sustainable natural resources to ensure the production of safe and high‐quality extracts. Red onion skin is an important source of anthocyanins, a subgroup of phenolic compounds. Anthocyanins are an important group of natural pigments that have attracted a lot of attention due to their health benefits. However, the instability and high sensitivity of these pigments have limited their use in food and cosmetics. Therefore, in this study, various modern green extraction methods were used, including solvent extraction, ultrasound‐assisted extraction, subcritical water extraction, microwave‐assisted extraction (MAE), pulsed electric field extraction, supercritical fluid extraction (SFE), and high hydrostatic pressure‐assisted (HHPAE) extraction, to specifically extract and purify anthocyanins. The extraction efficiency, specifically targeting anthocyanins, showed the highest efficiency with HHPAE (81.84%) and the lowest with MAE (40.01%). Measurement of total anthocyanin content revealed that HHPAE and SFE methods yielded the highest anthocyanin concentrations, with 248.49 and 244.98 mg/L, respectively. Identification of anthocyanin by LC–MS revealed that the main anthocyanidins in red onion peel are pelargonidin, cyanidin, delphinidin, and petunidin. These results indicate that innovative green extraction methods, particularly HHPAE and SFE, can effectively replace conventional techniques due to their superior efficiency and enhanced preservation of anthocyanin compounds. [ABSTRACT FROM AUTHOR]

Anthocyanins are bioactive compounds responsible for various physiological processes in plants and provide characteristic colors to fruits and flowers. Their biosynthetic pathway is well understood; however, the enzymatic degradation mechanism is less explored. Anthocyanase (β-glucosidase (BGL)), peroxidase (POD), and polyphenol oxidase (PPO) are enzymes involved in degrading anthocyanins in plants such as petunias, eggplants, and Sicilian oranges. The aim of this work was to investigate the physicochemical interactions between these enzymes and the identified anthocyanins (via UPLC-MS/MS) in cranberry (Vaccinium macrocarpon) through molecular docking to identify the residues likely involved in anthocyanin degradation. Three-dimensional models were constructed using the AlphaFold2 server based on consensus sequences specific to each enzyme. The models with the highest confidence scores (pLDDT) were selected, with BGL, POD, and PPO achieving scores of 87.6, 94.8, and 84.1, respectively. These models were then refined using molecular dynamics for 100 ns. Additionally, UPLC-MS/MS analysis identified various flavonoids in cranberries, including cyanidin, delphinidin, procyanidin B2 and B4, petunidin, pelargonidin, peonidin, and malvidin, providing important experimental data to support the study. Molecular docking simulations revealed the most stable interactions between anthocyanase and the anthocyanins cyanidin 3-arabinoside and cyanidin 3-glucoside, with a favorable ΔG of interaction between −9.3 and −9.2 kcal/mol. This study contributes to proposing a degradation mechanism and seeking inhibitors to prevent fruit discoloration. [ABSTRACT FROM AUTHOR]

The flavonoids play important roles in plant salt tolerance. Blueberries (Vaccinium spp.) are extremely sensitive to soil salt increases. Therefore, improving the salt resistance of blueberries by increasing the flavonoid content is crucial for the development of the blueberry industry. To explore the underlying molecular mechanism, we performed an integrated analysis of the metabolome and transcriptome of blueberry leaves under salt stress. We identified 525 differentially accumulated metabolites (DAMs) under salt stress vs. control treatment, primarily including members of the flavonoid class. We also identified 20,920 differentially expressed genes (DEGs) based on transcriptome data; of these, 568 differentially expressed transcription factors (TFs) were annotated, and bHLH123, OsHSP20, and HSP20 TFs might be responsible for blueberry leaf salt tolerance. DEGs involved in the flavonoid biosynthesis pathway were significantly enriched at almost all stages of salt stress. Salt treatment upregulated the expression of most flavonoid biosynthetic pathway genes and promoted the accumulation of flavonols, flavonol glycosides, flavans, proanthocyanidins, and anthocyanins. Correlation analysis suggested that 4-coumarate CoA ligases (4CL5 and 4CL1) play important roles in the accumulation of flavonols (quercetin and pinoquercetin) and flavan-3-ol (epicatechin and prodelphinidin C2) under salt stress, respectively. The flavonoid 3′5′-hydroxylases (F3′5′H) regulate anthocyanin (cyanidin 3-O-beta-D-sambubioside and delphinidin-3-O-glucoside chloride) biosynthesis, and leucoanthocyanidin reductases (LAR) are crucial for the biosynthesis of epicatechin and prodelphinidin C2 during salt stress. Taken together, it is one of the future breeding goals to cultivate salt-resistant blueberry varieties by increasing the expression of flavonoid biosynthetic genes, especially 4CL, F3′5′H, and LAR genes, to promote flavonoid content in blueberry leaves. [ABSTRACT FROM AUTHOR]

Objectives: This study was conceived with the aim of translating the experience and knowledge of the research group into the design and creation of multi-active phytocomplex cocktails from lyophilised winery by-products (Grape Pomace—GP) and weeds (Sambucus ebulus L., Dwarf Elder—DE). Methods: Quantification of bioactive molecules was performed by high-performance liquid chromatography (HPLC) method. Results: In the extract obtained from lyophilised GP, the most dominant component that was quantified was petunidin-3-glucoside. Prominent compounds that were quantified in DE extract were cyanidin derivatives. The total number of microorganisms in lyophilisates is low, but some of them still survive lyophilisation. Antibacterial activity was determined by microdilution, the minimum inhibitory concentration (MIC) of the tested bacteria ranged from 0.78 mg/mL to 25.00 mg/mL. Antibacterial susceptibility testing (AST) revealed that Klebsiella spp. and Acinetobacter baumannii complex are extensively drug-resistant (XDR). Conclusions: The GP + DE cocktail showed very strong AB power against both tested XDR bacteria. The total phenolic content and antioxidative effect (determined spectrophotometrically) indicate their linear correlation. [ABSTRACT FROM AUTHOR]

Purple-fleshed sweetpotato (PFSP) clones containing anthocyanins can be classified into two types based on their aglycone composition: normal peonidin-dominant (Pn-type) and unusual cyanidin-dominant (Cy-type) types. It is unclear how cyanidin dominance is selected in crossbreeding. To improve the breeding scheme, this study investigated the frequency distribution of Cy-type PFSP from three cross combinations. Cross No. 1 was derived by crossing Pn-type purple-fleshed ‘Purple Sweet Lord’ and orange-fleshed ‘90IDN-47,’ and Cross No.2 was from ‘Purple Sweet Lord’ and yellow-fleshed ‘Miyaakari.’ The cyanidin percentage of F1 plants differed significantly between these two crosses and Cross No.1 derived from ‘90IDN-47’ was found to be a superior cross for enhancing Cy-type clones. Cross No.3 was derived from both Cy-type PFSP parents, ‘Churakanasa’ and ‘Kyukei 90,143-4.’ In Cross No.3, all F1 plants were classified as Cy-type with a cyanidin content of ≥55%. This result emphasizes the importance of Cy-type PFSP parents as breeding materials.

BACKGROUND: Synchronous degradation between anthocyanin and vitamin C was found in fruit and vegetable juice matrices. To investigate whether the C‐ring of anthocyanin is the key site of this interaction, cyanidin with four different C‐ring modifications (3‐glucosylation, 3,5‐diglucosylation, 6″‐malonylation, pyranylation) was added to vitamin C‐containing apple juice, and the changes of anthocyanin retention, vitamin C retention, color, antioxidative activity and differential metabolites were analyzed. RESULTS: The anthocyanin retention was in the order of pyranylation >6″‐malonylation >3,5‐diglucosylation >3‐glucosylation. The vitamin C retention was in the order of 6″‐malonylation > pyranylation >3,5‐diglucosylation >3‐glucosylation. The order of color stability was the same as that of anthocyanin retention, and the order of antioxidative activity was opposite to that of vitamin C retention. The results showed that modification at the C‐ring limited the activity of anthocyanin, and suggested that the C‐ring was one of the key sites for anthocyanin and vitamin C interaction. The shared differential metabolite of all apple juice matrices added with different anthocyanins was trans‐hinokiresinol, which was likely generated from anthocyanin skeleton reacted with certain compounds in apple juice. CONCLUSION: This study showed that modification of the anthocyanin C‐ring could affect the anthocyanin and vitamin C interaction to some extent, which provided valuable insights for the application of anthocyanin C‐ring modification in shelf‐life quality control of typical fruit and vegetable beverages with the coexistence of anthocyanin and vitamin C. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Using “Lianjiu No.1”, “Yuntaihongjiu” and “Yuntaijinjiu” as research objects, the anthocyanin components and content of their leaves before and after color transformation were qualitatively and quantitatively analyzed using ultra-high performance liquid chromatographymass spectrometry technology.The results showed that a total of 14 anthocyanins were detected in leaves from three varieties, including malvidin, pelargonidin, delphinidin, peonidin, cyanidin 3-galactoside, isorhamnetin, cyanidin, cyanidin 3, 5-diglucoside, petunidin, quercetin, rutin, procyanidin B4, procyanidin B2 and kaempferol. Cyanidin 3-galactoside and rutin were the main anthocyanin components of three varieties. The cyanidin 3-galactoside was the main pigment component for the red colored leaves of “Yuntaihongjiu”; rutin was the main reason for the yellow colored leaves of “Yuntaijinjiu”. The main anthocyanins types in three varieties were rutins, cyanidins and others. After the color change of leaves, the content of cyanidins from high to low was in order of “Lianjiu No.1” > ”Yuntaihongjiu” > ”Yuntaijinjiu”. After the color change of leaves, the content of rutins from hight to low was in order of “Yuntaijinjiu” > “Lianjiu No.1” > “Yuntaihongjiu”. [ABSTRACT FROM AUTHOR]

Alcoholic liver disease (ALD) encompasses a spectrum of manifestations from simple steatosis to steatohepatitis, progressive fibrosis, cirrhosis and liver cancer. Emerging research has spotlighted flavonoids as promising candidates for interfering the initiation, promotion and progression of ALD. Thus this paper provides a comprehensive exposition on the effects of flavonoids on ALD and elucidates the underlying mechanisms. The results show that luteolin, soyasaponin, and isoliquiritigenin have demonstrated the ability to reduce liver fat synthesis, regulate lipid metabolism, and mitigate the undesirable accumulation of fat in hepatocytes. Quercetin and genistein exhibit excellent antioxidant properties, inhibiting lipid peroxidation and oxidative stress, thereby alleviating cellular inflammation and reducing the damage caused by alcohol to hepatocytes. Naringin, cyanidin, and butein also show promise in resisting liver fibrosis. The therapeutic effects of flavonoids on ALD have been validated through cell and animal experiments. However, the application development of flavonoids in functional foods still faces challenges due to insufficient research and industrialization hurdles. [ABSTRACT FROM AUTHOR]

Berries are highly valued for their rich phenolic content, particularly anthocyanins, which are known for their antioxidative properties and potential effectiveness against depression. This study identified and quantified anthocyanin profiles in blueberry, blackberry, black mulberry, and cranberry using ultra‐performance liquid chromatography–mass spectrometry (UPLC–MS), followed by in vivo evaluation of their antidepressant‐like activities. Blueberry and black mulberry showed significant levels of cyanidin‐3‐galactoside and cyanidin. Acute supplementation with these berries decreased serum corticosterone levels and increased monoamine neurotransmitters, while chronic supplementation enhanced antioxidative activity and reduced neuroinflammation in the hippocampus of mice. These findings indicate that the neurochemical, antioxidative, and anti‐inflammatory effects of blueberry and black mulberry mediate their therapeutic role against depression. Berries rich in cyanidin‐3‐galactoside and cyanidin may be valuable in developing functional foods, dietary supplements, and pharmacological formulations for mental health improvement. [ABSTRACT FROM AUTHOR]

Blackcurrant is an anthocyanin-rich berry with proven antioxidant and photoprotective activity and emerging prebiotic potential, widely applied in cosmetic products. Hereby, highly efficient enzyme-assisted extraction of blackcurrant polyphenols was performed, giving extract with very high antioxidant activity. Obtained extract was characterized in terms of anthocyanin composition, incorporated into three different cosmetic formulations and subjected to Franz cell diffusion study. Experimental values obtained using cellulose acetate membrane for all four dominant anthocyanins (delphinidin 3-glucoside, delphinidin 3-rutinoside, cyanidin 3-glucoside and cyanidin 3-rutinoside) were successfully fitted with the Korsmeyer–Peppas diffusion model. Calculated effective diffusion coefficients were higher for hydrogel compared to oil-in-water cream gel and oil-in-water emulsion, whereas the highest value was determined for cyanidin 3-rutinoside. On the other hand, after a 72 h long experiment with transdermal skin diffusion model (Strat-M® membrane), no anthocyanins were detected in the receptor fluid, and only 0.5% of the initial quantity from the donor compartment was extracted from the membrane itself after experiment with hydrogel. Present study revealed that hydrogel is a suitable carrier system for the topical delivery of blackcurrant anthocyanins, while dermal and transdermal delivery of these molecules is very limited, which implies its applicability for treatments targeting skin surface (i.e., prebiotic, photoprotective). [ABSTRACT FROM AUTHOR]

SUMMARY: Purple carrot accumulates anthocyanins modified with galactose, xylose, glucose, and sinapic acid. Most of the genes associated with anthocyanin biosynthesis have been identified, except for the glucosyltransferase genes involved in the step before the acylation in purple carrot. Anthocyanins are commonly glycosylated in reactions catalyzed by UDP‐sugar‐dependent glycosyltransferases (UGTs). Although many studies have been conducted on UGTs, the glucosylation of carrot anthocyanins remains unknown. Acyl‐glucose‐dependent glucosyltransferase activity modifying cyanidin 3‐xylosylgalactoside was detected in the crude protein extract prepared from purple carrot cultured cells. In addition, the corresponding enzyme was purified. The cDNA encoding this glucosyltransferase was isolated based on the partial amino acid sequence of the purified protein. The recombinant protein produced in Nicotiana benthamiana leaves via agroinfiltration exhibited anthocyanin glucosyltransferase activity. This glucosyltransferase belongs to the glycoside hydrolase family 3 (GH3). The expression pattern of the gene encoding this GH3‐type anthocyanin glucosyltransferase was consistent with anthocyanin accumulation in carrot tissues and cultured cells. Significance Statement: Glucosylation of the purple carrot anthocyanin cyanidin 3‐O‐(2″‐O‐xylosyl)‐(6″‐O‐sinapoylglucosyl)‐galactoside is mediated by a glycoside hydrolase family 3 vacuolar enzyme that catalyzes a reaction that uses acyl‐glucose as the glucosyl donor. [ABSTRACT FROM AUTHOR]

Background: Anthocyanins are water-soluble flavonoids in plants, which give plants bright colors and are widely used as food coloring agents, nutrients, and cosmetic additives. There are several limitations for traditional techniques of collecting anthocyanins from plant tissues, including species, origin, season, and technology. The benefits of using engineering microbial production of natural products include ease of use, controllability, and high efficiency. Results: In this study, ten genes encoding enzymes involved in the anthocyanin biosynthetic pathway were successfully cloned from anthocyanin-rich plant materials blueberry fruit and purple round eggplant rind. The Yeast Fab Assembly technology was utilized to construct the transcriptional units of these genes under different promoters. The transcriptional units of PAL and C4H, 4CL and CHS were fused and inserted into Chr. XVI and IV of yeast strain JDY52 respectively using homologous recombination to gain Strain A. The fragments containing the transcriptional units of CHI and F3H, F3'H and DFR were inserted into Chr. III and XVI to gain Strain B1. Strain B2 has the transcriptional units of ANS and 3GT in Chr. IV. Several anthocyanidins, including cyanidin, peonidin, pelargonidin, petunidin, and malvidin, were detected by LC-MS/MS following the predicted outcomes of the de novo biosynthesis of anthocyanins in S. cerevisiae using a multi-strain co-culture technique. Conclusions: We propose a novel concept for advancing the heterologous de novo anthocyanin biosynthetic pathway, as well as fundamental information and a theoretical framework for the ensuing optimization of the microbial synthesis of anthocyanins. [ABSTRACT FROM AUTHOR]

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【Objective】Hibiscus rosa-sinensis L. has high ornamental value due to rich flower colors and is widely used in urban greening and landscape architecture in South China. In order to provide theoretical and technical support for in-depth excavation of variety characteristics and flower color directional breeding technology, the characteristic differences of types and contents of anthocyanin in different flower colors were detected, and the specificity and common characteristics of different varieties of H. rosa-sinensis L. were analyzed.【Method】The anthocyanin composition and content of different petal tissues of white (W), red (R) and yellow (Y) flowers were determined by targeted metabolomics. Functional annotation, identification and analysis of metabolites were performed by using pathway enrichment analysis and multivariate statistical methods.【Result】The results showed that a total of 90 metabolites were detected in W, R and Y colors of H. rosa-sinensis L., among which 78 were differential metabolites, including cyanidin (41.11%), delphinidin (20.00%), peonidin (13.33%), and etc. There were 62 (Y vs R), 50 (Y vs W) and 65 (R vs W) differential metabolites among different flower colors, with a total of 22 common differential metabolites. Comprehensively considering the significance and absolute contents of differences in different comparative combinations, it was found thta the cyanidin-3-O-sambubioside-glucoside, pelargonidin-3-O-sophoroside, cyanidin-3-O-gentiobioside and peonidin-3-O-glucoside were relatively high in red flower; the delphinidin-3-O-(6'-Otartaryl) glucoside, procyanidin B4 and procyanidin B3 were relatively high in yellow flower. KEGG metabolic pathways analysis revealed that differential metabolites were significantly enriched in different flower color tissues.【Conclusion】The cyanidin3-O-sambubioside-glucoside, pelargonidin-3-O-sophoroside, cyanidin-3-O-gentiobioside and peonidin-3-O-glucoside were important metabolites determining the flower red color, while procyanidin B3 was an important metabolite determining the flower yellow color. This result preliminary revealed the differences in metabolites among different colors of H. rosa-sinensis L., which could provide theoretical references for the mechanism of color formation and color improvement for H. rosa-sinensis L.. [ABSTRACT FROM AUTHOR]

Cyanidin has a protective effect on the nervous system and has been reported to treat tumor effectively. However, its impact on glioma stem cells (GSC) is unknown. Using seven GSC lines, the anti-tumor effect of cyanidin is tested. The effect of cyanidin on the cell viability in each cell line is evaluated. Wnt signaling pathway-related genes are checked after treatment of cyanidin. Cytoplasmic/nuclear β-catenin protein levels post cyanidin treatment is detected. Protein levels of c-Myc after cyanidin treatment are determined. Twist1 and Snail1 protein levels after cyanidin treatment are checked as well. Cyanidin significantly reduces the cell viability of all GSCs, and exhibited the most substantial effect in GBM2 but no apparent effect in 293T cells. It can regulate the Wnt signaling pathway of all GSC lines. In the GBM2, GBM7, G166, and G179 cell lines, there is upregulation of WNT1 and MYC genes, while in the G144 and GliNS2 cell line, these two genes are down-regulated after cyanidin treatment. Cytoplasmic and nuclear protein levels of β-catenin in all cell lines are down-regulated. Cyanidin treatment significantly decreases the protein level for c-Myc in the GBM2 cell line compared with untreated cells, not in G144 or GliNS2 cells. Furthermore, cyanidin strongly reduces the expression of Twist1 and Snail1 in GBM2, G179, and G144 cell lines, while the GliNS2 cells show an opposite change in the cytoplasm and no change in nuclear. Cyanidin exerts an anti-tumor effect in glioma stem cell lines, probably through the Wnt signaling pathway. [ABSTRACT FROM AUTHOR]

Rhododendron simsii Planchon is an important ornamental species in the northern hemisphere. Flower color is an important objective of Rhododendron breeding programs. However, information on anthocyanin synthesis in R. simsii is limited. In this research, the regulatory mechanism of anthocyanin biosynthesis in R. simsii was performed through the integrated analysis of metabolome and RNA-seq. A total of 805 and 513 metabolites were screened by positive and negative ionization modes, respectively, In total, 79 flavonoids contained seven anthocyanidins, 42 flavanones, 10 flavans, 13 flavones, and seven flavonols. Methylated and glycosylated derivatives took up the most. Differentially accumulated metabolites were mainly involved in "flavone and flavonol biosynthesis", "cyanoamino acid metabolism", "pyrimidine metabolism", and "phenylalanine metabolism" pathways. For flavonoid biosynthesis, different expression of shikimate O-hydroxycinnamoyltransferase, caffeoyl-CoA O-methyltransferase, flavonoid 3′-monooxygenase, flavonol synthase, dihydroflavonol 4-reductase/flavanone 4-reductase, F3′5′H, chalcone synthase, leucoanthocyanidin reductase, and 5-O-(4-coumaroyl)-D-quinate 3′-monooxygenase genes ultimately led to different accumulations of quercetin, myricetin, cyanidin, and eriodictyol. In flavone and flavonol biosynthesis pathway, differential expression of F3′5′H, flavonoid 3′-monooxygenase and flavonol-3-O-glucoside/galactoside glucosyltransferase genes led to the differential accumulation of quercetin, isovitexin, and laricitrin. This research will provide a biochemical basis for further modification of flower color and genetic breeding in R. simsii and related Rhododendron species. [ABSTRACT FROM AUTHOR]

This research uses two different dosimetry techniques (films and gels) to evaluate how γ-rays affect Cyanidin chloride. The first method relies on combining CC with poly (vinyl alcohol) to create a thin film dosimeter, while the second uses CC with gelatin to create a gel dosimeter that is more sensitive to γ-rays. The produced film or gel changes visually from red to colorless when exposed to γ-rays. The usable dose range of films was up to 35 kGy, and for gels, it was between 10 and 150 Gy. All dosimetric characteristics were studied. [ABSTRACT FROM AUTHOR]

This work demonstrates the effectiveness of using alternative solvents to obtain jambolan extracts with a high content of bioactive compounds compared to conventional organic solvents, being the first study to evaluate the best ecological solvent alternative for Syzygium cumini (L.) Skeels. Five alternative solvents were used for extraction: water at 25 °C (W25), water at 50 °C (W50), water at 75 °C (W75), water with citric acid at 2.4% (CA2), and water with citric acid at 9.6% (CA9) in comparison with three conventional solvents: ethanol (EtOH), water with ethanol at 50% (WE), and water with methanol at 50% (WM). A protocol was then established for the extraction and concentration of samples obtained with these solvents. The highest content of total phenolic compounds (TPCs) in the extracts was obtained with the solvent W75 (1347.27 mg GAE/100 g), while in the concentrates it was the solvents EtOH (3823.03 mg GAE/100 g) and WM (4019.39 mg GAE/100 g). Total monomeric anthocyanins (TMAs) increased by 209.31% and 179.95% in extractions with CA2 and CA9, respectively, compared to pulp (35.57 mg eq c-3-g/100 g), demonstrating that they are the most efficient alternative solvents in this extraction. The levels of bioactive compounds and antioxidant activity varied according to the solvents used. Delphinidin 3,5-diglucoside, cyanidin 3,5-diglucoside, delphinidin 3-glucoside, petunidin 3,5-diglucoside, cyanidin 3-glucoside, peonidin 3,5-diglucoside, malvidin 3,5-diglucoside, petunidin 3-glucoside, and malvidin 3-glucoside were identified in most of the samples by UPLC-MS/MS. This study suggests that a simple procedure using alternative solvents can be used as an environmentally friendly strategy to achieve efficient extraction of bioactive compounds in jambolan. [ABSTRACT FROM AUTHOR]

Myocardial infarction is a worldwide disease with high morbidity and mortality and a major cause of chronic heart failure, seriously affecting patients' quality of life. Natural medicine has been used to cure or prevent cardiovascular disease for decades. As a natural flavonoid, anthocyanidin has been used to treat many diseases due to its antioxidative, anti-inflammatory, and other properties. A mouse model (C57BL/6) weighing 30–40 g was utilized to induce myocardial infarction by ligating the left anterior descending coronary artery. Cyanidin (30 mg/kg) was administered orally to mice for four weeks. A variety of assessments were used to evaluate cardiac function. The gene expression was measured using RNAseq and Western blot. Histological changes in myocardial tissue were assessed using staining techniques, including Masson, Hematoxylin Eosin (HE), and transmission electron microscopy. Tunnel staining was implemented as a method to detect cellular apoptosis. For the quantification of B-type natriuretic peptide (BNP) and atrial natriuretic peptide (ANP) in the serum, an enzyme-linked immunosorbent assay (ELISA) was employed. Furthermore, autodock simulation was executed in order to assess the interaction between cyanidin and a subset of genes. Cyanidin treatment inhibited myocardial cell apoptosis, improved cardiac function, and reduced serum concentrations of BNP and atrial natriuretic peptide ANP, as well as mitigated histological cardiac tissue damage. Cyanidin also inhibited the activity of matrix metalloproteinases (MMP2/9) and Fibronectin 1 (Fn1). Cyanidin improves heart function and reduces myocardial damage in mice after MI. Furthermore, cyanidin can prevent cardiomyocyte apoptosis. These effects are most likely caused by suppression of MMP9/2 and control of the Akt signaling pathway, suggesting an appropriate therapeutic target. [ABSTRACT FROM AUTHOR]

This study uses a modified electrode made of Molecularly Imprinted Polymers (MIPs) and Multi-Walled Carbon Nanotubes (MWCNTs) to provide a unique method for the extraction and electrochemical detection of cyanidin in berry fruits. The special pairing of MIPs with MWCNTs improves the sensors' sensitivity and selectivity, allowing for accurate cyanidin detection and quantification. The electropolymerization procedure was used to create the electrode, and TEM, XRD, and Raman studies were used to confirm its structure. Using Differential Pulse Voltammetry (DPV), the electrochemical response of the MIP/MWCNTs/GCE sensor was investigated. With a detection limit of 0.14 mg/mL, the sensor showed a linear range of 0.5 mg/mL to 242 mg/mL, demonstrating good sensitivity and adaptability. Real samples (berry fruits, human urine, and tap water) were used to further validate the sensor's performance, and the results revealed a strong correlation with the UPLC technique. The DPV approach showed excellent accuracy and suitability with low relative standard deviation values (less than 4.66%) and adequate recovery values (97.00–99.50%). Excellent selectivity, repeatability, and stability characterize the suggested MIP/MWCNTs/GCE sensor, which makes it a viable instrument for real-world uses in the food and environmental industries. This work advances the field by offering a more selective and sensitive way to identify cyanidin in berry fruits. [ABSTRACT FROM AUTHOR]

Chrysanthemum (Chrysanthemum morifolium, ground-cover Chrysanthemums), one of the important garden flowers, has a high ornamental and economic value. However, its ornamental value is significantly diminished by the low temperature experienced in northeastern China. Here, metabolomics and transcriptomics were performed on three Chrysanthemum cultivars before and after a low temperature to investigate the dynamic metabolite changes and the molecular regulatory mechanisms. The results showed that 1324 annotated metabolites were detected, among which 327 were identified as flavonoids derived from Chrysanthemum. The accumulation of metabolites and gene expression related to the flavonoid biosynthesis pathway significantly increased in the three cultivars under the low temperature, indicating flavonoid metabolism actively participates in the Chrysanthemum cold response. Specifically, the content of cyanidin and pelargonidin derivatives and the expression of anthocyanin biosynthesis genes significantly increases in XHBF, providing a reasonable explanation for the change in petal color from white to purple under the low temperature. Six candidate UDP-glycosyltransferase genes involved in the glycosylation of flavonoids were identified through correlation networks and phylogenetic analysis. CmNAC1, CmbZIP3, and other transcription factors potentially regulating flavonoid metabolism and responding to low temperatures were discovered by correlation analysis and weighted gene co-expression network analysis (WGCNA). In conclusion, this study elucidated the specific response of flavonoids to low temperatures in Chrysanthemums, providing valuable insights and metabolic data for investigating cold tolerance. [ABSTRACT FROM AUTHOR]

The medicinal plant Abrus precatorius L. was traditionally used in the Siddha and Ayurvedic systems of medicine in India. The Indian center of origin holds a vast variability in its seed color. The objective of this study was to assess the total monomeric anthocyanin, flavonol, as well as the antioxidative potential, protein content and ash content among the accessions. A total of 99 accessions conserved in the Indian National Genebank were used in this study. The methods used for the estimation of total monomeric anthocyanin, flavonol, as well as the antioxidative potential, protein content and ash content were the pH differential method, Oomah method, Ferric Reducing Antioxidant Potential, Dumas method and gravimetric method, respectively. The completely black colored accession was recorded with highest total monomeric anthocyanin (51.95 mg/100 g of cyanidin 3-glucoside equivalent) and flavonol content (66.41 mg/g of quercetin equivalent). Red + black colored accessions have recorded the maximum value with respect to antioxidants (14.18 mg/g of gallic acid equivalent). The highest amount of protein content was found in a completely white colored accession (20.67%) and the maximum ash content was recorded in red + black colored accession (4.01%). The promising accessions identified can be used by pharmaceutical companies in drug development and in curing degenerative diseases. [ABSTRACT FROM AUTHOR]

Blueberry anthocyanin-derived cyanidin (BAC) was used to prepare a series of responsive food freshness packaging films by compounding it with quaternary chitosan (QC) and gelatin (G). The fundamental properties, pH sensitivity, and functional attributes of the films were examined. The BAC solutions exhibited notable variations in color (from red to pink to violet) under different pH conditions. The incorporation of BAC resulted in improved UV–vis shielding capabilities but compromised the mechanical strength of the films (with tensile strength values from 85.02 to 44.89 MPa, elongation at break from 13.08% to 3.6%, and water vapor transmission rates from 5.24 × 10−9 to 7.80 × 10−9 g m−1 s−1 Pa−1). The QC-G-BAC films, containing 5–15 wt% BAC, exhibited noticeable color changes in acidic/ammonia environments within a short timeframe, easily discernible to the naked eye. Furthermore, the inclusion of BAC significantly enhanced the antioxidant and antimicrobial properties of the films. The addition of 5–15 wt% BAC to QC-G-BAC films could be employed for assessing the freshness of fresh shrimp (from red to dark red) and pasteurized milk (from red to dark earthy yellow). Among them, the total color difference (ΔE) of QC-G-BAC5 film was significantly correlated with the pH, acidity, and total colony count of pasteurized milk (R = 0.846, −0.930, −0.908, respectively). This new concept in smart packaging offers a straightforward and user-friendly freshness indicator. [ABSTRACT FROM AUTHOR]

Summary: Gorteria diffusa has elaborate petal spots that attract pollinators through sexual deception, but how G. diffusa controls spot development is largely unknown. Here, we investigate how pigmentation is regulated during spot formation.We determined the anthocyanin composition of G. diffusa petals and combined gene expression analysis with protein interaction assays to characterise R2R3‐MYBs that likely regulate pigment production in G. diffusa petal spots.We found that cyanidin 3‐glucoside pigments G. diffusa ray floret petals. Unlike other petal regions, spots contain a high proportion of malonylated anthocyanin. We identified three subgroup 6 R2R3‐MYB transcription factors (GdMYBSG6‐1,2,3) that likely activate the production of spot pigmentation. These genes are upregulated in developing spots and induce ectopic anthocyanin production upon heterologous expression in tobacco. Interaction assays suggest that these transcription factors regulate genes encoding three anthocyanin synthesis enzymes.We demonstrate that the elaboration of complex spots in G. diffusa begins with the accumulation of malonylated pigments at the base of ray floret petals, positively regulated by three paralogous R2R3‐MYB transcription factors. Our results indicate that the functional diversification of these GdMYBSG6s involved changes in the spatial control of their transcription, and modification of the duration of GdMYBSG6 gene expression contributes towards floral variation within the species. [ABSTRACT FROM AUTHOR]

Cyanidin, peonidin and cyanidin-3-galactoside are the common anthocyanins with a variety of biological activities. Tyrosinase is a speed-limiting enzyme associated with melanin production. The inhibition of tyrosinase activity can prevent melanin disease while contributing to whitening. The interaction behaviors of the three anthocyanins against tyrosinase have been discussed in this paper. Cyanidin has strongest inhibitory effect on tyrosinase, and then peonidin, cyanidin-3-galactoside. Furthermore, the inhibition of tyrosinase by the three anthocyanins is mixed modes. The three anthocyanins can induce the static fluorescence quenching of tyrosinase. Cyanidin exhibits strongest binding affinity on tyrosinase, and then peonidin, cyanidin-3-galactoside based on Ka values obtain by fluorescence analysis. The binding of all anthocyanin to tyrosinase induce its conformation changes. According to molecular docking and fluorescence studies, they bind to tyrosinase by hydrogen bond and van der Waals force. In addition, the optimal modes of the three anthocyanins with tyrosinase are predicated by molecular docking. This work emphasizes that cyanidin, peonidin and cyanidin-3-galactoside may be potential drugs for the treatment of diseases caused by melanin. [ABSTRACT FROM AUTHOR]

Pyracantha is a genus of wild perennial shrubs native in an area extending from Southwest Europe to Southeast Asia, and it is used in traditional medicine for the diuretic, cardiac, and tonic properties of its fruits, which can also be cooked to make jellies, jams, and sauces. This work aims to study and compare the antioxidant activity and the phenolic and anthocyanin composition of three varieties of Pyracantha coccinea: Red Column (PCR), Orange Glow (PCO), and Soleil d'Or (PCS), and one of Pyracantha angustifolia: Orange glow (PAO), collected from the spontaneous flora of the Mediterranean region (Southern Italy). Two different extraction processes were tested using methanol and an aqueous methanol solution (80% MeOH) to evaluate the polyphenolic content and antioxidant activity of freeze-dried berries. The highest total phenolic content was found in PCR and PAO berries (174.21 ± 0.149 and 168.01 ± 0.691 mg of gallic acid equivalent per gram of dry matter, respectively) extracted with an aqueous methanol solution (80% MeOH). Polyphenolic extracts analyzed by HPLC-DAD-ESI/MS confirmed the presence of rutin, quercetin hexose, neoeriocitrin, procyanidin B, and resveratrol. Moreover, the total antioxidant activity of the berries' extracts was measured by comparing two different spectrophotometric methods (ABTS and DPPH), showing that the varieties with the highest total phenolic content, PCR and PAO, also had the highest scavenging activity. Finally, a suitable extraction process was chosen for the evaluation of the anthocyanins' composition of all frozen berries, and in all MS spectra of Pyracantha varieties, two ionic species at 449 m/z attributable to two cyanidin derivatives were found. [ABSTRACT FROM AUTHOR]

AimThe study aimed to explore the relationship of anthocyanin and its subtypes with myopia in adolescents aged 12–17 years.MethodsAdolescents data for this cross-sectional study were extracted from the National Health and Nutrition Examination Survey (NHANES) 2007–2008. Anthocyanin and subtypes were obtained using the Nutrient Database for Dietary Studies codes. Myopia was defined as a spherical equivalent of −1.0 diopters or less. The relationships between anthocyanin and subtypes intake and myopia were determined utilizing weighted univariate and multivariate logistic regression models. The relationships were also explored in gender, leisure time, physical activity, sedentary activity, BMI, and serum cotinine subgroups.ResultsA total of 839 adolescents were included for further analysis, among them 245 have myopia. Malvidin (34.98%) was the subtype with the largest anthocyanin intake, followed by cyanidin (22.94%). Compared to adolescents without anthocyanin intake, total anthocyanin intake was related to a lower incidence of myopia (OR = 0.69, 95%CI: 0.51–0.92). Higher intake of cyanidin (OR = 0.69, 95%CI: 0.52–0.92), petunidin (OR = 0.64, 95%CI: 0.42–0.97), and delphinidin (OR = 0.71, 95%CI: 0.51–0.99) were associated with lower odds of myopia in adolescents. Higher total anthocyanin intake was related to lower odds of myopia in those females, leisure time physical activity ≥60 min/day, sedentary time

The instability of anthocyanins significantly reduces their bioavailability as food nutrients. This proof-of-concept study aimed to develop efficient carriers for anthocyanins to overcome this challenge. Characterization of the hydrogels via SEM (scanning electron microscope) and rheological analysis revealed the formation of typical gel structures. MTT (methyl thiazolyl tetrazolium) and hemolysis assays confirmed that their high biocompatibility. Encapsulation efficiency analysis and fluorescence microscopy images demonstrated successful and efficient encapsulation of anthocyanins by pH-responsive hydrogels. Stability studies further validated the effect of peptide hydrogels in helping anthocyanin molecules withstand factors such as gastric acid, high temperatures, and heavy metals. Subsequently, responsive studies in simulated gastric (intestinal) fluid demonstrated that the pH-responsive peptide hydrogels could protect anthocyanin molecules from gastric acid while achieving rapid and complete release in intestinal fluid environments. These results indicate that these peptide hydrogels could stabilize anthocyanins and facilitate their controlled release, potentially leading to personalized delivery systems.

Although some species that accumulate only cyanidin (Cy) in nature can produce blue flowers through iron ions, there has been no evidence of blue chrysanthemums being generated in this manner. This study revealed that flavonoid extracts from the ray florets of the chrysanthemum cultivar ‘Wandai Fengguang’ turned blue when exposed to Fe3+. Samples that could turn blue were labeled as CB (Cy-determined blue flowers), while samples that did not turn blue were labeled as CN (Cy-determined non-blue flowers). After a series of experiments, a stable screening system was established using flavonoid extracts containing NaAc buffer at pH 5.5 and a total anthocyanin concentration (TAC) of 30 μmol·L−1, and the addition of Fe3+ from 0 to 0.25 μmol·L−1 allowed for the selection of five CB samples from 39 chrysanthemum cultivars. All five CB samples exhibited flower color phenotypes that belonged to Cluster-I with redness (a∗) values ranging from 29.03 to 45.99, yellowness (b∗) values from −11.31 to 3.77, and brightness (L∗) values from 29.07 to 45.99. Additionally, the ratio of TAC to total luteolin concentration (TLC) was found to be a critical factor for distinguishing between CB and CN samples. To realize the desired blue hue in the flavonoid extracts with the participation of Fe3+, a TAC to TLC ratio of 2.25 and above is required. Moreover, the protoplasts and ray florets of CB samples that turned blue with the involvement of Fe2+ showed great potential for cultivating blue chrysanthemums through ferric–anthocyanin chelate. Overall, this study reveals that blue flowers can be cultivated through the increase in the iron ion concentration, combined with the accumulation of Cy.

Polycyclic aromatic hydrocarbons (PAHs) form an important group of organic pollutants due to their distribution in the environment and their carcinogenic and/or mutagenic effects. In order to identify at the molecular level some of the players in the biodegradation and tolerance response to PAHs in plants, we have phenotyped 32 Arabidopsis thaliana T-DNA mutant lines corresponding to 16 cytochrome P450 (CYP) genes that showed to be differentially expressed under contrasted stress conditions induced by phenanthrene, a 3-ring PAH. This screening has allowed us to identify CYP75B1 (At5g07990) T-DNA mutants as the only ones being sensitive to phenanthrene-induced stress, supporting that CYP75B1 protein is necessary for PAH tolerance. CYP75B1 codes for a 3′flavonol hydroxylase. CYP75B1 gene was heterologously expressed on yeast in order to investigate whether it affects the A. thaliana response to phenanthrene by participating in its metabolization. Heterologously-produced CYP75B1 enzyme shows to be catalytically efficient against its physiological substrates (e.g., naringenin) but unable to metabolize phenanthrene or 9-phenanthrenol. In contrast, CYP75B1 seems rather involved in phenanthrene tolerance as a crucial element by regulating concentration of antioxidants through the production of 3′-hydroxylated flavonoids such as quercetin and cyanidin. In particular, we report a highly increased generation of reactive oxygen species (H2O2 and singlet oxygen) in cyp75b1 mutants compared to control plants in response to phenanthrene treatment. Overall, CYP75B1 shows to play an important role in the response to the deleterious effects of phenanthrene exposure and this is related to oxidative stress sensitivity rather than metabolization. [ABSTRACT FROM AUTHOR]

This study verified the in vitro activity of red cabbage and beetroot against the formation of advanced glycation end-products (AGEs) and their relationship with the biomolecules' content. Fermentation of cabbage increased the total phenolic (~10%) and flavonoid contents (~14%), whereas decreased total phenolics/flavonoids in beetroot. Fermented cabbage exhibited higher ability against AGEs, i.e., 17% in the bovine serum albumin–methylglyoxal (BSA-MGO) model and 25% in the BSA–glucose model, while beetroot exhibited 23% and 18%, respectively. The major compounds of cabbage products were cyanidin 3-(sinapoyl)(sinapoyl)-diglucoside-5-glucoside, sinapic acid, and epicatechin. Syringic acid and epicatechin were predominantly present in fermented beetroot. 2,17-bidecarboxy- and 2,15,17-tridecarboxy-betanin were the major betalains. Fermented vegetables can be effective inhibitors of the AGE formation/accumulation and could be recommended in the prevention of diet-related diseases. [ABSTRACT FROM AUTHOR]

In nature, hydrogen bonding is a common physical occurrence that has a significant impact on the surroundings of anthocyanins. Water molecules will create hydrogen bonds with anthocyanin molecules in various configurations, but the characteristics of these hydrogen bonds will change. Varied hydrogen bonding characteristics have varied impacts on solvent solutions. This research analyzes the differences in hydrogen bonding qualities caused by different methyl structures, as well as the underlying explanations. In this study, the cyanidin and peonidin structures of anthocyanin molecules were calculated in various stable hydrogen bond configurations using the density functional theory B3LYP/6‐31G(d,p), combined with information from the infrared spectroscopy spectrum, atoms in molecules analysis, interaction energy E, and intermolecular hydrogen bond length. The hydrogen bond structure that is the most stable is determined by analyzing it, as well as the effects of replacing the hydroxyl group with a methyl group and any potential underlying causes. Future anthocyanins research can benefit from the precise theoretical reference that this study can offer. [ABSTRACT FROM AUTHOR]

This study aimed to investigate the availability of flavonoids, anthocyanins, and phenolic acids in mutant bean seeds, focusing on M7 mutant lines, and their corresponding initial and local cultivars. HPLC-DAD-MS/MS and HPLC-MS/MS were used to analyze twenty-eight genotypes of common bean. The obtained results suggest that the mutations resulted in four newly synthesized anthocyanins in the mutant bean seeds, namely, delphinidin 3-O-glucoside, cyanidin 3-O-glucoside, pelargonidin 3-O-glucoside, and petunidin 3-O-glucoside, in 20 accessions with colored seed shapes out of the total of 28. Importantly, the initial cultivar with white seeds, as well as the mutant white seeds, did not contain anthocyanins. The mutant lines were classified into groups based on their colors as novel qualitative characteristics. Five phenolic acids were further quantified: ferulic, p-coumaric, caffeic, sinapic, and traces of chlorogenic acids. Flavonoids were represented by epicatechin, quercetin, and luteolin, and their concentrations in the mutant genotypes were several-fold superior compared to those of the initial cultivar. All mutant lines exhibited higher concentrations of phenolic acids and flavonoids. These findings contribute to the understanding of the genetics and biochemistry of phenolic accumulation and anthocyanin production in common bean seeds, which is relevant to health benefits and might have implications for common bean breeding programs and food security efforts. [ABSTRACT FROM AUTHOR]

The spines of Chinese red chestnut are red and the depth of their color gradually increases with maturity. To identify the anthocyanin types and synthesis pathways in red chestnut and to identify the key genes regulating the anthocyanin biosynthesis pathway, we obtained and analyzed the transcriptome and anthocyanin metabolism of red chestnut and its control variety with green spines at 3 different periods. GO and KEGG analyses revealed that photosynthesis was more highly enriched in green spines compared with red spines, while processes related to defense and metabolism regulation were more highly enriched in red spines. The analysis showed that the change in spine color promoted photoprotection in red chestnut, especially at the early growth stage, which resulted in the accumulation of differentially expressed genes involved in the defense metabolic pathway. The metabolome results revealed 6 anthocyanins in red spines. Moreover, red spines exhibited high levels of cyanidin, peonidin and pelargonidin and low levels of delphinidin, petunidin and malvidin. Compared with those in the control group, the levels of cyanidin, peonidin, pelargonidin and malvidin in red spines were significantly increased, indicating that the cyanidin and pelargonidin pathways were enriched in the synthesis of anthocyanins in red spines, whereas the delphinidin pathways were inhibited and mostly transformed into malvidin. During the process of flower pigment synthesis, the expression of the CHS, CHI, F3H, CYP75A, CYP75B1, DFR and ANS genes clearly increased, that of CYP73A decreased obviously, and that of PAL, 4CL and LAR both increased and decreased. Notably, the findings revealed that the synthesized anthocyanin can be converted into anthocyanidin or epicatechin. In red spines, the upregulation of BZ1 gene expression increases the corresponding anthocyanidin content, and the upregulation of the ANR gene also promotes the conversion of anthocyanin to epicatechin. The transcription factors involved in color formation included 4 WRKYs. [ABSTRACT FROM AUTHOR]

Pigmented rice, especially black rice, is gaining popularity as it is rich in antioxidants such as anthocyanins and γ-oryzanol. At present, knowledge about temporal control of biosynthesis and accumulation of antioxidants during grain development is limited. To address this, the accumulation patterns of anthocyanins and γ-oryzanol were assessed in two distinct black rice genotypes over the course of grain development, and the expression of known regulatory genes for anthocyanin biosynthesis was examined. The results indicated that total γ-oryzanol content increased continuously throughout grain development, while total anthocyanins peaked at dough stage (15 to 21 days after flowering) followed by a decline until grain maturity in both genotypes. However, the rate of decrease in anthocyanin content differed between genotypes, and a more prominent decline in cyanidin 3-O-glucoside (C3G) relative to peonidin 3-O-glucoside (P3G) was observed for both. Anthocyanin content was closely linked with the expression of key regulatory genes in the MBW (MYB-bHLH-WD40) complex. This improved knowledge of the genotype-specific biosynthesis (anthocyanins only) and accumulation patterns of anthocyanins and γ-oryzanol can inform subsequent research efforts to increase concentrations of these key antioxidants in black rice grains. [ABSTRACT FROM AUTHOR]

Currently the determination of cyanidin 3-rutinoside content in plant petals usually requires chemical assays or high performance liquid chromatography (HPLC), which are time-consuming and laborious. In this study, we aimed to develop a low-cost, high-throughput method to predict cyanidin 3-rutinoside content, and developed a cyanidin 3-rutinoside prediction model using nearinfrared (NIR) spectroscopy combined with partial least squares regression (PLSR). We collected spectral data from Michelia crassipes (Magnoliaceae) tepals and used five different preprocessing methods and four variable selection algorithms to calibrate the PLSR model to determine the best prediction model. The results showed that (1) the PLSR model built by combining the blockScale (BS) preprocessing method and the Significance multivariate correlation (sMC) algorithm performed the best; (2) The model has a reliable prediction ability, with a coefficient of determination (R2) of 0.72, a root mean square error (RMSE) of 1.04%, and a residual prediction deviation (RPD) of 2.06. The model can be effectively used to predict the cyanidin 3-rutinoside content of the perianth slices of M. crassipes, providing an efficient method for the rapid determination of cyanidin 3-rutinoside content. [ABSTRACT FROM AUTHOR]

Tea leaves are rich in diverse bioactive compounds. The tea accession TRI 2043 is unique due to its pigmented leaves caused by anthocyanins, clonal origin, resistance to blister blight disease, and high pubescence density. Because of its peculiarity, TRI 2043 is used to produce high-quality silver tip tea, a premium type of tea that commands high prices. This study was carried out to clarify and elucidate the types of anthocyanins in this particular accession. Four different anthocyanin species were identified and quantitated as cyanidin-3-O-β-d-galactoside and delphinidin-3-O-β-d-galactoside equivalents for leaf blades and stems of the cultivar TRI 2043. The characterization was performed by comparison with commercially available reference substances and further confirmed using ion mobility high-resolution time-of-flight-mass spectrometry (IMS-HRTOF-MS). Quantitation was carried out using ultra-high-performance liquid chromatography ultraviolet–visible detection (UHPLC-UV-vis) with cyanidin-3-O-β-d-glucoside as an internal standard. E- and Z-geometric isomers of 6-p-coumaroyl derivates of delphinidin and cyanidin-3-O-β-d-galactopyranosides were observed, and collision cross section (CCS) values were determined for all four different anthocyanidin species. The content of anthocyanins in leaf blades of cultivar TRI 2043 was 856.32 ± 41.56 µg/g dry weight, with cyanidin being the more abundant anthocyanin (69.8%). Conversely, the stem material contained an anthocyanin amount of 459.5 ± 44.7 µg/g dry weight, with a higher content of delphinidin (69.6%). In summary, an enrichment strategy using analytical membrane chromatography was established to fully elucidate and quantify the anthocyanin profile of plant samples such as the special tea variety TRI 2043. [ABSTRACT FROM AUTHOR]

Summary: Transient expression in Nicotiana benthamiana offers a robust platform for the rapid production of complex secondary metabolites. It has proven highly effective in helping identify genes associated with pathways responsible for synthesizing various valuable natural compounds. While this approach has seen considerable success, it has yet to be applied to uncovering genes involved in anthocyanin biosynthetic pathways. This is because only a single anthocyanin, delphinidin 3‐O‐rutinoside, can be produced in N. benthamiana by activation of anthocyanin biosynthesis using transcription factors. The production of other anthocyanins would necessitate the suppression of certain endogenous flavonoid biosynthesis genes while transiently expressing others. In this work, we present a series of tools for the reconstitution of anthocyanin biosynthetic pathways in N. benthamiana leaves. These tools include constructs for the expression or silencing of anthocyanin biosynthetic genes and a mutant N. benthamiana line generated using CRISPR. By infiltration of defined sets of constructs, the basic anthocyanins pelargonidin 3‐O‐glucoside, cyanidin 3‐O‐glucoside and delphinidin 3‐O‐glucoside could be obtained in high amounts in a few days. Additionally, co‐infiltration of supplementary pathway genes enabled the synthesis of more complex anthocyanins. These tools should be useful to identify genes involved in the biosynthesis of complex anthocyanins. They also make it possible to produce novel anthocyanins not found in nature. As an example, we reconstituted the pathway for biosynthesis of Arabidopsis anthocyanin A5, a cyanidin derivative and achieved the biosynthesis of the pelargonidin and delphinidin variants of A5, pelargonidin A5 and delphinidin A5. [ABSTRACT FROM AUTHOR]

Anthocyanins are colored water-soluble plant pigments. Upon consumption, anthocyanins are quickly absorbed and can penetrate the blood–brain barrier (BBB). Research based on population studies suggests that including anthocyanin-rich sources in the diet lowers the risk of neurodegenerative diseases. The copigmentation caused by copigments is considered an effective way to stabilize anthocyanins against adverse environmental conditions. This is attributed to the covalent and noncovalent interactions between colored forms of anthocyanins (flavylium ions and quinoidal bases) and colorless or pale-yellow organic molecules (copigments). The present work carried out a theoretical study of the copigmentation process between cyanidin and resveratrol (CINRES). We used three levels of density functional theory: M06-2x/6-31g+(d,p) (d3bj); ωB97X-D/6-31+(d,p); APFD/6-31+(d,p), implemented in the Gaussian16W package. In a vacuum, the CINRES was found at a copigmentation distance of 3.54 Å between cyanidin and resveratrol. In water, a binding free energy ∆G was calculated, rendering −3.31, −1.68, and −6.91 kcal/mol, at M06-2x/6-31g+(d,p) (d3bj), ωB97X-D/6-31+(d,p), and APFD/6-31+(d,p) levels of theory, respectively. A time-dependent density functional theory (TD-DFT) was used to calculate the UV spectra of the complexes and then compared to its parent molecules, resulting in a lower energy gap at forming complexes. Excited states' properties were analyzed with the ωB97X-D functional. Finally, Shannon aromaticity indices were calculated and isosurfaces of non-covalent interactions were evaluated. [ABSTRACT FROM AUTHOR]

Floral biochemistry and stress physiology is an underexplored aspect of mangroves, which should be investigated as part of preservation and restoration efforts. A thriving true mangrove tree (Bruguiera gymnorrhiza (L.) Lamk.) and a threatened mangrove-associate species (Heritiera fomes Buch. Ham.) were studied in the Sundarban region of India for seasonal variations in floral odours, non-volatile phytochemicals, antioxidant enzyme activities, and surface water chemistry in surrounding habitat. Both species were found to exhibit significant differences in floral volatilomes, protein contents, antioxidant enzyme activities, total flavonoids, and total phenolic contents between spring and autumn blooms. The bird-pollinated flowers of B. gymnorrhiza also showed considerable seasonal differences in floral anthocyanin and proline contents, indicating vulnerability of the post-anthesis open flowers to environmental factors. Contrarily to previous findings, B. gymnorrhiza floral bouquet appeared to be enriched in various classes of volatiles – dominated by sulphurous compounds in bud stage and terpenoids in open stage. Floral anthocyanins, contributing to the striking colouration of the calyx, were found to comprise cyanidin and delphinidin derivatives. Other glycosides of cyanidin and delphinidin were detected in H. fomes flowers, contributing to visual guides to potential food rewards for pollinating insects. Floral tissue in H. fomes was found to be protected by densely overlapping layers of stellate trichomes containing sesquiterpenoids as phytoprotectants. Comparison of the two floral species suggested that H. fomes flowering is optimized to oligohaline (but not freshwater) vernal conditions; whereas B. gymnorrhiza blooms are adapted for biologically enriched (including abundant herbivores and microbial growth), mesohaline forest habitats. [ABSTRACT FROM AUTHOR]

Cyanidin 3-O-glucoside (C3G) is believed to combine with oral mucin, thus impairing oral lubrication and leading to the development of oral astringency. When C3G is oxidized into cyanidin 3-O-glucoside quinone (C3GQ), it might covalently interact with cysteine of mucin to enhance astringency. Herein, their detailed interactions at the molecule level were characterized through spectroscopy, isothermal titration calorimetry and determination of free amino and sulfhydryl groups. The results showed that hydrogen bond and van der Waals force were the predominant non-covalent interactions. Furthermore, C3GQ could additionally bind to mucin by forming C-N and C-S bonds since the amino and sulfhydryl groups of mucin decreased by 0.48 mmol/g and 4.14 µmol/g after reacting with C3GQ. Besides, C3GQ had stronger interaction with mucin as the exothermic value of Muc-C3GQ (2513 KJ/mol) was larger than Muc-C3G (60.4 KJ/mol). These findings may explain the phenomenon of increased astringency of anthocyanins after being oxidized into quinones. [ABSTRACT FROM AUTHOR]

This study analyzed the anthocyanin content and antioxidant properties of five mulberry (Morus spp.) varieties, including black (M. nigra), red (M. rubra) and white (M. alba) types. Anthocyanins were extracted and analyzed using HPLC–MS, which revealed four major pigments: cyanidin-3-glucoside, cyanidin-3-rutinoside, cyanidin-3,5-diglucoside and pelargonidin-3-glucoside. Total anthocyanins were significantly higher in black mulberries Bom irangi (185 mg/100 g) and Kalmi (158 mg/100 g) compared to 28–60 mg/100 g in other varieties, consistent with their dark fruit color. Electrochemical analysis by cyclic voltammetry showed oxidation peak potentials (Epa) of key anthocyanins: + 368 mV for cyanidin; + 830 mV for cyanidin-3-glucoside; and + 912 mV for pelargonidin-3-glucoside. Lower Epa indicates easier oxidation and greater antioxidant activity. DPPH radical scavenging assays revealed strongest potency for Bom irangi (EC50 42 μg/mL) and Kalmi (EC50 58 μg/mL), again due to high anthocyanin levels. Further, a negative correlation (R2 = 0.923) was demonstrated between Epa values and EC50, proving excellent predictive ability of electrochemical data for estimating antioxidant capacity. Cyanidin with lowest Epa (+ 368 mV) and highest hydroxylation exhibited strongest activity (EC50 35 μg/mL). Overall, the study successfully demonstrated the antioxidant potential of mulberry anthocyanins, especially from black varieties, using advanced analytical strategies. [ABSTRACT FROM AUTHOR]

The anthocyanin compound cyanidin 3-O-glucoside (C3G) is a natural pigment widely used in food and nutraceutical industries. Its microbial synthesis by E. coli is a promising alternative to the traditional extraction methods. However, part of the synthesized C3G accumulates in the cytoplasm, thus potentially causing growth inhibition and product degradation. Therefore, it is necessary to enhance C3G secretion via exploration of native transporters facilitating C3G export. In this study, we report the screening and verification of native multidrug resistance transporters from 40 candidates in E. coli that can improve the extracellular C3G production when using catechin as the substrate. Overexpression of single transporter genes including fsr, yebQ, ynfM, mdlAB, and emrKY were found to increase C3G production by 0.5-to 4.8-fold. Genetic studies indicated that mdlAB and emrKY are vital transporters in the secretion of C3G. Our study reveals a set of new multidrug resistance transporters for the improvement of microbial biosynthesis of C3G and other anthocyanins. [ABSTRACT FROM AUTHOR]

Natural phytochemicals are well known to protect against numerous metabolic disorders. Anthocyanins are vacuolar pigments belonging to the parent class of flavonoids. They are well known for their potent antioxidant and gut microbiome-modulating properties, primarily responsible for minimizing the risk of cardiovascular diseases, diabetes, obesity, neurodegenerative diseases, cancer, and several other diseases associated with metabolic syndromes. Berries are the primary source of anthocyanin in the diet. The color and stability of anthocyanins are substantially influenced by external environmental conditions, constraining their applications in foods. Furthermore, the significantly low bioavailability of anthocyanins greatly diminishes the extent of the actual health benefits linked to these bioactive compounds. Multiple strategies have been successfully developed and utilized to enhance the stability and bioavailability of anthocyanins. This review provides a comprehensive view of the recent advancements in chemistry, biosynthesis, dietary sources, stabilization, bioavailability, industrial applications, and health benefits of anthocyanins. Finally, we summarize the prospects and challenges of applications of anthocyanin in foods. [ABSTRACT FROM AUTHOR]

The present study aims to highlight the cell protective effect of Tropea red onion (TRO) hydroalcoholic extract and some of its components against "non-essential" heavy metals. For this purpose, the cytoprotective roles of cyanidin, cyanidin-3-O-glucoside and quercetin against Cd, Hg and Pb and of TRO extract against Hg and Pb have been investigated, and data are reported here. To the best of our knowledge, this is the first detailed evaluation of the protective effect against cell damage induced by "non-essential" heavy metals through the simultaneous administration of cyanidin, cyanidin-3-O-glucoside and quercetin with CdCl2, HgCl2 or PbCl2 and the TRO extract against HgCl2 and PbCl2. Present data are also compared with our previous results from the TRO extract against Cd. The antioxidant capacity of the extract was also determined by the ferric reducing antioxidant power (FRAP) and the bovine brain peroxidation assay. Both of the assays indicated a good antioxidant capacity of the extract. Cell viability and the impact on necrotic cell death were examined by the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) test and lactate dehydrogenase (LDH) release assay. After 24 h of exposure, Caco-2 cell viability decreased by approximately 50% at 0.25 μM for Cd, Hg and Pb and, after 72 h, the ranking order of "non-essential" heavy metal toxicity on cell viability was PbCl2 > CdCl2 > HgCl2. Cell viability was assessed by treating the cells with the biomolecules at doses of 25, 50 and 100 µg/mL for 24 and 72 h. The same analysis was carried out on Caco-2 cells treated with combinations of TRO extract, cyanidin, cyanidin-3-O-glucoside, or quercetin and "non-essential" heavy metals. Treatments with the bioactive metabolites did not significantly improve cell viability. The identical treatment of Caco-2 cells produced instead LDH release, suggesting a decrease in cell viability. Consistently with the finding that TRO extract showed a good antioxidant activity, we suggest that its higher cytotoxicity, compared to that of the individual assayed phytochemicals, may be derived by the combined antioxidant and chelating properties of all the molecules present in the extract. Therefore, from all the acquired experimental evidence, it appears that the TRO extract may be a better promising protective agent against the toxic effect of Cd, Hg and Pb compared to its bioactive metabolites. [ABSTRACT FROM AUTHOR]