Floral pigments and their perception by avian pollinators in three Chilean Puya species.

The Chilean Puya species, Puya coerulea var. violacea and P. chilensis bear blue and pale-yellow flowers, respectively, while P. alpestris considered to be their hybrid-derived species has unique turquoise flowers. In this study, the chemical basis underlying the different coloration of the three Puya species was explored. We first isolated and identified three anthocyanins: delphinidin 3,3',5'-tri-O-glucoside, delphinidin 3,3'-di-O-glucoside and delphinidin 3-O-glucoside; seven flavonols: quercetin 3-O-rutinoside-3'-O-glucoside, quercetin 3,3'-di-O-glucoside, quercetin 3-O-rutinoside, isorhamnetin 3-O-rutinoside, myricetin 3,3',5'-tri-O-glucoside, myricetin 3,3'-di-O-glucoside and laricitrin 3,5'-di-O-glucoside; and six flavones: luteolin 4'-O-glucoside, apigenin 4'-O-glucoside, tricetin 4'-O-glucoside, tricetin 3',5'-di-O-glucoside, tricetin 3'-O-glucoside and selagin 5'-O-glucoside, which is a previously undescribed flavone, from their petals. We also compared compositions of floral flavonoid and their aglycone among these species, which suggested that the turquoise species P. alpestris has an essentially intermediate composition between the blue and pale-yellow species. The vacuolar pH was relatively higher in the turquoise (pH 6.2) and pale-yellow (pH 6.2) flower species, while that of blue flower species was usual (pH 5.2). The flower color was reconstructed in vitro using isolated anthocyanin, flavonol and flavone at neutral and acidic pH, and its color was analyzed by reflectance spectra and the visual modeling of their avian pollinators. The modeling demonstrated that the higher pH of the turquoise and pale-yellow species enhances the chromatic contrast and spectral purity. The precise regulation of flower color by flavonoid composition and vacuolar pH may be adapted to the visual perception of their avian pollinator vision.

Progress on molecular modification and functional applications of anthocyanins.

Anthocyanins have attracted a lot of attention in the fields of natural pigments, food packaging, and functional foods due to their color, antioxidant, and nutraceutical properties. However, the poor chemical stability and low bioavailability of anthocyanins currently limit their application in the food industry. Various methods can be used to modify the structure of anthocyanins and thus improve their stability and bioavailability characteristics under food processing, storage, and gastrointestinal conditions. This paper aims to review in vitro modification methods for altering the molecular structure of anthocyanins, as well as their resulting improved properties such as color, stability, solubility, and antioxidant properties, and functional applications as pigments, sensors and functional foods. In industrial production, by mixing co-pigments with anthocyanins in food systems, the color and stability of anthocyanins can be improved by using non-covalent co-pigmentation. By acylation of fatty acids and aromatic acids with anthocyanins before incorporation into food systems, the surface activity of anthocyanins can be activated and their antioxidant and bioactivity can be improved. Various other chemical modification methods, such as methylation, glycosylation, and the formation of pyranoanthocyanins, can also be utilized to tailor the molecular properties of anthocyanins expanding their range of applications in the food industry.

Recent advances in the research and development of blue flowers.

Flower color is the most important trait in the breeding of ornamental plants. In the floriculture industry, however, bluish colored flowers of desirable plants have proved difficult to breed. Many ornamental plants with a high production volume, such as rose and chrysanthemum, lack the key genes for producing the blue delphinidin pigment or do not have an intracellular environment suitable for developing blue color. Recently, it has become possible to incorporate a blue flower color trait through progress in molecular biological analysis of pigment biosynthesis genes and genetic engineering. For example, introduction of the F3'5'H gene encoding flavonoid 3',5'-hydroxylase can produce delphinidin in various flowers such as roses and carnations, turning the flower color purple or violet. Furthermore, the world's first blue chrysanthemum was recently produced by introducing the A3'5'GT gene encoding anthocyanin 3',5'-O-glucosyltransferase, in addition to F3'5'H, into the host plant. The B-ring glucosylated delphinidin-based anthocyanin that is synthesized by the two transgenes develops blue coloration by co-pigmentation with colorless flavone glycosides naturally present in the ray floret of chrysanthemum. This review focuses on the biotechnological efforts to develop blue flowers, and describes future prospects for blue flower breeding and commercialization.

Dynamic changes of anthocyanins during 'Ziyan' tea wine processing.

In this study, the dynamic changes of different anthocyanins in the processing of 'Ziyan' tea wine were investigated quantitatively. Results showed that six types of anthocyanins, namely petunidin, malvidin, pelargonidin, delphinidin, cyanidin and peonidin, as well as two co-pigmented substances, procyanidins and flavonoids, were detected in 'Ziyan' tea wine. As fermentation proceeded, the contents of petunidin, pelargonidin, delphinidin, cyanidin and peonidin decreased. Among them, petunidin, peonidin and pelargonidin showed a tendency of decreasing first, then increasing and finally decreasing, whereas delphinidin and cyanidin continued to decrease during fermentation. Variation trend of procyanidins and flavonoids was consistent with those of petunidin. Furthermore, metabolism of delphinidin, cyanidin and pelargonidin were main pathways responsible for the anthocyanin changes during 'Ziyan' tea wine processing. These findings suggested that the color of 'Ziyan' tea wine was achieved by the combination of various anthocyanins in different ratios and the co-pigmentation of procyanidins and flavonoids.

Preparation of multifunctional hydrogels based on co-pigment-polysaccharide complexes and establishment of a machine learning monitoring platform.

Economic loss due to fish spoilage exceeds 25 billion euros every year. Accurate and real-time monitoring of the freshness of fish can effectively cut down economic loss and food wastage. In this study, a dual-functional hydrogel based on sodium alginate-co-pigment complex with volatile antibacterial and intelligent indication was prepared and characterized. The characterization results indicated that the sodium alginate-co-pigment complex successfully improved the stability and color development ability of blueberry anthocyanins and bilberry anthocyanins at different temperatures and pH. The double cross-linking network inside the hydrogel conferred it with excellent mechanical properties. During rainbow trout storage, the hydrogel indicated a color difference of 73.55 on the last day and successfully extended the shelf-life of rainbow trout by 2 days (4 °C). Additionally, four dual-channel monitoring models were constructed using machine learning. The validation error of the genetic algorithm back propagation model (GA-BP) was only 5.6e-3, indicating that GA-BP can accurately monitor the freshness of rainbow trout. The rainbow trout real-time monitoring platform built based on GA-BP model can monitor the freshness of rainbow trout in real time through the images uploaded by users. The results of this study have broad applicability in the food industry, environmental conservation, and economic sustainability.

Anthocyanin modified by chondroitin sulphate and tannic acid improved the quality-indicating properties of gelatin-based intelligent film.

A highly pH-responsive gelatin film incorporating purple cabbage anthocyanin (PCA) and chondroitin sulphate (CS)/tannic acid (TA) was developed. Co-pigmentation of PCA via CS/TA improved its photothermal stability and visibility of color change in gelatin film. The morphological and structural properties of CS-PCA and TA-PCA films revealed that a more stable network was formed as new hydrogen bonds were generated by the co-pigmentation. Meanwhile, the co-pigmentation improved film's mechanical and hydrophobic properties, expressed as higher tensile strength (16.65 and 17.97 Mpa) and lower water vapor permeability (1.45 and 1.41) in CS-PCA and TA-PCA films, compared to PCA film. CS-PCA and TA-PCA films showed distinct color transitions for chilled fish fillets during storage. Total color difference (ΔE) of CS-PCA and TA-PCA films correlated well with the deterioration indexes of total volatile base nitrogen (TVB-N). All the results provided a novel pH-sensitive intelligent packaging strategy by co-pigmenting CS/TA with PCA for freshness monitoring.

Dietary Sources, Stabilization, Health Benefits, and Industrial Application of Anthocyanins-A Review.

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.

A colorimetry-enhanced tri-functional film with high stability by polyphenol-anthocyanin co-pigmentation/conjugate: New prospect for active intelligent food packaging.

A highly stable "tannin-anthocyanin conjugated" trifunctional active intelligent film was developed by incorporating bilberry anthocyanins (BA) as an indicator and tannin acids (TA) as a co-pigment into a sodium alginate-carrageenan polysaccharide matrix (SC-BA/TA). The doping of TA conferred outstanding antioxidant (DPPH scavenging rate > 90%) and antibacterial properties to the film, particularly effective against S. aureus. The SC-BA/TA films effectively blocked UV rays (close to 0%, effectively impeding most UVA, as well as nearly all UVC and UVB) within the range of 200-320 nm. The TA-BA co-pigment effect significantly improved the anthocyanins' storage and color stability (retention rate > 70% under UV and natural light conditions). TA forms conjugate with anthocyanins by π-π stacking and hydrogen bonding interactions with co-pigmentation rate increases of 10.5% and 11.0% for pH 2 and pH 3, respectively. The film exhibited good responsiveness to volatile amines within 4 min, and offered real-time monitoring of beef freshness, as indicated by visualizing color changes (from red to dark yellow color). Furthermore, the integration of the film's RGB value with beef quality via a smartphone App effectively reduces the variability in visual recognition among individuals. To sum up, composite films based on the "tannin-anthocyanin conjugate" approach hold great potential in the field of food freshness monitoring, opening new possibilities for the development of highly stable active smart packaging films.

A double-layer film based on the strategy of tannic acid-anthocyanin co-pigmentation and tannic-crosslinked-gelatin/-reduced Ag nanoparticles for beef preservation and monitoring.

A double-layer film was developed with tannic acid (TA) co-pigmented purple potato anthocyanin extract (PAE)-agar as the inner layer, and K-carrageenan-oregano essential oil Pickering emulsion (OPE)/silver nanoparticles (TA-AgNPs) as the outer layer. Molecular docking and FT-IR results elucidated that intermolecular hydrogen bond was the main interaction between components in the agar-carrageenan matrix, with TA and PAE contributing to intensified anthocyanin color through π-π stacking. The incorporation of OPE/TA-AgNPs enhanced the film's hydrophobicity (WCA > 100°) and UV-vis barrier (close to 0% at 200-320 nm, effectively impeding UVA, UVB, and UVC) properties and exhibited outstanding antioxidant (DPPH scavenging rate > 88%) and antimicrobial activities. This film showed a significant color change in the pH range of 2-12 (from pink to yellow) and a considerable sensitivity to volatile amines within 2 min. The films effectively alleviated beef spoilage (extending the shelf life of beef for 1d) and reflected the freshness of beef during storage. Additionally, the digital color information of the film was obtained by a smartphone combined with RGB values analysis to quantify the freshness of beef rapidly. Therefore, this study expands the application of food packaging films with freshness preservation and monitoring in the field of animal-derived food.

Dye stability of black cherry plum anthocyanins in the interaction with co-pigments and sucrose sweetener.

In this research, the co-pigmentation reactions between black cherry plum (Prunus cerasifera Ehrh. cv. Pissardii Nigra) anthocyanins and caffeic, gallic, 4-hydroxybenzoic, malic, and tannic acids with different concentrations (0, 120, 240, 480, and 960 mg L-1) at various temperatures (20, 40, 60, 80, and 100°C) were investigated at pH 3.5. The strongest immediate co-pigmentations resulted at 960 mg L-1, being significantly highest using tannic acid at all temperatures. In addition, the anthocyanin stability and the brown polymeric color formation were investigated in the presence of different concentrations of sucrose sweetener (0, 30, and 60%) and different pHs (2 and 3) in the range of 0-60 h. Also, the amount of furfural was measured in the presence of 0% and 30% sucrose concentrations at pH 2 after 20 h at 90°C by HPLC (high-performance liquid chromatography), and the most polymeric color formation was observed in the concentration of 60% sucrose at pH 2 after 60 h.

Kombucha analogs from maqui juice: Consortium age and sugar concentration effects on anthocyanin stability and its relationship with antioxidant activity and digestive enzyme inhibition.

The fermentation of maqui juice (MJ), by incorporating kombucha as a starter culture, produces beverages with variable and stable anthocyanin contents. The metabolic effect of kombucha starter cultures obtained at different fermentation times was explored on the anthocyanin stability of maqui (Aristotelia chilensis (Mol.) Stuntz) juice supplemented at different concentrations of sucrose and fermented at different times. The stability of anthocyanins was associated with the levels of catechin detected in the fermentation system. This study concludes that the fermentation of MJ with sucrose (10%) and kombucha consortium of 7-days old, promotes the release and accumulation of phenolic compounds that act as co-pigments, with the best response in quality parameters of beverages such as color intensity, tone, hyperchromic effect, and a significant bathochromic shift. Finally, the additive effect of phenolic constituents with stable anthocyanins, confers to kombucha analogs an outstanding antioxidant quality and inhibitory effects on key enzymes in digestive processes.

Effect of co-pigments on anthocyanins of Rhododendron arboreum and insights into interaction mechanism.

The impact of intermolecular copigmentation between five phenolic acids, two flavonoid and three amino acids with R. arboreum anthocyanins (ANS) and its isolated cyanidin-3-O-monoglycosides were investigated through experimental and theoretical approach. On addition of different copigments, phenolic acid induced strong hyperchromic (0.26-0.55 nm) and bathochromic shift (6.6-14.2 nm). The color intensity and stability of ANS with, storage at 4 °C & 25 °C, sunlight, oxidation and heat were evaluated by chromaticity, anthocyanin content, kinetic and structural simulation analysis. The strongest copigmentation reaction was observed with narningin (NA) and also showed high thermostability and highest half-life i.e. 3.39 h-1.24 h at 90-160 °C. The cyanidin-3-O-monoglycosides were analysed for their copigmentation effect and observations revealed that NA displayed best copigmentation effect to cyanidin-3-O-arabinoside (B) followed by cyanidin-3-O-galactoside (A), and cyanidin-3-O-rhamnoside (C). Additionally, structural simulation and steered molecular dynamics insights NA is the most favourable co-pigment involving π-π stacking and H-bonding.

The highly stable indicator film incorporating roselle anthocyanin co-pigmented with oxalic acid: Preparation, characterization and freshness monitoring application.

A novel stable PVA/HPMC/roselle anthocyanin (RAE) indicator film co-pigmented with oxalic acid (OA) was prepared, its properties, application effects and stability enhancement mechanism were investigated correspondingly. The structural characterization revealed that more stable network was formed due to the co-pigmentation facilitated generation of molecular interactions. Meanwhile, the co-pigmentation improved film mechanical and hydrophobic properties compared to both PVA/HPMC/RAE newly prepared (PHRN) or stored (PHRS) film, expressing as higher tensile strength values (12.25% and 14.44% higher than PHRN and PHRS), lower water solubility (7.22% and 10.09% lower than PHRN and PHRS) and water vapor permeability values (33.20% and 21.05% lower than PHRN and PHRS) of PVA/HPMC/RAE/OA newly prepared (PHON) or stored (PHOS) film. Compared with the PHRS film, the PHOS film still presented more distinguishable color variations when being applied to monitor shrimp freshness, owing to the stabilization behaviors of co-pigmentation in anthocyanin conformation. Hence, the co-pigmentation was an effective strategy to enhance film stability, physical and pH-responsive properties after long term storage, leading to better film monitoring effects when applied in real-time freshness monitoring.

Improved thermal stability of roselle anthocyanin by co-pigmented with oxalic acid: Preparation, characterization and enhancement mechanism.

The enhancement effects of co-pigmentation on thermal stability of roselle anthocyanin extract (RAE) were investigated. The introduction of organic acids maintained color stability of RAE, and RAE co-pigmented with oxalic acid (OA) presented less color fading rates (19.46 ± 0.33 %) and higher redness (41.33 ± 3.51). Subsequently, suitable co-pigmentation concentration (OA:RAE = 1:2) was obtained regarding with lower ΔE (48.70 ± 2.36). Then, improvement behaviors of co-pigmentation on OA-RAE were evaluated. Results demonstrated that OA-RAE exhibited better thermal stability, as manifested by larger retention rates and more favorable thermal degradation kinetic parameters. Furthermore, both molecular docking simulation and experimental structural characterization revealed that hydrogen bonds and other non-covalent bonds made up the main parts of molecular interactions, leading to formation of stable binary complex. As a result, the aromatic ring of RAE was protected. In conclusion, the co-pigmentation of RAE via introduction of OA was effective in stability enhancement due to the generation of molecular bindings.

Investigation of the difference in color enhancement effect on cyanidin-3-O-glucoside by phenolic acids and the interaction mechanism.

Co-pigmentation effect of phenolic acids on cyanidin-3-O-glucoside (C3G) and the mechanisms were investigated. Sinapic acid (SIA), ferulic acid (FA), p-coumaric acid (p-CA) and syringic acid (SYA) significantly enhanced C3G stability (P < 0.05), whereas vanillic acid (VA) and gallic acid (GA) showed no influence (P > 0.05). Among these phenolic acids, SIA and FA had higher binding coefficient with C3G (48.83 and 43.38), reduced degradation rate constant by 40.0 âˆ¼ 50.0 %, prolonged half-life by 74.6 âˆ¼ 94.7 % at 323 K, and significantly inhibited C3G hydration reaction (pKh = 2.87 and 2.80, P < 0.05). Molecular docking revealed that C3G and co-pigments were connected by hydrogen bond and π-π stacking interaction. Hydroxycinnamic acids of SIA, FA and p-CA bound with ring B and ring C of C3G, while hydroxybenzoic acids of SYA, VA and GA hardly interacted with ring C. Generally, the protection effect of hydroxycinnamic acids on C3G was better than that of hydroxybenzoic acids, exhibiting stronger hyperchromic effect.

Development of Indicator Film Based on Cassava Starch-Chitosan Incorporated with Red Dragon Fruit Peel Anthocyanins-Gambier Catechins to Detect Banana Ripeness.

Banana ripeness is generally determined based on physical attributes, such as skin color; however, it is considered subjective because it depends on individual factors and lighting conditions. In addition, improper handling can cause mechanical damage to the fruit. Intelligent packaging in the form of indicator film incorporated with anthocyanins from red dragon fruit peel has been applied for shrimp freshness detection; however, this film has low color stability during storage, necessitating the addition of gambier catechins as a co-pigment to increase anthocyanin stability. Nevertheless, the characteristics of films that contain gambier catechins and their applications to bananas have not been studied yet; therefore, this study aims to develop and characterize indicator films that were incorporated with red dragon fruit peel anthocyanins and gambier catechins to detect banana ripeness. In this study, the indicator films were made via solvent casting. The films were characterized for their structural, mechanical, and physicochemical properties, and then applied to banana packaging. The results show that the film incorporated with anthocyanins and catechins in a ratio of 1:40 (w/w) resulted in better color stability, mechanical properties, light and water vapor barrier ability, and antioxidant activity. The application of the indicator films to banana packaging resulted in a change in color on the third day of storage. It can be concluded that these films could potentially be used as an indicator to monitor banana ripeness.

Effects of Ultrasound Irradiation on the Co-Pigmentation of the Added Caffeic Acid and the Coloration of the Cabernet Sauvignon Wine during Storage.

In this paper, experiments were conducted to investigate the effects of ultrasound irradiation on the co-pigmentation of caffeic acid added in wine and the coloration of wine during storage. The wine color, chroma, level of the monomeric, combined and polymerized anthocyanins and the concentrations of malvidin-3-O-glucoside and syringic acid in wines were determined by the high-performance liquid chromatography (HPLC), ultraviolet-visible spectroscopy, respectively. The results indicate that ultrasound irradiation could definitely affect the color characteristic of wine to a certain extent. Compared with the wine without addition of caffeic acid, the co-pigmentation effects of wine added with caffeic acid could be significantly promoted by ultrasound irradiation, such as the wine color, color density and the polymerized anthocyanins. Furthermore, ultrasound irradiation had a continuous effect on the co-pigmentation of caffeic acid and wine coloration with the extended storage time. In summary, ultrasound could significantly modify the color properties of wine by enhancing the co-pigmentation between caffeic acid and monomeric anthocyanins in the wine, resulting in the improvement of wine quality.

Effect of Soybean Protein Isolate-7s on Delphinidin-3-O-Glucoside from Purple Corn Stability and Their Interactional Characterization.

Anthocyanins are abundant in purple corn and beneficial to human health. Soybean protein isolate-7s (SPI-7s) could enhance the stability of anthocyanins. The stable system of soybean protein isolate-7s and delphinidin-3-O-glucoside complex (SPI-7s-D3G) was optimized using the Box-Behnken design at pH 2.8 and pH 6.8. Under the condition of pH 2.8, SPI-7s effectively improved the sunlight-thermal stabilities of delphinidin-3-O-glucoside (D3G). The thermal degradation of D3G conformed to the first order kinetics within 100 min, the negative enthalpy value and positive entropy value indicated that interaction was caused by electrostatic interaction, and the negative Gibbs free energy value reflected a spontaneous interaction between SPI-7s and D3G. The interaction of SPI-7s-D3G was evaluated by ultraviolet visible spectroscopy, circular dichroism spectroscopy and fluorescence spectroscopy. The results showed that the maximum absorption peak was redshifted with increasing the α-helix content and decreasing the ß-sheet contents, and D3G quenched the intrinsic fluorescence of SPI-7s by static quenching. There was one binding site in the SPI-7s and D3G stable system. The secondary structure of SPI-7s had changed and the complex was more stable. The stabilized SPI-7s-D3G will have broad application prospects in functional foods.

Prediction of Anthocyanin Color Stability against Iron Co-Pigmentation by Surface-Enhanced Raman Spectroscopy.

The color change resulting from anthocyanin and iron co-pigmentation has been a significant challenge for the food industry in the development of many iron-fortified foods. This present study aims to establish a quantitative model to predict the degree of color stability in the presence of dissolved iron using surface-enhanced Raman spectroscopic (SERS) spectra. The SERS spectra of anthocyanin extracts from seven different plant sources were measured and analyzed by principal component analysis (PCA). Discrimination among different sources of anthocyanin was observed in the PCA plot. Different stability indexes, obtained by measuring both the color intensity stability and color hue stability of each sample, were established based on UV-vis analysis of anthocyanin at pH 3 and 6 with and without ferric sulfate. Partial least square (PLS) regression models were applied to establish the correlation between SERS spectra and stability indexes. The best PLS model was built based on the stability index calculated from the bathochromic shift (UV-vis spectral range: 380-750 nm) in pH3 buffer and the SERS spectra, achieving a root mean square error of prediction (RMSEP) of 2.16 nm and a correlation coefficient value (R2) of 0.98. In conclusion, the present study developed a feasible approach to predict the stability of anthocyanin colorants against iron co-pigmentation. The developed method and models can be used for fast screenings of raw ingredients in iron-fortified food products.

A Case Study for the Extraction, Purification, and Co-Pigmentation of Anthocyanins from Aronia melanocarpa Juice Pomace.

Chokeberry (Aronia melanocarpa) pomace is a by-product from the juice industry very rich in anthocyanins and other bioactive components. Recovery and purification of anthocyanins from the pomace is a viable valorization strategy that can be implemented to produce high-value natural food colorants with antioxidant properties. In this study, chokeberry pomace was subjected to enzyme-assisted extraction using commercial pectinases. The extracts were further purified by adsorption-desorption using an acrylic resin and stabilized by co-pigmentation with ferulic acid. The anthocyanin concentration and antioxidant activity of the extracts were unaffected by the enzymatic treatment at the conditions tested. The total phenolic content of the extracts suffered minor variations depending on the enzyme formulation used, whereas the dissolved solid content increased in all cases. The adsorption-desorption strategy allowed a 96% recovery of the anthocyanins initially present in the extract, whereas the co-pigmentation treatment magnified the intensity of the color in terms of absorbance, and improved the stability during storage up to one month.