Pectin forms polymeric pigments by complexing anthocyanins during red winemaking and ageing.

The long-term stability of red wine color depends on the formation of polymeric pigments from anthocyanins. Although there is still a lot of uncertainty about the specific structure of this diverse group of pigments, there is consensus that they are reaction products of anthocyanins and other polyphenols. Interactions between anthocyanins and pectic polysaccharides have been suggested to stabilize anthocyanins. This study explores the impact of such interactions by adding pectin during red winemaking. The results demonstrate that these interactions induce the formation of additional polymeric pigments which enhance the pigment stability during fermentation and aging. While initial pigment formation is higher in wines with added pectin, a notable proportion of the complexes degrades in the later stages of fermentation. Presumably, tannins form insoluble complexes with pectin, reducing tannin concentration by more than 300 mg/L. Anthocyanin concentrations decrease by over 400 mg/L, and polymeric pigments double. Anthocyanins that form polymeric pigments with pectic polysaccharides expand the range of pigments in red wines with possible consequences for the sensory properties of the wine. These findings highlight the complex interactions between pectin, anthocyanins, and tannins, and their influence on pigment formation and wine composition during fermentation and aging.

Structure-function relationships in (poly)phenol-enzyme binding: Direct inhibition of human salivary and pancreatic α-amylases.

(Poly)phenols inhibit α-amylase by directly binding to the enzyme and/or by forming starch-polyphenol complexes. Conventional methods using starch as the substrate measure inhibition from both mechanisms, whereas the use of shorter oligosaccharides as substrates exclusively measures the direct interaction of (poly)phenols with the enzyme. In this study, using a chromatography-based method and a short oligosaccharide as the substrate, we investigated the detailed structural prerequisites for the direct inhibition of human salivary and pancreatic α-amylases by over 50 (poly)phenols from the (poly)phenol groups: flavonols, flavones, flavanones, flavan-3-ols, polymethoxyflavones, isoflavones, anthocyanidins and phenolic acids. Despite being structurally very similar (97% sequence homology), human salivary and pancreatic α-amylases were inhibited to different extents by the tested (poly)phenols. The most potent human salivary α-amylase inhibitors were luteolin and pelargonidin, while the methoxylated anthocyanidins, peonidin and petunidin, significantly blocked pancreatic enzyme activity. B-ring methoxylation of anthocyanidins increased inhibition against both human α-amylases while hydroxyl groups at C3 and B3' acted antagonistically in human salivary inhibition. C4 carbonyl reduction, or the positive charge on the flavonoid structure, was the key structural feature for human pancreatic inhibition. B-ring glycosylation did not affect salivary enzyme inhibition, but increased pancreatic enzyme inhibition when compared to its corresponding aglycone. Overall, our findings indicate that the efficacy of interaction with human α-amylase is mainly influenced by the type and placement of functional groups rather than the number of hydroxyl groups and molecular weight.

Gallic acid improves color quality and stability of red wine via physico-chemical interaction and chemical transformation as revealed by thermodynamics, real wine dynamics and benchmark quantum mechanical calculations.

The aim of this study was to explore the copigmentation effect of gallic acid on red wine color and to dissect its mechanism at the molecular level. Three-dimensional studies, e.g., in model wine, in real wine and in silico, and multiple indicators, e.g., color, spectrum, thermodynamics and phenolic dynamics, were employed. The results showed that gallic acid significantly enhanced the color quality and stability of red wine. Physico-chemical interactions and chemical transformations should be the most likely mechanism, and physico-chemical interactions are also a prerequisite for chemical transformations. QM calculations of the physico-chemical interactions proved that the binding between gallic acid and malvidin-3-O-glucoside is a spontaneous exothermic reaction driven by hydrogen bonding and dispersion forces. The sugar moiety of malvidin-3-O-glucoside and the phenolic hydroxyl groups of gallic acid affect the formation of hydrogen bonds, while the dispersion interaction was related to the stacking of the molecular skeleton.

Stability of individual anthocyanins from black carrots stored in light and darkness - Impact of acylation.

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

Black Rice Anthocyanins as An Effective Antioxidant of Inhibition of Oil Oxidative Based on Molecular Modification.

This present work investigated the influence of black rice anthocyanins as antioxidants on the oxidation stability of oil. Malonic acid, succinic acid and succinic anhydride were grafted on black rice anthocyanins through acylation method to improve their antioxidant activity in oil. The results from fourier transform infrared spectroscopy (FTIR) showed new absorption peaks near 1744 cm -1 and 1514 cm -1 , which implied that malonic acid, succinic acid and succinic anhydride grafted on the -OH of glucoside and rutinoside through esterification reaction and resulted that the polarity of these were reduced. Total content of anthocyanin (TAC) decreased to 166. 3 mg/g, 163.7 mg/g and 150.2 mg/g, respectively after modification with succinic acid, malonic acid and succinic anhydride. Compared with native anthocyanins, the acylation of black rice anthocyanins partially reduced its antioxidant activity. In addition, DPPH clearance of molecular modified anthocyanins decreased to 62.6% (San-An). As revealed in the oil stability through the determination of primary oxidation products (PV) and secondary oxidation products (p-AV), Sa-An, Ma-An and San-An showed stronger antioxidant activity in Schaal oven accelerated oxidation test during 12 days than native black rice anthocyanin in both corn oil and flaxseed oil. Molecular modified black rice anthocyanins are expected to be used as colorants, antioxidants, etc. in oil-rich food.

Theoretical Study of Cyanidin-Resveratrol Copigmentation by the Functional Density Theory.

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.

Continuous-Flow High-Pressure Homogenization of Blueberry Juice Enhances Anthocyanin and Ascorbic Acid Stability during Cold Storage.

Blueberries (Vaccinium section Cyanococcus) have a wealth of bioactive compounds, including anthocyanins and other antioxidants, that offer significant health benefits. Preserving these compounds and maintaining the sensory and nutritional qualities of blueberry products such as juice during cold market storage is critical to meet consumer expectations for nutritious, safe, and minimally processed food. In this study, we compared the effects of two preservation processing techniques, high-temperature short-time (HTST) and continuous flow high-pressure homogenization (CFHPH), on blueberry juice quality during storage at 4 °C. Our findings revealed that inlet temperature (Tin) of CFHPH processing at 4 °C favored anthocyanin retention, whereas Tin at 22 °C favored ascorbic acid retention. After 45 days of storage, CFHPH (300 MPa, 1.5 L/min, 4 °C) juice retained up to 54% more anthocyanins compared to control at 0 day. In contrast, HTST treatment (95 °C, 15 s) initially increased anthocyanin concentrations but led to their subsequent degradation over time, while also significantly degrading ascorbic acid. Furthermore, CFHPH (300 MPa, 4 °C) juice had significantly lower polyphenol oxidase activity (>80% less than control), contributing to the overall quality of the juice. This innovative processing technique has the potential to improve commercial blueberry juice, and help meet the rising demand for healthy and appealing food choices.

Extraction of tannin, colour and aroma compounds in pinot noir wines as affected by clone selection and whole bunch addition.

Our previous study revealed stem inclusion fermentation reduced anthocyanin, and increased tannin and aroma compounds responsible for green notes. This study further investigated the effect of clone selection and whole bunch fermentation on Pinot noir wine composition, with focus on tannin composition. Three treatments were conducted using two clones (AM10/5 and UCD5) in 2021 and 2022: 100% destemmed (DS), 30% whole bunch (WB30), and 60% whole bunch (WB60). WB60 increased stem and skin derived tannins but reduced seed derived tannin proportion in wines. Clone selection had an impact on tannin composition and an even greater impact on tannin concentration, colour, and aroma compounds. AM10/5 produced wines with higher tannin, polymeric pigments and darker colour. AM10/5 wines also had higher concentration of phenylethyl alcohol, but lower concentrations of 3-isobutyl-2-methoxypyrazine and ethyl esters, indicating more floral but less fruity and green notes.

Application of poly(L-lactic acid)-based films for equilibrium modified atmosphere packaging of "Kyoho" grapes and its favorable protection for anthocyanins.

Grapes were packaged by different Poly (L-lactic acid)-based packaging films (PLTL-PLEL) and stored at 5 °C for 35 days to investigate the effects of equilibrium modified atmosphere packaging on the quality of "Kyoho" grapes during storage. Changes in physiochemical quality, antioxidant content and senescence of grapes were studied. Furthermore, UPLC-Q-TOF-MS/MS was used to observe and identify key factors influencing the variation of grape anthocyanins under different atmosphere conditions. Alterations in gas components and enzyme activities significantly impacted anthocyanin levels, highlighting oxygen concentration as the primary influence on total anthocyanin levels. The PLTL-PLEL50 packaging resulted in an approximate 5.7% lower weight loss and increased soluble solids by approximately 14.4%, vitamin C, total phenols and flavonoids reaching 60.2 mg/100 g, 8.4 mg/100 g and 7.2 mg/100 g, respectively. This packaging also preserved higher anthocyanin levels, with malvidin-3-glucoside and peonidin-3-glucoside at 0.55 µg/mL and 1.62 µg/mL, respectively, on the 35th day of storage.

Exploring high hydrostatic pressure effects on anthocyanin binding to serum albumin and food-derived transferrins.

This study investigated the effects of high hydrostatic pressure (HHP) on the binding interactions of cyanindin-3-O-glucoside (C3G) to bovine serum albumin, human serum albumin (HSA), bovine lactoferrin, and ovotransferrin. Fluorescence quenching revealed that HHP reduced C3G-binding affinity to HSA, while having a largely unaffected role for the other proteins. Notably, pretreating HSA at 500 MPa significantly increased its dissociation constant with C3G from 24.7 to 34.3 µM. Spectroscopic techniques suggested that HSA underwent relatively pronounced tertiary structural alterations after HHP treatments. The C3G-HSA binding mechanisms under pressure were further analyzed through molecular dynamics simulation. The localized structural changes in HSA under pressure might weaken its interaction with C3G, particularly polar interactions such as hydrogen bonds and electrostatic forces, consequently leading to a decreased binding affinity. Overall, the importance of pressure-induced structural alterations in proteins influencing their binding with anthocyanins was highlighted, contributing to optimizing HHP processing for anthocyanin-based products.

Blueberry anthocyanin based active intelligent wheat gluten protein films: Preparation, characterization, and applications for shrimp freshness monitoring.

The aim of this study was to prepare active intelligent gluten protein films using wheat gluten protein (WG) and apple pectin (AP) as film-forming matrices, and blueberry anthocyanin extract (BAE) as a natural indicator. SEM and FT-IR analyses demonstrated the successful immobilization of BAE in the film matrix by hydrogen bonding interactions and its compatibility with WG and AP. The resultant WG-AP/BAE indicator films demonstrated notable antioxidant activity, color stability, barrier qualities, pH and ammonia response sensitivity, and mechanical properties. Among them, WG-AP/BAE5 exhibited the best mechanical properties (TS: 0.83 MPa and EB: 242.23%) as well as the lowest WVP (3.92 × 10-8 g.m/m2.Pa.s), and displayed high sensitivity to volatile ammonia. In addition, WG-AP/BAE5 showed a color shift from purplish red to green to yellowish green, demonstrating the monitoring of shrimp freshness in real time. Consequently, this study offers a firm scientific foundation for the development of active intelligent gluten protein films and their use in food freshness assessments.

Ultrasound-assisted extraction and concentration of phenolic compounds from jabuticaba sabará (Plinia peruviana (Poir.) Govaerts) peel by nanofiltration membrane.

Jabuticaba peel, rich in antioxidants, offering health benefits. In this study, the extraction of phenolic compounds from jabuticaba peel using ultrasound-assisted (UA) and their subsequent concentration by nanofiltration (NF) employing a polyamide 200 Da membrane was evaluated. The UA extractions were conducted using the Central Composite Rotatable Design (CCRD) 22 methodology, with independent variables extraction time (11.55 to 138 min) and temperature (16.87 to 53.3 °C), and fixed variables mass to ethanol solution concentration at pH 1.0 (1:25 g/mL), granulometry (1 mm), and ultrasonic power (52.8 W). The maximum concentrations obtained were 700.94 mg CE/100 g for anthocyanins, 945.21 mg QE/100 g for flavonoids, 133.19 mg GAE/g for phenols, and an antioxidant activity IC50 of 24.36 µg/mL. Key phenolic compounds identified included cyanidin-3-glucoside, delphinidin-3-glucoside, and various acids like syringic and gallic. NF successfully concentrated these compounds, enhancing their yield by up to 45%. UA and NF integrate for sustainable extraction.

Intermolecular interactions between malvidin-3-O-glucoside and caffeic acid: Structural and thermodynamic characterization and its effect on real wine color quality.

The copigmentation effect between malvidin-3-O-glucoside and caffeic acid was comprehensive inquiry on the model wine solution, theoretical simulation and real wine. Thermodynamic parameters were determined by UV/Visible spectroscopy and Isothermal titration calorimetry (ITC). Theoretical data were obtained employing a dispersion-corrected density functional approach. The effects in real wines were investigated by adding the caffeic acid during different fermentation periods. Results shown that the copigmentation reaction between caffeic acid and malvidin-3-O-glucoside is a spontaneous exothermic reaction driven by hydrogen bonding and dispersions forces. Computations show that the polyhydroxyl sugar moiety and phenolic hydroxyl groups are the key active sites. The addition of caffeic acid in post-alcohol fermentation samples evidences an improving color characteristics in the wine.

Enzymatically green-produced bacterial cellulose nanoparticle-stabilized Pickering emulsion for enhancing anthocyanin colorimetric performance of versatile films.

To enhance the colorimetric performance of anthocyanin (Ant), a konjac glucomannan (KGM)-based multifunctional pH-responsive indicator film was fabricated by introducing enzymatically prepared bacterial nanocellulose (EBNC) stabilized camellia oil/camellia essential oil Pickering emulsion (BCCE). Specifically, optimized enzymatic hydrolysis time (36 h) was determined based on the particle size and microstructure. Then BCCE (containing 0.4% EBNC) was incorporated into Ant-containing KGM, and the novel active indicator film (KGM-Ant-BCCE) was constructed. Films with varying BCCE concentrations (3%-11%) exhibited enhanced UV shielding, thermal stability, mechanical strength, water vapor and oxygen permeability, hydrophobicity, and antioxidant performance. The pronounced color change of KGM-Ant-BCCE indicated its potential for visually detecting shrimp freshness. Moreover, the biodegradability (25 days) confirmed the environmentally benign property of the film. In summary, incorporating green-produced EBNC nanoparticle-stabilized BCCE offers an innovative pathway to improve the color indication capability of polysaccharide-based smart packaging.

Image recognition technology provides insights into relationships between anthocyanin degradation and color variation during jet drying of black carrot.

To identify interesting relationships between anthocyanin degradation and color variation during food processing, black carrot slice (BCS) was dried by air-impingement jet drying (AIJD) and hot air drying (HAD). AIJD was a better technology for drying BCS than HAD. Results of colorimeter determination showed that the color of BCS was significantly changed during AIJD at 50, 60 and 70 °C. UHPLC-QqQ-MS/MS analysis found that AIJD-induced degradations of main BCS anthocyanins, cyanidin-3-xylosyl(feruloylglucosyl)galactoside and cyanidin-3-xylosyl(sinapoylglucosyl)galactoside, belonged to non-spontaneous endothermic reactions, which followed the 0.5- and 1-order kinetic equations, respectively. Anthocyanin content and colors obtained from colorimeter presented strong positive correlation, particularly the a* and chroma values. We further developed a Python script based on image recognition technology to visualize the correlation matrixes between the anthocyanin contents and colors of BSC images. The plots revealed that strong positive correlations between anthocyanins and colors primarily concentrated in the sample's periphery following a concentric pattern.

Research Progress on Active Ingredients and Product Development of Lycium ruthenicum Murray.

Lycium ruthenicum Murray possesses significant applications in both food and medicine, including antioxidative, anti-tumor, anti-fatigue, anti-inflammatory, and various other effects. Consequently, there has been a surge in research endeavors dedicated to exploring its potential benefits, necessitating the organization and synthesis of these findings. This article systematically reviews the extraction and content determination methods of active substances such as polysaccharides, anthocyanins, flavonoids, and polyphenols in LRM in the past five years, as well as some active ingredient composition determination methods, biological activities, and product development. This review is divided into three main parts: extraction and determination methods, their bioactivity, and product development. Building upon prior research, we also delve into the economic and medicinal value of Lycium ruthenicum Murray, thereby contributing significantly to its further exploration and development. It is anticipated that this comprehensive review will serve as a valuable resource for advancing research on Lycium ruthenicum Murray.

Preparation of Steamed Purple Sweet Potato-Based Films Containing Mandarin Essential Oil for Smart Packaging.

Anthocyanin-rich steamed purple sweet potato (SPSP) is a suitable raw material to produce smart packaging films. However, the application of SPSP-based films is restricted by the low antimicrobial activity of anthocyanins. In this study, SPSP-based smart packaging films were produced by adding mandarin essential oil (MEO) as an antimicrobial agent. The impact of MEO content (3%, 6%, and 9%) on the structures, properties, and application of SPSP-based films was measured. The results showed that MEO created several pores within films and reduced the hydrogen bonding system and crystallinity of films. The dark purple color of the SPSP films was almost unchanged by MEO. MEO significantly decreased the light transmittance, water vapor permeability, and tensile strength of the films, but remarkably increased the oxygen permeability, thermal stability, and antioxidant and antimicrobial properties of the films. The SPSP-MEO films showed intuitive color changes at different acid-base conditions. The purple-colored SPSP-MEO films turned blue when chilled shrimp and pork were not fresh. The MEO content greatly influenced the structures, physical properties, and antioxidant and antimicrobial activities of the films. However, the MEO content had no impact on the color change ability of the films. The results suggested that SPSP-MEO films have potential in the smart packaging of protein-rich foods.

Anthocyanins as Natural Food Colorings: The Chemistry Behind and Challenges Still Ahead.

Anthocyanins are polyphenolic O-glycosides widely responsible for the bright red, purple, and blue colors in the plant kingdom, including a great variety of fruits and vegetables. Hence, they have attracted considerable scientific and industrial interest as potential natural food colorings. However, individual anthocyanins are intrinsically reactive molecules combining electrophilic, nucleophilic, and electron-donating properties. This reactivity may be not only a source of color diversity with, for instance, the formation of new pigments upon winemaking and storage but also a cause of great color instability involving a combination of reversible and irreversible mechanisms (e.g., water addition, autoxidation) leading to colorless products. Hence, using anthocyanin-rich plant extracts as food colorings requires a deep understanding of these color-damaging mechanisms and, no less importantly, of the color-stabilizing mechanisms developed by plants, including π-stacking interactions (self-association, copigmentation), metal binding, and a combination of both. The potential of anthocyanins from deeply colored vegetables, typically acylated by hydroxycinnamic acid residues, will be emphasized in that respect. Moreover, food-grade biopolymers (proteins, polysaccharides) may provide suitable matrices for ready-to-use formulations of anthocyanins as food colorings. In this short review, the mechanisms of color loss and color stabilization are discussed as a function of anthocyanin structure and environment, and some challenges still ahead are outlined.

Unveiling the impact of high-pressure processing on anthocyanin-protein/polysaccharide interactions: A comprehensive review.

Anthocyanins, natural plant pigments responsible for the vibrant hues in fruits, vegetables, and flowers, boast antioxidant properties with potential human health benefits. However, their susceptibility to degradation under conditions such as heat, light, and pH fluctuations necessitates strategies to safeguard their stability. Recent investigations have focused on exploring the interactions between anthocyanins and biomacromolecules, specifically proteins and polysaccharides, with the aim of enhancing their resilience. Notably, proteins like soy protein isolate and whey protein, alongside polysaccharides such as pectin, starch, and chitosan, have exhibited promising affinities with anthocyanins, thereby enhancing their stability and functional attributes. High-pressure processing (HPP), emerging as a non-thermal technology, has garnered attention for its potential to modulate these interactions. The application of high pressure can impact the structural features and stability of anthocyanin-protein/polysaccharide complexes, thereby altering their functionalities. However, caution must be exercised, as excessively high pressures may yield adverse effects. Consequently, while HPP holds promise in upholding anthocyanin stability, further exploration is warranted to elucidate its efficacy across diverse anthocyanin variants, macromolecular partners, pressure regimes, and their effects within real food matrices.

Influence of Potential Alcohol in Grapes on Phenolic and Sensory Characteristics of Red Wine.

Potential alcohol, as obtained by grape maturity, affects the extraction of phenolics during winemaking. The extent to which potential alcohol is correlated to phenolic and sensory characteristics of red wine was investigated. Decoupling of the ripening kinetics of grape constituents due to climate change emphasizes this question. The impact of potential alcohol, as naturally obtained by grape maturity or adjusted by sugar addition, representing high sugar but low phenolic maturity, on wine characteristics was investigated for two varieties over two vintages. Enhancement of potential alcohol to late harvest conditions did not achieve the sensory characteristics of wine made from phenolic mature grapes. An experimental model was developed revealing the contribution of potential alcohol to phenolic and sensory characteristics. In Pinot noir, anthocyanins correlated well with natural potential alcohol but were not influenced by enhanced potential alcohol. In Cabernet Sauvignon, polymeric pigments provided the most accurate information about grape maturity perception in wine.