Phenolic Characterization of a Purple Maize (Zea mays cv. "Moragro") by HPLC-QTOF-MS and Study of Its Bioaccessibility Using a Simulated In Vitro Digestion/Caco-2 Culture Model.

The present work aimed to characterize the phenolic and antioxidant content of the Argentinian purple maize "Moragro" cultivar. Additionally, the INFOGEST simulated in vitro digestion model was used to establish the effect of digestion on bioactive compounds. Finally, digestion samples were used to treat Caco-2 cells in the transwell model to better understand their bioavailability. Twenty-six phenolic compounds were found in purple maize cv. "Moragro", 15 nonanthocyanins and 11 anthocyanins. Several compounds were identified in maize for the first time, such as pyrogallol, citric acid, gallic acid, kaempferol 3-(6″-ferulylglucoside), and kaempferol 3-glucuronide. Anthocyanins accounted for 24.9% of total polyphenols, with the predominant anthocyanin being cyanidin-3-(6″ malonylglucoside). Catechin-(4,8)-cyanidin-3,5-diglucoside and catechin-(4,8)-cyanidin-3-malonylglucoside-5-glucoside were detected as characteristics of this American maize variety. Total polyphenol content (TPC; by the Folin-Ciocalteu method), HPLC-DAD/MSMS, and antioxidant activity [by DPPH and ferric-reducing antioxidant power (FRAP)] were evaluated throughout in vitro digestion. TPC, DPPH, and FRAP results were 2.71 mg gallic acid equivalents (GAE)/g, 24 µmol Trolox equiv/g, and 22 µmol Trolox eq/g, respectively. The in vitro digestion process did not cause significant differences in TPC. However, the antioxidant activity was significantly decreased. Moreover, the bioavailability of anthocyanins was studied, showing that a small fraction of polyphenols in their intact form was conserved at the end of digestion. Finally, a protective effect of digested maize polyphenols was observed in the Caco-2 cell viability. The results suggest that "Moragro" purple maize is a good source of bioavailable anthocyanins in the diet and an interesting source of this group of compounds for the food industry.

Hybrid chiral nanocellulose-cyanidin composite with pH and humidity response for visual inspection and real-time tracking of shrimp quality and freshness.

Biobased multi-stimulation materials have received considerable attention for intelligent packaging and anti-counterfeiting applications. Cellulose nanocrystals (CNCs) and cyanidins are good material candidates for monitoring food freshness as they are eco-friendly natural substances. This work incorporated cyanidin with a CNC-hosting substrate to develop a simple, environment-friendly colorimetric device to visualize food freshness. Across the pH range of 2-13, the indicator exhibited noticeable color changes ranging from red to gray and eventually to orange. The CNC-cyanidin (CC) film exhibited a dramatic color change from blue to dark red and high sensitivity at a relative humidity of 30 %-100 %. In corresponding to the total volatile elemental nitrogen (TVB-N) level of shrimp, the indicator showed distinguishable colors at different stages of shrimp. The findings imply that the samples have substantial potential for use as an intelligent indicator for tracking shrimp freshness.

Chemical stability of carboxylpyranocyanidin-3-O-glucoside under ß-glucosidase treatment and description of their interaction.

Anthocyanins are susceptible to degradation by ß-glycosidase, resulting in color loss. This study analyzed the impact of ß-glycosidase on carboxylpyranocyanidin-3-O-glucoside (Carboxyl-pycy-3-gluc) and its precursor cyanidin-3-O-glucoside (Cy-3-gluc). Carboxyl-pycy-3-gluc exhibited enhanced stability upon treatment with ß-glucosidase. Ultraviolet-visible and circular dichroism spectroscopy revealed slight changes in the microenvironment and secondary structure of ß-glycosidase when carboxyl-pycy-3-gluc was present. The fluorescence experiment indicated that anthocyanins quench the fluorescence of ß-glycosidase through static quenching via hydrophobic interactions. Molecular docking of six types of carboxylpyranoanthocyanins and their precursors with ß-glycosidase revealed that carboxylpyranoanthocyanins exhibited lower binding affinity than their precursors, consistent with the enzyme kinetic experiment results. The incorporation carboxyl-pycy-3-gluc into Sanhua Plum Juice and Wine endowed them with vivid and stable coloration. The study illustrated that carboxyl-pycy-3-gluc exhibits low binding affinity with ß-glycosidase, thereby maintaining stability and confirming its potential as a colorant.

Valorization and protection of anthocyanins from strawberries (Fragaria×ananassa Duch.) by acidified natural deep eutectic solvent based on intermolecular interaction.

This study introduces an innovative approach for the valorization and protection of anthocyanins from 'Benihoppe' strawberry (Fragaria × ananassa Duch.) based on acidified natural deep eutectic solvent (NADES). Choline chloride-citric acid (ChCl-CA, 1:1) was selected and acidified to enhance the valorization and protection of anthocyanins through hydrogen bond. The optimal conditions (ultrasonic power of 318 W, extraction temperature of 61 °C, liquid-to-solid ratio of 33 mL/g, ultrasonic time of 19 min), yielded the highest anthocyanins of 1428.34 µg CGE/g DW. UPLC-Triple-TOF/MS identified six anthocyanins in acidified ChCl-CA extract. Stability tests indicated that acidified ChCl-CA significantly increased storage stability of anthocyanins in high temperature and light treatments. Molecular dynamics results showed that acidified ChCl-CA system possessed a larger diffusion coefficient (0.05 m2/s), hydrogen bond number (145) and hydrogen bond lifetime (4.38 ps) with a reduced intermolecular interaction energy (-1329.74 kcal/mol), thereby efficiently valorizing and protecting anthocyanins from strawberries.

Aerogel colorimetric label sensors based on carboxymethyl cellulose/sodium alginate with black goji anthocyanin for monitoring fish freshness.

A novel colorimetric aerogel was developed by the complexation of carboxymethyl cellulose (CMC), sodium alginate (SA), and black goji anthocyanin (BGA) followed by freeze-drying for monitoring fish (Coho salmon) freshness during storage at 4 °C and 25 °C. The various aerogels (C/S/B3:1, C/S/B2:1, C/S/B1:1, C/S/B1:2, and C/S/B1:3) externally and internally were characterized using SEM, FTIR, XRD, DSC, and TGA. Among them, the aerogel composite C/S/B1:2 exhibited the most uniform pore size, largest specific surface area, rapid color changes in various alkaline vapors (5 µM and 50 µM), and better mechanical strength. Furthermore, the colorimetric aerogel became dark blue from light purple during fish storage at temperatures of 4 °C and 25 °C when it reached pH 7.49 and 7.33, TVC 8.9 × 107 CFU/g and 8.5 × 107 CFU/g, and TVB-N 33.8 mg/100 g and 26.12 mg/100 g, respectively, indicating fish completely deteriorated. Taken together, the colorimetric aerogel composite C/S/B1:2 was promising for determining fish freshness, which could be utilized as a non-destructive and useful intelligent sensor in monitoring various fish and meat freshness and/or quality.

Study on preservation and monitoring effect of sodium alginate-konjac glucomannan films loaded with tea polyphenols and Lycium ruthenicum anthocyanins.

To investigate the efficacy of sodium alginate-konjac glucomannan (SA-KGM) films with anthocyanins (LRA) and tea polyphenols (TP) in meat, beef and grass carp were selected as representative meat products for preservation and freshness monitoring experiments at 4 °C. Concurrently, storage experiments of the films were conducted in this controlled environment. The results of the storage experiment showed that the films delayed meat spoilage by 2-4 days, nearly doubling the preservation time compared to the blank control. Additionally, the film exhibited significant capability to monitor the spoilage process of beef and grass carp. It was revealed by curve fitting analysis that there was a significant correlation between the color change of the film and the spoilage index of the meat. Throughout the storage experiment with the film, it was observed that moisture significantly influenced the microstructure and bonding situation of the films, thereby impacting their mechanical and barrier properties. However, the films were still able to maintain satisfactory physicochemical properties in general. The above findings were crucial in guiding the promotion of the film within the food preservation industry.

Smart labels based on polyvinyl alcohol incorporated with chitosan nanoparticles loaded with grape extract: Functionality, stability and food application.

Anthocyanins (ACNs) are natural compounds with potential applications due to their colorimetric response to pH. Due to their sensitivity to various environmental factors, nanoencapsulation with biopolymers is a successful strategy for stabilizing ACNs. In this work ACNs were extracted from grape skins and encapsulated into chitosan (CS) nanoparticles by ionic gelation using sodium tripolyphosphate (TPP) as a cross-linking agent. CS nanoparticles loaded with ACNs had particle sizes between 291 and 324 nm and polydispersity index around 0.3. The encapsulation efficiency of ACNs was approximately 60 %; and encapsulated anthocyanins (ACN-NPs) exhibited color change properties under different pH conditions. pH-sensitive labels based on polyvinyl alcohol (PVA) were prepared by the casting method. The effect of incorporating ACN-NPs on the physical, structural, and pH-sensitive properties of PVA labels was evaluated, and its application as shrimp freshness indicator was studied. The nanoencapsulation protected ACNs against heat and light treatments, preserving the original purple color. When applying the label, visible changes from red to blue until reaching yellow were observed with the change in the quality of the shrimp at the refrigeration temperature. The results suggest that PVA labels containing ACNs encapsulated in C-NPs can be used as smart packaging labels in the food industry.

Esterification of black bean anthocyanins with unsaturated oleic acid, and application characteristics of the product.

Esterification of anthocyanins with saturated fatty acids have been widely investigated, while that with unsaturated fatty acids is little understood. In this study, crude extract (purity âˆ¼ 35 %) of cyanidin-3-O-glucoside (C3G) from black bean seed coat was utilized as reaction substrate, and enzymatically acylated with unsaturated fatty acid (oleic acid). Optimization of various reaction parameters finally resulted in the highest acylation rate of 54.3 %. HPLC-MS/MS and NMR analyses elucidated the structure of cyanidin-3-O-glucoside-oleic acid ester (C3G-OA) to be cyanidin-3-O-(6″-octadecene)-glucoside. Introduction of oleic acid into C3G improved the lipophilicity, antioxidant ability, and antibacterial activity. Further, the color and substance stability analyses showed that the susceptibility of C3G and C3G-OA to different thermal, peroxidative, and illuminant treatments were highly pH dependent, which suggested individual application guidelines. Moreover, C3G-OA showed lower toxicity to normal cell (QSG-7701) and better inhibitory effect on the proliferation of HepG2 cells than C3G, which indicated its potential anti-tumor bioactivity.

Sustainable green extraction of anthocyanins and carotenoids using deep eutectic solvents (DES): A review of recent developments.

Recently, deep eutectic solvents (DES) have been extensively researched as a more biocompatible and efficient alternative to conventional solvents for extracting pigments from natural resources. The efficiency of DES extraction for the anthocyanin and carotenoid can be enhanced by microwave-assisted extraction (MAE) and/or ultrasound-assisted extraction (UAE) techniques. Apart from the extraction efficiency, the toxicity and recovery of the pigments and their bioavailability are crucial for potential applications. A plethora of studies have explored the extraction efficiency, toxicity, and recovery of pigments from various natural plant-based matrices using DES. Nevertheless, a detailed review of the deep eutectic solvent extraction of natural pigments has not been reported to date. Additionally, the toxicity, safety, and bioavailability of the extracted pigments, and their potential applications are not thoroughly documented. Therefore, this review is designed to understand the aforementioned concepts in using DES for anthocyanin and carotenoid extraction.

Multipurpose arrowroot starch films with anthocyanin-rich grape pomace extract: Color migration for food simulants and monitoring the freshness of fish meat.

Extraction of anthocyanins from grape pomace, is a way of valuing these abundant by-products with low added value. Its integration into films may allow it to be used in bioactive packaging, which creates new color and solubility properties for food and smart food packaging which tracks the freshness of fish. Films of arrowroot starch added with different concentrations of grape pomace extract (GPE) were flexible to handle, reddish and presented a high content of anthocyanins. The water vapor permeability increased by 17 %, while the tensile strength of arrowroot starch film decreased by 79 % with the addition of 40 % GPE. The addition of GPE increased the solubility of the starch film in aqueous and lipid food simulants by 121 and 119 %. The GPE pigment preferentially migrated to the aqueous simulant due to the hydrophilic nature of anthocyanins and starch. The GPE film showed distinguishable color changes in different pH buffer solutions from pink at pH 2 to light blue at pH 7 and slightly yellowish green at pH 10. When the composite films were monitored for fish meat freshness, the change in color of the film from reddish pink to slightly green after 96 h of storage at 25 °C was evident.

The Role of Anthocyanins in Alleviating Intestinal Diseases: A Mini Review.

Anthocyanins are phytonutrients with physiological activity belonging to the flavonoid family whose transport and absorption in the human body follow specific pathways. In the upper gastrointestinal tract, anthocyanins are rarely absorbed intact by active transporters, with most reaching the colon, where bacteria convert them into metabolites. There is mounting evidence that anthocyanins can be used for prevention and treatment of intestinal diseases, including inflammatory bowel disease (IBD), irritable bowel syndrome (IBS), and colorectal cancer (CRC), through the protective function on the intestinal epithelial barrier, immunomodulation, antioxidants, and gut microbiota metabolism. Dietary anthocyanins are summarized in this comprehensive review with respect to their classification and structure as well as their absorption and transport mechanisms within the gastrointestinal tract. Additionally, the review delves into the role and mechanism of anthocyanins in treating common intestinal diseases. These insights will deepen our understanding of the potential benefits of natural anthocyanins for intestinal disorders.

Enzymatic hydrolysis improves the encapsulation properties of rice bran protein by increasing retention of anthocyanins in microparticles of grape juice.

There is a growing demand for the food industry to find appealing matrices that display a clean and sustainable label capable of replacing animal proteins in the encapsulation market for natural pigments. Therefore, this study evaluated the impact of enzymatic hydrolysis by Flavourzyme protease on the encapsulation properties of rice bran proteins, aiming to protect anthocyanins in grape juice microparticles. To achieve this, rice bran protein hydrolysates (RPH) with low (5%, LRPH), medium (10%, MRPH), and high (15%, HRPH) degrees of hydrolysis (DH) were used combined with maltodextrin as carrier agents for the microencapsulation of grape juice by spray drying. The feed solutions contained 1 g of carrier agents (CA)/g of soluble solids from the juice (SS) and protein: a 15% CA ratio. Non-hydrolyzed rice protein was used as a carrier agent to obtain a control sample to evaluate the effect of enzymatic hydrolysis on the microencapsulation of grape juice. Protein modification increased the surface activity of the protein and its ability to migrate to the surface of the microparticles, forming a protective film, as observed by X-ray photoelectron spectroscopy. Using HRPH as a carrier agent combined with maltodextrin improved the internal and total anthocyanin retention, antioxidant capacity measured by DPPH and ABTS+ assays, and powder recovery compared to the control sample, and increased DH reduced particle size and powder stickiness. These particles were more homogeneous, rough, and without cracks. The microencapsulation efficiency was above 70%. All powders exhibited low values of hygroscopicity and degree of caking. Therefore, enzymatic hydrolysis proves to be a promising alternative for improving rice bran protein's encapsulating properties since using RPH as an encapsulating agent conferred greater protection of anthocyanins in microparticles. Moreover, the HRPH sample exhibited the most favorable outcomes overall, indicating its potential for prospective utilization in the market, supported by its elevated Tg.

Smart colorimetric indicator films prepared from chitosan and polyvinyl alcohol with high mechanical strength and hydrophobic properties for monitoring shrimp freshness.

This work aimed to develop and characterize a colorimetric indicator films based on chitosan (CS), polyvinyl alcohol (PVA), and shikonin (SKN) from radix Lithospermi by casting method. The prepared films can serve as smart packaging for monitoring shrimp freshness which having excellent antimicrobial and antioxidant activity. The shikonin containing films have better hydrophobicity, barrier properties, and tensile strength. The release kinetics analysis shows that the loading amount causes a prolonged release of SKN from the prepared films. Increasing SKN in the CS/PVA film from 1 wt% to 2 wt% improved antibacterial effect for 24 h. Additionally, pH-sensitive color shifts from reddish (pH 2) to purple-bluish (pH 13) were visually seen in shikonin based solutions as well as films. The CS/PVA/SKN film detected shrimp deterioration at three temperatures (25, -20, and 4 °C) through color change. This study introduces a favorable approach for smart packaging in the food industry using multifunctional films.

Preparation and properties of polyvinyl alcohol/chitosan-based hydrogel with dual pH/NH3 sensor for naked-eye monitoring of seafood freshness.

To address the issue of food spoilage causing health and economic loss, we developed a pH/NH3 dual sensitive hydrogel based on polyvinyl alcohol/chitosan (PVA/CS) containing chitosan-phenol red (CP). The CP was synthesized via Mannich reaction and immobilized it in PVA/CS hydrogel through freezing/thawing method to prepare the final PVA/CS/CP hydrogel. The synthesis of CP was confirmed by 1H NMR, FT-IR, XRD, UV-vis, and XPS. The characteristics of hydrogel were evaluated by FT-IR, XRD, SEM, mechanical properties, thermal stability, leaching, and color stability tests. The PVA/CS/CP hydrogel showed distinctly different color at various pH and NH3 vapor levels (yellow to purple). The hydrogel exhibited obvious color changes (ΔE = 46.95) in response to shrimp spoilage, stored at 4 °C. It showed positive and strong correlation between the ΔE values of the indicator hydrogel and total volatile basic nitrogen (TVB-N) as (R2 = 0.9573) and with pH as (R2 = 0.8686), respectively. These results clearly show that the PVA/CS/CP hydrogel could be applied for naked-eye real-time monitoring of seafood freshness in intelligent packaging.

A major facilitator superfamily transporter MdtH in Escherichia coli is involved in anthocyanin biosynthesis and secretion.

Anthocyanin cyanidin 3-O-glucoside (C3G) is a natural pigment widely used in food and nutraceutical industries. Its microbial synthesis in Escherichia coli is a promising and efficient way toward large-scale production. The current production titer is low partly due to the accumulation of C3G inside the producing microbes; thus, it is important to explore native transporters responsible for anthocyanin secretion. Currently, there has been only one native E. coli transporter identified with C3G-transporting capability, and its overexpression has a very limited effect on the promotion of extracellular C3G production. In this study, we report the identification and verification of an efficient intrinsic C3G efflux transporter MdtH in E. coli through transcriptomic analysis and genetic/biochemical studies. MdtH could bind C3G with high affinity, and its overexpression increased the extracellular C3G biosynthesis in E. coli by 110%. Our study provides a new regulation target for microbial biosynthesis of C3G and other anthocyanins. IMPORTANCE: Cyanidin 3-O-glucoside (C3G) is a natural colorant with health-promoting activities and is, hence, widely used in food, cosmetic, and nutraceutical industries. Its market supply is currently dependent on extraction from plants. As an alternative, C3G can be produced by the microbe Escherichia coli in a green and sustainable way. However, a large portion of this compound is retained inside the cell of E. coli, thus complicating the purification process and limiting the high-level production. We have identified and verified an efficient native transporter named MdtH in E. coli that can export C3G to the cultivation medium. Overexpression of MdtH could improve extracellular C3G production by 110% without modifications of the metabolic pathway genes or enzymes. This study reveals a new regulation target for C3G production in bacteria and provides guidance to the microbial biosynthesis of related compounds.

Pressurized liquid extraction of bioactive compounds from grape peel and application in pH-sensing carboxymethyl cellulose films: A promising material to monitor the freshness of pork and milk.

This study produced pH-sensing carboxymethyl cellulose (CMC) films functionalized with bioactive compounds obtained by pressurized liquid extraction (PLE) of grape peel to monitor the freshness of pork and milk. A semi-continuous PLE was conducted using hydroethanolic solution (70:30, v/v) at a flow rate of 5 mL/min, 15 MPa, and 60 °C. The films were produced by the casting technique using CMC (2.5 %, w/v), glycerol (1 %, v/v), and functionalized with 10, 30, and 50 % (v/v) grape peel extract. From the results obtained, LC-MS/MS revealed that PLE extracted twenty-seven phenolic compounds. The main phenolic compounds were kaempferol-3-glucoside (367.23 ± 25.88 µg/mL), prunin (270.23 ± 3.62 µg/mL), p-coumaric acid (236.43 ± 26.02 µg/mL), and procyanidin B1 (117.17 ± 7.29 µg/mL). The CMC films presented suitable color and mechanical properties for food packaging applications. The addition of grape peel extract promoted the pH-sensing property, showing the sensitivity of anthocyanins to pH changes. The films functionalized with grape peel extract presented good release control of bioactive compounds, making them suitable for food packaging applications. When applied to monitor the freshness of pork and milk, the films exhibited remarkable color changes associated with the pH of the food during storage. In conclusion, PLE is a sustainable approach to obtaining bioactive compounds from the grape peel, which can be applied in the formulation of pH-sensing films as a promising sustainable material to monitor food freshness during storage.

Effects of crosslinking agents on properties of starch-based intelligent labels for food freshness detection.

The impact of citric acid, carboxymethyl cellulose, carboxymethyl starch, sodium trimetaphosphate, or soybean protein on the crosslinking of starch-based films was examined. These crosslinking starch films were then used to create pH-sensitive food labels using a casting method. Blueberry anthocyanins were incorporated into these smart labels as a pH-sensitive colorimetric sensor. The mechanical properties, moisture resistance, and pH responsiveness of these smart labels were then examined. Crosslinking improved the mechanical properties and pH sensitivity of the labels. These different crosslinking agents also affected the hydrophobicity of the labels to varying degrees. Soybean protein was the only additive that led to labels that could sustain their structural integrity after immersion in water for 12 h. Because it increased the hydrophobicity of the labels, which decreased their water vapor permeability, moisture content, swelling index, and water solubility by 47 %, 29 %, 52 % and 10 %, respectively. The potential of using these labels to monitor the freshness of chicken breast was then examined. Only the films containing soybean protein exhibited good pH sensitivity, high structural stability, and low pigment leakage. This combination of beneficial attributes suggests that the composite films containing starch and soybean protein may be most suitable for monitoring meat freshness.

Development and evaluation of Bauhinia Kockiana extract-incorporated sago starch intelligent film strips for real-time freshness monitoring of coconut milk.

The aim of this work was to fabricate an intelligent film using sago starch incorporated with the natural source of anthocyanins from the Bauhinia Kockiana flower and use it to monitor the freshness of coconut milk. The films were developed using the casting method that included the addition of the different concentrations (0, 5, 10, 15 mg) of Bauhinia Kockiana extract (BKE) obtained using a solvent. The anthocyanin content of Bauhinia Kockiana was 262.17 ± 9.28 mg/100 g of fresh flowers. The spectral characteristics of BKE solutions, cross-section morphology, physiochemical, barrier, and mechanical properties, and the colour variations of films in different pH buffers were investigated. Films having the highest BKE concentration demonstrated the roughest structure and highest thickness (0.16 mm), moisture content (9.72 %), swelling index (435.83 %), water solubility (31.20 %), and elongation at break (262.32 %) compared to the other films. While monitoring the freshness of coconut milk for 16 h, BKE15 showed remarkable visible colour changes (from beige to dark brown), and the pH of coconut milk dropped from 6.21 to 4.56. Therefore, sago starch film incorporated with BKE has excellent potential to act as an intelligent pH film in monitoring the freshness of coconut milk.

Complexes of glycated casein and carboxymethyl cellulose enhance stability and control release of anthocyanins.

To improve the stability and sustained-release property of anthocyanins (ACNs), casein (CA) - dextran (DEX) glycated conjugates (UGCA) and carboxymethyl cellulose (CMC) were used to prepare ACNs-loaded binary and ternary complexes. The ACNs-loaded binary complexes (ACNs-UGCA) and ternary complexes (ACNs-UGCA-CMC) achieved by 8 min' ultrasonic treatment with 40 % amplitude. The binary and ternary complexes showed spherical structure and good dispersibility, with the average size of 121.2 nm and 132.4 nm respectively. The anthocyanins encapsulation efficiency of ACNs-UGCA-CMC increased almost 20 % than ACNs-UGCA. ACNs-UGCA-CMC had better colloidal stabilities than ACNs-UGCA, such as thermal stability and dilution stability. Simultaneously, both of the binary and ternary complexes significantly prevented anthocyanins from being degraded by heat treatment, ascorbic acid, sucrose and simulated gastrointestinal environment. The protective effect of ACNs-UGCA-CMC was more significant. Furthermore, ACNs-UGCA-CMC showed slower anthocyanins release in simulated releasing environment in vitro and a long retention time in vivo. Our current study provides a potential delivery for improving the stability and controlling release of anthocyanins.

The structure of anthocyanins and the copigmentation by common micromolecular copigments: A review.

Under natural physiological conditions, anthocyanins can keep bright and stable color for a long time due to the relatively stable acid-base environment of plant vacuoles and the copigmentation from various copigment substances, such as polyphenols, nucleotides, metallic ions and other substances. Therefore, 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). These interactions are usually manifested in both hyperchromic effect and bathochromic shifts. In addition to making anthocyanins more stable, the copigmentation also could make an important contribution to the diversification of their tone. Based on the molecular structure of anthocyanins, this review focuses on the interaction mode of auxochrome groups or copigments with anthocyanins and their effects on the chemical and color stability of anthocyanins.