A starch/gelatin-based Halochromic film with black currant anthocyanin and Nanocellulose-stabilized cinnamon essential oil Pickering emulsion: Towards real-time Salmon freshness assessment.

Neoterically, food packaging systems designed solely for prolonging shelf life or monitoring freshness could not fulfil the dynamic demands of consumers. In this current investigation, using the solvent casting method, a versatile halochromic indicator was created by integrating black currant anthocyanin and cinnamon essential oil-loaded Pickering emulsion into a starch/gelatin matrix. The resulting indicator film underwent scrutiny for its structural, pH-sensitive, antioxidant, and antimicrobial attributes. Unexpectedly, the amalgamation of anthocyanin and essential oil led to decreased antioxidant activity, dropping from 73.23 ± 2.17 to 28.87 ± 2.50 mg Trolox equivalent/g sample. Additionally, no discernible antimicrobial properties were detected in the composite film sample against both Staphylococcus aureus and Escherichia coli. Fourier transform infrared analyses unveiled robust intermolecular interactions among the film-forming components, providing insights into the observed antagonistic effect. The indicator film displayed distinctive colour changes corresponding to the fresh (greyish-brown), onset of decomposition (khaki), and spoiled (dark green) stages of the stored fish sample. This highlights its promising potential for providing real-time indications of food spoilage. These findings are important for the efficient design of composite films incorporating anthocyanins and essential oils. They serve as a guide towards their potential use as multifunctional packaging materials in the food industry.

Assessment on malvidin-3-glucoside interaction with TLR4 via multi-spectroscopic analysis and molecular docking.

As one innate immune pattern recognition receptor, Toll-like receptor 4 (TLR4) recently has been considered as a critical player in glucolipid metabolism. Blueberries contain high level of anthocyanins, especially malvidin-3-glucoside (Mv-3-glc), which contribute the anti-inflammatory, hypoglycemic, and hypolipidemic effects. It is speculated that Mv-3-glc is able to possess these functions by binding to TLR4. Here, the noncovalent interactions of Mv-3-glc and TLR4 was explored through multi-techniques including fluorescence and ultraviolet-visible (UV-Vis) absorption spectroscopy, as well as molecular docking. The results demonstrated that Mv-3-glc was able to quench TLR4 intrinsic fluorescence effectively. A stable complex was formed spontaneously and the reaction was exothermic. The degree of binding of Mv-3-glc to TLR4 showed a strong dependence on the chemical concentration, temperature, and pH values. The negative signs for enthalpy (ΔH = -69.1 ± 10.8 kJ/mol) and entropy (ΔS = -105.0 ± 12.3 J/mol/K) from the interaction of the Mv-3-glc and TLR4 shows that the major driving forces are the hydrogen bonding and van der Waals' force, which is consistent with the molecular docking results. In addition, molecular docking predicted that the active center with specific amino acid residues, Phe126, Ser127, Leu54, Ile153, and Tyr131 was responsible for the site of Mv-3-glc binding to TLR4/myeloid differentiation protein-2 (MD-2). These findings confirmed that Mv-3-glc could bind to TLR4, which would be beneficial to understand the target therapeutic effects of blueberry anthocyanins on TLR4 in regulating glucolipid metabolism.

Characterization and bioaccessibility assessment of bioactive compounds from camu-camu (Myrciaria dubia) powders and their food applications.

Camu-camu (Myrciaria dubia) is a tropical fruit known for its content of bioactive compounds. This study aimed to evaluate physicochemically, morphologically, andsensorialpowders from camu-camu obtained by spray-drying at two inlet temperatures (150 °C and 180 °C) with three encapsulating agents (maltodextrin, whey protein and a 50:50 mixture of both) and by freeze-drying of whole fruit. The use of maltodextrin protected bet anthocyanins (cyanidin-3-glucoside (C3G) and delphinidin-3-glucoside (D3G)), but whey protein showed a better protective effect on ascorbic and malic acids. These facts were confirmed during the storage stability test, finding that relative humidity is a critical variable in preserving the bioactive compounds of camu-camu powders. The powders with the highest content of bioactive compounds were added to a yogurt and a white grape juice, and then sensory evaluated. The bioaccessibility studies in gastric and intestinal phases showed better recovery percentages of bioactive compounds in camu-camu powders (up to 60.8 %) and beverages (up to 90 %) for C3G, D3G, ascorbic acid, and malic acid than in the fruit juice. Dehydration of camu-camu (M. dubia) is a strategy to increase the bioactive compounds stability, modulate the fruit sensory properties, and improve their bioavailability after incorporation in food matrices.

Comparison of wheatgrass juices from colored wheat (white, black, blue, and purple) for health promoting phytochemicals.

Wheatgrass juice is a low-acid functional drink extracted from white wheat seedlings. It is cherished by consumers due to its potent health benefits. The present study was conducted to develop and analyze wheatgrass juice from colored wheat lines to meet consumers increasing demand for a novel functional drink. The conventional lyophilized wheatgrass juice powder (WJLP) was found to contain significant chlorophyll content (0.3%), soluble phenolic content (0.6%), protein content (20%), moderate essential amino acid index (EAAI; 86%), high K (RDA; 11.6%) and antioxidant activity. Whereas, black WJLP had 564.2% higher anthocyanins, 30.5% higher chlorophyll, 87.5% higher soluble phenolic content, 10.2% higher proteins, 31.5% higher EAAI, and 112.5% higher antioxidant activity compared to white WJLP. Overall, the biochemical parameters of WJLP were increased in the order of white < blue < purple < black. The findings indicate that a proper cultivar selection can improve the nutritional value of wheatgrass juice.

Development of highly stable color indicator films based on κ-carrageenan, silver nanoparticle and red grape skin anthocyanin for marine fish freshness assessment.

Color indicator films for fish freshness were fabricated by incorporating κ-carrageenan (CAR) polymer with red grape skin extract (GSE) as a pH-sensing agent and silver nanoparticles (AgNPs) as an antimicrobial agent. Anthocyanins in GSE exhibited distinguished pH responsive color changes. GSE and AgNPs were well compatible with CAR with intramolecular interactions, approved by scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FTIR) and X-ray diffraction (XRD) analysis, thermo-gravimetric analysis (TGA) and differential scanning calorimetry (DSC). GSE-containing films displayed distinguished color changes in response to pH variations and volatile ammonia. Enhanced UV blocking ability and strong antioxidant activity were revealed for GSE included films without sacrificing the physico-chemical properties of the CAR film. Films containing AgNPs showed improved mechanical strength and strong antimicrobial ability against both Escherichia coli and Staphylococcus aureus. The CAR/AgNPs/GSE film displayed a distinctive color change corresponding to changes in the total volatile basic nitrogen (TVB-N) of fish during storage. In addition, the CAR/AgNPs/GSE film showed excellent color stability to consecutive UV exposure and its storage time at 25 °C is expected to be at least 240 days, which indicates that it has high potential as an intelligent food freshness indicator film.

A new cyanine from oxidative coupling of chlorogenic acid with tryptophan: Assessment of the potential as red dye for food coloring.

A red pigment was prepared by reaction of chlorogenic acid (CGA) with tryptophan (TRP) in air at pH 9 (37% w/w yield) and evaluated as food dye. The main component of pigment was formulated as an unusual benzochromeno[2,3-b]indole linked to a TRP unit, featuring a cyanine type chromophore (λmax 542, 546 nm, 1% extinction coefficient of the sodium salt = 244 ± 2). The chromophore showed a minimal pH dependence and proved stable for at least 3 h at 90 °C, both at pH 3.6 or 7.0, whereas red wine anthocyanins showed a substantial (30%) and betanin a complete abatement after 1 h at the acidic pHs. An intense coloring of different food matrices was obtained with the pigment at 0.01 % w/w. No toxicity was observed up to 0.2 mg/mL on hepatic and colonic cell lines. These data make this dye a promising alternative for red coloring of food.

Development of an easy-to-use colorimetric pH label with starch and carrot anthocyanins for milk shelf life assessment.

An intelligent freshness indicator was developed by immobilizing anthocyanins of black carrot (ABC) within the starch matrix (total anthocyanins content of 10 mg/100 mL) to monitor freshness/spoilage of milk. The microstructural, spectral, swelling and solubility properties as well as color stability (as a function of time, temperature and light) of the indicator at different pHs were characterized. The incorporation of ABC did not change the swelling index and water solubility. The prepared label showed visible color changes as a function of pH and excellent color stability after one month storage at different conditions. The total color difference (TCD) value of the indicator corresponded to the pH, acidity, and microbial growth of the pasteurized milk. The Pearson correlation coefficient showed a high correlation between TCD and pH (R = -0.979), while a high and positive correlation between TCD and acidity as well as TMC (R = 0.983 and 0.968, respectively) was observed. The developed label can discriminate fresh milk form the milk entered into the initial (TCD: 7.8 after 24 h) and final (TCD: 34.8 after 48 h) steps of spoilage. The fabricated label opens a new perspective to use anthocyanins-incorporated biopolymers in the milk intelligent packaging as a simple and easy-to-use freshness indicator.

Prospects for economical natural colorants: insights from maize.

KEY MESSAGE: Anthocyanin pigments from maize offer a natural yet economical alternative to artificial dyes. Breeding for optimal colorant production requires understanding and integrating all facets of anthocyanin chemistry and genetics research. Replacing artificial dyes with natural colorants is becoming increasingly popular in foods and beverages. However, natural colorants are often expensive, have lower stability, and reduced variability in hue. Purple corn is rich in anthocyanins and offers a scalable and affordable alternative to synthetic dyes ranging in color from orange to reddish-purple. This diversity is attributable to differences in anthocyanin composition and concentration. Here we review the chemistry, biosynthesis, and genetics of purple corn and outline key factors associated with the feasibility of producing an economical source of natural colorants. Anthocyanin compositional modifications including acylation, methylation, and polymerization with flavan-3-ols can influence color stability and hue, yet there is more to learn regarding the genetic factors responsible for these modifications. Activators and repressors of anthocyanin biosynthesis structural genes as well as factors controlling trafficking and storage largely control anthocyanin yield. Further knowledge of these mechanisms will allow breeders to apply molecular strategies that accelerate the production of purple corn hybrids to meet growing demands for natural colorants.

Radiation shielding parameters of some antioxidants using Monte Carlo method.

In this paper, radiation shielding parameters such as mass attenuation coefficients and half value layer (HVL) of some antioxidants are investigated using MCNPX (version 2.4.0). The validation of the generated MCNPX simulation geometry for antioxidant structures is provided by comparing the results with standard WinXcom data for radiation mass attenuation coefficients of antioxidants. Very good agreement between WINXCOM and MCNPX was obtained. The results from the validated geometry were used to calculate the shielding parameters of different antioxidants. The radiation attenuation properties of each antioxidant were compared with each other. The results showed that, on average, the highest and the lowest radiation mass attenuation coefficients were observed on hesperidin and delphinidin chloride, respectively. It can be concluded that Monte Carlo simulation is a strong tool and an alternate method where experimental investigations are not possible and a standard simulation setup can be used in further studies for different biological structures. It can also be concluded that the obtained results from this study are very useful for radiology and radiotherapy applications where antioxidants are frequently used.

Sampling Molecular Conformers in Solution with Quantum Mechanical Accuracy at a Nearly Molecular-Mechanics Cost.

We introduce a method to evaluate the relative populations of different conformers of molecular species in solution, aiming at quantum mechanical accuracy, while keeping the computational cost at a nearly molecular-mechanics level. This goal is achieved by combining long classical molecular-dynamics simulations to sample the free-energy landscape of the system, advanced clustering techniques to identify the most relevant conformers, and thermodynamic perturbation theory to correct the resulting populations, using quantum-mechanical energies from density functional theory. A quantitative criterion for assessing the accuracy thus achieved is proposed. The resulting methodology is demonstrated in the specific case of cyanin (cyanidin-3-glucoside) in water solution.

Enzymatic synthesis, structural characterization and antioxidant capacity assessment of a new lipophilic malvidin-3-glucoside-oleic acid conjugate.

The chemical modification of anthocyanins (water-soluble pigments) into more lipophilic compounds is very important to expand their application in the food, medical and cosmetic industries. In this work, the synthesis of a pure malvidin-3-glucoside-oleic acid ester derivative was achieved by enzymatic catalysis. This approach allowed us to synthesize a novel compound, malvidin-3-O-(6''-oleoyl)glucoside (Mv3glc-OA), which was structurally characterized by mass spectrometry and for the first time by NMR spectroscopy. The enzymatic reaction revealed to be regioselective giving only one ester product. Antioxidant features of the malvidin-3-glucoside lipophilic derivative by means of DPPH, FRAP and lipid peroxidation assays were assessed, which confirmed that the structural modification of the genuine malvidin-3-glucoside into a more lipophilic compound did not compromise its antioxidant potential and protected more effectively a lipidic substrate from oxidation, which is an important insight for future technological applications.

Assessment of In Vitro Biological Activities of Anthocyanins-Rich Plant Species Based on Plinia cauliflora Study Model.

Plinia cauliflora (jaboticaba) is a native fruit tree from Brazilian rainforest widely used in popular medicine to prevent diarrhea, asthma, and infections. Studies have shown that the major therapeutic potential of jaboticaba fruits is on its peel, a rich source of anthocyanins. These secondary metabolites have well-known antioxidant and anti-inflammatory activities and have been claimed to be effective to treat diabetes, cancer, cardiovascular diseases, and stroke. This chapter describes a series of methodologies to evaluate important in vitro biological activities like cytotoxicity, proliferation, and migration of a hydroalcoholic extract of jaboticaba peel on mouse fibroblast L929 line. Assays to assess total phenolic, flavonoid, and anthocyanin contents and antioxidant activities are described as well.

Isolation and characterization of phenolic compounds and anthocyanins from Murta (Ugni molinae Turcz.) fruits. Assessment of antioxidant and antibacterial activity.

Berry fruit consumption has become important in the promotion of human health, mainly due to their phenolic compounds, which have been associated with protection against different pathologies, as well as antimicrobial and other biological activities. Consequently, there has been a growing interest in identifying natural antioxidants and antimicrobials from these plants. This study aimed to characterize the phenolic chemical composition and anthocyanin profile of murta (Ugni molinae Turcz.) fruit, and to evaluate the antioxidant and antimicrobial activity of its extracts (ethanolic and methanolic). LC/MS of the ethanolic extracts showed the presence of three major compounds: caffeic acid 3-glu, quercetin-3-glu and quercetin, while in the methanolic acid extract they were cyanidin-3-glucoside, pelargonidin-3-arabinose and delphinidin-3-glucoside. The antioxidant activity of ethanolic extracts (DPPH· and ORAC assays) was higher than that of methanol acid extracts or purified anthocynins. Furthermore, the methanol acid extract showed an inhibitory activity against the bacteria E. coli and S. typhi similar to that of standard antibiotics. The results suggest that the antioxidant activity of the ethanolic extract is regulated by the high content of phenolic compounds and the fruit's characteristic color is due to the content of pelargonidin-3-arabinose and delphinidin-3-glucoside. The obtained results demonstrated the appreciable antioxidant and antibacterial activities, providing opportunities to explore murta extracts as biopreservatives.

Extraction of anthocyanins from black bean canning wastewater with macroporous resins.

This study investigated purification of anthocyanins from black bean canning wastewater by column chromatography with 5 types of macroporous resins (Diaion Hp20, Sepabeads Sp70, Sepabeads Sp207, Sepabeads Sp700, and Sepabeads Sp710). By-product of canned black beans was partially purified by filtration, in anticipation of higher performance during column chromatography. Equilibrium adsorption isotherms were measured and analyzed using Langmuir and Freundlich isotherm models. Both Langmuir (all R² ≥ 0.98) and Freundlich (all R² ≥ 0.97) models can describe the adsorption process of anthocyanins from black bean canning wastewater using the tested resins. The adsorption and desorption behaviors of anthocyanins were studied using a dynamic method on the 5 types of resins, and Sp700 presented the highest adsorption capacity (39 ± 4 mg/g; P < 0.05) as well as desorption capacity (19 ± 2%; P < 0.05), indicating that of the resins examined, Sp700 is a better candidate for purification of anthocyanins from black bean canning wastewater.

Profiling of anthocyanins for the taxonomic assessment of ancient purebred V. vinifera red grape varieties.

For the purpose of a varietal assessment, the berry skin anthocyanin profiles of 11 ancient native red grape varieties, sampled within the Irpinian area (Southern Italy), were compared to those of three reference Vitis vinifera cultivars and of a Kober 5BB rootstook hybrid (Vitisberlandieri×Vitisriparia). The 3,5-O-diglucoside anthocyanins and their acylated derivatives were monitored as signature compounds of non-V. vinifera grapes, using both reversed phase-high performance liquid chromatography (RP-HPLC) and matrix assisted laser desorption ionisation-time of flight (MALDI-TOF) mass spectrometry (MS). One variety (i.e. Tenta) was demonstrated to be an interspecific hybrid cross. Three additional varieties, namely Lacrima Nera, Aglianicone and a yet-unnamed variety, were classified as "late generation hybrids" (or non-V. vinifera×V. vinifera hybrids) because of a very diluted hybrid character, that was revealed only by MS methods. Five cultivars, i.e. Aglianico Lasco, Cannella, Coda di Volpe Rossa, Mentuonico, Olivella Nera, were catalogued as purebred V. vinifera. Due to the peculiar anthocyanin profile one variety (Tuccanese) remained unassigned. The methodology is of general applicability to support the process of varietal discrimination on a molecular basis with the objective of classifying autochthonous old grapevine varieties.

Monte Carlo modelling of non-isothermal degradation of two cyanidin-based anthocyanins in aqueous system at high temperatures and its impact on antioxidant capacities.

The non-isothermal degradation of two cyanidin-based anthocyanins, cyanidin-3-glucoside and cyanidin-3-rutinoside, was investigated in aqueous system within the temperature range from 100 to 165 °C, and the degradation kinetics was modelled using Monte Carlo simulation. The two anthocyanins showed different stability, with cyanidin-3-glucoside exhibiting a higher degradation rate than cyanidin-3-rutinoside. The derived degradation rate at the reference temperature of 132.5 °C and activation energy of cyanidin-3-glucoside and cyanidin-3-rutinoside were 0.0047 and 0.0023 s(-1), and 87 and 104 kJ/mol, respectively. The antioxidant capacity of the thermally processed anthocyanins solutions was measured by using ABTS and DPPH assays. Results showed that the antioxidant capacity of the samples remained at the same level during the thermal treatment process under various conditions, i.e., there was no significant difference (P>0.05) in the antioxidant capacity amongst the samples despite their significantly different contents of the two anthocyanins.

Advanced knowledge of three important classes of grape phenolics: anthocyanins, stilbenes and flavonols.

Grape is qualitatively and quantitatively very rich in polyphenols. In particular, anthocyanins, flavonols and stilbene derivatives play very important roles in plant metabolism, thanks to their peculiar characteristics. Anthocyanins are responsible for the color of red grapes and wines and confer organoleptic characteristics on the wine. They are used for chemotaxonomic studies and to evaluate the polyphenolic ripening stage of grape. They are natural colorants, have antioxidant, antimicrobial and anticarcinogenic activity, exert protective effects on the human cardiovascular system, and are used in the food and pharmaceutical industries. Stilbenes are vine phytoalexins present in grape berries and associated with the beneficial effects of drinking wine. The principal stilbene, resveratrol, is characterized by anticancer, antioxidant, anti-inflammatory and cardioprotective activity. Resveratrol dimers and oligomers also occur in grape, and are synthetized by the vine as active defenses against exogenous attack, or produced by extracellular enzymes released from pathogens in an attempt to eliminate undesirable toxic compounds. Flavonols are a ubiquitous class of flavonoids with photo-protection and copigmentation (together with anthocyanins) functions. The lack of expression of the enzyme flavonoid 3',5'-hydroxylase in white grapes restricts the presence of these compounds to quercetin, kaempferol and isorhamnetin derivatives, whereas red grapes usually also contain myricetin, laricitrin and syringetin derivatives. In the last ten years, the technological development of analytical instrumentation, particularly mass spectrometry, has led to great improvements and further knowledge of the chemistry of these compounds. In this review, the biosynthesis and biological role of these grape polyphenols are briefly introduced, together with the latest knowledge of their chemistry.

Photostability of low cost dye-sensitized solar cells based on natural and synthetic dyes.

This paper deals with the use of some natural pigments as well as synthetic dyes to act as sensitizers in dye-sensitized solar cells (DSSCs). Anthocyanin dye extracted from rosella (Hibiscus sabdariffa L.) flowers, the commercially available textile dye Remazole Red RB-133 (RR) and merocyanin-like dye based on 7-methyl coumarin are tested. The photostability of the three dyes is investigated under UV-Vis light exposure. The results show a relatively high stability of the three dyes. Moreover, the photostability of the solid dyes is studied over the TiO2 film electrodes. A very low decolorization rates are recorded as; rate constants k=1.6, 2.1 and 1.9×10(-3)min(-1) for anthocyanin, RR and coumarin dyes, respectively. The stability results favor selecting anthocyanin as a promising sensitizer candidate in DSSCs based on natural products. Dyes-sensitized solar cells are fabricated and their conversion efficiency (η) is 0.27%, 0.14% and 0.001% for the anthocyanin, RR and coumarin dyes, respectively. Moreover, stability tests of the sealed cells based on anthocyanin and RR dyes are done under continuous light exposure of 100mWcm(-2), reveals highly stable DSSCs.

A study of controlled uptake and release of anthocyanins by oxidized starch microgels.

Anthocyanins are well-known antioxidants, but they are sensitive to environmental conditions. Herein we used oxidized starch microgel to prevent their early degradation and deliver them to the target place. The aim of this study was to investigate the uptake and the release ability of anthocyanins by the oxidized starch microgels and measure their in vitro gastrointestinal release. The gels were made of oxidized potato starch polymers, which were chemically cross-linked by sodium trimetaphosphate (STMP). In this study, the uptake and release behaviors of anthocyanins by starch microgel were investigated under various pH and salt concentrations. The microgel of high degree of oxidation and high cross-link density had a high uptake capacity for anthocyanins at low pH and salt concentration; 62 mg anthocyanins had been absorbed per gram of dry DO100% (degree of oxidation 100%) microgel at pH 3 with ionic strength 0.05M. The in vitro study of the release was investigated under stimulated gastrointestinal fluid. The anthocyanins were identified and quantified by UV/vis detection. The results indicated that the oxidized starch microgels had a potential for being a carrier system for protecting anthocyanins from degradation in the upper gastric tract and for delivering them to the intestine. This paper provides a good reference for an intestinal-targeted delivery system of vulnerable functional ingredients by oxidized starch microgel.

Systematic qualitative and quantitative assessment of anthocyanins, flavones and flavonols in the petals of 108 lotus (Nelumbo nucifera) cultivars.

Petal colour is one of the major characteristics that determine the ornamental value of lotus. To assess the contribution of different flavonoids to this character, composition and content of anthocyanins, flavones and flavonols were analysed through high performance liquid chromatography coupled with photodiode array detection tandem electrospray ionisation triple quad mass spectrometry in 108 lotus cultivars with red, pink, yellow, white and red/white pied petal colours. Totally, five anthocyanins and fourteen flavones and flavonols were detected and quantified. In general, the yellow, white and pied species hardly contained any anthocyanins; red cultivars contain more than pink cultivars. Among the five anthocyanins, malvidin 3-O-glucoside was the most abundant one in all the cultivars that contain anthocyanin. The fourteen flavones and flavonols belonged to four groups based on their aglycones. Except for the yellow cultivars, kaempferol-derivatives were the most abundant one. These data might be helpful in lotus breeding for different colours.