Semisynthesis of Betaxanthins from Purified Betacyanin of Opuntia dillenii sp.: Color Stability and Antiradical Capacity.

The availability of pure individual betalains in sufficient quantities which permit deeper understanding is still a challenge. This study investigates the high-yielding semisynthesis of betaxanthins using betalamic acid from a natural source (Opuntia dillenii), followed by condensation with ʟ-amino acids and further purification. Moreover, the color stability of the four synthesized individual betaxanthins, namely proline (ʟ-ProBX), alanine (ʟ-AlaBX), leucine (ʟ-LeuBX), and phenylalanine (ʟ-PheBX) betaxanthins, was investigated at different pHs. Their relative contribution to free radical scavenging was also scrutinized by TEAC and DPPH. ʟ-AlaBX and ʟ-LeuBx showed a significantly (p < 0.05) higher antioxidant activity, whereas ʟ-ProBX was the most resistant to the hydrolysis of betaxanthin and hence the least susceptible to color change. The color stability was strongly influenced by pH, with the color of ʟ-ProBX, ʟ-LeuBX, and ʟ-AlaBX at pH 6 being more stable, probably due to the easier hydrolysis under acid conditions. The semisynthesis and purification allowed us to have available remarkable quantities of pure individual betaxanthins of Opuntia dillenii for the first time, and to establish their color properties and antioxidant capacity. This study could be a step forward in the development of the best natural food colorant formulation, based on the betalain structure, which is of special interest in food technology.

Mechanism of Antioxidant Activity of Betanin, Betanidin and Respective C15-Epimers via Shape Theory, Molecular Dynamics, Density Functional Theory and Infrared Spectroscopy.

Betanin and betanidin are compounds with extensive interest; they are effectively free radical scavengers. The present work aims to elucidate the differences between the mechanism of the antioxidant activity of betanin, betanidin, and their respective C15-epimers. Shape Theory establishes comparisons between the molecules' geometries and determines parallelisms with the descriptors BDE, PA, ETE IP, PDE, and infrared spectra (IR) obtained from the molecule simulations. Furthermore, the molecules were optimized using the B3LYP/6-31+G(d,p) protocol. Finally, the molecular docking technique analyzes the antioxidant activity of the compounds in the complex with the therapeutic target xanthine oxidase (XO), based on a new proposal for the geometrical arrangement of the ligand atoms in the framework of Shape Theory. The results obtained indicate that the SPLET mechanism is the most favorable in all the molecules studied and that the first group that loses the hydrogen atom in the four molecules is the C17COOH, presenting less PA the isobetanidin. Furthermore, regarding the molecular docking, the interactions of these compounds with the target were favorable, standing out to a greater extent the interactions of isobetanidin with XO, which were analyzed after applying molecular dynamics.

Influence of gelation on the retention of purple cactus pear extract in microencapsulated double emulsions.

A purple cactus pear (Opuntia ficus-indica) extract (CP) was encapsulated in double emulsions (DE) gelled with gelatin (DE-CP-G) and with gelatin and transglutaminase (DE-CP-GT), as well as in a DE with a liquid external aqueous phase (DE-CP), in order to study the retention of betanin as colorant agent. Both gelled DEs showed a predominantly elastic behavior, in contrast with DE-CP. The degradation rate constant of betanin was significantly higher in DE-CP-GT (90.2 x 10-3 days-1) than in DE-CP-G (11.0 x 10-3 days-1) and DE-CP (14.6 x 10-3 days-1) during cold-storage (4 °C). A shift towards yellow color was found in all the systems during cold-storage (4 °C) and after thermal treatment (70°C/30 min), especially in DE-CP-GT, denoting a higher degradation of betanin. Betalamic acid, cyclo-Dopa 5-O-ß-glucoside, 17-decarboxy-betanin and neobetanin were identified by UHPLC-MS/MS as degradation products of betanin.

Betanin, a Natural Food Additive: Stability, Bioavailability, Antioxidant and Preservative Ability Assessments.

Betanin is the only betalain approved for use in food and pharmaceutical products as a natural red colorant. However, the antioxidant power and health-promoting properties of this pigment have been disregarded, perhaps due to the difficulty in obtaining a stable chemical compound, which impairs its absorption and metabolism evaluation. Herein, betanin was purified by semi-preparative HPLC-LC/MS and identified by LC-ESI(+)-MS/MS as the pseudomolecular ion m/z 551.16. Betanin showed significant stability up to -30 °C and mild stability at chilling temperature. The stability and antioxidant ability of this compound were assessed during a human digestion simulation and ex vivo colon fermentation. Half of the betanin amount was recovered in the small intestine digestive fluid and no traces were found after colon fermentation. Betanin high antioxidant ability was retained even after simulated small intestine digestion. Betanin, besides displaying an inherent colorant capacity, was equally effective as a natural antioxidant displaying peroxy-radical scavenger ability in pork meat. Betanin should be considered a multi-functional molecule able to confer an attractive color to frozen or refrigerated foods, but with the capacity to avoid lipid oxidation, thereby preserving food quality. Long-term supplementation by beetroot, a rich source of betanin, should be stimulated to protect organisms against oxidative stress.

Microencapsulated betacyanin from colored organic quinoa (Chenopodium quinoa Willd.): optimization, physicochemical characterization and accelerated storage stability.

BACKGROUND: Betalains are presently gaining popularity as pigments for use as natural colorants and/or bioactive compounds in functional foods. Quinoa (Chenopodium quinoa Willd.) has been recognized as an extremely nutritious grain and has recently been found to be a novel and good betalain source. Microencapsulation has been studied as a protected-delivery procedure to stabilize betalains. There are no studies about microencapsulation of betacyanins extracted from quinoa using spray-drying technology. RESULTS: Optimal microencapsulation was obtained at a drying temperature of 165 °C, a rotameter air flow rate of 47 mm (940 L h-1 ) and 10% w/w maltodextrin, which produced good encapsulation yield (58.1%) and efficiency (100%). Optimized maltodextrin-betacyanin microcapsules (diameter 4.4 µm) have low moisture (1.64 ± 0.08%) and water activity (0.127 ± 0.006), a betacyanin content of 0.1995 ± 0.0017 g kg-1 and saponin content <0.080 mg kg-1 . The oxygen consumption rate by betacyanin was -4.373 × 10-5 bar min-1 at 80 °C and -6.67 × 10-5 bar min-1 at 90 °C, which was accompanied by fading of the color. CONCLUSION: Microencapsulated betacyanin was optimized by response surface methodology, and its stability was measured under accelerated conditions by oxygen consumption. Microencapsulations contain betacyanin and low saponin concentration, which might confer unique health-promoting properties. © 2018 Society of Chemical Industry.

Microencapsulation of betanin in monodisperse W/O/W emulsions.

Betanin is the main pigment of the food color beetroot red (E162). Due to the fair heat and light stability of E162, this pigment is mainly used in minimally processed packaged food products. Encapsulation increases the stability of betanin, but detailing on the effect of different sources of betanin on the properties and stability of multiple emulsions are scarce. Here we describe the encapsulation of E162, spray-dried beetroot juice and betanin in a monodisperse food-grade water-in-oil-in-water (W/O/W) emulsions by using microchannel emulsification. We compare the tinctorial strength of the encapsulated pigments and investigate the effect of temperature, storage period and pigment concentration on emulsion stability and color. Betanin increases the overall stability of the W/O/W emulsion, reduce the oil droplet size and improve size distribution when compared to the negative control without pigment and to emulsions containing betanin from other sources.

Stability of spray-dried beetroot extract using oligosaccharides and whey proteins.

The properties and stability of spray-dried beetroot extract using maltodextrin (MD), inulin (IN), and whey protein isolate (WPI) as carrier agents were evaluated. The values of moisture, betalains content, and retention were 3.33-4.24%, 348.79-385.47 mg/100 g (dry-basis), and 88.45-95.69%, respectively. Higher values of antioxidant activity were observed for the treatments using WPI. The treatment with inulin alone presented higher hygroscopicity in the moisture adsorption isotherms at 25 °C and lower thermal stability when evaluating the thermogravimetric curves. When stored at 60 °C, the use of WPI alone conferred lower stability to the beetroot extract powder. In general, the simultaneous use of IN and WPI as carrier agents resulted in good stability of the beetroot extract powder, representing an opportunity for innovation in food products.

Fenton Discoloration of Ultrasonicated Purple Cactus Pear Juice.

The aim of this study was to evaluate the stability of color, betaxanthin, and betacyanin pigments in the presence of Cu(II)-dependent hydroxyl radicals (HO•) from ultrasonicated purple cactus pear juice at amplitudes of 40%, 60%, and 80%, in comparison to untreated sample. L* parameter of juice treated at 40% and 80% amplitude for 25 and 15 min, respectively (11.3 and 9.3, respectively), were significantly higher compared to the control; b* and hue parameters of juice treated at 80%, 25 min showed values of 1.7 and 0.1, respectively. Color differences (ΔE) were lower (<3) for juices treated at high amplitude (80%) and short times (3-5 min). Juice treated at 40% 15 min, 60% 25 min, 80% 15 and 25 min presented high values of betacyanins (281.7 mg·L-1, 255.9 mg·L-1, 294.4 mg·L-1, and 276.7 mg·L-1, respectively). Betaxanthin values were higher in the juices treated at 40% 5 min and 80% 15 and 25 min (154.2 mg·L-1, 135.2 mg·L-1, and 128.5 mg·L-1, respectively). Purple cactus pear juice exhibited significant chelating activity of copper ions and great stability when exposed to HO•.

Effect of extrusion cooking on bioactive compounds in encapsulated red cactus pear powder.

Red cactus pear has significant antioxidant activity and potential as a colorant in food, due to the presence of betalains. However, the betalains are highly thermolabile, and their application in thermal process, as extrusion cooking, should be evaluated. The aim of this study was to evaluate the effect of extrusion conditions on the chemical components of red cactus pear encapsulated powder. Cornstarch and encapsulated powder (2.5% w/w) were mixed and processed by extrusion at different barrel temperatures (80, 100, 120, 140 °C) and screw speeds (225, 275, 325 rpm) using a twin-screw extruder. Mean residence time (trm), color (L*, a*, b*), antioxidant activity, total polyphenol, betacyanin, and betaxanthin contents were determined on extrudates, and pigment degradation reaction rate constants (k) and activation energies (Ea) were calculated. Increases in barrel temperature and screw speed decreased the trm, and this was associated with better retentions of antioxidant activity, total polyphenol, betalain contents. The betacyanins k values ranged the -0.0188 to -0.0206/s and for betaxanthins ranged of -0.0122 to -0.0167/s, while Ea values were 1.5888 to 6.1815 kJ/mol, respectively. The bioactive compounds retention suggests that encapsulated powder can be used as pigments and to provide antioxidant properties to extruded products.

Microencapsulation of pulp and ultrafiltered cactus pear (Opuntia ficus-indica) extracts and betanin stability during storage.

Pulp (CP) and ultrafiltered (UF) cactus pear extracts were encapsulated with Capsul (C) by applying a central composite design (CP-C and UF-C systems) by spray-drying. To evaluate the effect of the extract, microparticles obtained under optimal conditions were characterised and stored at 60 °C. Betacyanin and betaxanthin encapsulation efficiency reached values above 98% for both systems studied. This efficiency was attributed to strong interactions between betalains and the polymer. Betalain degradation in CP-C and UF-C microparticles followed pseudo-first order kinetics. The betacyanin degradation rate constant was significantly higher for CP-C than for UF-C. These results suggested that the mucilage or higher sugar content of CP increased the hygroscopicity of the CP-C microparticles, leading to the degradation of betalain. The hydrolysis pathway was the main mechanism of betanin degradation during microparticle storage. These results demonstrate the potential utility of both CP-C and UF-C microparticles as natural colourants for healthy foods.