betalains and betaxanthin

Currently, the demand for natural colorants is increasing instead of synthetic colorants for foodstuff, because they are harmless to human health. Betalain is group of compounds containing nitrogen and water soluble pigment. Betalain is classified into two main classes, betacyanin which is the condensation of betalamic acid with cyclo-DOPA and betaxanthin which is the conjugation of amino acid or amines with betalamic acid. They are used to color various foods and medicines. Betalain is different from anthocyanin because betalains contain nitrogen in their structures. It is interesting to hear that betalains and anthocyanins are individually significant but they have not seen together in the same plant. Their stability influenced by various factors such as, temperature, pH, water activity and light. In this review basic chemistry of betalains, classes, subclasses, their sources and biosynthesis, factors affecting their stability, health and food industry applications are discussed. Moreover, mentioned work signifies the potent anticancer, antioxidant and antimalarial activities of betalains, furthermore provides a help to do more scientific work on it.

Topics: Antimalarials; Antioxidants; Betacyanins; Betalains; Dihydroxyphenylalanine; Food Coloring Agents; Humans; Picolinic Acids; Pyridines

This study presents methods that can be used to assess the health quality of products containing betalains. The paper compares and verifies data on the phytochemical composition of three different pigmented beetroot cultivars using spectrophotometric, HPLC-DAD, HPTLC and LC-Q-Orbitrap-HRMS techniques. Additionally, we compared the total antioxidant activity in both the cell-free and cellular systems. Betalain contribution to antioxidant activity was also determined using post-column derivatization and it was found that in the case of red beetroot it is about 50%. Photometric measurements are recommended for a simple and inexpensive analysis of the total betacyanin and betaxanthin content. Liquid chromatography techniques produced more precise information on phytochemical composition in the tested samples. The combination of liquid chromatography with high-resolution mass spectrometry produced the largest amount of quantitative and qualitative data; in beetroot samples sixty-four phytochemicals have been identified therefore, this approach is recommended for more detailed metabolomics studies.

Topics: Antioxidants; Beta vulgaris; Betacyanins; Betalains; Chromatography, High Pressure Liquid; Chromatography, Liquid; Food Analysis; HT29 Cells; Humans; Mass Spectrometry; Phytochemicals; Picolinic Acids; Plant Extracts; Software

Reduction of bioactive compounds sensitive to heat, light and oxygen could be attributed to drying. The effectiveness of microwave pretreatment at 525 or 420 W and the ohmic heating at 17.5 V/cm over the properties of beetroot powder were compared. This study aimed to develop novel hybrid drying methods. The effects of microwave and ohmic heating pre-treatment and subsequent microwave-convection drying were studied. Several investigations were performed, such as phenolic content, antioxidant activity, betalains content and color. The samples pretreated by microwave have registered higher polyphenols content and antioxidant capacity than those ohmically heated. The ohmic heating pretreated samples registered highest values for ΔL = 7.33-7.65 and ΔH = 8.18-10.02. Confocal microscopy reveals that the MW heating favors cellular lysis and cell content agglutinates. In conclusion, even if the MW preheating has certain disadvantages, in some cases it provides increased bioavailability generated by the vegetal cell disruption and the release of the bioactive compounds.

Topics: Antioxidants; Beta vulgaris; Betacyanins; Betalains; Color; Convection; Desiccation; Hot Temperature; Microwaves; Picolinic Acids; Polyphenols; Powders

An improved methodology of achieving an accurate separation of pure fractions of betacyanins and betaxanthins from Ullucus tuberosus Caldas has been carried out. For that purpose, an in-depth chemical identification of each betalain fraction using HPLC-DAD-ESI-MS was developed. This procedure allowed to evaluate the fractionation efficiency and also identify a large number of betalains, most of which have not been described so far in this raw material: betanidin- and isobetanidin-5-O-(4'-O-malonyl-β-glucoside), 2-decarboxy-phyllocactin, betanidin- and isobetanidin-6-O-(6'-O-feruloyl)-β-glucoside (gomphrenin and isogomphrenin III), dehydro-phyllocactin and isophyllocactin, and arginine and glycine-betaxanthins (portulacaxanthin III). Moreover, the availability of pure betalain fractions by the proposed methodology permitted to establish the total betalain content and the antioxidant activity of both separated betacyanin and betaxanthin fractions of ulluco for the first time. The results suggest Ullucus tuberosus as an underutilized food bioactive source with a high concentration of total betaxanthins (21.8 μg indicaxanthin/g fresh ulluco) and betacyanins (44.5 μg betanin/g fresh ulluco), strongly correlated to the Folin-Ciocalteau reduction capacity.

Topics: Betacyanins; Betalains; Betaxanthins; Chromatography, High Pressure Liquid; Picolinic Acids

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.

Topics: Antioxidants; Betacyanins; Betalains; Betaxanthins; Cactaceae; Cooking; Food Handling; Picolinic Acids; Pigments, Biological; Polyphenols; Powders; Temperature

The aim of the present study is to compare three cultivars of prickly pear fruits ("Sanguigna" red, "Sulfarina" yellow and "Muscaredda" white) regarding the quality parameters of antioxidant activity, phenolic compounds, betalains and ascorbic acid (vitamin C). Depending on the crop operation, these cultivars are represented by "Agostane" and "Bastardoni" and are located at an altitude between 150 and 750 m, above sea level. Their antioxidant activity was evaluated by ORAC assay. Total phenolic compounds, betalains and ascorbic acid recovered from pulp juice, were determined by a spectrophotometric analysis. The results indicate that the different cultivars of prickly pear possess antioxidant activity in function of the type of the adopted practice. These fruits were derived from the practice of scozzolatura, by dropping the berries to encourage a second bloom of the plant. Among the "Bastardoni", the "Sulfarina" possesses the highest antioxidant activity.

Topics: Antioxidants; Ascorbic Acid; Betalains; Fruit; Opuntia; Phytochemicals; Picolinic Acids; Pigments, Biological; Plant Extracts; Polyphenols; Spectrophotometry

Betalains are plant pigments with high antioxidant and free radical scavenging activities. While basal activity exists in all betalains, the dihydroxylated molecules present the highest TEAC values of the family of compounds. However, their lability limits possible applications. This work reports the encapsulation of the most active pigments, the yellow miraxanthin V and the violet betanidin in edible matrixes of chitosan and maltodextrin. An appropriate spray-drying procedure is described, with an inlet air temperature of 140 °C. The resulting particles were characterized by scanning electron microscopy, and powder color was analyzed by spectrophotometry using an integrating sphere. Stability of the bioactive compounds was followed by high-performance liquid chromatography, and it was highly promoted by encapsulation, with limited pigment loss after six months' storage. Particles retained the antioxidant and antiradical activities of the soluble pigments measured under the FRAP and ABTS radical assays. A combination of miraxanthin V and betanidin in variable proportions provides a bright palette of encapsulated powders of different colors suitable for food applications.

Topics: Antioxidants; Betalains; Chitosan; Chromatography, High Pressure Liquid; Chromatography, Ion Exchange; Color; Food Handling; Microscopy, Electron, Scanning; Picolinic Acids; Polysaccharides; Powders; Spectrophotometry

Tyrosinase or polyphenol oxidase (EC 1.14.18.1) is one of the key enzymes for the biosynthesis of natural pigment betalains. These are an important class of water-soluble pigments, characteristic of plants belonging to the order Caryophyllales. In this work, dopamine-betaxanthin (also known as miraxanthin V) is reported as the pigment responsible for the bright coloration in yellow flowers of Portulaca oleracea (common purslane). The natural pigment is purified, and used as a substrate for the catecholase (diphenolase) activity of the enzyme tyrosinase. A new, continuous method to follow the activity is developed based on the fluorescent properties of the betaxanthin. Fluorescence of the enzyme activity derived products is reported for the first time. Relevance of the fluorescent phenomenon is discussed based on fluorescence images and the description of a physiological inner filter effect present in flowers of P. oleracea. The first description of the betalain content in flower pistils is also provided.

Topics: Betalains; Chromatography, High Pressure Liquid; Dopamine; Flowers; Fluoresceins; Monophenol Monooxygenase; Ouabain; Picolinic Acids; Portulaca; Spectrometry, Fluorescence

In the present study, the betaxanthin (bx) and betacyanin patterns of differently coloured inflorescences from Gomphrena globosa L. and Bougainvillea sp. have been investigated in detail by applying reversed phase high-performance liquid chromatography-diode array detection (HPLC-DAD) coupled with positive ion electrospray mass spectrometry. Histidine-bx was found to be the predominant betaxanthin of Gomphrena globosa inflorescences. Furthermore, arginine-bx was detected as a novel betaxanthin, which to the best of our knowledge has not been reported as a pigment that occurs naturally so far. Dopa-bx was the major betaxanthin of Bougainvillea sp., although several minor betaxanthins were also present, including lysine-bx and putrescine-bx, novel betaxanthins hitherto not observed naturally. Remarkable differences in the betacyanin patterns between the purple, red and orange varieties were observed for both Gomphrena and Bougainvillea inflorescences. Hence, both the betacyanin profiles and the relative betaxanthin:betacyanin ratios determine the broad colour palette of Gomphrena petals and Bougainvillea bracts.

Topics: Betalains; Chromatography, High Pressure Liquid; Picolinic Acids; Pigments, Biological; Plants; Spectrometry, Mass, Electrospray Ionization

Amino acids and amines are the precursors of betalains. Therefore, the profiles of free amino compounds in juices obtained from cactus pears [Opuntia ficus-indica (L.) Mill. cv. Bianca, cv. Gialla, and cv. Rossa], pitaya fruits [Selenicereus megalanthus (K. Schumann ex Vaupel) Moran, Hylocereus polyrhizus (Weber) Britton & Rose, and Hylocereus undatus (Haworth) Britton & Rose], and in extracts from differently colored Swiss chard [Beta vulgaris L. ssp. cicla (L.) Alef. cv. Bright Lights] petioles and red and yellow beets (B. vulgaris L. ssp. vulgaris var. conditiva Alef. cv. Burpee's Golden) were investigated for the first time. Amino compounds were derivatized with propyl chloroformate. While gas chromatography (GC) with mass spectrometry was used for peak assignment, GC flame ionization detection was applied for quantification of individual compounds. Whereas proline was the major free amino compound of cactus pear and pitaya fruit juices, glutamine dominated in Swiss chard stems and beets, respectively. Interestingly, extremely high concentrations of dopamine were detected in Swiss chard stems and beets. Furthermore, the cleavage of betaxanthins caused by derivatization in alkaline reaction solutions is demonstrated for the first time. Amino acids and amines thus released might increase the actual free amino compound contents of the respective sample. To evaluate the contribution of betaxanthin cleavage to total amino acid and amine concentration, isolated betaxanthins were derivatized according to the "EZ:faast" method prior to quantification of the respective amino compounds released. On a molar basis, betaxanthin contribution to overall amino compound contents was always below 6.4%.

Topics: Amines; Amino Acids; Beta vulgaris; Betalains; Cactaceae; Chromatography, Gas; Dopamine; Fruit; Glutamine; Mass Spectrometry; Opuntia; Picolinic Acids; Vegetables

Tyrosinase or polyphenol oxidase (EC 1.14.18.1) is the key enzyme in melanin biosynthesis and in the enzymatic browning of fruits and vegetables. The role of tyrosinase in the secondary metabolism of plants still remains unclear, but its implication in betalain biosynthesis has been proposed. Betalains are an important class of water-soluble pigments, characteristic of plants belonging to the order Caryophyllales. In this article, the betaxanthins, tyrosine-betaxanthin (portulacaxanthin II) and dopaxanthin, are reported to be physiological substrates for tyrosinase. The direct activity of tyrosinase on selected betaxanthins is characterized in depth, and conversion of tyrosine-betaxanthin to dopaxanthin and its further oxidation to a series of compounds are described. Identity of the reaction products was studied by high-performance liquid chromatography and electrospray ionization-mass spectrometry. Masses determined for the reaction products were the same in all cases, 389 m/z ([M + H]+) and equal to that determined for betanidin. Data indicate that dopaxanthin-quinone is obtained and evolves to more stable species by intramolecular cyclization. Kinetic parameters for tyrosinase acting on dopaxanthin were evaluated, showing a high affinity for this substrate (K(m) = 84.3 microM). The biosynthetic scheme of betalains is reviewed and a branch is proposed based on the description of physiological substrates for tyrosinase. Lampranthus productus, Glottiphylum oligocarpum, and Glottiphylum pigmaeum are described as sources of stereopure (2S/S)-dopaxanthin.

Topics: Betalains; Kinetics; Monophenol Monooxygenase; Picolinic Acids; Plants; Quaternary Ammonium Compounds; Substrate Specificity

Tyrosinase or polyphenol oxidase (EC 1.14.18.1) is the key enzyme responsible for melanin biosynthesis and for the enzymatic browning of fruits and vegetables. Although the function of tyrosinase in the secondary metabolism of plants remains unclear, it has been proposed that the enzyme plays a role in the betalain biosynthetic pathway. Betalains are an important class of water-soluble pigments, characteristic of plants belonging to the order Caryophyllales. In the present work, the betaxanthins tyramine-betaxanthin (miraxanthin III) and dopamine-betaxanthin (miraxanthin V) are reported as new natural substrates for tyrosinase. The result of the diphenolase activity of the enzyme on dopamine-betaxanthin was a series of products identified by HPLC and ESI-MS as quinone-derivatives. Data indicate that dopamine-betaxanthin-quinone is obtained and evolves to more stable species by intramolecular cyclization. The kinetic parameters evaluated for the diphenolase activity were V(m) = 74.4 microM min(-1), K(m) = 94.7 microM. Monophenolase activity on tyramine-betaxanthin yielded the same compounds in the absence of a reducing agent, but when ascorbic acid was present enzymatic conversion to dopamine-betaxanthin could be found. For the first time, kinetic characterization of the monophenolase activity of tyrosinase on betaxanthins is provided (V(m) = 10.4 microM min(-1) and K(m) = 126.9 microM) and a lag period is described and analyzed according to the mechanism of action of the enzyme. The high affinity shown by tyrosinase for these substrates may be indicative of a previously unconsidered physiological role in betalain metabolism. A possible mechanism for the formation of 2-descarboxy-betacyanins from tyramine-betaxanthin by tyrosinase is also discussed.

Topics: Agaricales; Betalains; Dopamine; Kinetics; Models, Chemical; Monophenol Monooxygenase; Oxidation-Reduction; Picolinic Acids; Tyramine

Betaxanthins are natural water-soluble yellow pigments present in plants of the order Caryophyllales. The native fluorescence of these compounds is extensively characterized in this work, with study of the fluorescent properties of 14 different betaxanthins. All the species showed a similar behavior, with excitation maxima between 463 and 475 nm and emission maxima between 506 and 515 nm. Thus, betaxanthins absorb light corresponding to the blue color and emit visible green light. Similarities in excitation and emission spectra point to the responsibility of betalamic acid in fluorescence. The influence of the amine moiety is discussed. For the first time fluorescent properties of betaxanthins are applied to the detection of these pigments after separation by high-performance liquid chromatography. Wavelengths used were 460 nm for excitation and 510 nm for emission, which were suitable for detecting the native fluorescence of all the pigments assayed. Calibration was performed in each case and it exhibited linearity within the range considered, at least 20 microM. The lowest detection limit was 100 nM, corresponding to betaxanthins derived from methionine sulfoxide and leucine. Fluorescence detection was applied to the quantification of betaxanthins present in Carpobrotus acinaciformis. The present work opens up new possibilities for the analysis of betaxanthins by improving existing protocols through fluorescence detection.

Topics: Betacyanins; Betalains; Caryophyllaceae; Chromatography, High Pressure Liquid; Indoles; Magnoliopsida; Picolinic Acids; Pyridines; Spectrometry, Fluorescence