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At least 19 recordsLinked to original sources
PubMed2005

Formation of decarboxylated betacyanins in heated purified betacyanin fractions from red beet root (Beta vulgaris L.) monitored by LC-MS/MS.

Mixtures of mono-, bi-, and tridecarboxylated betacyanins together with their corresponding neobetacyanins obtained from Beta vulgaris L. root juice as heating degradation products of betacyanins were identified by high-performance liquid chromatography with tandem mass spectrometry (LC-MS/MS) and diode-array (LC-DAD) detection. Two monodecarboxy-betacyanin pairs of diastereomers were detected after the decarboxylation in ethanolic and aqueous solutions. Generation of 17-decarboxy-betacyanins and 2-decarboxy-betacyanins was suggested, the latter so far never having been attributed to betacyanin thermal degradation products. Other main products of decarboxylation were 2,17-bidecarboxybetanin, its isoform, and 14,15-dehydrogenated (neobetacyanin) derivatives of all the decarboxylated betacyanins. The results of this research are crucial in determining betacyanin degradation mechanisms in juices or extracts of B. vulgaris L. roots and other products containing these pigments.

Beta vulgaris↗
PubMed2006

Effect of tetraalkylammonium salts on retention of betacyanins and decarboxylated betacyanins in ion-pair reversed-phase high-performance liquid chromatography.

The ability of tetraalkylammonium salts to act as ion-pairing agents for betacyanins and mono- as well as bidecarboxylated betacyanins in HPLC on reversed phase is reported. The results indicate substantial and various influences of tetraalkylammonium salt addition to eluent on magnitude and direction of retention time changes of the analytes. The interactions of the tetraalkylammonium cations with the accessible positive and negative charged parts of the analysed molecules at their different level and position of decarboxylation determined the possibility of ion-pair formation. A remarkable positive influence was observed for betacyanins on the basis of strongly enhanced retention of the resulted ion-pairs. In contrast, the 2,17-bidecarboxy-betacyanin retention, in most of the applied conditions, strongly decreased under the impact of the reagents. The effect of the salt concentration on direction of 17-decarboxy-betacyanin and 2,17-bidecarboxy-betacyanin retention changes strongly varied with the eluent pH. The carboxylic group at the C-2 carbon cannot interact with tetraalkylammonium cations as strongly as does the C-17 carboxylic group, leading to different effects in the absence of carboxylic group at the C-2 or C-17 carbon in the molecules.

Betacyanins↗
PubMed2004

Influence of perfluorinated carboxylic acids on ion-pair reversed-phase high-performance liquid chromatographic separation of betacyanins and 17-decarboxy-betacyanins.

The ability of trifluoroacetic acid, pentafluoropropionic acid and heptafluorobutyric acid to act as ion-pairing agents for betacyanins and 17-decarboxy-betacyanins during HPLC analysis on a Luna C18(2) reversed-phase column is reported. While the perfluorinated carboxylic acids affect the retention of both groups of compounds by changing the pH of the mobile phase, the possibility of ion-pair chromatography for 17-decarboxy-betacyanins was noticed. In order to explain the accessibility of the positive charge for the counter-anion in decarboxy-betacyanins, the mesomeric structures of the polymethine system at low pH (around a value of 1.5), when the carboxylic group in the 2 position is protonated, should be taken into consideration.

Betalains↗
PubMed2003

Stimulation of betacyanin synthesis through exogenous methyl jasmonate and other elicitors in suspension-cultured cells of Portulaca.

Betacyanin production in suspension-cultured cells of Portulaca was significantly enhanced by both abiotic and biotic elicitors. Betacyanin levels increased 1.3 and 1.5-fold over the controls in the presence of two abiotic elicitors (20 mumol/L CuSO4 and 100 mumol/L FeEDTA) and increased 1.8 and 1.6-fold in the presence of two biotic elicitors (0.5 mg/L beta-glucan and 0.5 mg/L chitosan). Maximum betacyanin synthesis with the two most effective elicitors was obtained when cultures were treated on day 1 and day 0 by beta-glucan and FeEDTA, respectively. A concentration-dependent response was exhibited by cultures treated with exogenous methyl jasmonate (MJ). MJ alone at 0.1 mumol/L caused a 2.6-fold increase in betacyanin synthesis when administered to the suspension culture on day 3. However, no additive effect on betacyanin accumulation was observed in treatments, which combined MJ and beta-glucan or FeEDTA. Treatment with ibuprofen (IB), an inhibitor of jasmonate biosynthesis, reduced the level of betacyanin in cells cultured in standard medium at all concentrations tested (25, 50, 100 mumol/L). The effect of IB on betacyanin synthesis in the cells treated with MJ or beta-glucan, however, differed with the IB concentration applied. The two higher concentrations (50 and 100 mumol/L) of IB significantly reduced the betacyanin content while the lower concentration (25 mumol/L) did not show an adverse effect on the betacyanin enhancement triggered by MJ or beta-glucan. Our findings suggest that, in suspension-cultured cells of Portulaca, an MJ-mediated signal transduction pathway prominently exists in betacyanin synthesis. This pathway seems to act antagonistically towards beta-glucan-mediated signaling. As far as we know this is the first report on the elevation of betacyanin level by jasmonate or other elicitors in cell suspension cultures.

Acetates↗
PubMed2001

Identification and distribution of simple and acylated betacyanins in the Amaranthaceae.

Red-colored plants in the family Amaranthaceae are recognized as a rich source of diverse and unique betacyanins. The distribution of betacyanins in 37 species of 8 genera in the Amaranthaceae was investigated. A total of 16 kinds of betacyanins were isolated and characterized by HPLC, spectral analyses, and MS. They consisted of 6 simple (nonacylated) betacyanins and 10 acylated betacyanins, including 8 amaranthine-type pigments, 6 gomphrenin-type pigments, and 2 betanin-type pigments. Acylated betacyanins were identified as betanidin 5-O-beta-glucuronosylglucoside or betanidin 6-O-beta-glucoside acylated with ferulic, p-coumaric, or 3-hydroxy-3-methylglutaric acids. Total betacyanin content in the 37 species ranged from 0.08 to 1.36 mg/g of fresh weight. Simple betacyanins (such as amaranthine, which averaged 91.5% of total peak area) were widespread among all species of 8 genera. Acylated betacyanins were distributed among 11 species of 6 genera, with the highest proportion occurring in Iresine herbstii (79.6%) and Gomphrena globosa (68.4%). Some cultivated species contained many more acylated betacyanins than wild species, representing a potential new source of these pigments as natural colorants.

Acylation↗
PubMed2000

Production of betacyanins by a cell suspension culture of table beet (Beta vulgaris L.).

A cell suspension culture of table beet (Beta vulgaris L.) was established for efficient betacyanin production from violet callus induced from the hypocotyls of aseptic seedlings. This suspension culture produced large amounts of betacyanins. The betacyanin content increased with increasing cell growth during the log phase. Reducing the total nitrogen concentration (30 mM) and modifying the ratio of ammonium to nitrate (1:14) resulted in an increased betacyanin content. Supplementation of Fe2+ to the LS medium also promoted betacyanin production. The maximal betacyanin yield was achieved with a 2 mM Fe2+ concentration. Combining these conditions, we established a revised LS medium to improve betacyanin productivity (250 mg/l for a 14-day culture).

Carbocyanines↗
PubMed2002

New medium composition for high betacyanin production by a cell suspension culture of table beet (Beta vulgaris L.).

The effect of a revised Linsmaier-Skoog (LS) medium on betacyanin production was investigated in suspension cultures of table beet (Beta vulgaris L.). The effects of a high iron concentration and low concentration of zinc on betacyanin production were not cumulative. The composition of the new revised medium for high betacyanin production was established by reducing the concentration of inorganic nitrogen (30 mM), modifying the ratio of ammonium to nitrate (1:14), reducing the concentration of zinc (0.0003 mM), and removing copper and cobalt. The revised LS medium enabled the maximum betacyanin yield of 550 mg/l to be obtained from a 14-day culture. This medium promoted the betacyanin production in three types of cell line differing in the betacyanin productivity. The betacyanin productivity (40 mg/l x day) was higher than that quoted in any other previous reports.

Beta vulgaris↗
PubMed2005

Generation of decarboxylated and dehydrogenated betacyanins in thermally treated purified fruit extract from purple pitaya (Hylocereus polyrhizus) monitored by LC-MS/MS.

Pigments of purple pitaya [Hylocereus polyrhizus (F.A.C. Weber) Britton and Rose] fruits were submitted to extraction and were decarboxylated during heating experiments in acidified ethanolic and aqueous solutions. Groups of betacyanins with different decarboxylation levels were identified in the heating products by LC-DAD and LC-MS/MS. The main decarboxylation products were 2-decarboxy-betacyanins, 17-decarboxy-betacyanins, and 2,17-bidecarboxy-betacyanins. The structures of other compounds were assigned to 2,15,17-tridecarboxy-betacyanins and 14,15-dehydrogenated derivatives (neo-derivatives) of all decarboxylated betacyanins found.

Cactaceae↗
PubMed2006

Rapid identification of betacyanins from Amaranthus tricolor, Gomphrena globosa, and Hylocereus polyrhizus by matrix-assisted laser desorption/ionization quadrupole ion trap time-of-flight mass spectrometry (MALDI-QIT-TOF MS).

Natural betacyanins have attracted great attention as food colorants and potential antioxidants. Matrix-assisted laser desorption/ionization quadrupole ion trap time-of-flight mass spectrometry (MALDI-QIT-TOF MS) is a new and powerful technique for the identification of low molecular weight compounds. This study is the first to employ MALDI-QIT-TOF MS to rapidly identify, within a few minutes, a great number of betacyanins in crude extracts from Amaranthus tricolor seedlings, Gomphrena globosa flowers, and Hylocereus polyrhizus fruits. The fresh crude extract samples without any purification were directly used for MALDI-QIT-TOF MS analysis with 2,5-dihydroxybenzoic acid as a matrix. The MS2 and MS3 spectrometric data acquired could provide important characteristic information for structural elucidation of the betacyanins. Fourteen free and acylated betacyanins, belonging to amaranthin-type, betanin-type, and gomphrenin-type betacyanins, respectively, were identified. However, the related isomers should be differentiated with the aid of HPLC.

Amaranthaceae↗
PubMed2001

Effect of zinc deficiency on betacyanin production in a cell suspension culture of table beet (Beta vulgaris L.).

The effect of microelements in the Linsmaier-Skoog (LS) medium on betacyanin production was investigated in suspension cultures of table beet (Beta vulgaris L.). Removing zinc from the medium resulted in a high betacyanin content of the cells, the betacyanin content of the cells decreasing with increasing zinc concentration in the medium. The betacyanin content of cells cultured in the medium without zinc was twice as high as that in the medium containing 0.03 mM of zinc. In the revised LS medium without zinc, the maximum betacyanin yield was obtained of 590 mg/l from a 21-day culture.

Betalains↗
PubMed2001

Formation and occurrence of dopamine-derived betacyanins.

In light of the fact that the main betaxanthin (miraxanthin V) and the major betacyanin (2-descarboxy-betanidin) in hairy root cultures of yellow beet (Beta vulgaris L.) are both dopamine-derived, the occurrence of similar structures for the minor betacyanins was also suggested. By HPLC comparison with the betacyanins obtained by dopamine administration to beet seedlings, enzymatic hydrolysis, LCMS and 1H NMR analyses, the minor betacyanins from hairy roots were identified as 2-descarboxy-betanin and its 6'-O-malonyl derivative. A short-term dopamine administration experiment with fodder beet seedlings revealed that the condensation step between 2-descarboxy-cyclo-Dopa and betalamic acid is the decisive reaction, followed by glucosylation and acylation. From these data a pathway for the biosynthesis of dopamine-derived betalains is proposed. Furthermore, the occurrence of these compounds in various cell and hairy root cultures as well as beet plants (Fodder and Garden Beet Group) is shown.

Betalains↗
PubMed1999

Light-induced betacyanin and flavonol accumulation in bladder cells of Mesembryanthemum crystallinum.

Treatment of the halophyte Mesembryanthemum crystallinum L. (ice plant) (Aizoaceae) with high intensities of white light resulted in a rapid cell-specific accumulation of betacyanins and flavonoids with 6-methoxyisorhamnetin 3-O-¿[(2"'-E-feruloyl)-3"'-O-(beta-D- glucopyranosyl)](2"-O-beta-D-xylopyranosyl)]-beta-D-glucopyranoside (mesembryanthin) as the predominant component, within bladder cells of the leaf epidermis. Induced accumulation of these metabolites was first detected 18 h after the initiation of light treatment in bladder cells located at the tip of young leaves followed by the bladder cells located on the epidermis of fully expanded leaves. UV-A light apparently is sufficient to induce accumulation of betacyanins and flavonoids. Application of 2-aminoindan 2-phosphonic acid, a specific inhibitor of phenylalanine ammonia-lyase (PAL; EC 4.3.1.5), not only inhibited the accumulation of flavonoids but also reduced betacyanin formation. Based on these observations we suggest these bladder cells as a model system to study regulation of betacyanin and flavonoid biosyntheses.

Anthocyanins↗
PubMed2003

Color properties and stability of betacyanins from Opuntia fruits.

The colorant properties of pigments from Opuntia stricta, Opuntia undulata, and Opuntia ficus-indicafruits were studied. The pigments were extracted with different solvents and identified by high-performance liquid chromatography. On the basis of their visible light spectra, the pigments were identified as betalains. In O. undulata and O. ficus-indica fruits, both betacyanins and betaxantins were identified, while in O. stricta fruits only betacyanins (betanin and isobetanin) were detected. O. stricta fruits showed the highest betacyanin content (80 mg/100 g fresh fruit). The thermal stability of the pigment extracts was dependent on the pH, with the maximum stability being at pH 5, as expected for betacyanins. At this value and a storage temperature of 4 degrees C, a deactivation half-life time of more than 1 year, with no added stabilizers, was determined. According to these studies, cactus pears from O. stricta may well be considered as a potential source of natural red colorants.

Betalains↗
PubMed1979

Temperature-sensitive Responses of Red Light-dependent Betacyanin Synthesis.

Amaranthus tricolor half-seedlings show a greater accumulation of betacyanin in response to a defined period of red light if given a pretreatment at an elevated temperature (40 C). Red light given before the shift to 40 C is ineffective. The maximum response is achieved after a 2-hour shift to 40 C and if the red light is given 1 hour after return to the germination temperature (25 C). The effect on red light induction of betacyanin synthesis and on fusicoccin induction by these conditions is similar, whereas the increase in cytokinin-dependent synthesis is greater. Both phytochrome-cytokinin synergism and fusicoccin-cytokinin synergism are changed in the same manner by this treatment. Phytochrome and fusicoccin responses are inhibited similarly by carbonyl-cyanide-p-trifluoromethoxy-phenylhydrazone.If the seedlings are again returned to 40 C after the 25 C shift there is an inhibition of betacyanin synthesis. The interpretation of these results is that a shift to 40 C induces the formation of some component necessary for the full expression of phytochrome potential, that for the maximum formation or action of this component it is necessary for the seedlings to spend 1 to 2 hours at a lower temperature (for example 25 C) before red light is given and that for the subsequent processes in betacyanin synthesis an elevated temperature is inhibitory.

Journal Article↗
PubMed2006

Identification of betacyanin and effects of environmental factors on its accumulation in halophyte Suaeda salsa.

Effects of temperature, light, salinity and developmental phases on the accumulation of red pigments in the C(3) halophyte Suaeda salsa were studied, and the physical and chemical characteristics of the red pigments were also analyzed. The results indicate that: these red pigments are insoluble in organic solvents but free in water, the pigments are red-violet and stable under acidic condition while yellow and unstable under alkaline condition, and they absorb the highest value at wavelength near 538 nm, light suppresses their accumulation and enhances their decomposition. These results suggest that these red pigments are betacyanins. Darkness, low temperatures and high salinity enhance betacyanin accumulation in Suaeda salsa, and darkness in the germination phase is one of the most important environmental factors for the betacyanin accumulation.

Betacyanins↗
PubMed1994

Betacyanins from bracts of Bougainvillea glabra.

Betacyanins from the bracts of Bougainvillea glabra were isolated and characterized by a combination of spectroscopic techniques (DAD-HPLC, NMR, LC-MS, GC-MS, electrospray MS, tandem MS) as gomphrenin I (betanidin 6-O-beta-glucoside) and various derivatives of bougainvillein-v (betanidin 6-O-beta-sophoroside), i.e. mono- and diglucosylsophorosides which are acylated with 4-coumaric and caffeic acid (mono- and diesters). Besides the betacyanins, B. glabra bracts accumulated large amounts of flavonols (kaempferol and quercetin conjugates) reaching ratios of flavonol to betacyanin of 1:1.

Betalains↗
PubMed2000

Phenolics and betacyanins in red beetroot (Beta vulgaris) root: distribution and effect of cold storage on the content of total phenolics and three individual compounds.

The distribution of total phenolics and main betacyanins in red beetroot (Beta vulgaris) root was determined. Also, the subsequent effects of cold storage on the content of total phenolics, main betacyanins (betanin and isobetanin), and the main known ferulic acid ester (beta-D-fructofuranosyl-alpha-D-(6-O-(E)-feruloylglucopyranoside) were determined in the peel, which is the root part containing the largest amount of total phenolics. The content of total phenolics in the red beetroot water extracts was determined according to a modification of the Folin-Ciocalteu method and expressed as gallic acid equivalents (GAE). The compounds of interest were identified by HPLC-ESI-MS and NMR techniques, and the contents of compounds were determined by HLPC analyses. The total phenolic contents in various root parts were found to decrease in the order peel, crown, flesh. Significant differences in the contents of total phenolics and individual compounds were found when the effect of cold storage (5 degrees C, 0-196 days) on the constituents of the peel from intact roots was examined. In addition to the betacyanins of red beetroot peel found in our earlier study, tentative identifications of betanidin and feruloylamaranthin were made.

Chenopodiaceae↗
PubMed1979

Ionic Regulation for Cytokinin-dependent Betacyanin Synthesis in Amaranthus Seedlings.

Potassium ions at low concentrations stimulate cytokinin-dependent betacyanin synthesis in Amaranthus tricolor seedlings more than other alkali metal ions when tested as the chloride salts. The sequence of relative stimulation is K(+) > Rb(+) > (Na(+) = Li(+)). Calcium and Mg(2+) ions are inhibitory at concentrations > 1 millimolar when tested as chlorides. Anions also have an effect on the degree of alkali metal stimulation in the order PO(4) (3-) > NO(3) (-) > Cl(-). The high activity of phosphate may be partly due to its chelating effect on inhibitory Ca(2+) ions, or to effects on K(+) uptake. A mixture of Na(+) and K(+) in the presence of phosphate is more effective than either cation alone. This result may be due either to effects on tyrosine transport or on the potassium uptake system. Phytochrome-dependent betacyanin synthesis shows the same stimulation by Na(+) plus K(+). The effect of a number of inhibitors of transport systems on betacyanin accumulation is reported. The possible role of the ionic environment of cells in their metabolic regulation is discussed, particularly in relation to cytokinin action.

Journal Article↗