Betalains: properties, sources, applications, and stability ? a review.

Summary Consumers are increasingly avoiding foods containing synthetic colourants, which lead food industries to replace them by natural pigments, such as carotenoids, betalains, anthocyanins and carminic acid. Betalains are water-soluble nitrogen-containing pigments, composed of two structural groups: the red-violet betacyanins and the yellow-orange betaxanthins. This review synthesises the published literature on basic chemistry of betalains, their sources and chemical stability. Moreover, several works are mentioned which have demonstrated the potent antioxidant activity of betalains, which has been associated with protection against degenerative diseases.

[1]  L. Zubik,et al.  Phenol antioxidant quantity and quality in foods : Vegetables , 1998 .

[2]  R. Carle,et al.  Renal excretion of antioxidative constituents from red beet in humans , 2005 .

[3]  R. Carle,et al.  Cactus fruits. More than colour , 2006 .

[4]  V. Shenoy.  Anthocyanins - prospective food colours , 1993 .

[5]  R. Carle,et al.  Betacyanins in fruits from red-purple pitaya, Hylocereus polyrhizus (Weber) Britton & Rose , 2002 .

[6]  P. C. Mezquita,et al.  Caracterización del colorante de remolacha roja (Beta vulgaris L.) en polvo , 1996 .

[7]  J. H. Elbe,et al.  Kinetics of the Degradation and Regeneration of Betanine , 1985 .

[8]  J. Singer,et al.  DEGRADATION RATES OF VULGAXANTHINE I , 1980 .

[9]  D. Strack,et al.  Recent advances in betalain research. , 2003, Phytochemistry.

[10]  T. Nilsson.  Beta vulgaris L. ssp. vulgaris var. rubra L. , 1970 .

[11]  Agata Czyżowska,et al.  The influence of lactic acid fermentation process of red beet juice on the stability of biologically active colorants , 2006 .

[12]  V. Wray,et al.  Humilixanthin a new betaxanthin from Rivina humilis , 1987 .

[13]  H. Corke,et al.  Colorant properties and stability of Amaranthus Betacyanin pigments , 1998 .

[14]  D. Andrenyak,et al.  Determination of nalmefene by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. , 2005, Journal of analytical toxicology.

[15]  H. Gottlieb,et al.  Betacyanins from vine cactus Hylocereus polyrhizus. , 2001, Phytochemistry.

[16]  K. Pihlaja,et al.  Betalains and Phenolics in Red Beetroot (Beta vulgaris) Peel Extracts: Extraction and Characterisation , 2001, Zeitschrift fur Naturforschung. C, Journal of biosciences.

[17]  V. Wray,et al.  Neobetanin: isolation and identification from Beta vulgaris , 1985 .

[18]  Mei Sun,et al.  Antioxidant activity of betalains from plants of the amaranthaceae. , 2003, Journal of agricultural and food chemistry.

[19]  Hans-Eberhard Hilpert,et al.  Totalsynthese von Decarboxybetalainen durch photochemische Ringöffnung von 3‐(4‐Pyridyl)alanin , 1985 .

[20]  Florian C. Stintzing,et al.  Functional properties of anthocyanins and betalains in plants, food, and in human nutrition , 2004 .

[21]  R. Carle,et al.  Identification of betalains from yellow beet (Beta vulgaris L.) and cactus pear [Opuntia ficus-indica (L.) Mill.] by high-performance liquid chromatography-electrospray ionization mass spectrometry. , 2002, Journal of agricultural and food chemistry.

[22]  R. Leathers,et al.  Betalain producing cell cultures ofBeta vulgaris L. var. bikores monogerm (red beet) , 1992, In Vitro – Plant.

[23]  J. H. Elbe,et al.  Stability Comparison of Two Betacyanine Pigments — Amaranthine and Betanine , 1986 .

[24]  J. Fernández-López,et al.  Color properties and stability of betacyanins from Opuntia fruits. , 2003, Journal of agricultural and food chemistry.

[25]  R. C. Wiley,et al.  Betacyanine and Betaxanthine Decolorizing Enzymes in the Beet (Beta vulgaris L.) Root , 1982 .

[26]  J. Fernández-López,et al.  The isolation and properties of a concentrated red-purple betacyanin food colourant from Opuntia stricta fruits , 2006 .

[27]  L. Andersen,et al.  A systematic screening of total antioxidants in dietary plants. , 2002, The Journal of nutrition.

[28]  J. Zrÿd,et al.  Two betalains from Portulaca grandiflora , 1991 .

[29]  N. Rastogi,et al.  Enhanced mass transfer during solid–liquid extraction of gamma-irradiated red beetroot , 2006 .

[30]  R. Reynoso,et al.  Stability of Betalain Pigments from a Cactacea Fruit , 1997 .

[31]  R. C. Wiley,et al.  RECOVERY OF BETALAINES FROM RED BEETS BY A DIFFUSION‐EXTRACTION PROCEDURE , 1978 .

[32]  H. Corke,et al.  Amaranthus Betacyanin Pigments Applied in Model Food Systems , 1999 .

[33]  T. Mabry,et al.  The conversion of betanidin and betanin to neobetanindin derivatives , 1967 .

[34]  S. Wybraniec,et al.  1H and 13C NMR spectroscopic structural elucidation of new decarboxylated betacyanins , 2006 .

[35]  R. Muñoz,et al.  Characterization of betacyanin oxidation catalyzed by a peroxidase from Beta vulgaris L. roots. , 2001, Journal of agricultural and food chemistry.

[36]  Dejian Huang,et al.  Analysis of antioxidant activities of common vegetables employing oxygen radical absorbance capacity (ORAC) and ferric reducing antioxidant power (FRAP) assays: a comparative study. , 2002, Journal of agricultural and food chemistry.

[37]  H. Corke,et al.  Characterization and application of betalain pigments from plants of the Amaranthaceae , 2005 .

[38]  Mario Piattelll.  19 – The Betalains: Structure, Biosynthesis, and Chemical Taxonomy , 1981 .

[39]  H. Daood,et al.  Comparison of red beet (Beta vulgaris var conditiva) varieties on the basis of their pigment components , 2001 .

[40]  C. Zou,et al.  Cactus pear: a natural product in cancer chemoprevention , 2005, Nutrition journal.

[41]  F. Barrera,et al.  Estabilidad de las betalaínas extraídas del garambullo (Myrtillocactus geometrizans) / Stability of betalains extracted from garambullo (Myrtillocactus geometrizans) , 1998 .

[42]  G. Gutiérrez-López,et al.  Production of food related colorants by culture of plant cells. The case of betalains. , 1999, Advances in experimental medicine and biology.

[43]  G. M. Sapers,et al.  VARIETAL DIFFERENCES IN COLORANT PROPERTIES AND STABILITY OF RED BEET PIGMENTS , 1979 .

[44]  S. Šilhár,et al.  Conversion of betalains in the presence of antioxidants , 2000 .

[45]  J. Czapski.  Heat stability of betacyanins in red beet juice and in betanin solutions , 1990 .

[46]  Chang Yong Lee,et al.  BLANCHING EFFECT ON POLYPHENOL OXIDASE ACTIVITY IN TABLE BEETS , 1979 .

[47]  C. Gentile,et al.  Increased Resistance to Oxidation of Betalain-enriched Human Low Density Lipoproteins , 2003, Free radical research.

[48]  R. Carle,et al.  Colour studies on fruit juice blends from Opuntia and Hylocereus cacti and betalain-containing model solutions derived therefrom , 2005 .

[49]  M. Özilgen,et al.  Modeling of Sequential Batch Ultrafiltration of Red Beet Extract , 1988 .

[50]  R. Carle,et al.  Structural and chromatic stability of purple pitaya (Hylocereus polyrhizus [Weber] Britton & Rose) betacyanins as affected by the juice matrix and selected additives , 2006 .

[51]  C. Gentile,et al.  Antioxidant Betalains from Cactus Pear (Opuntia ficus‐indica) Inhibit Endothelial ICAM‐1 Expression , 2004, Annals of the New York Academy of Sciences.

[52]  J. H. Elbe,et al.  Oxygen Involvement in Betanine Degradation: Effect of Antioxidants , 2006 .

[53]  O. Paredes-López,et al.  Natural Pigments: Carotenoids, Anthocyanins, and Betalains — Characteristics, Biosynthesis, Processing, and Stability , 2000, Critical reviews in food science and nutrition.

[54]  R. Carle,et al.  Identification of betalains from petioles of differently colored Swiss chard (Beta vulgaris L. ssp. cicla [L.] Alef. Cv. Bright Lights) by high-performance liquid chromatography-electrospray ionization mass spectrometry. , 2004, Journal of agricultural and food chemistry.

[55]  R. Nicolaus,et al.  Pigments of centrospermae—V. : Betaxanthins from Mirabilis jalapa L. , 1965 .

[56]  M. Drdák,et al.  Kinetics of the thermal degradation of betanine , 1990 .

[57]  Bradley W. Bolling,et al.  Betalains, Phase II Enzyme-Inducing Components From Red Beetroot (Beta vulgaris L.) Extracts , 2005, Nutrition and cancer.

[58]  B. P. Wasserman,et al.  Effect of Hydrogen Peroxide and Phenolic Compounds on Horseradish Peroxidase-Catalyzed Decolorization of Betalain Pigments , 1984 .

[59]  R. Carle,et al.  Thermal degradation of betacyanins in juices from purple pitaya [Hylocereus polyrhizus (Weber) Britton & Rose] monitored by high-performance liquid chromatography–tandem mass spectometric analyses , 2004 .

[60]  Alison Downham,et al.  Colouring our foods in the last and next millennium , 2000 .

[61]  R. Carle,et al.  Impact of Thermal Treatment on Color and Pigment Pattern of Red Beet (Beta vulgaris L.) Preparations , 2006 .

[62]  Dietrich Knorr,et al.  Accelerated Mass Transfer During Osmotic Dehydration of High Intensity Electrical Field Pulse Pretreated Carrots , 1999 .

[63]  P. Nobel,et al.  Cacti as Crops , 2010 .

[64]  J. H. Elbe,et al.  Oxygen involvement in betanine degradation - Measurement of active oxygen species and oxidation reduction potentials , 1985 .

[65]  R. Carle,et al.  First 13C-NMR Assignments of Betaxanthins , 2006 .

[66]  T. Kuusi,et al.  The stability properties of golden beet and red beet pigments: Influence of pH, temperature, and some stabilizers , 1978, Zeitschrift fur Lebensmittel-Untersuchung und -Forschung.

[67]  Yu Lin,et al.  Antioxidant and antiproliferative activities of red pitaya , 2006 .

[68]  D. Strack,et al.  Intramolecular stabilization of acylated betacyanins , 1998 .

[69]  C. Biliaderis,et al.  Degradation kinetics of beetroot pigment encapsulated in polymeric matrices , 2001 .

[70]  D. Pszczola.  Natural colors: pigments of imagination , 1998 .

[71]  P. Simon,et al.  Stability of red beet pigment concentrate in maize starch , 1992 .

[72]  J. Kanner,et al.  Betalains--a new class of dietary cationized antioxidants. , 2001, Journal of agricultural and food chemistry.

[73]  J. H. Elbe,et al.  Betalaines as Colorants in Dairy Products1 , 1975 .

[74]  J. H. Elbe,et al.  Oxygen involvement in betanin degradation , 1984 .

[75]  T. Akita,et al.  Production of Betacyanins by a Cell Suspension Culture of Table Beet (Beta vulgaris L.) , 2000, Bioscience, biotechnology, and biochemistry.

[76]  V. Wray,et al.  Betacyanins from bracts of Bougainvillea glabra. , 1994, Phytochemistry.

[77]  I. Saguy.  THERMOSTABILITY OF RED BEET PIGMENTS (BETANINE AND VULGAXANTHIN–I): INFLUENCE OF pH AND TEMPERATURE , 1979 .

[78]  A. Dreiding,et al.  Deuterierung von Betanidin und Indicaxanthin, (E/Z)‐Stereoisomerie in Betalainen , 1984 .

[79]  S. Wybraniec,et al.  Generation of decarboxylated and dehydrogenated betacyanins in thermally treated purified fruit extract from purple pitaya (Hylocereus polyrhizus) monitored by LC-MS/MS. , 2005, Journal of agricultural and food chemistry.

[80]  R. Carle,et al.  Stability and color changes of thermally treated betanin, phyllocactin, and hylocerenin solutions. , 2006, Journal of agricultural and food chemistry.

[81]  Kobayashi,et al.  The decisive step in betaxanthin biosynthesis is a spontaneous reaction1 , 1999, Plant physiology.

[82]  R. Carle,et al.  Phytochemical and nutritional significance of cactus pear , 2001 .

[83]  K. Mı́ková,et al.  Heat stability of betacyanins , 1983 .

[84]  A. Bilyk,et al.  Reversibility of thermal degradation of betacyanins under the influence of isoascorbic acid , 1982 .

[85]  A. Tsuruta,et al.  Chemoprevention of DMBA-induced UV-B promoted, NOR-1-induced TPA promoted skin carcinogenesis, and DEN-induced phenobarbital promoted liver tumors in mice by extract of beetroot. , 2003, Pharmacological research.

[86]  Luisa Tesoriere,et al.  Supplementation with cactus pear (Opuntia ficus-indica) fruit decreases oxidative stress in healthy humans: a comparative study with vitamin C. , 2004, The American journal of clinical nutrition.

[87]  J. Karovičová,et al.  Red beet pigment composition. Effects of fermentation by different strains of Saccharomyces cerevisiae , 1992 .

[88]  I. Saguy,et al.  Effect of Oxygen Retained on Beet Powder on the Stability of Betanine and Vulgaxanthine I , 1984 .

[89]  S. Mizrahi,et al.  Thermal kinetic degradation of betanin and betalamic acid , 1978 .

[90]  R. C. Wiley,et al.  Betalaine Yield from a Continuous Solid‐Liquid Extraction System as Influenced by Raw Product, Post‐Harvest and Processing Variables , 1981 .

[91]  M. Piattelli,et al.  Pigments of Centrospermae—III. , 1965 .

[92]  M. Fincan,et al.  Pulsed electric field treatment for solid-liquid extraction of red beetroot pigment: mathematical modelling of mass transfer , 2004 .

[93]  H. Pourrat,et al.  Betalains Assay of Fermented Red Beet Root Extract by High Performance Liquid Chromatography , 1988 .

[94]  R. Carle,et al.  Structural investigations on betacyanin pigments by LC NMR and 2D NMR spectroscopy. , 2004, Phytochemistry.

[95]  J. Fellman,et al.  Biosynthetic origin of geosmin in red beets (Beta vulgaris L.). , 2003, Journal of agricultural and food chemistry.

[96]  J. H. Elbe,et al.  Effect of pH on the Degradation and Regeneration of Betanine , 1987 .

[97]  C. H. Amundson,et al.  COLOR STABILITY OF BETANIN , 1974 .

[98]  F. García-Carmona,et al.  Characterization of the antiradical activity of betalains from Beta vulgaris L. roots , 1998 .

[99]  M. Dornier,et al.  Colorant and antioxidant properties of red-purple pitahaya (Hylocereus sp.) , 2005 .

[100]  L. Tesoriere,et al.  Distribution of betalain pigments in red blood cells after consumption of cactus pear fruits and increased resistance of the cells to ex vivo induced oxidative hemolysis in humans. , 2005, Journal of agricultural and food chemistry.

[101]  J. L. Smith,et al.  Anthocyanins and betalains , 1996 .

[102]  L. Tesoriere,et al.  Absorption, excretion, and distribution of dietary antioxidant betalains in LDLs: potential health effects of betalains in humans. , 2004, The American journal of clinical nutrition.

[103]  R. C. Wiley,et al.  Purification and Concentration of Betalaines by Ultrafiltration and Reverse Osmosis , 1982 .

[104]  Sang-hee Kim,et al.  Repeated Regeneration of Degraded Red Beet Juice Pigments in the Presence of Antioxidants , 1998 .

[105]  V. Georgiev,et al.  Biosynthesis and Radical Scavenging Activity of Betalains during the Cultivation of Red Beet (Beta vulgaris) Hairy Root Cultures , 2002, Zeitschrift fur Naturforschung. C, Journal of biosciences.

[106]  R. Carle,et al.  Color, betalain pattern, and antioxidant properties of cactus pear (Opuntia spp.) clones. , 2005, Journal of agricultural and food chemistry.

[107]  C. Obinger,et al.  Mechanism of interaction of betanin and indicaxanthin with human myeloperoxidase and hypochlorous acid. , 2005, Biochemical and biophysical research communications.

[108]  M. Pedreño,et al.  Subcellular localization and isoenzyme pattern of peroxidase and polyphenol oxidase in beet root (Beta vulgaris L.). , 2002, Journal of agricultural and food chemistry.

[109]  J. H. Elbe,et al.  Degradation kinetics of betanin in solutions as influenced by oxygen , 1982 .

[110]  R. Nicolaus,et al.  Pigments of centrospermae—IV : On the biogenesis of indicaxanthin and betanin in Opuntia ficus-indica Mill. , 1965 .

[111]  S. Schwartz,et al.  Identification of betanin degradation products , 1983, Zeitschrift fur Lebensmittel-Untersuchung und -Forschung.

[112]  F. Stintzing,et al.  Nutritional and medicinal use of Cactus pear (Opuntia spp.) cladodes and fruits. , 2006, Frontiers in bioscience : a journal and virtual library.

[113]  J. H. Elbe,et al.  Photochemial Degradation of Betanine and Selected Anthocyanins , 1981 .

[114]  I. Saguy,et al.  Effect of Water Activity and Moisture Content on the Stability of Beet Powder Pigments , 1983 .

[115]  Bradley W. Bolling,et al.  Phase II enzyme-inducing and antioxidant activities of beetroot (Beta vulgaris L.) extracts from phenotypes of different pigmentation. , 2002, Journal of agricultural and food chemistry.

[116]  H. Nishino,et al.  Chemoprevention of lung and skin cancer by Beta vulgaris (beet) root extract. , 1996, Cancer letters.

[117]  Florian C. Stintzing,et al.  Betalain stability and degradation--structural and chromatic aspects , 2006 .

[118]  K. Taiwo,et al.  Use of pulsed electric field pre-treatment to improve dehydration characteristics of plant based foods , 2001 .

[119]  M. Piattelli,et al.  Isolation, structure and absolute configuration of indicaxanthin , 1964 .

[120]  M. Pedreño,et al.  Correlation between antiradical activity and stability of betanine from Beta vulgaris L roots under different pH, temperature and light conditions , 2001 .

[121]  R. Altamirano.  Thermal degradation of betanine in various water alcohol model systems , 1993 .

[122]  I. Goldman,et al.  Pigment Distribution and Total Dissolved Solids of Selected Cycles of Table Beet from a Recurrent Selection Program for Increased Pigment , 2005 .

[123]  S. Wybraniec.  Formation of decarboxylated betacyanins in heated purified betacyanin fractions from red beet root (Beta vulgaris L.) monitored by LC-MS/MS. , 2005, Journal of agricultural and food chemistry.

[124]  L. Tesoriere,et al.  Antioxidant activities of sicilian prickly pear (Opuntia ficus indica) fruit extracts and reducing properties of its betalains: betanin and indicaxanthin. , 2002, Journal of agricultural and food chemistry.

[125]  D. Knorr,et al.  Challenges and opportunities for metabolite production from plant cell and tissue cultures , 1997 .

[126]  H. A. Stafford.  Anthocyanins and betalains: evolution of the mutually exclusive pathways , 1994 .

[127]  M. Kearsley,et al.  Stability and use of natural colours in foods Red beet powder, copper chlorophyll powder and cochineal , 2007 .

[128]  H. Corke,et al.  Production and Properties of Spray‐dried Amaranthus Betacyanin Pigments , 2000 .

[129]  M. Fincan,et al.  Pulsed electric field treatment for solid-liquid extraction of red beetroot pigment , 2004 .

[130]  R. Carle,et al.  Evaluation of colour properties and chemical quality parameters of cactus juices , 2003 .

[131]  R. Carle,et al.  Identification of heat-induced degradation products from purified betanin, phyllocactin and hylocerenin by high-performance liquid chromatography/electrospray ionization mass spectrometry. , 2005, Rapid communications in mass spectrometry : RCM.

[132]  J. H. Elbe,et al.  Betanine stability in buffered solutions containing organic acids, metal cations, antioxidants, or sequestrants , 1979 .