Abstract
The betalains, which include the red-violet betacyanins and the yellow betaxanthins (Fig. 10.1), represent a structurally and biosynthetically distinct class of naturally-occurring pigments. These pigments are found in flowering plants only in members of certain families of the order Caryophyllales (Centrospermae) (Table 10.1), though betaxanthins have also been shown to occur in the fly agaric, Amanita muscaria (Dopp et al. 1982). Both betacyanins and betaxanthins possess a dihydropyridine moiety which is attached via a vinyl group to another nitrogenous group. In the betacyanins the latter is a glyeosyl-hydroxylated dihydroindole ring; in the betaxanthins it is any one of several amino acids or amines. The basic chromophore of the betalain pigments is the 1,7-diazaheptamethinium system, as discussed by Mabry et al. (1967) and Mabry and Dreiding (1968). The different spectral properties of the betacyanins and betaxanthins are due to the extension of this conjugated system through the dihydroindole moiety in the betacyanins. The term “betalains” was introduced by Mabry and Dreiding (1968) to emphasize the common biogenetic and structural features of these two groups, which clearly distinguish this class of pigments from the more common group of plant pigments, the anthocyanins.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Bate-Smith EC (1962) The phenolic constituents of plants and their taxonomic significance. J Linn Soc Bot 58:95–173
Beck E, Merxmüller H, Wagner H (1962) Über die Art der Anthocyane bei Plum-baginaceen, Alsinoideen, und Molluginaceen. Planta 58:220–224
Behnke H-D, Mabry TJ (1977) S-type sieve-element plastids and anthocyanins in Vivianiaceae: Evidence against its inclusion into Centrospermae. Plant Syst Evol 126:371–375
Behnke H-D, Chang C, Eifert IJ, Mabry TJ (1974) Betalains and P-type sieve-tube plastids in Petiveria and Agdestis (Phytolaccaceae). Taxon 23:541–542
Behnke H-D, Mabry TJ, Eifert IJ, Pop L (1975) P-type sieve-element plastids and betalains in Portulacaceae (including Ceraria, Portulacaria, and Talinella). Can J Bot 53:2103–2109
Behnke H-D, Mabry TJ, Neumann P, Barthlott W (1983) Ultrastructural, micromorphological and phytochemical evidence for a “central position” of Macarthuria (Molluginaceae) within the Caryophyllales. Plant Syst Evol 143:151–161
Bischoff H (1876) Das Caryophyllinenroth. Inaugural Dissertation. Universität Tübingen
Bittrich B, Amaral MCE (1991) Proanthocyanidins in the testa of centrospermous seeds. Biochem Syst Ecol 19:319–321
Bogle AL, Swain T, Thomas RD, Kohn ED (1971) Geocarpon: Aizoaceae or Caryo-phyllaceae? Taxon 20:473–477
Böhm H, Rink E (1988) Betalains. In: Constabel F, Vasil IK (eds) Cell culture and somatic cell genetics of plants, vol 5. Academic Press, New York, pp 449–463
Böhm H, Böhm L, Rink E (1991) Establishment and characterization of a betaxanthin-producing cell culture from Portulaca grandiflora. Plant Cell Tissue Organ Cult 26:75–82
Bokern M, Wray V, Strack D (1991) Accumulation of phenolic acid conjugates and betacyanins, and changes in the activities of enzymes involved in feruloylglucose metabolism in cell-suspension cultures of Chenopodium rubrum L. Planta 184: 261–270
Bokern M, Heuer S, Strack D (1992) Hydroxycinnamic acid transferases in the biosynthesis of acylated betacyanins: Purification and characterization from cell cultures of Chenopodium rubrum and occurrence in some other members of the Caryophyllales. Bot Acta 105:146–151
Bonness MS, Mabry TJ (1992) Tissue culture of endod (Phytolacca dodecandra L’Herit): Growth and production of ribosome-inaetivating proteins. Plant Cell Rep 11:66–70
Burret F, Rabesa Z, Zandonella P, Viorin B (1981) Contribution biochimique à la systématique de l’ordre des Centrospermales. Biochem Syst Ecol 9:257–262
Burret F, Lebreton Ph, Voirin B (1982) Les aglycones flavoniques des cactées: Distribution, signification. J Nat Prod 45:687–693
Döpp H, Maurer S, Sasaki AN, Musso H (1982) Die Konstitution der Musca-aurine. Liebigs Ann Chem 1982:254–264
Dreiding AS (1961) The betacyanins, a class of red pigments in the Centrospermae. In: Ollis WE (ed) Recent developments in the chemistry of natural phenolic compounds. Pergamon Press. New York, pp 194–211
Durand R, Zenk MH (1974) Enzymes of the homogentisate ring-cleavage pathway in cell suspension cultures of higher plants. FEBS Lett 39:218–220
Elliot DC, Schultz CG, Cassar RA (1983) Betacyanin decolourizing enzyme in Amaranthus tricolor seedlings. Phytochemistry 22:383–387
Ellis BE (1973) Catabolic ring-cleavage of tyrosine in plant cell cultures. Planta 111: 113–118
Ehrendorfer (1976) Closing remarks: Systematics and evolution of centrospermous families. Plant Syst Evol 126:99–106
Fischer N, Dreiding AS (1972) Biosynthesis of betalaines. On the cleavage of the aromatic ring during the enzymatic transformation of dopa into betalamic acid. Helv Chim Acta 55:649–658
Forsyth WGC, Simmonds NW (1954) A survey of the anthocyanins of some tropical plants. Proc R Soc Lond Ser B 142:549–564
Gertz O (1906) Studier övfer Anthocyan. Dissertation, Lund
Giannasi DE (1988) Flavonoids and evolution in the dicotyledons. In: Harborne JB (ed) The flavonoids: Advances in research since 1980. Chapman and Hall, London, pp 479–504
Girod PA, Zryd JP (1991a) Biogenesis of betalains: Purification and partial characterization of dopa 4,5-dioxygenase from Amanita muscaria Phytochemistry 30: 169–174
Girod PA, Zryd JP (1991b) Secondary metabolism in cultured red beet (Beta vulgaris L.) cells: Differential regulation of betaxanthin and betacyanin biosynthesis. Plant Cell Tissue Organ Cult 25:1–12
Harris PJ, Hartley RD (1980) Phenolic constituents of the cell walls of monocotyledons. Biochem Syst Ecol 8:153–160
Hartley RD, Harris PJ (1981) Phenolic constitutents of the cell walls of dicotyledons. Biochem Syst Ecol 9:189–203
Hattori S, Komamine A (1959) Stizolobic acid: A new amino-acid in Stizolobium hassjoo Nature 183:1116–1117
Heuer S, Strack D (1992) Synthesis of betanin from betanidin and UDP-glucose by a protein preparation from cell suspension cultures of Dorotheanthus bellidiformis(Burm. f.) N.E.Br. Planta 186:626–628
Hinz U, Richard C, Bindschedler L, Zryd JP (1992) Betalain synthesis in A. muscaria Abstract. Experientia 48:A10
Hörhammer L, Wagner H, Gritzsche W (1964) Zur Biosynthese der Betacyane I. Biochem Z 339:398–400
Hunziker JH, Behnke HD, Eifert IJ, Mabry TJ (1974) Halophytum ameghinoi: a betalain-containing and P-type sieve-tube plastid species. Taxon 23:537–539
Impellizzeri G, Piatelli M (1972) Biosynthesis of betalains: Formation of indicaxanthin inOpuntia ficus-indica fruits. Phytochemistry 11:2499–2502
Impellizzeri G, Piattelli M, Sciuto S (1973) A new betaxanthin fromGlottiphyllumlongum Phytochemistry 12:2293–2294
Keller W (1936) Inheritance of some major color types in beets. J Agric Res 52:27–38
Kimler L, Mears J, Mabry TJ, Rosier H (1970) On the question of the mutual exclusive-ness of betalains and anthocyanins. Taxon 19:875–878
Kishima Y, Suiko M, Adachi T (1991) Betalain pigmentation in petals of Portulaca is preceded by a dramatic tyrosine accumulation. J Plant Physiol 137:505–506
Kuli J, Kühn B (1978) Vieraea 8:187 cited in: Hegnauer R Chemotaxonomie der Pflanzen, vol VIII. Birkhäuser, Basel, pp 28–32
Kryz F (1926) Ein Beitrag zur Kenntnis des Vorkommens und der Reaktionen der Anthocyanfarbstoffe der Rübenrotgruppe. Oester Chem Ztg 23:55–56
Lawrence WJC, Price JR, Robinson GM, Robinson R (1939) The distribution of anthocyanins in flowers, fruits and leaves. Philos Trans R Soc Lond Ser B 1939–1941(230): 149–178
Mabry TJ (1964) The betacyanins, a new class of red violet pigments, and their phylogenetic significance. In: Leone CA (ed) Taxonomic biochemistry and serology. Roland Press, New York, pp 239–253
Mabry TJ (1966) The betacyanins and betaxanthins. In: Swain T (ed) Comparative phytochemistry. Academic Press, London, pp 231–244
Mabry TJ (1973) Is the order Centrospermae monophyletic? In: Bendz G, Santesson J (eds) Chemistry in botanical classification. Nobel Foundation, Stockholm and Academic Press, London, pp 275–285
Mabry TJ, Behnke H-D (1976) Betalains and P-type sieve-element plastids: The systematic position of Dysphania R. Br. (Centrospermae). Taxon 25:109–111
Mabry TJ, Dreiding AS (1968) The betalains. In: Mabry TJ, Alston RE, Runeckles VC (eds) Recent advances in phytochemistry, vol 1. Appleton-Century-Crofts, New York, pp 145–160
Mabry TJ, Wyler H, Sassu G, Mercier M, Parikh I, Dreiding AS (1962) Die Struktur des Neobetanidins: Über die Konstitution des Randenfarbstoffes Betanin. Helv Chim Acta 45:640–647
Mabry TJ, Taylor A, Turner BL (1963) The betacyanins and their distribution. Phytochemistry 2:61–64
Mabry TJ, Wyler H, Parikh I, Dreiding AS (1967) The conversion of betanidin and betanin to neobetanidin derivatives. Tetrahedron 23:3111–3127
Mabry TJ, Eifert IJ, Chang C, Mabry H, Kidd C, Behnke H-D (1975) Theligonaceae: Pigment and ultrastructural evidence with excludes it from the order Centrospermae. Biochem Syst 3:53–55
Mabry TJ, Behnke H-D, Eifert IJ (1976) Betalains and P-type sieve-element plastids in Gisekia L. (Centrospermae). Taxon 25:112–114
Mabry TJ, Neuman P, Philipson WR (1978) Hectorella:a member of the betalain-suborder Chenopodiineae of the order Centrospermae. Plant Syst Evol 130:163–165
Martin C, Prescott A, Mackay S, Bartlett J, Vrijlandy E (1991) Control of anthocyanin biosynthesis in flowers of Antirrhinum majus Plant J 1:37–49
Mazelis M (1980) Amino acid catabolism. In: Stumpf PK, Conn EE (eds) The biochemistry of plants. Vol 5. Amino acids and derivatives. Academic Press, New York, pp 542–567
Mears JA (1976) Guide to research in plant taxonomy. Chem Plant Taxon Newslett 25:11–14
Menssen A, Höhmann S, Martin W, Schnäble PS, Peterson PA, Saedler H, Gierl A (1990) The En/Spm transposable element of Zea mays contains splice sites at the termini generating a novel intron from a dSpm element in the A2 gene. EMBO J 9:3051–3057
Miller HE, Rosier H, Wohlpart A, Wyler H, Wilcox ME, Frohofer H, Mabry TJ, Dreiding AS (1968) Biogenese der Betalaine: Biotransformation von Dopa und Tyrosin in den Betalaminsäureteil des Betanins. Helv Chim Acta 51:1470–1474
Minale L, Piattelli M, Nicolaus RA (1965) Pigments of Centrospermae. IV. On the biogenesis of indicaxanthin and betanin in Opuntia flcus-indica Mill. Phytochemistry 4:593–597
Nyananyo (1986) A survey of leaf flavonoids in the Portulacaceae. Biochem Syst Ecol 14:633–635
Paré PW, Dmitrieva N, Mabry TJ (1991) Phytoalexin aurone induced inCephalocereussenilis liquid suspension culture. Phytochemistry 30:1133–1135
Paré PW, Mischke CF, Edwards R, Dixon RA, Norman HA, Mabry TJ (1992) Induction of phenylpropanoid pathway enzymes in elicitor-treated cultures of Cephalocereus senilis Phytochemistry 31:149–153
Piattelli M, Impellizzeri (1970) 2-Descarboxybetanidin, a minor betacyanin from Car-pobrotus acinaciformis. Phytochemistry 9:2553–2556
Piattelli M, Imperato F (1969) Betacyanins of the family Cactaceae. Phytochemistry 8:1503–1507
Piattelli M, Imperato F (1971) Betacyanins of some Chenopodiaceae. Phytochemistry 10:3133–3134
Piattelli M, Minale L (1964a) Pigments of Centrospermae. I. Betacyanins fromPhyl-locactus hybridus Hort, and Opuntia ficus-indica Mill. Phytochemistry 3:307–311
Piattelli M, Minale L (1964b) Pigments of Centrospermae. II. Distribution of betacyanins. Phytochemistry 3:547–557
Piattelli M, Minale L, Prota G (1964) Isolation, structure and absolute configuration of indicaxanthin. Tetrahedron 22:2325–2329
Rabesa ZA (1982) Weitere Untersuchungen an Didiereaceen. Teil 5. Recherche chimio-systématiques sur les flavonoides des Didiéréacées. Tropische und subtropische Pflanzenwelt 37:1–26
Steiner, Mainz Rauh W, Reznik H (1961) Zur Frage der systematischen Stellung der Didiereaceen. Bot Jahrb 81:94–105
Reznik H (1955) Die Pigmente der Centrospermen als systematisches Element. Z Bot 43:499–530
Reznik H (1957) Die Pigmente der Centrospermen als systematisches Element. II. Untersuchungen über das ionophoretische Verhalten. Planta 49:406–434
Reznik H (1978) Das Vorkommen von Betalaminsäure bei Centrospermen. Z Pflanzenphysiol 87:95–102
Reznik H, Engel U, Wambach C (1988) Untersuchungen über die Betalainfarbstoffe der Aizoaceae. I. Die Betaxanthine der Ruschieae. Beitr Biol Pflanz 63:209
Richardson M (1978) Flavonols and C-glycosylflavonoids of the Caryophyllales. Biochem Syst Ecol 6:283–286
Richardson PM (1981) Flavonoids of some controversial members of the Caryophyllales (Centrospermae). Plant Syst Evol 138:227–233
Rink E, Böhm H (1985) Changed betaxanthin pattern in violet flowers ofPortulacagrandiflora after the feeding of dopa. Phytochemistry 24:1475–1477
Robinson AM, Robinson R (1932) Synthetical experiments on the nature of betanin and related nitrogenous anthocyanins. J Chem Soc 1932:1439–1445
Saito K, Komamine A (1975) Biosynthesis of stizolobinic acid and stizolobic acid in the etiolated seedlings of Stizolobium hassjoo Z Naturforsch 30c:659–662
Saito K, Komamine A (1978) Biosynthesis of stizolobinic acid and stizolobic acid in higher plants. Eur J Biochem 82:385–392
Salt TA, Xu S, Patterson GW, Adler JH (1991) Diversity of sterol biosynthetic capacity in the Caryophyllidae. Lipids 26:604–613
Sanderson SC, Ge-Ling C, McArthur ED, Stutz HC (1988) Evolutionary loss of flavonoids and other chemical characters in the Chenopodiaceae. Biochem Syst Ecol 16:143–149
Schmidt OT, Schönleben W (1957) Zur Kenntnis der Farbstoffe der Roten Rübe, II. Z Naturforsch 12b:262–263
Schmidt OT, Becher P, Hubner M (1960) Zur Kenntnis der Farbstoffe der Roten Rübe, III. Chem Ber 93:1296–1304
Schudel G (1918) Über die Anthocyane vonBeta vulgaris L. (var. rapacea Koch, forma rubra L.) und Raphanus sativus L. (var. radícula Pers.). Promotionsarbeit, ETH, Zürich
Sciuto S, Oriente G, Piattelli M (1972) Betanidin glucosylation in Opuntia dillenii Phytochemistry 11:2259–2262
Sciuto S, Oriente GP, Piatteli M, Impellizzeri G, Amico V (1974) Biosynthesis of amaranthin in Celosía plumosa Phytochemistry 13:947–951
Seeligman P, Kraponikas A (1969) Report of current chemosystematic studies at the Department of Botany, Instituto Migvel Lillo, Universidad Nacional de Tucumán S.M. de Tucumán, Argentina. Chem Plant Taxon Newslett 13:8–11
Stafford HA (1989) The enzymology of proanthocyanidin biosynthesis. In: Hemingway RW, Karchesy JJ (eds) The chemistry and significance of condensed tannins. Plenum Press, New York, pp 47–70
Steglich W, Strack D (1990) Betalains. In: Brossi A (ed) The alkaloids, vol 39. Academic Press, New York, pp 1–62
Strack D, Heilemann J, Mömken M, Wray V (1988) Cell wall-conjugated phenolics from Coniferae leaves. Phytochemistry 27:3517–3521
Strack D, Marxen N, Reznik H, Ihlenfeld HD (1990) Distribution of betacyanins and hydroxycinnamic acid-glucose esters in flowers of the Ruschieae. Phytochemistry 29:2175–2178
Taylor TWJ (1940) Plant pigments in the Galápagos Islands. Proc R Soc Lond Ser B 129:230–237
Terradas F, Wyler H (1991a) 2,3- and 4,5-secodopa, the biosynthetic intermediates generated from l-DOPA by an enzyme system extracted from the fly agaric, Amanita muscaria L., and their spontaneous conversion to muscaflavin and betalamic acid, respectively, and betalains. Helv Chim Acta 74:124–140
Terradas F, Wyler H (1991b) The secodopas, natural pigments in Hygrocybe cónica and Amanita muscaria Phytochem 30:3251–3253
Trezzini GF, Zryd J-P (1990) Portulaca grandiflora:A model system for the study of the biochemistry and genetics of betalain synthesis. Acta Hortic 280:581–585
Weigert L (1894) Beiträge zur Chemie der rothen Pflanzenfarbstoffe. Jahresbericht und Programm der K.K. önologischen und pomologischen Lehranstalt in Klosterneuburg, Wien
Wohlpart A, Mabry TJ (1968) The distribution and phylogenetic significance of the betalains with respect to the Centrospermae. Taxon 17:148–152
Wolyn DJ, Gabelman WH (1989) Inheritance of root and petiole pigmentation in red table beet. J Hered 80:33–38
Wyler H, Dreiding AS (1957) Kristallisiertes Betanin. Helv Chim Acta 40:191–192
Wyler H, Dreiding AS (1959) Über die Konstitution des Randenfarbstoffes Betanin: Darstellung und Abbauprodukte des Betanidins. Helv Chim Acta 42:1699–1702
Wyler H, Dreiding AS (1961a) Phytolaccanin, der Farbstoff der Kermesbeere (Phytolacca decandra L.). 1. Mitteilung zur Kenntnis der Betacyane. Helv Chim Acta 44:249–257
Wyler H, Dreiding AS (1961b) Über Betacyane, die stickstoffhatigen Farbstoffe der Centrospermen. Vorläufige Mitteilung. Experientia 17:23–25
Wyler H, Meuer U (1979) Zur Biogenese der Betacyane: Versuche mit [2-14 C]-dopaxanthin. Helv Chim Acta 62:1330–1339
Wyler H, Mabry TJ, Dreiding AS (1963) Über die Konstitution des Randenfarbstoffes Betanin: Zur Struktur des Betanidins. Helv Chim Acta 46:1745–1748
Wyler H, Wilcox ME, Dreiding AS (1965) Umwandlung eines Betacyanes in ein Betaxanthin: Synthese von Indicaxanthin aus Betanin. Helv Chim Acta 48:361–366
Wyler H, Meuer U, Bauer J, Stravs-Mombelli L (1984) Cyclodopa glucoside (=(2S)-5-(ß-D-glucopyranosyloxy)-6-hydroxyindoline-2-carboxylic acid) and its occurrence in red beet{Beta vulgaris var. rubra L.). Helv Chim Acta 67:1348–1355
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1994 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Clement, J.S., Mabry, T.J., Wyler, H., Dreiding, A.S. (1994). Chemical Review and Evolutionary Significance of the Betalains. In: Behnke, HD., Mabry, T.J. (eds) Caryophyllales. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-78220-6_11
Download citation
DOI: https://doi.org/10.1007/978-3-642-78220-6_11
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-78222-0
Online ISBN: 978-3-642-78220-6
eBook Packages: Springer Book Archive