Pigment Biosynthesis II: Betacyanins and Carotenoids

Plant Metabolism and Biotechnology

Volumn , Issue , 2011, Pages 343-371

  Sakuta, Masaaki ^a   Ohmiya, Akemi ^b  

^a OCHANOMIZU UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF VEGETABLE AND TEA SCIENCE   (Japan)

Author keywords

Betacyanins; Carotenoids; Catalyzed by zeaxanthin cleavage enzyme (CsZCD); Dihydroflavonol 4 reductase (DFR); DOPA dioxygenase (DOD); Metabolic Engineering of Carotenoids; Neoxanthin synthase (NSY); Zeaxanthin epoxidase (ZEP)

Indexed keywords

EID: 84864577006     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781119991311.ch13     Document Type: Chapter

References (164)

1. Allegra, M., Tesoriere, L. and Livrea, M.A. (2007) Betanin inhibits the myrloperoxidase/nitrite-induced oxidation of human lowdensity lipoproteins. Free Rad. Res., 41, 335-341.
2. Apel, W. and Bock, R. (2009) Enhancement of carotenoid biosynthesis in transplastomic tomatoes by induced lycopene-to-provitamin A conversion. Plant Physiol., 151, 59-66.
3. Baranska, M., Baranski, R., Shultz, H. and Nothnagel, T. (2006) Tissue-specific accumulation of carotenoids in carrot roots. Planta, 224, 1028-1037.
4. Bauberger, E. and Mayer, A.M. (1960) Effect of kinetin on formation of red pigment in seedlings of Amaranthus retroflexus. Science, 141, 1094-1095.
5. Bernhardt, A., Lechner, E., Hano, P., Schade, V., Dieterle, M., Anders, M., Dubin, M. J., Benvenuto, G., Bowler, C., Genschik, P. and Hellmann, H. (2006) CUL4 associates with DDB1 and DET1 and its downregulation affects diverse aspects of development in Arabidopsis thaliana. Plant J., 47, 591-603.
6. Biddington, N.K. and Thomas, T.H. (1973) A modified Amaranthus betacyanin bioassay for the rapid determination of cytokinins in plant extracts. Planta, 111, 183-186.
7. Biddington, N.K. and Thomas, T.H. (1977) Interaction of abscisic acid, cytokinin and gibberellins in the control of betacyanin synthesis in seedlings of Amaranthus caudatus. Physiol. Plant., 40, 312-314.
8. Bouvier, F., Dogbo, O. and Camara, B. (2003a) Biosynthesis of the food and cosmetic plant pigment bixin. Science, 300, 2089-2091.
9. Bouvier, F., Suire, C., Mutterer, J. and Camara, B. (2003b) Oxidative remodeling of chromoplast carotenoids: identification of the carotenoid dioxygenase CsCCD and CsZCD genes involved in crocus secondary metabolite biogenesis. Plant Cell, 15, 47-62.
10. Britton, G., Liaaen-Jensen, S. and Pfander, H. (2004) Carotenoids Handbook. Birkhauser, Basel, Switzerland.
11. Buckner, B., Miguel, P.S., Janick-Buckner, D. and Bennetzen, J.L. (1996) The y1 gene of maize codes for phytoene synthase. Genetics, 143, 479-488.
12. Cai, Y., Sun, M. and Corke, H. (2003) Antioxidant activity of betalains from plants of the Amaranthaceae. J. Agric. Food Chem., 51, 2288-2294.
13. Cazzonelli, C.I., Cuttriss, A. J., Cossetto, S. B., Pye, W., Crisp, P., Whelan, J., Finnegan, E. J., Turnbull, C. and Pogsona, B. J. (2009) Regulation of carotenoid composition and shoot branching in Arabidopsis by a chromatin modifying histone methyltransferase, SDG8. Plant Cell, 21, 39-53.
14. Cazzonelli, C.I. and Pogson, B.J. (2010) Source to sink: regulation of carotenoid biosynthesis in plants. Trends Plant Sci., 15, 266-274.
15. Chen, H., Shen, Y., Tan, X., Yu, L., Wang, J., Guo, L., Zhang, Y., Zhang, H., Feng, S., Strickland, E., Zheng, N. and Deng, X. W. (2006) Arabidopsis CULLIN4 forms an E3 ubiquitin ligase with RBX1 and the CDD complex in mediating light control of development. Plant Cell, 18, 1991-2004.
16. Christinet, L., Burdet, F.X., Zaiko, M., Hinz, U. and Zrÿd, J.P. (2004) Characterization and functional identification of a novel plant 4,5-extradiol dioxygenase involved in betalain pigment biosynthesis in Portulaca grandiflora. Plant Physiol., 134, 265-274.
17. Constabel, F. and Nassif-Makki, K. (1971) Betalainbildung in Beta-Calluskulturen. Ber. Deutsch Bot. Ges., 84, 629-636.
18. Cooper, C.M., Davies, N.W. and Menary, R.C. (2009) Changes in some carotenoids and apocarotenoids during flower development in Boronia megastigma (Nees). J. Agric. Food Chem., 57, 1513-1520.
19. Cunningham, F.X.J., Pogson, B., Sun, Z.R., et al. (1996) Functional analysis of the β and ε lycopene cyclase enzymes of Arabidopsis reveals a mechanism for control of cyclic carotenoid formation. Plant Cell, 8, 1613-1626.
20. Cunningham, F.X.J. and Gantt, E. (1998) Genes and enzymes of carotenoid biosynthesis in plants. Ann. Rev. Plant Physiol. Plant Mol. Biol., 49, 557-583.
21. Cunningham, F.X.J. and Gantt, E. (2001) One ring or two? Determination of ring number in carotenoids by lycopene ε-cyclases. Proc. Natl. Acad. Sci. USA, 98, 2905-2910.
22. Cunningham, F.X.J. and Gantt, E. (2005) A study in scarlet: enzymes of ketocarotenoid biosynthesis in the flowers of Adonis aestivalis. Plant J., 41, 478-492.
23. Davuluri, G.R., van Tuinen, A., Fraser, P. D., Manfredonia, A., Newman, R., Burgess, D., Brummell, D.A., King, S. R., Palys, J., Uhlig, J., Bramley, P. M., Pennings, H. M. J. and Bowler, C. (2005) Fruit-specific RNAi-mediated suppression of DET1 enhances carotenoid and flavonoid content in tomatoes. Nat. Biotechnol., 23, 890-895.
24. Delgado-Vargas, F., Jimenez, A.R. and Paredes-Lopez, O. (2000) Natural pigments: carotenoids, anthocyanins, and betalains - characteristics, biosynthesis, processing, and stability. Crit. Rev. Food Sci. Nutr., 40, 173-289.
25. Della Penna, D. and Pogson, B.J. (2006) Vitamin synthesis in plants: tocopherols and carotenoids. Ann. Rev. Plant Biol., 57, 711-738.
26. Ducreux, L.J.M., Morris, W.L., Hedley, P.E., Shepherd, T., Davies, H.V., Millam, S. and Taylor, M.A. (2005) Metabolic engineering of high carotenoid potato tubers containing enhanced levels of ß-carotene and lutein. J. Exp. Bot., 56, 81-89.
27. Dun, E.A., Philip, B., Brewer, P.B. and Beveridge, C.A. (2009) Strigolactones: discovery of the elusive shoot branching hormone. Trends Plant Sci., 14, 364-372.
28. Elliott, D.C. (1979a) Analysis of variability in the Amaranthus bioassay for cytokinins: effects of water stress on benzyladenin- and fusicoccin-dependent responses. Plant Physiol., 63, 269-273.
29. Elliott, D.C. (1979b) Analysis of variability in the Amaranthus bioassay for cytokinins: effects of "aging" excised cotyledons. Plant Physiol. 63, 274-276.
30. Elliott, D.C. (1979c) Temperature-dependent expression of betacyanin synthesis in Amaranthus seedlings. Plant Physiol., 63, 277-279.
31. Elliott, D.C. (1979d) Temperature-sensitive responses of red light-dependent betacyanin synthesis. Plant Physiol., 64, 521-524.
32. Elliott, D.C. (1983) Accumulation of cytokinin-induced betacyanin in specific cells of Amaranthus tricolor seedlings. J. Exp. Bot., 34, 67-73.
33. Endress, R. (1976) Betacyan-Akkumulation in Kallus von Portulaca grandiflora var. JR unter dem Einfluss von Phytohormonen und Cu2+-Ionen auf unterschiedlichen Grundmedium. Biochem. Physiol. Pflanzen, 169, 87-98.
34. Eugster, C.H. and Märki-Fisher, E. (1991) The chemistry of rose pigments. Angew. Chem. Int. Ed. Engl., 30, 654-672.
35. Fischer, N. and Dreiding, A.S. (1972) Biosynthesis of betaleins. On the cleavage of the aromatic ring during enxymic transformation of dopa into betalamic acid. Helv. Chem. Acta, 55, 649-658.
36. Fraser, P.D., Truesdale, M.R., Bird, C.R., Schuch, W. and Bramley, P.M. (1994) Carotenoid biosynthesis during tomato fruit development. Plant Physiol., 105, 405-413.
37. Fraser, P.D., Kiano, J.W., Truesdale, M.R., Schuch, W. and Bramley, P.M. (1999) Phytoene synthase-2 enzyme activity in tomato does not contribute to carotenoid synthesis in ripening fruit. Plant Mol. Biol., 40, 687-698.
38. Fraser, P. D., Romer, S., Shipton, C. A., Mills, P. B., Kiano, J.W., Misawa, N., Drake, R.G., Schuch, W. and Bramley, P.M. (2002) Evaluation of transgenic tomato plants expressing an additional phytoene synthase in a fruit-specific manner. Proc. Natl. Acad. Sci. USA, 99, 1092-1097.
39. Fraser, P.D. and Bramley, P.M. (2004) The biosynthesis and nutritional uses of carotenoids. Prog. Lipid Res., 43, 228-265.
40. Fray, R. G., Wallace, A., Fraser, P.D., Valero, D., Hedden, P., Bramley, P. M. and Grierson, D. (1995) Constitutive expression of a fruit phytoene synthase gene in transgenic tomatoes causes dwarfism by redirecting metabolites from the gibberellin pathway. Plant J., 8, 693-701.
41. Fujisawa, M., Takita, E., Harada, H., Sakurai, N., Suzuki, H., Ohyama, K., Shibata, D. and Misawa, N. (2009) Pathway engineering of Brassica napus seeds using multiple key enzyme genes involved in ketocarotenoid formation. J. Exp. Bot., 60, 1319-1332.
42. Galpaz, N., Ronen, G., Khalfa, Z., Zamir, D. and Hirschberg, J. (2006) A chromoplastspecific carotenoid biosynthesis pathway is revealed by cloning of the tomato whiteflower locus. Plant Cell, 18, 1947-1960.
43. Garay, A.S. and Towers, G.H.N. (1966) Studies on the biosynthesis of amaranthin. Can. J. Bot., 44, 231-236.
44. Gerjets, T. and Sandmann, G. (2006) Ketocarotenoid formation in transgenic potato. J. Exp. Bot., 57, 3639-3645.
45. Gerjets, T., Sandmann, M., Zhu, C. and Sandmann, G. (2007) Metabolic engineering of ketocarotenoid biosynthesis in leaves and flowers of tobacco species Biotech. J., 2, 1263-1269.
46. Girod, P.A. and Zrÿd, J.P. (1991) Biogenesis of betalains: purification and partial characterization of Dopa 4,5-dioxygenase from Amanita muscaria. Phytochemistry, 30, 169-174.
47. Giuliano, G., Bartley, G.E. and Scolnik, P.A. (1993) Regulation of carotenoid biosynthesis during tomato development. Plant Cell, 5, 379-387.
48. Gompel, N., Prud'homme, B., Wittkopp, P.J., Kassner, V.A. and Carroll, S.B. (2005) Chance caught on the wing: cis-regulatory evolution and the origin of pigment patterns in Drosophila. Nature, 433, 481-487.
49. Green, B.R. and Durnford, D.G. (1996) The chlorophyll-carotenoid proteins of oxygenic photosynthesis. Ann. Rev. Plant Physiol. Plant Mol. Biol., 47, 685-714.
50. Guruprasad, K.N. and Laloraya, M.M. (1980) Dissmilarity in the inhibition of betacyanin synthesis caused by gibberellic acid and abscisic acid. Biochem. Physiol. Pflanzen, 175, 582-586.
51. Hagenimana, V., Carey, E.E., Gichuki, S.T., Oyunga, M.A. and Inumgi, J.K. (1999) Carotenoid contents in fresh, dried and processed sweetpotato products. Ecol. Food Nutr., 37, 455-473.
52. Harborne, J.B. (1996) The evolution of flavonoid pigments in plants, in Comparative Phytochemistry (ed. T. Swain), Academic Press, London, pp. 271-295.
53. Heuer, S. and 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.
54. Hinz, U.G., Fivaz, J., Girod, P.A. and Zrÿd, J.P. (1997) The gene coding for the DOPA dioxygenase involved in betalain biosynthesis in Amanita muscaria and its regulation. Mol. Gen. Genet., 256, 1-6.
55. Hirano, H., Sakuta, M. and Komamine, A. (1996) Inhibition of betacyanin accummulation by abscisic acid in suspension cultures of Phytolacca americana. Z. Naturforsch., 51c, 818-822.
56. Hornero-Méndez, D., Gómez-Ladrón de Guevara, R. and Minguez-Mosquera, M.I. (2000) Carotenoid biosynthesis changes in five red pepper (Capsicum annuum L.) cultivars during ripening. Cultivar selection for breeding. J. Agric. Food Chem., 48, 3857-3864.
57. Howitt, C.A. and Pogson, B. (2006) Carotenoid accumulation and function in seeds and non-green tissues. Plant Cell Environ., 29, 435-445.
58. Huang, F-C., Horvath, G., Molnar, P., Turcsi, E., Deli, J., Schrader, J., Sandmann, G., Schmidt, H. and Schwab, W. (2009a) Substrate promiscuity of RdCCD1, a carotenoid cleavage oxygenase from Rosa damascena. Phytochemistry, 70, 457-464.
59. Huang, F.-C., Molnar, P. and Schwab, W. (2009b) Cloning and functional characterization of carotenoid cleavage dioxygenase 4 genes. J. Exp. Bot., 60, 3011-3022.
60. Impellizzeri, G. and Piattelli, M. (1972) Biosynthesis of indicaxanthin in Opuntia ficusindica fruit. Phytochemistry, 11, 2499-2502.
61. Isaacson, T., Ronen, G., Zamir, D. and Hirschberg, J. (2002) Cloning of tangerine from tomato reveals a carotenoid isomerase essential for the production of β-carotene and xanthophylls in plants. Plant Cell, 14, 333-342.
62. Isaacson, T., Ohad, I., Beyer, P. and Hirschberg, J. (2004) Analysis in vitro of the enzyme CRTISO establishes a poly-cis-carotenoid biosynthesis pathway in plants. Plant Physiol., 136, 4246-4255.
63. Iwashina,T. (2001) Flavonoids and their distribution in plant families containing the betalain pigments (Review). Ann. Tsukuba Bot. Gard., 20, 11-74.
64. Iwashina, T., Ootani, S. and Hayashi, K. (1988) On the pigmentation spherical bodies and crystals in tepals of Cactaceous species in reference to the nature of betalains or flavonols. Bot. Mag. Tokyo, 101, 175-184.
65. Kanner, J., Harel, S. and Granit, R. (2001) Betalains - a new class of dietary cationized antioxidants. J. Agric. Food Chem., 49, 5178-5185.
66. Kato,M., Ikoma, Y., Matsumoto, H., Sugiura, M., Hyodo, H. and Yano, M. (2004) Accumulation of carotenoids and expression of carotenoid biosynthetic genes during maturation in citrus fruit. Plant Physiol., 134, 824-837.
67. Kim, J., Smith, J.J., Tian, L. and Dellapenna, D. (2009) The evolution and function of carotenoid hydroxylases in Arabidopsis. Plant Cell Physiol., 50, 463-479.
68. Kishimoto, S., Maoka, T., Nakayama, M. and Ohmiya, A. (2004) Carotenoid composition in petals of chrysanthemum (Dendranthema grandiflorum (Ramat.) Kitamura). Phytochemistry, 65, 2781-2787.
69. Kishimoto, S., Maoka, T., Sumitomo, K. and Ohmiya, A. (2005) Analysis of carotenoid composition in petals of calendula (Calendula officinalis L.). Biosci. Biotechnol. Biochem., 69, 2122-2128.
70. Kishimoto, S. and Ohmiya, A. (2006) Regulation of carotenoid biosynthesis in petals and leaves of chrysanthemum (Chrysanthemum morifolium Ramat.). Physiol. Plant., 128, 437-447.
71. Koelher, H.K. (1972a) Action of inhibitors of protein and nucleic acid synthesis on lightdependent and kinetin-stimulated betcyanin synthesis. Phytochemistry, 11, 127-132.
72. Koelher, H.K. (1972b) Phytocontrol of betacyanin synthesis in Amaranthus caudatus seedlings in the presence of kinetin. Phytochemistry, 11, 133-137.
73. Koelher, H.K., Kochhar, S. and Mohr, H. (1981) Action of light and kinetin on betalain synthesis in seedlings of Amaranthus caudatus: A two-factor analysis. Ber. Deutsch Bot. Ges., 94, 27-34.
74. Koes, R., Quattrocchio, F. and Mol, J. (1994) The flavonoid biosynthetic pathway in plants: function and evolution. BioEssays, 16, 123-132.
75. Kujala, T., Loponen, J. and Pihlaja, K. (2001) Betalains and phenolics in red beetroot (Beta vulgaris) peel extracts: extraction and characterisation. Z. Naturforsch., 56c, 343-348.
76. Kurilich, A.C. and Juvik, J.A. (1999) Quantification of carotenoid and tocopherol antioxidants in Zea mays. J. Agric. Food Chem., 47, 1948-1955.
77. Lee, C.H., Wettasinghe, M., Bolling, B.W., Ji, L.L. and Parkin, K.L. (2005) Betalains, phase II enzyme-inducing components from red beetroot (Beta vulgaris L.) extracts. Nutr. Cancer, 53, 91-103.
78. Li, F., Murillo, C. and Wurtzel, E.T. (2007) Maize Y9 encodes a product essential for 15-cis-ζ -carotene isomerization. Plant Physiol., 144, 1181-1189.
79. Li, L., Paolillo, D.J., Parthasarathy, M.V., DiMuzio, E.M. and Garvin, D.F. (2001) A novel gene mutation that confers abnormal patterns of β-carotene accumulation in cauliflower (Brassica oleracea var. botrytis). Plant J., 26, 59-67.
80. Liu, Y., Roof, S., Ye, Z., Barry, C., Tuinen, A., Vrebalov, J., Bowler, C. and Giovannoni, J. (2004) Manipulation of light signal transduction as a means of modifying fruit nutritional quality in tomato. Proc. Natl. Acad. Sci. USA, 101, 9897-9902.
81. Lopez, A.B., Van Eck, J., Conlin, B.J., Paolillo, D.J., O'Neill, J. and Li, L. (2008) Effect of the cauliflower Or transgene on carotenoid accumulation and chromoplast formation in transgenic potato tubers. J. Exp. Bot., 59, 213-223.
82. Lu, S., Van Eck, J., Zhou, X., Lopez, A.B., O'Halloran, D.M., Cosman, K.M, Conlin, B.J., Paolillo, D. J., Garvin, D.F., Vrebalov, J., Kochian, L.V., Küpper, H., Earle, E.D., Cao, J. and Li, L. (2006) The cauliflower Or gene encodes a DnaJ cysteine-rich domaincontaining protein that mediates high levels of β-carotene accumulation. Plant Cell, 18, 3594-3605.
83. Mabry, T.J. (1980) Betalains, in Secondary Plant Products (eds E.A. Bell and B.V. Charlwood), Encyclopedia of Plant Physiology Vol. 8, Springer-Verlag, Berlin, pp. 513-533.
84. Matsumoto, H., Ikoma, Y., Kato, M., Kuniga, T., Nakajima, N. and Yoshida, T. (2007) Quantification of carotenoids in Citrus fruit by LC-MS and comparison of patterns of seasonal changes for carotenoids among Citrus varieties. J. Agric. Food Chem., 55, 2356-2368.
85. Matus, Z., Molnar, P. and Szabo, L. (1993) Main carotenoids in pressed seeds (Cucurbitae semen) of pumpkin (Cucurbita pepo convar.pepo var. styriaca). Acta Pharm. Hung., 63, 247-256.
86. Mayne, S.T. (1996) β-Carotene, carotenoids and disease prevention in humans. FASEB J., 10, 690-701.
87. McGraw, K.J., Hill, G.E., Stradi, R. and Parker, R.S. (2001) The influence of carotenoid acquisition and utilization on the maintenance of species-typical plumage pigmentation in male American goldfinches (Carduelis tristis) and northern cardinals (Cardinalis cardinalis). Physiol. Biochem. Zool., 74, 843-852.
88. Miller, H.E., Rosler, H., Wohlpart, A., Wyler, H., Wilcox, M.E., Frohofer, H., Mabry, T.J. and Dreiding, A.S. (1968) Biogenese der betalaine. Biotransformation von Dopa und tyrosin in den betalaminsaureteil des betanins. Vorläufige Mitteilung. Helv. Chim. Acta, 51, 1470-1474.
89. Misawa, N. (2009) Pathway engineering of plants toward astaxanthin production. Plant Biotech., 26, 93-99.
90. Moehs, C.P., Tian, L., Osteryoung, K.W. and Della Penna, D. (2001) Analysis of carotenoid biosynthetic gene expression during marigold petal development. Plant Mol. Biol., 45, 281-293.
91. Molnar, P. and Szabolcs, J. (1980) Occurrence of 15-cis-violaxanthin in Viola tricolor. Phytochemistry, 19, 623-627.
92. Mueller, L.A., Hinz, U., Uze, M., Sautter, C. and Zrÿd, J.P. (1997a) Biochemical complementation of the betalain biosynthetic pathway in Portulaca grandiflora by a fungal 3,4-dihydroxyphenylalanine dioxygenase. Planta, 203, 260-263.
93. Mueller, L.A., Hinz, U. and Zrÿd, J.P. (1997b) The formation of betalamic acid and muscaflavin by recombinant dopa-dioxygenase from Amanita. Phytochemistry, 44, 567-569.
94. Nambara, E. and Marion-Poll, A. (2005) Abscisic acid biosynthesis and catabolism. Ann. Rev. Plant Biol., 56, 165-185.
95. Nassif-Makki, H. and Constabel, F. (1972) Zur Bedeutung von tyrosin als vorstufe der betalainsynthese. Z. Pflanzenphysiol. 67, 201-206.
96. Nicola, M.G., Piattelli, M. and Amico, V. (1973a) Phytocontrol of betaxanthin synthesis in Celosia plumose seedlings. Phytochemistry, 12, 353-357.
97. Nicola, M.G., Piattelli, M. and Amico, V. (1973b) Effect of continuous far red on betaxanthin and betacyanin synthesis. Phytochemistry, 12, 2163-2166.
98. Nicola, M.G., Amico, V. and Piattelli, M. (1974) Effect of white and far-red light on betalain formation. Phytochemistry, 13, 439-442.
99. Niyogi, K. (2000) Safety valves for photosynthesis. Curr. Opin. Plant Biol., 3, 455-460.
100. Ohmiya, A. (2009) Carotenoid cleavage dioxygenases and their apocarotenoid products in plants. Plant Biotech., 26, 351-358.
101. Ohmiya, A., Kishimoto, S., Aida, R., Yoshioka, S. and Sumitomo, K. (2006) Carotenoid cleavage dioxygenase (CmCCD4a) contributes to white color formation in chrysanthemum petals. Plant Physiol., 142, 1193-1201.
102. Paine, J.A., Shipton, C.A., Chaggar, S., Howells, R.M, Kennedy, M.J., Vernon, G., Wright, S.Y., Hinchuliffe, E., Adams, J.L., Silverstone, A.L. and Drake, R. (2005) Improving the nutritional value of golden rice through increased pro-vitamin A content. Nat. Biotechnol., 23, 482-487.
103. Park, H., Kreunen, S.S., Cuttriss, A.J., DellaPenna, D. and Pogson, B.J. (2002) Identification of the carotenoid isomerase provides insight into carotenoid biosynthesis, prolamellar formation, and photomorphogenesis. Plant Cell, 14, 321-332.
104. Piattelli, M. (1976) Betalains, in Chemistry and Biochemistry of Plant Pigments, Vol. 1 (2nd edn) (ed. T.W. Goodwin), Academic Press, New York, pp. 560-596.
105. Römer, S., Hugueney, P., Bouvier, F., Camara, B. and Kuntz, M. (1993) Expression of the genes encoding the early carotenoid biosynthetic-enzymes in Capsicum annuum. Biochem. Biophys. Res. Commun., 196, 1414-1421.
106. Römer, S., Lübeck, J., Kauder, F., Steiger, S., Adomat, C. and Sandmann, G. (2002) Genetic engineering of a zeaxanthin-rich potato by antisence inactivation and co-supression of carotenoid epoxidation. Metab. Eng., 4, 263-272.
107. Saito, K. and Komamine, A. (1976) Biosynthesis of stizolobinic acid and stizolobic acid in higher plants: A enzyme system(s) catalyzing the conversion of dihydroxyphenylalanine into stizolobinic acid and stizolobic acid from etiolated seedlings of Stizolobium hassjoo. Eur. J. Biochem., 68, 237-243.
108. Saito, K. and Komamine, A. (1978) Biosynthesis of stizolobinic acid and stizolobic acid in higher plants: Stizolobinic acid synthase and stizolobic acid synthase, new enzymes which catalyze the reaction sequences leading to the formation of stizolobinic acid and stizolobic acid from 3,4-dihydroxyphenylalanine in Stizolobium hassjoo. Eur. J. Biochem., 82, 385-392.
109. Sakuta, M., Hirano, H. and Komamine, A. (1991) Stimulation by 2,4-dichlorophenoxyacetic acid of betacyanin accumulation in suspension cultures of Phytolacca americana. Physiol. Plant., 83, 154-158.
110. Sandmann, G., Romer, S. and Fraser, P.D. (2006) Understanding carotenoid metabolism as a necessity for genetic engineering of crop plants. Metabolic Eng., 8, 291-302.
111. Sasaki, N., Adachi, T., Koda, T. and Ozeki, Y. (2004) Detection of UDP-glucose:cyclo-DOPA 5-O-glucosyltransferase activity in four o'clocks (Mirabilis jalapa L.). FEBS Lett., 568, 159-162.
112. Sasaki, N., Abe, Y., Wada, K., Koda, T., Goda, Y., Adachi, T. and Ozeki, Y. (2005a) Amaranthin in feather cockscombs is synthesized via glucuronylation at the cyclo-DOPA glucoside step in the betacyanin biosynthetic pathway. J. Plant Res., 118, 439-442.
113. Sasaki, N., Wada, K., Koda, T., Kasahara, K., Adachi, T. and Ozeki, Y. (2005b) Isolation and characterization of cDNAs encoding an enzyme with glucosyltransferase activity for cyclo-DOPA from four o'clocks and feather cockscombs. Plant Cell Physiol., 46, 666-670.
114. Sasaki, N., Abe, Y., Goda, Y., Adachi, T., Kasahara, K. and Ozeki, Y. (2009) Detection of DOPA 4,5-dioxygenase(DOD) activity using recombinant protein prepared from Escherichia coli cells harboring cDNA encoding DOD from Mirabilis jalapa. Plant Cell Physiol., 50, 1012-1016.
115. Schaub, P., Al-Babili, S., Drake, R. and Beyer, P. (2005) Why is Golden Rice (yellow) instead of red? Plant Physiol., 138, 441-450.
116. Schledz, M., Al-Babili, S., von Lintig, J, Haubruck, H., Rabbani, S., Kleinig, H. and Beyer, P. (1996) Phytoene synthase from Narcissus pseudonarcissus: functional expression, galactolipid requirement, topological distribution in chromoplasts and induction during flowering. Plant J., 10, 781-792
117. Schliemann, W., Kobayashi, N. and Strack, D. (1999) The decisive step in betaxanthin biosynthesis is a spontaneous reaction. Plant Physiol., 119, 1217-1232.
118. Schwartz, S.H., Tan, B.C., Gage, D.A., Zeevaart, J.A.D. and McCarty, D.R. (1997) Specific oxidative cleavage of carotenoids by VP14 of maize. Science, 276, 1872-1874.
119. Schwartz, S.H., Qin, X. and Loewen, M. (2004) The biochemical characterization of two carotenoid cleavage enzymes from Arabidopsis indicates that a carotenoid-derived compound inhibits lateral branching. J. Biol. Chem., 279, 46940-46945.
120. Sciuto, S., Oriente, G. and Piatelli, M. (1972) Betanidin glycosylation in Opuntia dillenii. Phytochemistry, 11, 2259-2262.
121. Sciuto, S., Oriente, G., Piattelli, M., Impelizzeri, G. and Amico, V. (1974) Biosynthesis of amaranthin in Celosia plumosa. Phytochemistry, 13, 947-951.
122. Shapiro, M.D., Marks, M.E., Peichel, C.L., Blackman, B.K., Nereng, K.S., Jonsson, B., Schluter, D. and Kingsley, D.M. (2004) Genetic and developmental basis of evolutionary pelvic reduction in threespine sticklebacks. Nature, 428, 717-723.
123. Shewmaker, C.K., Sheehy, J.A., Daley, M., Colburn, S. and Ke, D.Y. (1999) Seed-specific overexpression of phytoene synthase: increase in carotenoids and other metabolic effects. Plant J., 20, 401-412.
124. Shimada, S., Takahashi, K., Sato, Y. and Sakuta, M. (2004) Dihydroflavonol 4-reductase cDNA from non-anthocyanin-producing species in the Caryophyllales. Plant Cell Physiol., 45, 1290-1298.
125. Shimada, S., Inoue, T.Y. and Sakuta, M. (2005) Anthocyanidin synthase in nonanthocyanin-producing Caryophyllales species. Plant J., 44, 950-959.
126. Shimada, S., Otsuki, H. and Sakuta, M. (2007) Transcriptional control of anthocyanin biosynthetic genes in the Caryophyllales. J. Exp. Bot., 58, 957-967.
127. Simkin, A.J., Zhu, C., Kuntz, M. and Sandmann, G. (2003) Light-dark regulation of carotenoid biosynthesis in pepper (Capsicum annuum) leaves. J. Plant Physiol., 160, 439-443.
128. Simkin, A.J., Schwartz, S. H., Auldridge, M., Taylor, M. G. and Klee, H. J. (2004a) The tomato carotenoid cleavage dioxygenase 1 genes contribute to the formation of the flavor volatiles β-ionone, pseudoionone, and geranylacetone. Plant J., 40, 882-892.
129. Simkin, A. J., Underwoo, B. A., Auldridge, M., Loucas, H.M., Shibuya, K., Schmelz, E., Clark, D.G. and Klee, H. J. (2004b) Circadian regulation of the PhCCD1 carotenoid cleavage dioxygenase controls emission of β-ionone, a fragrance volatile of petunia flowers. Plant Physiol., 136, 3504-3514.
130. Spasic, M., Milic, B. and Obrenivic, S. (1985) Superoxide dismutase activity versus betacyanin induction under continuous red illumination in Amaranthus seedlings. Biochem. Physiol. Pflanzen, 180, 319-322.
131. Stafford, H.A. (1990) Flavonoid evolution: an enzymic approach. Plant Physiol., 96, 680-685.
132. Stafford, H.A. (1994) Anthocyanins and betalains: evolution of the mutually exclusive pathways. Plant Sci., 101, 91-98.
133. Steiner, U., Schliemann, W. and Strack, D. (1996) Assay for tyrosine hydroxylation activity of tyrosinase from betalain-forming plants and cell cultures. Anal. Biochem., 238, 72-75.
134. Steiner, U., Schliemann,W., Böhm, H. and Strack, D. (1999) Tyrosinase involved in betalain biosynthesis of higher plants. Planta, 208, 114-124.
135. Stintzing, F.C., Herbach, K.M., Mosshammer, M.R., Carle, R., Yi, W., Sellappan, S., Akoh, C.C., Bunch, R. and Felker, P. (2005) Color, betalain pattern, and antioxidant properties of cactus pear (Opuntia spp.) clones. J. Agric. Food Chem., 53, 442-451.
136. Stobart, A.K. and Kinsman, L.T. (1977) The hormonal control of betacyanin synthesis in Amaranthus caudatus. Phytochemistry, 16, 1139-1142.
137. Strack, D. and Schliemann, W. (2001) Bifunctional polyphenol oxidases: novel functions in plant pigment biosynthesis. Angew. Chem. Int. Ed., 40, 3791-3794.
138. Strack, D., Vogt, T. and Schliemann, W. (2003) Recent advance in betalain research. Phytochemistry, 62, 247-269.
139. Straus, W. (1961) Studies on the chromoplasts of carrots. Protoplasma, 53, 405-421.
140. Suzuki, S., Nishihara, M., Nakatsuka, T., Misawa, N., Ogiwara, I., and Yamamura, S. (2007) Flower color alteration in Lotus Japonicus by modification of the carotenoid biosynthetic pathway. Plant Cell Rep., 26, 951-959.
141. Tan, B.C., Schwartz, S.H., Zeevaart, J.A.D. and McCarty, D.R. (1997) Genetic control of abscisic acid biosynthesis in maize. Proc. Natl. Acad. Sci. USA, 94, 12235-12240.
142. Tan, B.C., Joseph, L. M., Deng, W.T., Liu, L., Li, Q.B., Cline, K. and McCarty, D.R. (2003) Molecular characterization of the Arabidopsis 9-cis epoxycarotenoid dioxygenase gene family. Plant J., 35, 44-56.
143. Tanaka, Y., Sasaki, N. and Ohmiya, A. (2008) Biosynthesis of plant pigments: anthocyanins, betalains and carotenoids. Plant J., 54, 733-749.
144. Tesoriere, L., Butera, D., Allegra, M., Fazzari, M. and Livrea, M.A. (2005) 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. J. Agric. Food Chem., 53, 1266-1270.
145. Tesoriere, L., Fazzari, M., Angileri, F., Gentile, C. and Livrea, M.A. (2008) In vitro digestion of betalainic foods. Stability and bioaccessibility of betaxanthins and betacyanins and antioxidative potential of food digesta. J. Agric. Food Chem., 56, 10487-10492.
146. Tevini, M. and Steinmuller, D. (1985) Composition and function of plastoglobuli. II. Lipid composition of leaves and plastogulobuli during senescence. Planta, 163, 91-96.
147. Tian, L., Musetti, V., Kim, J., Magallanes-Lundback, M. and DellaPenna, D. (2004) The Arabidopsis LUT1 locus encodes a member of the cytochrome P450 family that is required for carotenoid ε-ring hydroxylation activity. Proc. Natl. Acad. Sci. USA, 101, 402-407.
148. Valadon, L.R.G. and Mummery, R.S. (1968) Carotenoids in floral parts of a narcissus, a daffodil and a tulip. Biochem. J., 106, 479-484.
149. Vishnevetsky, M., Marianna Ovadis, M. and Vainstein, A. (1999) Carotenoid sequestration in plants: the role of carotenoid associated proteins. Trends Plant Sci., 4, 232-235.
150. Vogt, T. (2002) Substrate specificity and sequence analysis define a polyphyletic origin of betanidin 5- and 6-O-glucosyltransferase from Dorotheanthus bellidiformis. Planta, 214, 492-495.
151. Vogt, T., Zimmermann, E., Grimm, R., Meyer, M. and Strack, D. (1997) Are the characteristics of betanidin glucosyltransferases from cell-suspension cultures of Dorotheanthus bellidiformis indicative of their phylogenetic relationship with flavonoid glucosyltransferases? Planta, 203, 349-361.
152. von Lintig, J., Welsch, R., Bonk, M., Giuliano, G., Batschauer, A. and Kleinig, H. (1997) Light-dependent regulation of carotenoid biosynthesis occurs at the level of phytoene synthase expression and is mediated by phytochrome in Sinapis alba and Arabidopsis thaliana seedlings. Plant J., 12, 625-634.
153. Wang, S., Liu, J., Feng, Y., Niu, X., Giovannoni, J. and Liu, Y. (2008) Altered plastid levels and potential for improved fruit nutrient content by downregulation of the tomato DDB1-interacting protein CUL4. Plant J., 55, 89-103.
154. Welsch, R., Maass, D., Voegel, T., DellaPenna, D. and Beyer (2007) Transcription factor RAP2.2 and its interacting partner SINAT2: stable elements in the carotenogenesis of Arabidopsis leaves. Plant Physiol., 145, 1073-1085.
155. Wyler, H., Meuer, U., Bauer, J. and Stravas-Mombelli, L. (1984) Cyclodopa glucoside (=(2S)-5-(-β-D-glucopyranosyloxy)-6-hydroxyindoline-2-carboxylic acid) and its occurrence in red beet (Beta vulgaris var. rubra L.). Helv. Chim. Acta, 67, 1348-1355.
156. Xu, J., Tao, N., Liu, Q. and Deng, X. (2006) Presence of diverse ratios of lycopene/β-carotene in five pink or red-fleshed citrus cultivars. Sci. Hort., 108, 181-184.
157. Yamagishi, M., Kishimoto, S. and Nakayama, M. (2010) Carotenoid composition and changes in expression of carotenoid biosynthetic genes in tepals of Asiatic hybrid lily. Plant Breed., 129, 100-107.
158. Yamamizo, C., Kishimoto, S. and Ohmiya, A. (2010) Carotenoid composition and carotenogenic gene expression during Ipomoea petal development. J. Exp. Bot., 61, 709-719.
159. Yamamoto, K., Kobayashi, N., Yoshitama, K., Teramoto, S. and Komamine, A. (2001) Isolation and purification of tyrosine hydroxylase from callus cultures of Portulaca grandiflora. Plant Cell Physiol., 42, 969-975.
160. Ye, X., Al-Babili, S., Kloti, A., Zhang, J., Lucca, P., Beyer, P. and Potrykus, I. (2000) Engineering the provitamin A (β-carotene) biosynthetic pathway into (carotenoid-free) rice endosperm. Science, 287, 303-305.
161. Zhu, C., Yamamura, S., Nishihara, M., Koiwa, H. and Sandmann, G. (2003) cDNA for the synthesis of cyclic carotenoids in petals of Gentiana lutea and their regulation during flower development. Biochim. Biophys. Acta, 1625, 305-308.
162. Zhu, C., Gerjets, T. and Sandmann, G. (2007) Nicotiana glauca engineered for the production of ketocarotenoids in flowers and leaves by expressing the cyanobacterial crtO ketolase gene. Transgenic Res., 16, 813-821.
163. Zhu, C., Naqvia, S., Breitenbach, J., Sandmannb, G., Christoua, P. and Capella, T. (2008) Combinatorial genetic transformation generates a library of metabolic phenotypes for the carotenoid pathway in maize. Proc. Natl. Acad. Sci. USA, 105, 18232-18237.
164. Zhu, C., Naqvi, S., Capell, T. and Christou, P. (2009) Metabolic engineering of ketocarotenoid biosynthesis in higher plants. Arch. Biochem. Biophys., 483, 182-190.