Carotenoids, their diversity and carotenogenesis in cyanobacteria

Handbook on Cyanobacteria: Biochemistry, Biotechnology and Applications

Volumn , Issue , 2009, Pages 399-428

  Takaichi, Shinichi ^a   Mochimaru, Mari ^b  

^a NIPPON MEDICAL SCHOOL   (Japan)

^b KOMAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 69949149891     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (90)

1. Aakermann, T., Skulberg, O. M., & Liaaen-Jensen, S. (1992) A comparison of the carotenoids of strains of Oscillatoria and Spirulina (cyanobacteria). Biochem. System. Ecol. 20: 761-769
2. Armstrong, G. A. (1997) Genetics of eubacterial carotenoid biosynthesis: a colorful tale. Annu. Rev. Microbiol. 51: 629-659
3. Bartley, G. E., Scolnik, P. A., & Beyer, P. (1999) Two Arabidopsis thaliana carotene desaturases, phytoene desaturase and ζ-carotene desaturase, expressed in Escherichia coli, catalyze a poly-cis pathway to yield pro-lycopene. Eur. J. Biochem. 259: 396-403
4. Boucher, Y., & Doolitttle W. F. (2000) The role of lateral gene transfer in the evolution of isoprenoid biosynthesis pathways. Mol. Microbiol. 37: 703-716
5. Breitenbach, J., Fernández-González, B., Vioque, A., & Sandmann G. (1998) A higher-plant type ζ-carotene desaturase in the cyanobacterium Synechocystis PCC6803. Plant Mol. Biol. 36: 725-732
6. Breitenbach, J., Vioque, A., & Sandmann, G. (2001) Gene sll0033 from Synechocystis 6803 encodes a carotenoid isomerase involved in the biosynthesis of all-E lycopene. Z. Naturforsch. 56 c: 915-917
7. Britton, G., Liaaen-Jensen, S., & Pfander, H. (2004) Carotenoids, Handbook. Birkhäuser Verlag, Basel Buchecker, R., Liaaen-Jensen, S., Borch, G., & Siegelman, H. W. (1976) Carotenoids of Anacystis nidulans, structures of caloxanthin and nostoxanthin. Phytochemistry. 15: 1015-1018
8. Castenholz, R.W. (2001) Phylum BX. Cyanobacteria. In: Bergey's Manual of Systematic Bacteriology, Second Edition, vol. One, pp. 473-599, Boone, D. R., & Castenholz, R. W. (eds.), Springer, New York
9. Chamovitz, D., Misawa, N., Sandmann, G., & Hirschberg, J. (1992) Molecular cloning and expression in Escherichia coli of a cyanobacterial gene coding for phytoene synthase, a carotenoid biosynthesis enzyme. FEBS Lett. 296: 305-310
10. Cunningham Jr., F. X. (2002) Regulation of carotenoid synthesis and accumulation in plants. Pure Appl. Chem. 74: 1409-1417
11. Cunningham Jr., F. X., Sun, Z., Chamovitz, D., Hirschberg, J., & Gantt, E. (1994) Molecular structure and enzymatic function of lycopene cyclase from the cyanobacterium Synechococcus sp strain PCC7942. Plant Cell. 6: 1107-1121
12. Cunningham Jr., F. X., & Gantt, E. (2001) One ring or two? Determination of ring number in carotenoids by lycopene β-cyclases. Proc. Natl. Acad. Sci. USA. 98: 2905-2910
13. Dembitsky, V. M. (2005) Astonishing diversity of natural surfactants: 3. Carotenoid glycosides and isoprenoid glycolipids. Lipids. 40: 535-557
14. Eisenreich, W., Bacher, A., Arigoni, D., & Rohdich, F. (2004) Biosynthesis of isoprenoids via the non-mevalonate pathway. Cell. Mol. Life Sci. 61: 1401-1426
15. Fernández-González, B., Sandmann, G., & Vioque, A. (1997) A new type of asymmetrically acting β-carotene ketolase is required for the synthesis of echinenone in the cyanobacterium Synechocystis sp. PCC 6803. J. Biol. Chem. 272: 9728-9733
16. Ferreira, K. N., Iverson, T. M., Maghlaoui, K., Barber, J., & Iwata, S. (2004) Architecture of the photosynthetic oxygen-evolving center. Science. 303: 1831-1838
17. Foss, P., Skulberg, O. M., Kilaas, L., & Liaaen-Jensen, S. (1986) The carbohydrate moieties bound to the carotenoids myxol and oscillol and their chemosystematic applications. Phytochemistry. 25: 1127-1132
18. Francis, G. W., Hertzberg, S., Andersen, K., & Liaaen-Jensen, S. (1970) New carotenoid glycosides from Oscillatoria limosa. Phytochemistry. 9: 629-635
19. Frank, H. A., Young, A. J., Britton, G., & Cogdell, R. J. (1999) The Photochemistry of Carotenoids, Kluwer Academic Publishers, Dordrecht
20. Frigaard, N.-U., Maresca, J. A., Yunker, C. E., Jones, A. D., & Bryant, D. A. (2004) Genetic manipulation of carotenoid biosynthesis in the green sulfur bacterium Chlorobium. tepidum. J. Bacteriol. 186: 5210-5220
21. Goodwin T.W. (1980) The Biochemistry of the Carotenoids, vol. 1. Plants, 2nd ed., Chapman and Hall, London
22. Graham, J. E., & Bryant, D. A. (2008) The biosynthetic pathway for synechoxanthin, an aromatic carotenoid synthesized by the euryhaline, unicellular cyanobacterium Synechococcus sp. strain PCC 7002. J. Bacteriol. 190: 7966-7974
23. Graham, J. E., & Bryant, D. A. (2009) The biosynthetic pathway for myxol-2' fucoside (myxoxanthophyll) in the cyanobacterium Synechococcus sp. strain PCC 7002. J. Bacteriol. 191: 3292-3300
24. Graham, J. E., Lecomte, J. T. J., & Bryant, D. A. (2008) Synechoxanthin, an aromatic C40 xanthophyll that is a major carotenoid in the cyanobacterium Synechococcus sp. PCC 7002. J. Nat. Prod. 71: 1647-1650
25. Harker, M., & Hirschberg, J. (1998) Molecular biology of carotenoid biosynthesis in photosynthetic organisms. Methods Enzymol. 297: 244-263
26. Hemmi, H., Ikejiri, S., Nakayama, T., & Nishino, T. (2003) Fusion-type lycopene β-cyclase from a thermoacidophilic archaeon Sulfolobus solfataricus. Biochem. Biophys. Res. Commun. 305: 586-591
27. Herbert, R. A., Gall, A., Maoka, T., Cogdell, R. J., Robert, B., Takaichi, S., & Schwabe, S. (2008) Phototrophic purple sulfur bacteria as heat engines in the South Andros Black Hole. Photosynth. Res. 95: 261-268
28. Hertzberg, S., & Liaaen-Jensen, S. (1969a) The structure of myxoxanthophyll. Phytochemistry. 8: 1259-1280
29. Hertzberg, S,. & Liaaen-Jensen, S. (1969b) The structure of oscillaxanthin. Phytochemistry. 8: 1281-1292
30. Hertzberg, S., & Liaaen-Jensen, S. (1971) The constitution of aphnizophyll. Phytochemistry. 10: 3251-3252
31. Hertzberg, S., Liaaen-Jensen, S., & Siegelman, H. W. (1971) The carotenoids of blue-green algae. Phytochemistry. 10: 3121-3127
32. Hirschberg, J., & Chamovitz, D. (1994) Carotenoids in cyanobacteria. In: The Molecular Biology of Cyanobacteria, pp. 559-579, Bryant, D. A. (ed.), Kluwer Academic Publishers, Dordrecht
33. Huang, J.-C., Wang, Y., Sandmann, G., & Chen, F. (2006) Isolation and characterization of a carotenoid oxygenase gene from Chlorella zofingiensis (Chlorophyta). Appl. Microbiol. Biotechnol. 71: 473-479
34. IUPAC Commission on Nomenclature of Organic Chemistry and the IUPAC-IUB Commission on Biochemical Nomenclature (1975) Nomenclature of carotenoids. Pure Appl. Chem. 41: 407-431
35. Iwai, M., Maoka, T., Ikeuchi, M., & Takaichi, S. (2008) 2,2'-β-Hydroxylase (CrtG) is involved in carotenogenesis of both nostoxanthin and 2-hydroxymyxol 2'-fucoside in Thermosynechococcus elongatus strain BP-1. Plant Cell Physiol. 49: 1678-1687
36. Jordan, P., Fromme, P., Witt, H. T., Klukas, O., Saenge, W., & Krauß, N. (2001) Threedimensional structure of cyanobacterial photosystem I at 2.5 Å resolution. Nature. 411: 909-917
37. Kamiya, N., & Shen, J.-R. (2003) Crystal structure of oxygen-evolving photosystem II from Thermosynechococcus vulcanus at 3.7-Å resolution. Proc. Natl. Acad. Sci. USA. 100: 98-103
38. Kern, J., Loll, B., Lüneberg, C., DiFiore, D., Biesiadka, J., Irrgang K.-D., & Zouni, A. (2005) Purification, characterisation and crystallisation of photosystem II from Thermosynechococcus elongatus cultivated in a new type of photobioreactor. Biochim. Biophys. Acta. 1706: 147-157
39. Krubasik, P., & Sandmann, G. (2000) Molecular evolution of lycopene cyclases involved in the formation of carotenoids with ionone end groups. Biochem. Soc. Trans. 28: 806-810
40. Lagarde, D., & Vermaas, W. (1999) The zeaxanthin biosynthesis enzyme β-carotene hydroxylase is involved in myxoxanthophyll synthesis in Synechocystis sp. PCC 6803. FEBS Lett. 454: 247-251
41. Liang, C.-W., Zhang, X.-W., Tian, L., & Qin, S. (2008) functional characterization of sll0659 from Synechocustis sp. PCC 6803. Ind. J. Biochem. Biophys. 45: 275-277
42. Lichtenthaler, H. K. (1999) The 1-deoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 50: 47-65
43. Linden, H., Vioque, A., & Sandmann, G. (1993) Isolation of a carotenoid biosynthesis gene coding for ζ-carotene desaturase from Anabaena PCC 7120 by heterologous complementation. FEMS Microbiol. Lett. 106: 99-104
44. Linden, H., Misawa, N., Saito, T., & Sandmann, G. (1994) A novel carotenoid biosynthesis gene coding for ζ-carotene desaturase: functional expression, sequence and phylogenetic origin. Plant Mol. Biol. 24: 369-379
45. Makino, T., Harada, H., Ikenaga, H., Matsuda, S., Takaichi, S., Shindo, K., Sandmann, G., Ogata, T., & Misawa, N. (2008) Characterization of cyanobacterial carotenoid ketolase CrtW and hydroxylase CrtR by complementation analysis in Escherichia coli. Plant Cell Physiol. 50: 1867-1878
46. Maresca, J. A., Frigaard, N.-U., & Bryant, D. A. (2005) Identification of a novel class of lycopene cyclases in photosynthetic bacteria. In: Photosynthesis: Fundamental Aspects to Global Perspectives, pp. 884-886, van der Est, A. & Bruce, D. (eds.), Allen Press, Canada
47. Maresca, J. A., Graham, J. E., Wu, M., Eisen, J. A., & Bryant, D. A. (2007) Identification of a forth family of lycopene cyclases in photosynthetic bacteria. Proc. Natl. Acad. Sci. USA. 104: 11784-11789
48. Maresca, J. A., Graham, J. E., & Bryant, D. A. (2008) The biochemical basis for structural diversity in the carotenoids of chlorophototrophic bacteria. Photosynth. Res. 97: 121-140
49. Martínez-Férez, I. M., & Vioque, A. (1992) Nucleotide sequence of the phytoene desaturase gene from Synechocystis sp. PCC 6803 and characterization of a new mutation which confers resistance to the herbicide norflurazon. Plant Mol. Biol. 18: 981-983
50. Martínez-Férez, I., Fernández-González, B., Sandmann, G., & Vioque, A. (1994) Cloning and expression in Escherichia coli of the gene coding for phytoene synthase from the cyanobacterium Synechocystis sp. PCC6803. Biochim. Biophys. Acta. 1218: 145-152
51. Masamoto, K., Misawa, N., Kaneko, T., Kikuno, R., & Toh, H. (1998) β-Carotene hydroxylase gene from the cyanobacterium Synechocystis sp. PCC6803. Plant Cell Physiol. 39: 560-564
52. Masamoto, K., Wada, H., Kaneko, T., & Takaichi, S. (2001) Identification of a gene required for cis-to-trans carotene isomerization in carotenogenesis of the cyanobacterium Synechocystis sp. PCC 6803. Plant Cell Physiol. 42: 1398-1402
53. Mochimaru, M., Masukawa, H., & Takaichi, S. (2005) The cyanobacterium Anabaena sp. PCC 7120 has two distinct β-carotene ketolases: CrtO for echinenone and CrtW for ketomyxol synthesis. FEBS Lett. 579: 6111-6114
54. Mochimaru, M., Masukawa, H., Maoka, T., Mohamed, H. E., Vermaas, W. F. J., & Takaichi, S. (2008) Substrate specificities and availability of fucosyltransferase and β-carotene hydroxylase for myxol 2'-fucoside synthesis in Anabaena sp. strain PCC 7120 compared with Synechocystis sp. strain PCC 6803. J. Bacteriol. 190: 6726-6733
55. Mohamed, H. E., & Vermaas, W. (2004) Slr1293 in Synechocystis sp. strain PCC 6803 is the C-3',4' desaturase (CrtD) involved in myxoxanthophyll biosynthesis. J. Bacteriol. 186: 5621-5628
56. Mohamed, H. E., & Vermaas, W. F. J. (2006) Sll0254 (CrtLdiox) is a bifunctional lycopene cyclase/dioxygenase in cyanobacteria producing myxoxanthophyll. J. Bacteriol. 188: 3337-3344
57. Mohamed, H. E., van de Meene, A. M. L., Roberson, R. W., & Vermaas, W. F. J. (2005) Myxoxanthophyll is required for normal cell wall structure and thylakoid organization in the cyanobacterium Synechocystis sp. strain PCC 6803. J. Bacteriol. 187: 6883-6892
58. Niggli, U. A., & Pfander, H. (1999) Carotenoid glycosides and glycosyl esters. In: Naturally Occurring Glycosides, pp. 125-145, Ikan R. (ed.), John Wiley & Sons, Chichester
59. Nishida, Y., Adachi, K., Kasai, H., Shizuri, Y., Shindo, K., Sawabe, A., Komemushi, S., Miki, W., & Misawa, N. (2005) Elucidation of a carotenoid biosynthesis gene cluster encoding a novel enzyme, 2,2'-β-hydroxylase, from Brevundimonas sp. strain SD212 and combinatorial biosynthesis of new or rare xanthophylls. Appl. Environ. Microbiol. 71: 4286-4296
60. Ohto, C., Ishida, C., Nakane, H., Muramatsu, M., Nishino, T., & Obata, S. (1999) A thermophilic cyanobacterium Synechococcus elongatus has three different Class I prenyltransferase genes. Plant Mol. Boil. 40: 307-321
61. Olaizola, M., & Duerr, E. O. (1990) Effects of light intensity and quality on the growth rate and photosynthetic pigment content of Spirulina platensis. J. Appl. Phycol. 2: 97-104
62. Omata, T., & Murata, N. (1984) Isolation and characterisation of three types of membranes from the cyanobacterium (blue-green alga) Synechocystis PCC 6714. Arch. Microbiol. 139: 113-116
63. Rählert, N., Fraser, P. D., & Sandmann, G. (2009) A crtA-related gene from Flavobacterium P99-3 encodes a novel carotenoid 2-hydroxylase involved in myxol biosynthesis. FEBS Lett. 583: 1605-1610
64. Ramos, A., Coesel, S., Marques, A., Rodrigues, M., Baumgartner, A., Noronha, J., Rauter, A., Brenig, B., & Varela, J. (2008) Isolation and characterization of a stress-inducible Dunaliella salina Lcy-β gene encoding a functional lycopene β-cyclase. Appl. Microbiol. Biotechnol. 79: 819-828
65. Rohmer, M. (1999) The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants. Nat. Prod. Rep. 16: 565-574
66. Rønneberg, H., Andrewes A. G., Borch, G., Berger, R., & Liaaen-Jensen, S. (1985) CD correlation of C-2' substituted monocyclic carotenoids. Phytochemistry. 24: 309-319
67. Sakamoto, T., Higashi, S., Wada, H., Murata, N., & Bryant, D. A. (1997) Low-temperatureinduced desaturation of fatty acids and expression of desaturase genes in the cyanobacterium Synechococcus sp. PCC 700. FEMS Microbiol. Lett. 152: 313-320
68. Sandmann, G. (1994) Carotenoid biosynthesis in microorganisms and plants. Eur. J. Biochem. 223: 7-24
69. Sandmann, G. (2001) Carotenoid biosynthesis and biotechnological application. Arch. Biochem. Biophys. 385: 4-12
70. Sandmann, G. (2002) Molecular evolution of carotenoid biosynthesis from bacteria to plants. Physiol. Plant. 116: 431-440
71. Schneider, C., Böger, P., & Sandmann, G. (1997) Phytoene desaturase: heterologous expression in an active state, purification, and biochemical properties. Protein Expr. Purif. 10: 175-179
72. Shindo, K., Kikuta, K., Suzuki, A., Katsuta, A., Kasai, H., Yasumoto-Hirose, M., Matuo, Y., Misawa, N., & Takaichi, S. (2007) Rare carotenoids, (3R)-saproxanthin and (3R,2'S)-myxol, isolated from novel marine bacteria (Flavobacteriaceae) and their antioxidative activities. Appl. Microbiol. Biotechnol. 74: 1350-1357
73. Steiger, S., & Sandmann, G. (2004) Cloning of two carotenoid ketolase genes from Nostoc punctiforme for the heterogous production of canthaxanthin and astaxanthin. Biotechnol. Lett. 26: 813-817
74. Steiger, S., Schäfer, L., & Sandmann G. (1999) High-light-dependent upregulation of carotenoids and their antioxidative properties in the cyanobacteirum Synechocystis PCC 6803. J. Photochem. Photobiol. B: Biol. 52: 14-18
75. Steiger, S., Jackisch, Y., & Sandmann, G. (2005) Carotenoid biosynthesis in Gloeobacter violaceus PCC4721 involves a single crtI-type phytoene desaturase instead of typical cyanobacterial enzymes. Arch. Microbiol. 184: 207-214
76. Stickforth, P., Steiger, S., Hess, W. R., & Sandmann G. (2003) A novel type of lycopene ε-cyclase in the marine cyanobacterium Prochlorococcus marinus MED4. Arch. Microbiol. 179: 409-415
77. Stransky, H., & Hager, A. (1970) The carotenoid pattern and the occurrence of the light induced xanthophyll cycle in various classes of algae. IV. Caynophyceae and rhodophyceae. Arch. Mikrobiol. 72: 84-96
78. Takaichi, S. (1999) Carotenoids and carotenogenesis in anoxygenic photosynthetic bacteria. In: The Photochemistry of Carotenoids, pp. 39-69, Frank, H. A., Young, A. J., Britton, G., & Cogdell, R. J. (eds.), Kluwer Academic Publishers, Dordrecht
79. Takaichi, S. (2009) Distribution and biosynthesis of carotenoids. In: The Purple Phototrophic Bacteria, pp. 97-117, Hunter, C. N., Daldal, F., Thurnauer, M. C., & Beatty, J. T. (eds.), Springer, Dordrecht
80. Takaichi, S. & Mimuro, M. (1998) Distribution and geometric isomerism of neoxanthin in oxygenic phototrophs: 9'-cis, a sole molecular form. Plant Cell Physiol. 39: 968-977
81. Takaichi, S., & Mochimaru, M. (2007) Carotenoids and carotenogenesis in cyanobacteria: unique ketocarotenoids and carotenoid glycosides. Cell. Mol. Life Sci. 64: 2607-2619
82. Takaichi, S., Wang, Z.-Y., Umetsu, M., Nozawa, T., Shimada, K., & Madigan, M. T. (1997) New carotenoids from the thermophilic green sulfur bacterium Chlorobium tepidum: 1',2'-dihydro-γ-carotene, 1',2'-dihydrochlorobactene, and OH-chlorobactene glucoside ester, and the carotenoid composition of different strains. Arch. Microbiol. 168: 270-276
83. Takaichi, S., Maoka, T., & Masamoto K. (2001) Myxoxanthophyll in Synechocystis sp. PCC 6803 is myxol 2'-dimethyl-fucoside, (3R,2'S)-myxol 2'-(2,4-di-O-methyl-α-L-fucoside), not rhamnoside. Plant Cell Physiol. 42: 756-762
84. Takaichi, S., Mochimaru, M., Maoka, T., & Katoh, H. (2005) Myxol and 4-ketomyxol 2'-fucosides, not rhamnosides, from Anabaena sp. PCC 7120 and Nostoc punctiforme PCC 73102, and proposal for the biosynthetic pathway of carotenoids. Plant Cell Physiol. 46: 497-504
85. Takaichi, S., Mochimaru, M., & Maoka, T. (2006) Presence of free myxol and 4-hydroxymyxol and absence of myxol glycosides in Anabaena variabilis ATCC 29413, and proposal of a biosynthetic pathway of carotenoids. Plant Cell Physiol. 47: 211-216
86. Tao, L., & Cheng, Q. (2004) Novel β-carotene ketolases from non-photosynthetic bacteria for canthaxanthin synthesis. Mol. Gen. Genomics. 272, 530-537
87. Tao, L., Rouvière, P. E., & Cheng, Q. (2006) A carotenoid synthesis gene cluster from a nonmarine Brevundimonas that synthesizes hydroxylated astaxanthin. Gene 379: 101-108
88. Teramoto, M., Rählert, N., Misawa, N., & Sandmann, G. (2004) 1-Hydroxy monocyclic carotenoid 3,4-dehydrogenase from a marine bacterium that produces myxol. FEBS Lett. 570: 184-188
89. Tsuchiya, T., Takaichi, S., Misawa, N., Maoka, T., Miyashita, H., & Mimuro, M. (2005) The cyanobacterium Gloeobacter violaceus PCC 7421 uses bacterial-type phytoene desaturase in carotenoid biosynthesis. FEBS Lett. 579: 2125-2129
90. Yokoyama, A., & Miki, W. (1995) Isolation of myxol from a marine bacterium Flavobacterium sp. associated with a marine sponge. Fish. Sci. 61: 684-686