The biochemical basis for structural diversity in the carotenoids of chlorophototrophic bacteria

Photosynthesis Research

Volumn 97, Issue 2, 2008, Pages 121-140

  Maresca, Julia A ^a,b   Graham, Joel E ^a   Bryant, Donald A ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b Massachusetts Institute of Technology Cambridge   (United States)

Author keywords

Carotenogenesis; Carotenoids; Cyanobacteria; Green sulfur bacteria; Lycopene cyclase; Photosynthesis

Indexed keywords

CAROTENOID;

BACTERIUM; BIOCHEMISTRY; CHEMISTRY; CHLOROPLAST; METABOLISM; PHOTOCHEMISTRY; REVIEW; STEREOISOMERISM;

BACTERIA; BIOCHEMISTRY; CAROTENOIDS; CHLOROPLASTS; PHOTOCHEMISTRY; STEREOISOMERISM;

BACTERIA (MICROORGANISMS); CHLOROBI; CYANOBACTERIA;

EID: 48349136893     PISSN: 01668595     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11120-008-9312-3     Document Type: Review

References (177)

1. T Aakermann OM Skulberg S Liaaen-Jensen 1992 Carotenoids of blue-green algae. 12. A comparison of the carotenoids of the strains of Oscillatoria and Spirulina (cyanobacteria) Biochem Syst Ecol 20 761 769
2. M Albrecht H Linden G Sandmann 1996 Biochemical characterization of purified ζ-carotene desaturase from Anabaena PCC 7120 after expression in Escherichia coli Eur J Biochem 236 115 120
3. M Albrecht A Ruther G Sandmann 1997 Purification and biochemical characterization of a hydroxyneurosporene desaturase involved in the biosynthetic pathway of the carotenoid spheroidene in Rhodobacter sphaeroides J Bacteriol 179 7462 7467
4. SF Altschul TL Madden AA Schäffer J Zhang Z Zhang W Miller DJ Lipman 1997 Gapped BLAST and PSI-BLAST: a new generation of protein database search programs Nucl Acids Res 25 3389 3402
5. AG Andrews S Liaaen-Jensen 1972 Carotenoids of Thiorhodaceae 9. Structural elucidation of five minor carotenoids from Thiothece gelatinosa Acta Chem Scand 26 2194 2204
6. GA Armstrong 1997 Genetics of eubacterial carotenoid biosynthesis: a colorful tale Annu Rev Microbiol 51 629 659
7. GA Armstrong JE Hearst 1996 Genetics and molecular biology of carotenoid biosynthesis FASEB J 10 228 237
8. GA Armstrong A Schmidt G Sanfmann JE Hearst 1990 Genetic and biochemical characterization of carotenoid biosynthesis mutants of Rhodobacter capsulatus J Biol Chem 265 8329 8338
9. ME Auldridge DR McCarty DE Klee 2006 Plant carotenoid cleavage oxygenases and their apocarotenoid products Curr Opin Plant Biol 9 315 321
10. SP Balashov ES Imasheva VA Boichenko J Anton JM Wang JK Lanyi 2005 Xanthorhodopsin: a proton pump with a light-harvesting carotenoid antenna Science 309 2061 2064
11. SP Balashov ES Imasheva JK Lanyi 2006 Induced chirality of the light-harvesting carotenoid salinixanthin and its interaction with the retinal of xanthorhodopsin Biochemistry 45 10998 11004
12. GE Bartley PA Scolnik P Beyer 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
13. JA Bautista F Rappaport M Guergova-Kuras RO Cohen JG Golbeck JY Wang D Beal BA Diner 2005 Biochemical and biophysical characterisation of photosystem I from phytoene desaturase and ζ-carotene desaturase deletion mutants of Synechocystis sp. PCC 6803 J Biol Chem 280 20030 20041
14. O Béjà L Aravind EV Koonin MT Suzuki A Hadd LP Nguyen S Jovanovich CM Gates RA Feldman JL Spudich EN Spudich EF DeLong 2000 Bacterial rhodopsin: evidence for a new type of phototrophy in the sea Science 289 1902 1906
15. GE Bialek-Bylka R Fujii CH Chen H Oh-oka A Kamiesu K Satoh H Koike Y Koyama 1998 15-cis-carotenoids found in the reaction center of a green sulfur bacterium Chlorobium tepidum and in the Photosystem I reaction center of a cyanobacterium Synechococcus vulcanus Photosynth Res 58 135 142
16. 6 f complex Biochim Biophys Acta 1506 55 66
17. Y Boucher WF Doolittle 2000 The role of lateral gene transfer in the evolution of isoprenoid biosynthesis pathways Mol Microbiol 37 703 716
18. P Bramley G Sandmann 1985 In vitro and in vivo biosynthesis of xanthophylls by the cyanobacterium Aphanocapsa Phytochemistry 24 2919 2922
19. J Breitenbach G Sandmann 2005 ζ-carotene cis-isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene Planta 220 785 793
20. J Breitenbach B Fernandez-Gonzalez A Vioque G Sandmann 1998 A higher-plant type ζ-carotene desaturase in the cyanobacterium Synechocystis sp. PCC 6803 Plant Mol Biol 36 725 732
21. J Breitenbach A Vioque G Sandmann 2001 Gene sll0033 from Synechocystis 6803 encodes a carotene isomerase involved in the biosynthesis of all-E lycopene Z Naturforsch 56 915 17
22. G Britton RK Singh TW Goodwin A Ben-Aziz 1975 The carotenoids of Rhodomicrobium vannielii (Rhodospirillaceae) and the effect of diphenylamine on the carotenoid composition Phytochemistry 14 2427 2433
23. Britton G, Liaaen-Jensen S, Pfander H (2004) Carotenoids handbook. Birkhauser, Boston, MA
24. DA Bryant N-U Frigaard 2006 Prokaryotic photosynthesis and phototrophy illuminated Trends Microbiol 14 488 496
25. P Caumette R Baulaigue R Matheron 1991 Thiocapsa halophila sp. nov., a novel halophilic phototrophic purple sulfur bacterium Arch Microbiol 155 170 176
26. P Caumette R Guyoneaud JF Imhoff J Suling V Gorenko 2004 Thiocapsa marina sp nov., a novel, okenone-containing, purple sulfur bacterium isolated from brackish coastal and marine environments Int J Syst Evol Microbiol 54 1031 1036
27. D Chamovitz N Misawa G Sandmann J Hirschberg 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
28. Q Cheng 2006 Structural diversity and functional novelty of new carotenoid biosynthesis genes J Ind Microbiol Biotechnol 33 552 559
29. Cogdell RJ (1988) The functions of pigments in chloroplasts. In: Goodwin TW (ed) Plant pigments. Academic Press, London, pp 222-224
30. FX Cunningham Jr E Gantt 2001 One ring or two? Determination of ring number in carotenoids by lycopene epsilon-cyclases Proc Nat Acad Sci USA 98 2905 2910
31. FX Cunningham Jr Z Sun D Chamovitz J Hirschberg E Gantt 1994 Molecular structure and enzymatic function of lycopene cyclase from the cyanobacterium Synechococcus sp. strain PCC7942 Plant Cell 6 1107 1121
32. BH Davies 1970 A novel sequence for phytoene dehydrogenation in Rhodospirillum rubrum Biochem J 116 93 99
33. JR de la Torre LM Christianson O Béjà MT Suzuki DM Karl J Heidelberg EF DeLong 2003 Proteorhodopsin genes are distributed among divergent marine bacterial taxa Proc Natl Acad Sci USA 100 12830 12835
34. VS Dubey R Bhalla R Luthra 2003 An overview of the non-mevalonate pathway for terpenoid biosynthesis in plants J Biosci 28 637 646
35. JA Eisen KE Nelson IT Paulsen JF Heidelberg M Wu RJ Dodson R Deboy ML Gwinn WC Nelon DH Haft EK Hickey JD Peterson AS Durkin JL Kolonay F Yang I Holt LA Umayam T Mason M Brenner TP Shea D Parksey WC Nierman TV Feldblyum CL Hansen MB Craven D Radune J Vamathevan H Khouri O White TM Gruber KA Ketchum JC Venter H Tettelin DA Bryant CM Fraser 2002 The complete genome sequence of Chlorobium tepidum TLS, a photosynthetic, anaerobic, green-sulfur bacterium Proc Natl Acad Sci USA 99 9509 9514
36. W Eisenreich A Bacher D Arigoni F Rohdich 2004 Biosynthesis of isoprenoids via the non-mevalonate pathway Cell Mol Life Sci 61 1401 1426
37. B Fernandez-Gonzales G Sandmann A Vioque 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
38. HA Frank GW Brudvig 2004 Redox functions of carotenoids in photosynthesis Biochemistry 43 8607 8615
39. PD Fraser N Misawa H Linden S Yamano K Kobayashi G Sandmann 1992 Expression in Esherichia coli, purification, and reactivation of the recombinant Erwinia uredovora phytoene desaturase J Biol Chem 267 19891 19895
40. PD Fraser H Linden G Sandmann 1993 Purification and reactivation of recombinant Synechococcus phytoene desaturase from an overexpressing strain of Escherichia coli Biochem J 291 687 692
41. NJ Fraser H Hashimoto R Cogdell 2002 Carotenoids and bacterial photosynthesis: the story so far.... Photosynth Res 70 249 256
42. N-U Frigaard JA Maresca CE Yunker AD Jones DA Bryant 2004 Genetic manipulation of carotenoid biosynthesis in the green sulfur bacterium Chlorobium tepidum J Bacteriol 186 5210 5220
43. P Fromme P Jordan N Krauss 2001 Structure of photosystem I Biochim Biophys Acta 1507 5 31
44. Garcia Costas AM, Graham JE, Bryant DA (2008) Ketocarotenoids in chlorosomes of Candidatus Chloracidobacterium thermophilum. In: Allen JF, Gantt E, Golbeck JH, Osmond B (eds) Energy from the sun. Springer, Dordrecht, The Netherlands, pp 1167-1170
45. G Garcia-Asua HP Lang RJ Cogdell CN Hunter 1998 Carotenoid diversity: a modular role for the phytoene desaturase step Trends Plant Sci 3 445 449
46. G Garcia-Asua RJ Cogdell CN Hunter 2002 Functional assembly of the foreign carotenoid lycopene into the photosynthetic apparatus of Rhodobacter sphaeroides, achieved by replacement of the native 3-step phytoene desaturase with its 4-step counterpart from Erwinia herbicola Mol Microbiol 44 233 244
47. F Gich RL Airs M Danielsen BJ Keely CA Abella J Garcia-Gil M Miller CM Borrego 2003 Characterization of the chlorosome antenna of the filamentous anoxygenic phototrophic bacterium Chloronema sp. strain UdG9001 Arch Microbiol 180 417 426
48. SJ Giovannoni L Bibbs JC Cho MD Stapels R Desiderio KL Vergin MS Rappé S Laney LJ Wilhelm HJ Tripp EJ Mathur DF Barofsky 2005 Proteorhodopsin in the ubiquitous marine bacterium SAR11 Nature 438 82 85
49. E Giraud L Hannibal J Fardoux M Jaubert P Jourand B Dreyfus JN Sturgis A Vermeglio 2004 Two distinct crt gene clusters for two different functional classes of carotenoid in Bradyrhizobium J Biol Chem 279 15076 15083
50. G Giuliano D Pollock PA Scolnik 1986 The gene crtI mediates the conversion of phytoene into colored carotenoids in Rhodopseudomonas capsulata J Biol Chem 261 12925 12929
51. R Goeriche D Repeta 1992 The pigments of Prochlorococcus marinus: the presence of divinyl chlorophyll a and b in a marine prokaryote Limnol Oceanogr 37 425 433
52. A Gomez Maqueo Chew DA Bryant 2007 Chlorophyll biosynthesis in bacteria: the origins of structural and functional diversity Annu Rev Microbiol 61 113 129
53. L Gómez-Consarnau JM González M Coll-Lladó P Gourdon T Pascher R Neutze C Pedrós-Alió J Pinhassi 2007 Light stimulates growth of proteorhodopsin-containing marine Flavobacteria Nature 445 210 213
54. Graham JE (2008) Carotenoid biosynthesis in Synechococcus sp. PCC 7002: identification of genes, enzymes and carotenoids. Ph D thesis, The Pennsylvania State University
55. 40 xanthophyll is a major carotenoid in the cyanobacterium Synechococcus sp. PCC 7002. J Nat Prod, submitted for publication
56. DE Gregonis HC Rilling 1974 The Stereochemistry of trans-phytoene synthesis. Some observations on lycopersene as a carotenoid precursor and a mechanism for the synthesis of trans lycopene Biochemistry 13 1538 1542
57. S Hanada A Hiraishi K Shimada K Matsuura 1995 Chloroflexus aggregans sp. nov., a filamentous phototrophic bacterium which forms dense cell aggregates by active gliding movement Int J Syst Bacteriol 45 676 681
58. S Hanada S Takaichi K Matsuura K Nakamura 2002 Roseiflexus castenholzii gen. nov., sp. nov., a thermophilic, filamentous photosynthetic bacterium that lacks chlorosomes Int J Syst Evol Microbiol 52 187 193
59. J Harada KVP Nagashima S Takaichi N Misawa K Matsuura K Shimada 2001 Phytoene desaturase, CrtI, of the purple photosynthetic bacterium, Rubrivivax gelatinosus, produces both neurosporene and lycopene Plant Cell Physiol 42 1112 1118
60. A Hausmann G Sandmann 2000 A single five-step desaturase is involved in the carotenoid biosynthesis pathway to beta-carotene and torulene in Neurospora crassa Fungal Genet Biol 30 147 153
61. H Hemmi S Ikejiri T Nakayama T Nishino 2003 Fusion-type lycopene β-cyclase from a thermoacidophilic archaeon Sulfolobus solfataricus Biochem Biophys Res Comm 305 586 591
62. K Hesse E Dittmann T Borner 2001 Consequences of impaired microcystin production for light-dependent growth and pigmentation of Microcystis aeruginosa PCC 7806 FEMS Microbiol Ecol 37 39 43
63. H Hirabiayashi T Ishii S Takaichi K Inoue K Uehara 2004 The role of carotenoids in the brown-colored sulfur bacterium Chlorobium phaeobacteroides Photochem Photobiol 79 280 285
64. JG Holt RA Lewin 1968 Herpetosiphon aurantiacus gen. et sp. n., a new filamentous gliding organism J Bacteriol 95 2407 2408
65. BS Hundle DA O'Brien M Alberti P Meyer JA Hearst 1992 Functional expression of a zeaxanthin glucosyltransferase from Erwinia herbicola and a proposed uridine diphosphate binding site Proc Nat Acad Sci USA 89 9321 9325
66. WN Hunter 2007 The non-mevalonate pathway of isoprenoid precursor biosynthesis J Biol Chem 282 21573 21577
67. T Isaacson G Ronen D Zamir J Hirschberg 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
68. P Jordan P Fromme HT Witt O Klukas W Sanger N Krauss 2001 Three-dimensional structure of cyanobacterial photosystem I at 2.5 Å resolution Nature 411 909 911
69. DP Kloer S Ruch S Al-Babili P Beyer GE Schulz 2005 The structure of a retinal-forming carotenoid oxygenase Science 308 267 269
70. AT Kovács G Rákhely KL Kovács 2003 Genes involved in the biosynthesis of the photosynthetic pigments in the purple sulfur photosynthetic bacterium Thiocapsa roseopersicina Appl Environ Microbiol 69 3093 3102
71. P Krubasik G Sandmann 2000 A carotenogenic gene cluster from Brevibacterium linens with novel lycopene cyclase genes involved in the synthesis of aromatic carotenoids Mol Gen Genet 263 423 432
72. P Krubasik G Sandmann 2000 Molecular evolution of lycopene cyclases involved in the formation of carotenoids with ionone end groups Biochem Soc Trans 28 806 810
73. BP Krueger GD Scholes R Jimenez GR Fleming 1998 Electronic excitation transfer from carotenoid to bacteriochlorophyll in the purple bacterium Rhodopseudomonas acidophila J Phys Chem B 102 2284 2292
74. H Krugel P Krubasik K Weber HP Saluz G Sandmann 1999 Functional analysis of genes from Streptomyces griseus involved in the synthesis of isorenieratene, a carotenoid with aromatic end groups, revealed a novel type of carotenoid desaturase Biochim Biophys Acta 1439 57 64
75. PA Kumar TNR Srinivas C Sasikala CV Ramana 2007 Halochromatium roseum sp. nov., a non-motile phototrophic gammaproteobacterium with gas vesicles, and emended description of the genus Halochromatium Int J Syst Evol Microbiol 57 2110 2113
76. SC Kushwaha M Kates 1979 Effect of nicotine on biosynthesis of C50 carotenoids in Halobacterium cutirubrum Can J Biochem 54 824 829
77. T Kuzuyama 2002 Mevalonate and nonmevalonate pathways for the biosynthesis of isoprene units Biosci Biotechnol Biochem 66 1619 1627
78. D Lagarde WFJ Vermaas 1999 The zeaxanthin biosynthesis enzyme β-carotene hydroxylase is involved in myxoxanthophyll synthesis in Synechocystis sp. PCC 6803 FEBS Lett 454 247 245
79. M Lakatos W Bilger B Budel 2001 Carotenoid composition of terrestrial Cyanobacteria: response to natural light conditions in open rock habitats in Venezuela Eur J Phycol 36 367 375
80. HP Lang RJ Cogdell S Takaichi CN Hunter 1995 Complete DNA sequence, specific Tn5 insertion map, and gene assignment of the carotenoid biosynthesis pathway of Rhodobacter sphaeroides J Bacteriol 177 2064 2073
81. PC Lee BN Mijts C Schmidt-Dannert 2004 Investigation of factors influencing production of the monocyclic carotenoid torulene in metabolically engineered Escherichia coli Appl Microbiol Biotechnol 65 538 546
82. LS Leutwiler DJ Chapman 1978 Biosynthesis of carotenoids in Rhodomicrobium vannielii FEBS Lett 89 248 252
83. F Li C Murillo ET Wurtzel 2007 Maize y9 encodes a product essential for 15-cis-ζ-carotene isomerization Plant Physiol 144 1181 1189
84. S Liaaen-Jensen 1965 Bacterial carotenoids. XVIII. Aryl carotenoids from Phaeobium Acta Chemica Scand 19 1025 1030
85. C Liang F Zhao W Wei Z Wen S Qin 2006 Carotenoid biosynthesis in cyanobacteria: structural and evolutionary scenarios based on comparative genomics Int J Biol Sci 2 197 207
86. H Linden N Misawa D Chamovitz I Pecker J Hirschberg G Sandmann 1991 Functional complementation in Escherichia coli of different phytoene desaturase genes and analysis of accumulated carotenes Z Naturforsch 46 1045 1051
87. Y Liu H Wang H-C Ye G-F Li 2005 Advances in the plant isoprenoid biosynthesis pathway and its metabolic engineering J Integ Plant Biol 47 769 782
88. CI Liu GY Liu Y Song F Yin ME Hensler WY Jeng V Nizet AH Wang E Oldfield 2008 A cholesterol biosynthesis inhibitor blocks Staphylococcus aureus virulence Science 319 1391 1394
89. RH Lozier RA Bogomolni W Stoeckenius 1975 Bacteriorhodopsin: light-driven proton pump in Halobacterium halobium Biophys J 15 955 962
90. 2 state in a photosynthetic light-harvesting complex Biophys J 80 923 930
91. EK Marasco K Vay C Schmidt-Dannert 2006 Identification of carotenoid cleavage dioxygenases from Nostoc sp. PCC 7120 with different cleavage activities J Biol Chem 281 31583 31593
92. Maresca JA (2007) The genetic basis for pigment variation among green sulfur bacteria. Ph D thesis, The Pennsylvania State University
93. JA Maresca DA Bryant 2006 Two genes encoding new carotenoid-modifying enzymes in the green sulfur bacterium Chlorobium tepidum J Bacteriol 188 6217 6223
94. JA Maresca JE Graham M Wu J Eisen DA Bryant 2007 Identification of a fourth type of carotenoid cyclase in photosynthetic organisms Proc Natl Acad Sci USA 104 11784 11789
95. A Martinez AS Bradley JR Waldbauer RE Summons EF Delong 2007 Proteorhodopsin photosystem gene expression enables photophosphorylation in a heterologous host Proc Nat Acad Sci USA 104 5590 5595
96. I Martinez-Ferez B Fernandez-Gonzalez G Sandmann A Vioque 1994 Cloning and expression in Escherichia coli the gene coding for phytoene synthase from the cyanobacterium Synechocystis sp. PCC 6803 Biochim Biophys Acta 1218 145 152
97. K Masamoto N Misawa T Kaneko R Kikuno H Toh 1998 β-carotene hydroxylase gene from the cyanobacterium Synechocystis sp. PCC 6803 Plant Cell Physiol 39 560 564
98. K Masamoto H Wada T Kaneko S Takaichi 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
99. SK Math JE Hearst CD Poulter 1992 The crtE gene in Erwinia herbicola encodes geranylgeranyl diphosphate synthase Proc Nat Acad Sci USA 89 6761 6764
100. H Matsumura H Takeyama E Kusakabe JG Burgess T Matsunanga 1997 Cloning, sequencing, and expressing the carotenoid biosynthesis genes, lycopene cyclase and phytoene desaturase, from the aerobic photosynthetic bacterium Erythrobacter longus sp. strain Och101 in Escherichia coli Gene 189 169 174
101. B Maudinas R Herber J Villoutreix 1974 Occurrence of tran-phyotene in microorganisms grown in the absence of carotenogenesis inhibitors Biochim Biophys Acta 348 357 360
102. J McCarren EF DeLong 2007 Proteorhodopsin photosystem gene clusters exhibit co-evolutionary trends and shared ancestry among diverse marine microbial phyla Environ Microbiol 9 846 858
103. BN Mijts PC Lee C Schmidt-Dannert 2004 Engineering carotenoid biosynthetic pathways Meth Enzymol 388 315 329
104. M Mimuro T Katoh 1991 Carotenoids in photosynthesis: absorption, transfer and dissipation of light energy Pure Appl Chem 63 123 130
105. N Misawa M Nakagawa K Kobayashi S Yamano Y Izawa K Nakamura K Harashima 1990 Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli J Bacteriol 172 6704 6712
106. N Misawa S Kajiwara K Kondo A Yokoyama Y Satomi T Saito W Miki T Ohtani 1995 Canthaxanthin biosynthesis by the conversion of methylene to keto groups in the hydrocarbon β-carotene by a single gene Biochem Biophys Res Comm 209 867 876
107. E Miskiewicz AG Ivanov JP Williams MU Khan S Falk NPA Huner 2000 Photosynthetic acclimation of the filamentous cyanobacterium, Plectonema boryanum UTEX 485, to temperature and light Plant Cell Phys 41 767 775
108. M Mochimaru H Masukawa S Takaichi 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
109. HE Mohamed WFJ Vermaas 2004 Slr1293 in Synechocystis sp. strain PCC 6803 is the C-3′, 4′ desaturase (CrtD) involved in myxoxanthophyll biosynthesis J Bacteriol 186 5621 5628
110. HE Mohamed WFJ Vermaas 2006 Sll0254 (CrtL(diox)) is a bifunctional lycopene cyclase/dioxygenase in cyanobacteria producing myxoxanthophyll J Bacteriol 188 3337 3344
111. AA Moskalenko ZK Makhevna L Fiedor H Scheer 2005 Effects of carotenoid inhibition on the photosynthetic RC-LHI complex in purple sulphur bacterium Thiorhodospira sibirica Photosynth Res 86 71 80
112. H Nagae T Kakitani T Katoh M Mimuro 1993 Calculation of the excitation transfer-matrix elements between the S(2) or S(1) state of carotenoid and the S(2) or S(1) state of bacteriochlorophyll J Chem Phys 98 8012 8023
113. U Neudert IM Martinez-Ferez PD Fraser G Sandmann 1998 Expression of an active phytoene synthase from Erwinia uredovora and biochemical properties of the enzyme Biochim Biophys Acta 1392 51 58
114. Y Nishida K Adachi H Kasai Y Shizuri K Shindo A Sawabe S Komemushi W Miki N Misawa 2005 Elucidation of a carotenoid biosynthesis gene cluster encoding a novel enzyme, 2, 2′-beta-hydroxylase, from Brevundimonas sp. strain SD212 and a combinatorial biosynthesis of new or rare xanthophylls Appl Environ Microbiol 71 4286 4296
115. K Okada M Minehira X Zhu K Suzuki T Nakagawa H Matsuda M Kawamukai 1997 The ispB gene encoding octaprenyl diphosphate synthase is essential for growth of Escherichia coli J Bacteriol 179 3058 3060
116. H Park SS Kreunen AJ Cuttriss D DellaPenna BJ Pogson 2002 Identification of the carotenoid isomerase provides insight into carotenoid biosynthesis, prolamellar body formation, and photomorphogenesis Plant Cell 14 321 332
117. RF Peck C Echevarri-Erasun EA Johnson WV Ng SP Kennedy L Hood S DasSarma MP Krebs 2001 brp and blh are required for synthesis of the retinal cofactor of bacteriorhodopsin in Halobacterium salinarum J Biol Chem 276 5739 5744
118. RF Peck EA Johnson MP Krebs 2002 Identification of a lycopene beta-cyclase required for bacteriorhodopsin biogenesis in the archaeon Halobacterium salinarum J Bacteriol 184 2889 2897
119. 50-carotenoids Pure Appl Chem 66 2369 2374
120. BK Pierson SJ Giovannoni DA Stahl RW Castenholz 1985 Heliothrix oregonensis, gen. nov., sp. nov., a phototrophic filamentous gliding bacterium containing bacteriochlorophyll a Arch Microbiol 142 164 167
121. V Pinta S Ouchane M Picaud S Takaichi C Astier F Reiss-Husson 2003 Characterization of unusual hydroxy- and ketocarotenoids in Rubrivivax gelatinosus: involvement of enzyme CrtF or CrtA Arch Microbiol 179 354 362
122. J Psencik YZ Ma JB Arellano J Garcia-Gil AR Holzwarth T Gillbro 2002 Excitation energy transfer in chlorosomes of Chlorobium phaeobacteroides strain CL1401: the role of carotenoids Photosynth Res 71 5 18
123. Qureshi N, Porter JW (1981) Conversion of acetyl-coenzyme A to isopentenyl pyrophosphate. In: Porter JW, Spurgeon SL (eds) Biosynthesis of isoprenoid compounds vol 1. Wiley, New York, pp 47-94
124. 40 carotenoid biosynthetic pathways Biochim Biophys Acta 1533 164 170
125. A Raisig G Bartley P Scolnik G Sandmann 1996 Purification in an active state and properties of the 3-step phytoene desaturase from Rhodobacter capsulatus overexpressed in Escherichia coli J Biochem 119 559 564
126. C Rieder G Strauss G Fuchs D Arigoni A Bacher W Eisenreich 1998 Biosynthesis of the diterpene verrucosan-2β-ol in the phototrophic eubacterium Chloroflexus aurantiacus J Biol Chem 273 18099 18108
127. T Ritz A Damjanovic K Schulten J-P Zhang Y Koyama 2000 Efficient light harvesting through carotenoids Photosynth Res 66 125 144
128. F Rohdich A Bacher W Eisenreich 2004 Perspectives in anti-infective drug design: the late steps in the biosynthesis of the universal terpenoid precursors, isopentenyl diphosphate and dimethylallyl diphosphate Bioorg Chem 32 292 308
129. S Ruch P Beyer H Ernst S Al-Babili 2005 Retinal biosynthesis in eubacteria: in vitro characterization of a novel carotenoid oxygenase from Synechocystis sp. PCC 6803 Mol Microbiol 55 1015 1024
130. G Sabehi A Loy K-H Jung R Partha JL Spudich T Isaacson J Hirschberg M Wagner O Béjà 2005 New insights into metabolic properties of marine bacteria encoding proteorhodopsins PLoS Biol 3 1409 1417
131. G Sandmann 1991 Light-dependent switch from formation of poly-cis carotenes to all-trans carotenoids in the Scenedesmus mutant C-6D Arch Microbiol 155 229 233
132. G Sandmann N Misawa 1992 New functional assignment of the carotenogenic genes crtB and crtE with constructs of these genes from Erwinia species FEMS Microbiol Lett 90 253 258
133. S Santoyo M Herrero FJ Senorans A Cifuentes E Ibanez L Jaime 2006 Functional characterization of pressurized liquid extracts of Spirulina platensis Eur Food Res Technol 224 75 81
134. L Schafer A Vioque G Sandmann 2005 Functional in situ evaluation of photosynthesis-protecting carotenoids in mutants of the cyanobacterium Synechocystis sp. PCC 6803 J Photochem Photobiol B 78 195 201
135. M Schagerl K Donabaum 2003 Patterns of major photosynthetic pigments in freshwater algae. 1. Cyanoprokaryota, Rhodophyta, and Cryptophyta Int J Limnol 39 35 47
136. M Schagerl B Muller 2006 Acclimation of chlorophyll a and carotenoid levels to different irradiances in four freshwater cyanobacteria J Plant Phys 163 709 716
137. D Scherzinger S Ruch DP Kloer A Wilde S Al-Babili 2006 Retinal is formed from apo-carotenoids in Nostoc sp. 7120: in vitro characterization of an apo-carotenoid oxygenase Biochem J 398 361 369
138. L Schluter K Garde H Kaas 2004 Detection of the toxic cyanobacteria Nodularia spumigena by means of a 4-keto-myxoxanthophyll-like pigment in the Baltic Sea Marine Ecol Prog Series 275 69 78
139. K Schmidt 1980 A comparative study on the composition of chlorosomes (Chlorobium vesicles) and cytoplasmic membranes from Chloroflexus aurantiacus strain Ok-70-fl and Chlorobium limicola f. thiosulfatophilum strain 6230 Arch Microbiol 124 21 31
140. K Schmidt S Liaaen-Jensen 1973 Bacterial carotenoids. XLII. New keto-carotenoids from Rhodopseudomonas globiformis (Rhodospirillaceae) Acta Chem Scand 27 3040 3052
141. C Schneider P Boger G Sandmann 1997 Phytoene desaturase: heterologous expression in an active state, purification, and biochemical properties Protein Expres Purif 10 175 179
142. SH Schwartz BC Tan DA Gage JAD Zeevaart DA McCarty 1997 Specific oxidative cleavage of carotenoids by VP14 of maize Science 276 1872 1874
143. PA Scolnik MA Walker BL Marrs 1980 Biosynthesis of carotenoids derived from neurosporene in Rhodopseudomonas capsulata J Biol Chem 255 2427 2432
144. TN Sidorova ZK Makhneva NN Puchkova VM Gorlenko YE Erokhin AA Moskalenko 1998 Characteristics of the photosynthetic apparatus of the purple bacterium Thiocapsa sp. BM3 containing okenone as a major carotenoid Microbiology 67 158 164
145. JL Spudich 2006 The multitalented microbial sensory rhodopsins Trends Microbiol 14 480 487
146. JL Spudich C-S Yang K-H Jung EN Spudich 2000 Retinylidene proteins: structures and functions from archaea to humans Annu Rev Cell Dev Biol 16 365 392
147. S Steiger G Sandmann 2004 Cloning of two carotenoid ketolase genes from Nostoc punctiforme for the heterologous production of canthaxanthin and astaxanthin Biotechnol Lett 26 813 817
148. S Steiger A Astier G Sandmann 2000 Substrate specificity of the expressed carotenoid 3, 4 desaturase from Rubrivivax gelatinosus reveals the detailed reaction sequence to spheroidene and spirilloxanthin Biochem J 349 635 640
149. S Steiger S Takaichi G Sandmann 2002 Heterologous production of two unusual acyclic carotenoids, 1, 1′-dihydroxy-3, 4-didehydrolycopene and 1-hydroxy-3, 4, 3′, 4′-tetradehydrolycopene by combination of the crtC and crtD genes from Rhodobacter and Rubrivivax J Biotechnol 97 51 58
150. S Steiger Y Jackisch G Sandmann 2005 Carotenoid biosynthesis in Gloeobacter violaceus PCC4721 [sic] involves a single crtI-type phytoene desaturase instead of typical cyanobacterial enzyme Arch Microbiol 184 207 214
151. P Stickforth G Sandmann 2007 Kinetic variations determine the product pattern of phytoene desaturase from Rubrivivax gelatinosus Arch Biochem Biophys 461 235 241
152. P Stickforth S Steiger WR Hess G Sandmann 2003 A novel type of lycopene epsilon-cyclase in the marine cyanobacterium Prochlorococcus marinus MED4 Arch Microbiol 179 409 415
153. M Sumii Y Furutani SA Waschuk LS Brown H Kandori 2005 Strongly hydrogen-bonded water molecule present near the retinal chromophore of Leptosphaeria rhodopsin, the bacteriorhodopsin-like proton pump from a eukaryote Biochemistry 44 15159 15166
154. Takaichi S (1999) Carotenoids and carotenogenesis in anoxygenic photosynthetic bacteria. In: Frank HA, Young AJ, Britton G, Cogdell R (eds) Advances in photosynthesis and respiration, vol 8, The photochemistry of carotenoids. Kluwer Academic Publishers, Dordrecht, The Netherlands, pp 39-69
155. S Takaichi K Shimada 1999 Pigment composition of two pigment-protein complexes derived from anaerobically and aerobically grown Rubrivivax gelatinosus and identification of a new ketocarotenoid, 2-ketospirilloxanthin Plant Cell Phys 40 613 617
156. S Takaichi K Shimada J-I Ishidu 1990 Carotenoids from the aerobic photosynthetic bacterium, Erythrobacter longus: β-carotene and its hydroxyl derivatives Arch Microbiol 153 118 122
157. S Takaichi K Inoue M Akaike M Kobayashi H Oh-Oka MT Madigan 1997 The major carotenoid in all known species of heliobacteria is the C30 carotenoid 4, 4′ diaponeurosporene, not neurosporene Arch Microbiol 168 277 281
158. S Takaichi Z-W Wang M Umetsu T Nozawa K Shimada MT Madigan 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
159. S Takaichi T Maoka M Yamada K Matsuura Y Haikawa S Hanada 2001 Absence of carotenes and presence of a tertiary methoxy group in a carotenoid from a thermophilic filamentous photosynthetic bacterium Roseiflexus castenholzii Plant Cell Physiol 42 1355 1362
160. S Takaichi M Mochimaru T Maoka H Katoh 2005 Myxol and 4-ketomyxol 2′-fucosides, not rhamnosides, from Anabaena sp. PCC 7120 and Nostoc punctiforme sp. PCC 73102, and proposal for the biosynthetic pathway of carotenoids Plant Cell Physiol 46 497 504
161. S Takaichi M Mochimaru T Maoka 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
162. L Tao Q Cheng 2004 Novel β-carotene ketolases from non-photosynthetic bacteria for canthaxanthin biosynthesis Mol Gen Genomics 272 530 537
163. L Tao S Picataggio PE Rouviere Q Cheng 2004 Asymmetrically acting lycopene beta-cyclases (CrtLm) from non-photosynthetic bacteria Mol Genet Genomics 271 180 188
164. L Tao A Schenzle JM Odom Q Cheng 2005 Novel carotenoid oxidase involved in biosynthesis of 4, 4′-diapolycopene dialdehyde Appl Environ Microbiol 71 3294 3301
165. L Tao PE Rouviere Q Cheng 2006 A carotenoid synthesis gene cluster from a non-marine Brevundimonas that synthesizes hydroxylated astaxanthin Gene 379 101 108
166. M Teramoto S Takaichi Y Inomata H Ikenaga N Misawa 2003 Structural and functional analysis of a lycopene beta-monocyclase gene isolated from a unique marine bacterium that produces myxol FEBS Lett 545 120 126
167. LD Thornburg MT Lai JS Wishnok J Stubbe 1993 A non-heme iron protein with heme tendencies: an investigation of the substrate specificity of thymine hydroxylase Biochemistry 32 14023 14033
168. T Tsuchiya S Takaichi N Misawa T Maoka H Miyashita M Mimuro 2005 The cyanobacterium Gloeobacter violaceus PCC 7421 uses bacterial-type phytoene desaturase in carotenoid biosynthesis FEBS Lett 579 2125 2129
169. Z Varkonyi K Masamoto M Debreczeny O Zsiros B Ughy Z Gombos I Domonkos T Farkas H Wada B Szalontai 2002 Low-temperature-induced accumulation of xanthophylls and its structural consequences in the photosynthetic membranes of the cyanobacterium Cylindrospermopsis raciborskii: an FTIR spectroscopic study Proc Natl Acad Sci USA 99 2410 2415
170. M Viveiros P Krubasik G Sandmann M Houssaini-Iraqui 2000 Structural and functional analysis of the gene cluster encoding carotenoid biosynthesis in Mycobacterium aurum A+ FEMS Microbiol Lett 187 95 101
171. K Vogl J Glaeser KR Pfannes G Wanner R Overmann 2006 Chlorobium chlorochromatii sp nov., a symbiotic green sulfur bacterium isolated from the phototrophic consortium "Chlorochromatium aggregatum" Arch Microbiol 185 363 372
172. A Wehling PJ Walla 2005 Time-resolved two-photon spectroscopy of photosystem I determines hidden carotenoid dark-state dynamics J Phys Chem B 109 24510 24516
173. 6 f complex FEBS J 272 582 592
174. B Wieland C Feil E Gloria-Maercker G Thumm M Lechner J-M Bravo K Poralla F Gotz 1994 Genetic and biochemical analyses of the biosynthesis of the yellow carotenoid 4, 4′-diaponeurosporene of Staphylococcus aureus J Bacteriol 176 7719 7726
175. J Xiong K Inoue CE Bauer 1998 Tracking molecular evolution of photosynthesis by characterization of a major photosynthesis gene cluster from Heliobacillus mobilis Proc Natl Acad Sci USA 95 14851 14856
176. RW Ye KJ Stead H Yao H He 2006 Mutational and functional analysis of the β-carotene ketolase involved in the production of canthaxanthin and astaxanthin Appl Environ Microbiol 72 5829 5837
177. A Zouni HT Witt J Kern P Fromme N Krauss W Saenger P Orth 2001 Crystral structure of photosystem II from Synechococcus elongatus at 3.8 Å resolution Nature 409 739 743