Characterization of bacterial β-carotene 3,3′-hydroxylases, CrtZ, and P450 in astaxanthin biosynthetic pathway and adonirubin production by gene combination in Escherichia coli

Applied Microbiology and Biotechnology

Volumn 72, Issue 6, 2006, Pages 1238-1246

  Choi, Seon Kang ^c   Matsuda, Satoru ^a   Hoshino, Takayuki ^b   Peng, Xue ^a   Misawa, Norihiko ^a  

^a MARINE BIOTECHNOLOGY INSTITUTE   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

^c Gangneung Marine Bio Foundation   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CAROTENE HYDROXYLASE (CRTZ); COMPLEMENTATION ANALYSIS; HETEROLOGOUS HOSTS; P450 MONOOXYGENASE (CYP175A1);

BIOSYNTHESIS; BIOTECHNOLOGY; CATALYST ACTIVITY; CELL CULTURE; ESCHERICHIA COLI; GENES; PIGMENTS;

ENZYMES;

ADONIRUBIN; ASTAXANTHIN; BACTERIAL ENZYME; BACTERIAL PROTEIN; BETA CAROTENE; BETA CAROTENE 3,3' HYDROXYLASE; CANTHAXANTHIN; CAROTENOID; CYTOCHROME P450; GENE PRODUCT; PHOENICOXANTHIN; PROTEIN CRTZ; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; ZEAXANTHIN;

ANALYTICAL METHOD; BACTERIUM; ENZYME; GENE EXPRESSION; SPECTROSCOPY;

AGROBACTERIUM AURANTIACUM; ALCALIGENES; ARTICLE; BACTERIAL GENE; BACTERIOPLANKTON; BREVUNDIMONAS; CELL TRANSFORMATION; CHROMATOGRAPHY; CRTZ GENE; CYP175A1 GENE; ENZYME ANALYSIS; ENZYME MECHANISM; ERWINIA; ERWINIA UREDOVORA; ESCHERICHIA COLI; GENE EXPRESSION; GENETIC COMPLEMENTATION; GENETIC RECOMBINATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PANTOEA; PANTOEA ANANATIS; PARACOCCUS; PLASMID; PROTEIN ANALYSIS; PROTEIN PROCESSING; PROTEIN SYNTHESIS; RHIZOBIUM; SPECTROSCOPY; THERMUS THERMOPHILUS;

CAULOBACTERACEAE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; ESCHERICHIA COLI; MIXED FUNCTION OXYGENASES; PANTOEA; PARACOCCUS; RECOMBINANT PROTEINS; SPECTRUM ANALYSIS; THERMUS THERMOPHILUS; TRANSFORMATION, BACTERIAL; XANTHOPHYLLS;

AGROBACTERIUM AURANTIACUM; ALCALIGENES SP.; BACTERIA (MICROORGANISMS); BREVUNDIMONAS; ESCHERICHIA COLI; PANTOEA ANANATIS; PARACOCCUS SP.; THERMUS THERMOPHILUS;

EID: 33749872408     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-006-0426-2     Document Type: Article

References (44)

1. Altschul SF, Madden TL, Schaffer AA, Zhang J, Zhang Z, Miller W, Lipmann DJ (1997) Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res 25:3389-3402
2. Andrewes AG, Phaff HJ, Starr MP (1976) Carotenoids of Phaffia rhodozyma, a red-pigmented fermenting yeast. Phytochemistry 15:1003-1007
3. Berry A, Janssens D, Humbelin M, Jore JPM, Hoste B, Cleenwerck L, Vancanneyt M, Bretzel W, Mayer AF, Lopez-Ulibarri R, Shanmugam B, Swings J, Pasamontes L (2003) Paracoccus zeaxanthinifaciens sp. nov., a zeaxanthin-producing bacterium. Int J Syst Evol Microbiol 53:231-238
4. Blasco F, Kauffmann I, Schmid RD (2004) CYP175A1 from Thermus thermophilus HB27, the first β-carotene hydroxylase of the P450 superfamily. Appl Microbiol Biotechnol 64:671-674
5. Boussiba S, Vonshak A (1991) Astaxanthin accumulation in the green alga Haematococcus pluvialis. Plant Cell Physiol 32:1077-1082
6. Breitenbach J, Misawa N, Kajiwara S, Sandmann G (1996) Expression in Escherichia coli and properties of the carotene ketolase from Haematococcus pluvialis. FEMS Microbiol Lett 140:241-246
7. Chen BP, Park JS (2004) Carotenoid action on the immune response. J Nutr 134:257S-261S
8. Chen BP, Park JS, Wong MW, Wong TS (1999) A comparision of the anticancer activities of dietary beta-carotene, canthaxanthin and astaxanthin in mice in vivo. Anticancer Res 19:1849-1853
9. Choi SK, Nishida Y, Matsuda S, Adachi K, Kasai H, Peng X, Komemushi S, Miki W, Misawa N (2005) Characterization of β-carotene ketolases, CrtW, from marine bacteria by complementation analysis in Escherichia coli. Mar Biotechnol 7:515-522
10. Fraser PD, Miura Y, Misawa N (1997) In vitro characterization of astaxanthin biosynthetic enzymes. J Biol Chem 272:6128-6135
11. Fraser PD, Shimada H, Misawa N (1998) Enzymic confirmation of reactions involved in routes to astaxanthin formation, elucidated using a direct substrate in vitro assay. Eur J Biochem 252:229-236
12. Felsenstein J (1985) Confidence limits on phylogenies: an approach using the bootstrap. Evolution 39:783-791
13. Iwamoto T, Hosoda K, Hirano R, Kurata H, Matsumoto A, Miki W, Kamiyama M, Itakura H, Yamamoto S, Kondo K (2000) Inhibition of low-density lipoprotein oxidation by astaxanthin. J Atheroscler Thromb 7:216-222
14. Kajiwara S, Kakizono T, Saito T, Kondo K, Ohtani T, Nishio N, Nagai S, Misawa N (1995) Isolation and functional identification of a novel cDNA for astaxanthin biosynthesis from Haematococcus pluvialis, and astaxanthin synthesis in Escherichia coli. Plant Mol Biol 29:343-352
15. Kimura M (1980) A simple method for estimating evolutionary rates of base substitutions through comparative studies of nucleotide sequences. J Mol Evol 16:111-120
16. Lee PC, Schmidt-Dannert C (2002) Metabolic engineering towards biotechnological production of carotenoids in microorganisms. Appl Microbiol Biotechnol 60:1-11
17. Mann V, Harker M, Pecker I, Hirschberg J (2000) Metabolic engineering of astaxanthin production in tobacco flowers. Nat Biotechnol 18:888-889
18. 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
19. Meyers SP (1994) Developments in world aquaculture, feed formulations and role of carotenoids. Pure Appl Chem 66:1069-1076
20. Misawa N, Nakagawa M, Kobayashi K, Yamano S, Izawa Y, Nakamura K, Harashima K (1990) Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli. J Bacteriol 172:6704-6712
21. Misawa N, Satomi Y, Kondo K, Yokoyama A, Kajiwara S, Saito T, Ohtani T, Miki W (1995) Structure and functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin biosynthetic pathway proposed at the gene level. J Bacteriol 177:6575-6584
22. 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
23. 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
24. Papp T, Velayos A, Bartok T, Eslava AP, Vagvolgyi C, Iturriaga EA (2005) Heterologous expression of astaxanthin biosynthesis genes in Mucor circinelloides. Appl Microbiol Biotechnol (July 21: Epub ahead of print)
25. Ralley L, Enfissi EM, Misawa N, Schuch W, Bramley PM, Fraser PD (2004) Metabolic engineering of ketocarotenoid formation in higher plants. Plant J 39:477-486
26. Ravanello MP, Ke D, Alvarez J, Huang B, Shewmaker CK (2003) Coordinate expression of multiple bacterial carotenoid genes in canola leading to altered carotenoid production. Metab Eng 5:255-263
27. Renstrom B, Berger H, Liaaen-Jensen S (1981) Esterified, optically pure (3S, 3′S)-astaxanthin from flowers of Adonis annua. Biochem Syst Ecol 9:249-250
28. Romer S, Fraser PD, Kiano JW, Shipton CA, Misawa N, Schuch W, Bramley PM (2000) Elevation of the provitamin A content of transgenic tomato plants. Nat Biotechnol 18:666-669
29. Saitou N, Nei M (1987) The neighbor-joining method: a new method for reconstructing phylogenetic trees. Mol Biol Evol 4:406-425
30. Sambrook J, Fritsch EF, Maniatis T (1989) Molecular cloning: a laboratory manual, 2nd edn. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY
31. Shewmaker CK, Sheehy JA, Daley M, Colburn S, Ke DY (1999) Seed-specific overexpression of phytoene synthase: increase in carotenoids and other metabolic effects. Plant J 20:401-412
32. Stalberg K, Lindgren O, Ek B, Hoglund AS (2003) Synthesis of ketocarotenoids in the seed of Arabidopsis thaliana. Plant J 36:771-779
33. Tao L, Cheng Q (2004) Novel β-carotene ketolases from nonphotosynthetic bacteria for canthaxanthin synthesis. Mol Genet Genomics 272:530-537
34. Tatsuzawa H, Maruyama T, Misawa N, Fujimori K, Nakano M (2000) Quenching of singlet oxygen by carotenoids produced in Escherichia coli-attenuation of singlet oxygen-mediated bacterial killing by carotenoids. FEBS Lett 484:280-284
35. Teramoto M, Takaichi S, Inomata Y, Ikenaga H, Misawa N (2003) Structural and functional analysis of a lycopene β-monocyclase gene isolated from a unique marine bacterium that produces myxol. FEBS Lett 545:120-126
36. Teramoto M, Rahlert 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
37. Thompson JD, Gibson TJ, Plewniak F, Jeanmougin F, Higgins DG (1997) The ClustalX windows interface: flexible strategies for multiple sequence alignment aided by quality analysis tools. Nucleic Acids Res 24:4876-4882
38. Umeno D, Tobias AV, Arnold FH (2005) Diversifying carotenoid biosynthetic pathways by directed evolution. Microbiol Mol Biol Rev 69:51-78
39. Ye X, Al-Babili S, Kloti A, Zhang J, Lucca P, Beyer P, Potrykus I (2000) Engineering the provitamin A (beta-carotene) biosynthetic pathway into (carotenoid-free) rice endosperm. Science 287:303-305
40. Yokoyama A, Miki W (1995a) Isolation of myxol from a marine bacterium Flavobacterium sp. associated with a marine sponge. Fish Sci 61:684-686
41. Yokoyama A, Miki W (1995b) Composition and presumed biosynthetic pathway of carotenoids in the astaxanthin-producing bacterium Agrobacterium aurantiacum. FEMS Microbiol Lett 128:139-144
42. Yokoyama A, Izumida H, Miki W (1994) Production of astaxanthin and 4-ketozeaxanthin by the marine bacterium, Agrobacterium aurantiacum. Biosci Biotechnol Biochem 58:1842-1844
43. Yokoyama A, Adachi K, Shizuri Y (1995) New carotenoid glycosides, astaxanthin glucoside and adonixanthin glucoside, isolated from the astaxanthin-producing marine bacterium Agrobacterium aurantiacum. J Nat Prod 58:1929-1933
44. Yokoyama A, Miki W, Izumida H, Shizuri Y (1996) New trihydroxy-keto- carotenoids isolated from an astaxanthin-producing marine bacterium. Biosci Biotechnol Biochem 60:200-203