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 and Cell Physiology

Volumn 46, Issue 3, 2005, Pages 497-504

  Takaichi, Shinichi ^a   Mochimaru, Mari ^b   Maoka, Takashi ^c   Katoh, Hiroshi ^d,e  

^a NIPPON MEDICAL SCHOOL   (Japan)

^b KOMAZAWA UNIVERSITY   (Japan)

^c KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^d UNIVERSITY OF TOKYO   (Japan)

^e MIE UNIVERSITY   (Japan)

Author keywords

4 Ketomyxol 2 fucoside; Anabaena; Carotenogenesis; Carotenoid; Myxol 2 fucoside; Nostoc

Indexed keywords

CAROTENOID; FUCOSE; PIGMENT; RHAMNOSE;

ANABAENA; ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; GENE EXPRESSION REGULATION; GENETICS; GENOME; METABOLISM; MOLECULAR EVOLUTION; MOLECULAR GENETICS; NOSTOC; PHYLOGENY; SEQUENCE HOMOLOGY;

ANABAENA; CAROTENOIDS; EVOLUTION, MOLECULAR; FUCOSE; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENE EXPRESSION REGULATION, PLANT; GENOME, PLANT; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; NOSTOC; PHYLOGENY; PIGMENTS, BIOLOGICAL; RHAMNOSE; SEQUENCE HOMOLOGY, AMINO ACID; SEQUENCE HOMOLOGY, NUCLEIC ACID;

ANABAENA; ANABAENA SP.; ANABAENA VARIABILIS; NOSTOC; NOSTOC PUNCTIFORME PCC 73102; NOSTOC SP.; NOSTOC SP. HK-01; NOSTOC SP. PCC 7120;

EID: 16344396168     PISSN: 00320781     EISSN: None     Source Type: Journal    
DOI: 10.1093/pcp/pci049     Document Type: Article

References (33)

1. Aakermann, T., Skulberg, O.M. and Liaaen-Jensen, S. (1992) A comparison of the carotenoids of strains of Oscillatoria and Spirulina (cyanobacteria). Biochem. System. Ecol. 20: 761-769.
2. Breitenbach, J., Fernández-González, B., Vioque, A. and Sandmann, G. (1998) A higher-plant type ζ-carotene desaturase in the cyanobacterium Synechocystis PCC6803. Plant Mol. Biol. 36: 725-732.
3. Britton, G., Liaaen-Jensen, S. and Pfander, H. (2004) Carotenoids, Handbook. Birkhäuser, Basel.
4. Cohen, M.F., Meeks, J.C., Cai, Y.A. and Wolk, C.P. (1998) Transposon mutagenesis of heterocyst-forming filamentous cyanobacteria. Methods Enzymol. 297: 1-17.
5. Felsenstein, J. (1985) Confidence limits on phylogenies: an approach using the bootstrap. Evolution 39: 783-791.
6. Foss, P., Skulberg, O.M., Kilaas, L. and Liaaen-Jensen, S. (1986) The carbohydrate moieties bound to the carotenoids myxol and oscillol and their chemosystematic applications. Phytochemistry 25: 1127-1132.
7. Frigaard, N.-F., Maresca, J.A., Yunker, C.E., Jones, A.D. and Bryant, D.A. (2004) Genetic manipulation of caroteniod biosynthesis in the green sulfur bacterium Chlorobium tepidum. J. Bacteriol. 186: 5210-5220.
8. Hertzberg, S., Borch, G. and Liaaen-Jensen, S. (1976) Bacterial carotenoids: L. Absolute configuration of zeaxanthin dirhamnoside. Arch. Microbiol. 110: 95-99.
9. Hirschberg, J. and Chamovitz, D. (1994) Carotenoids in cyanobacteria. In The Molecular Biology of Cyanobacteria. Edited by Bryant, D.A. pp. 769-823. Kluwer Academic Publishers. Dordrecht.
10. Kaneko, T., Nakamura, Y., Wolk, C.P., Kuritz, T., Sasamoto, S.et al. (2001) Complete genomic sequence of the filamentous nitrogen-fixing cyanobacterium Anabaena sp. strain PCC 7120. DNA Res. 8: 205-213.
11. Katoh, H., Shiga, Y., Nakahira, Y. and Ohmori, M. (2003) Isolation and characterization of a drought-tolerant cyanobacterium, Nostoc sp. HK-01. Microb. Environ. 18: 82-88.
12. Lagarde, D. and 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.
13. Linden, H., Misawa, N., Saito, T. and 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.
14. Maresca, J.A., Frigaard, N.-F. and Bryant, D.A. (2005) Identification of a novel class of lycopene cyclases in photosynthetic bacteria. In Photosynthesis: Fundamental Aspects to Global Perspectives. Edited by van der Est, A. and Bruce, D., in press. Allen Press, Canada.
15. Martínez-Férez, I., Fernández-González, B., Sandmann, G. and 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.
16. Martínez-Férez, I. and 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.
17. Masamoto, K., Misawa, N., Kaneko, T., Kikuno, R. and Toh, H. (1998) β-Carotene hydroxylase gene from the cyanobacterium Synechocystis sp. PCC6803. Plant Cell Physiol. 39: 560-564.
18. Masamoto, K., Wada, H., Kaneko, T. and 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.
19. Mohamed, H.E. and 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.
20. Murray, M.G. and Thompson, W.F. (1980) Rapid isolation of high molecular weight plant DNA. Nucleic Acids Res. 8: 4321-4325.
21. Niggli, U.A. and Pfander, H. (1999) Carotenoid glycosides and glycosyl esters. In Naturally Occurring Glycosides. Edited by Ikan, R. pp. 125-145. John Wiley & Sons, Chichester.
22. Ohto, C., Ishida, C., Nakane, H., Muramatsu, M., Nishino, T. and Obata, S. (1999) A thermophilic cyanobacterium Synechococcus elongatus has three different class I prenyltransferase genes. Plant Mol. Biol. 40: 307-321.
23. Omata, T. and Murata, N. (1984) Isolation and characterization of three types of membranes from the cyanobacterium (blue-green alga) Synechocystis PCC 6714. Arch. Microbiol. 139: 113-116.
24. Rippka, R. (1988) Isolation and purification of cyanobacteria. Methods Enzymol. 167: 3-27.
25. Rippka, R., Castenholz, R.W. and Herdman, M. (2001) Subsection IV. In Bergey's Manual of Systematic Bacteriology, 2nd edn, Vol. I. Edited by Boone, D.R. and Castenholz, R.W. pp. 562-589. Springer, New York.
26. Rippka, R., Deruelles, J., Waterbury, J.B., Herdman, M. and Stanier, R.Y. (1979) Genetic assignments, strain histories and properties of pure culture of cyanobacteria. J. Gen. Microbiol. 111: 1-61.
27. Saitou, N. and Nei, M. (1987) The neighbor-joining method: a new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 4: 406-425.
28. Steiger, S. and 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.
29. Takaichi, S. (1999) Carotenoids and carotenogenesis in anoxygenic photosynthetic bacteria. In The Photochemistry of Carotenoids. Edited by Frank, H.A., Young, A.J., Britton, G. and Cogdell, R.J. pp. 39-69. Kluwer Academic Publishers, Dordrecht.
30. Takaichi, S., Maoka, T. and 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.
31. Takaichi, S. and Shimada, K. (1992) Characterization of carotenoids in photosynthetic bacteria. Methods Enzymol. 213: 374-385.
32. Thompson, J.D., Higgins, D.G. and Gibson, T.J. (1994) CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position specific gap penalties and weight matrix choice. Nucleic Acids Res. 22: 4673-4680.
33. Wolk, C.P., Ernst, A. and Elhai, J. (1994) Heterocyst metabolism and deveopment. In The Molecular Biology of Cyanobacteria. Edited by Bryant, D.A. pp. 769-823. Kluwer Academic Publishers. Dordrecht.