Current Microbiology

, Volume 59, Issue 4, pp 413–419 | Cite as

Unique Carotenoids in the Terrestrial Cyanobacterium Nostoc commune NIES-24: 2-Hydroxymyxol 2′-Fucoside, Nostoxanthin and Canthaxanthin

  • Shinichi TakaichiEmail author
  • Takashi Maoka
  • Mari Mochimaru


Cyanobacteria produce some carotenoids. We identified the molecular structures, including the stereochemistry, of all the carotenoids in the terrestrial cyanobacterium, Nostoc commune NIES-24 (IAM M-13). The major carotenoid was β-carotene. Its hydroxyl derivatives were (3R)-β-cryptoxanthin, (3R,3′R)-zeaxanthin, (2R,3R,3′R)-caloxanthin, and (2R,3R,2′R,3′R)-nostoxanthin, and its keto derivatives were echinenone and canthaxanthin. The unique myxol glycosides were (3R,2′S)-myxol 2′-fucoside and (2R,3R,2′S)-2-hydroxymyxol 2′-fucoside. This is only the second species found to contain 2-hydroxymyxol. We propose possible carotenogenesis pathways based on our identification of the carotenoids: the hydroxyl pathway produced nostoxanthin via zeaxanthin from β-carotene, the keto pathway produced canthaxanthin from β-carotene, and the myxol pathway produced 2-hydroxymyxol 2′-fucoside via myxol 2′-fucoside. This cyanobacterium was found to contain many kinds of carotenoids and also displayed many carotenogenesis pathways, while other cyanobacteria lack some carotenoids and a part of carotenogenesis pathways compared with this cyanobacterium.


High Performance Liquid Chromatography Carotenoid Zeaxanthin Anabaena Nostoc 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.



The authors wish to thank Professors M. Tanaka and T. Sanji, Tokyo Institute of technology, for their help in measuring CD spectra, and Dr. T. Sakamoto, Kanazawa University, for his gift of N. commune natural field sample.

Supplementary material

284_2009_9453_MOESM1_ESM.pdf (26 kb)
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  1. 1.
    Britton G, Liaaen-Jensen S, Pfander H (2004) Carotenoids handbook. Birkhäuser Verlag, BaselGoogle Scholar
  2. 2.
    Buchecker R, Liaaen-Jensen S, Borch G, Siegelman HW (1976) Carotenoids of Anacystis nidulans, structures of caloxanthin and nostoxanthin. Phytochemistry 15:1015–1018CrossRefGoogle Scholar
  3. 3.
    Cunningham FX Jr, 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 6:1107–1121PubMedCrossRefGoogle Scholar
  4. 4.
    Goodwin TW (1957) The nature and distribution of carotenoids in some blue-green algae. J Gen Microbiol 17:467–473PubMedGoogle Scholar
  5. 5.
    Goodwin TW (1980) The biochemistry of the carotenoids, vol 1: Plants, 2nd edn. Chapman and Hall, LondonGoogle Scholar
  6. 6.
    Graham JE, Bryant DA (2009) The biosynthetic pathway for myxol 2′-fucoside (myxoxanthophyll) in the cyanobacterium Synechococcus sp. strain PCC 7002. J Bacteriol 191:3292–3300PubMedCrossRefGoogle Scholar
  7. 7.
    Hirschberg J, Chamovitz D (1994) Carotenoids in cyanobacteria. In: Bryant DA (ed) The molecular biology of cyanobacteria. Kluwer Academic Publishers, Dordrecht, pp 559–579Google Scholar
  8. 8.
    Iwai M, Maoka T, Ikeuchi M, Takaichi S (2008) 2,2′-Hydoxylase (CrtG) is involved in carotenogenesis of both nostoxanthin and 2-hydroxymyxol 2′-fucoside in Thermosynechococcus elongatus strain BP-1. Plant Cell Physiol 49:1678–1687PubMedCrossRefGoogle Scholar
  9. 9.
    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 106:99–104Google Scholar
  10. 10.
    Makino T, Harada H, Ikenaga H, Matsuda S, Takaichi S, Shindo K, Sandmann G, Ogata T, Misawa N (2009) Characterization of cyanobacterial carotenoid ketolase CrtW and hydroxylase CrtR by complementation analysis in Escherichia coli. Plant Cell Physiol 50:1867–1878Google Scholar
  11. 11.
    Maresca JA, Graham JE, Wu M, Eisen JA, Bryant DA (2007) Identification of a forth family of lycopene cyclases in photosynthetic bacteria. Proc Natl Acad Sci USA 104:11784–11789PubMedCrossRefGoogle Scholar
  12. 12.
    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 579:6111–6114PubMedCrossRefGoogle Scholar
  13. 13.
    Mochimaru M, Masukawa H, Maoka T, Mohamed HE, Vermaas WFJ, 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 190:6726–6733PubMedCrossRefGoogle Scholar
  14. 14.
    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 71:4286–4296PubMedCrossRefGoogle Scholar
  15. 15.
    Rippka R, Castenholz RW, Herdman M (2001) Subsection IV. (Formerly Nostocales Castenholz 1989b sensu Rippka, Deruelles, Waterbury, Herdman and Stanier 1979). In: Boone DR, Castenholz RW (eds) Bergey’s manual of systematic bacteriology, vol 1, 2nd edn. Springer, New York, pp 562–566Google Scholar
  16. 16.
    Sakamoto T, Yoshida T, Arima H, Hatanaka Y, Takani Y, Tamaru Y (2009) Accumulation of trehalose in response to desiccation and salt stress in the terrestrial cyanobacterium Nostoc commune. Phycol Res 57:66–73CrossRefGoogle Scholar
  17. 17.
    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 74:1350–1357PubMedCrossRefGoogle Scholar
  18. 18.
    Steiger S, Sandmann G (2004) Cloning of two carotenoid ketolase genes from Nostoc punctiforme for the heterogous production of canthaxanthin and astaxanthin. Biotechnol Lett 26:813–817PubMedCrossRefGoogle Scholar
  19. 19.
    Stickforth P, Steiger S, Hess WR, Sandmann G (2003) A novel type of lycopene ε-cyclase in the marine cyanobacterium Prochlorococcus marinus MED4. Arch Microbiol 179:409–415PubMedGoogle Scholar
  20. 20.
    Stransky H, Hager A (1970) The carotenoid pattern and the occurrence of the light induced xanthophylls cycle in various classes of algae. IV. Cyanophyceae and Rhodophyceae. Arch Mikrobiol 72:84–96PubMedCrossRefGoogle Scholar
  21. 21.
    Takaichi S, Shimada K (1992) Characterization of carotenoids in photosynthetic bacteria. Methods Enzymol 213:374–385CrossRefGoogle Scholar
  22. 22.
    Takaichi S, Mochimaru M (2007) Carotenoids and carotenogenesis in cyanobacteria: unique ketocarotenoids and carotenoid glycosides. Cell Mol Life Sci 64:2607–2619PubMedCrossRefGoogle Scholar
  23. 23.
    Takaichi S, Mochimaru M (2009) Carotenoids, their diversity and carotenogenesis in cyanobacteria. In: Gault PM, Marler HJ (eds), Handbook of cyanobacteria: biochemistry, biotechnology and applications. Nova Science Publishers, New York, in press (
  24. 24.
    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 42:756–762PubMedCrossRefGoogle Scholar
  25. 25.
    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 46:497–504PubMedCrossRefGoogle Scholar
  26. 26.
    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 47:211–216PubMedCrossRefGoogle Scholar
  27. 27.
    Tao L, Rouvière PE, Cheng Q (2006) A carotenoid synthesis gene cluster from a non-marine Brevundimonas that synthesizes hydroxylated astaxanthin. Gene 379:101–108PubMedCrossRefGoogle Scholar
  28. 28.
    Yokoyama A, Miki W (1995) Isolation of myxol from a marine bacterium Flavobacterium sp. associated with a marine sponge. Fish Sci 61:684–686Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  • Shinichi Takaichi
    • 1
    Email author
  • Takashi Maoka
    • 2
  • Mari Mochimaru
    • 3
  1. 1.Department of BiologyNippon Medical SchoolKawasakiJapan
  2. 2.Research Institute for Production DevelopmentKyotoJapan
  3. 3.Department of Natural SciencesKomazawa UniversityTokyoJapan

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