Unique Carotenoids in the Terrestrial Cyanobacterium Nostoc commune NIES-24: 2-Hydroxymyxol 2′-Fucoside, Nostoxanthin and Canthaxanthin
- 336 Downloads
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.
KeywordsHigh Performance Liquid Chromatography Carotenoid Zeaxanthin Anabaena Nostoc
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.
- 1.Britton G, Liaaen-Jensen S, Pfander H (2004) Carotenoids handbook. Birkhäuser Verlag, BaselGoogle Scholar
- 5.Goodwin TW (1980) The biochemistry of the carotenoids, vol 1: Plants, 2nd edn. Chapman and Hall, LondonGoogle Scholar
- 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
- 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.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
- 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.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.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
- 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
- 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 (https://www.novapublishers.com/catalog/product_info.php?products_id=9524)
- 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