Mycosporine-2-glycine is the major mycosporine-like amino acid in a unicellular cyanobacterium (Euhalothece sp.) isolated from a gypsum crust in a hypersaline saltern pond
Laura Kedar
Division of Microbial and Molecular Ecology, Institute of Life Sciences, and The Moshe Shilo Minerva Center for Marine Biogeochemistry, The Hebrew University of Jerusalem, 91904 Jerusalem, Israel
Search for more papers by this authorYoel Kashman
School of Chemistry, Tel Aviv University, 69978 Ramat Aviv, Israel
Search for more papers by this authorCorresponding Author
Aharon Oren
Division of Microbial and Molecular Ecology, Institute of Life Sciences, and The Moshe Shilo Minerva Center for Marine Biogeochemistry, The Hebrew University of Jerusalem, 91904 Jerusalem, Israel
*Corresponding author. Tel.: +972 (2) 6584951; Fax: +972 (2) 6528008, E-mail: [email protected]Search for more papers by this authorLaura Kedar
Division of Microbial and Molecular Ecology, Institute of Life Sciences, and The Moshe Shilo Minerva Center for Marine Biogeochemistry, The Hebrew University of Jerusalem, 91904 Jerusalem, Israel
Search for more papers by this authorYoel Kashman
School of Chemistry, Tel Aviv University, 69978 Ramat Aviv, Israel
Search for more papers by this authorCorresponding Author
Aharon Oren
Division of Microbial and Molecular Ecology, Institute of Life Sciences, and The Moshe Shilo Minerva Center for Marine Biogeochemistry, The Hebrew University of Jerusalem, 91904 Jerusalem, Israel
*Corresponding author. Tel.: +972 (2) 6584951; Fax: +972 (2) 6528008, E-mail: [email protected]Search for more papers by this authorAbstract
Mycosporine-like amino acids (MAAs) were extracted from a unicellular cyanobacterium (Euhalothece sp.) isolated from a gypsum crust on the bottom of a hypersaline saltern pond in Eilat, Israel. When grown at high light intensities, this isolate contained high concentrations of two MAAs, one showing maximum optical density at 331 nm and one at 362 nm. The compound absorbing at 331 nm was purified by preparative high performance liquid chromatography, and its structure was elucidated by one-dimensional (1H and 13C) and two-dimensional nuclear magnetic resonance, mass spectrometry and amino acid analysis, and identified as mycosporine-2-glycine. This is the first report of mycosporine-2-glycine in cyanobacteria.
References
- [1] Dunlap, W.C., Shick, J.M. (1998) Ultraviolet radiation-absorbing mycosporine-like amino acids in coral reef organisms: a biochemical and environmental perspective. J. Phycol. 34, 418–430.
- [2] Sinha, R.P., Klisch, M, Gröniger, A, Häder, D.P. (1998) Ultraviolet-absorbing/screening substances in cyanobacteria, phytoplankton and macroalgae. J. Photochem. Photobiol. B Biol. 47, 83–94.
- [3] Adams, N.L., Shick, J.M. (1996) Mycosporine-like amino acids provide protection against ultraviolet radiation in eggs of the green sea urchin Strongylocentrotus droebachiensis. Photochem. Photobiol. 64, 149–158.
- [4] Garcia-Pichel, F, Wingard, C.E., Castenholz, R.W. (1993) Evidence regarding the UV sunscreen role of a mycosporine-like compound in the cyanobacterium Gloeocapsa sp.. Appl. Environ. Microbiol. 59, 170–176.
- [5] Karsten, U, Maier, J, Garcia-Pichel, F (1998) Seasonality in UV-absorbing compounds of cyanobacterial mat communities from an intertidal mangrove flat. Aquat. Microb. Ecol. 16, 37–44.
- [6] Quesada, A, Vincent, W.F., Lean, D.R.S. (1999) Community and pigment structure of Arctic cyanobacterial assemblages: the occurrence and distribution of UV-absorbing compounds. FEMS Microbiol. Ecol. 28, 315–323.
- [7] Sommaruga, R, Garcia-Pichel, F (1999) UV-absorbing mycosporine-like compounds in planktonic and benthic organisms from a high-mountain lake. Arch. Hydrobiol. 144, 255–269.
- [8] Castenholz, R.W. and Garcia-Pichel, F. (2000) Cyanobacterial responses to UV-radiation. In: Ecology of Cyanobacteria. Their Diversity in Time and Space (Whitton, B.A. and Potts, M., Eds.), pp. 591–611. Kluwer Academic Publishers, Dordrecht.
- [9] Garcia-Pichel, F, Castenholz, R.W. (1993) Occurrence of UV-absorbing, mycosporine-like compounds among cyanobacterial isolates and an estimate of their screening capacity. Appl. Environ. Microbiol. 59, 163–169.
- [10] Portwich, A, Garcia-Pichel, F (1999) Ultraviolet and osmotic stresses induce and regulate the synthesis of mycosporines in the cyanobacterium Chlorogloeopsis PCC 6912. Arch. Microbiol. 172, 187–192.
- [11] Sinha, R.P., Klisch, M, Häder, D.P. (1999) Induction of a mycosporine-like amino acid (MAA) in the rice-field cyanobacterium Anabaena sp. by UV irradiation. J. Photochem. Photobiol. B Biol. 52, 59–64.
- [12] Garcia-Pichel, F, Nübel, U, Muyzer, G (1998) The phylogeny of unicellular, extremely halotolerant cyanobacteria. Arch. Microbiol. 169, 469–482.
- [13] Oren, A (1997) Mycosporine-like amino acids as osmotic solutes in a community of halophilic cyanobacteria. Geomicrobiol. J. 14, 231–240.
- [14] Oren, A, Kühl, M, Karsten, U (1995) An endevaporitic microbial mat within a gypsum crust: zonation of phototrophs, photopigments, and light penetration. Mar. Ecol. Prog. Ser. 128, 151–159.
- [15] Yopp, J.H., Tindall, D.R., Miller, D.M., Schmidt, W.E. (1978) Isolation, purification and evidence for the halophilic nature of the blue-green alga Aphanothece halophytica. Phycologia 17, 172–178.
- [16] Nakamura, H, Kobayashi, J, Hirata, Y (1982) Separation of mycosporine-like amino acids in marine organisms using reversed-phase high-performance liquid chromatography. J. Chromatogr. 250, 113–118.
- [17] Betnér, I, Földi, P (1986) New automated amino acid analysis by HPLC precolumn derivatization with fluorenylmethyloxycarbonylchloride. Chromatographia 22, 381–387.
- [18] Stochaj, W.R., Dunlap, W.C., Shick, J.M. (1994) Two new UV-absorbing mycosporine-like amino acids from the sea anemone Anthopleura elegantissima and the effects of zooxanthellae and spectral irradiance on chemical composition and content. Mar. Biol. 118, 149–156.
- [19] Carefoot, T.H., Harris, M, Taylor, B.E., Donovan, D, Karentz, D (1998) Mycosporine-like amino acids: possible UV protection in eggs of the sea hare Aplysia dactylomela. Mar. Biol. 130, 389–396.
- [20] Adams, N.L., Shick, J.M., Dunlap, W.C. (2001) Selective accumulation of mycosporine-like amino acids in ovaries of the green sea urchin Strongylocentrotus droebachiensis is not affected by ultraviolet radiation. Mar. Biol. 138, 281–294.
- [21] Helbling, E.W., Chalker, B.E., Dunlap, W.C., Holm-Hansen, O, Villafane, V.E. (1996) Photoacclimation of Antarctic marine diatoms to solar ultraviolet radiation. J. Exp. Mar. Biol. Ecol. 204, 85–101.
- [22] Gröniger, A, Sinha, R.P., Klisch, M, Häder, D.P. (2000) Photoprotective compounds in cyanobacteria, phytoplankton and macroalgae – a database. J. Photochem. Photobiol. B Biol. 58, 115–122.
- [23] Budel, B, Karsten, U, Garcia-Pichel, F (1997) Ultraviolet-absorbing scytonemin and mycosporine-like amino acid derivatives in exposed, rock-inhabiting cyanobacterial lichens. Oecologia 112, 165–172.
- [24] Karsten, U, Garcia-Pichel, F (1996) Carotenoids and mycosporine-like amino acid compounds in members of the genus Microcoleus (cyanobacteria): a chemosystematic study. Syst. Appl. Microbiol. 19, 285–294.
- [25] Böhm, G.A., Pfleiderer, W, Böger, P, Scherer, S (1995) Structure of a novel oligosaccharide-mycosporine-amino acid ultraviolet A/B sunscreen pigment from the terrestrial cyanobacterium Nostoc commune. J. Biol. Chem. 270, 8536–8539.
