Nodularyny i inne toksyny produkowane przez cyjanobakterie (sinice)

• Autorzy: Mazur-Marzec H. , Toruńska A.

Warianty tytułu

EN

Nodularins and other toxins produced by cyanobacteria (blue-green algae)

• Języki publikacji: PL

Abstrakty

EN

Cyanobacteria are photosynthetic prokaryotes that produce a wide range of secondary metabolites. Part of them is toxic or shows bioactivity in other organisms, including mammals . The main classes of cyanobacterial toxins comprise of hepatotoxins, neurotoxins, cytotoxins, dermatotoxins and lipopolysaccharides. Hepatotoxins, microcystins and nodularins are the most common cyanotoxins. Microcystins, the cyclic heptapeptides are produced by freshwater cyanobacteria of the genera Microcystis, Anabaena, Planktothrix (Oscillatoria), Nostoc, Hapalosiphon and Anabaenopsis. Nodularin (NOD-R) the cyclic pentapeptide hepatotoxin is produced by brackish water cyanobacterium Nodularia spumigena. Microcystins and nodularins are extremely toxic due to their action on type 1 and 2A protein phosphatase enzymes that play a key role in the control of cellular meta-bolism. The main groups of neurotoxins produced by cyanobacteria include anatoxin-a, anatoxin-a(s), saxitoxins and the recently identified B-N-methylamino--L-alanine (BMAA). The latter has been reported to biomagnify within the Guam ecosystem and was suggested to be a possible cause of the amyotrophic lateral sclerosis/parkinsonism-dementia complex (ALS/PDC). In the Baltic Sea N. spumigena is the main toxic and bloom-forming cyanobacterial species [7]. Nodularin concentration can temporarily reach over 20 mg dm-3. The toxin accumulates in different elements of the Baltic ecosystem, including sediments, mussels and fish. Apart from NOD-R, minor amounts of other NOD analogues have been characterized in N. spumigena cells: geometrical isomers, linear forms, three demethylated analogues and three analogues with additional methyl group. Nodularin is characterized by high stability. The loss of the toxin in water is mainly due to degradation by the naturally occurring bacterial community. However, the UV radiation as well as sorption on sediments and sus-pended particles has also some impact on nodularin concentration. In organisms microcystins are detoxified by conjugation with activated glutathione, however, the pathway of nodularin biotransformation has not been revealed yet.

Słowa kluczowe

PL

cyjanobakterie; hepatotoksyny; neurotoksyny; nodularyny; Nodularia spumigena

EN

cyanobacteria; hepatotoxins; neurotoxins; nodularins; Nodularia spumigena

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2007
• Tom: [Z] 61, 3-4
• Strony: 247--277
• Opis fizyczny: bibliogr. 150 poz., tab., wykr.

Twórcy

autor

Mazur-Marzec H.

autor

Toruńska A.

• Instytut Oceanografii, Uniwersytet Gdański, Al. Marszałka Piłsudskiego 46, 81-378 Gdynia

Bibliografia

• [1] T. Kuiper-Goodman, I.R. Falconer, J. Fitzgerald, [w:] Toxic cyanobacteria in water: a guide to their public health consequences, monitoring and management, red. I. Chorus, J. Bartram, E. & F.N. Spon, London-New York, 1999, s. 41-111.
• [2] I.R. Falconer, [w:] Cyanobacterial toxins of drinking waters supplies, CRC Press, London, 2005.
• [3] G.A. Codd, S.G. Bell, K. Kaya, C.J. Ward, K.A. Beattie, J.S. Metcalf, Eur. J. Phycol., 1999, 34, 405.
• [4] I.R. Falconer, J. Bartram, I. Chorus I., T. Kuiper-Goodman, H. Utkilen, M. Burch, G.A. Codd, [w:] Toxic cyanobacteria in water: a guide to their public health consequences, monitoring and management, red. I. Chorus, J. Bartram, E. & F.N. Spon, London-New York, 1999, s. 41-111.
• [5] A.M. Burja, B. Banaigs, E. Abou-Mansour, J.G. Burgess, P.C. Wright, Tetrahedron, 2001, 57, 9347.
• [6] B.A. Neilan, E. Dittmann, L. Rouhiainen, R.A. Bass, V. Schaub, K. Sivonen, T. Bomer, J. Bacterial., 1998, 181, 4089.
• [7] D. Tillett, E. Dittmann, M. Erhard, H. Döhren, T. Börner, B.A. Neilan, Chem. Biol., 2000, 7, 753.
• [8] K.L. Rinehart, K. Harada, M. Namikoshi, C. Chen, C.E. Harris, M.H.G. Munro J.W. Blunt, P.E. Mulligan, V.R. Beasley, A.M. Dahlem, W.W. Carmichael, J. Am. Chem. Soc., 1988, 110, 8557.
• [9] K.L. Reinehart, M. Namikoshi, B.W. Choi, J. Appl. Phycol., 1994, 6, 159.
• [10] D. P. Botes, A.A. Tuinman, P.L. Wessels, C.C. Viljoen, H. Kruger, D.H. Williams, S. Santikarn, E.J. Smith, S.J. Hammond, J. Chem. Soc. PerkinTrans., 1984, 1, 2311.
• [11] K. Sivonen, G. Jones, [w:] Toxic cyanobacteria in water: a guide to their public health consequences, monitoring and management, red. I. Chorus, J. Bartram, E. & F.N. Spon, London-New York, 1999, s. 41-111.
• [12] L. Shi, W.W. Carmichael, I. Miller, Arch. Microbiol., 1995, 163, 7.
• [13] L. Spoof, [w:] Cyanobacterial Monitoring and Cyanotoxin, red. J. Meriluoto, G.A. Codd, Abo, 2005, s. 1-149.
• [14] M.T.C. Runnegar, R.G. Gerdes, I.R. Falconer, Toxicon, 1991, 29, 43.
• [15] I.R. Falconer, A.R. Humpage, Phycologia, 1996, 35, 74.
• [16] T. Ohta, E. Sueoka, N. Iida, A. Komori, M. Suganuma, R. Nishiwaki, M. Tatematsu, S.J. Kim, W.W. Carmichael, H. Fujiki, Cancer Res., 1994, 54, 6402.
• [17] C. Mackintosh, K.A. Beattie, S. Klumpp, P. Cohen, G.A. Codd, FEBS Letters, 1990, 264, 187.
• [18] I.R. Falconer, M. Runnegar, T. Buckley, V. Heyn, P. Bradshaw, J. Am. Water Works, 1989, 81, 1021.
• [19] S. Yoshizawa, R. Matsushima, M.F. Watanabe, K.I. Harada, A. Ichihara, W.W. Carmichael, H. Fujiki, J.Cancer Res. Clin. Oncol., 1990, 116, 609.
• [20] A. Lankoff, A. Banasik, M. Nowak, Arch. Toxicol., 2002, 76, 158.
• [21] N. Bouaicha, I. Maatouk, Tox. Let., 2004, 148, 53.
• [22] J. Goldberg, H.B. Huang, Y.G. Kwon, P. Greengard, A.C. Nairn, J. Kuriyan, Nature, 995, 376, 745.
• [23] K.I. Harada, S. Imanishi, H. Kato, M. Mizuno, E. Ito, K. Tsuji, Toxicon, 2004, 44, 107.
• [24] J. An, W.W. Carmichael, Toxicon, 1994, 32, 1495.
• [25] F.H., Kondo, H. Matsumoto, S. Yamada, N. Ishikawa, E. Ito, S. Nagata, Y. Ueno, M. Suzuki, K.I. Harada, Chem. Res. Toxicol., 1996, 9, 1355.
• [26] J.P. Devlin, O.E. Edwards, P.R. Gorham, M.R. Hunter, R.K. Pike, B. Stavric, Canad. J. Chem., 1977, 55, 1367.
• [27] S. Haider, V. Naithani, P.N. Viswanathan, P. Kakkar, Chemosphere, 2003, 52, 1.
• [28] O.M. Skulberg, W.W. Carmichael, R.A. Anderson, S. Matsunaga, R.E. Moore, R. Skulberg, Environ. Toxicol. Chem. 1992, 11, 321.
• [29] F.M.B. Ferreira, J.M.F. Soler, M.L. Fidalgo, P. Fernandez-Vila, Toxicon, 2001, 39, 757.
• [30] A.R. Humpage, J. Rositano, A.H. Bretag, R. Brown, P.D. Baker, B.C. Nicholson, D.A. Steffensen, J. Mar. Freshwater Res., 1994, 45, 761.
• [31] C.S. Dow, U.K. Swoboda, [w:] The ecology of cyanobacteria, red. B.A. Whitton & M.Potts, Kluwer Academic Publishers, 2000, 613.
• [32] P.A. Cox, S.A. Banack, S.J. Murch, Proc. Natl. Acad. Sci. USA, 2003, 100, 13380
• [33] A. Vega, A. Bell, Phytochemistry, 1967, 6, 759.
• [34] P. Spencer, P. Nunn, J. Hugon, A. Ludolph, D. Roy, Lancet, 1986, 1, 965.
• [35] M.W. Duncan, N.E. Villacreses, P.G. Pearson, L. Watt, S.I. Rapoport, I.J. Kopin, S.P. Markey, Q.R. Smith, J. Pharmacol. Exp. Ther., 1991, 258, 27.
• [36] P.A. Cox, S.A. Banack, S.J. Murch, U. Rasmussen, G. Tien, R.R. Bidigare, J.S. Matclaf, L.F. Morrison, G.A. Codd, B. Bergman, Proc. Natl. Acad. Sci. USA, 2005, 102, 5074.
• [37] D.J. Griffiths, M.L. Saker, Environ. Toxicol., 2003, 18, 78.
• [38] A.R. Humpage, I.R. Falconer, Environ. Toxicol., 2003, 19, 94.
• [39] N.J.T. Osborne, P.M. Webb, G.R. Shaw, Environ. International, 2001, 27, 381.
• [40] J.H. Best, S. Pflugmacher, C. Wiegand, F.B. Eddy, J.S. Metcalf, G. Codd, Aquatic Toxicol, 2002, 60, 223.
• [41] J. Rapala, K. Lahti, L.A. Rasanen, A.L. Esala, S.I. Niemela, K.Sivonen, Wat. Res., 2002, 36, 2627.
• [42] M. Pliński, T. Jóźwiak, [w:] B.A. Whitton, M. Potts (red.), Harmful and Toxic Algal Blooms, Intergovernmental Oceanographic Commission of UNESCO, 1996, 549.
• [43] T.S. Bianchi, E. Engelhaupt, P. Westman, T. Andrén, C. Rolff, R. Elmgren, Limnol. Oceanogr., 2000, 45, 716.
• [44] T. Finni, K. Kononen, R. Olsonen, K. Wallström, Ambio, 2001, 30, 172.
• [45] L.J. Stal, P. Albertano, B. Bergman, K. von Bröcel, J.R. Gallon, P.K. Hayes, K. Sivonen, A.E. Walsby, Cont. Shelf Res., 2003, 23, 1695.
• [46] H. Mazur, M. Pliński, Oceanologia, 2003, 45, 305.
• [47] H. Mazur-Marzec, Oceanologia, 2006, 48, 1.
• [48] I.R. Falconer, Phycologia, 2001, 40, 228.
• [49] T. Heresztyn, B.C. Nicholson, Environ. Toxicol. Wat. Qual., 1997, 12, 273.
• [50] W.W. Carmichael, J.T. Eschedor, G.M.L. Patterson, R.E. Moore, Environ. Microbiol., 1988, 54, 2257.
• [51] W.R. Harding, N. Rowe, J.C. Wessels, K.A. Beattie, G.A. Codd, J. of the SAVA, 1995, 66, 256.
• [52] G.J. Jones, S.I. Blackburn, N.S.Parker, Australian J. of Marine Freshwater Res., 1994, 45, 787.
• [53] D.L. Galat, J.P., Verdin, L.L. Sims, Hydrobiol., 1990, 197, 147.
• [54] M. Hansson, SMHI - Swedish Meteorol. Hydrol. Inst. Rep. Hydrol., 2006, 82, 38.
• [55] K. Sivonen, K. Kononen, W.W. Carmichael, A.M. Dahlem, K.L. Rinehart, J. Kiviranta, I. Niemelä, Appl. Environ. Microbiol., 1989, 55, 1990.
• [56] A. Sandstrom, C.Glemarec, J.A.O. Meriluoto, J.E. Eriksson, Toxicon, 1990, 28, 535.
• [57] M. Namikoshi, B.W. Choi, R. Sakai, F. Sun, K.L. Rinehart, W.W. Carmichael, W.R. Evans, P. Cruz, M.H.G. Munro, J.W. Blunt, J. Org. Chem., 1994, 59, 2349.
• [58] K. Karlsson, V. Sipiä, H. Kankaanpää, J. Meriluoto J., J. Chromatogr. B., 2003, 784, 243.
• [59] H. Mazur-Marzec, J. Meriluoto, M. Pliński, J. Szafranek, Rapid Commun. Mass Spectrom., 2006, 20, 2023.
• [60] K. Tsuji, S. Nalto, F. Kondo, N. Ishikawa, M.F. Watanabe, M. Suzuki, K.I. Harada, Environ. Sci. Technol., 1994, 28, 173.
• [61] K. Tsuji, T. Watanuki, F. Kondo, M.F. Watanabe, S. Susuki, H. Uchida, K.I. Harada, Toxicon, 1995, 32, 1619.
• [62] H. Twist, G.A. Codd, FEMS Microbiol. Lett., 1997, 151, 83.
• [63] H. Mazur-Marzec, J. Meriluoto, M. Pliński, Chemosphere, 2006, 65, 1388.
• [64] K.A. Beattie, Phytochemistry, 2000, 54, 57.
• [65] K. Saito, A. Konno, H. Ishii, H. Saito, F. Nishida, T. Abe, Ch. Chen, Nat. Prod., 2001, 64, 139.
• [66] E.D. DeSilva, D.E. Williams, R.J., Andersen, H. Klix, C.F.B. Holmes, T.M. Allen, Tetrahedron Letters, 1992, 33, 1561.
• [67] L. Spoof, S. Klimova, A. Mikhailov, J.E. Eriksson, Toxicon, 2003, 41, 153.
• [68] A. Annila, J. Lehtimaki, K. Mattila, J.E. Eriksson, K. Sivonen, T. T. Rantala, T. Drakenberg, J. Biol. Chem., 1996, 271, 16695.
• [69] K. Kononen, K. Sivonen, J. Lehtimaki, Toxicity of phytoplankton blooms in the Gulf of Finland and Gulf of Bothnia, Baltic Sea, [w:] Toxic phytoplankton blooms in the sea, T.J. Smayda & Y. Shimizu red., Elsevier Sciences Publishers B.V., 1992, 269.
• [70] H.T. Kankaanpää, V.O. Sipiä, J.S. Kuparinen, J.L. Ott, W.W. Carmichael, Phycologia, 2001, 40, 268.
• [71] J. Lehtimäki, P. Moisander, K. Sivonen, K. Kononen K., Appl. Environ. Microbiol., 1997, 63, 1647.
• [72] G.J. Jones, P.T. Orr, Wat. Res., 1994, 28, 871.
• [73] K. Lahti, J. Rapala, M. Färdig, K. Niemelä, K. Sivonen, Wat. Res., 1997, 31, 1005.
• [74] H. Mazur, M. Pliński, Oceanologia, 2001, 43, 329
• [75] K. Kaya, T. Sano, Anal. Chim. Acta., 1997, 386, 107.
• [76] I. Liu, L.A. Lawton, P.K. Robertson, Environ. Sci. Technol., 2003, 37, 3214.
• [77] I. Liu, L.A. Lawton, D.W. Bahnemann, P.K.J. Robertson, Appl. Catal. B, 2005, 60, 245.
• [78] T.P.J. Kull, P.H. Backlund, K.M. Karlsson, J.A.O. Meriluoto, Environ. Sci. Technol., 2004, 38, 6025.
• [79] G.S. Shephard, S. Stockenstrom, D. De Villiers, W.J. Engelbrecht, E.W. Sydenham, G.F.S. Wessels, Toxicon, 1998, 36, 1895.
• [80] I. Liu, L.A. Lawton, B. Cornish, P.K.J. Robertson, J. Photoch. Photobio. A, 2002, 148, 349.
• [81] D.G. Bourne, G.J. Jones, R.L. Blakeley, A. Jones, A.P. Negri, P. Riddles P., Appl. Environ. Microbiol., 1996, 62, 4086.
• [82] I.T. Cousins, D.J. Bealing, H.A. James, A. Sutton, Wat.Res., 1996, 30, 481.
• [83] H.D. Park, Y. Sasakum Y, T. Maruyama, E. Yanagisawa, A. Hiraishi, K. Kato, Environ. Toxic., 2001, 16, 337.
• [84] K. Christoffersen, S. Lyck, A. Winding, Aquat. Microb. Ecol., 2002, 27, 125.
• [85] H. Ishii, M. Nishijima, T. Abe, Wat. Res., 2004, 38, 2667.
• [86] T. Holst, N.O.G. Jorgensen, C. Jorgensen, A. Johansen A., Wat. Res., 2003, 37, 4748.
• [87] L. Ho, T. Meyn, A. Keegan, D. Hoefel, J. Brookes, C.P. Saint, G. Newcombe, Wat. Res., 2006, 40, 768.
• [88] P.S. Salomon, S. Janson, E. Graneli, Harmful Algae, 2003, 2, 261.
• [89] A. Hangstrom, F. Azam, A. Andersson, J. Wikner, Mar. Ecol. Prog. Ser, 1988, 49, 171.
• [90] A.K. Sallal, Microbios., 1994, 77, 57.
• [91] M.P. Manage, Z. Kawabata, S. Nakano, Aquat. Microb. Ecol., 2000, 22, 111.
• [92] M. Shilo, J. Bacteriol., 1970, 104, 453.
• [93] D.G. Bourne, P. Riddles, G.J. Jones, W. Smith, R.L. Blakeley, Environ. Toxic., 2001, 16, 523.
• [94] P. Hyenstrand, T. Rohrlack, K.A. Beattie, J.F. Metcalf, G.A. Codd, K. Christoffersen,Wat. Res., 2003, 37, 3299.
• [95] T. Saito, K. Okano, H.D. Park, T. Itiyama, Y. Inamori, B. Neilan, B.P. Burns, N. Sugiura, FEMS Microbiol. Lett., 2003, 229, 271.
• [96] S. Takenaka, M.F. Watanabe, Chemosphere, 1997, 34, 749.
• [97] S. Imanishi, H. Kato, M. Mizuno, K. Tsuji, K. Harada, Chem. Res. Toxicol., 2005, 18, 591.
• [98] A. M. Valeria, E.J. Ricardo, S. Plugmacher, D.A. Wunderlin, Biodegradation, 2006, 17, 447.
• [99] S. Takenaka, Chemosphere, 1998, 36, 2277.
• [100] H. Mazur-Marzec, A. Tymińska, J. Szafranek, J. Kobos, Environ. Toxicol., 2007, 22, 101-111.
• [101] K. Tsuji, M. Asakawa, Y. Anzai, T. Humino, K. Harada, Chemosphere, 2006, 65, 117.
• [102] D.G. Bourne, R.I. Blakeley, P. Riddles, G.J. Jones, Wat.Res., 2006, 40, 1294.
• [103] R.J. Morris, D.E. Williams, H.A. Luu, C.F.B. Holmes, R.J. Andersen, S.E. Calvert, Toxicon, 2000, 38, 303.
• [104] S.M. Libes, [w:] An introduction to marine biogeochemistry, John Wiley and Sons, 1992.
• [105] K. Tsuji, H. Masui, H. Uemura, Y. Mori, K. Harada, Toxicon, 2001, 39, 687.
• [106] M.J. Miller, M. M. Critchleym, J. Hutson, Fallowfield, Wat. Res., 2001, 35, 1461.
• [107] G. Grützmacher, G. Böttcher G, I. Chorus, H. Bartel, Toxicol., 2002, 17, 386.
• [108] F.J. Stevenson, Journal of Environmental Quality, 1972, 1, 333.
• [109] F. Worall, M. Fernandez-Perez, A.C. Johnson A.C., F. Flores Cesperedes, E. Gonzales Pradas E., J. Contam. Hydrol., 2001, 49, 262.
• [110] P.J. Dillon, M. Miller, A. Fallowfield, J. Hutson, J. Hydrol., 2002, 266, 209.
• [111] X Zang., J.D.H. van Heemst, K.J. Dria, P.G. Hatcher, Organic Geochemistry, 2000, 31, 679.
• [112] R.T. Nguyen, H.R. Harvey, Geochim. Cosmochim. Acta, 2001, 65, 1467.
• [113] I.R. Falconer, A. Choice, W. Hosja, Environ. Toxicol Water Qual, 1992, 7, 119.
• [114] P.G. Van Buynder, T. Oughtred, B. Kirkby, S. Phillips, G. Eaglesham, K. Thomas, M. Burch, Environ. Toxicol, 2001, 16, 468.
• [115] V.O. Sipiä, H. Kankaanpää, J. Flinkman, K. Lahti, J.A.O. Meriluoto, Environ. Toxicol., 2001, 16, 330.
• [116] V.O. Sipia, H.T. Kankaanpää, S. Pflugmacher, J. Flinkman, A. Furey, K.J. James, Ecotox. Environ. Safe., 2002, 53, 305.
• [117] H. Kankanpaa, A.K. Turnen, K. Karlsson, G. Bylund, J. Meriluoto, V. Sipia, Chemosphere, 2005, 59, 1091.
• [118] J.S. Metcalf, K.A. Beattie, S. Pflugmacher, G.A. Codd, FEMS Microbiol. Lett., 2000, 189, 155.
• [119] C. Wiegand, S. Pflugmacher, A. Oberemm, N. Meems, K.A. Beattie, C.E.W. Steinberg, G.A. Codd, Environ. Toxicol., 1999, 14, 89.
• [120] K.K. Lehtonen, H. Kankaanpää, S. Leiniö, V.O. Sipiä, S. Pflugmacher, E. Sandberg-Kilpi, Aquat. Toxicol., 2003, 64, 461.
• [121] J. Engström, M. Koski, M. Viitasalo, M. Reinikainen, S. Repka, K. Sivonen, J. Plankton Res., 2000, 22, 1403.
• [122] M. Viherluoto, H. Kuosa, J. Flinkman, M. Viitasalo, Mar. Biol., 2000, 136, 553.
• [123] P.J. Obersholter, A.M. Botha, T.E. Cloete, Harmful Algae, 2006, w druku.
• [124] W. Lampert, Ver. Int. Verein. Limnol., 1981 b, 21, 1436.
• [125] M. Karialainen, M. Reinikainen, F. Lindvall, L. Spoof, J.A.O. Meriluoto, [w:] Finish Institute of Marine Research, Finland, Helsinki, 2005, 52.
• [126] H.D. Rodger, T. Turnbull, C. Edwards, G.A. Codd, J. Fish Dis., 1994, 17, 177.
• [127] K.E. Fledmark, M. Serres, N. Larsen, T. Yasumoto, T. Aune, S. Doskeland, Toxicon, 1998, 36, 1101.
• [128] T. Wiklund, G. Bylund, BMB Publ., 1994, 15, 49.
• [129] G. Francis G., Nature, 1878, 18, 11.
• [130] L. Edler, S. Ferno, M.G. Lind, R. Lundberg, P.O. Nilsson, Ophelia, 1985, 24, 103.
• [131] S. Nehring, J. Plankton Res., 1993, 15, 867.
• [132] V.R. Beasley, A.M. Dahlem, W.O. Cook, W.M. Valentine, R.A. Lovell, S.B. Hooser, K.I. Harada, M. Suzuki, W.W. Carmichael, J.Vet.Diagn.Invest., 1989, 1, 359.
• [133] M. Tarczyńska, G. Nałęcz-Jawecki, M. Brzychcy, M. Zalewski, J. Sawicka, [w:] Persoone G, red., New Microbiotests four routine toxicity screening and biomonitoring. Kluwer Academic, New York, 2000, 527.
• [134] B. Maršálek, L. Bláha, Environ. Toxicol., 2004, 19, 310.
• [135] F.S. Chu, X. Huang, R.D. Wei, W.W. Carmichael, Appl. Environ. Microbiol., 1989, 55, 1928.
• [136] C.J. Ward, K.A. Beattie, E.Y.C. Lee, G.A. Codd, FEMS Microbiol. Lett. 1997, 153, 465.
• [137] L.A. Lawton, C. Edwards, G.A. Codd, Analyst, 1994, 119, 1525.
• [138] J. Fastner, I. Flieger, U. Neumann, Water Res., 1998, 32, 3177.
• [139] K.I. Harada, K. Matsuura, M. Suzuki, H. Oka, M.F. Watanabe, S. Oishi, A.M. Dahlem, V.R. Beasley, W.W. Carmichael, J. Chromatogr., 1988, 448, 275.
• [140] J.A.O. Meriluoto, J.E. Eriksson, J. Chromatogr., 1988, 438, 93.
• [141] S.M. Coyle, L.A. Lawton, Phycologia, 1996, 35, 57.
• [142] J.A.O. Meriluoto, Analyt. Chim. Acta, 1997, 352, 277.
• [143] T. Kusumi, M.F. Watanabe, K.I. Harada, W.W. Carmichael, H. Fujiki [wyd]: Toxic Microcystis, CRC Press, London, 1996, 149.
• [144] F. Kondo, Y. Ikai, H. Oka, N. Ishikawa, M.F. Watanabe, M. Watanabe, K.I. Harada, M. Suzuki, Toxicon, 1992, 30, 227.
• [145] L. Zhang, X. Ping, Z. Yang, Talanta, 2004, 62, 193.
• [146] M. Maizels, W. Budde, Anal. Chem., 2004, 76, 1342.
• [147] M. Welker, J. Fastner, M. Erhard, H. Döhren, Environ. Toxicol., 2002, 17, 367.
• [148] C. Edwards, L.A. Lawton, K.A. Beattie, G.A. Codd, S. Pleasance, G.J. Dear, Rapid Commun. Mass Spectrom., 1993, 7, 714.
• [149] T. Sano, K. Nohara, F. Shiraishi, K. Kaya, J. Environ. Anal. Chem., 1992, 49, 163.
• [150] K. Kaya, T. Sano, Anal. Chim. Acta., 1999, 386, 107.