Cyanobacterial toxins and toxin production

Phycologia

Volumn 35, Issue SUPPL., 1996, Pages 12-24

  Sivonen, Kaarina ^a  

^a Div Microbiol PO Box 56 B   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002613386     PISSN: 00318884     EISSN: None     Source Type: Journal    
DOI: 10.2216/i0031-8884-35-6s-12.1     Document Type: Article

References (158)

1. ANDERSEN R.J., LUU H.A., CHEN D.Z., HOLMES C.F.B., KENT M.L., LE BLANC M., TAYLOR F.J.R. & WILLIAMS D.E. 1993. Chemical and biological evidence links microcystins to salmon 'netpen liver disease'. Toxicon 31: 1315-1323.
2. ANDERSON D.M. 1994. Red tides. Scientific American August: 52-58.
3. ARMENT A.R. & CARMICHAEL W.W. 1994. Microcystin is the product of a thio-template mechanism. 37th Conference of International Association for Great Lakes Research, 5-9 June 1994, p. 102. Windsor, Ontario, Canada.
4. ARMENT A.R. & CARMICHAEL W.W. 1995. Evidence that microcystin is produced by a thio-template mechanism. Vth Cyanobacterial Molecular Biology Workshop, 21-25 July 1995, p. 97. Asilomar, CA, USA.
5. AZAVEDO S.M.F.O., EVANS W.R., CARMICHAEL W.W. & NAMIKOSHI M. 1994. First report of microcystins from a Brazilian isolate of the cyanobacterium Microcystis aeruginosa. Journal of Applied Phycology 6: 261-265.
6. BAKER P.D. & HUMPAGE A.R. 1994. Toxicity associated with commonly occurring cyanobacteria in surface waters of the Murray-Darling basin Australia. Australian Journal of Marine and Freshwater Research 45: 773-786.
7. BEASLEY V.R., DAHLEM A.M., COOK W.O., VALENTINE W.M., LOWELL R.A., HOOSER S.B., HARADA K.-I., SUZUKI M. & CARMICHAEL W.W. 1989. Diagnostic and clinically important aspects of cyanobacterial (blue-green algae) toxicoses. Journal of Veterinary Diagnostic and Investigation 1: 359-365.
8. BOLAND M.P., SMILLIE M.A., CHEN D.Z.X. & HOLMES C.F.B. 1993. A unified bioscreen for the detection of diarrhetic shellfish toxins and microcystins in marine and freshwater environments. Toxicon 31: 1393-1405.
9. BOTES D.P., TUINMAN A.A., WESSELS P.L., VILJOEN C.C. & KRUGER H. 1984. The structure of cyanoginosin-LA, a cyclic heptapeptide toxin from the cyanobacterium Microcystis aeruginosa. Journal of the Chemical Society, Perkin Transactions 1: 2311-2318.
10. BOTES D.P., WESSELS P.L., KRUGER H., RUNNEGAR M.T.C., SANTIKARN S., SMITH R.J., BARNA J.C.J. & WILLIAMS D.H. 1985. Structural studies on cyanoginosins-LR, -YR, -YA, and -YM, peptide toxins from Microcystis aeruginosa. Journal of the Chemical Society, Perkin Transactions 1: 2747-2748.
11. BRUNO M., BARBINI D.A., PIERDOMINICI E., SERSE A.P. & IOPPOLO A. 1994. Anatoxin-a and previously unknown toxin in Anabaena planctonica from blooms found in Lake Mulargia (Italy). Toxicon 32: 369-373.
12. CARDELLINA II J.H., MARNER F.-J. & MOORE R.E. 1979. Seaweed dermatitis: structure of lyngbyatoxin A. Science 204: 193-195.
13. CARMICHAEL W.W. 1986. Algal toxins. In: Advances in Botanical Research, Vol. 12 (Ed. by J.R. Callow), pp. 47-101. Academic Press, London.
14. CARMICHAEL W.W. 1992a. Cyanobacteria secondary metabolites - cyanotoxins. Journal of Applied Bacteriology 72: 445-459.
15. CARMICHAEL W.W. 1992b. A status report on planktonic cyanobacteria (blue-green algae) and their toxins. United States Environmental Protection Agency, EPA/600/R-92/079. Office of Research and Development, Washington, DC. 141 pp.
16. CARMICHAEL W.W. 1994. The toxins of cyanobacteria. Scientific American January: 64-72.
17. CARMICHAEL W.W., BEASLEY V.R., BUNNER D.L., ELOFF J.N., FALCONER I., GORHAM P., HARADA K.-I., KRISHNAMURTHY T., YU M.-J., MOORE R.E., RINEHART K., RUNNEGAR M., SKULBERG O.M. & WATANABE M. 1988a. Naming of cyclic heptapeptide toxins of cyanobacteria (blue-green algae). Toxicon 26: 971-973.
18. CARMICHAEL W.W., BIGGS D.F. & GORHAM P.R. 1975. Toxicology and pharmacological action of Anabaena flos-aquae toxin. Science 187: 542-544.
19. CARMICHAEL W.W., BIGGS D.F. & PETERSON M.A. 1979. Pharmacology of anatoxin-a, produced by the freshwater cyanophyte Anabaena flos-aquae NCR-44-1. Toxicon 17: 229-236.
20. CARMICHAEL W.W., ESCHEDOR J.T., PATTERSON G.M.L. & MOORE R.E. 1988b. Toxicity and partial structure of a hepatotoxic peptide produced by the cyanobacterium Nodularia spumigena Mertens emend. L575 from New Zealand. Applied and Environmental Microbiology 54: 2257-2263.
21. CARMICHAEL W.W., EVANS W.R., YIN Q.-Q., BELL P. & MOCAUKLOWSKI E. 1995. Evidence for paralytic shellfish poisons in the mat forming cyanobacteria Lyngbya wollei (nov. comb.). VII International Conference on Toxic Phytoplankton, 12-16 July 1995. Sendai, Japan.
22. CARMICHAEL W.W. & FALCONER I.R. 1993. Diseases related to freshwater blue-green algal toxins, and control measures. In: Algal Toxins in Seafood and Drinking Water (Ed. by I.R. Falconer), pp. 187-209. Academic Press, London.
23. CARMICHAEL W.W., MAHMOOD N.A. & HYDE E.G. 1990. Natural toxins from cyanobacteria (blue-green algae). In: Marine Toxins: Origin, Structure and Molecular Pharmacology, Vol. 418 (Ed. by S. Hall & G. Strichartz), pp. 87-106. American Chemical Society, Washington, DC.
24. CARMICHAEL W.W., YU M.-J., HE Z.-R., HE J.-W. & YU J.-L. 1988c. Occurrence of the toxic cyanobacterium (blue-green alga) Microcystis aeruginosa in Central China. Archiv für Hydrobiologie 114: 21-30.
25. CHEN D.Z.X., BOLAND M.P., SMILLIE M.A., KLIX H., PTAK C., ANDERSEN R.J. & HOLMES C.F.B. 1993. Identification of protein phosphatase inhibitors of the microcystin class in the marine environment. Toxicon 31: 1407-1414.
26. CHOI B.W., NAMIKOSHI M., SUN E, RINEHART K.L., CARMICHAEL W.W., KAUP A.M., EVANS W.R. & BEASLEY V.R. 1993. Isolation of linear peptides related to the hepatotoxins nodularin and microcystins. Tetrahedron Letters 34: 7881-7884.
27. CODD G.A. & POON G.K. 1988. Cyanobacterial toxins. In: Proceedings of the Phytochemical Society of Europe, Vol. 28 (Ed. by L.J. Rogers & J.G. Gallon), pp. 283-296. Oxford University Press, Oxford.
28. COOK W.O., BEASLEY V.R., LOWELL R.A., DAHLEM A.M. & CARMICHAEL W.W. 1989. Consistent inhibition of peripheral cholinesterases by neurotoxins from the freshwater cyanobacterium Anabaena flos-aquae: studies of ducks, swine, mice and a steer. Environmental Toxicology and Chemistry 8: 915-922.
29. CRAIG M., MCCREADY L., LUU H.A., SMILLIE M.A., DUBORD P. & HOLMES C.F.B. 1993. Identification and characterization of hydrophobic microcystins in Canadian freshwater cyanobacteria. Toxicon 31: 1541-1549.
30. CREMER J. & HENNING K. 1991. Application of reversed-phase medium-pressure liquid chromatography to the isolation, separation and amino acid analysis of two closely related peptide toxins of the cyanobacterium Microcystis aeruginosa strain PCC 7806. Journal of Chromatography 587: 71-80.
31. DE SILVA E.D., WILLIAMS D.E., ANDERSEN R.J., KLIX H., HOLMES C.F.B. & ALLEN T.M. 1992. Motuporin, a potent protein phosphatase inhibitor isolated from the Papua New Guinea sponge Theonella swinhoei Gray. Tetrahedron Letters 33: 1561-1564.
32. DEVLIN J.P., EDWARDS O.E., GORHAM P.R., HUNTER M.R., PIKE R.K. & STAVRIC B. 1977. Anatoxin-a, a toxic alkaloid from Anabaena flos-aquae NCR-44h. Canadian Journal of Chemistry 55: 1367-1371.
33. DITTMAN E., MEIßNER K. & BÖRNER T. 1995. Analyses of DNA sequences encoding peptide synthetases in Microcystis aeruginosa. Third European Workshop on the Molecular Biology of Cyanobacteria, 12-14 May 1995, p. 35 Sevilla, Spain.
34. EDWARDS C., BEATTIE K.A., SCRIMGEOUR C.M. & CODD G.A. 1992. Identification of anatoxin-a in benthic cyanobacteria (blue-green algae) and in associated dog poisonings at Loch Insh, Scotland. Toxicon 30: 1165-1175.
35. ENDEAN R., MONKS S.A., GRIFFITH J.K. & LLEWELLYN L.E. 1993. Apparent relationship between toxins elaborated by the cyanobacterium Trichodesmium erythraeum and those present in the flesh of the narrow-barred Spanish mackerel Scomberomorus commersoni. Toxicon 31: 1155-1165.
36. ENTZEROTH M., BLACKMAN A.J., MYNDERSE J.S. & MOORE R.E. 1985. Structures and stereochemistries of oscillatoxin B, 31-noroscillatoxin B, oscillatoxin D, and 30-methyloscillatoxin D. Journal of Organic Chemistry 50: 1255-1259.
37. ERIKSSON J.E. & GOLDMAN R.D. 1993. Protein phosphatase inhibitors alter cytoskeletal structure and cellular morphology. Advances in Protein Phosphatases 7: 335-357.
38. ERIKSSON J.E., TOIVOLA D., MERILUOTO J.A.O., KARAKI H., HAN Y.-G. & HARTSHORNE D. 1990. Hepatocyte deformation induced by cyanobacterial toxins reflects inhibition of protein phosphatases. Biochemical and Biophysical Research Communications 173: 1347-1353.
39. FALCONER I.R. & BUCKLEY T.H. 1989. Tumour promotion by Microcystis sp., a blue-green alga occurring in water supplies. Medical Journal of Australia 150: 351.
40. FALCONER I.R. & YEUNG D.S.K. 1992. Cytoskeletal changes in hepatocytes induced by Microcystis toxins and their relation to hyperphosphorylation of cell proteins. Chemical and Biological Interactions 81: 181-196.
41. FERREIRA E, FRANCO J.M., FIDALGO M.L. & FERNANDEZ-VILA P. 1995. Detection of PSP toxins from Aphanizomenon flos-aquae (cyanobacteria) collected in the Crestuma/Lever reservoir (Duro River, Northern Portugal). Symposium Eutrophication, Causes, Consequences and Remediation, 21-23 May 1995, p. 24. Porto, Portugal.
42. FRANCIS G. 1878. Poisonous Australian lake. Nature 18: 11-12.
43. FUJII K., HARADA K.-I., SUZUKI M., KONDO F., IKAI Y., OKA H., CARMICHAEL W.W. & SIVONEN K. 1996. Occurrence of novel cyclic peptides together with microcystins from toxic cyanobacteria, Anabaena species. In: Harmful and Toxic Algal Blooms (Ed. by T. Yasumoto, Y. Oshima & Y. Fukuyo), pp. 559-562. Intergovernmental Oceanographic Commission of UNESCO, Paris.
44. FUJIKI H., SUGANUMA M., SUGURI H., YOSHIZAWA S., TAKAGI K., NAKAYASU M., OJIKA M., YAMADA K., YASUMOTO T., MOORE R.E. & SUGIMURA T. 1990. New tumor promoters from marine natural products. In: Marine Toxins: Origin, Structure and Molecular Pharmacology, Vol. 418 (Ed. by S. Hall & G. Strichartz), pp. 232-240. American Chemical Society, Washington, DC.
45. GALLON J.R., CHIT K.N. & BROWN E.G. 1990. Biosynthesis of the tropane-related cyanobacterial toxin anatoxin-a: role of ornithine decarboxylase. Phytochemistry 29: 1107-1111.
46. GALLON J.R., KITTAKOOP P. & BROWN E.G. 1994. Biosynthesis of anatoxin-a by Anabaena flos-aquae: examination of primary enzymic steps. Phytochemistry 35: 1195-1203.
47. GATHERCOLE P.S. & THIEL P.G. 1987. Liquid chromatographic determination of the cyanoginosins, toxins produced by the cyanobacterium Microcystis aeruginosa. Journal of Chromatography 408: 435-440.
48. GENTILE J.H. & MALONEY T.E. 1969. Toxicity and environmental requirements of a strain of Aphanizomenon flos-aquae (L.) Ralfs. Canadian Journal of Microbiology 15: 165-173.
49. HAHN S.T. & CAPRA M.F. 1992. The cyanobacterium Oscillatoria erythraea - a potential source of toxin in the ciguatera food-chain. Food Additives and Contaminants 9: 351-355.
50. HARADA K.-I., MATSUURA K., SUZUKI M., WATANABE M.F., OISHI S., DAHLEM A.M., BEASLEY V.R. & CARMICHAEL W.W. 1990b. Isolation and characterization of the minor components associated with microcystins LR and RR in the cyanobacteria (blue-green algae). Toxicon 28: 55-64.
51. HARADA K.-I., MAYUMI T., SHIMADA T., SUZUKI M., KONDO F. & WATANABE M.F. 1993. Occurrence of four depsipeptides, aeruginopeptins, together with microcystins from toxic cyanobacteria. Tetrahedron Letters 34: 6091-6094.
52. HARADA K.-I., OGAWA K., KIMURA Y., MURATA H., SUZUKI M., THORN P.M., EVANS W.R. & CARMICHAEL, W.W. 1991a. Microcystins from Anabaena flos-aquae NRC 525-17. Chemical Research in Toxicology 4: 535-540.
53. HARADA, K.-I., OGAWA K., MATSUURA K., MURATA H., SUZUKI M., WATANABE M.F., ITEZONO Y. & NAKAYAMA N. 1990a. Structural determination of geometrical isomers of microcystins LR and RR from cyanobacteria by two-dimensional NMR spectroscopic techniques. Chemical Research in Toxicology 3: 473-481.
54. HARADA K.-I., OGAWA K., MATSUURA K., NAGAI H., MURATA H., SUZUKI M., ITEZONO Y., NAKAYMA N., SHIRAI M. & NAKANO M. 1991b. Isolation of two toxic heptapeptide microcystins from an axenic strain of Microcystis aeruginosa, K-139. Toxicon 29: 479-489.
55. HARADA K.-I., OHTANI I., IWAMOTO K., SUZUKI M., WATANABE M.F., WATANABE M. & TERAO K. 1994. Isolation of cylindrospermopsin from a cyanobacterium Umezakia natans and its screening method. Toxicon 32: 73-84.
56. HASHIMOTO Y., KAMIYA H., YAMAZATO K. & NOZAWA K. 1976. Occurrence of a toxic blue-green alga inducing skin dermatitis in Okinawa. In: Animal, Plant, and Microbial Toxins, Vol. 1 (Ed. by A. Ohsaka, K. Hayashi & Y. Sawai), pp. 333-338. Plenum Publishing, New York.
57. HAWKINS P.R., RUNNEGAR M.T.C., JACKSON A.R.B. & FALCONER I.R. 1985. Severe hepatotoxicity caused by the tropical cyanobacterium (blue-green alga) Cylindrospermopsis raciborskii (Woloszynska) Seenaya and Subba Raju isolated from a domestic water supply reservoir. Applied and Environmental Microbiology 50: 1292-1295.
58. HAWSER S.P., CODD G.A., CARPENTER E.J. & CAPONE D.G. 1992. A neurotoxic factor associated with the bloom-forming cyanobacterium Trichodesmium. Toxicon 29: 277-278.
59. HEMSCHEIDT T., BURGOYNE D.L. & MOORE R.E. 1995a. Biosynthesis of anatoxin-a(s), (2S,4S)-4-hydroxyarginine as an intermediate. Chemical Communications 205-206.
60. HEMSCHEIDT T., RAPALA J., SIVONEN K. & SKULBERG O.M. 1995b. Biosynthesis of anatoxin-a in Anabaena flos-aquae and homoanatoxin-a in Oscillatoria formosa. Chemical Communications 1361-1362.
61. HENRIKSEN P., KAAS H., DAMSØ L. & MOESTRUP Ø. 1995. Toxic cyanobacteria (blue-green algae) in Danish fresh waters. 1st International Congress on Toxic Cyanobacteria (Blue-Green Algae), 20-24 August 1995. Rønne, Denmark (poster).
62. HONKANEN R.E., CODISPOTI B.A., TSE K. & BOYNTON A.L. 1994. Characterization of natural toxins with inhibitory activity against serine/threonine protein phosphatases. Toxicon 32: 339-350.
63. HONKANEN R.E., ZWILLERS J., MOORE R.E., DAILY S.L., KHATRA B.S., DUKELOW M. & BOYNTON A.L. 1990. Characterization of microcystin-LR, a potent inhibitor of type 1 and type 2A protein phosphatases. The Journal of Biological Chemistry 265: 19401-19404.
64. HUBER C.S. 1972. The crystal structure and absolute configuration of 2,9-diacetyl-9-azabicyclo(4,2,1 )non-2,3-ene. Acta Crystallographica. Section B 28: 2577-2582.
65. HUMPAGE A.R., ROSITANO J., BRETAG A.H., BROWN R., BALER P.D., NICHOLSON B.C. & STEFFENSEN D.A. 1994. Paralytic shellfish poisons from Australian cyanobacterial blooms. Australian Journal of Marine and Freshwater Research 45: 761-771.
66. IKAWA M., WEGENER K., FOXALL T.L. & SASNER J.J. JR. 1982. Comparizon of the toxins of the blue-green alga Aphanizomenon flos-aquae with the Gonyaulax toxins. Toxicon 20: 747-752.
67. JACKIM E. & GENTILE J. 1968. Toxins of a blue-green alga: similarity to saxitoxin. Science 162: 915-916.
68. JACOBS D., BASS R.A. & NEILAN B.A. 1995. Isolation and characterization of candidate genes responsible for toxins biosynthesis in cyanobacteria. Vth Cyanobacterial Molecular Biology Workshop, 21-25 July 1995, p. 98. Asilomar, CA, USA.
69. JONES G.J., BLACKBURN S.I. & PARKER N.S. 1994. A toxic bloom of Nodularia spumigena Mertens in Orielton Lagoon, Tasmania. Australian Journal of Marine and Freshwater Research 45: 787-800.
70. KAYA K. & WATANABE M.M. 1990. Microcystin composition of an axenic clonal strain of Microcystis viridis and Microcystis viridis - containing waterblooms in Japanese freshwaters. Journal of Applied Phycology 2: 173-178.
71. KIVIRANTA J., NAMIKOSHI M., SIVONEN K., EVANS W.R., CARMICHAEL W.W. & RINEHART K.L. 1992. Structure determination and toxicity of a new microcystin from Microcystis aeruginosa strain 205. Taxicon 30: 1093-1098.
72. KLEINKAUF H. & VON DÖHREN H. 1990. Nonribosomal biosynthesis of peptide antibiotics. Review. European Journal of Biochemistry 192: 1-15.
73. KLEINKAUF H. & VON DÖHREN H. 1995. The nonribosomal peptide biosynthetic system - on the origins of structural diversity of peptides, cyclopeptides and related compounds. Antonie van Leeuwenhoek 67: 229-241.
74. KRISHNAMURTHY T., SZAFRANIEC L., HUNT D.F., SHABANOWITZ J., YATES J.R., HAUER C.R., CARMICHAEL W.W., SKULBERG O., CODD G.A. & MISSLER S. 1989. Structural characterization of toxic cyclic peptides from blue-green algae by tandem mass spectrometry. Proceedings of the National Academy of Sciences USA 86: 770-774.
75. KUSUMI T., OOI T., WATANABE M.M., TAKAHASHI H. & KAKISAWA H. 1987. Cyanoviridin RR, a toxin from the cyanobacterium (blue-green alga) Microcystis viridis. Tetrahedron Letters 28: 4695-4698.
76. LANARAS T. & COOK C.M. 1994. Toxin extraction from an Anabaenopsis milleri-dominated bloom. The Science of the Total Environment 142: 163-169.
77. LEHTIMÄKI J., MOISANDER P., SIVONEN K. & KONONEN K. 1995. Comparison of growth, toxin production and nitrogen fixation of cyanobacteria from the Baltic Sea. 1st International Congress on Toxic Cyanobacteria (Blue-Green Algae), 20-24 August 1995, p. 59. Rønne, Denmark.
78. LEHTIMÄKI J., SIVONEN K., LUUKKAINEN R. & NIEMELÄ S.I. 1994. The effects of incubation time, temperature, light, salinity and phosphorus on growth and hepatotoxin production by Nodularia strains. Archiv für Hydrobiologie 130: 269-282.
79. LUKAC M. & AEGERTER R. 1993. Influence of trace metals on growth and toxin production of Microcystis aeruginosa. Toxicon 31: 293-305.
80. LUUKKAINEN R., NAMIKOSHI M., SIVONEN K., RINEHART K.L. & NIEMELÄ S.I. 1994. Isolation and identification of 12 microcystins from four strains and two bloom samples of Microcystis spp.: structure of a new hepatotoxin. Toxicon 32: 133-139.
81. LUUKKAINEN R., SIVONEN K., NAMIKOSHI M., FÄRDIG M., RINEHART K.L. & NIEMELÄ S.I. 1993. Isolation and identification of eight microcystins from 13 Oscillatoria agardhii strains: structure of a new microcystin. Applied and Environmental Microbiology 59: 2204-2209.
82. MACKINTOSH C., BEATTIE K.A., KLUMPP S., COHEN P. & CODD G.A. 1990. Cyanobacterial microcystin-LR is a potent and specific inhibitor of protein phosphatases 1 and 2A from both mammals and higher plants. FEBS Letters 264: 187-192.
83. MAHMOOD N.A. & CARMICHAEL W.W. 1986. Paralytic shellfish poisons produced by the freshwater cyanobacterium Aphanizomenon flos-aquae NH-5. Toxicon 24: 175-186.
84. MAHMOOD N.A. & CARMICHAEL W.W. 1987. Anatoxin-a(S), an anticholinesterase from the cyanobacterium Anabaena flos-aquae NCR-525-17. Toxicon 25: 1221-1227.
85. MAHMOOD N.A., CARMICHAEL W.W. & PFAHLER D. 1988. Anticholinesterase poisonings in dogs from a cyanobacterial (blue-green algae) bloom dominated by Anabaena flos-aquae. American Journal of Veterinary Research 49: 500-503.
86. MATSUNAGA S., MOORE R.E., NIEMCZURA W.P. & CARMICHAEL W.W. 1989. Anatoxin-a(S), a potent anticholinesterase from Anabaena flos-aquae. Journal of the American Chemical Society 111: 8021-8023.
87. MATSUSHIMA R., YOSHIZAWA S., WATANABE M.F., HARADA K.-I., FURUSAWA M., CARMICHAEL W.W. & FUJIKI H. 1990. In vitro and in vivo effects of protein phosphatase inhibitors, microcystin and nodularin, on mouse skin and fibroblasts. Biochemical and Biophysical Research Communications 171: 867-874.
88. MEIßNER K., DITTMAN E. & BÖRNER T. 1996. Toxic and nontoxic strains of the cyanobacterium Microcystis aeruginosa contain sequences homologous to peptide synthetase genes. FEMS Microbiology Letters 35: 295-303.
89. MERILUOTO J.A.O., SANDSTRÖM A., ERIKSSON J.E., REMAUD G., GREY CRAIG A. & CHATTOPADHYAYA J. 1989. Structure and toxicity of a peptide hepatotoxin from the cyanobacterium Oscillatoria agardhii. Toxicon 27: 1021-1034.
90. MOIKEHA S.N. & CHU G.W. 1971. Dermatitis-producing alga Lyngbya majuscula Gomont in Hawaii. II. Biological properties of the toxic factor. Journal of Phycology 7: 8-13.
91. MOORE R.E., CHEN J.L., MOORE B.S., PATTERSON G.M.L. & CARMICHAEL W.W. 1991. Biosynthesis of microcystin-LR. Origin of the carbons in the Adda and Masp units. Journal of the American Chemical Society 113: 5083-5084.
92. MOORE B.S., OHTANI I., DE KONING C.B., MOORE R.E. & CARMICHAEL W.W. 1992. Biosynthesis of anatoxin-a(s). Origin of the carbons. Tetrahedron Letters 33: 6595-6598.
93. MOORE R.E., OHTANI I., MOORE B.S., DE KONING C.B., YOSHIDA W.Y., RUNNEGAR M.T.C. & CARMICHAEL W.W. 1993. Cyanobacterial toxins. Gazzetta Chimica Italiana 123: 329-336.
94. MYNDERSE J.S., MOORE R.E., KASHIWAGI M. & NORTON T.R. 1977. Antileukemia activity in the Oscillatoriaceae: isolation of debromoaplysiatoxin from Lyngbya. Science 196: 538-540.
95. NAMIKOSHI M., CHOI B.W., SAKAI R., SUN F., RINEHART K.L., CARMICHAEL W.W., EVANS W.R., CRUZ P., MUNRO, M.H.G. & BLUNT J.W. 1994. New nodularins: a general method for structure assignment. Journal of Organic Chemistry 59: 2349-2357.
96. NAMIKOSHI M., CHOI B.W., SUN E, RINEHART K.L., CARMICHAEL W.W., EVANS W.R. & BEASLEY V.R. 1995. Seven more microcystins from Homer Lake cells: application of the general method for structure assignment of peptides containing α,β-dehydroamino acid unit(s). Journal of Organic Chemistry 60: 3671-3679.
97. NAMIKOSHI M., RINEHART K.L., SAKAI R., SIVONEN K. & CARMICHAEL W.W. 1990. Structures of three new cyclic hepatotoxins produced by the cyanobacterium (blue-green alga) Nostoc sp. strain 152. Journal of Organic Chemistry 55: 6135-6139.
98. NAMIKOSHI M., RINEHART K.L., SAKAI R., STOTTS R.R., DAHLEM A.M., BEASLEY V.R., CARMICHAEL W.W. & EVANS W.R. 1992a. Identification of 12 hepatotoxins from a Homer lake bloom of the cyanobacteria Microcystis aeruginosa, Microcystis viridis, Microcystis wesenbergii; nine new microcystins. Journal of Organic Chemistry 57: 866-872.
99. NAMIKOSHI M., SIVONEN K., EVANS W.R., CARMICHAEL W.W., ROUHIAINEN L., LUUKKAINEN R. & RINEHART K.L. 1992b. Structures of three new homotyrosine-containing microcystins and a new homophenylalanine variant from Anabaena sp. strain 66. Chemical Research in Toxicology 5: 661-666.
100. NAMIKOSHI M., SIVONEN K., EVANS W.R., CARMICHAEL W.W., SUN F., ROUHIAINEN L., LUUKKAINEN R. & RINEHART K.L. 1992c. Two new L-serine variants of microcystins-LR and -RR from Anabaena sp. strain 202 A1 and 202 A2. Toxicon 30: 1457-1464.
101. NAMIKOSHI M., SIVONEN K., EVANS W.R., SUN F., CARMICHAEL W.W. & RINEHART K.L. 1992d. Isolation and structures of microcystins from a cyanobacterial water bloom (Finland). Toxicon 30: 1473-1479.
102. NEGRI A.P. & JONES G.J. 1995. Bioaccumulation of paralytic shellfish poisoning (PSP) toxins from the cyanobacterium Anabaena circinalis by the freshwater mussel Alathyria condola. Toxicon 33: 667-678.
103. NEILAN B.A. 1995. Identification and phylogenetic analysis of toxigenic cyanobacteria by multiplex randomly amplified polymorphic DNA PCR. Applied and Environmental Microbiology 61: 2286-2291.
104. NEILAN B.A., HAWKINS P.R., COX P.T. & GOODMAN A.E. 1994. Towards a molecular taxonomy for the bloom-forming cyanobacteria. Australian Journal of Marine and Freshwater Research 45: 869-873.
105. NEILAN B.A., JACOBS D. & GOODMAN A.E. 1995. Genetic diversity and phylogeny of toxic cyanobacteria determined by DNA polymorphisms within the phycocyanin locus. Applied and Environmental Microbiology 61: 3875-3883.
106. NISHIWAKI-MATSUSHIMA R., OHTA T., NISHIWAKI S., SUGANUMA M., KOHYAMA K., ISHIKAWA T., CARMICHAEL W.W. & FUJIKI H. 1992. Liver tumor promotion by the cyanobacterial cyclic peptide toxin microcystin-LR. Journal of Cancer Research and Clinical Oncology 118: 420-424.
107. OHTA T., SUEOKA E., IIDA N., KOMORI A., SUGANUMA M., NISHIWAKI R., TATEMATSU M., KIM S.-J., CARMICHAEL W.W. & FUJIKI H. 1994. Nodularin, a potent inhibitor of protein phosphatases 1 and 2A, is a new environmental carcinogen in male F344 rat liver. Cancer Research 54: 6402-6406.
108. OHTANI I., MOORE R.E. & RUNNEGAR M.T.C. 1992. Cylindrospermopsin: a potent hepatotoxin from the blue-green alga Cylindrospermopsis raciborskii. Journal of the American Chemical Society 114: 7941-7942.
109. PAINULY P., PEREZ R., FUKAI T. & SHIMIZU Y. 1988. The structure of a cyclic peptide toxin, cyanogenosin-RR from Microcystis aeruginosa. Tetrahedron Letters 29: 11-14.
110. PARK H.-D., WATANABE M.F., HARADA K.-I., NAGAI H., SUZUKI M., WATANABE M. & HAYASHI H. 1993. Hepatotoxin (microcystin) and neurotoxin (anatoxin-a) contained in natural blooms and strains of cyanobacteria from Japanese freshwaters. Natural Toxins 1: 353-360.
111. PATTERSON G.M.L., LARSEN L.K. & MOORE R.E. 1994. Bioactive natural products from blue-green algae. Journal of Applied Phycology 6: 151-157.
112. PEARSON M.J. 1990. Toxic blue-green algae. Report of the National Rivers Authority, Water Quality Series, No. 2, United Kingdom, Rushden, northouts, Stanley L. Hunt.
113. PRINSEP M.R., CAPLAN F.R., MOORE R.E., PATTERSON G.M.L., HONKANEN R.E. & BOYNTON A.L. 1992. Microcystin-LA from a blue-green alga belonging to the Stigonematales. Phytochemistry 31: 1247-1248.
114. RAPALA J., SIVONEN K., LUUKKAINEN R. & NIEMELÄ S.I. 1993. Anatoxin-a concentration in Anabaena and Aphanizomenon at different environmental conditions and comparison of growth by toxic and non-toxic Anabaena strains - a laboratory study. Journal of Applied Phycology 5: 581-591.
115. RAPALA J., SIVONEN K. & NIEMELÄ S.I. 1995. Comparison of toxin production by hepatotoxic and neurotoxic Anabaena spp. 1st International Congress on Toxic Cyanobacteria (Blue-Green Algae), 20-24 August 1995, p. 54. Rønne, Denmark.
116. REPAVICH W.M., SONZOGNI W.C., STANDRIDGE J.H., WEDEPOHL R.E. & MEISNER L.F. 1990. Cyanobacteria (blue-green algae) in Wisconsin waters: acute and chronic toxicity. Water Research 24: 225-231.
117. RESSOM R., SOONG F.S., FITZGERALD J., TURCZYNOWICZ L., SAADI O.E., RODER D., MAYNARD T. & FALCONER I. 1994. Health Effects of Toxic Cyanobacteria (Blue-Green Algae), pp. 108. National Health and Medical Research Council. The Australian Government Publishing Service, Canberra, Australia.
118. RINEHART K.L., HARADA K.-I., NAMIKOSHI M., CHEN C., HARVIS C.A., MUNRO M.H.G., BLUNT J.W., MULLIGAN P.E., BEASLEY V.R., DAHLEM A.M. & CARMICHAEL W.W. 1988. Nodularin, microcystin, and the configuration of Adda. Journal of the American Chemical Society 110: 8557-8558.
119. RINEHART K.L., NAMIKOSHI M. & CHOI B.W. 1994. Structure and biosynthesis of toxins from blue green algae (cyanobacteria). Journal of Applied Phycology 6: 159-176.
120. ROUHIAINEN L., BUIKEMA W, PAULIN L., FONSTEIN M., SIVONEN K. & HASELKORN R. 1994. Peptide synthetase genes from hepatotoxin producing cyanobacteria. VIII International Symposium on Phototrophic Prokaryotes, 10-15 September 1994, p. 26. Urbino, Italy.
121. ROUHIAINEN L., SIVONEN K., BUIKEMA W. & HASELKORN R. 1995. Characterization of toxin-producing cyanobacteria by using an oligonucletide probe containing a tandemly repeated heptamer. Journal of Bacteriology 177: 6021-6026.
122. RUNNEGAR M.T. & FALCONER I. 1982. The in vivo and in vitro biological effects of the peptide hepatotoxin from the blue-green alga Microcystis aeruginosa. South African Journal of Science 78: 363-366.
123. RUNNEGAR M.T., KONG S. & BERNDT N. 1993. Protein phosphatase inhibition and in vivo hepatotoxicity of microcystins. American Journal of Physiology 265: 224-230.
124. RUNNEGAR M.T., KONG S., ZHONG Y.-Z., GE, J.-L. & LU S.C. 1994. The role of glutathione in the toxicity of a novel cyanobacterial alkaloid cylindrospermopsin in cultured rat hepatocytes. Biochemical and Biophysical Research Communications 201: 235-241.
125. RUNNEGAR M.T., KONG S., ZHONG Y.-Z. & LU S.C. 1995. Inhibition of reduced glutathione synthesis by cyanobacterial alkaloid cylindrospermopsin in cultured rat hepatocytes. Biochemical Pharmacology 49: 219-225.
126. SASNER J.J. JR., IKAWA M. & FOXALL T.L. 1984. Studies on Aphanizomenon and Microcystis toxins. In: Seafood Toxins (Ed. by E.P. Regelis), pp. 391-406. ASC Symposium Series, No. 262. American Chemical Society, Washington, DC.
127. SCHWABE W, WEIHE A., BÖRNER T., HENNING M. & KOHL J.-G. 1988. Plasmids in toxic and nontoxic strains of the cyanobacterium Microcystis aeruginosa. Current Microbiology 17: 133-137.
128. SCOTT W.E. 1991. Occurrence and significance of toxic cyanobacteria in Southern Africa. Water Sciences and Technology 23: 175-180.
129. SHIMIZU Y. 1986. Toxigenesis and biosynthesis of saxitoxin analogues. Pure Applied Chemistry 58: 257-262.
130. SHIMIZU Y., NORTE M., HORI A., GENENAH A. & KOBAYASHI M. 1984. Biosynthesis of saxitoxin analogues: the unexpected pathway. Journal of the American Chemical Society 106: 6433-6434.
131. SIMS J.K. & ZANDEE VAN RILLAND R.D. 1981. Escharotic stomatitis caused by the "stinging seaweed" Microcoleus lyngbyaceus (formerly Lyngbya majuscula). Case report and literature review. Hawaii Medical Journal 40: 243-248.
132. SIVONEN K. 1990a. Effects of light, temperature, nitrate, orthophosphate, and bacteria on growth of and hepatotoxin production by Oscillatoria agardhii strains. Applied and Environmental Microbiology 56: 2658-2666.
133. SIVONEN K. 1990b. Toxic cyanobacteria in Finnish fresh waters and the Baltic Sea. Reports from Department of Microbiology. University of Helsinki. 39/1990. Hakapaino, Helsinki. 87 pp.
134. SIVONEN K., CARMICHAEL W.W., NAMIKOSHI M., RINEHART K.L., DAHLEM A.M. & NIEMELÄ S.I. 1990. Isolation and characterization of hepatotoxic microcystin homologs from the filamentous freshwater cyanobacterium Nostoc sp. strain 152. Applied and Environmental Microbiology 56: 2650-2657.
135. SIVONEN K., HIMBERG K., LUUKKAINEN R., NIEMELÄ S.I., POON G.K. & CODD G.A. 1989a. Preliminary characterization of neurotoxic blooms and strains from Finland. Toxicity Assessment 4: 339-352.
136. SIVONEN K., KONONEN K., CARMICHAEL W.W., DAHLEM A.M., RINEHART K.L., KIVIRANTA J. & NIEMELÄ S.I. 1989b. Occurrence of the hepatotoxic cyanobacterium Nodularia spumigena in the Baltic Sea and the structure of the toxin. Applied and Environmental Microbiology 55: 1990-1995.
137. SIVONEN K., NAMIKOSHI M., EVANS W.R., CARMICHAEL W.W., SUN F., ROUHIAINEN L., LUUKKAINEN R. & RINEHART K.L. 1992a. Isolation and characterization of a variety of microcystins from seven strains of the cyanobacterial genus Anabaena. Applied and Environmental Microbiology 58: 2495-2500.
138. SIVONEN K., NAMIKOSHI M., EVANS W.R., FÄRDIG M., CARMICHAEL W.W. & RINEHART K.L. 1992b. Three new microcystins, cyclic heptapeptide hepatotoxins, from Nostoc sp. strain 152. Chemical Research in Toxicology 5: 464-469.
139. SIVONEN K., NAMIKOSHI M., EVANS W.R., GROMOV B.V., CARMICHAEL W.W. & RINEHART K.L. 1992c. Isolation and structures of five microcystins from a Russian Microcystis aeruginosa strain CALU 972. Toxicon 30: 1481-1485.
140. SIVONEN K., NAMIKOSHI M., LUUKKAINEN R., FÄRDIG M., ROUHIAINEN L., EVANS W.R., CARMICHAEL W.W., RINEHART K.L. & NIEMELÄ S.I. 1995. Variation of cyanobacterial hepatotoxins in Finland. In: The Contaminants in the Nordic Ecosystem: Dynamics, Processes & Fate, Ecovision World Monograph Series (Ed. by M. Munawar & M. Luotola), pp. 163-169. SPB Academic Publishing, Amsterdam.
141. SIVONEN K., SKULBERG O.M., NAMIKOSHI M., EVANS W.R., CARMICHAEL W.W. & RINEHART K.L. 1992d. Two methyl ester derivates of microcystins, cyclic heptapeptide hepatotoxins, isolated from Anabaena flos-aqnae strain CYA 83/1. Toxicon 30: 1465-1471.
142. SKULBERG O.M., CARMICHAEL W.W., ANDERSON R.A., MATSUNAGA S., MOORE R.E. & SKULBERG R. 1992. Investigations of a neurotoxic oscillatorialean strain (Cyanophyceae) and its toxin. Isolation and characterization of homoanatoxin-a. Environmental Toxicology and Chemistry 11: 321-329.
143. SPIVAK C.E., WITKOP B. & ALBUQUERQUE E.X. 1980. Anatoxin-a: a novel, potent agonist at the nicotinic receptor. Molecular Pharmacology 18: 384-394.
144. STACHELHAUS T. & MARAHIEL M.A. 1995. Modular structure of genes encoding multifunctional peptide synthetases required for non-ribosomal peptide synthesis. MiniReview. FEMS Microbiology Letters 125: 3-14.
145. STONER R.D., ADAMS W.H., SLATKIN D.N. & SIEGELMAN H.W. 1989. The effects of single L-amino acid substitutions on the lethal potencies of the microcystins. Toxicon 27: 825-828.
146. STOTTS R.R., NAMIKOSHI M., HASCHEK W.M., RINEHART K.L., CARMICHAEL W.W., DAHLEM A.M. & BEASLEY V.R. 1993. Structural modifications imparting reduced toxicity in microcystins from Microcystis spp. Toxicon 31: 783-789.
147. SWANSON K.L., ALLEN C.N., ARONSTAM R.S., RAPOPORT H. & ALBUQUERQUE E.X. 1986. Molecular mechanisms of the potent and stereospecific nicotinic receptor agonist (+)-anatoxin-a. Molecular Pharmacology 29: 250-257.
148. TERAO K., OHMORI S., IGARASHI K., OHTANI I., WATANABE M.F., HARADA K.-I., ITO E. & WATANABE M. 1994. Electron microscopic studies on experimental poisoning in mice induced by cylindrospermopsin isolated from blue-green alga Umezakia natans. Toxicon 32: 833-843.
149. THEISS W.C. & CARMICHAEL W.W. 1986. Physiological effect of a peptide toxin produced by freshwater cyanobacteria (blue-green algae) Microcystis aeruginosa strain 7820. In: Mycotoxins and Phycotoxins (Ed. by P.S. Steyn & R. Vleggaar), pp. 353-364. Elsevier, Amsterdam.
150. TSUKAMOTO S., PAINULY P., YOUNG K.A., YANG X., SHIMIZU Y. & CORNELL L. 1993. Microcystilide A: a novel cell-differentiation-promoting depsipeptide from Microcystis aeruginosa NO-15-1840. Journal of the American Chemical Society 115: 11046-11047.
151. UTKILEN H. & GJØLME N. 1992. Toxin production by Microcystis aeruginosa as a function of light in continuous cultures and its ecological significance. Applied and Environmental Microbiology 58: 1321-1325.
152. UTKILEN H. & GJØLME N. 1995. Iron-stimulated toxin production in Microcystis aeruginosa. Applied and Environmental Microbiology 61: 797-800.
153. VAN DER WESTHUIZEN A.J. & ELOFF J.N. 1983. Effect of culture age and pH of culture medium on the growth and toxicity of the blue green alga Microcystis aeruginosa. Zeitschrift für Planzenphysiologie 110: 157-163.
154. VAN DER WESTHUIZEN A.J., ELOFF J.N. & KRÜGER G.H.J. 1986. Effect of temperature and light (fluence rate) on the composition of the toxin of the cyanobacterium Microcystis aeruginosa (UV-006). Archiv für Hydrobiologie 108: 145-154.
155. VASCONCELOS V.M. 1994. Toxic cyanobacteria (blue-green algae) in Portuguese fresh waters. Archiv für Hydrobiologie 130: 439-451.
156. VASCONCELOS V.M., SIVONEN K., EVANS W.R., CARMICHAEL W.W. & NAMIKOSHI M. 1995. Isolation and characterization of microcystins (heptapeptide hepatotoxins) from Portuguese strains of Microcystis aeruginosa Kutz. emend Elekin. Archiv für Hydrobiologie 134: 295-305.
157. WATANABE M.F. & OISHI S. 1985. Effects of environmental factors on toxicity of a cyanobacterium (Microcystis aeruginosa) under culture conditions. Applied and Environmental Microbiology 49: 1342-1344.
158. WATANABE M.F., OISHI S., HARADA K.-I., MATSUURA K., KAWAI H. & SUZUKI M. 1988. Toxins contained in Microcystis species of cyanobacteria (blue-green algae). Toxicon 26: 1017-1025.