Production of anatoxin-a and a novel biosynthetic precursor by the cyanobacterium Aphanizomenon issatschenkoi

Environmental Science and Technology

Volumn 41, Issue 2, 2007, Pages 506-510

  Selwood, Andrew I ^a   Holland, Patrick T ^a   Wood, Susanna A ^a   Smith, Kirsty F ^a   Mcnabb, Paul S ^a  

^a CAWTHRON INSTITUTE   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

APHANIZOMENON ISSATSCHENKOI; CYANOTOXINS; NEUROTOXINS;

ALGAE; BIOSYNTHESIS; CELLS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; POTABLE WATER; TOXIC MATERIALS;

WATER POLLUTION;

11 CARBOXYL ANATOXIN A; ANATOXIN A; BACTERIAL TOXIN; CYANOTOXIN; DRINKING WATER; SURFACE WATER; UNCLASSIFIED DRUG;

ALGAE; BIOSYNTHESIS; CELLS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; POTABLE WATER; TOXIC MATERIALS; WATER POLLUTION;

ALGAL BLOOM; BIOMONITORING; CYANOBACTERIUM; LAKE POLLUTION; SURFACE WATER; TOXIN;

APHANIZOMENON ISSATSCHENKOI; ARTICLE; BIOSYNTHESIS; CONCENTRATION RESPONSE; CYANOBACTERIUM; FREEZE THAWING; LIQUID CHROMATOGRAPHY; NONHUMAN; SURFACE PROPERTY; TANDEM MASS SPECTROMETRY; TOXIN ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY; WATER POLLUTION;

APHANIZOMENON; BACTERIAL TOXINS; CHROMATOGRAPHY, LIQUID; FRESH WATER; NEUROTOXINS; NEW ZEALAND; TANDEM MASS SPECTROMETRY; TEMPERATURE; TIME FACTORS; TROPANES;

AUSTRALASIA; NEW ZEALAND;

APHANIZOMENON ISSATSCHENKOI; CYANOBACTERIA;

EID: 33846198729     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es061983o     Document Type: Article

References (30)

1. Devlin, J. P.; Edwards, O. E.; Gorham, P. R.; Hunter, N. R.; Pike, R. K.; Stavric, B. Anatoxin-a, a toxic alkaloid from Anabaena flos-aquae NRC-44h. Can. J. Chem. 1977, 55, 1367-1371.
2. Carmichael, W. W.; Biggs, D. F.; Peterson, M. A. Pharmacology of anatoxin-a, produced by the freshwater cyanophyte Anabaena flos-aquae NRC-44-1. Toxicon 1979, 17, 229-236.
3. Gugger, M.; Lenoir, S.; Berger, C.; Ledreux, A.; Druart, J. C.; Humbert, J. F.; Guette, C.; Bernard, C. First report in a river in France of the benthic cyanobacterium Phormidium favosum producing anatoxin-a associated with dog neurotoxicosis. Toxicon 2005, 45, 919-928.
4. Edwards, C.; Beattie, K. A.; Scrimgeour, C. M.; Codd, G. A. Identification of anatoxin-a in benthic cyanobacteria (blue-green algae) and in associated dog poisonings at Loch Insh, Scotland. Toxicon 1992, 30, 1165-1175.
5. Krienitz, L.; Ballot, A.; Kotut, K.; Wiegand, C.; Putz, S.; Metcalf, J. S.; Codd, G. A.; Pflugmacher, S. Contribution of hot spring cyanobacteria to the mysterious deaths of Lesser Flamingos at Lake Bogoria, Kenya. FEMS Microbiol. Ecol. 2003, 43, 141-148.
6. Wood, S. A.; Selwood, A.; Smith, K.; Smits, B. Sudden dog deaths caused by toxic cyanobacteria. Vetscript NZ. 2006, Feb, 6-8.
7. Sivonen, K.; Himberg, K.; Luukkainen, R.; Niemelae, S. I.; Poon, G. K.; Codd, G. A. Preliminary characterization of neurotoxic in cyanobacteria blooms and strains from Finland. Toxic. Assess. 1989, 4, 339-352.
8. Wood, S. A.; Stirling, D. J.; Briggs, L. R.; Sprosen, J.; Holland, P. T.; Ruck, J. G.; Wear, R. G. Survey of cyanotoxins in New Zealand waterbodies between 2001 and 2004. N. Z. J. Mar. Freshwater Res. 2006, 40, 585-587.
9. Viaggiu, E.; Melchiorre, S.; Volpi, F.; Di Corcia, A.; Mancini, R.; Garibaldi, L.; Crichigno, G.; Bruno, M. Anatoxin-a toxin in the cyanobacterium Planktothrix rubescens from a fishing pond in northern Italy. Environ. Toxicol. 2004, 19, 191-197.
10. Namikoshi, M.; Murakami, T.; Watanabe, M. F.; Oda, T.; Yamada, J.; Tsujimura, S.; Nagai, H.; Oishi, S. Simultaneous production of homoanatoxin-a, anatoxin-a, and a newnon-toxic 4-hydroxy-homoanatoxin-a by the cyanobacterium Raphidiopsis mediterranea Skuja. Toxicon 2003, 42, 533-538.
11. Ballot, A.; Krienitz, L.; Kotut, K.; Wiegand, C.; Pflugmacher, S. Cyanobacteria and cyanobacterial toxins in the alkaline crater lakes Sonachi and Simbi, Kenya. Harmful Algae 2005, 4, 139-150.
12. Skulberg, O. M.; Carmichael, W. W.; Anderson, R. A.; Matsunga, S.; Moore, R. E.; Skulberg, R. Investigations of a neurotoxic Oscillatorialean strain (cyanophyceae) and its toxin. Isolation and characterization of homoanatoxin-a. Environ. Toxicol. Chem. 1992, 11, 321-329.
13. Watanabe, M. F.; Tsujimura, S.; Oishi, S.; Niki, T.; Namikoshi, M. Isolation and identification of homoanatoxin-a from a toxic strain of the cyanobacterium Raphidiopsis mediterranea Skuja isolated form Lake Biwa, Japan. Phycologia 2003, 42, 364-369.
14. Furey, A.; Crowley, J.; Shuilleabhain, A. N.; Skulberg, O. M.; James, K. J. The first identification of the rare cyanobacterial toxin, homoanatoxin-a, in Ireland. Toxicon 2003, 41, 297-303.
15. Araoz, R.; Nghiem, H. O.; Rippka, R.; Palibroda, N.; de Marsac, N. T.; Herdman, M. Neurotoxins in axenic oscillatorian cyanobacteria: coexistence of anatoxin-a and homoanatoxin-a determined by ligand-binding assay and GC/MS. Microbiology 2005, 151, 1263-1273.
16. James, K. J.; Furey, A.; Sherlock, I. R.; Stack, M. A.; Twohig, M.; Caudwell, F. B.; Skulberg, O. M. Sensitive determination of anatoxin-a, homoanatoxin-a and their degradation products by liquid chromatography with fluorimetric detection. J. Chromatogr., A 1998, 798, 147-157.
17. James, K. J.; Crowley, J.; Hamilton, B.; Lehane, M.; Skulberg, O.; Furey, A. Anatoxins and degradation products, determined using hybrid quadrupole time-of-flight and quadrupole ion-trap mass spectrometry: forensic investigations of cyanobacterial neurotoxin poisoning. Rapid Commun. Mass Spectrom. 2005, 19, 1167-1175.
18. Wood, S. A. Bloom forming and toxic cyanobacteria in New Zealand: species diversity, distribution, cyanotoxin production and accumulation of microcystins in selected freshwater organisms. Doctoral thesis/dissertation, Victoria University, Wellington, New Zealand, 2005.
19. Wood, S. A.; Rasmussen, J. P.; Holland, P. T.; Campbell, R.; Crowe, A. M. First report of the cyanotoxin anatoxin-a from Aphanizomenon issatschenkoi (Cyanobacteria). J. Phycol. 2007, In press.
20. Hamill, K. D. Toxicity in benthic freshwater cyanobacteria (blue-green algae) first observations in New Zealand. N. Z. J. Mar. Freshwater Res. 2001, 35, 1057-1059.
21. Drinking-water Standards for New Zealand. Ministry of Health: Wellington, New Zealand, 2005.
22. Furey, A.; Crowley, J.; Lehane, M.; James, K. J. Liquid chromatography with electrospray ion-trap mass spectrometry for the determination of anatoxins in cyanobacteria and drinking water. Rapid Commun. Mass Spectrom. 2003, 17, 583-588.
23. Dell'Aversano, C.; Eaglesham, G. K.; Quilliam, M. A. Analysis of cyanobacterial toxins by HILIC-MS. J. Chromatogr., A 2004, 1028, 155-164.
24. Bogialli, S.; Bruno, M.; Curini, R.; Di Corcia, A.; Lagana, A. Simple and rapid determination of anatoxin-a in lake water and fish muscle tissue by liquid-chromatography-tandem mass spectrometry. J. Chromatogr., A 2006, 1122, 180-185.
25. Bolch, C. J. S.; Blackburn, S. I. Isolation and purification of Australian isolates of the toxic cyanobacterium Microcystis aeruginosa Kütz. J. Appl. Phycol. 1996, 8, 5-13.
26. Utermöhl, H. Zur vervollkommung der quantitativen phytoplanktonmethodik. Mirt. Int. Ver. Theor. Angew. Limnol. 1958, 9, 1-38.
27. Hemscheidt, T.; Rapala, J.; Sivonen, K.; Skulberg, O. M. Biosynthesis of anatoxin-a in Anabaena flos-aquae and homoanatoxin-a in Oscillatoria formosa. J. Chem. Soc., Chem. Commun. 1995, 1361-1362.
28. Namikoshi, M.; Murakami, T.; Fujiwara, T.; Nagai, H.; Niki, T.; Harigara, E.; Watanabe, M. F.; Oda, T.; Yamada, J.; Tsujimura, S. Biosynthesis and transformation of homoanatoxin-a, in the cyanobacterium Raphidiopsis mediterranea Skuja and structures of three new homologues. Chem. Res. Toxicol. 2004, 17, 1692-1696.
29. Hay, R. W.; Bond, M. A. Kinetics of the decarboxylation of acetoacetic acid. Aust. J. Chem. 1967, 20, 1823-1828.
30. O'Leary, M. H., Baughn, R. L. Acetoacetate decarboxylase. Identification of the rate- determining step in the primary amine catalysed reaction and in the enzyme reaction. J. Am. Chem. Soc. 1972, 94, 626-630.