Mass spectrometric screening method for microcystins in cyanobacteria

Toxicon

Volumn 34, Issue 6, 1996, Pages 701-710

  Harada, Ken Ichi ^a   Murata, Hideaki ^a   Qiang, Zhang ^a   Suzuki, Makoto ^a   Kondo, Fumio ^b  

^a MEIJO UNIVERSITY   (Japan)

^b AICHI PREFECTURAL INSTITUTE OF PUBLIC HEALTH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYANOGINOSIN; CYANOGINOSIN LR;

ARTICLE; CYANOBACTERIUM; GAS CHROMATOGRAPHY; ION MONITORING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; NONHUMAN; PRIORITY JOURNAL; SCREENING; TOXIN ANALYSIS;

CYANOBACTERIA;

EID: 0030175353     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/0041-0101(95)00163-8     Document Type: Article

References (36)

1. Carmichael W. W. (1992) Cyanobacteria secondary metabolites - the cyanotoxins. J. appl. Bact. 72, 445-459.
2. Carmichael W. W. (1994) The toxins of cyanobacteria. Sci. Am. 270, 64-72.
3. 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. and Watanabe M. F. (1988) Naming of cyclic heptapeptide toxins of cyanobacteria (blue-green algae). Toxicon 26, 971-973.
4. Chen D. Z. X., Boland M. P., Smillie M. A., Klix H., Ptak C., Andersen R. J. and Holmes C. F. B. (1993) Identification of protein phosphatase inhibitors of the microcystin class in the marine environment. Toxicon 31, 1407-1414.
5. Chu F. S., Huang X., Wei R. D. and Carmichael W. W. (1989) Production and characterization of antibodies against microcystins. Appl. environ. Microbiol. 55, 1928-1933.
6. Chu F. S., Huang X. and Wei R. D. (1990) Enzyme-linked immunosorbent assay for microcystins in blue-green algal blooms. J. Assoc. Off. anal. Chem. 73, 451-456.
7. Eriksson J. E., Toivola D., Meriluoto J. A. O., Karaki H., Han Y.-G. and Hartshome D. (1990) Hepatocyte deformation induced by cyanobacterial toxins reflects inhibition of protein phosphatases. Biochem. biophys. Res. Commun. 173, 1347-1353.
8. Harada K.-I., Suzuki M., Dahlem A. M., Beasley V. R., Carmichael W. W. and Rinehart K. L. (1988) Improved method for purification of toxic peptides produced by cyanobacteria. Toxicon 26, 433-439.
9. Harada K.-I., Matsuura K., Suzuki M., Watanabe M. F., Oishi S., Dahlem A. M., Beasley V. R. and Carmichael W. W. (1988) Analysis and purification of toxic peptides from cyanobacteria by reversed-phase high performance liquid chromatography. J. Chromatogr. 448, 275-283.
10. Harada K.-I., Ogawa K., Matsuura K., Nagai H., Murata H., Suzuki M., Itezono Y., Nakayama N., Shirai M. and Nakano M. (1991) Isolation of two toxic heptapeptide microcystins from an axenic strain of Microcystis aeruginosa, K-139. Toxicon 29, 479-489.
11. Harada K.-I., Nagai H., Kimura Y., Suzuki M., Park H.-D., Watanabe M. F., Luukkainen R., Sivonen K. and Carmichael W. W. (1993) Liquid chromatography/mass spectrometric detection of anatoxin-a, a neurotoxin from cyanobacteria. Tetrahedron 49, 9251-9260.
12. Holmes C. F. B. (1991) Liquid chromatography-linked protein phosphatase bioassay; a highly sensitive marine bioscreen for okadaic acid and related diarrhetic shellfish toxins. Toxicon 29, 469-477.
13. Honkanen R. E., Zwiller J., Moore R. E., Daily S. L., Khatra B. S., Dukelow M. and Boynton A. L. (1990) Characterization of microcystin-LR: a potent inhibitor of type 1 and 2A protein phosphatases. J. biol. Chem. 265, 19401-19404.
14. Kiviranta J., Namikoshi M., Sivonen K., Evans W. R., Carmichael W. W. and Rinehart K. L. (1992) Structure determination and toxicity of a new microcystin from Microcystis aeruginosa strain 205. Toxicon 30, 1093-1098.
15. Kondo F., Ikai Y., Oka H., Ishikawa N., Watanabe M. F., Watanabe M., Harada K.-I. and Suzuki M. (1992) Separation and identification of microcystins in cyanobacteria by frit-fast atom bombardment liquid chromatography/mass spectrometry. Toxicon 30, 227-237.
16. Kondo F., Ikai Y., Oka H., Matsumoto H., Yamada S., Ishikawa N., Tsuji K., Harada K.-I., Shimada T., Oshikata M. and Suzuki M. (1995) Reliable and sensitive method for determination of microcystins in complicated matrices by frit-fast atom bombardment liquid chromatography/mass spectrometry. Natural Toxins 3, 41-49.
17. Lambert T. W., Boland M. P., Holmes C. F. B. and Hrudey S. E. (1994) Quantitation of the microcystin hepatotoxins in water at environmentally relevant concentrations with the protein phosphatase bioassay. Environ. Sci. Technol. 28, 753-755.
18. Lawton L. A., Edwards C., Beattie K. A., Pleasance S., Dear G. J. and Codd G. A. (1995) Isolation and characterization of microcystins from laboratiry cultures and environmental samples of Microcystis aeruginosa and from an associated animal toxicosis. Natural Toxins 3, 50-57.
19. Luukkainen R., Namikoshi M., Sivonen K., Rinehart K. L. and Niemela 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.
20. Mackintosh C., Beattie K. A., Klumpp S., Cohen P. and 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 Lett. 264, 187-192.
21. Matsushima R., Yoshizawa S., Watanabe M. F., Harada K.-I., Furusawa M., Carmichael W. W. and Fujiki H. (1990) In vitro and in vivo effects of protein phosphatase inhibitors, microcystin and nodularin, on mouse skin and fibroblasts. Biochem. biophys. Res. Commun. 171, 867-874.
22. Nagata S., Soutome H., Tsutsumi T., Hasegawa A., Sekijima M., Sugamata M., Harada K.-I., Suganuma M. and Ueno Y. (1995) Novel monoclonal antibodies against microcystin and their protective activity for hepatotoxicity. Natural Toxins 3, 78-86.
23. Namikoshi M., Rinehart K. L., Dahlem A. M., Beasley V. R. and Carmichael W. W. (1989) Total synthesis of Adda, the unique C20 amino acid of cyanobacterial hepatotoxins. Tetrahedron Lett. 30, 4349-4352.
24. Namikoshi M., Rinehart K. L., Sakai R., Stotts R. R., Dahlem A. M., Beasley V. R., Carmichael W. W. and Evans W. R. (1992) Identification of 12 hepatotoxins from a Homer Lake bloom of the cyanobacteria Microcystis aeruginosa, Microcystis viridis, and Microcystis wesenwergii: nine new microcystins. J. org. Chem. 57, 866-872.
25. Namikoshi M., Choi B. W., Sakai R., Sun F., Rinehart K. L., Carmichael W. W., Evans W. R., Cruz P., Munro M. H. G. and Blunt W. (1994) New nodularins: a general method for structure assignment. J. org. Chem. 59, 2349-2357.
26. Nishiwaki-Matsushima R., Nishiwaki S., Ohta T., Yoshizawa S., Suganuma M., Harada K.-I., Watanabe M. F. and Fujiki H. (1991) Structure-function relationships of microcystins, liver tumor promoters, in interaction with protein phosphatase. Jpn. J. Cancer Res. 82, 993-996.
27. Park H.-D., Watanabe M. F., Harada K.-I., Nagai H., Suzuki M., Watanabe M. and Hayashi H. (1993) Hepatotoxin (microcystin) and neurotoxin (anatoxin-a) contained in natural blooms and Japanese freshwater. Natural Toxins 1, 353-360.
28. Rinehart K. L., Harada K.-I., Namikoshi M., Chen C., Harvis C. A., Munroe M. H. G., Blunt J. W., Mulligan P. E., Beaseley V. R., Dahlem A. M. and Carmichael W. W. (1988) Nodularin, microcystin, and the configuration of Adda. J. Am. Chem. Soc. 110, 8557-8558.
29. Rinehart K. L., Namikoshi M. and Choi B. W. (1994) Structure and biosynthesis of toxins from blue-green algae (cyanobacteria). J. appl. Phycol. 6, 159-176.
30. Sano T., Nohara K., Shiraishi F. and Kaya K. (1992) A method for micro-determination of total microcystin content in waterblooms of cyanobacteria (blue-green algae). Int. J. environ. anal. Chem. 49, 163-170.
31. Shirai M., Matsumura K., Ohtake A., Takamura Y., Aida T. and Nakano M. (1989) Development of a solid medium for growth and isolation of axenic Microcystis strains (cyanobacteria). Appl. environ. Microbiol. 55, 2569-2571.
32. Sim A. T. R. and Mudge L.-M. (1993) Protein phosphatase activity in cyanobacteria: consequences for microcystin toxicity analysis. Toxicon 31, 1179-1186.
33. Sivonen K., Skulberg O. N., Namikoshi M., Evans W. R., Carmichael W. W. and Rinehart K. L. (1992) Two methyl ester derivatives of microcystins, cyclic heptapeptide hepatotoxins, isolated from Anabaena flos-aquae strain CYA 83/1. Toxicon 30, 1465-1471.
34. Tanaka Y., Takenaka S., Matsuo H., Kitamori S. and Tokiwa H. (1993) Levels of microcystins in Japanese lakes. Toxic. Environ. Chem. 39, 21-27.
35. Yoshizawa S., Matsushima R., Watanabe M. F., Harada K.-I., Ichihara A., Carmichael W. W. and Fujiki H. (1990) Inhibition of protein phosphatases by microcystin and nodularin associated with hepatotoxicity. J. Cancer Res. Clin. Oncol. 116, 609-614.
36. Yu, S.-Z. (1989) Drinking water and primary liver cancer. In: Primary Liver Cancer, pp. 30-37 (Tang, Z.-Y., Wu, M.-C. and Xia, S.-S., Eds). Beijing: Springer.