Abstract
Some species and strains within the freshwater cyanobacterial (blue-green algal) genera Microcystis, Oscillatoria (also known as Planktothrix), Anabaena, and Nostoc are known to produce cyclic heptapeptide liver toxins, microcystins. Closely related toxic cyclic pent ape ptides, nodularins, have been isolated from the brackish water cyanobacterium Nodularia spumigena. In addition, some cyanobacteria produce neurotoxic compounds such as anatoxin-a, anatoxin-a(s), and saxitoxins. Recent reviews of the chemical and biological properties of microcystins, nodularins, and other cyanobacterial toxins are given in refe. (1–4).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
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.
Harada K.-i. (1996) Chemistry and detection of microcystins, in Toxic Microcystis (Watanabe M. F., Harada K.-i., Carmichael W. W., and Fujiki H., eds.), CRC, Boca Raton, FL, 103–148.
Carmichael W. W. (1997) The cyanotoxins. Adv. Bot. Res. 27, 211–256.
Meriluoto J. (1997) Chromatography of microcystins. Anal. Chim. Ada 352.277–298.
Falconer I. R. (1991) Tumor promotion and liver injury caused by oral consumption of cyanobacteria. Environ. Toxicol. Water Qual. 6, 177–184.
Nishiwaki-Matsushima R., Ohta T., Nishiwaki S., Suganuma M., Kohyama K., Ishikawa T., Carmichael W. W., and Fujiki H. (1992) Liver tumor promotion by the cyanobacterial cyclic peptide toxin microcystin-LR. J. Cancer Res. Clin. Oncol. 118, 420–424.
MacKmtoshy C., Beatti K.A., Klump S., Chohen P.,and Codd G.A.,(1990)Cyano-bacterial microcystin-LR is a potent and specif ic inhibitor of protein phosphatases 1 and 2A from both mammals and higher plants. FEES Lett. 264, 187–192.
Botes D. P., Tuinman A. A., Wessels P. L., Viljoen C. C, Kruger H., Williams D. H., Santikarn S., Smith R. J., and Hammond S. J. (1984) The structure of cyanoginosin-LA, a cyclic heptapeptide toxin from the cyanobacterium Microcystis aemginosa. J. Chem. Soc. Perkin Trans. 1, 2311–2318.
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., and Carmichael W. W. (1988)Nodularin, microcystin, and the configuration of Adda. J. Am. Chem. Soc. 110, 8557–8558.
MacKintosh C. (1993) Assay and purification of protein (serine/threonine) phosphatases, in Protein Phosphory lotion: A Practical Approach (Hardie D. G., ed.). IRL, Oxford, UK, 197–230.
Meriluoto J. A. O., Sandstrom A., Eriksson J. E., Remaud G., Craig A. G., and Chattopadhyaya J. (1989) Structure and toxicity of a peptide hepatotoxin from the cyanobacterium Oscillatoria agardhii. Toxicon 27, 1021–1034.
Ojanpera I., Pelander A., Vuori E., Himberg K., Waris M., and Niinivaara K. (1995) Detection of cyanobacterial hepatotoxins by TLC. J. Planar Chromatogr. 8, 69–72.
Edwards C, Lawton L. A., Coyle S.M., and Ross P. (1996) Laboratory-scale purification of microcystins using flash chromatogr aphy and reversed-phase highperformance liquid chromatogr aphy. J. Chromatogr. A 734, 163–173.
Harada K.-i., Suzuki M., Dahlem A. M., Beasley V. R., Carmichael W. W. and Rinehart K. L., Jr. (1988) Improved method for purification of toxic peptides produced by cyanobacteria. Toxicon 26, 433–439.
Harada K.-i., Matsuura K., Suzuki M., Oka H., 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 chromatogr aphy. J. Chromatogr. 448, 275–283.
Harada K., Matsuura K., Suzuki M., Watanabe M. F., Oishi S., Dahlem A.M.. Beasley V. R., and Carmichael W. W. (1990) Isolation and characterization of the minor components associated with microcystins LR and RR in the cyanobacterium (blue-green algae). Toxicon 28, 55–64.
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 aemginosa, K-139. Toxicon 29, 479–489.
Kondo F., Ikai Y., Oka H., Okumura M., Ishikawa N., Harada K.-i., Matsuura K., Murata H., and Suzuki M. (1992) Formation, characterization, and toxicity of the glutathione and cysteine conjugates of toxic heptapeptide microcystins. Chem. Res. Toxicol. 5, 591–596.
Jones B. N., Paabo S., and Stein S. (1981) Amino acid analysis and enzymatic sequence determination of peptides by an improved o-phthaldialdehyde precolumn labeling procedure. J. Liq. Chromatogr. 4, 565–586.
Meriluoto J. A. O., Eriksson J. E., Harada K.-i., Dahlem A. M., Sivonen K., and Carmichael W. W. (1990) Internal surface reversed-phase high-performance liquid chromatographic separation of the cyanobacterial peptide toxins microcystin-LA,-LR,-YR,-RR and nodularin. J. Chromatogr. 509. 390–395.
Lawton L. A., Edwards C, and Codd G. A. (1994) Extraction and high-performance liquid chromatographic method for the determination of microcystins in raw and treated waters. Analyst Lond. 119, 1525–1530.
Harada K.-i., Murata H., Qiang Z., Suzuki M., and Kondo F. (1996) Mass spectrometric screening method for microcystins in cyanobacteria. Toxicon 34. 701–710.
Beasley V. R., Dahlem A. M., Cook W. O., Valentine W. M., Lovell R. A., Hooser S. B., Harada K.-i., Suzuki M., and Carmichael W. W. (1989) Diagnostic and clinically important aspects of cyanobacterial (blue-green algae) toxicoses. J. Vet. Diagn. Invest. 1, 359–365.
Kiviranta J., Sivonen K., Niemelä S. I., and Huovinen K. (1991) Detection of toxicity of cyanobacteria by Artemia saUna bioassay. Environ. ToxicoL Water Qual. 6, 423–436.
Chu F. S., Huang X., and Wei R. D. (1990) Enzyme-linked immunosorbent assay for microcystins in blue-green algal blooms. J. Assoc. Offic. Anal. Chem. 73, 451–456.
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. Nat. Toxins 3, 78–86.
Meriluoto J., Härmälä-Brasken A.-S., Eriksson J., Toivola D., and Lindholm T. (1996) Choosing analytical strategy for microcystins. Phycohgia 35(6 Suppl. 125–132.
Tsuji K., Naito S., Kondo F., Watanabe M. F., Suzuki S., Nakazawa H., Suzuki M., Shimada T., and Harada K.-i. (1994) A clean-up method for analysis of trace amounts of microcystins in lake water. Toxicon 32, 1251–1259.
Harada K.-i., Ogawa K., Matsuura K., Murata H., Suzuki M., Watanabe M. F., Itezono Y., and Nakayama N. (1990) Structural determination of geometrical isomers of microcystins LR and RR from cyanobacteria by two-dimensional NMR spectroscopic techniques. Chem. Res. ToxicoL 3, 473–481.
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 J. W. (1994) New nodularins: a general method for structure assignment. J. Org. Chem. 59, 2349–2357.
Lawton L. A., Beattie K. A., Hawser S. P., Campbell D. L., and Codd G. A. (1994) Evaluation of assay methods for the determination of cyanobacterial hepatotoxicity, in Detection Methods for Cyanobacterial Toxins (Proceedings of the First International Symposium on Detection Methods for Cyanobacterial [BlueGreen Algal] Toxins) (Codd G. A., Jefferies T. M., Keevil C. W., and Potter E., eds.), The Royal Society of Chemistry, Cambridge, UK, 111–116.
Sano T., Nohara K., Shiraishi F., and Kaya K. (1992) A method for microdetermination of total microcystin content in waterb looms of cyanobacteria (bluegreen algae). Int. J. Environ. Anal. Chem. 49, 163–170.
Tanaka Y., Takenaka S., Matsuo H., Kitamori S., and Tokiwa H. (1993) Levels of microcystins in Japanese lakes. ToxicoL Environ. Chem. 39, 21–27.
Heinze R. (1996) A biotest for hepatotoxins using primary rat hepatocytes. Phycologia 35(6 Suppl, 89–93.
Campbell D.L., Lawton L. A., Beattie K. A., and Codd G. A. (1994) Comparative assessment of the specificity of the brine shrimp and Microtox assays to hepatotoxic (microcystin-LR-containing) cyanobacteria. Environ. ToxicoL Water QuaL 9, 71–77.
Boland M. P., Smillie M. A., Chen D. Z. X., and 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.
An J. and Carmichael W. W. (1994) Use of a colorimetric protein phosphatase inhibition assay and enzyme linked immunosorbent assay for the study of microcystins and nodularins. Toxicon 32, 1495–1507.
Harada K.-i., Oshikata M., Shimada T., Nagata A., Ishikawa N., Suzuki M., Kondo F., Shimizu M., and Yamada S. (1997) High-performance liquid chromatographic separation of microcystins derivatized with a highly fluorescent dienophile. Nat. Toxins 5, 201–207.
Murata H., Shoji H., Oshikata M., Harada K.-i., Suzuki M., Kondo F., and Goto H. (1995) High-performance liquid chromatography with chemiluminescence detection of derivatized microcystins. J. Chromatogr. A 693, 263–270.
Erhard M., von Döhren H., and Jungblut P. (1997) Rapid typing and elucidation of new secondary metabolites of intact cyanobacteria using MALDI-TOF mass spectrometry. Nat. Biotechnol. 15, 906–909.
Bouaicha N., Rivasseau C., Hennion M.-C, and Sandra P. (1996) Detection of cyanobacterial toxins (microcystins) in cell extracts by micellar electrokinetic chromatography. J. Chromatogr. B 685, 53–57.
Williams D. E., Craig M., Dawe S. C., Kent M. L., Holmes C. F. B., and Andersen R. J. (1997) Evidence for a covalently bound form of microcystin-LR in salmon liver anddungeness crab larvae. Chem. Res. ToxicoL 10, 463–469.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2000 Humana Press Inc.
About this protocol
Cite this protocol
Meriluoto, J., Lawton, L., Harada, Ki. (2000). Isolation and Detection of Microcystins and Nodularins, Cyanobacterial Peptide Hepatotoxins. In: Holst, O. (eds) Bacterial Toxins: Methods and Protocols. Methods in Molecular Biology™, vol 145. Humana Press. https://doi.org/10.1385/1-59259-052-7:65
Download citation
DOI: https://doi.org/10.1385/1-59259-052-7:65
Publisher Name: Humana Press
Print ISBN: 978-0-89603-604-8
Online ISBN: 978-1-59259-052-0
eBook Packages: Springer Protocols