Seven new microcystin variants discovered from a native Microcystis aeruginosa strain - Unambiguous assignment of product ions by tandem mass spectrometry

Rapid Communications in Mass Spectrometry

Volumn 29, Issue 2, 2015, Pages 220-224

  Qi, Yulin ^a   Rosso, Lorena ^b   Sedan, Daniela ^b   Giannuzzi, Leda ^b   Andrinolo, Dario ^b   Volmer, Dietrich A ^a  

^a SAARLAND UNIVERSITY   (Germany)

^b Facultad de Ciencias Naturales e Instituto M Lillo   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; TOXIC MATERIALS;

AERUGINOSA STRAINS; HIGH RESOLUTION MASS SPECTROMETRY; IDENTIFICATION OF UNKNOWNS; MASS ACCURACY; MICROCYSTIN-LR; MICROCYSTINS; MICROCYSTIS AERUGINOSA; PRODUCT IONS; TANDEM MASS SPECTROMETRY; TANDEM-MASS SPECTROMETRY;

ISOMERS;

ION; MICROCYSTIN; SEWAGE;

CHEMISTRY; ISOMERISM; MICROBIOLOGY; MICROCYSTIS; SEWAGE; TANDEM MASS SPECTROMETRY; WATER MANAGEMENT;

IONS; ISOMERISM; MICROCYSTINS; MICROCYSTIS; SEWAGE; TANDEM MASS SPECTROMETRY; WATER PURIFICATION;

EID: 84929660561     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.7098     Document Type: Article

References (31)

1. M. E. van Apeldoorn, H. P. van Egmond, G. J. A. Speijers, G. J. I. Bakker,. Toxins of cyanobacteria. Mol. Nutr. Food Res. 2007, 51, 7.
2. R. W. Zurawell, H. Chen, J. M. Burke, E. E. Prepas,. Hepatotoxic cyanobacteria: A review of the biological importance of microcystins in freshwater environments. J. Toxicol. Environ. Health, Part B 2005, 8, 1.
3. S. A. Wood, D. Mountfort, A. I. Selwood, P. T. Holland, J. Puddick, S. C. Cary,. Widespread distribution and identification of eight novel microcystins in Antarctic cyanobacterial mats. Appl. Environ. Microbiol. 2008, 74, 7243.
4. J. Bartram, I. Chorus,. Toxic Cyanobacteria in Water: A Guide to their Public Health Consequences, Monitoring and Management. Taylor & Francis, 2002.
5. M. Welker, H. Von Döhren,. Cyanobacterial peptides-Nature's own combinatorial biosynthesis. FEMS Microbiol. Rev. 2006, 30, 530.
6. F. F. del Campo, Y. Ouahid,. Identification of microcystins from three collection strains of Microcystis aeruginosa. Environ. Pollut. 2010, 158, 2906.
7. S. Bortoli, D. A. Volmer,. Account: Characterization and identification of microcystins by mass spectrometry. Eur. J. Mass Spectrom. 2014, 20, 1.
8. T. Sano, K. A. Beattie, G. A. Codd, K. Kaya,. Two (Z)-dehydrobutyrine-containing microcystins from a hepatotoxic bloom of Oscillatoria agardhii from Soulseat Loch, Scotland. J. Nat. Prod. 1998, 61, 851.
9. C. O. Miles, M. Sandvik, S. Haande, H. Nonga, A. Ballot,. LC-MS analysis with thiol derivatization to differentiate [Dhb7]- from [Mdha7]-microcystins: Analysis of cyanobacterial blooms, planktothrix cultures and European crayfish from Lake Steinsfjorden, Norway. Environ. Sci. Technol. 2013, 47, 4080.
10. J. Goldberg, H. B. Huang, Y. G. Kwon, P. Greengard, A. C. Nairn, J. Kuriyan,. 3-Dimensional structure of the catalytic subunit of protein serine/threonine phosphatase-1. Nature 1995, 376, 745.
11. S. R. Pereira, V. M. Vasconcelos, A. Antunes,. Computational study of the covalent bonding of microcystins to cysteine residues-a reaction involved in the inhibition of the PPP family of protein phosphatases. FEBS J. 2013, 280, 674.
12. E. Dittmann, C. Wiegand,. Cyanobacterial toxins-occurrence, biosynthesis and impact on human affairs. Mol. Nutr. Food Res. 2006, 50, 7.
13. E. Ito, F. Kondo, K. Terao, K.-I. Harada,. Neoplastic nodular formation in mouse liver induced by repeated intraperitoneal injections of microcystin-LR. Toxicon 1997, 35, 1453.
14. C. T. Bishop, E. F. L. J. Anet, P. R. Gorham,. Isolation And identification of the fast-death factor in Microcystis aeruginosa NRC-1. Can. J. Biochem. Physiol. 1959, 37, 453.
15. D. P. Botes, A. A. Tuinman, P. L. Wessels, C. C. Viljoen, H. Kruger, D. H. Williams, S. Santikarn, R. J. Smith, S. J. Hammond,. The structure of cyanoginosin-LA, a cyclic heptapeptide toxin from the cyanobacterium Microcystis aeruginosa. J. Chem. Soc., Perkin Trans. 1 1984, 2311.
16. L. A. Lawton, C. Edwards, G. A. Codd,. Extraction and high-performance liquid chromatographic method for the determination of microcystins in raw and treated waters. Analyst 1994, 119, 1525.
17. K. Harada, K. Ogawa, K. Matsuura, H. Murata, M. Suzuki, M. F. Watanabe, Y. Itezono, N. Nakayama,. Structural determination of geometrical isomers of microcystins LR and RR from cyanobacteria by two-dimensional NMR spectroscopic techniques. Chem. Res. Toxicol. 1990, 3, 473.
18. M.-R. Neffling, L. Spoof, J. Meriluoto,. Rapid LC-MS detection of cyanobacterial hepatotoxins microcystins and nodularins-Comparison of columns. Anal. Chim. Acta 2009, 653, 234.
19. T. Mayumi, H. Kato, S. Imanishi, Y. Kawasaki, M. Hasegawa, K. Harada,. Structural characterization of microcystins by LC/MS/MS under ion trap conditions. J. Antibiot. 2006, 59, 710.
20. K. Saito, Y. Sei, S. Miki, K. Yamaguchi,. Detection of microcystin-metal complexes by using cryospray ionization-Fourier transform ion cyclotron resonance mass spectrometry. Toxicon 2008, 51, 1496.
21. C. W. Diehnelt, N. R. Dugan, S. M. Peterman, W. L. Budde,. Identification of microcystin toxins from a strain of Microcystis aeruginosa by liquid chromatography introduction into a hybrid linear ion trap-Fourier transform ion cyclotron resonance mass spectrometer. Anal. Chem. 2005, 78, 501.
22. K. P. Bateman, P. Thibault, D. J. Douglas, R. L. White,. Mass spectral analyses of microcystins from toxic cyanobacteria using on-line chromatographic and electrophoretic separations. J. Chromatogr. A 1995, 712, 253.
23. Y. Qi, S. Bortoli, D. A. Volmer,. Detailed study of cyanobacterial microcystins using high performance tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 2014, 25, 1253.
24. L. Rosso, D. Sedan, M. Kolman, J. Caixach, C. Flores, J. M. Oteiza, G. Salerno, R. Echenique, L. Giannuzzi, D. Andrinolo,. Microcystis aeruginos strain [D-Leu1] Mcyst-LR producer, from Buenos Aires province, Argentina. J. Coastal Life Med. 2014, 2, 287.
25. L. Sleno, M. Chalmers, D. A. Volmer,. Structural study of spirolide marine toxins by mass spectrometry. Anal. Bioanal. Chem. 2004, 378, 977.
26. L. Sleno, A. Windust, D. A. Volmer,. Structural study of spirolide marine toxins by mass spectrometry. Anal. Bioanal. Chem. 2004, 378, 969.
27. P. Caravatti, M. Allemann,. The 'infinity cell': a new trapped-ion cell with radiofrequency covered trapping electrodes for Fourier transform ion cyclotron resonance mass spectrometry. Org. Mass Spectrom. 1991, 26, 514.
28. Y. Qi, P. B. O'Connor,. Data processing in Fourier transform ion cyclotron resonance mass spectrometry. Mass Spectrom. Rev. 2014, 33, 333.
29. L. L. Jessome, D. A. Volmer,. Ion suppression: a major concern in mass spectrometry. (Cover story). LC-GC North America 2006, 24, 498.
30. H. Trufelli, P. Palma, G. Famiglini, A. Cappiello,. An overview of matrix effects in liquid chromatography-mass spectrometry. Mass Spectrom. Rev. 2011, 30, 491.
31. M. Yuan, M. Namikoshi, A. Otsuki, K. Sivonen,. Effect of amino acid side-chain on fragmentation of cyclic peptide ions: differences of ESI-MS/CID mass spectra of toxic heptapeptide microcystins containing ADMAdda instead of Adda. Eur. J. Mass Spectrom. 1998, 4, 287.