Isolation of Microcystins from the Cyanobacterium Planktothrix rubescens Strain No80

doi:10.1007/s13659-013-0001-3

应用天然产物 ›› 2014, Vol. 4 ›› Issue (1): 37-45.DOI: 10.1007/s13659-013-0001-3

• Original article • 上一篇下一篇

Isolation of Microcystins from the Cyanobacterium Planktothrix rubescens Strain No80

Timo H. J. Niedermeyer^1,2, Peter Schmieder³, Rainer Kurmayer⁴

1. Cyano Biotech GmbH, Magnusstr. 11, 12489 Berlin, Germany;
2. nterfaculty Institute for Microbiology and Infection Medicine Tübingen, Eberhard Karls University Tübingen, Auf der Morgenstelle 28, 72076 Tübingen, Germany;
3. Leibniz Institut für Molekulare Pharmakologie, Robert-Rössle-Str. 10, 13125 Berlin, Germany;
4. Research Institute for Limnology, University of Innsbruck, Mondseestrasse 9, 5310 Mondsee, Austria

收稿日期:2013-10-15 修回日期:2013-11-22 出版日期:2014-02-24 发布日期:2018-02-11
通讯作者: Timo H.J.Niedermeyer,e-mail:timo.niedermeyer@uni-tuebingen.de
基金资助:
TN thanks Cyano Biotech GmbH for support and permission to publish this manuscript. We thank R. Lethaus-Weiß for her help in cultivating the strain and extracting the biomass. K. Moosbrugger performed the PP-1 inhibition assay. Part of this work has been supported by the German Federal Ministry of Economics and Technology(KF2766301SB0), the Leibniz-Institut für Molekulare Phamakologie(FMP), the Austrian Science Fund(P24070), and the Austrian Climate Research Program(ACRP) project RADICAL(Risk Analysis of Direct and Indirect Climate effects on deep Austrian Lake Ecosystems). Support from M. Beerbaum(FMP) and W. Bermel(Bruker Biospin, Karlsruhe) in all NMRspectroscopic questions is gratefully acknowledged.

Isolation of Microcystins from the Cyanobacterium Planktothrix rubescens Strain No80

Timo H. J. Niedermeyer^1,2, Peter Schmieder³, Rainer Kurmayer⁴

1. Cyano Biotech GmbH, Magnusstr. 11, 12489 Berlin, Germany;
2. nterfaculty Institute for Microbiology and Infection Medicine Tübingen, Eberhard Karls University Tübingen, Auf der Morgenstelle 28, 72076 Tübingen, Germany;
3. Leibniz Institut für Molekulare Pharmakologie, Robert-Rössle-Str. 10, 13125 Berlin, Germany;
4. Research Institute for Limnology, University of Innsbruck, Mondseestrasse 9, 5310 Mondsee, Austria

Received:2013-10-15 Revised:2013-11-22 Online:2014-02-24 Published:2018-02-11
Supported by:
TN thanks Cyano Biotech GmbH for support and permission to publish this manuscript. We thank R. Lethaus-Weiß for her help in cultivating the strain and extracting the biomass. K. Moosbrugger performed the PP-1 inhibition assay. Part of this work has been supported by the German Federal Ministry of Economics and Technology(KF2766301SB0), the Leibniz-Institut für Molekulare Phamakologie(FMP), the Austrian Science Fund(P24070), and the Austrian Climate Research Program(ACRP) project RADICAL(Risk Analysis of Direct and Indirect Climate effects on deep Austrian Lake Ecosystems). Support from M. Beerbaum(FMP) and W. Bermel(Bruker Biospin, Karlsruhe) in all NMRspectroscopic questions is gratefully acknowledged.

摘要/Abstract

摘要： Three minor microcystins have been isolated from a Planktothrix rubescens strain. Their structures have been elucidated by one-and two-dimensional NMR spectroscopy and high-resolution tandem mass spectrometry as the compounds[Asp³,(E)-Dhb⁷]MC-LY(1), [Asp³,(E)-Dhb⁷]MC-HtyW(2), and[Asp³,(E)-Dhb⁷]MC-LW(3). The amino acids found at the variable positions 2 and 4 of the microcystin core structure are in accordance with the predicted amino acid substrate activation selectivities of the non-ribosomal peptide synthetases McyA and McyB described earlier for this strain. All structural microcystin variants produced by this strain were shown to inhibit protein phosphatase 1 in the nanomolar range.

关键词: Planktothrix, Cyanobacteria, Microcystins, Protein phosphatase inhibition

Abstract: Three minor microcystins have been isolated from a Planktothrix rubescens strain. Their structures have been elucidated by one-and two-dimensional NMR spectroscopy and high-resolution tandem mass spectrometry as the compounds[Asp³,(E)-Dhb⁷]MC-LY(1), [Asp³,(E)-Dhb⁷]MC-HtyW(2), and[Asp³,(E)-Dhb⁷]MC-LW(3). The amino acids found at the variable positions 2 and 4 of the microcystin core structure are in accordance with the predicted amino acid substrate activation selectivities of the non-ribosomal peptide synthetases McyA and McyB described earlier for this strain. All structural microcystin variants produced by this strain were shown to inhibit protein phosphatase 1 in the nanomolar range.

Key words: Planktothrix, Cyanobacteria, Microcystins, Protein phosphatase inhibition

Timo H. J. Niedermeyer, Peter Schmieder, Rainer Kurmayer. Isolation of Microcystins from the Cyanobacterium Planktothrix rubescens Strain No80[J]. 应用天然产物, 2014, 4(1): 37-45.

Timo H. J. Niedermeyer, Peter Schmieder, Rainer Kurmayer. Isolation of Microcystins from the Cyanobacterium Planktothrix rubescens Strain No80[J]. Natural Products and Bioprospecting, 2014, 4(1): 37-45.

参考文献

1. W. Carmichael, V. Beasley, D.L. Bunner, J.N. Eloff, I. Falconer, P. Gorham, K.I. Harada, T. Krishnamurthy, Y. Min-Juan, R.E. Moore, K. Rinehart, M. Runnegar, O.M. Skulberg, M. Watanabe, Toxicon 26, 971-973 (1988)
2. R.W. Zurawell, H. Chen, J.M. Burke, E.E.J. Prepas, Toxicol. Environ. Health B 8, 1-37 (2005)
3. M. Welker, H. Von Dohren, FEMS Microbiol. Rev. 30, 530-563 (2006)
4. G. Christiansen, W.Y. Yoshida, J.F. Blom, C. Portmann, K. Gademann, T. Hemscheidt, R. Kurmayer, J. Nat. Prod. 71, 1881-1886 (2008)
5. R. Kurmayer, G. Christiansen, J. Fastner, T. Borner, Environ. Microbiol. 6, 831-841 (2004)
6. R. Kurmayer, M. Gumpenberger, Mol. Ecol. 15, 3849-3861 (2006)
7. C. MacKintosh, K.A. Beattie, S. Klumpp, P. Cohen, G.A. Codd, FEBS 264, 187-192 (1990)
8. K. Harada, Chem. Pharm. Bull. 52, 889-899 (2004)
9. T. Mayumi, H. Kato, S. Imanishi, Y. Kawasaki, M. Hasegawa, K. Harada, J. Antibiot. 59, 710-719 (2006)
10. T.H.J. Niedermeyer, M. Strohalm, PLoS ONE 7, e44913 (2012)
11. C.O. Miles, M. Sandvik, S. Haande, H. Nonga, A. Ballot, Environ. Sci. Tech. 47, 4080-4087 (2013)
12. C.W. Diehnelt, S.M. Peterman, W.L. Budde, Trends Anal. Chem. 24, 622-634 (2005)
13. C.W. Diehnelt, N.R. Dugan, S.M. Peterman, W.L. Budde, Anal. Chem. 78, 501-512 (2006)
14. D. Tillett, E. Dittmann, M. Erhard, H. Von Dohren, T. Borner, B.A. Neilan, Chem. Biol. 7, 753-764 (2000)
15. M. Rottig, M.H. Medema, K. Blin, T. Weber, C. Rausch, O. Kohlbacher, Nucleic Acids Res. 39, 362-367 (2011)
16. C. Rausch, T. Weber, O. Kohlbacher, W. Wohlleben, D.H. Huson, Nucleic Acids Res. 33, 5799-5808 (2005)
17. G. Christiansen, J. Fastner, M. Erhard, T. Borner, E. Dittmann, J. Bacteriol. 185, 564-572 (2003)
18. C. Taylor, R.J. Quinn, M. Suganuma, H. Fujiki, Bioorg. Med. Chem. Lett. 6, 2113-2116 (1996)
19. J.R. Bagu, B.D. Sykes, M.M. Craig, C.F.B. Holmes, J. Biol. Chem. 272, 5087-5097 (1997)
20. B.M. Gulledge, J.B. Aggen, H. Eng, K. Sweimeh, A.R. Chamberlin, Bioorg. Med. Chem. Lett. 13, 2907-2911 (2003)
21. B.M. Gulledge, J.B. Aggen, A.R. Chamberlin, Bioorg. Med. Chem. Lett. 13, 2903-2906 (2003)
22. U. Piantini, O.W. Sorensen, R.R. Ernst, J. Am. Chem. Soc. 104, 6800-6801 (1982)
23. L. Braunschweiler, R.R. Ernst, J. Magn. Reson. 53, 521-528 (1983)
24. A. Bax, D.G. Davis, J. Magn. Reson. 65, 355-360 (1985)
25. A.A. Bothner-By, R.L. Stephens, J. Lee, C.D. Warren, R.W. Jeanloz, J. Am. Chem. Soc. 106, 811-813 (1984)
26. A. Bax, D.G. Davis, J. Magn. Reson. 63, 207-213 (1985)
27. A. Bax, R.H. Griffey, B.L. Hawkins, J. Am. Chem. Soc. 105, 7188-7190 (1983)
28. H. Kessler, P. Schmieder, M. Kurz, J. Magn. Reson. 85, 400-405 (1989)
29. L. Lerner, A. Bax, J. Magn. Reson. 69, 375-380 (1986)
30. A. Bax, S. Subramanian, J. Magn. Reson. 67, 565-569 (1986)
31. A. Bax, M.F. Summers, J. Am. Chem. Soc. 108, 2093-2094 (1986)
32. G. Christiansen, C. Molitor, B. Philmus, R. Kurmayer, Mol. Biol. Evol. 25, 1695-1704 (2008)
33. R. Andersen, Algal Culturing Techniques, (Elsevier, Academic Press, Amsterdam, New York 2005), p. 596
34. J. An, W.W. Carmichael, Toxicon 32, 1495-1507 (1994)
35. R.M. Dawson, Toxicon 36, 953-962 (1998)
36. N.R. Monks, S. Liu, Y. Xu, H. Yu, A.S. Bendelow, J.A. Moscow, Mol. Cancer Ther. 6, 587-598 (2007)
37. J.F. Blom, J.A. Robinson, F. Jüttner, Toxicon 39, 1923-1932 (2001)
38. B. Beck, Y. Chen, B.J. Eastwood, M.W. Farmen, S.J. Iturria, P.W. Iversen, S.D. Kahl, R.A. Moore, B.D. Sawyer, in Assay Guidance Manual, ed. by G.S. Sittampalam, N. Gal-Edd, M. Arkin, D. Auld, C. Austin, B. Bejcek, M. Glicksman, J. Inglese, V. Lemmon, Z. Li, J. McGee, O. McManus, L. Minor, A. Napper, T. Riss, O.J. Joseph Trask, J. Weidner. Assay Operations for SAR Support, (Eli Lilly & Company and the National Center for Advancing Translational Sciences, Bethesda, 2012), http://www.ncbi.nlm.nih.gov/books/NBK91994/, Accessed 05.03.2013

Isolation of Microcystins from the Cyanobacterium Planktothrix rubescens Strain No80

Isolation of Microcystins from the Cyanobacterium Planktothrix rubescens Strain No80

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