Cyanobacteria as a source of natural products

Methods in Enzymology

Volumn 517, Issue , 2012, Pages 23-46

  Welker, Martin ^a   Dittmann, Elke ^b   Von Döhren, Hans ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF POTSDAM   (Germany)

Author keywords

Cyanobacteria; Freshwater; Keywords; Marine; Microcystin; Peptides; Phototrophic bacteria; Polyketides; Toxins

Indexed keywords

BIOFUEL; CURACIN A; CYLINDROSPERMOPSIN; DRINKING WATER; MICROCYSTIN; NATURAL PRODUCT;

ALGAL BLOOM; ARTICLE; BACTERIAL STRAIN; BACTERIUM CULTURE; BACTERIUM ISOLATION; BENTHOS; BIOASSAY; BIOMASS; CYANOBACTERIUM; ENZYME LINKED IMMUNOSORBENT ASSAY; FRACTIONATION; FREEZE DRYING; FREEZING; GENE MUTATION; GENETIC ENGINEERING AND GENE TECHNOLOGY; GENETIC MANIPULATION; HABITAT; HARVESTING; HETEROTROPH; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; IN VITRO STUDY; INOCULATION; LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; METABOLITE; METHODOLOGY; MICROCYSTIS; MUTAGENESIS; NONHUMAN; PLANKTON; PRIORITY JOURNAL; ROOM TEMPERATURE; SCREENING; SPECTROPHOTOMETRY; SYNECHOCYSTIS; THIN LAYER CHROMATOGRAPHY; TRANSCRIPTION INITIATION;

EID: 84867635829     PISSN: 00766879     EISSN: 15577988     Source Type: Book Series    
DOI: 10.1016/B978-0-12-404634-4.00002-4     Document Type: Chapter

References (77)

1. D.G. Adams, and P.S. Duggan Heterocyst and akinete differentiation in cyanobacteria The New Phytologist 144 1999 3 33 (Pubitemid 29523911)
2. O. Antal, M. Karisztl-Gacsi, A. Farkas, A. Kovacs, A. Acs, and N. Toro Screening the toxic potential of Cylindrospermopsis raciborskii strains isolated from Lake Balaton, Hungary Toxicon: Official Journal of the International Society on Toxinology 57 2011 831 840
3. A. Ballot, J. Fastner, and C. Wiedner Paralytic shellfish poisoning toxin-producing cyanobacterium Aphanizomenon gracile in Northeast Germany Applied and Environmental Microbiology 76 2010 1173 1180
4. J.A. Beutler Natural products as a foundation for drug discovery Current Protocols in Pharmacology 46s 2012 1 21
5. D.L. Bigham, M.V. Hoyer, and D.E. Canfield Survey of toxic algal (microcystin) distribution in Florida lakes Lake and Reservoir Management 25 2009 264 275
6. K.U. Bindseil, J. Jakupovic, D. Wolf, J. Lavayre, J. Leboul, and D. van der Pyl Pure compound libraries; a new perspective for natural product based drug discovery Drug Development Today 6 2001 840 847 (Pubitemid 32734512)
7. C.J.S. Bolch, and S.I. Blackburn Isolation and purification of Australian isolates of the toxic cyanobacterium Microcystis aeruginosa Kutz Journal of Applied Phycology 8 1996 5 13
8. L. Brennan, and P. Owende Biofuels from microalgae - A review of technologies for production, processing, and extractions of biofuels and co-products Renewable and Sustainable Energy Reviews 14 2010 557 777
9. G.L. Challis Mining microbial genomes for new natural products and biosynthetic pathways Microbiology (Reading, England) 154 2008 1555 1569
10. G.E. Chlipala, S. Mo, and J. Orjala Chemodiversity in freshwater and terrestrial cyanobacteria - A source for drug discovery Current Drug Targets 12 2011 1654 1673
11. G. Christiansen, J. Fastner, M. Erhard, T. Borner, and E. Dittmann Microcystin biosynthesis in planktothrix: Genes, evolution, and manipulation Journal of Bacteriology 185 2003 564 572 (Pubitemid 36070483)
12. H.D. Christman, E.L. Campbell, and J.C. Meeks Global transcription profiles of the nitrogen stress response resulting in heterocyst or hormogonium development in Nostoc punctiforme Journal of Bacteriology 193 2011 6874 6886
13. O. Czarnecki, I. Lippert, M. Henning, and M. Welker Identification of peptide metabolites of Microcystis (Cyanobacteria) that inhibit trypsin-like activity in planktonic herbivorous Daphnia (Cladocera) Environmental Microbiology 8 2006 77 87
14. E. Dittmann, B.A. Neilan, M. Erhard, H. von Döhren, and T. Borner Insertional mutagenesis of a peptide synthetase gene that is responsible for hepatotoxin production in the cyanobacterium Microcystis aeruginosa PCC 7806 Molecular Microbiology 26 1997 779 787 (Pubitemid 27489339)
15. E. Dittmann, and C. Wiegand Cyanobacterial toxins - Occurrence, biosynthesis and impact on human affairs Molecular Nutrition & Food Research 50 2006 7 17 (Pubitemid 43155092)
16. M.S. Donia, J. Ravel, and E.W. Schmidt A global assembly line for cyanobactins Nature Chemical Biology 4 2008 341 343 (Pubitemid 351693990)
17. J. Fastner, M. Erhard, W.W. Carmichael, F. Sun, K.L. Rinehart, and H. Rönicke Characterization and diversity of microcystins in natural blooms and strains of the genera Microcystis and Planktothrix from German freshwaters Archives of Hydrobiology 145 1999 147 163 (Pubitemid 29276019)
18. A. Forchert, U. Neumann, and O. Papendorf New cyanobacterial substances with bioactive properties I. Chorus, Cyanotoxins: Occurrence causes consequences 2001 Springer Berlin 295 315
19. K. Gademann, C. Portmann, J.F. Blom, M. Zeder, and F. Jüttner Multiple toxin production in the cyanobacterium Microcystis: Isolation of the toxic protease inhibitor cyanopeptolin 1020 Journal of Natural Products 73 2010 980 984
20. P.L. Haddix, C.J. Hughley, and M.W. Lechevallier Occurrence of microcystins in 33 US water supplies Journal of American Water Works Association 99 2007 118 125
21. J. Huisman Population dynamics of light-limited phytoplankton: Microcosm experiments Ecology 80 1999 202 210 (Pubitemid 29054055)
22. K. Ishida, G. Christiansen, W.Y. Yoshida, R. Kurmayer, M. Welker, and N. Valls Biosynthesis and structure of aeruginoside 126A and 126B, cyanobacterial peptide glycosides bearing a 2-carboxy-6-hydroxyoctahydroindole moiety Chemistry and Biology 14 2007 565 576 (Pubitemid 46765154)
23. K. Ishida, H. Matsuda, and M. Murakami Micropeptins 88-A to 88-F, chymotrypsin inhibitors from the cyanobacterium Microcystis aeruginosa (NIES-88) Tetrahedron 54 1998 5545 5556 (Pubitemid 28288094)
24. K. Ishida, H. Matsuda, M. Murakami, and K. Yamaguchi Micropeptins 478-A and -B, plasmin inhibitors from the cyanobacterium Microcystis aeruginosa Journal of Natural Products 60 1997 184 187 (Pubitemid 27098571)
25. K. Ishida, M. Welker, G. Christiansen, S. Cadel-Six, C. Bouchier, and E. Dittmann Plasticity and evolution of aeruginosin biosynthesis in cyanobacteria Applied and Environmental Microbiology 75 2009 2017 2026
26. H. Jenke-Kodama, and E. Dittmann Bioinformatic perspectives on NRPS/PKS megasynthases: Advances and challenges Natural Product Reports 26 2009 874 883
27. A.C. Jones, L. Gu, C.M. Sorrels, D.H. Sherman, and W.H. Gerwick New tricks from ancient algae: Natural products biosynthesis in marine cyanobacteria Current Opinion in Chemical Biology 13 2009 216 223
28. A.C. Jones, S. Ottilie, A.S. Eustaquio, D.J. Edwards, L. Gerwick, and B.S. Moore Evaluation of Streptomyces coelicolor A3(2) as a heterologous expression host for the cyanobacterial protein kinase C activator lyngbyatoxin A The FEBS Journal 279 2012 1243 1251
29. J.C. Kehr, D. Gatte Picchi, and E. Dittmann Natural product biosyntheses in cyanobacteria: A treasure trove of unique enzymes Beilstein Journal of Organic Chemistry 7 2011 1622 1635
30. O.A. Koksharova, and C.P. Wolk Genetic tools for cyanobacteria Applied Microbiology and Biotechnology 58 2002 123 137
31. L. Li, R.W. Garden, E.V. Romanova, and J.V. Sweedler In situ sequencing of peptides from biological tissues and single cells using MALDI-PSD/CID analysis Analytical Chemistry 71 1999 5451 5458
32. B. Li, D. Sher, L. Kelly, Y. Shi, K. Huang, and P.J. Knerr Catalytic promiscuity in the biosynthesis of cyclic peptide secondary metabolites in planktonic marine cyanobacteria Proceedings of the National Academy of Sciences of the United States of America 107 2010 10430 10435
33. H. Liu, and P.M. Scott Determination of the cyanobacterial toxin cylindrospermopsin in algal food supplements Food Additives and Contaminants: Part A, Chemistry, Analysis, Control, Exposure and Risk Assessment 28 2011 786 790
34. P.F. Long, W.C. Dunlap, C.N. Battershill, and M. Jaspars Shotgun cloning and heterologous expression of the patellamide gene cluster as a strategy to achieving sustained metabolite production Chembiochem 6 2005 1760 1765 (Pubitemid 41475266)
35. H. Luesch, P.G. Williams, W.Y. Yoshida, R.E. Moore, and V.J. Paul Ulongamides A-F, new beta-amino acid-containing cyclodepsipeptides from palauan collections of the marine cyanobacterium Lyngbya sp Journal of Natural Products 65 2002 996 1000 (Pubitemid 34827485)
36. J. Mitschke, A. Vioque, F. Haas, W.R. Hess, and A.M. Muro-Pastor Dynamics of transcriptional start site selection during nitrogen stress-induced cell differentiation in Anabaena sp. PCC7120 Proceedings of the National Academy of Sciences of the United States of America 108 2011 20130 20135
37. G. Molinari Natural products in drug discovery: Present status and perspectives Advances in Experimental Medicine and Biology 655 2009 13 27
38. M. Murakami, K. Ishida, T. Okino, Y. Okita, H. Matsuda, and K. Yamaguchi Aeruginosins 98-A and B, trypsin inhibitors from the blue-green alga Microcystis aeruginosa (NIES-98) Tetrahedron Letters 36 1995 2785 2788
39. M. Murakami, Y. Itou, K. Ishida, and H.J. Shin Prenylagaramides A and B, new cyclic peptides from two strains of Oscillatoria agardhii Journal of Natural Products 62 1999 752 755 (Pubitemid 29259096)
40. N. Murata, and I. Suzuki Exploitation of genomic sequences in a systematic analysis to access how cyanobacteria sense environmental stress Journal of Experimental Botany 57 2006 235 247 (Pubitemid 43063779)
41. B.A. Neilan, L.A. Pearson, J. Muenchhoff, M.C. Moffitt, and E. Dittmann Environmental conditions that influence toxin biosynthesis in cyanobacteria Environmental Microbiology 2012 http://dx.doi.org/10.1111/j.1462-2920.2012. 02729.x. [Epub ahead of print] Mar 20
42. T. Nishizawa, M. Asayama, K. Fujii, K. Harada, and M. Shirai Genetic analysis of the peptide synthetase genes for a cyclic heptapeptide microcystin in Microcystis spp Journal of Biochemistry 126 1999 520 529 (Pubitemid 29452616)
43. H.S. Okumura, B. Philmus, C. Portmann, and T.K. Hemscheidt Homotyrosine-containing cyanopeptolins 880 and 960 and anabaenopeptins 908 and 915 from Planktothrix agardhii CYA 126/8 Journal of Natural Products 72 2009 172 176
44. A. Parmar, N.K. Singh, A. Pandey, E. Gnansounou, and D. Madamwar Cyanobacteria and microalgae: A positive prospect for biofuels Bioresource Technology 102 2011 10163 10172
45. G.M.L. Patterson, L.K. Larsen, and R.E. Moore Bioactive natural-products from blue-green-algae Journal of Applied Phycology 6 1994 151 157
46. B. Philmus, G. Christiansen, W.Y. Yoshida, and T.K. Hemscheidt Post-translational modification in microviridin biosynthesis Chembiochem 9 2008 3066 3073
47. V. Reshef, and S. Carmeli Protease inhibitors from a water bloom of the cyanobacterium Microcystis aeruginosa Tetrahedron 57 2001 2885 2894 (Pubitemid 32241218)
48. R. Rippka Isolation and purification of cyanobacteria Methods in Enzymology 167 1988 3 27
49. T. Rohrlack, B. Edvardsen, R. Skulberg, C.B. Halstvedt, H.C. Utkilen, and R. Ptacnik Oligopeptide chemotypes of the toxic freshwater cyanobacterium Planktothrix can form subpopulations with dissimilar ecological traits Limnology and Oceanography 53 2008 1279 1293 (Pubitemid 352000049)
50. L. Rouhiainen, L. Paulin, S. Suomalainen, H. Hyytiainen, W. Buikema, and R. Haselkorn Genes encoding synthetases of cyclic depsipeptides, anabaenopeptilides, in Anabaena strain 90 Molecular Microbiology 37 2000 156 167 (Pubitemid 30479365)
51. A.M. Ruffing Engineered cyanobacteria: Teaching an old bug new tricks Bioengineered Bugs 2 2011 136 149
52. E.W. Schmidt, J.T. Nelson, D.A. Rasko, S. Sudek, J.A. Eisen, and M.G. Haygood Patellamide A and C biosynthesis by a microcin-like pathway in Prochloron didemni, the cyanobacterial symbiont of Lissoclinum patella Proceedings of the National Academy of Sciences of the United States of America 102 2005 7315 7320 (Pubitemid 40696376)
53. T. Shi, I. Ilikchyan, S. Rabouille, and J.P. Zehr Genome-wide analysis of diel gene expression in the unicellular N(2)-fixing cyanobacterium Crocosphaera watsonii WH 8501 The ISME Journal 4 2010 621 632
54. H.J. Shin, M. Murakami, H. Matsuda, K. Ishida, and K. Yamaguchi Oscillapeptin, an elastase and chymotrypsin inhibitor from the cyanobacterium Oscillatoria agardhii (NIES-204) Tetrahedron Letters 36 1995 5235 5238
55. H. Sielaff, G. Christiansen, and T. Schwecke Natural products from cyanobacteria: Exploiting a new source for drug discovery IDrugs 9 2006 119 127 (Pubitemid 43230762)
56. H. Sielaff, E. Dittmann, N. Tandeau De Marsac, C. Bouchier, H. von Döhren, and T. Börner The mcyF gene of the microcystin biosynthetic gene cluster from Microcystis aeruginosa encodes an aspartate racemase The Biochemical Journal 373 2003 909 916 (Pubitemid 36981101)
57. B. Spengler Post-source decay analysis in matrix-assisted laser desorption/ionization mass spectrometry of biomolecules Journal of Mass Spectrometry 32 1997 1019 1036 (Pubitemid 27454247)
58. C. Steglich, M. Futschik, T. Rector, R. Steen, and S.W. Chisholm Genome-wide analysis of light sensing in Prochlorococcus Journal of Bacteriology 188 2006 7796 7806 (Pubitemid 44764516)
59. C. Straub, P. Quillardet, J. Vergalli, N. Tandeau de Marsac, and J.F. Humbert A day in the life of microcystis aeruginosa strain PCC 7806 as revealed by a transcriptomic analysis PLoS One 6 2011 e16208
60. M. Taniguchi, J.K. Nunnery, N. Engene, E. Esquenazi, T. Byrum, and P.C. Dorrestein Palmyramide A, a cyclic depsipeptide from a Palmyra Atoll collection of the marine cyanobacterium Lyngbya majuscula Journal of Natural Products 73 2010 393 398
61. D. Tillett, E. Dittmann, M. Erhard, H. von Döhren, T. Börner, and B.A. Neilan Structural organization of microcystin biosynthesis in Microcystis aeruginosa PCC7806: An integrated peptide-poliketide synthetase system Chemistry and Biology 7 2000 753 764
62. C. Tous, M.A. Vega-Palas, and A. Vioque Conditional expression of RNase P in the cyanobacterium Synechocystis sp. PCC6803 allows detection of precursor RNAs. Insight in the in vivo maturation pathway of transfer and other stable RNAs The Journal of Biological Chemistry 276 2001 29059 29066
63. M.E. van Apeldoorn, H.P. van Egmond, G.J. Speijers, and G.J. Bakker Toxins of cyanobacteria Molecular Nutrition & Food Research 51 2007 7 60 (Pubitemid 46144763)
64. E.J. van Hannen, G. Zwart, M.P. van Agterveld, H.J. Gons, J. Ebert, and H.J. Laanbroek Changes in bacterial and eukaryotic community structure after mass lysis of filamentous cyanobacteria associated with viruses Applied and Environmental Microbiology 65 1999 795 801 (Pubitemid 29075133)
65. F. Wan, and K.L. Erickson Georgamide, a new cyclic depsipeptide with alkynoic acid residue from an Australian cyanobacterium Journal of Natural Products 64 2001 143 146 (Pubitemid 32198334)
66. M. Welker Cyanobacterial hepatotoxins: Microcystins, nodularins, and cylindrospermopsins L.M. Botana, Seafood and freshwater toxins: Pharmacology, physiology and detection 2nd ed. 2008 Taylor & Francis Group London 825 844
67. M. Welker, G. Christiansen, and H. von Döhren Diversity of coexisting Planktothrix (Cyanobacteria) chemotypes deduced by mass spectral analysis of microcystins and other oligopeptides Archives of Microbiology 182 2004 288 298 (Pubitemid 39403204)
68. M. Welker, B. Marsalek, L. Sejnohova, and H. von Döhren Detection and identification of oligopeptides in Microcystis (cyanobacteria) colonies: Toward an understanding of metabolic diversity Peptides 27 2006 2090 2103 (Pubitemid 44189619)
69. M. Welker, and H. von Döhren Cyanobacterial peptides - Nature's own combinatorial biosynthesis FEMS Microbiology Reviews 30 2006 530 563 (Pubitemid 43855766)
70. J.A. Westrick, D.C. Szlag, B.J. Southwell, and J. Sinclair A review of cyanobacteria and cyanotoxins removal/inactivation in drinking water treatment Analytical and Bioanalytical Chemistry 397 2010 1705 1714
71. WHO Guidelines for drinking-water quality 3rd ed. Recommendations Vol. 1 2006 World Health Organisation Geneva
72. R.T. Williamson, I.P. Singh, and W.H. Gerwick Taveunamides: New chlorinated toxins from a mixed assemblage of marine cyanobacteria Tetrahedron 60 2004 7025 7033 (Pubitemid 38942927)
73. C.P. Wolk Purification and storage of nitrogen-fixing filamentous cyanobacteria L. Packer, A.N. Glazer, Cyanobacteria 1988 Academic Press San Diego 93 95
74. B. Zegura, A. Straser, and M. Filipic Genotoxicity and potential carcinogenicity of cyanobacterial toxins - A review Mutation Research, Reviews in Mutation Research 727 2011 16 41
75. N. Ziemert, K. Ishida, A. Liaimer, C. Hertweck, and E. Dittmann Ribosomal synthesis of tricyclic depsipeptides in bloom-forming cyanobacteria Angewandte Chemie (International Ed. in English) 47 2008 7756 7759
76. N. Ziemert, K. Ishida, P. Quillardet, C. Bouchier, C. Hertweck, and N.T. de Marsac Microcyclamide biosynthesis in two strains of Microcystis aeruginosa: From structure to genes and vice versa Applied and Environmental Microbiology 74 2008 1791 1797 (Pubitemid 351400133)
77. R.W. Zurawell, H.R. Chen, J.M. Burke, and E.E. Prepas Hepatotoxic cyanobacteria: A review of the biological importance of microcystins in freshwater environments Journal of Toxicology and Environmental Health 8 2005 1 37 (Pubitemid 40066024)