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Isolation and Structure Determination of a Proteasome Inhibitory Metabolite from a Culture of Scytonema hofmanni  

Shim, Sang-Hee (School of Biotechnology, Yeungnam University)
Chlipala, George (Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago)
Orjala, Jimmy (Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago)
Publication Information
Journal of Microbiology and Biotechnology / v.18, no.10, 2008 , pp. 1655-1658 More about this Journal
Abstract
Cyanobacteria, blue-green algae, are a rich source of bioactive secondary metabolites with many potential applications. The ubiquitin-proteasome proteolytic system plays an important role in selective protein degradation and regulates cellular events including apoptosis. Cancer cells are more sensitive to the proapoptotic effects of proteasome inhibition than normal cells. Thus, proteasome inhibitors can be potential anticancer agents. Cyanobacteria have been shown to be a rich source of highly effective inhibitors of proteases. A proteasome inhibitor was screened from an extract of the culture of Scytonema hofmanni on the basis of its inhibitory activity, which led to the isolation of nostodione A with an $IC_{50}$ value of 50${\mu}M$. Its structure was determined by spectroscopic methods such as $^{1}H$-NMR and ESI-MS spectral analyses.
Keywords
Cyanobacteria; proteasome inhibitor; Scytonema hofmanni; structure determination; nostodione A;
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Times Cited By KSCI : 5  (Citation Analysis)
Times Cited By Web Of Science : 2  (Related Records In Web of Science)
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1 Beasly, V. R., R. A. Lovell, K. R. Holmes, H. E. Walcott, D. J. Schaeffer, W. E. Hoffmann, and W. W. Carmichael. 2000. Microcystin-LR decreases hepatic and renal perfusion, and causes circulatory shock, severe hypoglycemia, and terminal hyperkalemia in intravascularly dosed swine. J. Toxicol. Environ. Health 61: 281-303   DOI   ScienceOn
2 Kim, D. W., S. G. Kang, I. S. Kim, B. K. Lee, Y. T. Rho, and K. J. Lee. 2006. Proteases and protease inhibitors produced in streptomycetes and their roles in morphological differentiation. J. Microbiol. Biotechnol. 16: 5-14   과학기술학회마을
3 Orjala, J., D. G. Nagle, V. L. Hsu, and W. H. Gerwick. 1995. Antillatoxin: An exceptionally ichthyotoxic cyclic lipopeptide from the tropical cyanobacterium Lyngbya majuscule. J. Am. Chem. Soc. 117: 8281-8282   DOI   ScienceOn
4 Radau, G. 2000. Serine protease inhibiting cyanopeptides. Pharmazie 55: 555-560
5 Toivola, D. M., J. E. Eriksson, and D. L. Brautigan. 1994. Identification of protein phosphatase 2A as the primary target for microcystin-LR in rat liver homogenates. FEBS Lett. 344: 175-180   DOI
6 Kim, J. D. and C. G. Lee. 2007. Purification and characterization of extracellular ${\beta}-glucosidase$ from Sinorhizobium kostiense AFK-13 and its algal lytic effect on Anabaena flos-aquae. J. Microbiol. Biotechnol. 17: 745-752   과학기술학회마을
7 Matern, U., L. Obeer, M. Erhard, M. Herdman, and J. Weckesser. 2003. Hofmannolin, a cyclopeptolin from Scytonema hofmanni PCC 7110. Phytochemistry 64: 1061-1067   DOI   ScienceOn
8 Paramore, A. and S. Frantz. 2003. Fresh from the pipeline: Bortezomib. Nat. Rev. 2: 611-612   DOI   ScienceOn
9 Wu, M., T. Okino, L. M. Nogle, B. L. Marquez, R. T. Williamson, N. Sitachitta, et al. 2000. Structure, synthesis, and biological properties of kalkitoxin, a novel neurotoxin from the marine cyanobacterium Lyngbya majuscule. J. Am. Chem. Soc. 122: 12041-12042   DOI   ScienceOn
10 Bonjouklian, R., T. A. Smitka, A. H. Hunt, J. L. Occolowitz, T. J. Perun, L. Doolin, et al. 1996. A90720A, a serine protease inhibitor isolated from a terrestrial blue-green alga Microchaete loktakensis. Tetrahedron 52: 385-404
11 Proteau, P. J., W. H. Gerwick, F. Garcia-Pichel, and R. Castenholz. 1993. The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria. Experientia 49: 825-829   DOI
12 Lebuhn, M. and A. Hartmann. 1993. Method for the determination of indole-3-acetic acid and related compounds of L-tryptophan catabolism in soils. J. Chromatogr. 629: 255-266   DOI   ScienceOn
13 Kobayashi, A., S. Kajiyama, K. Inawaka, H. Kanzaki, and K. Kawazu. 1994. Nostodione A, a novel mitotic spindle poison from a blue-green alga Nostoc commune. J. Biosci. 49c: 464-470
14 Mundt, S., A. Nowontny, R. Mentel, A. Lesnau, and U. Lindequist. 1997. Antiviral activity of cyanobacterium Microcystis aeruginosa SPH 01. Pharm. Pharmacol. Lett. 7: 161-163
15 Pignatello, J. J., J. Porwoll, R. E. Carlson, A. Xavier, and F. K. Gleason. 1983. Structure of the antibiotic cyanobacterin, a chlorine-containing ${\gamma}-lactone$ from the freshwater cyanobacterium Scytonema hofmanni. J. Org. Chem. 48: 4035-4038   DOI
16 Zhang, L.-H., R. E. Longley, and F. E. Koehn. 1997. Antiproliferative and immunosuppressive properties of microcolin A, a marine-derived lipopeptide. Life Sci. 60: 751-762   DOI   ScienceOn
17 Agrawal, M. K., S. K. Ghosh, D. Bagchi, J. Weckesser, M. Erhard, and S. N. Bagchi. 2006. Occurrence of microcystin-containing toxic water blooms in central India. J. Microbiol. Biotechnol. 16: 212-218   과학기술학회마을
18 Gerwick, W., L. T. Tan, and N. Sitachitta. 2001. Nitrogencontaining metabolites from marine cyanobacteria, pp. 75-184. In G. A. Cordell (ed.), The Alkaloids, Vol. 57. Academic Press, San Diego
19 Humpage, A. R., S. J. Hardy, E. Moore, S. M. Froscio, and I. R. Falconer. 2000. Microcystins (cyanobacterial toxins) in drinking water enhance the growth of aberrant crypt foci in the mouse colon. J. Toxicol. Environ. Health 61: 155-165   DOI   ScienceOn
20 Richardson, P. G., T. Hideshima, and K. Anderson. 2003. Bortezomib (PS-341): A novel, first in class proteasome inhibitor for the treatment on multiple myeloma and other cancers. Cancer Control 10: 361-369   DOI
21 Luesch, H., W. Y. Yoshida, R. E. Moore, and V. J. Paul. 2000. New apratoxins of marine cyanobacterial origin from Guam and Palau. Bioorg. Med. Chem. 10: 1973-1978   DOI   ScienceOn
22 Grach-Pogrebinsky, O., B. Sedmak, and S. Carmeli. 2003. Proteasome inhibitors from a Solvenian lake bled toxic waterbloom of the cyanobacterium Planktothrix rubescens. Tetrahedron 59: 1243-1245
23 Kodani, S., S. Suzuki, K. Ishida, and M. Murakami. 1999. Five new cyanobacterial peptides from waterbloom materials of Lake Teganuma (Japan). FEMS Microbiol. Lett. 178: 343-348   DOI   ScienceOn
24 Kim, J. D. and C. G. Lee. 2006. Diversity of heterocystous filamentous cyanobacteria (blue-green algae) from rice paddy fields and their differential susceptibility to ten fungicides used in Korea. J. Microbiol. Biotechnol. 16: 240-246   과학기술학회마을
25 Mason, C. P., K. R. Edwards, R. E. Carlson, J. Pignatello, F. K. Gleason, and J. M. Wood. 1982. Isolation of chlorine-containing antibiotic from the freshwater cyanobacterium Scytonema hofmanni. Science 215: 400-402   DOI
26 Myung, J., K. B. Kim, and G. M. Crews. 2001. The ubiquitin-proteasome pathway and proteasome inhibitors. Med. Res. Rev. 21: 245-273   DOI   ScienceOn
27 Trimurtulu, G., I. Ohtani, G. M. L. Patterson, R. E. Moore, T. H. Corbett, F. A. Valeriote, and L. Demchik. 1994. Total structures of cryptophycins, potent antitumor depsipeptides from the bluegreen alga Nostoc sp. strain GSV 224. J. Am. Chem. Soc. 116: 4729-4737   DOI   ScienceOn
28 Adams, J. 2004. The proteasome: A suitable antineoplastic target. Nat. Rev. 4: 349-460   DOI   ScienceOn
29 Namikoshi, M. and K. L. Rinehardt. 1996. Bioactive compounds produced by cyanobacteria. J. Ind. Microbiol. Biotechnol. 17: 373-384   DOI   ScienceOn
30 Clardy, J. and C. Walsh. 2004. Lessons from natural molecules. Nature 432: 829-837   DOI   ScienceOn
31 Matern, U., L. Obeer, R. A. Falchetto, M. Erhard, W. A. Konig, M. Herdman, and J. Weckesser. 2001. Scyptolin A and B, cyclic depsipeptides from axenic cultures of Scytonema hofmanni PCC 7110. Phytochemistry 58: 1087-1095   DOI   ScienceOn
32 Davidson, B. S. 1995. New dimensions in natural products research: Cultured marine organisms. Curr. Opin. Biotechnol. 6: 284-291   DOI   ScienceOn
33 Luesch, H., W. Y. Yoshida, R. E. Moore, V. J. Paul, and T. H. Corbett. 2001. Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscule. J. Am. Chem. Soc. 123: 5418-5423   DOI   ScienceOn
34 Kim, J. D. and C. G. Lee. 2006. Differential responses of two freshwater cyanobacteria, Anabaena variabilis and Nostoc commune, to sulfonylurea herbicide bensulfuron-methyl. J. Microbiol. Biotechnol. 16: 52-56   과학기술학회마을