Abstract
Gombapyrones A–D, new members of the α-pyrone family of secondary metabolites, were produced by Streptomyces griseoruber Acta 3662, which was isolated from bamboo tree rhizosphere. The strain was characterized by its morphological and chemotaxonomical features and by 16S rDNA sequencing as S. griseobuber. The gombapyrone structures were determined by mass spectrometry and by NMR experiments, and were found to have an inhibitory activity against protein tyrosine phosphatase 1B and glycogen synthase kinase 3β.
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References
Schneider, K. et al. Lipocarbazoles, new secondary metabolites from Tsukamurella pseudospumae Acta 1857 with antioxidative activity. J. Nat. Prod. submitted (2009).
Fiedler, H.-P. Biosynthetic capacities of actinomycetes. 1. Screening for novel secondary metabolites by HPLC and UV-visible absorbance libraries. Nat. Prod. Lett. 2, 119–128 (1993).
Yamauchi, T., Nakashima, S., Hirayama, M., Ojiri, K. & Suda, K. Antitumor pyrone derivative BE 51068, its microbial manufacture, Streptomyces spp. therefore, and antitumor agents. Jpn. Kokai Tokkyo Koho (1998) 7 pp. JP 10101663, A 19980421 Heisei, AN 1998:236772.
Hengartner, U., Bernhard, K., Meyer, K., Englert, G. & Glinz, E. Synthesis, isolation, and NMR-spectroscopic characterization of fourteen (Z)-isomers of lycopene and of some acetylenic didehydro- and tetradehydrolycopenes. Helv. Chim. Acta. 75, 1848–1865 (1992).
Forde, J. E. & Dale, T. C. Glycogen synthase kinase 3: a key regulator of cellular fate. Cell. Mol. Life Sci. 64, 1930–1944 (2007).
Mattson, M. P. Neuronal death and GSK-3beta: a tau fetish? Trends Neurosci. 24, 255–256 (2001).
Zhang, S. & Zhang, Z.-Y. PTP1B as a drug target: recent developments in PTP1B inhibitor discovery. Drug Discov. Today 12, 373–381 (2007).
McGlacken, G. & Fairlamb, I. J. S. 2-Pyrone natural products and mimetics: isolation, characterisation and biological activity. Nat. Prod. Rep. 22, 369–385 (2005).
Fairlamb, I. J., Marrison, L. R., Dickinson, J. M., Lu, F. J. & Schmidt, J. P. 2-Pyrones possessing promising antimicrobial and cytotoxic activities. Bioorg. Med. Chem. 12, 4285–4299 (2004).
Katritzky, A. R., Wang, Z., Wang, M., Hall, C. D. & Suzuki, K. Facile syntheses of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and the corresponding 6-substituted 4-hydroxy-2-pyrones. J. Org. Chem. 70, 4854–4856 (2005).
Tummino, P. J., Ferguson, D., Huper, L. & Hupe, D. Competitive inhibition of HIV-1 protease by 4-hydroxy-benzopyran-2-ones and by 4-hydroxy-6-phenylpyran-2-ones. Biochem. Biophys. Res. Commun. 200, 1658–1664 (1994).
Hohmann, C. et al. Albidopyrone, a new α-pyrone-containing metabolite from marine-derived Streptomyces sp. NTK 227. J. Antibiot. 62, 75–79 (2009).
Hochlowski, J. E. & Faulkner, D. J. Antibiotics from the marine pulmonate Siphonaria Diemenensis. Tetetrahedron Lett. 24, 1917–1920 (1983).
Fujimoto, H. et al. Eleven new 2-pyrones from a fungi imperfecti, Trichurus terrophilus, found in a screening study guided by immunomodulatory activity. Chem. Pharm. Bull. 53, 923–929 (2005).
Zhang, D., Li, X., Kang, S. J., Choi, H. D. & Son, B. W. A new α-pyrone derivative, 6-[(E)-hept-1-enyl]-α-pyrone, with tyrosinase inhibitory activity from a marine isolate of the fungus Botrytis. Bull. Korean Chem. Soc. 28, 887–888 (2007).
Sata, N. et al. Lehualides A-D, metabolites from a Hawaiian sponge of the genus Plakortis,. J. Nat. Prod. 68, 1400–1403 (2005).
Doi, S. et al. Antibiotic CRP-2504-1 manufacture with Streptomyces. Jpn. Kokai Tokkyo Koho (1998) 8 pp. JP 10287666, A 19981027 Heisei, AN1998:696722.
Shirling, E. B. & Gottlieb, D. Methods for charcaterisation of Streptomyces species. Int. J. Syst. Bacteriol. 16, 313–340 (1966).
Takashi, S. et al. Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. J. Antibiot. 57, 173–179 (2004).
Lechevalier, M. P. & Lechevalier, H. The chemotaxonomy of actinomycetes In Actinomycetes Taxonomy Vol. 6 (eds Dietz A. &Thayer D.W.) 227–291 (Society for Industrial Microbilogy, 1980).
Rainey, F. A., Rainey, N. W., Kroppenstedt, R. M. & Stackebrandt, E. The genus Nocardiopsis represents a phylogenetically coherent taxon and a distinct actinomycetes lineage: proposal of Nocardiopsaceae fam.nov. Int. J. Syst. Bacteriol. 46, 1088–1092 (1996).
Collins, L. A. & Franzblau, S. G. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother. 41, 1004–1009 (1997).
Baki, A., Bielik, A., Molnár, L., Szendrei, G. & Keserü, G. M. A high throughput luminescent assay for glycogen synthase kinase-3b inhibitors. Assay Drug Develop. Technol. 5, 75–83 (2007).
Ellman, G. L., Courtney, K. D., Andres, Jr. V. & Featherstone, R. M. A new and rapid colorimetric determination of acetylcholesterinesterase activity. Biochem. Pharmacol. 7, 88–90 (1961).
Acknowledgements
Financial support from the European Commission (project ACTAPHARM, 5th framework, QLK3-CT-2001-01783, and project ACTINOGEN, 6th framework, LSHM-CT-2004-005224) and from Bayer Schering Pharma AG (Berlin, Germany) is gratefully acknowledged.
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Article no. 52 in ‘Biosynthetic Capacities of Actinomycetes’. Article no. 51: see reference 1.
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Helaly, S., Schneider, K., Nachtigall, J. et al. Gombapyrones, new α-pyrone metabolites produced by Streptomyces griseoruber Acta 3662. J Antibiot 62, 445–452 (2009). https://doi.org/10.1038/ja.2009.70
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DOI: https://doi.org/10.1038/ja.2009.70
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