Butrepyrazinone, a new pyrazinone with an unusual methylation pattern from a ghanaian Verrucosispora sp. K51G

Marine Drugs

Volumn 12, Issue 10, 2014, Pages 5197-5208

  Kyeremeh, Kwaku ^a   Acquah, Kojo Sekyi ^a   Camas, Mustafa ^b   Tabudravu, Jioji ^c   Houssen, Wael ^c,d   Deng, Hai ^c   Jaspars, Marcel ^c  

^a UNIVERSITY OF GHANA   (Ghana)

^b TUNCELI UNIVERSITY   (Turkey)

^c UNIVERSITY OF ABERDEEN   (United Kingdom)

^d MANSOURA UNIVERSITY   (Egypt)

Author keywords

Actinomycete; Mangrove; Micromonosporaceae; Pyrazinone

Indexed keywords

BUTREPYRAZINONE; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT;

ACTINOBACTERIA; ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; ESCHERICHIA COLI; FERMENTATION; GHANA; MASS SPECTROMETRY; MATHEMATICAL ANALYSIS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; METHYLATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STAPHYLOCOCCUS AUREUS; VERRUCOSISPORA; ACTINOMYCETALES; CHEMISTRY; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; MICROBIOLOGY; RIVER; SEDIMENT;

MICROMONOSPORACEAE; NEGIBACTERIA; POSIBACTERIA; STAPHYLOCOCCUS AUREUS; VERRUCOSISPORA;

ACTINOBACTERIA; ACTINOMYCETALES; ANTI-BACTERIAL AGENTS; ESCHERICHIA COLI; GEOLOGIC SEDIMENTS; GHANA; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; METHYLATION; MICROBIAL SENSITIVITY TESTS; PYRAZINES; RIVERS;

EID: 84908190395     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12105197     Document Type: Article

References (29)

1. Zimmermann, M.; Fischbach, M.A. A family of pyrazinone natural products from a conserved nonribosomal peptide synthetase in Staphylococcus aureus. Chem. Biol. Brief Commun. 2010, 17, 925-930.
2. Wyatt, M.A.; Wang, W.; Roux, C.M.; Beasley, F.C.; Heinrichs, D.E.; Dunman, P.M.; Magarvey, N.A. Staphylococcus aureus nonribosomal peptide secondary metabolites regulate virulence. Science 2010, 329, 294-296.
3. Alvarez, M.E.; White, C.B.; Gregory, J.; Kydd, G.C.; Harris, A.; Sun, H.H.; Gillum, A.M.; Cooper, R.; Antibiot, J. Phevalin, a new calpain inhibitor, from a Streptomyces sp. J. Antibiot. (Tokyo) 1995, 48, 1165-1167.
4. Motohashi, K.; Inaba, K.; Fuse, S.; Doi, T.; Izumikawa, M.; Khan, S.T.; Takagi, M.; Takahashi, T.; Shin-ya, K. JBIR-56 and JBIR-57, 2(1H)-pyrazinones from a marine sponge-derived Streptomyces sp. SpD081030SC-03. J. Nat. Prod. 2011, 74, 1630-1635.
5. Tang, Y.-Q.; Sattler, I.; Thiericke, R.; Grabley, S.; Feng, X.-Z. Maremycins C and D, new diketopiperazines, and maremycins E and F, novel Polycyclic spiro-indole metabolites isolated from Streptomyces sp. Eur. J. Org. Chem. 2000, 2, 261-267.
6. Rheims, H.; Schumann, P.; Rohde, M.; Stackebrandt, E. Verrucosispora gifhornensis gen. nov., sp. nov., a new member of the actinobacterial family Micromonosporaceae. Int. J. Syst. Bacteriol. 1998, 48, 1119-1127.
7. Krasil'nikov, N.A. Ray Fungi and Related Organisms-Actinomycetales; Akademii Nauk SSSR: Moscow, Russia, 1938.
8. Koch, C.; Kroppenstedt, R.M.; Rainey, F.A.; Stackebrandt, E. 16S ribosomal DNA analysis of the genera Micromonospora, Actinoplanes, Catellatospora, Catenuloplanes, Couchioplanes, Dactylosporangium, and Pilimelia and emendation of the family Micromonosporaceae. Int. J. Syst. Bacteriol. 1996, 46, 765-768.
9. Stackebrandt, E.; Rainey, F.A.; Ward-Rainey, N.L. Proposal for a new hierarchic classification system, Actinobacteria classis nov. Int. J. Syst. Bacteriol. 1997, 47, 479-491.
10. Kupchan, M.S.; Britton, R.W.; Zeigler, M.F.; Sigel, C.W. Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica. J. Org. Chem. 1973, 38, 178-179.
11. ACD/Structure Elucidator, version 12.5. Available online: http://www.acd.labs.com (accessed on 8 July 2014).
12. Elyashberg, M; Williams, A.J.; Blinov, K. Structural revisions of natural products by Computer-Assisted Structure Elucidation (CASE) systems. Nat. Prod. Rep. 2010, 27, 1296-1328.
13. Bremser, W. Host-A novel substructure code. Anal. Chim. Acta 1978, 103, 355-365.
14. Smurnyy, Y.D.; Blinov, K.A.; Churanova, T.S.; Elyashberg, M.E.; Williams, A.J. Towards more reliable 13C and 1H chemical shift prediction: A systematic comparison of neural network and least squares regression based approaches. J. Chem. Inf. Model. 2008, 48, 128-134.
15. Tsunematsu, Y.; Fukutomi, M.; Saruwatari, T.; Noguchi, H.; Hotta, K.; Tang, Y.; Watanabe, K. Elucidation of pseurotin biosynthetic pathway points to trans-acting C-methyltransferase: Generation of chemical diversity. Angew. Chem. Int. Ed. Engl. 2014, 53, 8475-8479.
16. Kim, O.-S.; Cho, Y.-J.; Lee, K.; Yoon, S.-H.; Kim, M.; Na, H.; Park, S.-C.; Jeon, Y.S.; Lee, J.H.; Yi, H.; et al. Introducing EzTaxon-e: A prokaryotic 16S rRNA gene sequence database with phylotypes that represent uncultured species. Int. J. Syst. Evol. Microbiol. 2012, 62, 716-721.
17. Tamura, K.; Stecher, G.; Peterson, D.; Filipski, A.; Kumar, S. MEGA6: Molecular Evolutionary Genetics Analysis Version 6.0. Mol. Biol. Evol. 2013, 30, 2725-2729.
18. Saitou, N.; Nei, M. The neighbor-joining method: A new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 1987, 4, 406-425.
19. Felsenstein, J. PHYLIP (Phylogenetic Inference Package), Version 3.5c; Distributed by the author; Department of Genome Sciences, University of Washington: Seattle, WA, USA, 1993.
20. Fitch, W.M. Toward defining the course of evolution: Minimum change for a specific tree topology. Syst. Zool. 1971, 20, 406-416.
21. Jukes, T.H.; Cantor, C.R. Evolution of Protein Molecules. In Mammalian Protein Metabolism; Munro, H.N., Ed.; Academic Press: New York, NY, USA, 1969; Volume 3, pp. 21-132.
22. Felsenstein, J. Confidence limits on phylogeny: An approach using the bootstrap. Evolution 1985, 39, 783-791.
23. Domenech, P.; Kobayashi, H.; LeVier, K.; Walker, G.C.; Barry, C.E. BacA, an ABC Transporter Involved in Maintenance of Chronic Murine Infections with Mycobacterium tuberculosis. J. Bacteriol. 2009, 191, 477-485.
24. Müller, H.J.; Hinton, J. A protein-free medium for primary isolation of the Gonococcus and Meningococcus. Proc. Soc. Exp. Biol. Med. 1941, 48, 330-333.
25. Barthelon, A.; Dos Santos, A.; El Kaim, L.; Grimaud, L. Ugi/Smiles access to pyrazine scaffolds. Tetrahedron Lett. 2008, 49, 3208-3211.
26. Yokoi, T.; Taguchi, H.; Nishiyama, Y.; Igarashi, K.; Kasuya, F.; Okada, Y. Amino acids and peptides. Part 48. Studies on the structure of an unexpected reaction product from dipeptidyl chloromethyl ketone during acid hydrolysis. J. Chem. Res. Synop. 1997, 1, 10-11.
27. Taguchi, H.; Yokoi, T.; Tsukatani, M.; Okada, Y. Amino acids and peptides. XLI. Facile synthesis of 5-methyl-2(1H)-pyrazinone derivatives from dipeptidyl chloromethyl ketones. Tetrahedron 1995, 51, 7361-7372.
28. Taguchi, H.; Yokoi, T.; Kasuya, F.; Nishiyama, Y.; Fukui, M.; Okada, Y. Unexpected reaction of dipeptidyl chloromethyl ketone during acid hydrolysis. J. Chem. Soc. Chem. Commun. 1994, 3, 247; doi:10.1039/C39940000247.
29. Okada, Y.; Tuguchi, H.; Nishiyama, Y.; Yokoi, T. Simple approach towards the synthesis of 5-methyl-2-hydroxypyrazine derivatives from dipeptidyl chloromethyl ketones. Tetrahedron Lett. 1994, 35, 1231-1234.