Bi- and Tetracyclic Spirotetronates from the Coal Mine Fire Isolate Streptomyces sp. LC-6-2

Journal of Natural Products

Volumn 80, Issue 4, 2017, Pages 1141-1149

  Wang, Xiachang ^a   Elshahawi, Sherif I ^a   Cai, Wenlong ^a   Zhang, Yinan ^a   Ponomareva, Larissa V ^a   Chen, Xiabin ^a   Copley, Gregory C ^b   Hower, James C ^b   Zhan, Chang Guo ^a   Parkin, Sean ^b   Rohr, Jürgen ^a   Van Lanen, Steven G ^a   Shaaban, Khaled A ^a   Thorson, Jon S ^a  

^a University of Kentucky   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,9,11 TRIACETYLABYSSOMICIN ABYSSOMICIN Q; 3,9,11 TRIACETYLABYSSOMICIN ABYSSOMICIN S; 3,9,11,20 TETRAACETYLABYSSOMICIN ABYSSOMICIN R; ABYSSOMICIN D; ABYSSOMICIN M; ABYSSOMICIN N; ABYSSOMICIN O; ABYSSOMICIN P; ABYSSOMICIN Q; ABYSSOMICIN R; ABYSSOMICIN S; ABYSSOMICIN T; ABYSSOMICIN U; ABYSSOMICIN V; ABYSSOMICIN W; ABYSSOMICIN X; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; NATURAL PRODUCT; UNCLASSIFIED DRUG; COAL; FUSED HETEROCYCLIC RINGS; SPIRO COMPOUND;

A-549 CELL LINE; ARTICLE; BACTERIAL GENOME; BACTERIAL STRAIN; CANCER CELL LINE; CELL VIABILITY; COAL MINING; ESCHERICHIA COLI; GENE CLUSTER; GENE SEQUENCE; MICROCOCCUS LUTEUS; NONHUMAN; PHARMACOPHORE; SACCHAROMYCES CEREVISIAE; SALMONELLA ENTERICA; STAPHYLOCOCCUS AUREUS; STREPTOMYCES; STRUCTURE ACTIVITY RELATION; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; GENETICS; ISOLATION AND PURIFICATION; MULTIGENE FAMILY; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

BRIDGED BICYCLO COMPOUNDS, HETEROCYCLIC; COAL; CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MULTIGENE FAMILY; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SPIRO COMPOUNDS; STREPTOMYCES;

EID: 85018450638     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.7b00108     Document Type: Article

References (42)

1. Bister, B.; Bischoff, D.; Strobele, M.; Riedlinger, J.; Reicke, A.; Wolter, F.; Bull, A. T.; Zahner, H.; Fiedler, H. P.; Süssmuth, R. D. Angew. Chem., Int. Ed. 2004, 43, 2574-2576 10.1002/anie.200353160
2. Keller-Schierlein, W.; Muntwyle, R.; Pache, W.; Zähner, H. Helv. Chim. Acta 1969, 52, 127-142 10.1002/hlca.19690520113
3. Ding, W. D.; Williams, D. R.; Northcote, P.; Siegel, M. M.; Tsao, R.; Ashcroft, J.; Morton, G. O.; Alluri, M.; Abbanat, D.; Maiese, W. M.; Ellestad, G. A. J. Antibiot. 1994, 47, 1250-1257 10.7164/antibiotics.47.1250
4. Kellerjuslen, C.; King, H. D.; Kuhn, M.; Loosli, H. R.; Pache, W.; Petcher, T. J.; Weber, H. P.; Vonwartburg, A. J. Antibiot. 1982, 35, 142-150 10.7164/antibiotics.35.142
5. Park, H. R.; Furihata, K.; Hayakawa, Y.; Shin-ya, K. Tetrahedron Lett. 2002, 43, 6941-6945 10.1016/S0040-4039(02)01624-6
6. Lacoske, M. H.; Theodorakis, E. A. J. Nat. Prod. 2015, 78, 562-575 10.1021/np500757w
7. Vieweg, L.; Reichau, S.; Schobert, R.; Leadlay, P. F.; Süssmuth, R. D. Nat. Prod. Rep. 2014, 31, 1554-1584 10.1039/C4NP00015C
8. Niu, X. M.; Li, S. H.; Gorls, H.; Schollmeyer, D.; Hilliger, M.; Grabley, S.; Sattler, I. Org. Lett. 2007, 9, 2437-2440 10.1021/ol0705999
9. Keller, S.; Nicholson, G.; Drahl, C.; Sorensen, E.; Fiedler, H. P.; Süssmuth, R. D. J. Antibiot. 2007, 60, 391-394 10.1038/ja.2007.54
10. Igarashi, Y.; Yu, L. K.; Miyanaga, S.; Fukuda, T.; Saitoh, N.; Sakurai, H.; Saiki, I.; Alonso-Vega, P.; Trujillo, M. E. J. Nat. Prod. 2010, 73, 1943-1946 10.1021/np100292h
11. Wang, Q.; Song, F. H.; Xiao, X.; Huang, P.; Li, L.; Monte, A.; Abdel-Mageed, W. M.; Wang, J.; Guo, H.; He, W. N.; Xie, F.; Dai, H. Q.; Liu, M. M.; Chen, C. X.; Xu, H.; Liu, M.; Piggott, A. M.; Liu, X. T.; Capon, R. J.; Zhang, L. X. Angew. Chem., Int. Ed. 2013, 52, 1231-1234 10.1002/anie.201208801
12. Leon, B.; Navarro, G.; Dickey, B. J.; Stepan, G.; Tsai, A.; Jones, G. S.; Morales, M. E.; Barnes, T.; Ahmadyar, S.; Tsiang, M.; Geleziunas, R.; Cihlar, T.; Pagratis, N.; Tian, Y.; Yu, H.; Linington, R. G. Org. Lett. 2015, 17, 262-265 10.1021/ol503349y
13. Abdalla, M. A.; Yadav, P. P.; Dittrich, B.; Schuffler, A.; Laatsch, H. Org. Lett. 2011, 13, 2156-2159 10.1021/ol103076y
14. Riedlinger, J.; Reicke, A.; Zahner, H.; Krismer, B.; Bull, A. T.; Maldonado, L. A.; Ward, A. C.; Goodfellow, M.; Bister, B.; Bischoff, D.; Süssmuth, R. D.; Fiedler, H. P. J. Antibiot. 2004, 57, 271-279 10.7164/antibiotics.57.271
15. Keller, S.; Schadt, H. S.; Ortel, I.; Süssmuth, R. D. Angew. Chem., Int. Ed. 2007, 46, 8284-8286 10.1002/anie.200701836
16. Nicolaou, K. C.; Harrison, S. T. Angew. Chem., Int. Ed. 2006, 45, 3256-3260 10.1002/anie.200601116
17. Nicolaou, K. C.; Harrison, S. T. J. Am. Chem. Soc. 2007, 129, 429-440 10.1021/ja067083p
18. Nicolaou, K. C.; Harrison, S. T.; Chen, J. S. Synthesis 2009, 2009, 33-42 10.1055/s-0028-1083259
19. Byrne, M. J.; Lees, N. R.; Han, L. C.; van der Kamp, M. W.; Mulholland, A. J.; Stach, J. E.; Willis, C. L.; Race, P. R. J. Am. Chem. Soc. 2016, 138, 6095-6098 10.1021/jacs.6b00232
20. Hashimoto, T.; Hashimoto, J.; Teruya, K.; Hirano, T.; Shin-Ya, K.; Ikeda, H.; Liu, H. W.; Nishiyama, M.; Kuzuyama, T. J. Am. Chem. Soc. 2015, 137, 572-575 10.1021/ja510711x
21. Tian, Z.; Sun, P.; Yan, Y.; Wu, Z.; Zheng, Q.; Zhou, S.; Zhang, H.; Yu, F.; Jia, X.; Chen, D.; Mandi, A.; Kurtan, T.; Liu, W. Nat. Chem. Biol. 2015, 11, 259-265 10.1038/nchembio.1769
22. Wang, X.; Reynolds, A. R.; Elshahawi, S. I.; Shaaban, K. A.; Ponomareva, L. V.; Saunders, M. A.; Elgumati, I. S.; Zhang, Y.; Copley, G. C.; Hower, J. C.; Sunkara, M.; Morris, A. J.; Kharel, M. K.; Van Lanen, S. G.; Prendergast, M. A.; Thorson, J. S. Org. Lett. 2015, 17, 2796-2799 10.1021/acs.orglett.5b01203
23. Wang, X.; Shaaban, K. A.; Elshahawi, S. I.; Ponomareva, L. V.; Sunkara, M.; Copley, G. C.; Hower, J. C.; Morris, A. J.; Kharel, M. K.; Thorson, J. S. J. Antibiot. 2014, 67, 571-575 10.1038/ja.2014.37
24. Shaaban, K. A.; Wang, X.; Elshahawi, S. I.; Ponomareva, L. V.; Sunkara, M.; Copley, G. C.; Hower, J. C.; Morris, A. J.; Kharel, M. K.; Thorson, J. S. J. Nat. Prod. 2013, 76, 1619-1626 10.1021/np400308w
25. Wang, X.; Elshahawi, S. I.; Shaaban, K. A.; Fang, L.; Ponomareva, L. V.; Zhang, Y.; Copley, G. C.; Hower, J. C.; Zhan, C. G.; Kharel, M. K.; Thorson, J. S. Org. Lett. 2014, 16, 456-459 10.1021/ol4033418
26. Shaaban, K. A.; Singh, S.; Elshahawi, S. I.; Wang, X.; Ponomareva, L. V.; Sunkara, M.; Copley, G. C.; Hower, J. C.; Morris, A. J.; Kharel, M. K.; Thorson, J. S. J. Antibiot. 2014, 67, 223-230 10.1038/ja.2013.113
27. Wang, X.; Shaaban, K. A.; Elshahawi, S. I.; Ponomareva, L. V.; Sunkara, M.; Zhang, Y.; Copley, G. C.; Hower, J. C.; Morris, A. J.; Kharel, M. K.; Thorson, J. S. J. Nat. Prod. 2013, 76, 1441-1447 10.1021/np400231r
28. Shaaban, K. A.; Singh, S.; Elshahawi, S. I.; Wang, X.; Ponomareva, L. V.; Sunkara, M.; Copley, G. C.; Hower, J. C.; Morris, A. J.; Kharel, M. K.; Thorson, J. S. Nat. Prod. Res. 2014, 28, 337-339 10.1080/14786419.2013.855932
29. Shaaban, K. A.; Saunders, M. A.; Zhang, Y.; Tran, T.; Elshahawi, S. I.; Ponomareva, L. V.; Wang, X.; Zhang, J.; Copley, G. C.; Sunkara, M.; Kharel, M. K.; Morris, A. J.; Hower, J. C.; Tremblay, M. S.; Prendergast, M. A.; Thorson, J. S. J. Nat. Prod. 2017, 80, 2-11 10.1021/acs.jnatprod.6b00948
30. Wang, X.; Zhang, Y.; Ponomareva, L. V.; Qiu, Q.; Woodcock, R.; Elshahawi, S. I.; Chen, X.; Zhou, Z.; Hatcher, B. E.; Hower, J. C.; Zhan, C.; Parkin, S.; Kharel, M. K.; Voss, S. R.; Shaaban, K. A.; Thorson, J. S. Angew. Chem., Int. Ed. 2017, 56, 2994-2998 10.1002/anie.201612447
31. Elshahawi, S. I.; Cao, H.; Shaaban, K. A.; Ponomareva, L. V.; Subramanian, T.; Farman, M. L.; Spielmann, H. P.; Phillips, G. N., Jr; Thorson, J. S.; Singh, S. Nat. Chem. Biol. 2017, 13, 366-368 10.1038/nchembio.2285
32. Laatsch, H. AntiBase 2014: The Natural Compound Identifier; Wiley-VCH: Weinheim, 2014.
33. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519 10.1021/ja00783a034
34. Hoye, T. R.; Jeffrey, C. S.; Shao, F. Nat. Protoc. 2007, 2, 2451-2458 10.1038/nprot.2007.354
35. Kearse, M.; Moir, R.; Wilson, A.; Stones-Havas, S.; Cheung, M.; Sturrock, S.; Buxton, S.; Cooper, A.; Markowitz, S.; Duran, C.; Thierer, T.; Ashton, B.; Meintjes, P.; Drummond, A. Bioinformatics 2012, 28, 1647-1649 10.1093/bioinformatics/bts199
36. Lane, D. J. In Nucleic Acid Techniques in Bacterial Systematics; Stackebrandt, E.; Goodfellow, M., Eds.; John Wiley and Sons Ltd.: New York, 1991; pp 115-147.
37. Bruker. APEX2; Bruker-AXS: Madison WI, USA, 2006.
38. Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. J. Appl. Crystallogr. 2015, 48, 3-10 10.1107/S1600576714022985
39. Sheldrick, G. M. Acta Crystallogr. 2015, A71, 3-8
40. Sheldrick, G. M. Acta Crystallogr. 2015, C71, 3-8
41. Parkin, S. Acta Crystallogr., Sect. A: Found. Crystallogr. 2000, A56, 157-162 10.1107/S010876739901497X
42. Spek, A. L. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2009, D65, 148-155 10.1107/S090744490804362X