Aspergillines A-E, highly oxygenated hexacyclic indole-tetrahydrofuran-tetramic acid derivatives from aspergillus versicolor

Organic Letters

Volumn 16, Issue 19, 2014, Pages 5016-5019

  Zhou, Min ^a,b   Miao, Ming Ming ^a   Du, Gang ^b   Li, Xiao Nian ^c   Shang, Shan Zhai ^a   Zhao, Wei ^a   Liu, Zhi Hua ^a   Yang, Guang Yu ^a   Che, Chun Tao ^d   Hu, Qiu Fen ^a   Gao, Xue Mei ^a,b  

^a CHINA TOBACCO YUNNAN INDUSTRIAL CO   (China)

^b YUNNAN MINZU UNIVERSITY   (China)

^c KUNMING INSTITUTE OF BOTANY   (China)

^d UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ALKALOID; ANTINEOPLASTIC AGENT; CYCLOPIAZONIC ACID; FUSED HETEROCYCLIC RINGS; INDOLE DERIVATIVE; TETRAMIC ACID;

ASPERGILLUS; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; DRUG SCREENING; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; ANTINEOPLASTIC AGENTS; ASPERGILLUS; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDOLES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRROLIDINONES;

EID: 84907805634     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502307u     Document Type: Article

References (29)

1. Li, S. M. Nat. Prod. Rep. 2010, 27, 57-78
2. Liu, X. Y.; Walsh, C. T. Biochemistry 2009, 48, 8746-8757
3. Holzapfel, C. W.; Wilkins, D. C. Phytochemistry 1971, 10, 351-358
4. Chang, P. K.; Ehrlich, K. C.; Fujii, I. Toxins 2009, 1, 74-99
5. Seshime, Y.; Juvvadi, P. R.; Tokuoka, M.; Koyama, Y.; Kitamoto, K.; Ebizuka, Y.; Fujii, I. Bioorg. Med. Chem. Lett. 2009, 19, 3288-3292
6. Liu, X. Y.; Walsh, C. T. Biochemistry 2009, 48, 11032-11044
7. Royles, B. J. Chem. Rev. 1995, 95, 1981-2001
8. Chen, M.; Roush, W. R. Org. Lett. 2012, 14, 426-428
9. Mo, X. H.; Huang, H. B.; Ma, J. Y.; Wang, Z. W.; Wang, B.; Zhang, S.; Zhang, C. S.; Ju, J. H. Org. Lett. 2011, 13, 2212-2215
10. Chen, H.; Olesen, S. G.; Harrison, P. H. M. Org. Lett. 2006, 8, 5329-5332
11. Ganzle, M. G. Appl. Microbiol. Biotechnol. 2004, 64, 326-332
12. Deboer, C.; Dietz, A.; Silver, W. S.; Savage, G. M. Antibiot. Ann. 1956, 886-892
13. Li, J. Y.; Strobel, G.; Harper, J.; Lobkovsky, E.; Clardy, J. Org. Lett. 2000, 2, 767-770
14. Shigeura, H. T.; Gordon, C. N. Biochemistry 1963, 2, 1132-1137
15. Singh, S. B.; Zink, D. L.; Heimbach, B.; Genilloud, O.; Teran, A.; Silverman, K. C.; Lingham, R. B.; Felock, P.; Hazuda, D. J. Org. Lett. 2002, 4, 1123-1126
16. Biersack, B.; Diestel, R.; Jagusch, C.; Rapp, G.; Sasse, F.; Schobert, R. Chem. Biodiversity 2008, 5, 2423-2430
17. Holzapfel, C. W. Tetrahedron 1968, 24, 2101-2119
18. Beyer, W. R. C.; Woithe, K.; Luke, B.; Schindler, M.; Antonicek, H.; Scherkenbeck, J. Tetrahedron 2011, 67, 3062-3070
19. Uhlemann, A. C.; Cameron, A.; Eckstein-Ludwig, U.; Fischbarg, J.; Iserovich, P.; Zuniga, F. A.; East, M.; Lee, A.; Brady, L.; Haynes, R. K.; Krishna, S. Nature Struct. Mol. Biol. 2005, 12, 628-629
20. Tsuda, M.; Mugishima, T.; Komatsu, K.; Sone, T.; Tanaka, M.; Mikami, Y.; Shiro, M.; Hirai, M.; Ohizumie, Y.; Kobayashi, J. Tetrahedron 2003, 59, 3227-3230
21. Kozikowski, A. P.; Grecco, M. N.; Springer, J. P. J. Am. Chem. Soc. 1984, 106, 6873-6874
22. Haskins, C. M.; Knight, D. W. Chem. Commun. 2005, 25, 3162-3164
23. Lin, A. Q.; Du, L.; Fang, Y. C.; Wang, F. Z.; Zhu, T. J.; Gu, Q. Q.; Zhu, W. M. Chem. Nat. Compd. 2009, 45, 677-680
24. Holzapfel, C. W.; Hutchison, R. D. Phytochemistry 1970, 26, 5239-5246
25. Hooft, R. W. W.; Straver, L. H.; Spek, A. L. J. Appl. Crystallogr. 2008, 41, 96-103
26. Flack, H. D. Acta Crystallogr. 1983, A39, 876-881
27. Flack, H. D.; Bernardinelli, G. Chirality 2008, 20, 681-690
28. Hu, Q. F.; Zhou, B.; Huang, J. M.; Gao, X. M.; Shu, L. D.; Yang, G. Y.; Che, C. T. J. Nat. Prod. 2013, 76, 292-296
29. Gao, X. M.; Wang, R. R.; Niu, D. Y.; Meng, C. Y.; Yang, L. M.; Zheng, Y. T.; Yang, G. Y.; Hu, Q. F.; Sun, H. D.; Xiao, W. L. J. Nat. Prod. 2013, 76, 1052-1057