Isolation and characterization of aphidicolin and chlamydosporol derivatives from Tolypocladium inflatum

Journal of Natural Products

Volumn 74, Issue 8, 2011, Pages 1798-1804

  Lin, Jie ^a   Chen, Xiaoyan ^b   Cai, Xiaoyue ^a   Yu, Xinfang ^b   Liu, Xingzhong ^a   Cao, Ya ^b   Che, Yongsheng ^a,c  

^a INSTITUTE OF MICROBIOLOGY   (China)

^b CENTRAL SOUTH UNIVERSITY   (China)

^c BEIJING INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

APHIDICOLIN; INFLATIN A; INFLATIN B; INFLATIN C; INFLATIN D; INFLATIN E; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; ASCOMYCETES; CHLAMYDOSPORE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; FUNGUS ISOLATION; HUMAN; HUMAN CELL; IC 50; NUCLEOTIDE SEQUENCE; TOLYPOCLADIUM INFLATUM; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

APHIDICOLIN; ASCOMYCOTA; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRONES;

TOLYPOCLADIUM INFLATUM;

EID: 80052170399     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200431k     Document Type: Article

References (51)

1. Henkel, T.; Brunne, R. M.; Müller, H.; Reichel, F. Angew. Chem., Int. Ed. 1999, 38, 643-647
2. Gloer, J. B. Acc. Chem. Res. 1995, 28, 343-350
3. Meinwald, J.; Eisner, T. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 4539-4540
4. Gloer, J. B. In The Mycota IV: Environmental and Microbial Relationships; Wicklow, D. T.;; Soderstrom, B., Eds.; Springer-Verlag: Berlin: 1997; pp 249-268.
5. Guo, H.; Hu, H.; Liu, S.; Liu, X.; Zhou, Y.; Che, Y. J. Nat. Prod. 2007, 70, 1519-1521
6. Zhang, Y.; Liu, S.; Che, Y.; Liu, X. J. Nat. Prod. 2007, 70, 1522-1525
7. Zhang, Y.; Liu, S.; Liu, H.; Liu, X.; Che, Y. J. Nat. Prod. 2009, 72, 1364-1367
8. Ma, C.; Li, Y.; Niu, S.; Zhang, H.; Liu, X.; Che, Y. J. Nat. Prod. 2011, 74, 32-37
9. Lin, J.; Liu, S.; Sun, B.; Niu, S.; Li, E.; Liu, X.; Che, Y. J. Nat. Prod. 2010, 73, 905-910
10. Dalziel, W.; Hesp, B.; Stevenson, K. M.; Jarvis, J. A. J. J. Chem. Soc., Perkin Trans. 1 1973, 2841-2851
11. Rizzo, C. J.; Wood, J. L.; Furst, G. T.; Smith, A. B. J. Nat. Prod. 1990, 53, 735-739
12. Hanson, J. R.; Takahashi, J. A. Phytochemistry 1994, 36, 1551-1552
13. Solfrizzo, M.; Visconti, A.; Savard, M. E.; Blackwell, B. A.; Nelson, P. E. Mycopathologia 1994, 127, 95-101
14. Frelek, J.; Szczepek, W. J. Tetrahedron: Asymmetry 1999, 10, 1507-1520
15. Gerards, M.; Snatzke, G. Tetrahedron: Asymmetry 1990, 1, 221-236
16. Barber, J. A.; Staunton, J.; Wilkinson, M. R. J. Chem. Soc., Perkin Trans. 1 1986, 2101-2109
17. Beutler, J. A.; McCall, K. L.; Herbert, K.; Herald, D. L.; Pettit, G. R.; Johnson, T.; Shoemaker, R. H.; Boyd, M. R. J. Nat. Prod. 2000, 63, 657-661
18. Flack, H. D. Acta Crystallogr., Sect. A 1983, 39, 876-881
19. Trost, B. M.; Nishimura, Y.; Yamamoto, K.; McElvain, S. S. J. Am. Chem. Soc. 1979, 101, 1330-1332
20. Holton, R. A.; Kennedy, R. M.; Kim, H. B.; Krafft, M. E. J. Am. Chem. Soc. 1987, 109, 1597-1600
21. Tanis, S. P.; Chuang, Y. H.; Head, D. B. J. Org. Chem. 1988, 53, 4929-4938
22. Hall, D. G.; Deslongchamps, P. J. Org. Chem. 1995, 60, 7796-7814
23. Toyota, M.; Sasaki, M.; Ihara, M. Org. Lett. 2003, 5, 1193-1195
24. Adams, M. R.; Bu'Lock, J. D. J. Chem. Soc., Chem. Commun. 1975, 389-391
25. Ackland, M. J.; Hanson, J. R.; Ratcliffe, A. H. J. Chem. Soc., Perkin Trans. 1 1984, 2751-2754
26. Ackland, M. J.; Gordon, J. F.; Hanson, J. R.; Yeoh, B. L.; Ratcliffe, A. H. J. Chem. Soc., Chem. Commun. 1987, 1492-1493
27. Gordon, J. F.; Hanson, J. R.; Ratcliffe, A. H. J. Chem. Soc., Chem. Commun. 1988, 6-7
28. Ackland, M. J.; Gordon, J. F.; Hanson, J. R.; Ratcliffe, A. H. J. Chem. Soc., Perkin Trans. 1 1988, 2009-2012
29. Hanson, J. R.; Hitchcock, P. B.; Jarvis, A. G. Phytochemistry 1997, 44, 1055-1059
30. Buchnall, R. A.; Moores, H.; Simms, R.; Hesp, B. Antimicrob. Agents Chemother. 1973, 4, 294-298
31. Ikegami, S.; Taguchi, T.; Ohashi, M.; Oguro, M.; Nagano, H.; Mano, Y. Nature 1978, 275, 458-460
32. Hanson, J. R.; Hitchcock, P. B.; Jarvis, A. G.; Rodriguez-Perez, E. M.; Ratcliffe, A. H. Phytochemistry 1992, 31, 799-803
33. Hanson, J. R.; Truneh, A. Phytochemistry 1998, 47, 423-424
34. Ichihara, A.; Oikawa, H.; Hayashi, K.; Hashimoto, M.; Sakamura, S.; Sakai, R. Agric. Biol. Chem. 1984, 48, 1687-1689
35. Oikawa, H.; Ohashi, S.; Ichihara, A.; Sakamura, S. Tetrahedron 1999, 55, 7541-7554
36. Manchand, P. S.; White, J. D.; Wright, H.; Clardy, J. J. Am. Chem. Soc. 1973, 95, 2705-2706
37. Hufford, C. D.; Guerrera, R. O.; Doorenbos, N. J. J. Pharm. Sci. 1976, 65, 778-780
38. Chamy, M. C.; Piovano, M.; Garbarino, J. A.; Gambaro, V. Phytochemistry 1991, 30, 1719-1721
39. Hufford, C. D.; Oguntimein, B. O.; Muhammad, I. J. Nat. Prod. 1992, 55, 48-52
40. Hufford, C. D. J. Nat. Prod. 1998, 51, 367-369
41. Hayashi, T.; Kawasaki, M.; Miwa, Y.; Taga, T.; Morita, N. Chem. Pharm. Bull. 1990, 38, 945-947
42. Burrows, B. F.; Turner, W. B.; Walker, E. R. H. J. Chem. Soc., Perkin Trans. 1 1975, 999-1000
43. Fujimoto, H.; Satoh, Y.; Nakayama, M.; Takayama, T.; Yamazaki, M. Chem. Pharm. Bull. 1995, 43, 547-552
44. Nakajima, H.; Nishimura, K.; Hamasaki, T.; Kimura, Y.; Yokota, T.; Udagawa, S. Agric. Biol. Chem. 1987, 51, 1221-1224
45. Nakajima, H.; Nishimura, K.; Hamasaki, T.; Kimura, Y.; Yokota, T.; Udagawa, S. Agric. Biol. Chem. 1987, 51, 2831-2833
46. Crystallographic data for 4 have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC 816055). Copies of the data can be obtained, free of charge, on application to the director, CCDC 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
47. Sheldrick, G. M. SHELXL-97, Program for X-ray Crystal Structure Solution and Refinement; University of Göttingen: Göttingen: Germany, 1997.
48. Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen: Germany, 1999.
49. Crystallographic data for 5 have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC 813929). Copies of the data can be obtained, free of charge, on application to the director, CCDC 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
50. Zhang, N.; Chen, Y.; Jiang, R.; Li, E.; Chen, X.; Xi, Z.; Guo, Y.; Liu, X.; Zhou, Y.; Che, Y.; Jiang, X. Autophagy 2011, 7, 598-612
51. Jeong, C. H.; Bode, A. M.; Pugliese, A.; Cho, Y. Y.; Kim, H. G.; Shim, J. H.; Jeon, Y. J.; Li, H.; Jiang, H.; Dong, Z. Cancer Res. 2009, 69, 5584-5591