Guanacastane diterpenoids from the plant endophytic fungus cercospora sp.

Journal of Natural Products

Volumn 77, Issue 4, 2014, Pages 873-881

  Feng, Yu ^a,d   Ren, Fengxia ^b   Niu, Shubin ^a,d   Wang, Lin ^a,d   Li, Li ^c   Liu, Xingzhong ^a   Che, Yongsheng ^b  

^a INSTITUTE OF MICROBIOLOGY   (China)

^b BEIJING INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (China)

^c INSTITUTE OF MATERIA MEDICA   (China)

^d UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CERCOSPORENE A; CERCOSPORENE B; CERCOSPORENE C; CERCOSPORENE D; CERCOSPORENE E; CERCOSPORENE F; DITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; AUTOPHAGY; BIOLOGICAL ACTIVITY; CANCER CELL LINE; CARBON NUCLEAR MAGNETIC RESONANCE; CERCOSPORA; CHIRALITY; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; ENDOPHYTE; FEMALE; HCT116 CELL LINE; HELA CELL LINE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; MCF 7 CELL LINE; NUCLEAR OVERHAUSER EFFECT; POLYGONUM CUSPIDATUM; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; ASCOMYCOTA; CHINA; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; DITERPENES; DRUG SCREENING ASSAYS, ANTITUMOR; HCT116 CELLS; HELA CELLS; HUMANS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PLANT LEAVES; PLANTS, MEDICINAL; POLYGONUM CUSPIDATUM; STEREOISOMERISM;

EID: 84899516498     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np4009688     Document Type: Article

References (41)

1. Strobel, G. A. Microbes Infect. 2003, 5, 535-544
2. Gunatilaka, A. A. L. J. Nat. Prod. 2006, 69, 509-526
3. Schulz, B.; Boyle, C.; Draeger, S.; Rommert, A.; Krohn, K. Mycol. Res. 2002, 106, 996-1004
4. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327
5. Strobel, G. A.; Yang, X.; Sears, J.; Kramer, R.; Sidhu, R. S.; Hess, W. M. Microbiology 1996, 142, 435-440
6. Metz, A. M.; Haddad, A.; Worapong, J.; Long, D. M.; Ford, E. J.; Hess, W. M.; Strobel, G. A. Microbiology 2000, 146, 2079-2089
7. Li, J. Y.; Strobel, G. A.; Sidhu, R. S.; Hess, W. M.; Ford, E. J. Microbiology 1996, 142, 2223-2226
8. Strobel, G. A.; Hess, W. M.; Li, J. Y.; Ford, E. J.; Sidhu, R. S.; Summerell, B. Aust. J. Bot. 1997, 45, 1073-1082
9. Zhan, Z. J.; Ying, Y. M.; Ma, L. F.; Shan, W. G. Nat. Prod. Rep. 2011, 28, 594-629
10. Fraga, B. M. Nat. Prod. Rep. 2011, 28, 1850-1610
11. Xiao, W. L.; Li, R. T.; Huang, S. X.; Pu, J. X.; Sun, H. D. Nat. Prod. Rep. 2008, 25, 871-891
12. Sun, H. D.; Huang, S. X.; Han, Q. B. Nat. Prod. Rep. 2006, 23, 673-698
13. Li, Y.; Wang, K.; Zhang, D. Y.; Hua, W. Y.; Wu, X. M. Zhongguo Ziran Yixue Zazhi 2012, 10, 429-435
14. Zou, M.; Yu, S. S.; Wang, K.; Zhang, D. Y.; Wu, X. M.; Hua, W. Y. Zhongguo Ziran Yixue Zazhi 2013, 11, 289-295
15. Gershenzon, J.; Dudareva, N. Nat. Chem. Biol. 2007, 3, 408-414
16. Kappers, I. F.; Aharoni, A.; Van Herpen, T.; Luckerhoff, L.; Dicke, M.; Bouwmeester, H. J. Science 2005, 309, 2070-2072
17. Kessler, A.; Baldwin, T. Science 2001, 291, 2141-2144
18. Geris, R.; Simpson, T. J. Nat. Prod. Rep. 2009, 26, 1063-1094
19. Oh, D. C.; Jensen, P. R.; Kauffman, C. A.; Fenical, W. Bioorg. Med. Chem. 2005, 13, 5267-5273
20. Sun, H. F.; Li, X. M.; Meng, L.; Cui, C. M.; Gao, S. S.; Li, C. S.; Huang, C. G.; Wang, B. G. J. Nat. Prod. 2012, 75, 148-152
21. Li, C.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. Org. Lett. 2002, 4, 3095-3098
22. Che, Y. Int. J. Pharm. Res. 2011, 38, 12-27
23. Brady, S. F.; Bondi, S. M.; Clardy, J. J. Am. Chem. Soc. 2001, 123, 9900-9901
24. Brady, S. F.; Singh, M. P.; Janso, J. E.; Clardy, J. J. Am. Chem. Soc. 2000, 122, 2116-2117
25. Singh, M. P.; Janso, J. E.; Luckman, S. W.; Brady, S. F.; Clardy, J.; Greenstein, M.; Maiese, W. M. J. Antibiot. 2000, 53, 256-261
26. Diedrich, C.; Grimme, S. J. Phys. Chem. A 2003, 107, 2524-2539
27. Crawford, T. D.; Tam, M. C.; Abrams, M. L. J. Phys. Chem. A 2007, 111, 12058-12068
28. Stephens, P. J.; Devlin, F. J.; Gasparrini, F.; Ciogli, A.; Spinelli, D.; Cosimelli, B. J. Org. Chem. 2007, 72, 4707-4715
29. Ding, Y.; Li, X. C.; Ferreira, D. J. Org. Chem. 2007, 72, 9010-9017
30. Berova, N.; Bari, L. D.; Pescitelli, G. Chem. Soc. Rev. 2007, 36, 914-931
31. Bringmann, G.; Bruhn, T.; Maksimenka, K.; Hemberger, Y. Eur. J. Org. Chem. 2009, 17, 2717-2727
32. Ou, Y. X.; Li, Y. Y.; Qian, X. M.; Shen, Y. M. Phytochemistry 2012, 78, 190-196
33. Djerassi, C.; Records, R.; Bunnenberg, E.; Mislow, K.; Moscowitz, A. J. Am. Chem. Soc. 1962, 84, 870-872
34. Flack, H. D. Acta Crystallogr. 1983, A39, 876-881
35. Berova, N.; Nakanishi, K. In Circular Dichroism: Principles and Applications, 2 nd ed.; Berova, N.; Nakanishi, K.; Woody, R. W., Eds.; Wiley-VCH: New York, 2000; pp 337-382.
36. Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113-4115
37. Sheldrick, G. M. SHELXL-97, Program for X-ray Crystal Structure Solution and Refinement; University of Göttingen: Göttingen, Germany, 1997.
38. Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany, 1999.
39. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
40. 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
41. Li, M.; Jiang, X.; Liu, D.; Na, Y.; Gao, G. F.; Xi, Z. Autophagy 2008, 4, 54-60