Thiersinines A and B: Novel Antiinsectan Indole Diterpenoids from a New Fungicolous Penicillium Species (NRRL 28147)

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3095-3098

  Li, Chen ^a   Gloer, James B ^a   Wicklow, Donald T ^b   Dowd, Patrick F ^b  

^a The University of Iowa   (United States)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; INDOLE DERIVATIVE; INSECTICIDE; PAXILLINE; SPIRO COMPOUND; THIERSININE A; THIERSININE B;

ANIMAL; ARMYWORM; ARTICLE; CHEMISTRY; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; PENICILLIUM;

ANIMALS; DITERPENES; INDOLES; INSECTICIDES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PENICILLIUM; SPIRO COMPOUNDS; SPODOPTERA;

EID: 0037026558     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026424a     Document Type: Article

References (23)

1. Gloer, J. B. Acc. Chem. Res. 1995, 28, 343-350 and references therein.
2. Belofsky, G. N.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. Tetrahedron 1995, 51, 3959-3968.
3. Belofsky, G. N.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. Tetrahedron Lett. 1998, 39, 5497-5500.
4. Joshi, B. K.; Gloer, J. B.; Wicklow, D. T. J. Nat. Prod. 1999, 62, 730-733.
5. Soman, A. G.; Gloer, J. B.; Angawi, R. F.; Wicklow, D. T.; Dowd, P. F. J. Nat. Prod. 2001, 64, 189-192.
6. 7 + Na, 532.2311.
7. Springer, J. P.; Clardy, J.; Wells, J. M. Tetrahedron Lett. 1975, 30, 2531-2534.
8. Springer, J. P.; Clardy, J. Tetrahedron Lett. 1980, 21, 231-234.
9. Nozawa, K.; Nakajima, S.; Kawai, K. J. Chem. Soc., Perkin Trans. 1 1988, 2607-2610.
10. Nozawa, K.; Yoshikazu, H.; Udagawa, S.; Kawai, K.; Yamazaki, M. Chem. Pharm. Bull. 1989, 37, 1387-1389.
11. Hosoe, T.; Nozawa, K.; Udagawa, S.; Nakajima, S.; Kawai, K. Chem. Pharm. Bull. 1990, 38, 3473-3475.
12. Hinkley, S. F.; Fettinger, J. C.; Dudley, K.; Jarvis, B. B. J. Antibiot. 1999, 52, 988-997.
13. Tezuka, Y. Carbohydr. Res. 1999, 305, 155-161.
14. 1H NMR, HPLC, and TLC analysis.
15. Hart, D. J.; Havas, F. C. K. Acad. Sci., Paris, Ser. IIc: Chim. 2001, 4, 591-598.
16. Gallagher, R. T.; Finer, J.; Clardy, J.; Leutwiler, A.; Weibel, F.; Acklin, W.; Arigoni, D. Tetrahedron Lett. 1980, 21, 235-238.
17. Ondeyka, J. G.; Helms, G. L.; Hensens, O. D.; Goetz, M. A.; Zink, D. L.; Tsipouras, A.; Shoop, W. L.; Slayton, L.; Dombrowski, A. W.; Polishook, J. D.; Ostlind, D. A.; Tsou, N. N.; Ball, R. G.; Singh, S. B. J. Am Chem. Soc. 1997, 119, 8809-8816. Chakravarty, P. K.; Tyagarajan, S.; Shih, T. L.; Salva, S.; Snedden, C.; Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T. Org. Lett. 2002, 4, 1291-1294.
18. Ondeyka, J. G.; Helms, G. L.; Hensens, O. D.; Goetz, M. A.; Zink, D. L.; Tsipouras, A.; Shoop, W. L.; Slayton, L.; Dombrowski, A. W.; Polishook, J. D.; Ostlind, D. A.; Tsou, N. N.; Ball, R. G.; Singh, S. B. J. Am Chem. Soc. 1997, 119, 8809-8816. Chakravarty, P. K.; Tyagarajan, S.; Shih, T. L.; Salva, S.; Snedden, C.; Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T. Org. Lett. 2002, 4, 1291-1294.
19. Turner, W. B.; Cox, R. H. Fungal Metabolites II; Academic Press: New York, 1983; 631 pp and references therein.
20. Nozawa, K.; Yuyama, M.; Nakajima, S.; Kawai, K.; Udagawa, S. J. Chem. Soc., Perkin Trans. 1 1988, 2155-2160.
21. Sater, H.; Steglich, W.; Anke, T. Angew. Chem., Int. Ed. 1999, 38, 1328-1349.
22. Dowd, P. F. Entomol. Exp. Appl. 1988, 47, 69-71.
23. Peterson, S. W.; Bayer, E. B.; Wicklow, D. T. Manuscript in preparation.