Two pyrrolo[1, 2-a]azepine type alkaloids from stemona collinsae craib: Structure elucidations, relationship to asparagamine A, and a new biogenetic concept of their formation

Chemistry and Biodiversity

Volumn 1, Issue 2, 2004, Pages 265-279

  Seger, Christoph ^a,c   Mereiter, Kurt ^b   Kaltenegger, Elisabeth ^a   Pacher, Thomas ^a   Greger, Harald ^a   Hofer, Otmar ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^c UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AZEPINE DERIVATIVE; DIDEHYDROSTEMOFOLINE; FUSED HETEROCYCLIC RINGS; PLANT EXTRACT;

ARTICLE; BIOSYNTHESIS; CHEMISTRY; ISOLATION AND PURIFICATION; PLANT; STEMONACEAE;

ALKALOIDS; AZEPINES; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; PLANT COMPONENTS; PLANT EXTRACTS; STEMONACEAE;

EID: 7044247995     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200490023     Document Type: Article

References (37)

1. R. A. Pilli, M. C. Ferreira de Oliveira, Nat. Prod. Rep. 2000, 17, 117.
2. J.-F. Liao, C.-C. Shi, S.-Y. Chen, Y.-T. Fu, C.-F. Chen, J. Ethnopharmacology 1997, 57, 57.
3. E. A. Stöger, 'Arzneibuch der Chinesischen Medizin. Monographien des Arzneibuches der Volksrepublik China 1990 und 1995', Deutscher Apotheker Verlag Stuttgart, 1999.
4. H. Irie, N. Masaki, K. Ohno, K. Osaki, T. Taga, S. Uyeo, J. Chem. Soc., Chem. Commun. 1970, 1066.
5. S. Jiwajinda, N. Hirai, K. Watanabe, V. Santisopasri, N. Chuengsamarnyart, K. Koshimizu, H. Ohigashi, Phytochemistry 2001, 56, 693.
6. T. Sekine, F. Ikegami, N. Fukasawa, Y. Kashiwagi, T. Aizawa, Y. Fujii, N. Ruangrungsi, I. Murakoshi, J. Chem. Soc., Perkins Trans. 1 1995, 391.
7. T. Sekine, N. Fukasawa, Y. Kashiwagi, N. Ruangrungsi, I. Murakoshi, Chem. Pharm. Bull. 1994, 42, 1360.
8. W. Lin, R. Xu, Q. Zhong, Huaxue Xuebao 1991, 49, 1034.
9. B. Brem, C. Seger, T. Pacher, O. Hofer, S. Vajrodaya, H. Greger, J. Agric. Food Chem. 2002, 50, 6383.
10. E. Kaltenegger, B. Brem, K. Mereiter, H. Kalchhauser, H. P. Kählig, O. Hofer, S. Vajrodaya, H. Greger, Phytochemistry 2003, 63, 803.
11. I. Murakoshi, J. Fujii, Jap. Pat. 7330774, 1995 p. 1-6.;
12. S. Tip-Pyang, P. Tangpraprutgul, N. Wiboonpun, G. Veerachato, P. Phuwapraisirisan, Preecha, B. Sup-Udompol, ACGC Chem. Res. Commun. 2000, 12, 31.
13. A. S. Kende, T. L. Smalley, H. Huang, J. Am. Chem. Soc. 1999, 121, 7431.
14. Y. Ye, R. F. Velten, Tetrahedron Lett. 2003, 44, 7171.
15. S. C. Smith, P. D. Bentley, Tetrahedron Lett. 2002, 43, 899;
16. A. S. Kende, J. I. M. Hernando, J. B. J. Milbank, Tetrahedron 2002, 58, 61;
17. P. Wipf, S. R. Rector, H. Takahashi, J. Am. Chem. Soc. 2002, 124, 14848;
18. J. D. Ginn, A. Pawda, Org. Lett. 2002, 4, 1515;
19. Y. Morimoto, M. Iwahashi, T. Kinoshita, K. Nishida, Chem. Eur. J. 2001, 7, 4107;
20. D. R. Williams, M. G. Fromhold, J. D. Earley, Org. Lett. 2001, 3, 2721;
21. A. S. Kende, J. I. M. Hernando, J. B. J. Milbank, Org. Lett. 2001, 3, 2505;
22. P. A. Jacobi, K. Lee, J. Am. Chem. Soc. 2000, 122, 4295;
23. P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 117, 11106.
24. T. Pacher, C. Seger, S. Vajrodaya, O. Hofer, H. Greger, J. Nat. Prod. 2002, 65, 820.
25. H. D. Flack, G. Bernardinelli, J. Appl. Crystallogr. 2000, 33, 1143.
26. T. Sekine, N. Fukasawa, I. Murakoshi, N. Ruangrungsi, Phytochemistry 1997, 44, 763.
27. X. D. Cong, G. J. Xu, R. L. Jin, H. J. Zhi, Acta Pharm. Sin. (Yaoxue Xuebao) 1992, 27, 556.
28. D. Ober, T. Hartmann, PNAS 1999, 96, 14777.
29. D. S. Seigler, 'Plant Secondary Metabolism', Kluwer Academic Publishers, Boston, Dortrecht, London, 1995, pp. 519, pp. 549.
30. D. Ober, L. Gibas, L. Witte, T. Hartmann, Phytochemistry 2003, 62, 339.
31. S. Weber, W. Eisenreich, A. Bacher, T. Hartmann, Phytochemistry 1999, 50, 1005.
32. Bruker, Programs SMART, version 5.054;
33. SAINT, version 6.2.9;
34. SADABS version 2.03;
35. XPREP, version 5.1;
36. SHELXTL, version 5.1. Bruker AXS Inc., Madison, WI, USA, 2001
37. G. M. Sheldrick, SHELX-97, Release 2. ASystem of Computer Programs for Crystal Structure Determination, University of Göttingen, Germany, 1997.