Viscosalines B 1,2 and E 1,2: Challenging new 3-alkyl pyridinium alkaloids from the marine sponge Haliclona viscosa

Chemistry - A European Journal

Volumn 18, Issue 26, 2012, Pages 8180-8189

  Schmidt, Gesine ^a   Timm, Christoph ^a   Grube, Achim ^a   Volk, Christian A ^a   Köck, Matthias ^a  

^a ALFRED WEGENER INSTITUTE FOR POLAR AND MARINE RESEARCH   (Germany)

Author keywords

alanine; alkaloids; in source collision induced dissociation; mass spectrometry; natural products; total synthesis

Indexed keywords

ALKALOIDS; CHROMATOGRAPHIC METHODS; COLLISION-INDUCED DISSOCIATION; EXPERIMENTAL CONDITIONS; ION TRAP MASS SPECTROMETER; ION TRAPS; ISOMERIC COMPOUNDS; MARINE SPONGE; NATURAL PRODUCTS; PYRIDINIUM; SPECTROMETRIC METHODS; STRUCTURAL ISOMERS; STRUCTURE ELUCIDATION; SYNTHETIC COMPOUNDS; TIME-OF-FLIGHT MASS SPECTROMETERS; TOTAL SYNTHESIS;

AMINO ACIDS; CHROMATOGRAPHIC ANALYSIS; DISSOCIATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETERS; MASS SPECTROMETRY; METABOLITES; NITROGEN COMPOUNDS; OPTIMIZATION;

ISOMERS;

ALKALOID; PYRIDINIUM DERIVATIVE; VISCOSALINE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HALICLONA; ISOLATION AND PURIFICATION; MARINE BIOLOGY;

ALKALOIDS; ANIMALS; HALICLONA; MARINE BIOLOGY; MOLECULAR STRUCTURE; PYRIDINIUM COMPOUNDS;

EID: 84862575886     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101362     Document Type: Article

References (33)

1. R. J. Andersen, R. W. M. van Soest, F. Kong, in Alkaloids: Chemical and Biological Perspectives, Vol. 10, 1 st ed., (Ed.: S. W. Pelletier,), Pergamon Press, 1996, pp. 301-355
2. T. Turk, K. Sepčić, I. Mancini, G. Guella, in Studies in Natural Products, Vol. 35 (Ed.:, Atta-ur-Rahman,), Elsevier, 2008, pp. 355-397.
3. G. Cimino, S. De Stefano, G. Scognamiglio, G. Sodano, E. Trivellone, Bull. Soc. Chim. Belg. 1986, 95, 783-800
4. R. Sakai, T. Higa, C. W. Jefford, G. Bernardinelli, J. Am. Chem. Soc. 1986, 108, 6404-6405
5. R. Sakai, S. Kohmoto, T. Higa, C. W. Jefford, G. Bernardinelli, Tetrahedron Lett. 1987, 28, 5493-5496
6. M. T. Davies-Coleman, D. J. Faulkner, G. M. Dubowchik, G. P. Roth, C. Polson, C. Fairchild, J. Org. Chem. 1993, 58, 5925-5930
7. K. Sepčić, G. Guella, I. Mancini, F. Pietra, M. Dalla Serra, G. Menestrina, K. Tubbs, P. Maček, T. Turk, J. Nat. Prod. 1997, 60, 991-996
8. C. A. Volk, M. Köck, Org. Lett. 2003, 5, 3567-3569
9. C. A. Volk, M. Köck, Org. Biomol. Chem. 2004, 2, 1827-1830.
10. T. Ichiba, R. Sakai, S. Kohmoto, G. Saucy, Tetrahedron Lett. 1988, 29, 3083-3086
11. M. Tsuda, N. Kawasaki, J. Kobayashi, Tetrahedron Lett. 1994, 35, 4387-4388
12. M. Tsuda, K. Inaba, N. Kawasaki, K. Honma, J. Kobayashi, Tetrahedron 1996, 52, 2319-2324
13. D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692
14. J.-F. Hu, M. T. Hamann, R. T. Hill, M. Kelly, in The Alkaloids: Chemistry and Biology, Vol. 60 (Ed.:, G. A. Cordell,), Elsevier, 2003, pp. 207-285
15. J. Peng, K. V. Rao, Y.-M. Choo, M. T. Hamann, in Modern Alkaloids-Structure, Isolation, Synthesis and Biology (Eds.:, E. Fattorusso, O. Taglialatela-Scafati,), Wiley-VCH, Weinheim, 2008.
16. J. Kobayashi, M. Tsuda, N. Kawasaki, K. Matsumoto, T. Adachi, Tetrahedron Lett. 1994, 35, 4383-4386.
17. F. J. Schmitz, K. H. Hollenbeak, D. C. Campbell, J. Org. Chem. 1978, 43, 3916-3922.
18. N. Fusetani, K. Yasumuro, S. Matsunaga, Tetrahedron Lett. 1989, 30, 6891-6894
19. C. A. Volk, H. Lippert, E. Lichte, M. Köck, Eur. J. Org. Chem. 2004, 3154-3158
20. G. Schmidt, C. Timm, M. Köck, Org. Biomol. Chem. 2009, 7, 3061-3064
21. C. Cychon, G. Schmidt, T. Mordhorst, M. Köck, Z. Naturforsch. B 2012, in press.
22. N. Fusetani, N. Asai, S. Matsunaga, K. Honda, K. Yasumuro, Tetrahedron Lett. 1994, 35, 3967-3970
23. N. Oku, K. Nagai, N. Shindoh, Y. Terada, R. W. M. van Soest, S. Matsunaga, N. Fusetani, Bioorg. Med. Chem. Lett. 2004, 14, 2617-2620
24. J. H. H. L. de Oliveira, A. Grube, M. Köck, R. G. S. Berlinck, M. L. Macedo, A. G. Ferreira, E. Hajdu, J. Nat. Prod. 2004, 67, 1685-1689.
25. Due to the presence of more than one compound in the structural class of the viscosalines, the compound was renamed viscosaline C according to the cyclostellettamine nomenclature (C=13/13).
26. A. Grube, C. Timm, M. Köck, Eur. J. Org. Chem. 2006, 1285-1295
27. G. Schmidt, C. Timm, A. Grube, E. Lichte, E. Cuny, M. Reggelin, M. Köck, unpublished results.
28. G. Schmidt, C. Timm, M. Köck, Z. Naturforsch. B: J. Chem. Sci. 2011, 66, 745-748.
29. C. Timm, C. Volk, F. Sasse, M. Köck, Org. Biomol. Chem. 2008, 6, 4036-4040.
30. B. J. Shorey, V. Lee, J. E. Baldwin, Tetrahedron 2007, 63, 5587-5592.
31. N. Meyer, W. Wykypiel, D. Seebach, Org. Syn. Coll. Vol. 1988, 6, 342-348
32. S. Youssif, ARKIVOC 2001, 242-268.
33. C. Timm, PhD thesis, Johann Wolfgang Goethe-Universität (Frankfurt am Main), 2007.