Three new alkaloids from the marine tunicate Cystodytes violatinctus

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4601-4603

  Koren Goldshlager, Ganit ^a   Aknin, Maurice ^b   Gaydou, Emile M ^c   Kashman, Yoel ^a  

^a TEL AVIV UNIVERSITY   (Israel)

^b Alleé des Aigues Marines   (France)

^c Univ de Droot   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; ALKALOID DERIVATIVE; SHERMILAMINE D; SHERMILAMINE E; TINTAMINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; AQUATIC FLORA; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; MADAGASCAR; NONHUMAN; TUMOR; VIRUS INFECTION;

EID: 0032504082     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9721453     Document Type: Article

References (25)

1. Davidson, B. S. Chem. Rev. 1993, 93, 1793.
2. Faulkner J. D. J. Nat Prod. Rep. 1997, 14, 259 and earlier reports in this series.
3. (a) Kobayashi, J.; Cheng, J.; Walchli, M. R.; Nakamura, H.; Mirata, Y.; Sasaki, T.; Ohnizumi, Y. J. Org. Chem. 1988, 53, 1800.
4. (b) Kobayashi, J.; Tsuda, M.; Tanabe, A.; Ishibashi, M.; Cheng, J.; Yamamura, S.; Sasaki, T. J. Nat. Prod. 1991, 54, 1634.
5. (c) Bontemps, N.; Bonnard, I.; Banaigs. B.; Combaut, G.; Francisco, C. Tetrahedron Lett. 1994, 35, 7023.
6. (d) Kobayashi, J.; Cheng, J.; Ohta, T.; Nozoe, S.; Ohizumi, Y.; Sasaki, T. J. Org. Chem. 1990, 50, 3666.
7. (e) Kobayashi, J. New. J. Chem. 1990, 14, 741.
8. Rudi, A.; Kashman, Y. J. Org. Chem. 1989, 54, 5331.
9. (a) Cooray, N. M.; Scheuer, P. J.; Parakanyi, L.; Clardy, J. J. Org. Chem. 1988, 53, 4619.
10. (b) Carroll, A. R.; Cooray, N. M.; Poiner, A.; Scheuer, P. J. J. Org. Chem. 1989, 54, 4231.
11. Molinsky, T. F. Chem. Rev. 1993, 93, 1825.
12. We have most recently isolated the same six alkaloids from a Eudistoma sp collected in the Dahlak archipelago, near Eritrea, the Red Sea.
13. Fusetani, N. Biorganic Marine Chemistry; Springer-Verlag: Berlin, 1987; Vol. 1, p 61.
14. H 3.2s.
15. 4,7
16. 13C chemical shifts agreed well with a 3-alkyl-4-aminophenol; i.e.: Cimino, G.; Crispino, A.; De Rosa, S.; De Stefano, S.; Gavagnin, M.; Sodano, G. Tetrahedron 1987, 43, 4023.
17. 13C chemical shifts of partial structure c were in good agreement with this part in eudistone A. He, H.; Faulkner, D. J. J. Org. Chem. 1991, 56, 5369.
18. H-11, being most likely further coupled to the vicinal acidic OH(12) proton, in the enol-tautomeric structure, gives rise to a broadened signal.
19. C 176.2 (s, C-1), 157.4 (s, C-2), 112.7 (d, C-3), 129.9 (d, C-4), 123.5 (d, C-5), 136.2 (d, C-6), 136.7 (d, C-7) were measured for 2-amino-tropones: Bagli, L. F.; St-Jacques, M. Can. J. Chem. 1978, 56, 578.
20. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. In Spectrometric Identification of Organic Compounds, 5th ed.; Wiley-Interscience: Singapore, 1991; p 240.
21. CH 162 (C-5/H-5), 160 (C-7/H-7) were measured for 2-methoxytropones; Bagli, L. F.; St-Jacques, M. Can. J. Chem. 1978, 56, 578.
22. (a) Gellerman, G.; Rudi, A.; Kashman, Y. Tetrahedron Lett. 1993, 34, 1823.
23. (b) Gellerman, G.; Rudi, A.; Kashman, Y. Tetrahedron 1994, 50, 1259.
24. Chill, L.; Kashman, Y. Tetrahedron 1997, 53, 16147.
25. Dyeing Reagents for Thin Layer and Paper Chromatography; E. Merck: Darmstadt, Germany, 1971.