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Publicly Available Published by De Gruyter January 1, 2009

Recent heterocyclic compounds from marine invertebrates: Structure and synthesis

  • Yoel Kashman , Amira Rudi and Doron Pappo

Abstract

A large variety of unique heterocyclic natural marine products, without terrestrial counterparts, have been isolated from marine invertebrates, mainly sponges, ascidians, and soft corals. Many of these compounds display interesting biological activity. In this review, we report our recent studies on nitrogen-containing heterocyclic compounds ("alkaloids"), as well as some containing sulfur and oxygen, which have been isolated from Red Sea and Indo-Pacific organisms, and discuss progress on the synthesis of these natural products and structural analogs.


Conference

International Symposium on Chemistry of Natural Products (ISCNP-25) and 5th International Conference on Biodiversity (ICOB-5), International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 25th, Kyoto, Japan, 2006-07-23–2006-07-28


References

1. D. J. Faulkner. Nat. Prod. Rep. 20, 1 (2003) and earlier reports in this series.Search in Google Scholar

2. J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, M. R. Prinsep. Nat. Prod. Rep. 22, 15 (2005) and earlier reports in the series.10.1039/b415080pSearch in Google Scholar PubMed

3. M. H. G. Munro, J. W. Blunt. Marine Literature Database, Dept. of Chemistry, University of Canterbury, New Zealand (2006).Search in Google Scholar

4. doi:10.1021/ja00206a029, Y. Kashman, S. Hirsch, O. J. McConnell, I. Ohtani, T. Kusumi. J. Am. Chem. Soc. 111, 8925 (1989).Search in Google Scholar

5. doi:10.1126/science.6681676, I. Spector, N. R. Shochet, Y. Kashman, A. Groweiss. Science 219, 493 (1983).Search in Google Scholar

6. doi:10.1021/jo00283a029, A. Rudi, Y. Kashman. J. Org. Chem. 54, 5331 (1989).Search in Google Scholar

7. S. Carmely, M. Cojocaru, Y. Loya, Y. Kashman. J. Org. Chem. 53, 4801 (1988) and refs. therein.10.1021/jo00255a026Search in Google Scholar

8. doi:10.1071/CH9930623, P. R. Berquist, B. F. Bowden, R. C. Cambie, P. A. Craw, P. Karuso, A. Poiner, W. C. Taylor. Aust. J. Chem. 46, 623 (1993).Search in Google Scholar

9. doi:10.1071/C96166, W. C. Taylor, S. Toth. Aust. J. Chem. 50, 895 (1997).Search in Google Scholar

10. doi:10.1016/j.tetlet.2005.09.047, A. Rudi, Y. Erez, Y. Benayahu, Y. Kashman. Tetrahedron Lett. 46, 8613 (2005).Search in Google Scholar

11. A. Rudi, G. Shmul, Y. Benayahu, Y. Kashman. Tetrahedron Lett. 47, 2937 (2006) and refs. therein.10.1016/j.tetlet.2006.02.118Search in Google Scholar

12. doi:10.1055/s-1996-4291, C. C. Lin, H. J. Wu. Synthesis 6, 715 (1996).Search in Google Scholar

13. doi:10.1021/ol036454t, L. Chill, A. Rudi, Y. Benayahu, M. Schleyer, Y. Kashman. Org. Lett. 6, 755 (2004).Search in Google Scholar

14. doi:10.1016/S0040-4020(01)91590-X, A. Groweiss, Y. Kashman. Tetrahedron 39, 3385 (1983).Search in Google Scholar

15. doi:10.1021/ol048358d, A. Rudi, Y. Benayahu, Y. Kashman. Org. Lett. 6, 4013 (2004).Search in Google Scholar

16. doi:10.1021/np50073a005, S. Hirsch, A. Rudi, Y. Kashman. J. Nat. Prod. 54, 92 (1991).Search in Google Scholar

17. S. Loya, R. Tal, Y. Kashman, A. Hizi. Antimicrob. Agents Chemother. 34, 2009 (1990).10.1128/AAC.34.10.2009Search in Google Scholar

18. doi:10.1021/ol034615n, L. Chill, M. Aknin, Y. Kashman. Org. Lett. 5, 2433 (2003).Search in Google Scholar

19. doi:10.1021/np9800405, G. R. Pettit, R. Tan, J. Xu, Y. Ichihara, M. D. Williams, M. R. Boyd. J. Nat. Prod. 61, 955 (1998).Search in Google Scholar

20. doi:10.1021/jo970091r, S. Fukuzawa, S. Matsunaga, N. Fusetani. J. Org. Chem. 62, 4484 (1997).Search in Google Scholar

21. N. Imamura, M. Nishijima, T. Takadera, K. Adachi, M. Sakai, H. Sano. J. Antibiot. 50, 8 (1997).10.7164/antibiotics.50.8Search in Google Scholar

22. doi:10.1246/cl.1979.1481, D. Uemura, Y. Toya, I. Watanabe, Y. Hirata. Chem. Lett. 12, 1481 (1979).Search in Google Scholar

23. K. Watanabe, K. Iguchi, K. Fujimori. Heterocycles 49, 269 (1998).10.3987/COM-98-S26Search in Google Scholar

24. doi:10.1016/S0040-4020(99)00803-0, R. Duran, E. Zubia, M. J. Ortega, S. Naranjo, J. Salva. Tetrahedron 55, 13225 (1999).Search in Google Scholar

25. doi:10.1016/j.tetlet.2004.08.137, L. Chill, A. Rudi, Y. Benayahu, Y. Kashman. Tetrahedron Lett. 45, 7925 (2004).Search in Google Scholar

26. doi:10.1021/jo980905j, B. R. Copp, J. Jompa, A. Tahir, C. M. Ireland. J. Org. Chem. 63, 8024 (1998).Search in Google Scholar

27. doi:10.1021/jo9721453, G. Koren-Goldshlager, M. Aknin, E. M. Gaydon, Y. Kashman. J. Org. Chem. 63, 4601 (1998).Search in Google Scholar

28. doi:10.1007/BF01960259, S. Kohmoto, O. J. McConnell, A. Wright. Experientia 44, 85 (1988).Search in Google Scholar

29. P. Di Donato, A. Napolitano, G. Prota. Biochim. Biophys. Acta 1571, 157 (2002).10.1016/S0304-4165(02)00212-XSearch in Google Scholar

30. doi:10.1016/S0040-4039(00)93476-2, A. C. Stierle, J. H. Cardellina II, F. L. Singleton. Tetrahedron Lett. 32, 4827 (1991).Search in Google Scholar

31. doi:10.1016/S0960-894X(99)00205-X, H. Susuki, K. Shindo, A. Ueno, T. Miura, M. Takei, M. Sakakibara, H. Fukamachi, J. Tanaka, T.Higa. Bioorg. Med. Chem. Lett. 9, 1361 (1999).Search in Google Scholar

32. doi:10.1039/a909360e, C. D. J. Boden, G. J. Pattenden. J. Chem. Soc., Perkin Trans. 1 875 (2000).Search in Google Scholar

33. X. Fu, J. Su, L. Xeng. Sci. China, Ser. B 43, 643 (2000).10.1007/BF02969512Search in Google Scholar

34. doi:10.1021/jo991425a, H. Vervoot, W. Fenical, R. Epitanio. J. Org. Chem. 65, 782 (2000).Search in Google Scholar

35. doi:10.1021/np020531w, A. Rudi, L. Chill, M. Aknin, Y. Kashman. J. Nat. Prod. 66, 575 (2003).Search in Google Scholar

36. doi:10.1016/S0040-4020(98)00801-1, A. Rudi, M. Aknin, E. M. Gaydou, Y. Kashman. Tetrahedron 54, 13203 (1998).Search in Google Scholar

37. P. Marfey. Carlsberg Res. Commun. 49, 591 (1984).10.1007/BF02908687Search in Google Scholar

38. doi:10.1021/np000383e, T. Evan, A. Rudi, M. Ilan, Y. Kashman. J. Nat. Prod. 64, 226 (2001).Search in Google Scholar

39. doi:10.1016/j.tetlet.2006.07.128, H. Sorek, A. Rudi, M. Aknin, E. Gaydou, Y. Kashman. Tetrahedron Lett. 47, 7237 (2006).Search in Google Scholar

40. doi:10.1021/jo00084a015, A. Rudi, I. Goldberg, Z. Stein, F. Frolow, Y. Benayahu, M. Schleyer, Y. Kashman. J. Org. Chem. 59, 999 (1994).Search in Google Scholar

41. doi:10.1021/np9905158, A. Rudi, T. Evan, M. Aknin, Y. Kashman. J. Nat. Prod. 63, 832 (2000).Search in Google Scholar

42. doi:10.1021/ja00305a027, R. A. Andersen, D. J. Faulkner, H. Cun-Heng, G. D. Van Duyne, J. Clardy. J. Am. Chem. Soc. 107, 5492 (1985).Search in Google Scholar

43. doi:10.1002/hlca.19920750525, W. Y. Voshida, K. K. Lee, A. R. Carroll, P. J. Scheuer. Helv. Chem. Acta 75, 1721 (1992).Search in Google Scholar

44. doi:10.1016/0040-4020(95)00568-S, A. Terpin, K. Polborn, W. Steglich. Tetrahedron 51, 9941 (1995).Search in Google Scholar

45. doi:10.1042/0264-6021:3440085, S. Loya, A. Rudi, Y. Kashman, A. Hizi. Biochem. J. 344, 85 (1999).Search in Google Scholar

46. doi:10.1021/np970442x, G. Koren-Goldshlager, Y. Kashman, M. Schleyer. Nat. Prod. 61, 282 (1998).Search in Google Scholar

47. doi:10.1016/S0040-4039(98)02467-8, Y. Kashman, G. Koren-Goldshlager, M. D. Garcia Gravalos, M. Schleyer. Tetrahedron Lett. 40, 997 (1999).Search in Google Scholar

48. doi:10.1016/S0040-4020(01)01020-1, M. R. Heinrich, Y. Kashman, P. Spiteller, W. Steglich. Tetrahedron 57, 9973 (2001).Search in Google Scholar

49. doi:10.1016/S0040-4039(00)96762-5, R. Sakai, S. Komoto, T. Higa, C. W. Jefford, C. Bernardinelli. Tetrahedron Lett. 28, 5493 (1987).Search in Google Scholar

50. doi:10.1016/j.tet.2003.02.005, R. M. Markus, W. Steglich, M. G. Bannel, Y. Kashman. Tetrahedron 59, 9239 (2003).Search in Google Scholar

51. J. C. Braekman, D. Daloze, R. Tarares, E. Hajdu, R. W. M. Van Soest. J. Nat. Prod. 63, 193 (2000) and refs. therein.10.1021/np990403gSearch in Google Scholar

52. doi:10.1021/jo00110a021, A. D. Patil, N. V. Kumar, W. C. Kokke, M. F. Bean, A. J. Freyer, C. De Brosse, S. Mai, A. Truneh, B. Carte, A. L. Breen, R. P. Hertzberg, R. K. Johnson, J. W. Westley, B. C. M. Potts. J. Org. Chem. 60, 1182 (1995).Search in Google Scholar

53. doi:10.1021/jo962084t, A. D. Patil, A. J. Freyer, P. B. Taylor, B. Carte, G. Zuber, R. K. Johnson, D. J. Faulkner. J. Org. Chem. 62, 1814 (1997).Search in Google Scholar

54. doi:10.1016/0040-4020(95)00082-J, E. Polagiano, S. Demarino, L. Minale, R. Riccio, F. Zollo, M. Iorizzi, J. B. Carte, C. Debitus, L.Lucarain, J. Provost. Tetrahedron 51, 3675 (1995).Search in Google Scholar

55. doi:10.1016/j.tet.2006.06.063, H. Sorek, A. Rudi, S. Gueta, F. Reyes, M. Jesus Martin, M. Aknin, E. Gaydou, J. Vacelet, Y.Kashman. Tetrahedron 62, 8838 (2006).Search in Google Scholar

56. doi:10.1021/np9902690, T. Yosief, A. Rudi, Y. Kashman. J. Nat. Prod. 63, 229 (2000).Search in Google Scholar

57. doi:10.1021/np049834b, A. Rudi, M. Aknin, E. Gaydou, Y. Kashman. J. Nat. Prod. 67, 1932 (2004).Search in Google Scholar

58. doi:10.1021/np50088a004, A. Rudi, Y. Kashman. J. Nat. Prod. 55, 1408 (1992).Search in Google Scholar

59. doi:10.1016/S0040-4039(01)01111-X, D. Pappo, A. Rudi, Y. Kashman. Tetrahedron Lett. 42, 5941 (2001).Search in Google Scholar

60. doi:10.1016/S0040-4020(03)01058-5, D. Pappo, Y. Kashman. Tetrahedron 59, 6493 (2003).Search in Google Scholar

61. doi:10.1021/jo048622g, D. Pappo, S. Shimony, Y. Kashman. J. Org. Chem. 70, 199 (2005).Search in Google Scholar

62. doi:10.2174/1385272033486648, N. Fusetani, S. Matsunaga. Curr. Org. Chem. 7, 945 (2003).Search in Google Scholar

63. doi:10.1021/ol0491787, N. Berer, A. Rudi, I. Goldberg, Y. Benayahu, Y. Kashman. Org. Lett. 6, 2543 (2004).Search in Google Scholar

64. doi:10.1021/ja050299r, D. Pappo, M. Vartanian, S. Lang, Y. Kashman. J. Am. Chem. Soc. 127, 7682 (2005).Search in Google Scholar

65. doi:10.1016/S0040-4039(97)10360-4, T. Nakazawa, T. Suzuki, M. Ishii. Tetrahedron Lett. 38, 8951 (1997).Search in Google Scholar

66. doi:10.1021/ol060075t, D. Pappo, Y. Kashman. Org. Lett. 8, 1177 (2006).Search in Google Scholar

Published Online: 2009-01-01
Published in Print: 2007-01-01

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