New sesquiterpene and brominated metabolites from the tropical marine sponge Dysidea sp.

Tetrahedron

Volumn 56, Issue 29, 2000, Pages 5247-5252

  Cameron, George M ^a   Stapleton, Bronwin L ^a   Simonsen, Shane M ^a   Brecknell, Douglas J ^a   Garson, Mary J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Alkaloids; Bromophenols; NMR; Sponges; Terpenes

Indexed keywords

SESQUITERPENE DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; METABOLITE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SPONGE (PORIFERA); STEREOCHEMISTRY; STRUCTURE ANALYSIS; TAXONOMY;

EID: 0034647732     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00434-8     Document Type: Article

References (54)

1. Faulkner, D. J. Nat. Prod. Rep. 1999, 16, 155 and earlier articles in this review series.
2. Spirolactols/lactones: (a) Kazlauskas, R.; Murphy, P. T.; Wells, R. J. Tetrahedron Lett. 1978, 4949.
3. (b) Charles, C.; Braekman, J. C.; Daloze, D.; Tursch, B.; Declerq, J. P.; Germain, G.; van Meerscche, M. Bull. Soc. Chim. Belg. 1978, 87, 481.
4. (c) Schram, T. J.; Cardellina, J. H. J. Org. Chem. 1985, 50, 4155.
5. Other sesquiterpenes: (a) Sarma, N. S.; Rambabu, M.; Anjaneyulu, A. S. R.; Rao, C. B. S.; Saito, I. Ind. J. Chem. 1986, 25B, 1001.
6. (b) Venkateswarlu, V.; Farooq Biabani, M. A.; Venkat Rami Reddy, M.; Chavakula, R.; Venkateswara Rao, J. J. Nat. Prod. 1994, 57, 827.
7. (c) Sera, Y.; Adachi, K.; Nishida, F.; Shizuri, Y. J. Nat. Prod. 1999, 62, 395.
8. Furodysin/furodysinin skeleton: (a) Kaslauskas, R.; Murphy, P. T.; Wells, R. J.; Daly, J. J.; Schönholzer, P. Tetrahedron Lett. 1978, 4951.
9. (b) Dunlop, R. W.; Kazlauskas, R.; March, G.; Murphy, P. T.; Wells, R. J. Aust. J. Chem. 1982, 35, 95.
10. (c) Guella, G.; Mancini, I.; Guerriero, A.; Pietra, F. Helv. Chim. Acta 1985, 68, 1276.
11. (d) Capon, R. J.; MacLeod, J. K. J. Nat. Prod. 1987, 50, 1136.
12. (e) van Altena, I. A.; Millar, D. A. Aust. J. Chem. 1989, 42, 2181.
13. (f) Ksebati, M.; Schmitz, F. J. J. Nat. Prod. 1988, 51, 857.
14. (g) Searle, P. A.; Jamal, N. M.; Lee, G. M.; Molinski, T. F. Tetrahedron 1994, 50, 3879.
15. Lactones and autoxidised derivatives of furodysinin/furodysin: (a) Grode, S. H.; Cardellina, J. H. J. Nat. Prod. 1984, 47, 76.
16. (b) Carte, B.; Kernan, M. R.; Barrabee, E. B.; Faulkner, D. J.; Matsumoto, G. K.; Clardy, J. J. Org. Chem. 1986, 51, 3528.
17. (c) Carte, B.; Mong, S.; Poehland, B.; Sarau, H.; Westley, J. W.; Faulkner, D. J. Tetrahedron Lett. 1989, 30, 2725.
18. (d) Horton, P.; Inman, W. D.; Crews, P. J. Nat. Prod. 1990, 53, 143.
19. Modified sterols: (a) Delseth, C.; Tolela, L.; Scheuer, P. J.; Wells, R. J.; Djerassi C. Helv. Chim. Acta 1979, 62, 101.
20. (b) Capon, R. J.; Faulkner, D. J. J. Org. Chem. 1985, 50, 4771.
21. (c) Rambabu, M.; Saram, N. S. Ind. J. Chem. 1987, 26B, 1156.
22. (d) West, R. R.; Cardellina, J. H. J. Org. Chem. 1988, 53, 2782.
23. (e) West, R. R.; Cardellina, J. H. J. Org. Chem. 1989, 54, 3234.
24. (f) Kobayashi, M.; Krishna, M. M.; Ishida, K.; Ayaneyulu, V. Chem. Pharm. Bull. 1992, 40, 72.
25. Recent references to chlorinated alkaloids include: (a) Clark, W. D.; Crews P. Tetrahedron Lett. 1995, 36, 1185.
26. (b) Dumdei, E. J.; Simpson, J. S.; Garson, M. J.; Byriel, K. S.; Kennard, C. H. L. Aust. J. Chem. 1997, 50, 139.
27. (c) Fu, X.; Zeng, L.-M.; Su, J.-Y.; Pais, M. J. Nat. Prod. 1997, 60, 695.
28. (d) Fu, X.; Ferreira, M. L. G.; Schmitz, F. J.; Kelly-Borges, M. J. Nat. Prod. 1998, 61, 1226.
29. (e) J. B. MacMillan, T. F. Molinski, J. Nat. Prod. 2000, 63, 155.
30. Bromophenols: (a) Sharma, G. M.; Vig, B. Tetrahedron Lett. 1972, 1715.
31. (b) Norton, R. S.; Wells, R. J. Tetarhedron Lett. 1980, 21, 3801.
32. (c) Carte, B.; Faulkner, D. J. Tetrahedron 1981, 37, 2335.
33. (d) Norton, R. S.; Croft, K. D.; Wells, R. J. Tetrahedron 1981, 37, 2341.
34. (e) Salva. J.; Faulkner, D. J. J. Nat. Prod. 1990, 53, 757.
35. (f) Fu, X.; Schmitz, F. J.; Govindan, M.; Abbas, S. A.; Hanson, K. M.; Horton, P. A.; Crews, P.; Laney, M.; Schatzman, R. C. J. Nat. Prod. 1995, 58, 1384.
36. (g) Anjaneyulu, V.; Nageswara Rao, K.; Radhika, P.; Muralikrishna, M.; Connelly, J. D. Ind. J. Chem. 1996, 35B, 89.
37. (h) Fu, X.; Schmitz, F. D. J. Nat. Prod. 1996, 59, 1102.
38. (i) Handayani, D.; Edrada, R. A.; Proksch, P.; Wray. V.; Witte, L.; Van Soest, R. W. M.; Kunzmann, A.; Soedarsono J. Nat. Prod. 1997, 60, 1313.
39. Isolated reports of terpenes from sponge specimens originally classified as Dysidea herbacea: (a) Kashman, Y.; Zviely, M. Tetrahedron Lett. 1979, 3879.
40. (b) Kashman, Y.; Zviely, M. Experientia 1980, 36, 1279.
41. Miscellaneous reports of amino acid-derived metabolites include: (a) Bandaranayake, W. M.; Berris, J. E.; Bourne, D. J. Comp. Biochem. Physiol. 1996, 115, 281.
42. (b) Sakai, R.; Kamiya, H.; Murata, M.; Shimamoto, K. J. Am. Chem. Soc. 1997, 119, 4112.
43. (a) Berthold, R. J.; Borowitzka, M. A.; Mackay, M. A. Phycologia 1982, 21, 327.
44. (b) Larkum, A. W. D.; Cox, G. C.; Hiller, R. G.; Parry, D. L.; Dibbayawan, T. P. Mar. Biol. 1987, 95, 1-13.
45. (a) Faulkner, D. J.; He, H.; Unson, M. D.; Bewley, C. A.; Garson, M. J. Gazz. Chim. Ital. 1993, 123, 301.
46. (b) Unson, M. D.; Faulkner, D. J. Experientia 1993, 49, 349.
47. (c) Flowers, A. E.; Garson, M. J.; Webb, R. I.; Dumdei, E. J.; Charan, R. D. Cell. Tiss. Res. 1998, 292, 597.
48. Unson M.D., Holland N.D., Faulkner D.J. Mar. Biol. 119:1994;1.
49. (a) Richou, O.; Vaillancourt, V.; Faulkner, D. J.; Albizati, K. F. J. Org. Chem. 1989, 54, 4729.
50. (b) Vaillancourt, V.; Agharahimi, M. R.; Sundram, U. N.; Richou, O.; Faulkner, D. J.; Albizati, K. F. J. Org. Chem. 1991, 56, 378.
51. Allinger N.L., Yuh Y.H., Lii J.-H. J. Am. Chem. Soc. 111:1989;8551.
52. Haasnoot C.A.G., De Leeuw F.A.A.M., Altona C. Tetrahedron. 36:1980;2783.
53. Trousdale E.K., Taylor S.W., Parkin S., Hope H., Molinski T.F. Nat. Prod. Lett. 12:1998;61.
54. Flowers A.E., Garson M.J., Byriel K.S., Kennard C.H.L., Aust. J. Chem. 51:1998;195.