Dysidiolide: A novel protein phosphatase inhibitor from the Caribbean sponge Dysidea etheria de Laubenfels

Journal of the American Chemical Society

Volumn 118, Issue 36, 1996, Pages 8759-8760

  Gunasekera, Sarath P ^a   McCarthy, Peter J ^a   Kelly Borges, Michelle ^a   Lobkovsky, Emil ^b   Clardy, Jon ^b  

^a FLORIDA ATLANTIC UNIVERSITY   (United States)

^b Department of Molecular Biology and Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYSIDIOLIDE; ENZYME INHIBITOR; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SPONGE; X RAY ANALYSIS;

EID: 0029816291     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961961+     Document Type: Article

References (27)

1. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223-269; 1994, 11, 355-394; 1993, 10, 497-539; 1992, 9, 323-364; 1991, 8, 97-147; 1990, 7, 269-309; 1988, 5, 613-663; 1987, 4, 539-576; 1986, 3, 1-33; 1984. 1, 551-598.
2. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223-269; 1994, 11, 355-394; 1993, 10, 497-539; 1992, 9, 323-364; 1991, 8, 97-147; 1990, 7, 269-309; 1988, 5, 613-663; 1987, 4, 539-576; 1986, 3, 1-33; 1984. 1, 551-598.
3. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223-269; 1994, 11, 355-394; 1993, 10, 497-539; 1992, 9, 323-364; 1991, 8, 97-147; 1990, 7, 269-309; 1988, 5, 613-663; 1987, 4, 539-576; 1986, 3, 1-33; 1984. 1, 551-598.
4. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223-269; 1994, 11, 355-394; 1993, 10, 497-539; 1992, 9, 323-364; 1991, 8, 97-147; 1990, 7, 269-309; 1988, 5, 613-663; 1987, 4, 539-576; 1986, 3, 1-33; 1984. 1, 551-598.
5. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223-269; 1994, 11, 355-394; 1993, 10, 497-539; 1992, 9, 323-364; 1991, 8, 97-147; 1990, 7, 269-309; 1988, 5, 613-663; 1987, 4, 539-576; 1986, 3, 1-33; 1984. 1, 551-598.
6. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223-269; 1994, 11, 355-394; 1993, 10, 497-539; 1992, 9, 323-364; 1991, 8, 97-147; 1990, 7, 269-309; 1988, 5, 613-663; 1987, 4, 539-576; 1986, 3, 1-33; 1984. 1, 551-598.
7. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223-269; 1994, 11, 355-394; 1993, 10, 497-539; 1992, 9, 323-364; 1991, 8, 97-147; 1990, 7, 269-309; 1988, 5, 613-663; 1987, 4, 539-576; 1986, 3, 1-33; 1984. 1, 551-598.
8. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223-269; 1994, 11, 355-394; 1993, 10, 497-539; 1992, 9, 323-364; 1991, 8, 97-147; 1990, 7, 269-309; 1988, 5, 613-663; 1987, 4, 539-576; 1986, 3, 1-33; 1984. 1, 551-598.
9. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223-269; 1994, 11, 355-394; 1993, 10, 497-539; 1992, 9, 323-364; 1991, 8, 97-147; 1990, 7, 269-309; 1988, 5, 613-663; 1987, 4, 539-576; 1986, 3, 1-33; 1984. 1, 551-598.
10. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223-269; 1994, 11, 355-394; 1993, 10, 497-539; 1992, 9, 323-364; 1991, 8, 97-147; 1990, 7, 269-309; 1988, 5, 613-663; 1987, 4, 539-576; 1986, 3, 1-33; 1984. 1, 551-598.
11. Millar, J. B. A.; Russell, P. Cell 1992, 68, 407-410.
12. Baratte, B.; Meijer, L.; Galatnikov, K.; Beach, D. Anticancer Res. 1992, 12, 873-880.
13. -1.
14. 6) δ 0.81 (3H, d, J = 6.7 Hz, H-23), 0.93 (3H, s. H-22), 1.51(3H, br s, H-24) 1.62 (3H, s. H-20), 4.38, (4.51) (1H, dt, J = 5.7, 8.6 Hz, H-4), 4.60, 4.63 (2H, 2s, H-21), 5.12, (5.23) (1H, d, J = 5.7 Hz, 4-OH), 5.91 (1H, s, H-2), 6.08 (1H, d, J = 6.0 Hz, H-25), 7.80 (1H, d, J = 6.0 Hz, 25-OH).
15. 6) δ 14.9 (q, C-23), 21.5 (br), 21.6 (t), 21.7 (t), 22.0 (q, C-20), 22.0 (q, C-24), 23.5 (br), 25.9 (q, C-22), 27.0 (br), 29.8 (br), 31.0 (br), 33.0 (d, C-7), 36.6 (br), 37.9 (t), 39.0 (br), 41.0 (br), 63.0, (64.4) (d, C-4), 97.6, (98.1) (d, C-25), 110.0 (t. C-21), 115.5 (d, C-9), 115.9, (116.2) (d, C-2), 142.3 (s, C-10), 145.3 (s, C-19), 170.4, (170.5) (s, C-1), 173.5, (175.5) (s, C-3).
16. Results from HMQC and HMBC NMR experiments were used to assign the respective carbon signals.
17. (a) Nakagawa, M.; Ishihama, M.; Hamamoto, Y.; Endo, M. Abstracts of Papers, 28th Symposium on the Chemistry of Natural Products; Pharmaceutical Institute, Tohoku University: Sendai, Japan, October 1986; p 200.
18. (b) Chem. Abstr. 1987, 106, 96126b.
19. Yunker, M. B.; Scheuer, P. J. J. Am. Chem. Soc: 1978, 100, 307-309.
20. De Silva, E. D.; Scheuer, P. J. Tetrahedron Lett. 1981, 22, 3147-3150.
21. Kernan, M. R.; Faulker, D. J.; Jacobs, R. S. J. Org. Chem. 1987, 52, 3081-3083.
22. Albizati, K. F.; Holman, T.; Faulker, D. J.; Glaser, K. B.; Jacobs, R. S. Experientia 1987, 43, 949-950.
23. Sullivan, B.; Faulkner, D. J. Tetrahedron Lett. 1982, 23, 907-910.
24. Puliti, R.; De Rosa, S.; Mattia, C. A.; Mazzarella, L. Acta Crystallogr., Sect. C 1990, 46, 1533-1536.
25. Crews, P.; Jiménez, C.; O'Neil-Johnson, M. Tetrahedron 1991, 47, 3585-3600.
26. Butler, M. S.; Capon, R. J. Aust. J. Chem. 1992, 45, 1705-1743.
27. 3 The assay (U.S. Patent 5,294,538 assigned to Mitotix, Inc., Cambridge, MA) is used by Harbor Branch Oceanographic Institution under license from Mitotix.