Discorhabdin P, a new enzyme inhibitor from a deep-water caribbean sponge of the genus Batzella

Journal of Natural Products

Volumn 62, Issue 1, 1999, Pages 173-175

  Gunasekera, Sarath P ^a   McCarthy, Peter J ^a   Longley, Ross E ^a   Pomponi, Shirley A ^a   Wright, Amy E ^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

CALCINEURIN; CASPASE; DISCORHABDIN C; DISCORHABDIN P; ENZYME INHIBITOR; PEPTIDASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CANCER CELL CULTURE; CENTRAL AMERICA; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HUMAN CELL; LEUKEMIA P 388; LUNG CARCINOMA; MOUSE; NONHUMAN; SPONGE (PORIFERA);

ANIMALS; ANTINEOPLASTIC AGENTS; CALCINEURIN; CASPASE 3; CASPASES; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR STRUCTURE; PORIFERA; QUINONES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPIRO COMPOUNDS; THIAZEPINES; TUMOR CELLS, CULTURED;

ANIMALIA; BATZELLA; PORIFERA;

EID: 0032956336     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np980293y     Document Type: Article

References (28)

1. Faulkner, D. J. J. Nat. Prod. Rep. 1998, 15, 113-158, and references therein.
2. Gunasekera, S. P.; McCarthy, P. J.; Kelly-Borges, M.; Lobkovsky, E.; Clardy, J. J. Am. Chem. Soc. 1996, 118, 8759-8760.
3. Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, M. H. G. J. Org. Chem. 1986, 51, 5476-5478.
4. Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, M. H. G. Tetrahedron 1988, 44, 1727-1734.
5. Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Higa, T.; Sakai, R. J. Org. Chem. 1988, 53, 4127-4128.
6. Blunt, J. W.; Munro, M. H. G.; Battershill, C. N.; Copp, B. R.; McCombs, J. D.; Perry, N. B.; Prinsep, M.; Thompson, A. M. New J. Chem. 1990, 14, 761-781.
7. Copp, B. R.; Fulton, K. F.; Perry, N. B.; Blunt, J. W.; Munro, M. H. G. J. Org. Chem. 1994, 59, 8233-8238.
8. Perry, N. B.; McCombs, J. D., Copp, B. R.; Rea, J.; Lill, R.; Major, D.; Andrew, C.; Fulton, K.; Linton, M.; Bringans, S.; Blunt, J.; Munro, M. The 37th Annual Meeting of the American Society of Pharmacognosy, University of California, Santa Cruz, CA, July 27-31, 1996, P28.
9. Kobayashi, J.; Cheng, J.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Hirata, Y.; Sasaki, T.; Lu, H.; Clardy, J. Tetrahedron Lett. 1987, 28, 4939-4942.
10. Kobayashi, J.; Cheng, J.; Yamamura, S.; Ishibashi, M. Tetrahedron Lett. 1991, 32, 1227-1228.
11. Yang, A.; Baker, B. J.; Grimwade, J.; Leonard, A.; McClintock, J. B. J. Nat. Prod. 1995, 58, 1596-1599.
12. Guerini, D. Biochem. Biophys. Res. Comm. 1997, 235, 271-275.
13. Liu, J.; Farmer, J. D.; Lane, W. S.; Friedman, J.; Weissman, I.; Schreiber, S. L. Cell 1991, 66, 807-815.
14. Patel, T.; Gores, G. J.; Kaufmann, S. H. FASEB J. 1996, 10, 587-597.
15. Schwartz, L. M.; Milligan, C. E. Trends Neurosci. 1996, 19, 555-562.
16. Milligan, C. E.; Prevette, D.; Yaginuma, H.; Homma, S.; Cardwell, C.; Fritz, L. C.; Tomaselli, K. J.; Oppenheim, R. W.; Schwartz, L. M. Neuron 1995, 15, 385-393.
17. Kerr, J. F. R.; Wyllie, A. H.; Currie, A. R. Br. J. Cancer 1972, 26, 239-257.
18. Hara, H.; Friedlander, R. M.;. Gagliardini, V.; Ayata, C.; Fink, K.; Huang, Z.; Shimizu-Sasamata, M.; Yuan, J.; Moskowitz, M. A. Proc. Natl. Acad. Sci. USA 1997, 94, 2007-2012.
19. Friedlander, R. M.; Brown, R. H.; Gagliardini V.; Wang, J.; Yuan, J. Nature 1997, 388, 31.
20. Kim, T.-W.; Pettingell, W. H.; Jung, Y.-K.; Kovacs, D. M.; Tanzi, R. E. Science 1997, 277, 373-376.
21. Sekine, C.; Yagita, H.; Kobata, T.; Hasunuma, T.; Nishioka, K.; Okumura, K. Biochem. Biophys. Res. Commun. 1996, 228, 14-20.
22. Radisky, D. C.; Radisky, E. S.; Barrows, L. R.; Copp, B. R.; Kramer, R. A.; Ireland, C. M. J. Am. Chem. Soc. 1993, 115, 1632-1638.
23. The correlations observed in the HMBC spectrum of 1 were: H-1 and H-5 [C-2, C-3, C-4, C-6, C-7, C-20]; H-7 [C-1, C-5, C-6, C-8, C-20]; H-8 [C-6, C-7, C-10]; H-14 [C-12, C-15, C-21, C-22]; H-16 [C-15, C-17, C-21]; H-17 [C-15, C-19]; H-22 [C-12, C-14].
24. A full list of crystallographic data and parameters for discorhabdin P has been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
25. van Soest, R. W. M.; Braekman, J.-C.; Faulkner, D. J.; Hajdu, E.; Harper, M. K; Vacelet, J. Bull. Inst. R. Sci. Nat. Belg. Biol. 1996, 66, 89-109.
26. Wallace, R. W.; Tallant, E. A.; Chung, W. Y. Methods Enzymol. 1983, 102, 39-47.
27. Tallant, E. A.; Wallace, R. W.; Chung, W. Y. Methods Enzymol. 1983, 102, 244-286.
28. Gunasekera, S. P.; McCarthy, P. J.; Pomponi, S. A.; Wright, A. E.; Longley, R. E. Serial number 09/122, 572, US patent filed on July 24, 1998.