Isolation and characterization of diastereomers of discorhabdins H and K and assignment of absolute configuration to discorhabdins D, N, Q, S, T, and U

Journal of Natural Products

Volumn 73, Issue 10, 2010, Pages 1686-1693

  Grkovic, Tanja ^a,b   Pearce, A Norrie ^a   Munro, Murray H G ^c   Blunt, John W ^c   Davies Coleman, Michael T ^d   Copp, Brent R ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b NATIONAL CANCER INSTITUTE   (United States)

^c UNIVERSITY OF CANTERBURY   (New Zealand)

^d RHODES UNIVERSITY   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYDISCORHABDIN D; ALKALOID; DISCORHABDIN H; DISCORHABDIN K; DISCORHABDIN N; DISCORHABDIN Q; DISCORHABDIN S; DISCORHABDIN T; DISCORHABDIN U; PRIANOSIN D; UNCLASSIFIED DRUG; DISCORHABDIN B; PYRROLE DERIVATIVE; QUINOLONE DERIVATIVE; QUINONE DERIVATIVE; SPIRO COMPOUND; THIAZEPINE DERIVATIVE;

ARTICLE; CIRCULAR DICHROISM; DIASTEREOISOMER; DRUG STRUCTURE; MASS SPECTROMETRY; NEW ZEALAND; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPONGE (PORIFERA); ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; STEREOISOMERISM;

LATRUNCULIA;

ALKALOIDS; ANIMALS; MOLECULAR STRUCTURE; NEW ZEALAND; PORIFERA; PYRROLES; QUINOLONES; QUINONES; SPIRO COMPOUNDS; STEREOISOMERISM; THIAZEPINES;

EID: 77958521906     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np100443c     Document Type: Article

References (34)

1. Kobayashi, J., Cheng, J.-F., Ishibashi, M., Nakamura, H., Ohizumi, Y., Hirata, Y., Sasaki, T., Lu, H., and Clardy, J. Tetrahedron Lett. 1987, 28, 4939-4942
2. Perry, N. B., Blunt, J. W., McCombs, J. D., and Munro, M. H. G. J. Org. Chem. 1986, 51, 5476-5478
3. Perry, N. B., Blunt, J. W., and Munro, M. H. G. Tetrahedron 1988, 44, 1727-1734
4. Cheng, J.-F., Ohizumi, Y., Wälchli, M. R., Nakamura, H., Hirata, Y., Sasaki, T., and Kobayashi, J. J. Org. Chem. 1988, 53, 4621-4624
5. Kobayashi, J., Cheng, J.-F., Yamamura, S., and Ishibashi, M. Tetrahedron Lett. 1991, 32, 1227-1228
6. Wada, Y., Otani, K., Endo, N., Harayama, Y., Kamimura, D., Yoshida, M., Fujioka, H., and Kita, Y. Tetrahedron 2009, 65, 1059-1062
7. Perry, N. B., Blunt, J. W., Munro, M. H. G., Higa, T., and Sakai, R. J. Org. Chem. 1988, 53, 4127-4128
8. Copp, B. R., Fulton, K. F., Perry, N. B., Blunt, J. W., and Munro, M. H. G. J. Org. Chem. 1994, 59, 8233-8238
9. Blunt, J. W., Munro, M. H. G., Battershill, C. N., Copp, B. R., McCombs, J. D., Perry, N. B., Prinsep, M., and Thompson, A. M. New J. Chem. 1990, 14, 761-75
10. Yang, A., Baker, B. J., Grimwade, J., Leonard, A., and McClintok, J. B. J. Nat. Prod. 1995, 58, 1596-1599
11. Reyes, F., Martin, R., Rueda, A., Fernández, R., Montalvo, D., Gómez, C., and Sánchez-Puelles, J. J. Nat. Prod. 2004, 67, 463-465
12. Antunes, E. M., Beukes, D. R., Kelly, M., Samaai, T., Barrows, L. R., Marshall, K. M., Sincich, C., and Davies-Coleman, M. T. J. Nat. Prod. 2004, 67, 1268-1276
13. Hooper, G. J., Davies-Coleman, M. T., Kelly-Borges, M., and Coetzee, P. S. Tetrahedron Lett. 1996, 37, 7135-7138
14. Gunasekera, S. P., McCarthy, P. J., Longley, R. E., Pomponi, S. A., Wright, A. E., Lobkovsky, E., and Clardy, J. J. Nat. Prod. 1999, 62, 173-175
15. Dijoux, M.-G., Gamble, W. R., Hallock, Y. F., Cardellina, J. H., van Soest, R., and Boyd, M. R. J. Nat. Prod. 1999, 62, 636-637
16. Ford, J. and Capon, R. J. J. Nat. Prod. 2000, 63, 1527-1528
17. Gunasekera, S. P., Zuleta, I. A., Longley, R. E., Wright, A. E., and Pomponi, S. A. J. Nat. Prod. 2003, 66, 1615-1617
18. Lang, G., Pinkert, A., Blunt, J. W., and Munro, M. H. G. J. Nat. Prod. 2005, 68, 1796-1798
19. El-Naggar, M. and Capon, R. J. J. Nat. Prod. 2009, 72, 460-464
20. Grkovic, T. and Copp, B. R. Tetrahedron 2009, 65, 6335-6340
21. Jeon, J.-E., Na, Z., Jung, M., Lee, H.-S., Sim, C. J., Nahm, K., Oh, K.-B., and Shin, J. J. Nat. Prod. 2010, 73, 258-262
22. Na, M., Ding, Y., Wang, B., Tekwani, B. L., Schinazi, R. F., Franzblau, S., Kelly, M., Stone, R., Li, X.-C., Ferreira, D., and Hamann, M. T. J. Nat. Prod. 2010, 73, 383-378
23. D'Ambrosio, M., Guerriero, A., Chiasera, G., Pietra, F., and Tatò, M. Tetrahedron 1996, 52, 8899-8906
24. Grkovic, T., Ding, Y., Li, X.-C., Webb, V. L., Ferreira, D., and Copp, B. R. J. Org. Chem. 2008, 73, 9133-9136
25. Antunes, E. M., Copp, B. R., Davies-Coleman, M. T., and Samaai, T. Nat. Prod. Rep. 2005, 22, 62-72
26. Harayama, Y. and Kita, Y. Curr. Org. Chem. 2005, 9, 1567-1588
27. Urban, S., Hickford, S. J. H., Blunt, J. W., and Munro, M. H. G. Curr. Org. Chem. 2000, 4, 765-807
28. Alvarez, B., Bergquist, P. R., and Battershill, C. N. N. Z. J. Mar. Freshwater Res. 2002, 36, 151-184
29. The structure of discorhabdin K has been previously presented at a conference and is shown in a review. (24) The structural depiction of the alkaloid in the review unfortunately contains an error, with the inadvertent omission of the 5,8-thioether linkage.
30. Meissner, A. and Sørensen, O. W. Magn. Reson. Chem. 2001, 39, 49-52
31. H 3.07) and C-5 was 3.2 Hz.
32. The (arbitrary) depiction of configuration in the original report (12) of (-)-discorhabdin Q is therefore incorrect.
33. Grkovic, T., Kaur, B., Webb, V. L., and Copp, B. R. Bioorg. Med. Chem. Lett. 2006, 16, 1944-1946
34. Perry, N. B., Benn, M. H., Brennan, N. J., Burgess, E. J., Ellis, G., Galloway, D. J., Lorimer, S. D., and Tangney, R. S. The Lichenologist 1999, 31, 627-636