Boneratamides A-C, new sesquiterpenoids isolated from the marine sponge Axinyssa aplysinoides

Journal of Natural Products

Volumn 67, Issue 10, 2004, Pages 1752-1754

  Williams, David E ^a   Patrick, Brian O ^a   Tahir, Akbar ^b   Van Soest, Rob ^c   Roberge, Michel ^a   Andersen, Raymond J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b HASANUDDIN UNIVERSITY   (Indonesia)

^c UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BONERATAMIDE A; BONERATAMIDE A METHYL ESTER; BONERATAMIDE B; BONERATAMIDE B METHYL ESTER; BONERATAMIDE C; BONERATAMIDE C METHYL ESTER; ESTER DERIVATIVE; SESQUITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; AXINYSSA APLYSINOIDES; DRUG ISOLATION; DRUG STRUCTURE; SPECTROSCOPY; SPONGE (PORIFERA); STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ANIMALS; CRYSTALLOGRAPHY, X-RAY; INDONESIA; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; SESQUITERPENES;

AXINYSSA; PORIFERA;

EID: 7044233199     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np049798g     Document Type: Article

References (15)

1. Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2003, 20, 1-48.
2. For example, see: (a) Nieman, J. A.; Coleman, J. E.; Wallace, D. J.; Piers, E.; Lim, L. L.; Roberge, M.; Andersen, R. J. J. Nat. Prod. 2003, 66, 183-199. (b) Loganzo, F.; Discafani, C.; Annable, T.; Beyer, C.; Musto, S.; Tan, X.; Hardy, C.; Hernandez, R.; Baxter, M.; Singanallore, T.; Khafizova, G.; Poruchynsky, M. S.; Fojo, T.; Nieman, J. A.; Ayral-Kaloustian, S.; Zask, A.; Andersen, R. J.; Greenberger, L.M. Cancer Res. 2003, 63, 1838-1845.
3. For example, see: (a) Nieman, J. A.; Coleman, J. E.; Wallace, D. J.; Piers, E.; Lim, L. L.; Roberge, M.; Andersen, R. J. J. Nat. Prod. 2003, 66, 183-199. (b) Loganzo, F.; Discafani, C.; Annable, T.; Beyer, C.; Musto, S.; Tan, X.; Hardy, C.; Hernandez, R.; Baxter, M.; Singanallore, T.; Khafizova, G.; Poruchynsky, M. S.; Fojo, T.; Nieman, J. A.; Ayral-Kaloustian, S.; Zask, A.; Andersen, R. J.; Greenberger, L.M. Cancer Res. 2003, 63, 1838-1845.
4. ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Biochemistry 1996, 35, 243-250.
5. Mooberry, S. L.; Tien, G.; Hernandez, A. H.; Plubrukarn, A.; Davidson, B. S. Cancer Res. 1999, 59, 653-660.
6. Hood, H. A.; West, L. M.; Rouwe, B.; Northcote, P. T.; Berridge, M. V.; Wakefield, S. J.; Miller, J. H. Cancer Res. 2002, 62, 3356-3360.
7. Bai, R. L.; Cichacz, Z. A.; Herald, C. L.; Pettit, G. R.; Hamel, E. Mol. Pharmacol. 1993, 44, 757-766.
8. Bai, R.; Paull, K. D.; Herald, C. L.; Malspeis, L.; Pettit, G. R.; Hamel, E. J. Biol. Chem. 1991, 266, 15882-15889.
9. (a) Manzo, E.; van Soest, R.; Matainaho, L.; Roberge, M.; Andersen, R. J. Org. Lett. 2003, 5, 4591-4594.
10. (b) Williams, D. E.; Roberge, M.; Van Soest, R.; Andersen, R. J. J. Am. Chem. Soc. 2003, 125, 5296-5297.
11. Roberge, M.; Cinel, B.; Anderson, H. J.; Lim, L.; Jiang, X.; Xu, L.; Kelly, M. T.; Andersen, R. J. Cancer Res. 2000, 60, 5052-5058.
12. Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC 244783). Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
13. Uy, M. M.; Ohta, S.; Yanai, M.; Ohta, E.; Hirata, T.; Ikegami, S. Tetrahedron 2003, 59, 731-736.
14. (a) Caine, D.; Deutsch, H. J. Am. Chem. Soc. 1978, 100, 8030-8031.
15. (b) DiBlasio, B.; Fattorusso, E.; Magno, S.; Mayol, L.; Pedrone, C.; Santacroce, C.; Sica, D. Tetrahedron 1976, 32, 473-478.