Trikentramides A-D, indole alkaloids from the Australian sponge Trikentrion flabelliforme

Journal of Natural Products

Volumn 76, Issue 11, 2013, Pages 2100-2105

  Khokhar, Shahan ^a   Feng, Yunjiang ^a   Campitelli, Marc R ^a   Quinn, Ronald J ^a   Hooper, John N A ^a,b   Ekins, Merrick G ^b   Davis, Rohan A ^a  

^a GRIFFITH UNIVERSITY   (Australia)

^b QUEENSLAND MUSEUM   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; INDOLE ALKALOID; NATURAL PRODUCT; TRIKENTRAMIDE A; TRIKENTRAMIDE B; TRIKENTRAMIDE C; TRIKENTRAMIDE D; UNCLASSIFIED DRUG;

ARTICLE; AUSTRALIA; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COMPARATIVE STUDY; DENSITY FUNCTIONAL THEORY; EXTRACT; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; MOLECULAR MECHANICS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM MECHANICS; SOLID PHASE EXTRACTION; SPONGE (PORIFERA); TRIKENTRION FLABELLIFORME; TRIKENTRION SPONGE EXTRACT;

ANIMALS; AUSTRALIA; INDOLE ALKALOIDS; MARINE BIOLOGY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION; PORIFERA;

EID: 84888377929     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np400617h     Document Type: Article

References (36)

1. Gul, W.; Hamann, M. T. Life Sci. 2005, 78, 442-453
2. Blunt, J. W.; Copp, B. R.; Keyzers, R. A.; Munro, M. H. G.; Prinsep, M. R. Nat. Prod. Rep. 2012, 29, 144-222
3. Capon, R. J.; Macleod, J. K.; Scammells, P. J. Tetrahedron 1986, 42, 6545-6550
4. Loukaci, A.; Guyot, M. Tetrahedron Lett. 1994, 35, 6869-6872
5. Aknin, M.; Miralles, J.; Kornprobst, J.-M.; Faure, R.; Gaydou, E.-M.; Boury-Esnault, N.; Kato, Y.; Clardy, J. Tetrahedron Lett. 1990, 31, 2979-2982
6. Herb, R.; Carroll, A. R.; Yoshida, W. Y.; Scheuer, P. J.; Paul, V. J. Tetrahedron 1990, 46, 3089-3092
7. Camp, D.; Davis, R. A.; Campitelli, M.; Ebdon, J.; Quinn, R. J. J. Nat. Prod. 2012, 75, 72-81
8. Wright, A. E. In Natural Products Isolation Methods in Biotechnology; Cannell, R. J. P., Ed.; Humana Press: NJ, 1998; Vol. 4, pp 365-408.
9. Feng, Y.; Davis, R. A.; Sykes, M. L.; Avery, V. M.; Quinn, R. J. Bioorg. Med. Chem. Lett. 2012, 22, 4873-4876
10. Davis, R. A.; Duffy, S.; Avery, V. M.; Camp, D.; Hooper, J. N. A.; Quinn, R. J. Tetrahedron Lett. 2010, 51, 583-585
11. Rudolph, K. E.; Liberio, M. S.; Davis, R. A.; Carroll, A. R. Org. Biomol. Chem. 2013, 11, 261-270
12. Liberio, M. S.; Sooraj, D.; Williams, E. D.; Feng, Y.; Davis, R. A. Tetrahedron Lett. 2011, 52, 6729-6731
13. Ashraf, C.; Jackson, W. Aust. J. Chem. 1978, 31, 1845-1849
14. Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974-12980
15. Lodewyk, M. W.; Siebert, M. R.; Tantillo, D. J. Chem. Rev. 2011, 112, 1839-1862
16. Bagno, A.; Rastrelli, F.; Saielli, G. Chem. Eur. J. 2006, 12, 5514-5525
17. Pu, J.-X.; Huang, S.-X.; Ren, J.; Xiao, W.-L.; Li, L.-M.; Li, R.-T.; Li, L.-B.; Liao, T.-G.; Lou, L.-G.; Zhu, H.-J.; Sun, H.-D. J. Nat. Prod. 2007, 70, 1706-1711
18. Halgren, T. A. J. Comput. Chem. 1999, 20, 720-729
19. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
20. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
21. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211
22. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
23. Tannor, D. J.; Marten, B.; Murphy, R.; Friesner, R. A.; Sitkoff, D.; Nicholls, A.; Honig, B.; Ringnalda, M.; Goddard, W. A. J. Am. Chem. Soc. 1994, 116, 11875-11882
24. Marten, B.; Kim, K.; Cortis, C.; Friesner, R. A.; Murphy, R. B.; Ringnalda, M. N.; Sitkoff, D.; Honig, B. J. Phys. Chem. 1996, 100, 11775-11788
25. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664-675
26. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512-7515
27. Smith, S. G.; Goodman, J. M. J. Am. Chem. Soc. 2010, 132, 12946-12959
28. Lodewyk, M. W.; Tantillo, D. J. J. Nat. Prod. 2011, 74, 1339-1343
29. Wyche, T. P.; Hou, Y.; Braun, D.; Cohen, H. C.; Xiong, M. P.; Bugni, T. S. J. Org. Chem. 2011, 76, 6542-6547
30. Schwartz, B. D.; Jones, M. T.; Banwell, M. G.; Cade, I. A. Org. Lett. 2010, 12, 5210-5213
31. Dictionary of Natural Products on DVD, version 21.2; Taylor & Francis/CRC Press: London, UK, 2012.
32. Van Soest, R.; Carballo, J. L.; Hooper, J. ZooKeys 2012, 239, 1-70
33. MacroModel, version 9.9, Suite 2012; Schrödinger, LLC: New York, NY, 2012.
34. Jaguar, version 7.9, Suite 2012; Schrödinger, LLC: New York, NY, 2012.
35. Bally, T.; Rablen, P. R. J. Org. Chem. 2011, 76, 4818-4830
36. Jain, R.; Bally, T.; Rablen, P. R. J. Org. Chem. 2009, 74, 4017-4023