Monanchocidins B-E: Polycyclic guanidine alkaloids with potent antileukemic activities from the sponge Monanchora pulchra

Journal of Natural Products

Volumn 74, Issue 9, 2011, Pages 1952-1958

  Makarieva, Tatyana N ^a   Tabakmaher, Ksenya M ^a   Guzii, Alla G ^a   Denisenko, Vladimir A ^a   Dmitrenok, Pavel S ^a   Shubina, Larisa K ^a   Kuzmich, Alexandra S ^a   Lee, Hyi Seung ^b   Stonik, Valentin A ^a  

^a PACIFIC INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^b Korea Research Institute of Ships and Ocean Engineering   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; ANTILEUKEMIC AGENT; MONANCHOCIDIN; MONANCHOCIDIN A; MONANCHOCIDIN B; MONANCHOCIDIN C; MONANCHOCIDIN D; MONANCHOCIDIN E; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN HL 60; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG TRANSFORMATION; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL; MARINE SPECIES; MONANCHORA PULCHRA; NONHUMAN; SPECTROSCOPY; SPONGE (PORIFERA);

ALKALOIDS; ANIMALS; ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; GUANIDINES; HL-60 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA;

MONANCHORA PULCHRA;

EID: 80053177148     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200452m     Document Type: Article

References (30)

1. Kashman, Y.; Hirsh, S.; McConnell, O. J.; Ohtani, I.; Kusumi, T.; Kakisawa, H. J. Am. Chem. Soc. 1989, 111, 8925-8926
2. Heys, L.; Moore, C. G.; Murphy, P. J. Chem. Soc. Rev. 2000, 29, 57-67
3. Berlinck, R. G. S. Nat. Prod. Rep 2002, 19, 617-649
4. Berlinck, R. G. S.; Kossuga, M. H. Nat. Prod. Rep 2005, 22, 516-550
5. Berlinck, R. G. S.; Burtoloso, A. C. B.; Trindade-Silva, A. E.; Romminger, S.; Morais, R. P.; Bandeira, K.; Mizuno, C. M. Nat. Prod. Rep 2010, 27, 1871-1907
6. Jares-Erijman, E. A.; Sakai, R.; Rinehart, K. L. J. Org. Chem. 1991, 56, 5712-5715
7. Ohtani, I.; Kusumi, T.; Kakisawa, H.; Kashman, Y.; Hirsh, S. J. Am. Chem. Soc. 1992, 114, 8472-8479
8. Rinehart, K. L.; Shi, J.-G.; Sun, F. U.S. Patent 6,028,077, 2000.
9. Jares-Erijman, E. A.; Ingrum, A. L.; Carney, J. R.; Rinehart, K. L.; Sakai, R. J. Org. Chem. 1993, 58, 4805-4808
10. Bensemhoun, J.; Bombarda, I.; Aknin, J.; Vacelet, J.; Gaydou, E. M. J. Nat. Prod. 2007, 70, 2033-2035
11. Palagiano, E.; De Marino, S.; Minale, L.; Riccio, R.; Zollo, F.; Carre, J. B.; Debitus, C.; Lucarain, L.; Provost, J. Tetrahedron 1995, 51, 3675-3682
12. Gallimore, W. A.; Kelly, M.; Scheuer, P. J. J. Nat. Prod. 2005, 68, 1420-1423
13. Chang, L.; Whittaker, N. F.; Bewley, C. A. J. Nat. Prod. 2003, 66, 1490-1494
14. Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Bruno, I.; Riccio, R.; Ferri, S.; Spampinato, S.; Speroni, E. J. Nat. Prod. 1993, 56, 1007-1015
15. Tavares, R.; Daloze, D.; Braekman, J. C.; Hajdu, E.; Muricy, G.; Van Soest, R. W. M. Biochem. Syst. Ecol. 1994, 22, 645-646
16. Braekman, J. C.; Daloze, D.; Tavares, R.; Hajdu, E.; Van Soest, R. W. M. J. Nat. Prod. 2000, 63, 193-196
17. Laville, R.; Thomas, O. P.; Berrue, F.; Marquez, D.; Vacelet, J.; Amade, P. J. Nat. Prod. 2009, 72, 1589-1594
18. Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; De Brosse, C.; Mai; Truneh, A.; Faulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westley, J. W.; Potts, B. C. M. J. Org. Chem. 1995, 60, 1182-1188
19. Patil, A. D.; Freyer, A. J.; Taylor, P. B.; Carte, B.; Zuber, G.; Johnson, R. K.; Faulkner, D. J. J. Org. Chem. 1997, 62, 1814-1819
20. Hua, H.-M.; Peng, J.; Dunbar, D. C.; Schinazi, R. F.; De Castro Andrews, A. G.; Cuevas, C.; Garcia-Fernandes, L. F.; Kelly, M.; Hamann, M. T. Tetrahedron 2007, 63, 11179-11188
21. Berlinck, R. G. S.; Braekman, J. C.; Daloze, D; Bruno, I.; Riccio, R.; Rogea, U. D.; Amade, P. J. Nat. Prod. 1992, 55, 528-532
22. Jares-Erijman, E. A.; Ingrum, A. L.; Sun, F. R.; Rinehart, K. L. J. Nat. Prod. 1993, 56, 2186-2188
23. Sun, H. H.; Sakemi, S.; Burres, N.; McCarthy, P. J. Org. Chem. 1990, 55, 4964-4966
24. Sorek, H.; Rudi, A.; Gueta, S.; Reyes, F.; Martin, M. J.; Aknin, M.; Gaydou, E.; Vacelet, J.; Kashman, Y. Tetrahedron 2006, 62, 8838-8843
25. Hua, H.-M.; Peng, J.; Fronczek, F. R.; Kelly, M.; Hamann, M. T. Bioorg. Med. Chem. 2004, 12, 6461-6464
26. Guzii, A. G.; Makarieva, T. N.; Denisenko, V. A.; Dmitrenok, P. S.; Kuzmich, A. S.; Dyshlovoy, S. A.; Krasokhin, V. B.; Stonik, V. A. Org. Lett. 2010, 12, 4292-4295
27. Makarieva, T. N.; Krasokhin, V. B.; Guzii, A. G.; Stonik, V. A. Chem. Nat. Compd. 2010, 46, 152-153
28. The formation of only one (compound 6) of four possible products was indicated by HPLC and NMR data after the reduction. That is why we suggest a direct reductive pathway for transformation of the "vessel" part, but not via hydrolysis followed by reduction of the intermediate imine. See for direct hydrogenolysis of hemiaminal groups: Berdini, V.; Cesta, C.; Curti, R.; D'Anniballe, G.; Di Bello, N.; Nano, G.; Nicolini, L.; Topai, A.; Allegretti, M. Tetrahedron 2002, 58, 5669-5674
29. Baltrop, J. A.; Owen, T. C.; Cory, A. H.; Cory, J. G. Bioorg. Med. Chem. Lett. 1991, 1, 611-614
30. Fedorov, S. N.; Shubina, L. K.; Kicha, A. A.; Ivanchina, N. V.; Kwak, J. Y.; Jin, J. O.; Bode, A. M.; Dong, Z.; Stonik, V. A. Nat. Prod. Commun. 2008, 3, 1575-1580