Structure and absolute stereochemistry of syphonoside, a unique macrocyclic glycoterpenoid from marine organisms

Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5625-5630

  Gavagnin, Margherita ^a   Carbone, Marianna ^a   Amodeo, Pietro ^a   Mollo, Ernesto ^a   Vitale, Rosa Maria ^b   Roussis, Vassilios ^c   Cimino, Guido ^a  

^a CNR Consiglio Nazionale delle Ricerche   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONAL ANALYSIS; HALOPHILA STIPULACEA; SYPHONOSIDE;

CELLS; CONFORMATIONS; MARINE BIOLOGY; STEREOCHEMISTRY;

METABOLITES;

GLYCOTERPENOID; MACROCYCLIC COMPOUND; SYPHONOSIDE; TERPENOID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; DEGRADATION KINETICS; HALOPHILA STIPULACEA; MARINE ENVIRONMENT; MOLLUSC; NONHUMAN; POPULATION MIGRATION; STEREOCHEMISTRY; SYPHONOTA GEOGRAPHICA;

ANIMALS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MARINE BIOLOGY; MICE; MOLECULAR STRUCTURE; POACEAE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; TERPENES;

EID: 34547109840     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0704917     Document Type: Article

References (26)

1. Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2007, 24, 31-86; and earlier articles in this series.
2. Paul, V. J. Ecological Roles of Marine Natural Products; Comstock Publishing Associates: Ithaca, NY, 1992.
3. Cimino, G., Gavagnin, M., Eds. Molluscs, From Chemo-ecological Study to Biotechnological Application; Springer: Berlin, 2006; Vol. 43.
4. Karuso, P. In Bioorganic Marine Chemistry; Scheuer P. J., Ed.; Springer-Verlag: Berlin, 1987; Vol. 1, pp 31-60.
5. Cimino, G.; Fontana, A.; Gavagnin, M. Curr. Org. Chem. 1999, 3, 327-372.
6. Cimino, G.; Ciavatta, M. L.; Fontana, A.; Gavagnin, M. In Bioactive Natural Products: Isolation, Structure Elucidation and Biology Properties; Tringali, C., Ed.; Taylor and Francis: London, UK, 2001; pp 577-637.
7. Cimino, G.; Fontana, A.; Cutignano, A.; Gavagnin, M. Phytochem. Rev. 2004, 3, 285-307.
8. Carefoot, T. H. Oceanogr. Mar. Biol. Annu. Rev. 1987, 25, 167-284.
9. Gavagnin, M.; Carbone, M.; Nappo, M.; Mollo, E.; Roussis, V.; Cimino, G. Tetrahedron 2005, 61, 617-621.
10. Eales, N. B. Bull. Br. Mus. (Nat. Hist.) Zool. 1960, 5, 267-404.
11. Lipkin, Y. Isr. J. Bot. 1975, 24, 198-200.
12. Boudouresque, C. F.; Verlaque, M. Mar. Pollut. Bull. 2002, 44, 32-38.
13. Nogueira, R. T.; Shepherd, G. J.; Laverde, A., Jr.; Marzaioli, A. J.; Imamura, P. M. Phytochemistry 2001, 58, 1153-1157.
14. 1H NMR data and CD profiles of benzoyl glucose derivatives.
15. Gippert, G. P.; Yip, P. F.; Wright, P. E.; Case, D. A. Biochem. Pharmacol. 1990, 40, 15-22.
16. Iliopoulou, D.; Mihopoulos, N.; Vagias, C.; Papazafiri, P.; Roussis, V. J. Org. Chem. 2003, 68, 7667-7674.
17. Case, D. A.; Darden, T. A.; Cheatham, T. E., III; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Merz, K. M.; Wang, B.; Pearlman, D. A.; Crowley, M.; Brozell, S.; Tsui, V.; Gohlke, H.; Mongan, J.; Hornak, V.; Cui, G.; Beroza, P.; Schafmeister, C.; Caldwell, J. W.; Ross, W. S.; Kollman, P. A. AMBER 8, University of California, San Francisco, 2004.
18. Wang, J.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. J. Comput. Chem. 2004, 25, 1157-1174.
19. Jakalian, A.; Bush, B. L.; Jack, D. B.; Bayly, C. I. J. Comput. Chem. 2000, 21, 132-146.
20. Rowley, C.; Hassinen, T. Chemical, 2001-2002; licensed un GNU GPL, Copyright 2006 Tommi Hassinen, Kuopio, Finland (http://www.bioinformatics.org/ ghemical/ghemical/index.html).
21. Tsui, V.; Case, D. A. Biopolymers 2001, 56, 275-291.
22. Weiser, J.; Shenkin, P. S.; Still, W. C. J. Comput. Chem. 1999, 20, 217-230.
23. Koradi, R.; Billeter, M.; Wüthrich, K. J. Mol. Graph. 1996, 14, 51-55.
24. Mossmann, T. J. Immunol. Methods 1983, 65, 55-63.
25. Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Cancer Res. 1988, 48, 589-601.
26. Experimental details are reported in Supporting Information.