Biogenesis of 3-alkylpyridine alkaloids in the marine mollusc Haminoea Orbignyana

Angewandte Chemie - International Edition

Volumn 42, Issue 23, 2003, Pages 2633-2636

  Cutignano, Adele ^a   Tramice, Annabella ^a   De Caro, Salvatore ^a   Villani, Guido ^a   Cimino, Guido ^a   Fontana, Angelo ^a  

^a CNR   (Italy)

Author keywords

Alkaloids; Biosynthesis; Ecology; Natural products

Indexed keywords

BIOSYNTHESIS; MARINE APPLICATIONS;

BIOGENESIS;

ORGANIC COMPOUNDS;

ALKALOID DERIVATIVE; ALKYL GROUP; HETEROCYCLIC COMPOUND; NATURAL PRODUCT; NITROGEN DERIVATIVE; PYRIDINE DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; EXTRACTION; FEEDING; HAMINOEA ORBIGNYANA; ISOTOPE LABELING; MARINE ENVIRONMENT; MOLLUSC; NONHUMAN; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

ALKALOIDS; ANIMALS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MOLECULAR STRUCTURE; MOLLUSCA; PIPERIDINES;

EID: 0038451473     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250642     Document Type: Article

References (25)

1. a) D. J. Faulkner, Nat. Prod. Rep. 2002, 19, 1-48, and references therein;
2. b) A. Fontana, G. Cimino, Recent Res. Dev. Org. Chem. 2001, 5, 89-105;
3. c) B. S. Moore, Nat. Prod. Rep. 1999, 16, 653-674;
4. d) W. H. Gerwick, M. A. Roberts, A. Vulpanovici, D. L. Ballantine, Adv. Exp. Med. Biol. 1999, 447, 211-218;
5. e) W. H. Gerwick, Biochim. Biophys. Acta 1994, 1211, 243-255;
6. f) M. J. Garson, Nat. Prod. Rep. 1989, 6, 143-170.
7. a) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794;
8. b) I. Kitigawa, M. Kobayashi, Gazz. Chim. Ital. 1993, 123, 321-325;
9. c) J. E. Baldwin, C. R. Whitehead, Tetrahedron Lett. 1992, 33, 2059-2062;
10. d) G. Cimino, G. Scognamiglio, A. Spinella, E. Trivellone, J. Nat. Prod. 1990, 53, 1519-1525.
11. R. J. Andersen, R. W M. van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelletier), Pergamon, London, 1996, pp. 301-355, and references therein.
12. G. Cimino, M. L. Ciavatta, A. Fontana, M. Gavagnin in Bioactive Compounds from Natural Sources, (Ed.: C. Tringali), Taylor and Francis, 2001, pp. 577-637.
13. a) G. Cimino, A. Passeggio, G. Sodano, A. Spinella, G. Villani, Experientia 1991, 47, 61-63;
14. b) A. Spinella, L. A. Alvarez, A. Passeggio, G. Cimino, Tetrahedron 1993, 49, 1307-1314.
15. J. Mann in Natural products: their chemistry and biological significance. Alkaloids, (Eds.: J. Mann, R. S. Davidson, J. B. Hobbs, D.V. Banthorpe, J.B. Harborne), Longman, London, 1994, pp. 389-446.
16. W. Fenical, H. L. Sleeper, V. J. Paul, M. O. Stallard, H. H. Sun, Pure Appl. Chem. 1979, 51, 1865-1874.
17. J. Staunton, B. Wilkinson, Top. Curr. Chem. 1998, 195, 49-92.
18. a) G. Cimino, S. De Stefano, G. Scognamiglio, G. Sodano, E. Trivellone, Bull. Soc. Chim. Belg. 1986, 95, 783-800;
19. b) G. Cimino, A Spinella, E. Trivellone, Tetrahedron Lett. 1989, 30, 133-136;
20. c) G. Cimino, C. A. Mattia, L. Mazzarella, R. Puliti, G. Scognamiglio, A. Spinella, Tetrahedron 1989, 45, 3863-3872.
21. a) R. Sakai, T. Higa, C. W. Jefford, G. Berardinelli, J. Am. Chem. Soc. 1986, 108, 6404-6405;
22. b) R. Sakai, S. Kohmoto, T. Higa, C. W. Jefford, G. Berardinelli, Tetrahedron Lett. 1987, 28, 5493-5946.
23. a) J. E. Baldwin, R. C. Whitehead, Tetrahedron Lett. 1992, 33, 2059-2062;
24. b) J. E. Baldwin, T. D. W. Claridge, A. J. Culshaw, F. A. Heupel, V. Lee, D. R. Spring, R. C. Whitehead, R. J. Boughtflower, I. M. Mutton, R. J. Upton, Angew. Chem. 1998, 110, 2806-2808; Angew. Chem. Int. Ed. 1998, 37, 2661-2663.
25. b) J. E. Baldwin, T. D. W. Claridge, A. J. Culshaw, F. A. Heupel, V. Lee, D. R. Spring, R. C. Whitehead, R. J. Boughtflower, I. M. Mutton, R. J. Upton, Angew. Chem. 1998, 110, 2806-2808; Angew. Chem. Int. Ed. 1998, 37, 2661-2663.