Njaoaminiums A, B, and C: Cyclic 3-alkylpyridinium salts from the marine sponge Reniera sp.

Molecules

Volumn 14, Issue 11, 2009, Pages 4716-4724

  Laville, Remi ^a   Genta Jouve, Grégory ^a   Urda, Carlos ^b   Fernández, Rogelio ^b   Thomas, Olivier P ^a   Reyes, Fernando ^b   Amade, Philippe ^a  

^a UNIVERSITÉ DE NICE SOPHIA ANTIPOLIS   (France)

^b PHARMAMAR S A   (Spain)

Author keywords

Absolute configuration; Alkylpyridinium; Circular dichroism; Marine natural products; Marine sponge; Reniera

Indexed keywords

EID: 73349116533     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14114716     Document Type: Article

References (16)

1. For reviews on 3-alkylpyridinium salts, see: Sepcik, K. Bioactive alkylpyridinium compounds from marine sponges. J. Toxicol. 2000, 19, 139-160.
2. Andersen, R. J.; van Soest, R. W.; Kong, F. Alkaloids, Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Elsevier Science: Oxford, UK, 1996; Vol. 10, pp. 301-355.
3. Sepcik, K.; Turk, T. 3-alkylpyridinium compounds as potential non-toxic antifouling agents. Prog. Mol. Subcell. Biol. 2006, 42, 105-124.
4. Fusetani, N.; Asai, N.; Matsunaga, S. Cyclostellettamines, A.-F, pyridine alkaloids which inhibit binding of methyl quinuclidinyl benzilate (QNB) to muscarinic acetylcholine receptors, from the marine sponge, Stelletta maxima. Tetrahedron Lett. 1994, 35, 3967-3970.
5. De Oliveira, J. H. H. L.; Grube, A.; Köck, M.; Berlinck, R. G. S.; Macedo, M. L.; Ferreira, A. G.; Hajdu, E. Ingenamine G and cyclostellettamines G-I, K, and L from the new Brazilian species of marine sponge Pachychalina sp. J. Nat. Prod. 2004, 67, 1685-1689.
6. Volk, C. A.; Köck, M. Viscosamine: The first naturally occurring trimeric 3-alkyl pyridinium alkaloid. Org. Lett. 2003, 5, 3567-3569.
7. Teruya, T.; Kobayashi, K.; Suenaga, K.; Kigoshi, H. Cyclohaliclonamines A-E: dimeric, trimeric, tetrameric, pentameric, and hexameric 3-alkyl pyridinium alkaloids from a marine sponge haliclona sp. J. Nat. Prod. 2006, 69, 135-137.
8. Kong, F.; Andersen, R. J.; Allen, T. M. Ingamines A and B, new cytotoxic alkaloids from the marine sponge Xestospongia ingens. Tetrahedron 1994, 50, 6137-6144.
9. Kobayashi, J.; Tsuda, M.; Kawasaki, N.; Matsumoto, K.; Adachi, T. Keramaphidin B, a novel pentacyclic alkaloid from a marine sponge Amphimedon sp.: A plausible biogenetic precursor of manzamine alkaloids. Tetrahedron Lett. 1994, 35, 4383-4386.
10. Rodriguez, J.; Peters, B. M.; Kurtz, L.; Schatzman, R. C.; McCarley, D.; Lou, L.; Crews, P. An alkaloid protein kinase C inhibitor, xestocyclamine A, from the marine sponge Xestospongia sp. J. Am. Chem. Soc. 1993, 115, 10436-10437.
11. Jaspars, M.; Pasupathy, V.; Crews, P. A tetracyclic diamine alkaloid, halicyclamine A, from the marine sponge Haliclona sp. J. Org. Chem. 1994, 59, 3253-3255.
12. Baldwin, J. E.; Claridge, T. D. W.; Culshaw, A. J.; Heupel, F. A.; Lee, V.; Spring, D. R.; Whitehead, R. C.; Boughtflower, R. J.; Mutton, I. M.; Upton, R. J. Investigations into the manzamine alkaloid biosynthetic hypothesis. Angew. Chem. Int. Ed. 1998, 37, 2661-2663.
13. Jakubowicz, K.; Ben Abdeljelil, K.; Herdemann, M.; Martin, M. T.; Gateau-Otesker, A.; Al Mourabit, A.; Marazano, C.; Das, B. C. Reactions of aminopentadienal derivatives with 5, 6-dihydropyridinium salts as an approach to manzamine alkaloids based upon biogenetic considerations. J. Org. Chem. 1999, 64, 7381-7387.
14. Reyes, F.; Fernández, R.; Urda, C.; Francesch, A.; Bueno, S.; de Eguilior, C.; Cuevas, C. Njaoamines A-F, new cytotoxic polycyclic alkaloids from the haplosclerid sponge Reniera sp. Tetrahedron 2007, 63, 2432-2438.
15. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, A. C.; Nanayakkara, Y.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.01; Gaussian, Inc.: Wallingford, CT, USA, 2004.
16. Shenan, P.; Storeng, R.; Scudiero, D.; Monks, A.; Mc Mahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 1990, 82, 1107-1112. © 2009