Synthesis of 3-alkyl pyridinium alkaloids from the arctic sponge Haliclona viscosa

Marine Drugs

Volumn 8, Issue 3, 2010, Pages 483-497

  Timm, Christoph ^a   Mordhorst, Thorsten ^a   Köck, Matthias ^a  

^a ALFRED WEGENER INSTITUTE FOR POLAR AND MARINE RESEARCH   (Germany)

Author keywords

3 alkyl pyridinium alkaloids; Haliclona viscosa; Marine natural products; Synthesis

Indexed keywords

3 PYRIDINIUM ALKALOID; ALKALOID DERIVATIVE; CYCLOSTELLETTAMINE; HALICLAMINE C; HALICLAMINE D; HALICLAMINE E; HALICLAMINE F; ISOCYCLOSTELLETTAMINE; UNCLASSIFIED DRUG; VISCOSALINE METHYL ESTER; VISCOSAMINE; ANTIINFECTIVE AGENT; BIOLOGICAL PRODUCT; PYRIDINIUM DERIVATIVE;

ANTIMICROBIAL ACTIVITY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; MARINE SPECIES; MASS SPECTROMETRY; NONHUMAN; NORWAY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REVIEW; SPONGE (PORIFERA); STAPHYLOCOCCUS AUREUS; ANIMAL; BACTERIA; CHEMISTRY; DRUG EFFECTS; HALICLONA; SYNTHESIS;

HALICLONA VISCOSA; HAPLOSCLERIDA;

ANIMALS; ANTI-INFECTIVE AGENTS; BACTERIA; BIOLOGICAL PRODUCTS; HALICLONA; PYRIDINIUM COMPOUNDS;

EID: 77952529082     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md8030483     Document Type: Review

References (39)

1. Kelman, D.; Kashman, Y.; Rosenberg, E.; Ilan, M.; Ifrach, I.; Loya, Y. Antimicrobial activity of the reef sponge Amphimedon viridis from the Red Sea: evidence for selective toxicity. Aquat. Microb. Ecol. 2001, 24, 9-16.
2. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hirota, H. Haliclamines A and B, cytotoxic macrocyclic alkaloids from a sponge of the genus Haliclona. Tetrahedron Lett. 1989, 30, 6891-6894.
3. Lippert, H.; Iken, K.; Volk, C.; Köck, M.; Rachor, E. Chemical defence against predators in a sub-Arctic fjord. J. Exp. Mar. Biol. Ecol. 2004, 310, 131-146.
4. Quiñoà, E.; Crews, P. Niphatynes, methoxylamine pyridines from the marine sponge, Niphates sp. Tetrahedron Lett. 1987, 28, 2467-2468.
5. Kobayashi, J.; Murayama, T.; Kosuge, S.; Kanda, F.; Ishibashi, M.; Kobayashi, H.; Ohizumi, Y.; Ohta, T.; Nozoe, S.; Sasaki, T. Niphatesines A-D, new antineoplastic pyridine alkaloids from the Okinawan marine sponge Niphates sp. J. Chem. Soc., Perk. Trans. 1 1990, 3301-3303.
6. Kobayashi, J.; Zeng, C.-m.; Ishibashi, M.; Shigemori, H.; Sasaki, T.; Mikami, Y. Niphatesines E-H, new pyridine alkaloids from the Okinawan marine sponge Niphates sp. J. Chem. Soc., Perk. Trans. 1 1992, 1291-1294.
7. Carroll, A.R.; Scheuer, P.J. Four beta-alkylpyridines from a sponge. Tetrahedron 1990, 46, 6637-6644.
8. Laville, R.; Thomas, O.P.; Berrue, F.; Reyes, F.; Amade, P. Pachychalines A-C: Novel 3-alkylpyridinium salts from the marine sponge Pachychalina sp. Eur. J. Org. Chem. 2008, 121-125.
9. Talpir, R.; Rudi, A.; Ilan, M.; Kashman, Y. Niphatoxin A and B; two new ichthyo- and cytotoxic tripyridine alkaloids from a marine sponge. Tetrahedron Lett. 1992, 33, 3033-3034.
10. Volk, C.A.; Köck, M. Viscosaline: new 3-alkyl pyridinium alkaloid from Arctic sponge Haliclona viscosa. Org. Biomol. Chem. 2004, 2, 1827-1830.
11. Schmitz, F.J.; Hollenbeak, K.H.; Campbell, D.C. Marine natural products: halitoxin, toxic complex of several marine sponges of the genus Haliclona. J. Org. Chem. 1978, 43, 3916-3922.
12. Mancini, I.; Sicurelli, A.; Guella, G.; Turk, T.; Maček, P.; Sepčić, K. Synthesis and bioactivity of linear oligomers related to polymeric alkylpyridinium metabolites from the Mediterranean sponge Reniera sarai. Org. Biomol. Chem. 2004, 2, 1368-1375.
13. Anan, H.; Seki, N.; Noshiro, O.; Honda, K.; Yasumuro, K.; Ozasa, T.; Fusetani, N. Total synthesis of cyclostellettamines C, a bispyridinium macrocycle alkaloid having muscarinic acetylcholine receptor antagonistic activity. Tetrahedron 1996, 52, 10849-10860. (Pubitemid 26253343)
14. Kaiser, A.; Billot, X.; Gateau-Olesker, A.; Marazano, C.; Das, B.C. Selective entry to the dimeric or oligomeric pyridinium sponge macrocycles via aminopentadienal derivatives. Possible biogenetic relevance with manzamine alkaloids. J. Am. Chem. Soc. 1998, 120, 8026-8034.
15. Timm, C.; Volk, C.; Sasse, F.; Köck, M. The first cyclic monomeric 3-alkylpyridinium alkaloid from natural sources: identification, synthesis, and biological activity. Org. Biomol. Chem. 2008, 6, 4036-4040.
16. Fusetani, N.; Asai, N.; Matsunaga, S.; Honda, K.; Yasumuro, K. 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.
17. Oku, N.; Nagai, K.; Shindoh, N.; Terada, Y.; van Soest, R.W.M.; Matsunaga, S.; Fusetani, N. Three new cyclostellettamines, which inhibit histone deacetylase, from a marine sponge of the genus Xestospongia. Bioorg. Med. Chem. Lett. 2004, 14, 2617-2620.
18. 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.
19. Morimoto, Y.; Yokoe, C. Total synthesis of haliclamine A, a macrocyclic marine alkaloid related to the key biogenetic intermediate of manzamines. Tetrahedron Lett. 1997, 52, 8981-8984. (Pubitemid 27526197)
20. Morimoto, Y.; Yokoe, C.; Kurihara, H.; Kinoshita, T. Total syntheses of macrocyclic marine alkaloids, haliclamines A and B: a convenient and expeditious assembly of 3-substituted pyridine derivatives with different alkyl chains to the bispyridinium macrocycle. Tetrahedron 1998, 54, 12197-12214. (Pubitemid 28557054)
21. Volk, C.A.; Lippert, H.; Lichte, E.; Köck, M. Two new haliclamines from the Arctic sponge Haliclona viscosa. Eur. J. Org. Chem. 2004, 3154-3158.
22. Schmidt, G.; Timm, C.; Köck, M. New haliclamines E and F from the Arctic sponge Haliclona viscosa. Org. Biomol. Chem. 2009, 7, 3061-3064.
23. 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.
24. Volk, C.A.; Köck, M. Viscosamine: the first naturally occurring trimeric 3-alkyl pyridinium alkaloid. Org. Lett. 2003, 5, 3567-3569.
25. Davies-Coleman, M.T.; Faulkner, D.J.; Dubowchik, G.M.; Roth, G.P.; Polson, C.; Fairchild, C. A new EGF-active polymeric pyridinium alkaloid from the sponge Callyspongia fibrosa. J. Org. Chem. 1993, 58, 5925-5930.
26. Lippert, H.; Iken, K. Palatability and nutritional quality of marine invertebrates in a sub-Arctic fjord. J. Mar. Biol. Ass. UK 2003, 83, 1215-1219.
27. Lippert, H. Chemical ecology and palatability of marine invertebrates in the sub-Arctic Kongsfjord (Spitsbergen). Ber. Polarforsch. Meeresforsch. 2004, 465, 1-109.
28. Lippert, H.; Brinkmeyer, R.; Mülhaupt, T.; Iken, K. Antimicrobial activity in sub-Arctic marine invertebrates. Polar Biol. 2003, 26, 591-600. (Pubitemid 37118183)
29. Grube, A.; Timm, C.; Köck, M. Synthesis and mass spectrometric analysis of cyclostellettamines H, I, K and L. Eur. J. Org. Chem. 2006, 1285-1295.
30. Chong, J.M.; Heuft, M.A.; Rabbat, P. Solvent effects on the monobromination of α,ω-diols: a convenient preparation of ω-bromoalkanols. J. Org. Chem. 2000, 65, 5837-5838.
31. Brown, H.C.; Choi, Y.M.; Narasimhan, S. Selective reductions. 29. A simple technique to achieve an enhanced rate of reduction of representative organic compounds by borane-dimethyl sulfide. J. Org. Chem. 1982, 47, 3153-3163.
32. Baldwin, J.E.; Spring, D.R.; Atkinson, C.E.; Lee, V. Efficient synthesis of the sponge alkaloids cyclostellettamines A-F. Tetrahedron 1998, 54, 13655-13680. (Pubitemid 28475090)
33. Gil, L.; Gateau-Olesker, A.; Wong, Y.-S.; Chernatova, L.; Marazano, C.; Das, B.C. Synthesis of macrocyclic or linear pyridinium oligomers from 3-substituted pyridines. Model synthetic studies toward macrocyclic marine alkaloids. Tetrahedron Lett. 1995, 36, 2059-2062.
34. Michelliza, S.; Al-Mourabit, A.; Gateau-Olesker, A.; Marazano, C. Synthesis of the cytotoxic sponge metabolite haliclamine A. J. Org. Chem. 2002, 67, 6474-6478.
35. Pérez-Balado, C.; Nebbioso, A.; Rodríguez-Graña, P.; Minichiello, A.; Miceli, M.; Altucci, L.; de Lera, A.R. Bispyridinium dienes: histone deacetylase inhibitors with selective activities. J. Med. Chem. 2007, 50, 2497-2505.
36. Wanner, M.J.; Koomen, G.-J. Synthesis of the cyclostellettamines A-F and related bis(3-alkyl pyridinium) macrocycles. Eur. J. Org. Chem. 1998, 889-895.
37. Mori, M.; Chiba, K.; Okita, M.; Kayo, I.; Ban, Y. New synthesis of β-lactams. Tetrahedron 1985, 41, 375-385.
38. Cachoux, F.; Schaal, F.; Teichert, A.; Wagner, T.; Altmann, K.-H. Synthesis of 4-aza analogs of epothilone D. Synlett 2004, 2709-2712.
39. Shorey, B.J.; Lee, V.; Baldwin, J.E. Synthesis of the Arctic sponge alkaloid viscosaline and the marine sponge alkaloid theonelladin C. Tetrahedron 2007, 63, 5587-5592.