Synthesis of 3-alkyl pyridinium alkaloids from the arctic sponge Haliclona viscosa.
3-Alkyl pyridinium alkaloids (3-APAs) are common secondary metabolites in marine sponges of the order Haplosclerida. In recent years, our laboratory has isolated and synthesized several new members of this family such as haliclamines C-F, viscosamine, viscosaline and a cyclic monomer. All of them were isolated from the Arctic sponge Haliclona viscosa collected in Spitsbergen, Norway. In this article we report the syntheses of these secondary metabolites from Haliclona viscosa and related compounds and give a short overview of the bioactivity.
Timm
Christoph
C
Alfred-Wegener-Institut für Polar- und Meeresforschung in der Helmholtz-Gemeinschaft, Am Handelshafen 12, D-27570 Bremerhaven, Germany.
Mordhorst
Thorsten
T
Köck
Matthias
M
D000818:Animals; D000890:Anti-Infective Agents / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001688:Biological Products; D047129:Haliclona / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000890:Anti-Infective Agents; D001688:Biological Products; D011726:Pyridinium Compounds
J Org Chem. 2002 Sep 6;67(18):6474-8
12201769
Bioorg Med Chem Lett. 2004 May 17;14(10):2617-20
15109664
Org Biomol Chem. 2008 Nov 7;6(21):4036-40
18931812
Org Lett. 2003 Oct 2;5(20):3567-9
14507174
Org Biomol Chem. 2004 May 7;2(9):1368-75
15105928
J Med Chem. 2007 May 17;50(10):2497-505
17447750
J Nat Prod. 2004 Oct;67(10):1685-9
15497940
J Org Chem. 2000 Sep 8;65(18):5837-8
10970332
J Nat Prod. 2006 Jan;69(1):135-7
16441085
Org Biomol Chem. 2004 Jul 7;2(13):1827-30
15227533