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3-Alkylpyridinium
3- Alkylpyridinium (3-APs) are natural compounds that are found in marine sponges belonging to the order Haplosclerida. These compounds are interesting and serves as novel potential pharmaceuticals in treating several diseases because of its profound biological activities.〔Turk T., Sepcˇic´ K.,Mancini I.,Guella G. (2008) (3-Alkylpyridinium and 3-Alkylpyridine compounds from marine sponges, their synthesis, biological activities and potential use ) In Rahman A. ''Studies in Natural Products Chemistry''. First edition, pp 355-398〕 3-APs polymers are potent anticholinesterase agents, in addition, they show hemolytic and cytotoxic activities.〔Sepcˇic´ K.,Guella G.,Mancini I., Pietra F., Serra M.D., Menestrina G., Tubbs K., Macˇek P., Truk T.(1997) (Characterization of Anticholinesterase-Active 3-Alkylpyridinium Polymers from the Marine Sponge Reniera sarai in Aqueous Solutions ) ''Journal of Natural Products'', 60, 991-996〕 More than 70 structurally different 3-APs have been isolated from marine sponges. However, not all such sponges contain 3-AP compounds. Variation in content of 3-APs has been detected even within a single sponge species collected from different geographical area.〔 Although 3-APs look structurally quite simple, the structure elucidation by NMR spectroscopy is complicated by the fact that most of the methylene groups in the alkyl chains show the same chemical shift. Therefore, the 3-APs are an ideal test case for a combined approach of NMR spectroscopy and mass spectrometry.〔Timm C., Mordhorst T., Köck M. (2010) (Synthesis of 3-Alkyl Pyridinium Alkaloids from the Arctic Sponge Haliclona viscosa ) ''Marine Drugs''. 2010; 8(3): 483–497〕
==History==
The chemical studies on sponges of the order Haplosclerida started in 1978 with the work of Schmitz et al. on different species of the genus Haliclona (Figure 1) with the aim to identify the compounds responsible for the high ichthyotoxicity of the aqueous extract of this sponge. They were able to isolate the toxic halitoxin, identified as a complex mixture of 3-alkylpyridinium polymeric salts.〔Laville R., Amade P.,Thomas O.P. (2009) (3-Alkylpyridinium salts from Haplosclerida marine sponges: Isolation, structure elucidations, and biosynthetic considerations ) ''Pure Appl. Chem''., Vol. 81, No. 6, pp. 1033–1040〕
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