Axinella alkaloids

An Australian sponge Axinella sp. has afforded the novel axinellamines A-D (1310-1313), which exhibit activity against Helicobacter pylori (1301). The similar massadine (1314) from the Japanese sponge Stylissa aff. massa inhibits geranylger-anyltransferase type I and the fungus Candida albicans (1302). Like many of these 2-aminoimidazole alkaloids, 1310-1314 were isolated as acid salts trifluoroacetic acid salts in these cases. 

Aiello A, D Esposito M, Fattorusso E, Menna M, Miiller WEG, Perovic-Ottstadt S, Schroder HC (2006) Novel Bioactive Bromopyrrole Alkaloids from the Mediterranean Sponge Axinella verrucosa. Bioorg Med Chem 14 17... 

Supriyono A, Schwarz B, Wray V, Witte L, Muller WEG, van Soest R, Sumaryono W, Proksch P (1995) Bioactive Alkaloids from the Tropical Marine Sponge Axinella carteri. Z Naturforsch 50c 669... 

Tsukamoto S, Tane K, Ohta T, Matsunaga S, Fusetani N, van Soest RWM (2001) Four New Bioactive Pyrrole-Derived Alkaloids from the Marine Sponge Axinella brevistyla. J Nat Prod 64 1576... 

Urban S, de Almeida Leone P, Carroll AR, Fechner GA, Smith J, Hooper JNA, Quinn RJ (1999) Axinellamines A-D, Novel Imidazo-Azolo-Imidazole Alkaloids from the Australian Marine Sponge Axinella sp. J Org Chem 64 731... 

Fig. (9). Aminoimidazole and guanidine type of alkaloids from Axinella carteri.

Ottstadt, S., Schroeder, H. C., (2006). Novel bioactive bromopyrrole alkaloids from the Mediterranean Axinella verrucosa. Bioorg. Med. Chem. 14, 17-24. 

Vergne, C., Boury-Esnault, N., Perez, T., Martin, M., Adeline, M., Dau, E. T. H., Al-Mourabit, A., (2006). Verpacamides A-D, a sequence of C11N5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti Possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids. Org. Lett. 8, 2421-2424. 

Tsukamoto, S., Tane, K., Ohta, T., Matsunaga, S., Fusetani, N., van Soest, R. W. M., (2001). Four new bioactive pyrrole-derived alkaloids from the marine sponge Axinella brevistyla. J. Nat. Prod. 64, 1576-1578. 

Alkaloid from the marine sponge Axinella sp. Pale yellow gum. [a]u —26.2 (c, 0.08 in CHCI3). 

Structural Characterization of Donnazoies A andB, NovelPyrrole-Aminoimidazole Alkaloids from the Marine Sponge Axinella donnai... 

Aiello, A., D Esposito, M., Fattorusso, E., Menna, M., Muller, W.E.G., Perovic-Ottstadt, S., Tsuruta, H., Gulder, T.A.M., and Bringmann, G. (2005) Daminin, a bioactive pyrrole alkaloid from the Mediterranean sponge Axinella damicomis. Tetrahedron, 61, 7266—7270. 

Kuramoto, M Miyake, N Ishimaru, Y Ono, N., and Uno, H. (2008) Cylindradines A and B novel bromopyrrole alkaloids from the marine sponge Axinella cylindratus. Org. Lett, 10, 5465-5468. 

---