Pinnamine, Pinna muricata

A seventh novel alkaloidal toxin, pinnamine, was isolated and pnrified from the viscera of the Okinawan bivalve Pinna muricata (Takada et al. 2000). Its gross stmctnre, clarified by a detailed analysis of NMR and CD spectra, includes a 9-azabicyclo[4.2.1]nonane pharmacophoric element (Fig. 18.6A). Further synthetic studies have not only confirmed the absolute stereochemistiy of the molecule, but have also allowed stereocontrolled access to a non-natural congener, 5-epi-pinnamine, of the natural product (Kigoshi et al. 2001 Hjelmgaard et al. 2005). 

Pinnamine, an Alkaloidal Marine Toxin from Pinna muricata. 163... 

Takada, N., Iwatsuki, M., Suenaga, K., and Uemura, D. (2000) Pinnamine, an alkaloidal marine toxin isolated from Pinna muricata. Tetrahedron Lett., 41, 6425-6428. 

Pinnamine and oxazinins 1-6 were isolated from the bivalves Pinna muricata (pinnamine) harvested in Japan (Okinawa) and Mytilus galloprovincialis (oxazanins) harvested in the Adriatic Sea. Pinnamine is toxic (LD99 O.Smgkg ) by intraperitoneal injection in mice, and oxazinin-1 is moderately cytotoxic to murine fibrosarcoma WEHI-164 cells, with an IC50 of 16.5 [xgml. ... 

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