Shellfish poisons.

Abstract

In our ongoing search for bioactive metabolites from marine organisms, novel shellfish poisons have been isolated. Pinnatoxins, which are amphoteric polyether compounds, were purified from the Okinawan bivalve Pinna muricata. Pinnatoxins show acute toxicity against mice and activate Ca2+ channels. Two novel alkaloids, pinnamine and pinnaic acid, were also obtained from P. muricata. Pinnaic acid inhibits cytosolic phospholipase (cPLA2). Pteriatoxins, which are pinnatoxin analogs, were isolated from the Okinawan bivalve Pteria penguin. A nanomole-order structure determination of pteriatoxins was achieved by the detailed analysis of 2D-NMR and ESI-TOF MS/MS. This review covers the isolation, structure determination, bioactivity, synthesis, and biogenesis of these shellfish poisons and related compounds.