Abstract
Two glycosidic toxins, prymnesin-1 (PRM1) and prymnesin-2 (PRM2) have been isolated from cultured cells of the red tide phytoflagellate Prymnesium parvum, and the gross structure of PRM2 C96H136Cl3NO35 has been reported in a previous contribution. The molecule possesses unique structural features: a C90 unbranched carbon chain except for a single methyl, five contiguous ether rings (6/6/6/7/6), four distinct 1,6-dioxadecalin units, conjugated double and triple bonds, chlorine and nitrogen atoms, and an uncommon l-xylose. Potent ichthyotoxic and hemolytic properties of the two toxins were also demonstrated. However, the stereochemistry of PRM2 and the structure of PRM1 remained unknown. In the present paper the relative stereochemistry of the polycyclic ether moiety of PRM2 and the structure of PRM1 C107H154Cl3NO44 are reported. Structural elucidation was carried out by extensive analysis of NMR data. Difficulties arising from the poor solubility of the toxins in NMR solvents were overcome by preparing N-...
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