6,11-Dideoxytetrodotoxin from the puffer fish, Fugu pardalis

The presence of an unknown dideoxy analog of tetrodotoxin was suggested on the liquid chromatography/electrospray ionization-mass spectrometry mass chromatogram of the ovaries of the puffer fish, Fugu pardalis, in single ion monitoring mode to detect at m/z 288. We succeeded to isolate this analog (approximately 0.4 mg) from 200 g of the ovaries and the structure was determined as 6,11-dideoxytetrodotoxin by spectroscopic methods (high resolution-fast atom bombardment-MS and NMR spectroscopy). The discovery of the new analog is highly significant with respect to the biosynthesis or metabolism of tetrodotoxin. We also roughly determined the value of IC50 (mice, intraperitoneal) for 6,11-dideoxytetrodotoxin as 420 μg/kg and thus it is 42 times less toxic than tetrodotoxin.