Tetrodonic acid-like substance; a possible precursor of tetrodotoxin.
A tetrodonic acid-like substance which was hardly distinguishable from authentic tetrodonic acid in thin-layer chromatography, high performance liquid chromatography, etc., was successfully purified from the ribbon worm and flatworm by a method consisting mainly of Bio-Gel P-2 column chromatography. The tetrodonic acid-like substance showed a specific toxicity of approximately 700 mouse units/mg as tetrodotoxin, unlike tetrodonic acid which is a completely non-toxic substance. Instrumental analyses including gas chromatography-mass spectrometry, secondary ion mass spectrometry and thin-layer chromatography/fast atom bombardment mass spectrometry disclosed that the tetrodonic acid-like substance had a structure similar to, but not the same as, that of tetrodotoxin. This, along with its high convertibility into tetrodotoxin during storage and other experimental operations, suggested that the tetrodonic acid-like substance is a precursor of tetrodotoxin.
Noguchi
T
T
Laboratory of Marine Biochemistry, Faculty of Agriculture, University of Tokyo, Japan.
Ali
A E
AE
Arakawa
O
O
Miyazawa
K
K
Kanoh
S
S
Shida
Y
Y
Nishio
S
S
Hashimoto
K
K
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004588:Electrophoresis, Cellulose Acetate; D008401:Gas Chromatography-Mass Spectrometry; D006863:Hydrogen-Ion Concentration; D007448:Invertebrates; D008297:Male; D013058:Mass Spectrometry; D051379:Mice; D010986:Platyhelminths; D011799:Quinazolines / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D013056:Spectrophotometry, Ultraviolet; D013779:Tetrodotoxin / Q000737:chemistry*
D011799:Quinazolines; C059207:tetrodonic acid; D013779:Tetrodotoxin