D. Complex Polycyclic Compounds
149
a culture of the blue-green alga Aphanizomenon flos-aquae a toxin that was
nearly identical with saxitoxin in a number of physical and physiological
parameters.
The second isolation resulted from an epidemiological investigation of
toxic crabs in the Ryukyu and Amami islands by Hashimoto and co-workers
(1967a). A number of species were screened and from toxic specimens of the
crab Zosimus aeneus a toxin was isolated that is almost certainly identical
with saxitoxin (Konosu et al, 1968; Noguchi et al, 1969).
While there is no way of detecting the presence of saxitoxin in infested
shellfish except by bioassay in mice, there have been, from time to time,
reports of massive fish kills that were presumably caused by dinofiagellates.
One such occurrence was reported by Hashimoto and co-workers (1968),
who isolated the toxin produced by the planktonic organism Peridinium
polonicum that had been responsible for fish mortality in Lake Sagami near
Tokyo in 1962. Hashimoto et al (1968) were able to prepare a crystalline
though unstable reineckate of the toxic base which they called glenodinine.
It appeared from spectral data and spot tests that glenodinine is an alkaloidal
substance possessing a substituted piperidine moiety and a sulfhydryl group.
3.
TETRODOTOXIN
a. Introduction
Interest in another potent marine toxin, tetrodotoxin, which along with
saxitoxin is a complex nitrogen heterocycle, was originally generated because
tetrodotoxin, too, presented a public health hazard, having a lethal dose of the
same order of magnitude as saxitoxin. Tetrodotoxin also proved to be a
relatively small, basic molecule of limited solubility in organic solvents. On
the other hand, these superficial similarities are matched by considerable
differences. Poisoning by tetrodotoxin has long been traced to members of a
single family of fishes, the Tetraodontidae, and only the viscera, largely the
ovaries and the liver, harbor the toxin. Geographically, puffer fish poisoning is
known only from Japan, where puffer fish {fugu) is a culinary delicacy and
where elaborate precautions are taken to prevent human intoxication.
Halstead (1967) has described the fugu cult in great detail. Briefly, only trained
and licensed personnel may handle the fish in the market and remove the
viscera. In spite of these precautions 500 intoxications were reported in
Japan in 1958-1959, of which 294 proved to be fatal (Tsuda, 1966).
Professor Tsuda, the foremost pioneer in the structural elucidation of
tetrodotoxin, writes (Tsuda, 1966) that 2000-year-old Chinese medical books
report of puffer fish poisonings and that fugu bones have been found in
Japanese burial sites that are some fifteen hundred years old. Yet the earliest
reports in the Japanese literature on fugu intoxication date back only about
four hundred years.
149
a culture of the blue-green alga Aphanizomenon flos-aquae a toxin that was
nearly identical with saxitoxin in a number of physical and physiological
parameters.
The second isolation resulted from an epidemiological investigation of
toxic crabs in the Ryukyu and Amami islands by Hashimoto and co-workers
(1967a). A number of species were screened and from toxic specimens of the
crab Zosimus aeneus a toxin was isolated that is almost certainly identical
with saxitoxin (Konosu et al, 1968; Noguchi et al, 1969).
While there is no way of detecting the presence of saxitoxin in infested
shellfish except by bioassay in mice, there have been, from time to time,
reports of massive fish kills that were presumably caused by dinofiagellates.
One such occurrence was reported by Hashimoto and co-workers (1968),
who isolated the toxin produced by the planktonic organism Peridinium
polonicum that had been responsible for fish mortality in Lake Sagami near
Tokyo in 1962. Hashimoto et al (1968) were able to prepare a crystalline
though unstable reineckate of the toxic base which they called glenodinine.
It appeared from spectral data and spot tests that glenodinine is an alkaloidal
substance possessing a substituted piperidine moiety and a sulfhydryl group.
3.
TETRODOTOXIN
a. Introduction
Interest in another potent marine toxin, tetrodotoxin, which along with
saxitoxin is a complex nitrogen heterocycle, was originally generated because
tetrodotoxin, too, presented a public health hazard, having a lethal dose of the
same order of magnitude as saxitoxin. Tetrodotoxin also proved to be a
relatively small, basic molecule of limited solubility in organic solvents. On
the other hand, these superficial similarities are matched by considerable
differences. Poisoning by tetrodotoxin has long been traced to members of a
single family of fishes, the Tetraodontidae, and only the viscera, largely the
ovaries and the liver, harbor the toxin. Geographically, puffer fish poisoning is
known only from Japan, where puffer fish {fugu) is a culinary delicacy and
where elaborate precautions are taken to prevent human intoxication.
Halstead (1967) has described the fugu cult in great detail. Briefly, only trained
and licensed personnel may handle the fish in the market and remove the
viscera. In spite of these precautions 500 intoxications were reported in
Japan in 1958-1959, of which 294 proved to be fatal (Tsuda, 1966).
Professor Tsuda, the foremost pioneer in the structural elucidation of
tetrodotoxin, writes (Tsuda, 1966) that 2000-year-old Chinese medical books
report of puffer fish poisonings and that fugu bones have been found in
Japanese burial sites that are some fifteen hundred years old. Yet the earliest
reports in the Japanese literature on fugu intoxication date back only about
four hundred years.