Palytoxin
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IUPAC name
(2S,3R,5R,6E,8R,9S)-10-[(2R,3R,4R,5S,6R)-6-[(1S,2R,3S,4S,5R,11S)-11-{[(1R,3S,5S,7R)-5-[(8S)-9-[(2R,3R,4R,5R,6S)-6-[(2S,3S,4E,6S,9R,10R)-10-[(2S,4R,5S,6R)-6-[(2R,3R)-4-[(2R,3S,4R,5R,6S)-6-[(2S,3Z,5E,8R,9S,10R,12Z,17S,18R,19R,20R)-20-{[(2R,3R,4R,5S,6R)-6-[(1Z,3R,4R)-5-[(1S,3R,5R,7R)-7-{2-[(2R,3R,5S)-5-(aminomethyl)-3-hydroxyoxolan-2-yl]ethyl}-2,6-dioxabicyclo[3.2.1]octan-3-yl]-3,4-dihydroxypent-1-en-1-yl]-3,4,5-trihydroxyoxan-2-yl]methyl}-2,8,9,10,17,18,19-heptahydroxy-14-methylidenehenicosa-3,5,12-trien-1-yl]-3,4,5-trihydroxyoxan-2-yl]-2,3-dihydroxybutyl]-4,5-dihydroxyoxan-2-yl]-2,6,9,10-tetrahydroxy-3-methyldec-4-en-1-yl]-3,4,5,6-tetrahydroxyoxan-2-yl]-8-hydroxynonyl]-1,3-dimethyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]methyl}-1,2,3,4,5-pentahydroxydodecyl]-3,4,5-trihydroxyoxan-2-yl]-2,5,8,9-tetrahydroxy-N-[(1E)-2-[(3-hydroxypropyl)-C-hydroxycarbonimidoyl]eth-1-en-1-yl]-3,7-dimethyldec-6-enimidic acid
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| Identifiers | |
77734-91-9 
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| 3D model (Jmol) | Interactive image |
| ChemSpider |
9280425
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| PubChem | 11105289 |
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| Properties | |
| C129H223N3O54 | |
| Molar mass | 2680.1386 g.mol−1 |
| Appearance | white amorphous hygroscopic solid |
| Melting point | decomposes at 300°C |
| Very soluble in water, dimethyl sulfoxide, pyridine; slightly soluble in methanol and ethanol; insoluble in chloroform and diethyl ether | |
| Hazards | |
| Main hazards | Highly toxic, symptoms of poisoning include: chest pains, breathing difficulties, tachycardia, unstable blood pressure and hemolysis. |
| GHS pictograms |  |
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EU classification (DSD)
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 T+ |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Palytoxin is an intense vasoconstrictor, and is considered to be one of the most toxic non-protein substances known, second only to maitotoxin in terms of toxicity in mice. Palytoxin is a natural compound, (chemically a fatty alcohol) that is produced by several marine species and can be found in many more species due to a process known as biomagnification. Palytoxin was originally isolated in 1971 in Hawaii from the seaweed-like coral "limu-make-o-Hana" (Seaweed of Death from Hana). Later, in 1982 its full chemical structure was published by Prof. Daisuke Uemura and co-workers at Nagoya University.Yoshito Kishi's group at Harvard University first synthesized palytoxin in 1994. Palytoxin targets the sodium-potassium pump protein by locking it into a position where it allows passive transport of both sodium and potassium ions, thereby destroying the ion gradient that is essential for most cells. Because palytoxin affects every cell in the body, the symptoms are very different for the various routes of exposure. The most common exposure in humans is by ingestion or inhalation. The onset of symptoms is rapid, and death usually follows quickly.
According to an ancient Hawaiian legend, (Malo 1951) on the island of Maui near the harbour of Hana there was a village of fishermen haunted by a curse. Upon their return from the sea one of the fishermen went missing. One day, enraged by another loss, the fishermen assaulted a hunchbacked hermit deemed culprit of the town's misery. While ripping off the cloak from the hermit the villagers were shocked because they uncovered rows of sharp and triangular teeth within huge jaws. A shark god had been caught. It was clear that the missing villagers had been eaten by the god on their journeys to the sea. The men mercilessly tore the shark god into pieces, burned him and threw the ashes into a tide pool near the harbour of Hana. Shortly after, a thick brown moss started to grow on the walls of the tide pool causing instant death to victims hit by spears smeared with the moss. Thus was the evil of the demon. The moss growing in the cursed tide pool became known as "limu-make-o-Hana" which literally means "seaweed of death from Hana." The Hawaiians believed that an ill curse came over them if they tried to collect the deadly seaweed.
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