Palytoxin

Hygroscopic solid

Fixed

> 300 ° C

• Soluble in water, DMSO, pyridine and
• Insoluble in acetone and chloroform

Template: Infobox chemical / molecular formula search available

Palytoxin is a toxin of dinoflagellate Ostreopis siamensis, which is extracted by some animals such as the soft coral Palythoa toxica or Zoanthids from uneaten plankton and used for protection against predators. Until the discovery and structural elucidation of palytoxin maitotoxin was the largest non-polymeric and non- natural substance composed of amino acids with the longest continuous carbon chain (115 links ).

History

Palytoxin took a long time as a poison for spears in the indigenous population of Hawaii use. Its complex structure and absolute configuration was elucidated in the years 1981-1982. A first total synthesis of the Palytoxins was established in 1994 by a working group under Yoshito Kishi, a professor at Harvard University, gemeldet.Bis the present day is the synthesis of this natural product with its 64 stereogenic centers as one of the greatest achievements in chemical synthesis.

Toxicity

Palytoxin is one of the most toxic organic substances with an LD50 ( house mouse ) of less than 100 ng per kg body weight; maitotoxin only and a number of proteins have a higher acute toxicity. The toxic effect is due to a serious interference with active cellular transport systems for ions, so-called ATPases. Palytoxin causes a configuration change of the Na-K- ATPase in such a way that the direction of specificity of the pumping action ( for three pumped from the cell, Na ions with the consumption of one molecule ATP two K ion transported into the cell ) is removed. This leads to the decrease of the concentration gradient between the extracellular and the intracellular space, therefore the osmotic pressure, the membrane potential ( depolarization ), etc. with the appropriate fatal effect on the cells or the organism. Symptoms of poisoning can be derived from the operation of deduce: hemolysis, rhabdomyolysis, severe muscle spasms, bronchospasm, hypertension, pathologically altered ECG. The symptoms of poisoning are rapid and eventually lead to a quick death within minutes.

Use

The toxin was used in Hawaii to poison spears. However, it was soon discontinued it because the poison causes greatest torments.