Histrionicotoxins

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Harlequin poison dart ( Dendrobates histrionicus )

The histrionicotoxins are a group of alkaloids found in the skin of poison dart frogs .

Occurrence

The histrionicotoxins were found in the harlequin poison dart frog (Dendrobates histrionicus), rarely called the poison dart frog.

Representative

The main representatives include a. Histrionicotoxin (283A), allodihydro-histrionicotoxin (285C) and isodihydro-histrionicotoxin (285A).

  • (-) - Histrionicotoxin (283A)

  • (-) - Histrionicotoxin (285C)

  • (-) - Histrionicotoxin (285A)

properties

Histrionicotoxins are potent antagonists of the nicotinic acetylcholine receptor . The mechanism of action is complex and paradoxically involves a positive allosteric modulation of the postsynaptic receptors, making the motor endplates more susceptible to depolarization block .

From a chemical point of view, these substances are interesting because of the terminal alkyne groups (C≡C triple bond).

Individual evidence

  1. ^ A. Sinclair, RA Stockman: Thirty-five years of synthetic studies directed towards the histrionicotoxin family of alkaloids . In: Natural Product Reports . tape 24 , no. 2 , 2007, p. 298-326 , doi : 10.1039 / b604203c , PMID 17389999 .
  2. ↑ G. Habermehl, P. Hammann, H. Krebs: Naturstoffchemie . 3. Edition. Springer-Verlag, Berlin Heidelberg 2008, ISBN 978-3-540-73732-2 , p. 157 .
  3. ↑ Entry on Histrionicotoxins. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2020.
  4. ^ W. Burgermeister, WA Catterall, B. Witkop: Histrionicotoxin enhances agonist-induced desensitization of acetylcholine receptor. In: Proceedings of the National Academy of Sciences . Volume 74, Number 12, December 1977, pp. 5754-5758, PMID 272000 , PMC 431872 (free full text).
  5. Jump up ↑ Eva Bartels-Bernal, Edgar Diaz, Rosalina Cadena, Jorge Ramos, John W. Daly: Effect of histrionicotoxin on ion channels in synaptic and conducting membranes of electroplax of Electrophorus electricus. In: Cellular and Molecular Neurobiology. 3, 1983, p. 203, doi : 10.1007 / BF00710947 .