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γ-Amanitin

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(Redirected from Gamma-Amanitin) Cyclic peptide part of a group of toxins present in Amanita mushrooms
γ-Amanitin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C39H54N10O13S/c1-5-16(2)31-36(59)42-12-29(54)43-26-15-63(62)38-22(21-7-6-19(51)8-23(21)46-38)10-24(33(56)41-13-30(55)47-31)44-37(60)32(17(3)18(4)50)48-35(58)27-9-20(52)14-49(27)39(61)25(11-28(40)53)45-34(26)57/h6-8,16-18,20,24-27,31-32,46,50-52H,5,9-15H2,1-4H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58)/t16-,17-,18-,20+,24-,25-,26-,27-,31-,32-,63?/m0/s1Key: WVHGJJRMKGDTEC-ZUROAWGWSA-N
  • InChI=1/C39H54N10O13S/c1-5-16(2)31-36(59)42-12-29(54)43-26-15-63(62)38-22(21-7-6-19(51)8-23(21)46-38)10-24(33(56)41-13-30(55)47-31)44-37(60)32(17(3)18(4)50)48-35(58)27-9-20(52)14-49(27)39(61)25(11-28(40)53)45-34(26)57/h6-8,16-18,20,24-27,31-32,46,50-52H,5,9-15H2,1-4H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58)/t16-,17-,18-,20+,24-,25-,26-,27-,31-,32-,63?/m0/s1Key: WVHGJJRMKGDTEC-ZUROAWGWBF
SMILES
  • CC(C)1C(=O)NCC(=O)N2CS(=O)c3c(c4ccc(cc43)O)C(C(=O)NCC(=O)N1)NC(=O)(NC(=O)5C(CN5C(=O)(NC2=O)CC(=O)N)O)(C)(C)O
Properties
Chemical formula C39H54N10O13S
Molar mass 902.97 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

γ-Amanitin (gamma-Amanitin) is a cyclic peptide of eight amino acids. It is an amatoxin, a group of toxins isolated from and found in several members of the mushroom genus Amanita, one being the death cap (Amanita phalloides) as well as the destroying angel, a complex of similar species, principally A. virosa and A. bisporigera. The compound is highly toxic, inhibits RNA polymerase II, disrupts synthesis of mRNA, and can be fatal.

Toxicity

Amatoxins selectively inhibit Eukaryotic RNA polymerase II by tightly to the enzyme and severely inhibits translocation along the DNA template; thus the synthesis of mRNA and proteins stops. Amatoxin consumption is characterized by a long asymptomatic period of a few hours (up to a day or more) followed by quick physiological decline due to acute hepatic and tubular necrosis. γ-Amanitin has been found to have similar levels of toxicity to other amatoxins such as α-Amanitin.

See also

References

  1. PubChem. "Hazardous Substances Data Bank (HSDB) : 3460". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-05-04.
  2. de Mercoyrol, L.; Job, C.; Job, D. (1989-02-15). "Studies on the inhibition by alpha-amanitin of single-step addition reactions and productive RNA synthesis catalysed by wheat-germ RNA polymerase II". The Biochemical Journal. 258 (1): 165–169. doi:10.1042/bj2580165. ISSN 0264-6021. PMC 1138336. PMID 2467661.
  3. Vetter, János (2023-08-07). "Amanitins: The Most Poisonous Molecules of the Fungal World". Molecules (Basel, Switzerland). 28 (15): 5932. doi:10.3390/molecules28155932. ISSN 1420-3049. PMC 10421264. PMID 37570902.
Poisonous Amanita mushrooms
Subgenus
Amanita
Amanita
Species
Compounds
Subgenus
Amanitina
Lepidella
(=Saproamanita)
Species
Compounds
  • unknown toxin
Phalloideae
Species
Destroying angels
Other members
Compounds
Amatoxins
Phallotoxins
Virotoxins
Other compounds
Roanokenses
Species
Compounds
Validae
Species
Compounds
Bacterial
toxins
Exotoxin
Gram
positive
Bacilli
Clostridium:
Other:
Cocci
Staphylococcus
Actinomycetota
Gram
negative
Mechanisms
Endotoxin
Virulence
factor
Mycotoxins
Plant toxins
Invertebrate
toxins
Scorpion:
Spider:
Mollusca:
Vertebrate
toxins
Fish:
Amphibian:
Reptile/
Snake venom:
  • note: some toxins are produced by lower species and pass through intermediate species
Categories: