removed Category:Mycotoxins; added Category:Amatoxins using HotCat
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{{short description|Cyclic peptide part of a group of toxins present in Amanita mushrooms}} |
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{{lowercasetitle}} |
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{{chembox |
{{chembox |
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| verifiedrevid = |
| verifiedrevid = 452417160 |
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|Name=γ-Amanitin |
| Name=γ-Amanitin |
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|ImageFile=gamma-amanitin structure.png |
| ImageFile=gamma-amanitin structure.png |
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|ImageSize= |
| ImageSize=220px |
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| ImageFile2=Amanitin,gamma 3D BS.png |
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| ImageSize2=220px |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=21150-23-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=O=C(NCC(N[C@@](C(NCC(N[C@@H](C3)C(N[C@@H](CC(N)=O)C(N5[C@H]4C[C@@H](O)C5)=O)=O)=O)=O)([H])[C@@H](C)CC)=O)[C@H](CC1=C(S3=O)NC2=C1C=CC(O)=C2)NC([C@@]([C@@H](C)[C@@H](O)C)([H])N[C@@]4=O)=O |
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| UNII = ZOZ8ILM7WM |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 26234940 |
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| SMILES = CC[C@H](C)[C@H]1C(=O)NCC(=O)N[C@H]2CS(=O)c3c(c4ccc(cc4[nH]3)O)C[C@@H](C(=O)NCC(=O)N1)NC(=O)[C@@H](NC(=O)[C@@H]5C[C@H](CN5C(=O)[C@@H](NC2=O)CC(=O)N)O)[C@@H](C)[C@H](C)O |
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| 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/s1 |
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| InChIKey = WVHGJJRMKGDTEC-ZUROAWGWBF |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WVHGJJRMKGDTEC-ZUROAWGWSA-N |
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}} |
}} |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| Formula=C<sub>39</sub>H<sub>54</sub>N<sub>10</sub>O<sub>13</sub>S |
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| MolarMass=902.97 g/mol |
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| Appearance= |
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| Density= |
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| MeltingPt= |
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| BoilingPt= |
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| Solubility= |
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}} |
}} |
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|Section3={{Chembox Hazards |
|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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| AutoignitionPt = |
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| Autoignition= |
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}} |
}} |
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}} |
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''''' |
'''γ-Amanitin''' ('''''gamma''-Amanitin''') is a [[cyclic peptide]] of eight [[amino acid]]s. It is an [[amatoxin]], a group of [[toxin]]s 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 ''[[Amanita virosa|A. virosa]]'' and ''[[Amanita bisporigera|A. bisporigera]]''. The compound is highly toxic, inhibits [[RNA polymerase II]], disrupts synthesis of [[mRNA]], and can be fatal.<ref>{{Cite web |last=PubChem |title=Hazardous Substances Data Bank (HSDB) : 3460 |url=https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3460 |access-date=2024-05-04 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> |
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== |
== Toxicity == |
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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.<ref>{{Cite journal |last1=de Mercoyrol |first1=L. |last2=Job |first2=C. |last3=Job |first3=D. |date=1989-02-15 |title=Studies on the inhibition by alpha-amanitin of single-step addition reactions and productive RNA synthesis catalysed by wheat-germ RNA polymerase II |journal=The Biochemical Journal |volume=258 |issue=1 |pages=165–169 |doi=10.1042/bj2580165 |issn=0264-6021 |pmc=1138336 |pmid=2467661}}</ref> 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.<ref>{{Cite journal |last=Vetter |first=János |date=2023-08-07 |title=Amanitins: The Most Poisonous Molecules of the Fungal World |journal=Molecules (Basel, Switzerland) |volume=28 |issue=15 |pages=5932 |doi=10.3390/molecules28155932 |doi-access=free |issn=1420-3049 |pmc=10421264 |pmid=37570902}}</ref> γ-Amanitin has been found to have similar levels of toxicity to other amatoxins such as α-Amanitin. |
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== See also == |
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==References== |
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{{Reflist}} |
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{{Poisonous Amanitas}} |
{{Poisonous Amanitas}} |
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{{DEFAULTSORT:Amanitin, gamma-}} |
{{DEFAULTSORT:Amanitin, gamma-}} |
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[[Category: |
[[Category:Cyclic peptides]] |
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[[Category: |
[[Category:Phenols]] |
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[[Category:Amatoxins]] |
[[Category:Amatoxins]] |
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[[Category: |
[[Category:Hepatotoxins]] |
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[[Category: |
[[Category:Tryptamines]] |
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[[Category:Sulfoxides]] |
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{{biochem-stub}} |
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[[cs:Gama-amanitin]] |
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[[lt:Gama amanitinas]] |
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[[ja:Γ-アマニチン]] |
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Identifiers | |
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3D model (JSmol) |
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ChemSpider |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C39H54N10O13S | |
Molar mass | 902.97 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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.[1]
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.[2] 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.[3] γ-Amanitin has been found to have similar levels of toxicity to other amatoxins such as α-Amanitin.
Poisonous Amanita mushrooms
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Subgenus Amanita |
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Subgenus Amanitina |
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