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{{short description|Cyclic peptide part of a group of toxins present in Amanita mushrooms}} |
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{{distinguish|Amanin}} |
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{{lowercasetitle}} |
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{{DISPLAYTITLE:''beta''-Amanitin}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 452409502 |
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| Name=β-Amanitin |
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| Watchedfields = changed |
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| ImageFile=beta-amanitin structure.png |
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| verifiedrevid = 446180075 |
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| ImageSize=220px |
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|Name=β-Amanitin |
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|ImageFile=beta-amanitin structure.png |
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| ImageFile2=File:B-amanitin 3D BS.png |
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| ImageSize2=220px |
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|IUPACName= |
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|OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=21150-22-1 |
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| CASNo=21150-22-1 |
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| PubChem=2276 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| UNII = G729YPP47L |
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| PubChem=2276 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 26234939 |
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| ChemSpiderID = 26234939 |
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| InChI = 1/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)/t16-,17-,19+,23-,24-,25-,26-,27-,31-,32-,64?/m0/s1 |
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| InChI = 1/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)/t16-,17-,19+,23-,24-,25-,26-,27-,31-,32-,64?/m0/s1 |
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| InChIKey = IEQCUEXVAPAFMQ-JAXJKTSHBD |
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| InChIKey = IEQCUEXVAPAFMQ-JAXJKTSHBD |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)/t16-,17-,19+,23-,24-,25-,26-,27-,31-,32-,64?/m0/s1 |
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| StdInChI = 1S/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)/t16-,17-,19+,23-,24-,25-,26-,27-,31-,32-,64?/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IEQCUEXVAPAFMQ-JAXJKTSHSA-N |
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| StdInChIKey = IEQCUEXVAPAFMQ-JAXJKTSHSA-N |
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| SMILES=O=C(NCC(N(C(NCC(N(C3)C(N(CC(O)=O)C(N54C(O)C5)=O)=O)=O)=O)()(C)CC)=O)(CC1=C(S3=O)NC2=C1C=CC(O)=C2)NC(((C)(O)CO)()N4=O)=O |
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| SMILES=O=C(NCC(N(C(NCC(N(C3)C(N(CC(O)=O)C(N54C(O)C5)=O)=O)=O)=O)()(C)CC)=O)(CC1=C(S3=O)NC2=C1C=CC(O)=C2)NC(((C)(O)CO)()N4=O)=O |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>39</sub>H<sub>53</sub>N<sub>9</sub>O<sub>15</sub>S |
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| Formula=C<sub>39</sub>H<sub>53</sub>N<sub>9</sub>O<sub>15</sub>S |
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| MolarMass=919.95 g/mol |
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| MolarMass=919.95 g/mol |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''''beta''-Amanitin''' or '''β-amanitin''' is a ] ] of eight ]s. It is an ], a group of ]s isolated from and found in several members of the '']'' genus of ]s, one being the Death cap ('']'') as well as the ], a complex of similar species, principally '']'' and '']''. |
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'''β-Amanitin''' ('''''beta''-Amanitin''') is a ] comprising eight ]s. It is part of a group of ]s called ]s, which can be found in several ]s belonging to the genus '']''. Some examples are the death cap ('']'') and members of the ] complex, which includes '']'' and '']''. Due to the presence of ], β-Amanitin, ] and ] these mushrooms are highly lethal to human beings. |
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] |
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==See also== |
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== Toxicity == |
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The lethal dose of amanitoxins is 0.1 mg/kg of body weight of humans. The average Amanita mushroom contains 3–5 mg of amanitoxins, so one 40–50 g mushroom could kill an average adult.<ref>{{cite journal |author1=G. Shoham |author2=D.C. Rees |author3=W.N. Lipscomb |author4=G. Zanotti |author5=Th. Wieland | year = 1984 | journal = Journal of the American Chemical Society | volume = 106 |issue=16 | pages = 4606–4615 | title = Crystal and Molecular Structure of S-Deoxoamaninamide: A synthetic Analogue of Amanita Toxins | doi=10.1021/ja00328a051}}</ref> The U.S. ] (OSHA) permits a ] exposure of up to 5 mg/m<sup>3</sup> of β-Amanitin dust.<ref name=":0">, Retrieved on 12 March 2013.</ref> |
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=== Symptoms of exposure === |
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β-Amanitin may cause irritation of the respiratory tract, headache, dizziness, nausea, shortness of breath, coughing, insomnia, diarrhea, gastrointestinal disturbances, back pain, urinary frequency, liver and kidney damage, or death if ingested or inhaled. If β-Amanitin comes in contact with skin, it may cause irritation, burns, redness, severe pain, and could be absorbed through the skin, causing similar effects to exposure via inhalation and ingestion. Contact with the eyes may result in irritation, corneal burns, and eye damage.<ref name=":0" /> Persons with pre-existing skin, eye, or central nervous systems disorders, impaired liver, kidney, or pulmonary function may be more susceptible to the effects of this substance.{{Citation needed|date=October 2024}} |
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== Physiological mechanism of action == |
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β-Amanitin is able to travel through the bloodstream to reach the organs in the body. While it damages all organs, damage to the liver and heart result in fatalities.{{citation needed|date=June 2024}} At the molecular level amanitin toxins cause damage to cells of these organs. The toxins may also cause disruptions in the plasma membranes resulting in organelles that are normally in the cytoplasm to be found in the extracellular matrix.<ref>{{cite journal |author1=J. Meldolesi |author2=G. Pelosi |author3=A. Brunelli |author4=E. Genovese | year = 1966 | journal = Virchows Archiv A | volume = 342 |issue=3 | pages = 221–235 | title = Electron Microscopic Studies on the Effects of Amanitin in Mice: Liver and Heart Lesions | doi=10.1007/bf00960591|pmid=5301504 |s2cid=12556291 }}</ref> beta-Amanitin is also an inhibitor of eukaryotic ] and ], and as a result, mammalian protein synthesis. It has not been found to inhibit RNA polymerase I or bacterial RNA polymerase.<ref>, Retrieved on 12 March 2013.</ref> Because it inactivates the RNA polymerases, the liver is unable to repair the damage that beta-Amanitin causes and the cells of the liver disintegrate and the liver dissolves.<ref>, "]", Retrieved on 12 March 2013.</ref> |
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== Scientific analysis == |
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Due to its lethality and its widespread presence in the genus '']'', which is found across the globe, β-Amanitin has been extensively studied in the field of ]. In particular, ], Nobel laureate, greatly contributed to characterizing this protein. Not only did Lipscomb determine how to successfully retrieve and purify this life-threatening protein, but he also determined the molecular structure by ] in a time before this technique was widely utilized.<ref name=Kostansek>{{cite journal |author1=E.C. Kostansek |author2=W.N. Lipscomb |author3=R.R. Yocum |author4=W.E. Thiessen | year = 1978 | journal = Biochemistry | volume = 17 |issue=18 | pages = 3790–3795 | title = Conformation of the Mushroom Toxin β-Amanitin in the Crystalline State | doi=10.1021/bi00611a019|pmid=698197 }}</ref> |
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=== Collection and purification === |
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Due to its extreme lethality, as well as it being only commercially available at certain times and then at an extremely high cost, '']'' had to be retrieved from the wild in order to collect the β-Amanitin protein. This was first achieved by collecting ''A. phalloides'' fruiting bodies in New Jersey in 1975. These mushrooms were then dried for 24 hours and then ground in a blender with water. The slurry created was ] further to break open any intact cells, and after this a brown syrup extract containing the toxins was collected. This extract was then taken through various separation methods to isolate the toxins themselves. The toxins were then desalted and taken through four different methods of sephadex and acidic protein purification.<ref>{{cite journal | author = R. Rogers Yocum | year = 1978 | journal = Biochemistry | volume = 17 | pages = 3786–3789 | title = New Laboratory Scale Purification of & Amanitin from American Amanit a phalloides | issue = 18 | doi=10.1021/bi00611a018| pmid = 568002 }}</ref> |
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=== Crystallization === |
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The structure of β-Amanitin was determined using ]. The crystallization and analysis were performed by Edward C. Kostansek and William H. Lipscomb in 1978. They crystallized β-Amanitin by dissolving a purified sample in almost pure ethanol in a round bottom flask. The flask was left open overnight and crystals formed as the ethanol evaporated. This is considered to be an incredibly easy crystallization to perform.<ref name=Kostansek/> |
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== See also == |
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== References == |
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{{reflist}} |
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== External links == |
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{{Poisonous Amanitas}} |
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{{Poisonous Amanitas}} |
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{{Toxins}} |
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{{Toxins}} |
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{{DEFAULTSORT:Amanitin, beta-}} |
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{{DEFAULTSORT:Amanitin, alpha-}} |
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