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Other names 1-L-Aspartic acid-3-isoleucine-alpha-amanitin | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
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Properties | |
C39H53N9O13S | |
Molar mass | 887.96 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Amanullinic acid is a cyclic nonribosomal peptide. It is an amatoxin, all of which are found in several members of the mushroom genus Amanita . Amanullinic acid is relatively non-toxic( oral LD50 >20 mg/kg in mice). [1]
A cyclic compound is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon, none of the atoms are carbon, or where both carbon and non-carbon atoms are present. Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic, in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size numbers in the many billions.
Nonribosomal peptides (NRP) are a class of peptide secondary metabolites, usually produced by microorganisms like bacteria and fungi. Nonribosomal peptides are also found in higher organisms, such as nudibranchs, but are thought to be made by bacteria inside these organisms. While there exist a wide range of peptides that are not synthesized by ribosomes, the term nonribosomal peptide typically refers to a very specific set of these as discussed in this article.
Amatoxin is the collective name of a subgroup of at least eight related toxic compounds found in several genera of poisonous mushrooms, most notably the death cap and several other members of the genus Amanita, as well as some Conocybe, Galerina and Lepiota mushroom species. Amatoxins are lethal in even small doses. Unlike many ingested poisons they are not destroyed by heat so cooking the poisonous mushrooms does not diminish their lethality which can be as little as eating half a mushroom.
Like other amatoxins, amanullinic acid is an inhibitor of RNA polymerase II.
RNA polymerase II is a multiprotein complex. It is one of the three RNAP enzymes found in the nucleus of eukaryotic cells. It catalyzes the transcription of DNA to synthesize precursors of mRNA and most snRNA and microRNA. A 550 kDa complex of 12 subunits, RNAP II is the most studied type of RNA polymerase. A wide range of transcription factors are required for it to bind to upstream gene promoters and begin transcription.
Amanita phalloides, commonly known as the death cap, is a deadly poisonous basidiomycete fungus, one of many in the genus Amanita. Widely distributed across Europe, but now sprouting in other parts of the world, A. phalloides forms ectomycorrhizas with various broadleaved trees. In some cases, the death cap has been introduced to new regions with the cultivation of non-native species of oak, chestnut, and pine. The large fruiting bodies (mushrooms) appear in summer and autumn; the caps are generally greenish in colour with a white stipe and gills. Cap colour is variable, including white forms and thus not a reliable identifier.
The name destroying angel applies to several similar, closely related species of deadly all-white mushrooms in the genus Amanita. They are Amanita bisporigera and A. ocreata in eastern and western North America, and A. virosa in Europe. Another very similar species, A. verna or fool's mushroom, was first described in France.
The genus Amanita contains about 600 species of agarics including some of the most toxic known mushrooms found worldwide, as well as some well-regarded edible species. This genus is responsible for approximately 95% of the fatalities resulting from mushroom poisoning, with the death cap accounting for about 50% on its own. The most potent toxin present in these mushrooms is α-amanitin.
alpha-Amanitin or α-amanitin is a cyclic peptide of eight amino acids. It is possibly the most deadly of all the amatoxins, toxins found in several species of the mushroom genus Amanita, one being the death cap as well as the destroying angel, a complex of similar species, principally A. virosa and A. bisporigera. It is also found in the mushrooms Galerina marginata and Conocybe filaris. The oral LD50 of amanitin is approximately 0.1 mg/kg for rats.
Mushroom poisoning refers to harmful effects from ingestion of toxic substances present in a mushroom. These symptoms can vary from slight gastrointestinal discomfort to death. The toxins present are secondary metabolites produced by the fungus. Mushroom poisoning is usually the result of ingestion of wild mushrooms after misidentification of a toxic mushroom as an edible species. The most common reason for this misidentification is close resemblance in terms of colour and general morphology of the toxic mushrooms species with edible species. To prevent mushroom poisoning, mushroom gatherers familiarize themselves with the mushrooms they intend to collect, as well as with any similar-looking toxic species. The safety of eating wild mushrooms may depend on methods of preparation for cooking.
Amanita virosa, commonly known in Europe as the destroying angel, is a deadly poisonous basidiomycete fungus, one of many in the genus Amanita. Occurring in Europe, A. virosa associates with various deciduous and coniferous trees. The large fruiting bodies appear in summer and autumn; the caps, stipes and gills are all white in colour.
Amanin is a cyclic peptide. It is one of the amatoxins, all of which are found in several members of the mushroom genus Amanita.
Amanita velosa or bittersweet orange ringless amanita is an edible species of agaric found in California, as well as Oregon and Baja California.
Amanita ocreata, commonly known as the death angel, destroying angel, angel of death or more precisely western North American destroying angel, is a deadly poisonous basidiomycete fungus, one of many in the genus Amanita. Occurring in the Pacific Northwest and California floristic provinces of North America, A. ocreata associates with oak trees. The large fruiting bodies generally appear in spring; the cap may be white or ochre and often develops a brownish centre, while the stipe, ring, gill and volva are all white.
beta-Amanitin or β-amanitin is a cyclic peptide comprising eight amino acids. It is part of a group of toxins called amatoxins, which can be found in several mushrooms belonging to the genus Amanita. Some examples are the death cap and members of the destroying angel complex, which includes A. virosa and A. bisporigera. Due to the presence of α-amanitin, β-amanitin, γ-amanitin and ε-amanitin these mushrooms are highly lethal to human beings.
gamma-Amanitin or γ-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 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.
The phallotoxins consist of at least seven compounds, all of which are bicyclic heptapeptides, isolated from the death cap mushroom (Amanita phalloides).
Amanullin is a cyclic peptide. It is an amatoxin, all of which are found in several members of the mushroom genus Amanita. The oral LD50 of amanullin is approximately 20 mg/kg in mice; however, it is non-toxic in humans.
Promanullin is a cyclic nonribosomal peptide. It is an amatoxin, all of which are found in the mushroom genus Amanita.
epsilon-Amanitin or ε-amanitin is a cyclic peptide. It is an amatoxin, all of which are found in several members of the mushroom genus Amanita. The oral LD50 of ε-amanitin is approximately 0.1 mg/kg.
Amaninamide is a cyclic peptide. It is one of the amatoxins, all of which are found in several members of the mushroom genera Amanita, Lepiota and Galerina. It differs from alpha-amanitin in lacking the hydroxyl group on tryptophan. This alters its UV absorption spectrum but not its toxicity.
Amanita exitialis, also known as the Guangzhou destroying angel, is a mushroom of the large genus Amanita. It is distributed in eastern Asia, and probably also in India where it has been misidentified as A. verna. Deadly poisonous, it is a member of section Phalloideae and related to the death cap A. phalloides. The fruit bodies (mushrooms) are white, small to medium-sized with caps up to 7 cm (2.8 in) in diameter, a somewhat friable ring and a firm volva. Unlike most agaric mushrooms which typically have four-spored basidia, the basidia of A. exitialis are almost entirely two-spored. Eight people were fatally poisoned in China after consuming the mushroom in 2000, and another 20 have been fatally poisoned since that incident. Molecular analysis shows that the species has a close phylogenetic relationship with three other toxic white Amanitas: A. subjunquillea var. alba, A. virosa and A. bisporigera.
Amanita franchetii is a species of fungus in the Amanitaceae family. It was given its current name by Swiss mycologist Victor Fayod in 1889 in honor of French botanist Adrien René Franchet. A. franchetii occurs in Europe and North Africa with oaks, chestnuts, and pines.