Agaritine

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title: "Agaritine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["mycotoxins", "hydrazides", "hydroxymethyl-compounds", "alpha-amino-acids", "amino-acid-derivatives"] topic_path: "general/mycotoxins" source: "https://en.wikipedia.org/wiki/Agaritine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477243563 | ImageFile = Agaritine.svg | ImageFile_Ref = | ImageSize = 244 | ImageName = Stereo structural formula of agaritine ((2S)-2-amino) | ImageFile1 = Agaritine_3d_structure.png | ImageFile1_Ref = | ImageSize1 = 244 | ImageName1 = Ball and stick model of agaritine ((2S)-2-amino) | IUPACName = 2-[4-(Hydroxymethyl)phenyl]-glutamohydrazide | SystematicName = 2-Amino-4-{N'-[4-(hydroxymethyl)phenyl]hydrazinecarbonyl}butanoic acid | OtherNames = β-N-[γ-glutamyl]-4-hydroxymethylphenylhydrazine

N2-(γ-glutamyl)-4-hydroxymethylphenylhydrazine |Section1={{Chembox Identifiers | Abbreviations = AGT | CASNo = 2757-90-6 | CASNo_Ref = | UNII_Ref = | UNII = UX8Y7QVP8M | PubChem = 17688 | PubChem1 = 439517 | PubChem1_Comment = (2S)-2-amino | KEGG_Ref = | KEGG = C01550 | MeSHName = Agaritine | ChEBI_Ref = | ChEBI = 15336 | RTECS = MA1284000 | Beilstein = 757731 | PubChem2 = 439516 | ChemSpiderID_Ref = | ChemSpiderID = 388610 | SMILES = [O-]C(=O)C@@HCCC(=O)NNc1ccc(cc1)CO | InChI = 1/C12H17N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,10,14,16H,5-7,13H2,(H,15,17)(H,18,19)/t10-/m0/s1 | InChIKey = SRSPQXBFDCGXIZ-JTQLQIEIBZ | StdInChI_Ref = | StdInChI = 1S/C12H17N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,10,14,16H,5-7,13H2,(H,15,17)(H,18,19)/t10-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = SRSPQXBFDCGXIZ-JTQLQIEISA-N |Section2={{Chembox Properties | C=12 | H=17 | N=3 | O=4 | MeltingPtC = 203 | pKa = 3.4 |Section7={{Chembox Hazards | MainHazards = Toxic Agaritine is an aromatic hydrazine-derivative mycotoxin in mushroom species of the genus Agaricus. It is an α-aminoacid and a derivative of phenylhydrazine.

Occurrence

Agaritine is present as a natural mycotoxin in fresh samples of at least 24 species of the genera Agaricus, Leucoagaricus, and Macrolepiota. Mushrooms of these species are found around the world. These mushrooms grow in a wide range of habitats. Agaricus bisporus is cultivated in over 70 countries and on every continent except Antarctica. A. bisporus, also known as the portobello or common button mushroom, is of particular socio-economic importance in developed countries.

Agaritine content varies between individual mushrooms and across species. Agaritine content (% fresh weight) in raw Agaricus bisporus, for example, ranges from 0.033% to 0.173%, with an average of 0.088%. The highest amount of agaritine is found in the cap and gills of the fruiting body, and the lowest in the stem.

Production

Agaritine occurs naturally in mushrooms and can be extracted from cultivated Agaricus bisporus mushrooms with water or methanol.

Figure 2. Proposed biosynthesis of agaritine. --

Total industrial syntheses of agaritine have been completed, with an 83% yield, and the overall yield of 33%.

Potential for toxicity

Although recognized as an experimental carcinogen when used in high laboratory doses, there is inadequate evidence to classify Agaritine as carcinogenic to humans in amounts ingested from consuming mushrooms.

References

References

  1. (24 July 2021). "Agaritine". PubChem, US National Library of Medicine.
  2. (2009). "Agaritine content of 53 ''Agaricus'' species collected from nature". Food Additives & Contaminants: Part A.
  3. (December 2013). "The complete book of mushrooms : over 1,000 species and varieties of American, European, and Asiatic mushrooms". Crown Publishers.
  4. (December 2013). ["The Biology and cultivation of edible mushrooms"](http://www.sciencedirect.com/science/book/9780121680503}}{{page needed). Academic Press.
  5. (1982). "Agaritine Content of Fresh and Processed Mushrooms [''Agaricus bisporus'' (Lange) Imbach]". Journal of Food Science.
  6. (1982). "Occurrence, stability and decomposition of ''β''-''n''[''γ''-l( + )-glutamyl]-4-hydroxymethylphenylhydrazine (agaritine) from the mushroom ''Agaricus bisporus''". Food and Chemical Toxicology.
  7. (2002). "Influence of storage and household processing on the agaritine content of the cultivated Agaricus mushroom". Food Additives and Contaminants.
  8. (1987). "Novel Synthesis of Agaritine, a 4-Hydrazinobenzyl-Alcohol Derivative Occurring in Agaricaceae". Helvetica Chimica Acta.

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mycotoxinshydrazideshydroxymethyl-compoundsalpha-amino-acidsamino-acid-derivatives