Agaritine

Agaritine is an aromatic hydrazine-derivative mycotoxin in mushroom species of the genus Agaricus.[1] It is an α-aminoacid and a derivative of phenylhydrazine.

Agaritine
Stereo structural formula of agaritine ((2S)-2-amino)
Ball and stick model of agaritine ((2S)-2-amino)
Names
IUPAC name
2-[4-(Hydroxymethyl)phenyl]-glutamohydrazide
Other names
β-N-[γ-glutamyl]-4-hydroxymethylphenylhydrazine
N2-(γ-glutamyl)-4-hydroxymethylphenylhydrazine
Identifiers
3D model (JSmol)
Abbreviations AGT
757731
ChEBI
ChemSpider
KEGG
MeSH Agaritine
RTECS number
  • MA1284000
UNII
  • InChI=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 checkY
    Key: SRSPQXBFDCGXIZ-JTQLQIEISA-N checkY
  • 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
    Key: SRSPQXBFDCGXIZ-JTQLQIEIBZ
  • [O-]C(=O)[C@@H]([NH3+])CCC(=O)NNc1ccc(cc1)CO
Properties
C12H17N3O4
Molar mass 267.285 g·mol−1
Melting point 203 °C (397 °F; 476 K)
Acidity (pKa) 3.4
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Occurrence

Agaritine is present as a natural phytochemical in fresh samples of at least 24 species of the genera Agaricus, Leucoagaricus, and Macrolepiota.[1][2] Mushrooms of these species are found around the world.[3] These mushrooms grow in a wide range of habitats; indeed, one species alone, Agaricus bisporus, is cultivated in over 70 countries and on every continent except Antarctica.[4] A. bisporus, also known as the common button mushroom, is of particular socio-economic importance in developed countries.[4]

Agaritine content varies between individual mushrooms and across species.[2] Agaritine content (% fresh weight) in raw Agaricus bisporus, for example, ranges from 0.033% to 0.173%, with an average of 0.088%.[5] The highest amount of agaritine is found in the cap and gills of the fruiting body, and the lowest in the stem.[6] Agaritine oxidizes rapidly upon storage, however, and is totally degraded after 48 hours in aqueous solution with exposure to extraction with water or methanol and isolation from the extract by one of several methods.[7] It has also been shown to decompose readily upon cooking (up to 90% reduction) as well as upon freezing (up to 75% reduction).[8]

Production and manufacturing
(4) L-shikimic acid, the fully protonated conjugate acid of L-shikimate
(6) 4-hydroxybenzoic acid, also known as p-hydroxybenzoic acid

Agaritine occurs naturally in mushrooms and can be extracted from cultivated Agaricus bisporus mushrooms with water or methanol.[1]

Total industrial syntheses of agaritine have been completed, with an 83% yield, and the overall yield of 33%.[9]

Potential for toxicity

Although recognized as an experimental carcinogen when used in high laboratory doses, there is no evidence that agaritine is carcinogenic to humans in amounts ingested from consuming mushrooms.[1]

See also

References
  1. "Agaritine". PubChem, US National Library of Medicine. 24 July 2021. Retrieved 27 July 2021.
  2. Schulzová, V.; Hajslova, J.; Peroutka, R.; Hlavasek, J.; Gry, J.; Andersson, H.C. (2009). "Agaritine content of 53 Agaricus species collected from nature" (PDF). Food Additives & Contaminants: Part A. 26 (1): 82–93. doi:10.1080/02652030802039903. PMID 19680875. S2CID 427230.
  3. Rinaldi, Augusto; Tyndalo, Vassili; Maggiora, Laura Rosano (1974). The complete book of mushrooms : over 1,000 species and varieties of American, European, and Asiatic mushrooms. Crown Publishers. ISBN 978-0-517-51493-1.
  4. Hayes, W. A.; Chang, S. T. (1978). The Biology and cultivation of edible mushrooms. Academic Press. ISBN 978-0-12-168050-3.
  5. Liu, J.-W.; Beelman, R. B.; Lineback, D. R.; Speroni, J. J. (1982). "Agaritine Content of Fresh and Processed Mushrooms [Agaricus bisporus (Lange) Imbach]". Journal of Food Science. 47 (5): 1542–4. doi:10.1111/j.1365-2621.1982.tb04978.x.
  6. Ross, A.E.; Nagel, D.L.; Toth, B. (1982). "Occurrence, stability and decomposition of β-n[γ-l( + )-glutamyl]-4-hydroxymethylphenylhydrazine (agaritine) from the mushroom Agaricus bisporus". Food and Chemical Toxicology. 20 (6): 903–7. doi:10.1016/S0015-6264(82)80226-5. PMID 6131022.
  7. Hajšlová, J.; Hájková, L.; Schulzová, V.; Frandsen, H.; Gry, J.; Andersson, H. C. (2002). "Stability of agaritine - a natural toxicant ofAgaricusmushrooms". Food Additives and Contaminants. 19 (11): 1028–33. doi:10.1080/02652030210157691. PMID 12456273. S2CID 19357429.
  8. Schulzová, V.; Hajslová, J.; Peroutka, R.; Gry, J.; Andersson, H. C. (2002). "Influence of storage and household processing on the agaritine content of the cultivated Agaricus mushroom". Food Additives and Contaminants. 19 (9): 853–62. doi:10.1080/02652030210156340. PMID 12396396. S2CID 23953741.
  9. Datta, Subir; Hoesch, Lienhard (1987). "Novel Synthesis of Agaritine, a 4-Hydrazinobenzyl-Alcohol Derivative Occurring in Agaricaceae". Helvetica Chimica Acta. 70 (5): 1261–7. doi:10.1002/hlca.19870700505.
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