Agaritine is an aromatic
hydrazine
Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydraz ...
-derivative
mycotoxin in
mushroom
A mushroom or toadstool is the fleshy, spore-bearing Sporocarp (fungi), fruiting body of a fungus, typically produced above ground on soil or another food source. ''Toadstool'' generally refers to a poisonous mushroom.
The standard for the n ...
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 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.
Agaratine decomposes significantly between harvest and sale, and it has also been shown to decompose readily upon cooking (up to 90% reduction) as well as upon freezing (up to 75% reduction).
Production
Agaritine occurs naturally in mushrooms and can be
extract
An extract (essence) is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures or absolutes or dried and powdered.
The aromatic principles of ma ...
ed from cultivated ''Agaricus bisporus'' mushrooms with water or methanol.
[
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
A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...
when used in high laboratory doses, there is inadequate evidence to classify Agaritine as carcinogenic to humans in amounts ingested from consuming mushrooms.[
]
See also
* Agaritine gamma-glutamyltransferase
* Gyromitrin
References
{{Hydrazines
Mycotoxins
Hydrazides
Hydroxymethyl compounds
Alpha-Amino acids
Amino acid derivatives