Agaritine is an aromatic hydrazine-derivative

mycotoxin A mycotoxin (from the Greek μύκης , "fungus" and τοξίνη , "toxin") is a toxic secondary metabolite produced by organisms of kingdom Fungi and is capable of causing disease and death in both humans and other animals. The term 'mycotoxin' ...

mushroom A mushroom or toadstool is the fleshy, spore-bearing fruiting body of a fungus, typically produced above ground, on soil, or on its food source. ''Toadstool'' generally denotes one poisonous to humans. The standard for the name "mushroom" is ...

species of the genus ''

Agaricus ''Agaricus'' is a genus of mushrooms containing both edible and poisonous species, with over 400 members worldwide and possibly again as many disputed or newly-discovered species. The genus includes the common ("button") mushroom ('' Agaricus bi ...

''. It is an α-aminoacid and a derivative of

phenylhydrazine Phenylhydrazine is the chemical compound with the formula . It is often abbreviated as . It is also found in edible mushrooms. Properties Phenylhydrazine forms monoclinic prisms that melt to an oil around room temperature which may turn yellow ...

Occurrence

Agaritine is present as a natural phytochemical in fresh samples of at least 24 species of the genera ''

'', '' Leucoagaricus'', and ''

Macrolepiota ''Macrolepiota'' is a genus of white spored, gilled mushrooms of the family Agaricaceae. The best-known member is the parasol mushroom (''M. procera''). The widespread genus contains about 40 species. Taxonomy ''Macrolepiota'' was circums ...

''. Mushrooms of these species are found around the world. 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. ''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. 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. It has also been shown to decompose readily upon cooking (up to 90% reduction) as well as upon freezing (up to 75% reduction).

Toxicology

Studies of the potential toxicity of agaritine in humans are absent. In high amounts, it is used experimentally as a

carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...

. Agaritine is broken down by enzymes in animal kidneys into the toxic metabolites 4-(hydroxymethyl)phenylhydrazine and 4-(hydroxymethyl)benzenediazonium ions.

Biosynthesis

Agaritine is synthesized in the vegetative mycelium and then translocated into the fruiting body.

Industry

Extraction of agaritine from mushroom waste is conducted with water or methanol, and isolation from the extract is conducted by various methods. Total industrial syntheses of agaritine have been completed, with an 83% yield, and the overall yield of 33%.

References

{{Hydrazines Mycotoxins Hydrazides Primary alcohols Amino acid derivatives

Occurrence

Toxicology

Biosynthesis

Industry

See also

References