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Agaritine

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; 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).

Production and manufacturing

Agaritine occurs naturally in mushrooms and can be extracted 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 when used in high laboratory doses, there is inadequate evidence to classify Agaritine as carcinogenic to humans in amounts ingested from consuming mushrooms.