Isolation and Structure of Agaritine, a Gamma-glutamyl-substituted Arylhydrazine Derivative from Agaricaceae.

During the past several years, reports have appeared concerning the separation and characterization of a variety of newly recognized nonprotein amino acids of plant origin (2-6). A number of these substances have been identified as derivatives of glutamine in which substitution by residues other than those represented by the common a-amino acids has occurred at the amide nitrogen atom (6-13). In the present work, a new yglutamyl derivative of this type (herein referred to by the trivial name agaritine) has been detected in basidiomycetes of the family Agaricaceae. It has been isolated in a pure state from the press-juice of Agaricus bisporus, the mushroom of commerce in the United States. The properties and biological distribution of agaritine are reported in this paper, together with results from a variety of analytical and degradative procedures that have led to the characterization of this substance as b-N-(Y-L( +)-glutamyl)-p-hydroxymethylphenylhydrazine. The following paper (14) describes the purification, properties, and substrate specificity of an enzyme from Agaricus bisporus that is concerned with the cleavage and transfer of the y-n-glutamyl group of agaritine.