Agaritine mma-L(+)-glutamyl)-4-hydroxymethylphenylhydrazine] was isola
ted and purified from mushrooms (Agaricus bisporus). This paper report
s for the first time the inhibition of the monophenolase and diphenola
se activities of mushroom polyphenol oxidase by this abundant and char
acteristic compound from the Agaricus genus. Agaritine showed uncompet
itive inhibition (K-I = 2.3 mM) and partial competitive inhibition (K-
I = 0.13 mM; alpha = 2.5) when L-DOPA and L-tyrosine were assayed, res
pectively. In addition to the ability of agaritine to inhibit the enzy
me per se, this compound was capable of removing the enzymatically gen
erated o-quinones in the assay. To solve this problem, the inhibition
was characterized by using 3-methyl-2-benzothiazolinone hydrazone as n
ucleophile reagent to form a stable nucleophile-quinone adduct that co
uld not be attacked by agaritine. The inhibition of mushroom polypheno
l oxidase by other inhibitors is compared to the inhibition by agariti
ne. Moreover, a possible role for agaritine in the browning of mushroo
ms is discussed.