Synthesis of 4'-thiosemicarbazonegriseofulvin and its effects on the control of enzymatic browning and postharvest disease of fruits.

ABSTRACT

4'-Thiosemicarbazonegriseofulvin, a new thiosemicarbazide derivative of griseofulvin, was synthesized and evaluated for its potential in the control of enzymatic browning and postharvest disease of fruits. Browning on fruits is mainly due to the enzymatic oxidation of phenolic compounds catalyzed by tyrosinase. 4'-Thiosemicarbazonegriseofulvin could effectively inhibit the activity of tyrosinase, and its 50% inhibitory concentration (IC(50)) against tyrosinase was determined to be 37.8 µM. It was a reversible and noncompetitive inhibitor of tyrosinase, and its inhibition constant (K(I)) was determined to be 38.42 µM. The antifungal activity of 4'-thiosemicarbazonegriseofulvin was studied against four fungi (Fusarium oxysporum, Fusarium moniliforme, Fusarium solani, and Colletotrichum truncatum) that often cause postharvest diseases of fruits. The results showed that 4'-thiosemicarbazonegriseofulvin could also strongly inhibit the mycelial growth of the four target fungi; the 50% lethal concentration (LC(50)) values were 5.4, 7.0, 15.3, and 1.5 mM, respectively.