A Novel Inhibitor Against Mushroom Tyrosinase with a Double Action Mode and Its Application in Controlling the Browning of Potato

Abstract

In order to search for a new method for the antibrowning of food products, a novel hydroxypyridinone (HPO) derivative with a formyl group was evaluated for its anti-tyrosinase property. This compound was found to exhibit potent tyrosinase inhibition on the monophenolase activity of mushroom tyrosinase with an IC 50 value of 1.33 μM, indicating that this HPO derivative was 12-fold stronger than kojic acid (IC 50 15.89 μM). This molecule can inhibit tyrosinase via two action modes, namely copper reduction and chelation, and the formation of a Schiff's base with the amino group at the active site of the enzyme. A synergistic effect of these two action modes to enhance the inhibitory activity was observed. This compound was also investigated for the inhibitory effect on diphenolase activity of mushroom; the inhibitory mechanism was found to be reversible and of competitive-uncompetitive mixed-type inhibition. This hydroxypyridinone was demonstrated to effectively control the browning of vegetable products.

Functionality study of chalcone-hydroxypyridinone hybrids as tyrosinase inhibitors and influence on anti-tyrosinase activity

“…In addition, the reaction process catalysed by the diphenolase activity of tyrosinase had no lag time. This result is in agreement with those of previous reports 18,19 .…”

“…Kojic acid, a secondary metabolite produced by Aspergillus and Penicillium moulds, provides a promising starting point for the synthesis of new tyrosinase inhibitors; the a-hydroxy ketone functionality plays an important role in tyrosinase inhibition 14,15 . Based on previous results, relating to hydroxypyridinones [16][17][18][19] , we have functionalised kojic acid to form new derivatives in attempt to identify more potent tyrosinase inhibitors.…”

Enzymatic characteristics of polyphenoloxidase from shrimp (Penaeus vannamei) and its inhibition by a novel hydroxypyridinone derivative

“…The determination of copper(II) reducing capacity of hydroxypyridinone derivative 1 was referred to the previous reports (Chen et al, 2017). A cupric sulphate solution (0.5 mL, 0.4 mM) was mixed with compound 1 solution (1 mL, 0-1.5 mM (0-441 lg/mL)).…”

Inhibition of Enzymatic Browning by Onion (Allium cepa L.): Investigation on Inhibitory Mechanism and Identification of Active Compounds

“…24 Some PPO inhibitor demonstrating competitive mechanism could serve as metal chelator, non-metabolite analog, and/or derivate from the real substrate. 25 The molecular structure of cyanidin belonged to polyphenolic compounds is responsible for metalchelating properties, i.e. ortho-hydroxy groups in the B-ring, 2,3-double bond in the conjugation, and 4-oxo-function in the C-ring.…”