Cyrene™ as a tyrosinase inhibitor and anti-browning agent

Abstract

The tyrosinase pathway takes part in the enzymatic process of food browning and is primarily responsible for food spoilage - manifesting itself from a decrease in its nutritional value to a deterioration of taste, which consequently leads to a gradual loss of shelf life. Finding safe and bio-based tyrosinase inhibitors and anti-browning agents may be of great importance in agriculture and food industries. Herein, we showed that Cyrene™ exhibits tyrosinase inhibitory activity (IC₅₀: 268.2 µM), the 1.44 times higher than ascorbic acid (IC₅₀: 386.5 μM). Binding mode studies demonstrated that the carbonyl oxygen of Cyrene™ coordinates with both copper ions. Surprisingly, both hydroxyl groups of Cyrene gem-diol perform a monodentate binding mode with both copper ions, at similar distances. This fact suggests that both compounds could have a similar binding mode and, as consequence, similar biological activities in tyrosinase inhibition assays and anti-browning activities.

Keywords: Anti-browning agents; Cu-coordination; Cyrene; Dynamics simulations; Molecular docking; Tyrosinase inhibitor.