The Luteolinidin and Petunidin 3- O-Glucoside: A Competitive Inhibitor of Tyrosinase

Molecules. 2022 Sep 4;27(17):5703. doi: 10.3390/molecules27175703.

Abstract

The enzyme tyrosinase plays a key role in the early stages of melanin biosynthesis. This study evaluated the inhibitory activity of anthocyanidin (1) and anthocyanins (2-6) on the catalytic reaction. Of the six derivatives examined, 1-3 showed inhibitory activity with IC50 values of 3.7 ± 0.1, 10.3 ± 1.0, and 41.3 ± 3.2 μM, respectively. Based on enzyme kinetics, 1-3 were confirmed to be competitive inhibitors with Ki values of 2.8, 9.0, and 51.9 μM, respectively. Molecular docking analysis revealed the formation of a binary encounter complex between 1-3 and the tyrosinase catalytic site. Luteolinidin (1) and petunidin 3-O-glucoside (2) may serve as tyrosinase inhibitors to block melanin production.

Keywords: anthocyanins; competitive inhibitor; melanin; molecular docking; tyrosinase.

MeSH terms

  • Agaricales*
  • Anthocyanins / pharmacology
  • Enzyme Inhibitors / pharmacology
  • Glucosides / pharmacology
  • Kinetics
  • Melanins
  • Molecular Docking Simulation
  • Molecular Structure
  • Monophenol Monooxygenase*

Substances

  • Anthocyanins
  • Enzyme Inhibitors
  • Glucosides
  • Melanins
  • Monophenol Monooxygenase
  • luteolinidin
  • petunidin