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Effect directed synthesis of a new tyrosinase inhibitor with anti-browning activity

Food Chem. 2021 Mar 30;341(Pt 1):128232. doi: 10.1016/j.foodchem.2020.128232. Epub 2020 Sep 28.

Abstract

The inhibition of enzymatic browning is an attractive target to elevate the quality of foods. The objective of this work is to describe a novel platform for the discovery of tyrosinase inhibitors, based on (a) one-pot preparation of a library of thiosemicarbazide compounds, (b) biological evaluation using tyrosinase TLC bioautography, (c) inhibitor identification via mass spectrometry coupled to bioautography. During these proof-of-concept experiments, the approach led to the straightforward identification of a new thiosemicarbazone with improved tyrosinase inhibition properties and fresh-cut apple slices antibrowning effect when compared to kojic acid. In conclusion, the platform represents an interesting strategy for the discovery of this type of inhibitors.

Keywords: Bioautography; Browning; Inhibition; Thiosemicarbazone; Tyrosinase.

MeSH terms

  • Chemistry Techniques, Synthetic
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Maillard Reaction / drug effects*
  • Malus / chemistry
  • Malus / drug effects
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Thiosemicarbazones / chemical synthesis
  • Thiosemicarbazones / pharmacology

Substances

  • Enzyme Inhibitors
  • Thiosemicarbazones
  • Monophenol Monooxygenase