Homogentisic Acid and Gentisic Acid Biosynthesized Pyomelanin Mimics: Structural Characterization and Antioxidant Activity

Int J Mol Sci. 2021 Feb 9;22(4):1739. doi: 10.3390/ijms22041739.

Abstract

Pyomelanin mimics from homogentisic acid (HGA) and gentisic acid (GA) were biosynthesized by the oxidative enzyme T. versicolor laccase at physiological pH to obtain water soluble melanins. The pigments show brown-black color, broad band visible light absorption, a persistent paramagnetism and high antioxidant activity. The EPR approach shows that at least two different radical species are present in both cases, contributing to the paramagnetism of the samples. This achievement can also shed light on the composition of the ochronotic pigment in the Alkaptonuria disease. On the other hand, these soluble pyomelanin mimics, sharing physico-chemical properties with eumelanin, can represent a suitable alternative to replace the insoluble melanin pigment in biotechnological applications.

Keywords: EPR; antioxidant activity; gentisic acid; homogentisic acid; laccase; pyomelanin mimics; radical species.

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Antioxidants / metabolism
  • Antioxidants / pharmacology*
  • Biotechnology / methods
  • Fungal Proteins / metabolism
  • Gentisates / chemistry
  • Gentisates / isolation & purification
  • Gentisates / metabolism
  • Gentisates / pharmacology*
  • Homogentisic Acid / chemistry
  • Homogentisic Acid / isolation & purification
  • Homogentisic Acid / metabolism
  • Homogentisic Acid / pharmacology*
  • Laccase / metabolism
  • Melanins / chemistry
  • Polyporaceae / enzymology

Substances

  • Antioxidants
  • Fungal Proteins
  • Gentisates
  • Melanins
  • pyomelanin
  • Laccase
  • Homogentisic Acid
  • 2,5-dihydroxybenzoic acid

Supplementary concepts

  • Trametes versicolor