New Insights into pH-dependent Complex Formation between Lignosulfonates and Anthocyanins: Impact on Color and Oxidative Stability

J Agric Food Chem. 2024 Dec 4;72(48):26820-26831. doi: 10.1021/acs.jafc.4c05842. Epub 2024 Nov 20.

Abstract

Anthocyanins have limited application as natural colorants and antioxidants due to their color loss and instability under certain conditions. This research explores the formation of a complex between lignosulfonates (LS) and cyanidin-3-O-glucoside (C3G) using a multitechnique approach as well as the effect on C3G's red color, oxidative stability, and antioxidant activity in acidic mediums. All data revealed pH-dependent LS-C3G interactions. The thermodynamic parameters showed weak noncovalent interactions, mainly electrostatic interactions, hydrogen bonds, and hydrophobic effect, with a higher association constant determined at pH 3. Fourier-transform infrared spectroscopy and Zeta-potential experiments further corroborate evidence of these LS-C3G interactions. Fluorescence quenching and lifetime experiments revealed static and dynamic quenching at pH 1 and 3, respectively. UV-visible spectroscopy demonstrated a bathochromic shift upon complex formation and a hyperchromic effect at pH 3 and 4, as a consequence of the improved red color of C3G. Electrochemical results suggested that at pH 3 the LS enhances C3G stability by protecting its oxidizable moieties over time, as well as improving the antioxidant activity of the anthocyanin in the complex.

Keywords: UV–visible; fluorescence; hyperchromic effect; noncovalent interactions; redox; thermodynamic parameters.

MeSH terms

  • Anthocyanins* / chemistry
  • Antioxidants / chemistry
  • Color*
  • Glucosides / chemistry
  • Hydrogen-Ion Concentration
  • Lignin* / analogs & derivatives
  • Lignin* / chemistry
  • Oxidation-Reduction*
  • Spectroscopy, Fourier Transform Infrared
  • Thermodynamics

Substances

  • Anthocyanins
  • Lignin
  • lignosulfuric acid
  • Antioxidants
  • cyanidin-3-O-beta-glucopyranoside
  • Glucosides