Preparation and Physicochemical Characterization of Gelatin-Aldehyde Derivatives

Molecules. 2022 Oct 18;27(20):7003. doi: 10.3390/molecules27207003.

Abstract

The present study aimed at preparing novel free-radical scavenging and water-soluble compounds derived from gelatin. Specifically, gelatin−syringaldehyde, gelatin−anisaldehyde, and gelatin−vanillin were synthesized and thoroughly studied for their physicochemical properties. In particular, the compounds were characterized by UV-Vis spectroscopy, Fourier-transform infrared spectroscopy, and scanning electron microscopy. Notably, as demonstrated by thermogravimetry and differential scanning calorimetry, all three derivatives exhibited higher thermal stability than gelatin itself. Free-radical scavenging activities of the examined compounds were explored by (i) a standard spectrophotometric ABTS assay and (ii) an assay of oxidative degradation of hyaluronic acid monitored by rotational viscometry. We found that gelatin and gelatin−syringaldehyde demonstrated the highest efficacy in scavenging •OH radicals, whereas gelatin−anisaldehyde was the least effective. The efficacy of scavenging alkyloxy- and alkylperoxy-type free radicals via hydrogen-atom-transferring property was in the following order: gelatin > gelatin−vanillin > gelatin−syringaldehyde > gelatin−anisaldehyde. Electron-donor properties determined using the ABTS assay revealed the following order in one-electron reduction of ABTS•+: gelatin > gelatin−anisaldehyde > gelatin−vanillin > gelatin−syringaldehyde.

Keywords: FT-IR spectroscopy; UV-Vis spectrometry; gelatin functionalization; rotational viscometry; scanning electron microscopy; thermoanalytical methods.

MeSH terms

  • Aldehydes
  • Free Radicals
  • Gelatin* / chemistry
  • Hyaluronic Acid*
  • Hydrogen
  • Spectroscopy, Fourier Transform Infrared
  • Water / chemistry

Substances

  • vanillin
  • syringaldehyde
  • Gelatin
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • 4-anisaldehyde
  • Hyaluronic Acid
  • Aldehydes
  • Free Radicals
  • Water
  • Hydrogen

Grants and funding

This research was funded by VEGA 2/0019/19 and VEGA 2/0166/20 provided by Scientific grant agency of The Ministry of Education, Science, Research and Sport of the Slovak Republic in Bratislava, Slovakia.