Enhanced antibacterial, antioxidant and anticancer activity of caffeic acid by simple acid-base complexation with spermine/spermidine

Nat Prod Res. 2022 Dec;36(24):6453-6458. doi: 10.1080/14786419.2022.2038597. Epub 2022 Feb 10.

Abstract

Caffeic acid (CA) is a naturally occurring plant-derived polyphenol possessing diverse biological properties. However, the poor water-solubility of CA restricts its widespread applications. On the other hand, biogenic amines such as spermine and spermidine are natural constituents in eukaryotes. In this work, we present water-soluble complexes of CA with spermine and spermidine by exploiting the acid-base interaction. Four different compositions have been prepared by varying the CA to amine ratios, whose chemical structures have been probed in detail using Fourier-transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance (NMR) studies that have revealed the acid-base interaction between the constituent precursors. The obtained acid-base complexes at their native pH values have shown enhanced antibacterial and antioxidant activities than pristine CA. Further, the CA-polyamine complexes have shown high anticancer performances in the concentration range that is compatible with the normal cell lines.

Keywords: Caffeic acid; anticancer; antimicrobial; antioxidant; phytochemical; spermidine; spermine.

MeSH terms

  • Anti-Bacterial Agents / pharmacology
  • Antioxidants / pharmacology
  • Spectroscopy, Fourier Transform Infrared
  • Spermidine* / chemistry
  • Spermidine* / metabolism
  • Spermidine* / pharmacology
  • Spermine* / chemistry
  • Spermine* / metabolism
  • Spermine* / pharmacology
  • Water

Substances

  • Spermine
  • Spermidine
  • caffeic acid
  • Antioxidants
  • Water
  • Anti-Bacterial Agents