Enzymatic Acylation of Flavonoids from Bamboo Leaves: Improved Lipophilicity and Antioxidant Activity for Oil-Based Foods

J Agric Food Chem. 2023 Mar 29;71(12):4817-4824. doi: 10.1021/acs.jafc.2c07673. Epub 2023 Mar 19.

Abstract

The goal of this study was to expand the applications of bamboo leaf flavonoids (BLFs) by improving their lipophilicity through enzymatic acylation with vinyl cinnamate. Characterization of the acylated BLFs using Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, high-resolution electrospray ionization mass spectrometry, electrospray ionization with tandem mass spectrometry, and 1H nuclear magnetic resonance spectroscopy indicated that acylation occurred at the C6-OH position of glucoside moieties. The highest degree of acylation (18.61%) was obtained by reacting BLFs with vinyl cinnamate (1:5, w/w) at 60 °C for 48 h. Acylation significantly improved the lipophilicity of BLFs and their capacity to inhibit lipid peroxidation, as evidenced by the reduced production of lipid hydroperoxides and malondialdehyde in rapeseed oil and rapeseed oil-in-water emulsions during storage at 37 °C for 15 days. The study findings provide important data that will enable the use of BLFs in lipid or lipophilic matrices, such as oil-based foods.

Keywords: acylation; antioxidant activity; bamboo leaf flavonoids; lipid solubility.

MeSH terms

  • Acylation
  • Antioxidants* / chemistry
  • Flavonoids* / chemistry
  • Plant Leaves / chemistry
  • Rapeseed Oil

Substances

  • Antioxidants
  • Flavonoids
  • Rapeseed Oil