pH-Responsive Emulsions with β-Cyclodextrin/Vitamin E Assembled Shells for Controlled Delivery of Polyunsaturated Fatty Acids

J Agric Food Chem. 2019 Oct 30;67(43):11931-11941. doi: 10.1021/acs.jafc.9b04168. Epub 2019 Oct 18.

Abstract

Lipid-based delivery systems (LBDSs) are widely applied in pharmaceuticals and health care because of the increased bioavailability of lipophilic components when they are coadministered with high-fat meals. However, how to accurately control their in vivo release and stability is still challenging. Here, after introducing the simple esterification and coprecipitation, we created the dual-functional composite ODS-β-CD-VE by the coassembly of β-cyclodextrin (β-CD), octadecenyl succinic anhydride (ODSA), and vitamin E (VE). The resulting dual-functional particle presented a uniform sheetlike shape and nanometer size. In addition, its chemical structure was clarified in detail via nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FTIR), and X-ray diffraction (XRD). Benefiting from the antioxygenation of VE, lipid oxidation in the ODS-β-CD-VE-stabilized Pickering emulsion was effectively inhibited. Meanwhile, pH-induced protonation/deprotonation of carboxyl groups guaranteed that the emulsions kept steady at pH ≤4 but were unsteady under neutral conditions. In this way, the lipids contained in the emulsion were protected from gastric juice and then digested and accurately released as n-3 polyunsaturated fatty acids (PUFA) in the simulated intestine environment. This strategy sheds some light on the rational and efficient construction of LBDSs for nutrient supplements and even pharmaceuticals in a living digestive tract.

Keywords: antioxidation; digestion; pH response; vitamin E; β-CD.

MeSH terms

  • Delayed-Action Preparations / chemistry*
  • Delayed-Action Preparations / metabolism
  • Digestion
  • Emulsions / chemistry
  • Fatty Acids, Unsaturated / chemistry*
  • Fatty Acids, Unsaturated / metabolism
  • Gastrointestinal Tract / metabolism
  • Humans
  • Hydrogen-Ion Concentration
  • Models, Biological
  • Vitamin E / chemistry*
  • beta-Cyclodextrins / chemistry*

Substances

  • Delayed-Action Preparations
  • Emulsions
  • Fatty Acids, Unsaturated
  • beta-Cyclodextrins
  • Vitamin E