Conjugates of 1,3‐ and 1,2‐Acylglycerols with Stigmasterol: Synthesis, NMR Characterization, and Impact on Lipid Bilayers

Abstract

The main aim of research was synthesis and spectroscopic characterization of new conjugates in which stigmasterol was linked via carbonate or succinyl linker with 1,3-and 1,2acylglycerols of palmitic and oleic acid. Acylglycerols containing stigmasterol residue at internal position have been synthesized from 2-benzyloxypropane-1,3-diol or dihydroxyacetone. Their asymmetric counterparts containing stigmasterol residue attached to sn-3 position have been obtained from (S)-solketal. Eight synthesized conjugates were used to create the liposomes as nanocarriers of phytosterols to increase their stability and protect them from degradation during thermal-oxidative treat-ments. Fluorimetric and ATR-FTIR methods were used to determine the impact of synthesized conjugates on the physicochemical properties of the lipid bilayer. The results indicate that conjugates with palmitic acid are better candidates for use as the potential stigmasterol nanocarriers compared to those with oleic acid because they increase the stiffness of the lipid bilayer and temperature of the main phase transition. The obtained results are the first step in designing of stigmasterol-enriched liposomal carriers with higher thermooxidative stability for their potential use in the food industry.

The heating and storage of structured acylglycerols with succinyl-linked stigmasterol residue does not affect their chemical and biological negative changes

“…1,2-Dipalmitoyl-3-stigmasterylsuccinoyl-sn-glycerol (DP3SSt) and 1,2-dioleoyl-3stigmasterylsuccinoyl-sn-glycerol (DO3SSt) were synthesized from 1,2-O-isopropylidene-sn-glycerol. The details of synthetic protocols were described by Gładkowski et al 22 . In Fig.…”