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

被引：4

作者：

Gladkowski, Witold ^{[1
]}

Chojnacka, Anna ^{[1
]}

Wloch, Aleksandra ^{[2
]}

Pruchnik, Hanna ^{[2
]}

Grudniewska, Aleksandra ^{[1
]}

Dunal, Anna ^{[1
]}

Dudek, Anita ^{[2
]}

Maciejewska, Gabriela ^{[3
]}

Rudzinska, Magdalena ^{[4
]}

机构：

[1] Wroclaw Univ Environm & Life Sci, Dept Food Chem & Biocatalysis, Norwida 25, PL-50375 Wroclaw, Poland

[2] Wroclaw Univ Environm & Life Sci, Dept Phys & Biophys, Norwida 25, PL-50375 Wroclaw, Poland

[3] Wroclaw Univ Sci & Technol, Fac Chem, Norwida 4-6, PL-50373 Wroclaw, Poland

[4] Poznan Univ Life Sci, Fac Food Sci & Nutr, Wojska Polskiego 28, PL-60637 Poznan, Poland

来源：

CHEMPLUSCHEM | 2023年 / 88卷 / 05期

关键词：

acylglycerols; esterification; lipids; liposomes; phytosterols; CHEMOENZYMATIC SYNTHESIS; ENZYMATIC-SYNTHESIS; BETA-SITOSTEROL; ESTERS; PHYTOSTEROLS; BENZYL; MODEL; TRIACYLGLYCEROLS; TRIGLYCERIDES; CHOLESTEROL;

D O I：

10.1002/cplu.202300161

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 1,2-acylglycerols 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 treatments. 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 thermo-oxidative stability for their potential use in the food industry.

引用

页数：13