Complexation of cholesterol with β-cyclodextrin derivatives: A combined theoretical and experimental study

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This study aimed to compare differences in interactions between cholesterol and β- cyclodextrin and its derivatives for selecting a suitable β-cyclodextrin derivative to efficiently remove cholesterol from high-melting-point foods. First, the formation of cholesterol/β-cyclodextrin derivative complexes was investigated using Fourier transform infrared spectroscopy and thermogravimetric analysis. Secondly, the conformations of β-cyclodextrin derivatives were determined from experimental and calculated 1H NMR spectra, and the weak interactions between cholesterol and β-cyclodextrin derivatives were studied by computational approach. Cholesterol/hydroxypropyl-β-cyclodextrin complex had the lowest complexation energy. Besides, two moderate hydrogen bonds were formed between cholesterol and hydroxypropyl-β-cyclodextrin and between cholesterol and sulfobutyl ether-β-cyclodextrin, while one weak hydrogen bond was formed between cholesterol and methyl-β-cyclodextrin. Finally, the efficiency of cholesterol removal by hydroxypropyl-β-cyclodextrin was 5.47% higher than that by β-cyclodextrin at their optimal temperature. This work provided a theoretical basis for selecting a competent adsorbent to effectively remove cholesterol from high-melting-point foods.

Effect of temperature on cholesterol removal from beef tallow using HP-β-CD and β-CD

The efficiency of HP-β-CD was significantly higher than that of β-CD at higher temperatures (50−60 °C), which was probably ascribed to the stronger interactions between cholesterol and HP-β-CD. An increase in cholesterol removal efficiency at high temperature which is higher than the melting point of beef tallow will facilitate cholesterol removal by HP-β-CD in large scale industrial applications.

Jingang He, Yunxiang Dai, Jinfeng Zhong, Xiong Liu, Xiaoli Qin (2024) Difference in the complexation of cholesterol with β-cyclodextrin derivatives: A combined theoretical and experimental study. Food Chemistry 435, 137459.

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