Posted by This study [1] 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 from beef tallow by hydroxypropyl-β-cyclodextrin was 5.47% higher than that by β-cyclodextrin at their optimal temperature (50+60 oC). This work provided a theoretical basis for selecting a competent adsorbent to effectively remove cholesterol from high-melting-point foods.
These data are not in agreement with those from earlier findings on the efficiency of β-cyclodextrin and its derivatives in the removal of cholesterol from liposomes and human cells. For instance MeCD reduces the integrity of liposomes via cholesterol removal better than HPBCD [2]. Piel et al. found that the cholesterol solubilizing effect follows the order of TRIMEB > RAMEB >DIMEB > CRYSMEB > HPBCD, so all the methylated derivatives overcome HPBCD [3]. Similar results were obtained by Davidson et al. [4]: MeBCD > HPBCD > SBECD.
[1] 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. https://doi.org/10.1016/j.foodchem.2023.137459.
[2] Panayiota Hatzi, Spyridon Mourtas, Pavlos G. Klepetsanis, Sophia G. Antimisiaris (2007) Integrity of liposomes in presence of cyclodextrins: Effect of liposome type and lipid composition, International Journal of Pharmaceutics 333, 167-176. https://doi.org/10.1016/j.ijpharm.2006.09.059.
[3] G. Piel, M. Piette, V. Barillaro, D. Castagne, B. Evrard, L. Delattre (2007) Study of the relationship between lipid binding properties of cyclodextrins and their effect on the integrity of liposomes. International Journal of Pharmaceutics 338, 35-42. https://doi.org/10.1016/j.ijpharm.2007.01.015.
[4] Cristin D. Davidson, Yonatan I. Fishman, István Puskás, Julianna Szemán, Tamás Sohajda, Leslie A. McCauliff, Jakub Sikora, Judith Storch, Marie T. Vanier, Lajos Szente, Steven U. Walkley, Kostantin Dobrenis (2016) Efficacy and ototoxicity of different cyclodextrins in Niemann–Pick C disease. Ann Clin Transl Neurol. 3(5):366-80. https://doi.org/10.1002/acn3.306