Imidazole‐modified C₆‐chitosan derivatives used to extract β‐sitosterol from edible oil samples with a microwave‐assisted solid phase extraction method

Abstract

β‐Sitosterol is a major bioactive constituent in plants with potent anticancer effects against many human cancer cells, but its bioavailability and therapeutic efficacy are limited by its poor solubility in water. In this study, C6‐imidazole chitosan, C6‐1‐methylimidazole chitosan, C6‐1‐ethylimidazole chitosan, C6‐1‐vinylimidazole chitosan, C6‐1‐allylimidazole chitosan, and C6‐1‐butylimidazole chitosan were prepared to extract β‐sitosterol from edible oil samples via ultrasonic‐assisted solid liquid extraction. The structures and properties of the newly synthesized products were characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, and elemental analysis. The extraction abilities of the derivatives were tested in the experiment with high‐performance liquid chromatography (limit of detection 0.21 μg/g and limit of quantification 0.67 μg/g), and the % relative standard deviation (<3.25%) and recovery values of the prepared chitosan derivatives toward β‐sitosterol (average: 100.20%) were acceptable. The spiked interday and intraday recoveries of β‐sitosterol were 102.60 ± 2.78 and 103.90 ± 3.04%, respectively. The actual amounts of β‐sitosterol extracted from three real samples using C6‐imidazole chitosan according to the solid phase extraction method were 3302.40, 901.70, and 2045.60 mg/kg for corn oil, olive oil, and pea oil, respectively.

Anticancer activity and other biomedical properties of β‐sitosterol: Bridging phytochemistry and current pharmacological evidence for future translational approaches

“…Therefore, structural modifications of β-sitosterol monomer substantially improved the drug targeting, solubility, and bioavailability (Andima et al, 2018;Takayasu et al, 2020). The advantageous and deleterious effects of these oxygenated phytosterols on well-being of humans remain contentious (Takayasu et al, 2020), and their low solubility in water also restricts their bioavailability and curative effect (Andima et al, 2018;Dai & Row, 2021). As a result, researchers have recognized the importance of modifying the structures or altering the dosage forms of these compounds in order to enhance drug bioavailability, solubility, release, and targeting (Xiong et al, 2016) of β-sitosterol to improve its bioavailability.…”

Molecular Mechanism of β-Sitosterol and its Derivatives in Tumor Progression

“…Although SIT has significant anti-tumor activity, natural phytosterols undergo auto-oxidation or enzymatic oxidation stimulated by ROS (such as ozone), O 2 , light, heat, or enzymes ( 65 ), resulting in the formation of phytosterol oxidation products (POPs) or oxygenated phytosterols. The beneficial and detrimental side effects of these compounds on human health remain controversial ( 5 ), and their poor solubility in water limits their bioavailability and therapeutic effect ( 66 , 67 ). Therefore, scientists believe that modifying the structure or changing the dosage forms of monomeric compounds is necessary to improve drug release, solubility, targeting, and bioavailability ( 68 ).…”