Journal of the science of food and agriculture · 2025
Investigation of the effect of ethanol on the stability of black rice anthocyanin/cyclodextrin inclusion complexes in aqueous systems.
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Wang Yue, Yin Mingyu, Zhao Jingjing, Li Xiaolong, Cui Yuxing, Wang Yu
Аннотация
BACKGROUND: Black rice anthocyanins (BRA) possess antioxidant properties and can alleviate alcohol-induced liver injury but their stability in alcoholic beverages remains a challenge. This study investigated the effects of ethanol concentration on the structural stability of BRA/β-cyclodextrins (β-CDs) and their intermolecular interactions.
RESULTS: At low ethanol concentrations (<164.8 g kg-¹), hydrogen bonding between cyanidin-3-glucoside (C3G) and β-CD was enhanced whereas higher concentrations (>164.8 g kg-1) reduced hydrogen bond formation. The main interactions between β-CD and C3G were hydrogen bonds and van der Waals forces. In contrast, hydroxypropylation of β-CD (HP-β-CD) enlarged the cavity volume, weakening direct hydrogen bonding with C3G; van der Waals forces dominated the binding, and hydrogen bonds originated mainly from surrounding ethanol and water molecules.
CONCLUSION: Ethanol influenced the stability of the inclusion complexes by modulating the number of hydrogen bonds. High ethanol concentrations (>164.8 g kg-1) increased the structural rigidity of β-CD but reduced intramolecular hydrogen bonds within its cavity, leading to decreased stability. In contrast, the hydroxypropyl groups of HP-β-CD enlarged its cavity volume and height, allowing C3G to rely primarily on van der Waals interactions for stability. Consequently, HP-β-CD exhibited greater resistance to ethanol-induced destabilization. © 2025 Society of Chemical Industry.
RESULTS: At low ethanol concentrations (<164.8 g kg-¹), hydrogen bonding between cyanidin-3-glucoside (C3G) and β-CD was enhanced whereas higher concentrations (>164.8 g kg-1) reduced hydrogen bond formation. The main interactions between β-CD and C3G were hydrogen bonds and van der Waals forces. In contrast, hydroxypropylation of β-CD (HP-β-CD) enlarged the cavity volume, weakening direct hydrogen bonding with C3G; van der Waals forces dominated the binding, and hydrogen bonds originated mainly from surrounding ethanol and water molecules.
CONCLUSION: Ethanol influenced the stability of the inclusion complexes by modulating the number of hydrogen bonds. High ethanol concentrations (>164.8 g kg-1) increased the structural rigidity of β-CD but reduced intramolecular hydrogen bonds within its cavity, leading to decreased stability. In contrast, the hydroxypropyl groups of HP-β-CD enlarged its cavity volume and height, allowing C3G to rely primarily on van der Waals interactions for stability. Consequently, HP-β-CD exhibited greater resistance to ethanol-induced destabilization. © 2025 Society of Chemical Industry.