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芦丁与β-环糊精包合物的抗氧化活性：实验与量子化学研究

Antioxidant activity of an inclusion complex between rutin and β-cyclodextrin: experimental and quantum chemical studies.

作者信息

Pham Thi Lan, Ha Nguyen Thi Thu, Nguyen Tuan Anh, Le-Deygen Irina, Hanh Le Thi My, Vu Xuan Minh, Le Hai Khoa, Van Cuong Bui, Usacheva T R, Mai Thanh Tung, Tran Dai Lam

机构信息

Institute for Tropical Technology, Vietnam Academy of Science and Technology 18 Hoang Quoc Viet, Cau Giay Hanoi Vietnam

Graduate University of Science and Technology, Vietnam Academy of Science and Technology 18 Hoang Quoc Viet, Cau Giay Hanoi Vietnam.

出版信息

RSC Adv. 2024 Jun 7;14(26):18330-18342. doi: 10.1039/d4ra02307b. eCollection 2024 Jun 6.

DOI:10.1039/d4ra02307b
PMID:38854829
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11157499/
Abstract

This study aims to synthesize a guest-host complex derived from rutin (Rut) and β-cyclodextrin (β-CD) (denoted as [Rut⊂β-CD]). The obtained substance was characterized by the FT-IR and DSC methods, signifying the formation of an inclusion complex between Rut and β-CD. Complex formation increased the antioxidant activity of rutin corresponding to the decrease of EC values from 1.547 × 10 mol L to 1.227 × 10 mol L according to the DPPH free radical scavenging test. The rutin-β-CD interaction energies were calculated in the vacuum and various solvents (, water, ethanol, and dimethylsulfoxide) utilizing an accurate and broadly parametrized self-consistent tight-binding quantum chemical method (GFN2-xTB). The calculation results reveal the influence of solvent on the structural formation of the rutin-β-CD complex. In both the vacuum and aqueous solution, rutin can enter into the small-sized empty cavity of β-CD, albeit through different terminals, resulting in distinct preferential structures. The presence of organic solvents appears to reduce the interaction between rutin and β-CD, with the interaction strength following the order: water > ethanol > dimethyl sulfoxide.

摘要

本研究旨在合成一种由芦丁（Rut）和β-环糊精（β-CD）衍生的客体-主体复合物（记为[Rut⊂β-CD]）。通过傅里叶变换红外光谱（FT-IR）和差示扫描量热法（DSC）对所得物质进行了表征，表明Rut与β-CD之间形成了包合物。根据二苯基苦味酰基自由基（DPPH）清除试验，复合物的形成提高了芦丁的抗氧化活性，相应地，EC值从1.547×10 mol/L降至1.227×10 mol/L。利用精确且参数化广泛的自洽紧束缚量子化学方法（GFN2-xTB），在真空和各种溶剂（水、乙醇和二甲基亚砜）中计算了芦丁-β-CD的相互作用能。计算结果揭示了溶剂对芦丁-β-CD复合物结构形成的影响。在真空和水溶液中，芦丁均可进入β-CD的小尺寸空穴，尽管通过不同的末端，从而导致不同的优先结构。有机溶剂的存在似乎会降低芦丁与β-CD之间的相互作用，相互作用强度顺序为：水＞乙醇＞二甲基亚砜。

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