食品级杂偶联双黄酮的合成及抗氧化活性的三维定量构效关系(QSAR)建模。

IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY
Hongling Zheng, Xin Yang, Qiuyu Zhang, Joanne Yi Hui Toy, Dejian Huang
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引用次数: 0

摘要

生物类黄酮是一种独特的膳食多酚类化合物,以其多样的生物活性而闻名。尽管有这些好处,这些生物类黄酮在很大程度上仍未得到充分开发,因为它们的天然可用性有限,合成条件苛刻,这限制了在功能食品和营养保健品中的广泛研究和应用。为了解决这一空白,我们利用本小组先前报道的自由基-亲核偶联反应合成了一个罕见的生物类黄酮文库。在室温弱碱性水条件下进行食品级偶联反应,从11个单体中分离出28个异偶联双黄酮,分别为3′,4′-二羟黄酮、5,3′,4′-三羟黄酮、6,3′,4′-三羟黄酮、7,3′,4′-三羟黄酮、薯蓣皂苷、菊花素、阿卡乙素、染料木素、生物茶豆素A和木犀草素。用核磁共振波谱(NMR)和高分辨率质谱(HRMS)对二聚体的结构进行了表征。此外,我们利用DPPH(2,2-二苯基-1-吡啶酰肼)自由基清除实验评估了这些双黄酮的抗氧化潜力,在28个合成的二聚体中,DPPH值在0.75至1.82 mM的Trolox/mM样品之间。此外,还进行了三维定量构效关系(3D-QSAR)分析,以确定与抗氧化活性增强相关的结构特征。偏最小二乘(PLS)回归QSAR模型可接受,r2 = 0.936, q2 = 0.869。此外,还测定了平均局域电离能(ALIE)、静电势(ESP)、福井指数(F-)和电子密度(ED),以确定能够提供电子来中和活性氧的关键结构片段。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Food Grade Synthesis of Hetero-Coupled Biflavones and 3D-Quantitative Structure-Activity Relationship (QSAR) Modeling of Antioxidant Activity.

Biflavonoids are a unique subclass of dietary polyphenolic compounds known for their diverse bioactivities. Despite these benefits, these biflavonoids remain largely underexplored due to their limited natural availability and harsh conditions required for their synthesis, which restricts broader research and application in functional foods and nutraceuticals. To address this gap, we synthesized a library of rare biflavonoids using a radical-nucleophile coupling reaction previously reported by our group. The food grade coupling reaction under weakly alkaline water at room temperature led to isolation of 28 heterocoupled biflavones from 11 monomers, namely 3',4'-dihydroxyflavone, 5,3',4'-trihydroxyflavone, 6,3',4'-trihydroxyflavone, 7,3',4'-trihydroxyflavone, diosmetin, chrysin, acacetin, genistein, biochanin A, and wogonin. The structures of the dimers are characterized by nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectroscopy (HRMS). In addition, we evaluated the antioxidant potential of these biflavones using a DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging assay and the DPPH value ranges between 0.75 to 1.82 mM of Trolox/mM of sample across the 28 synthesized dimers. Additionally, a three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis was conducted to identify structural features associated with enhanced antioxidant activity. The partial least squares (PLS) regression QSAR model showed acceptable r2 = 0.936 and q2 = 0.869. Additionally, the average local ionization energy (ALIE), electrostatic potential (ESP), Fukui index (F-), and electron density (ED) were determined to identify the key structural moiety that was capable of donating electrons to neutralize reactive oxygen species.

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来源期刊
Antioxidants
Antioxidants Biochemistry, Genetics and Molecular Biology-Physiology
CiteScore
10.60
自引率
11.40%
发文量
2123
审稿时长
16.3 days
期刊介绍: Antioxidants (ISSN 2076-3921), provides an advanced forum for studies related to the science and technology of antioxidants. It publishes research papers, reviews and communications. Our aim is to encourage scientists to publish their experimental and theoretical results in as much detail as possible. There is no restriction on the length of the papers. The full experimental details must be provided so that the results can be reproduced. Electronic files and software regarding the full details of the calculation or experimental procedure, if unable to be published in a normal way, can be deposited as supplementary electronic material.
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