Radical Scavenging Capability and Mechanism of Three Isoflavonoids Extracted from Radix Astragali: A Theoretical Study

被引:6
|
作者
Lu, Xiao-Qin [1 ]
Qin, Shu [1 ]
Li, Jindong [1 ]
机构
[1] Shanxi Agr Univ, Shanxi Ctr Testing Funct Agroprod, Taiyuan 030031, Peoples R China
来源
MOLECULES | 2023年 / 28卷 / 13期
关键词
antioxidant mechanism; radical scavenging reaction; isoflavonoids; DFT; structure-activity relationship; ANTIOXIDANT ACTIVITY; ANTIRADICAL ACTIVITY; THERMODYNAMICS; ENTHALPIES; CHEMISTRY; ELECTRON; DPPH;
D O I
10.3390/molecules28135039
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
As a valuable traditional Chinese herbal medicine, Radix Astragali has attracted much attention due to its extensive pharmacological activities. In this study, density functional theory (DFT) was used thermodynamically and kinetically in detail to predict the antioxidant activity and reaction mechanisms involved in the free radical scavenging reactions of three representative isoflavonoids (formononetin, calycosin, and calycosin-7-glucoside) extracted from Radix Astragali. Three main mechanisms, including hydrogen atom transfer (HAT), proton transfer after electron transfer (SET-PT), and sequential proton loss electron transfer (SPLET) were examined by calculating the thermodynamic parameters. It was found that HAT is the predominant mechanism in the gas phase, while SPLET is supported in the solvent environment. The isoflavonoids' order of antioxidant activity was estimated as: calycosin > calycosin-7-glucoside > formononetin. For the calycosin compound, the result revealed the feasibility of double HAT mechanisms, which involve the formation of stable benzodioxazole with significantly reduced energy in the second H+/e(-) reaction. In addition, the potential energy profiles and kinetic calculations show that the reaction of (OH)-O-& BULL; into the 3 & PRIME;-OH site of calycosin has a lower energy barrier (7.2 kcal/mol) and higher rate constant (4.55 x 10(9) M-1 s(-1)) compared with other reactions in the gas phase.
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页数:12
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