Abstract
Puerarin is a C-glycoside of daidzein, one of the major bioactive ingredients isolated from the root of Pueraria lobata, which has a wide spectrum of pharmacological effects. Although puerarin is well-known for its effective antioxidant activity, there is seldom a systematic theoretical study on its radical scavenging activity. Herein, the free radical scavenging ability of puerarin was investigated systematically by density functional theory (DFT) calculations. The reaction activity was compared with daidzein as well. Three reaction pathways: hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) were discussed and compared by thermodynamic parameters such as bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA), and electron transfer enthalpy (ETE). The reaction kinetics of puerarin with special radicals •OH and •OOH were also studied. The results obtained may be of great significance for better understanding the relationship between the antioxidant properties and structural design of puerarin, as well as other antioxidants.
Highlights
Reactive oxygen species (ROS) are among the most harmful free radicals in the human body, such as hydroxyl radical (OH), superoxide anion radical (O2− ), peroxyl radicals (ROO), etc. [1,2].If excessive ROS are produced in vivo, the antioxidant system will be out of balance, called oxidative stress, which could damage the structures and functions of the biological macromolecules such as lipids, proteins, RNA, and DNA [3,4]
The radical scavenging activity of puerarin was investigated under the theoretical level of
It reveals that hydrogen atom transfer (HAT) should be the preferred mechanism in non-polar solvents, while sequential proton loss electron transfer (SPLET)
Summary
If excessive ROS are produced in vivo, the antioxidant system will be out of balance, called oxidative stress, which could damage the structures and functions of the biological macromolecules such as lipids, proteins, RNA, and DNA [3,4]. Numerous human diseases are related to oxidative stress, like aging, atherosclerosis, diabetes, and Parkinson’s disease [5,6]. Synthetic antioxidants such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), propyl gallate, and tert-butyl hydroquinone (TBHQ) are widely used as antioxidants or preservatives in foods, medicines, animal feeds, petroleum products, cosmetics, rubbers, etc. Synthetic antioxidants often cause toxic and carcinogenic problems [7,8]. The development of more efficient, less toxic, and safer natural antioxidants has attracted broad interest. Introduction of a glucose moiety makes puerarin strongly hydrophilic. Of of a glucose moiety makes puerarin strongly hydrophilic. 10−6 M [27], makes which water, 1.1in×water, 10−2 M much better than that of daidzein, only 5.3 × 10−6 M× [27], which makes puerarin’s oral bioavailability much than better than daidzein puerarin’s oral bioavailability much better daidzein [28]. [28].
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