A novel salvianolic acid A analog with resveratrol structure and its antioxidant activities in vitro and in vivo

Abstract

E‐DRS is a novel salvianolic acid A (SAA) analog, which was synthesized from resveratrol (RES) and methyldopate. Its structure is similar to that of SAA, but the 3′,4′‐dihydroxy‐trans‐stilbene group and the ester structure in SAA were replaced by the RES structure and an amine group, respectively. E‐DRS scavenged free oxygen radicals effectively, including superoxide anion (ascorbic acid > E‐DRS > SAA ≥ rutin > RES) and DPPH radical (rutin > E‐DRS ≥ ascorbic acid > SAA > RES), and exhibited powerful total antioxidant capacity (ascorbic acid > E‐DRS > SAA ≥ rutin > RES) in vitro. Furthermore, oral administration of E‐DRS dose‐dependently and significantly decreased CCl4‐induced oxidative stress in mice as indicated by the decreased content of hepatic malondialdehyde (MDA). In addition, oral administration of E‐DRS also increased the content of nonenzymatic antioxidant glutathione (GSH) and the activity of antioxidant enzymes such as catalase (CAT) and superoxide dismutase (SOD) in the liver of mice. All these results demonstrated that E‐DRS had good antioxidant activities both in vitro and in vivo, and could be a potential antioxidant agent after further optimization and evaluation.

Reactivity of trans-Resveratrol toward Electrogenerated Superoxide in N,N-Dimethylformamide

“…The difference between the ΔG° values of the concerted PCET derives from the position of OH, suggesting that the PCET at 4'OH (−26.7) is morefeasible rather than at 3OH (−1.9). These results show that the stilbene-double-bond with the para-OH plays a role in resonance, resulting in promotion of the PCET at 4'OH [12][13][14][15]. As shown in the electrochemical results, the PCET between O2 •− and RsvH3 occurs as an intra-complex reaction via two or three HBs on two phenolic rings linked by stilbene-double-bond.…”

“…25,33,37 Notably, PT4 is exergonic (−45.8, −70.6), meaning that the second PT must be coupled to ET via a HB. Considering together that 4'OH in the para-position plays a significant role in resonance for a successful ET, [12][13][14][15] the second PT coupled to ET feasibly occur in 4'OH. For a comparative study, the ΔG° values of the PCET pathways of RsvH3, pinosylvin, pterostilbene, and p-coumaric acid, were calculated using three functionals, B3LYP, ω-B97XD, and M06-2X (Table 1).…”

“…Numerous antioxidant studies of RsvH3 and related compounds have been reported using different assays and methodologies, with reference to the structure-activity or property relationship related to the number and position of the hydroxy group (OH). [12][13][14][15] In these studies, the electron-donating ability of phenolic compounds such as RsvH3 for their antioxidant activity is discussed. Furthermore, experimental data demonstrate that if the OH is scavenged or replaced by the methoxy group, the molecule loses its activity, suggesting that OH plays a role as a proton donor besides as a substituent with an electronic inductive effect along the electron donation.…”

“…From the viewpoint of the structure-property (electron donating) relationship of RsvH3, the position of OH mainly contributes to the activity, due to its higher degree of conjugation with 4'OH and the capability to delocalize the -electrons characterized by stilbene-double-bond with its resonance structure. [12][13][14][15] The resonance effect with -conjugation is considered to thermodynamically stabilize the radical product. Furthermore, the coplanar molecular-structure of the trans-stilbene skeleton may expand the -conjugation into two phenolic rings and the meta-OH groups, resulting in enhanced ROS-scavenging ability of RsvH3.…”

Stability and antioxidant activity of flavonoids from Lycium barbarum L. leaves during digestion in vivo

“…The accumulation of free radicals attacks the polyunsaturated fatty acids on the biofilm when free radical generation is excessive, leading to lipid peroxidation and the production of MDA. However, MDA can cause crosslinking of essential macromolecular polymers, such as proteins and nucleic acids, and affect the fluidity and permeability of cell membranes, limiting their normal function (Qiu et al, 2021).…”