Synthesis, Radical-Scavenging Activities, and Protective Effects against AAPH-Induced Oxidative Damage in DNA and Erythrocytes of Piperine Derivatives

Abstract

Piperine amino acid derivatives containing phenolic hydroxyl groups were synthesized using piperine as the raw material by amide hydrolysis, amidation, ester hydrolysis, and deacetalization. The obtained products were characterized by mass spectrometry and nuclear magnetic resonance. The antioxidant activity of the piperine derivatives was evaluated by the DPPH and ABTS scavenging rates and the total antioxidant capacity. The results showed that the piperine amino acid (4a–4d) had relatively weak radical-scavenging ability, while the piperine amino acid derivatives (5a–5d) containing phenolic hydroxyl groups had significant radical-scavenging effects. In addition, the total reducing ability of 5a–5d was better than that of piperine. The study also found that piperine derivatives containing phenolic hydroxyl groups played an important role in inhibiting oxidative damage in DNA and erythrocytes.

Piperine: A review of its biological effects

“…An earlier piperine derivative, developed by Hering, Erker, Schwarz, Baburin, and Schellmann (2011), showed promising effects in the treatment of anxiety, epilepsy, insomnia, and depression via GABA A receptor modulation. In addition, recent research findings indicated that piperine amino acid derivatives have a better potential to mitigate oxidative stress than piperine (Qin, Yang, & Cao, 2020). Some piperine derivatives have been found as potent monoamine oxidase inhibitors and free radical scavengers.…”

Green Synthesis and Characterization of Silver Nanoparticles Using a Lythrum salicaria Extract and In Vitro Exploration of Their Biological Activities

“…Such compounds also have a protective effect on subcellular structures, proteins and DNA and can, thus, block pathological phenomena caused by oxidative stress [ 58 ]. Generally, the prooxidant action of peroxyl radicals generated by AAPH is blocked by compounds with hydroxyl groups that are capable of neutralizing and stabilizing the formed radicals [ 59 ].…”

Rational Design and Identification of Novel Piperine Derivatives as Multichitinase Inhibitors

“…The intermediate 3 was synthesized based on a previous study. 39 Intermediate 2 (2.0 g) was dissolved in anhydrous dichloromethane (DCM, 30.0 mL) with three drops of N,Ndimethylformamide (DMF). Then, SOCl 2 (1.4 g) was added dropwise to the reaction solution in an ice bath.…”

“…The intermediate 2 was synthesized referring to previous studies. − To a solution of piperine ( 1 , 10.0 g) in methanol (MeOH, 100 mL), 20% KOH aqueous solution (50.0 mL) was added. The reaction mixture was stirred at 70 °C for 24 h. After the reaction was completed, the pH of the reaction mixture was adjusted to 2∼3 with 0.1 M HCl aqueous solution.…”