Abstract
Piperine was used in this study in its raw form, and different steps, such as amide hydrolysis and amidation, were used to synthesize piperine derivatives containing a phenolic hydroxyl group. DPPH and ABTS free radical scavenging assays were used to assess piperine derivative antioxidant activities. We constructed an AAPH oxidative stress erythrocyte model to study the effect of piperine derivatives on the hemolysis rate of oxidatively damaged erythrocytes as well as the hemoglobin oxidation rate. This AAPH model was also used to determine piperine derivative effects on antioxidant enzyme activity and malondialdehyde (MDA) content. Results showed that spectroscopic methods could synthesize and identify piperine derivatives containing phenolic hydroxyl groups (H-1∼H-3). Moreover, DPPH and ABTS assay results showed that piperine derivative free radical clearance rates were higher compared with the parent compound. Additionally, piperine derivatives (H-1∼H-3) were found to provide protection to AAPH oxidatively damaged erythrocytes in their ability to inhibit AAPH-induced erythrocyte lysis, while hemoglobin oxidation was higher compared with the parent compound. Piperine derivatives may protect intracellular glutathione peroxidase (GSH-Px) antioxidant enzyme system activities, safeguarding against oxidative damage. This study synthesized novel piperine derivatives for use as potential antioxidant agent candidates.
Highlights
Free radicals refer to any molecule with one or more unpaired electrons that is a product of normal body metabolism [1]
Greater than 80% of DPPH free radicals were cleared at 0.625 mmol/L of piperine derivative 1. e IC50 value reflects the 50% inhibitory concentration of the antioxidant being measured. erefore, lower IC50 values correspond to the higher antioxidative capacity of the substance
We demonstrated that the free radical clearance rates of piperine derivatives were higher compared with the parent compound
Summary
Free radicals refer to any molecule with one or more unpaired electrons that is a product of normal body metabolism [1]. Piperine is an active alkaloid that is extracted from peppers, long peppers, and other plants It produces a variety of physiological and pharmacological effects to occur, such as antioxidative [7], antilipid [8], immunoregulative, antitumor [9], and anti-inflammatory effects [10]. One study found that piperine inhibited oxidative damage levels that could potentially be associated with its effect on reducing free radicals and reactive oxygen species (ROS) [7]. Studies have shown that piperine antioxidant activities are associated with the molecule’s carbon-oxygen five-membered rings and amide structure. Piperine reportedly undergoes demethylation of its carbon-oxygen five-membered rings during metabolism in the human body, mainly producing metabolites with a bisphenol hydroxyl structure [12]. Piperine reportedly undergoes demethylation of its carbon-oxygen five-membered rings during metabolism in the human body, mainly producing metabolites with a bisphenol hydroxyl structure [12]. e consequent synthesis
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