Synthesis and Antioxidative Activity of Piperine Derivatives Containing Phenolic Hydroxyl

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...

Full description

Saved in:
Bibliographic Details
Main Authors: Bei Qin, Kuan Yang, Ruijun Cao
Format: Article
Language:English
Published: Wiley 2020-01-01
Series:Journal of Chemistry
Online Access:http://dx.doi.org/10.1155/2020/2786359
Tags: Add Tag
No Tags, Be the first to tag this record!
_version_ 1832560141877116928
author Bei Qin
Kuan Yang
Ruijun Cao
author_facet Bei Qin
Kuan Yang
Ruijun Cao
author_sort Bei Qin
collection DOAJ
description 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.
format Article
id doaj-art-d258fd392f5f48789b7eaa3a5615d40e
institution Kabale University
issn 2090-9063
2090-9071
language English
publishDate 2020-01-01
publisher Wiley
record_format Article
series Journal of Chemistry
spelling doaj-art-d258fd392f5f48789b7eaa3a5615d40e2025-02-03T01:28:20ZengWileyJournal of Chemistry2090-90632090-90712020-01-01202010.1155/2020/27863592786359Synthesis and Antioxidative Activity of Piperine Derivatives Containing Phenolic HydroxylBei Qin0Kuan Yang1Ruijun Cao2School of Science, Xi’an Jiaotong University, Xi’an 710049, Shaanxi, ChinaDepartment of Pharmacy, Xi’an Medical University, Xi’an 710021, Shaanxi, ChinaSchool of Science, Xi’an Jiaotong University, Xi’an 710049, Shaanxi, ChinaPiperine 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.http://dx.doi.org/10.1155/2020/2786359
spellingShingle Bei Qin
Kuan Yang
Ruijun Cao
Synthesis and Antioxidative Activity of Piperine Derivatives Containing Phenolic Hydroxyl
Journal of Chemistry
title Synthesis and Antioxidative Activity of Piperine Derivatives Containing Phenolic Hydroxyl
title_full Synthesis and Antioxidative Activity of Piperine Derivatives Containing Phenolic Hydroxyl
title_fullStr Synthesis and Antioxidative Activity of Piperine Derivatives Containing Phenolic Hydroxyl
title_full_unstemmed Synthesis and Antioxidative Activity of Piperine Derivatives Containing Phenolic Hydroxyl
title_short Synthesis and Antioxidative Activity of Piperine Derivatives Containing Phenolic Hydroxyl
title_sort synthesis and antioxidative activity of piperine derivatives containing phenolic hydroxyl
url http://dx.doi.org/10.1155/2020/2786359
work_keys_str_mv AT beiqin synthesisandantioxidativeactivityofpiperinederivativescontainingphenolichydroxyl
AT kuanyang synthesisandantioxidativeactivityofpiperinederivativescontainingphenolichydroxyl
AT ruijuncao synthesisandantioxidativeactivityofpiperinederivativescontainingphenolichydroxyl