Structure-activity relationship analysis of antioxidant ability and neuroprotective effect of gallic acid derivatives

Zhongbing Lu, Guangjun Nie, Peter S. Belton, Huiru Tang, Baolu Zhao

Research output: Contribution to journalArticlepeer-review

331 Scopus citations

Abstract

Gallic acid and its derivatives are a group of naturally occurring polyphenol antioxidants which have recently been shown to have potential healthy effects. In order to understand the relationship between the structures of gallic acid derivatives, their antioxidant activities, and neuroprotective effects, we examined their free radical scavenging effects in liposome and anti-apoptotic activities in human SH-SY5Y cell induced by 6-hydrodopamine autooxidation. It was found that these polyphenol antioxidants exhibited different hydrophobicity and could cross through the liposome membrane to react with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radical in a time and dose-dependent manner. At the same time, the structure-antioxidant activity relationship of gallic acid derivatives on scavenging DPPH free radical in the liposome was also analyzed based on theoretical investigations. Analysis of cell apoptosis, intracellular GSH levels, production of ROS and the influx of Ca2+ indicated that the protective effects of gallic acid derivatives in cell systems under oxidative stress depend on both their antioxidant capacities and hydrophobicity. However, the neuroprotective effects of gallic acid derivatives seem to depend more on their molecular polarities rather than antioxidant activities in the human SH-SY5Y cell line. In conclusion, these results reveal that compounds with high antioxidant activity and appropriate hydrophobicity are generally more effective in preventing the injury of oxidative stress in neurodegenerative diseases.

Original languageEnglish (US)
Pages (from-to)263-274
Number of pages12
JournalNeurochemistry International
Volume48
Issue number4
DOIs
StatePublished - Mar 2006

Keywords

  • Antioxidant
  • Apoptosis
  • ESR
  • Free radicals
  • Gallic acid
  • Glutathione
  • Hydrophobicity
  • Oxidative stress
  • Partition coefficient
  • Reactive oxygen species

ASJC Scopus subject areas

  • Cell Biology
  • Molecular Biology
  • Cellular and Molecular Neuroscience

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