Antioxidation and Cytoprotection of Acteoside and Its Derivatives: Comparison and Mechanistic Chemistry.

Xican Li,Ke Li,Dongfeng Chen,Penghui Xue,Wei Zhao,Qian Guo,Aizhi Wu,Hong Xie,Yulu Xie,Jiasong Guo,Yerkingul Maleshibek

doi:10.3390/molecules23020498

Abstract

The study tried to explore the role of sugar-residues and mechanisms of phenolic phenylpropanoid antioxidants. Acteoside, along with its apioside forsythoside B and rhamnoside poliumoside, were comparatively investigated using various antioxidant assays. In three electron-transfer (ET)-based assays (FRAP, CUPRAC, PTIO•-scavenging at pH 4.5), the relative antioxidant levels roughly ruled as: acteoside >forsythoside B > poliumoside. Such order was also observed in H+-transfer-involved PTIO•-scavenging assay at pH 7.4, and in three multiple-pathway-involved radical-scavenging assays, i.e., ABTS+•-scavenging, DPPH•-scavenging, and •O2−-scavenging. In UV-vis spectra, each of them displayed a red-shift at 335→364 nm and two weak peaks (480 and 719 nm), when mixed with Fe2+; however, acteoside gave the weakest absorption. In Ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC−ESI−Q−TOF−MS/MS) analysis, no radical-adduct-formation (RAF) peak was found. MTT assay revealed that poliumoside exhibited the highest viability of oxidative-stressed bone marrow-derived mesenchymal stem cells. In conclusion, acteoside, forsythoside B, and poliumoside may be involved in multiple-pathways to exert the antioxidant action, including ET, H+-transfer, or Fe2+-chelating, but not RAF. The ET and H+-transfer may be hindered by rhamnosyl and apiosyl moieties; however, the Fe2+-chelating potential can be enhanced by two sugar-residues (especially rhamnosyl moiety). The general effect of rhamnosyl and apiosyl moieties is to improve the antioxidant or cytoprotective effects.

Highlights

Acteoside, a phenolic phenylpropanoid glycoside occurring Recently, improve the efficiency of canineglycoside somatic occurring cell nuclear vervain and other plants [1], was found to improve the efficiency of canine somatic cell nuclear transfer (SCNT) during the dog-cloning process [2]
As illustrated in Suppl. 1, acteoside and its derivatives increased the relative ferric ion reducing antioxidant power (FRAP) percentages at 0–10 μg/L in a dose-dependent manner. Their order of relative metal-reducing levels roughly decreased in the order of acteoside > forsythoside B > poliumoside (Table 1)
Acteoside, forsythoside B, and poliumoside, experiment was performed in pentaplicate

Summary

Introduction

Acteoside (verbascoside, Figure 1), a phenolic phenylpropanoid glycoside occurring Recently, Figure a phenolic phenylpropanoid in in vervain andacteoside other plants [1], was found to 1), improve the efficiency of canineglycoside somatic occurring cell nuclear vervain and other plants [1], was found to improve the efficiency of canine somatic cell nuclear transfer (SCNT) during the dog-cloning process [2]. Acteoside could protect human transfer (SCNT)SH-SY5Y during the process [2]. Could skin protect human neuroblastoma cellsdog-cloning against β-amyloid-induced damage acteoside [3] and human fibroblasts neuroblastoma. Is distributed in plants plants [5], and has been observed to exert potent neuroprotective effects with a favorable therapeutic [5], and has been to exert effects potent on neuroprotective effects a favorable therapeutic timetime-window [6]. Is distributed in plants plants [5], and has been observed to exert potent neuroprotective effects with a favorable therapeutic [5], and has been to exert effects potent on neuroprotective effects a favorable therapeutic timetime-window [6]. observed

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Discussion

Conclusion