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Molecules 2018, 23(2), 498; https://doi.org/10.3390/molecules23020498

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

1,2,†,* , 1,2,†
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3,4
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1,2,* , 1,2
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1,5
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7
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1
School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
2
Innovative Research & Development Laboratory of TCM, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
3
School of Basic Medical Science, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
4
The Research Center of Basic Integrative Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China
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School of Basic Medical Science, Guangdong Pharmaceutical University, Guangzhou 510007, China
6
Zhongshan School of Medicine, Sun Yat-sen University, No. 74 Zhongshan Road. 2, Guangzhou 510080, China
7
Department of Histology and Embryology, Southern Medical University, Guangzhou 510515, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 24 January 2018 / Revised: 20 February 2018 / Accepted: 20 February 2018 / Published: 23 February 2018
(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products)
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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. View Full-Text
Keywords: acteoside; apiosyl; forsythoside B; phenylpropanoid glycosides; poliumoside; rhamnosyl acteoside; apiosyl; forsythoside B; phenylpropanoid glycosides; poliumoside; rhamnosyl
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Li, X.; Xie, Y.; Li, K.; Wu, A.; Xie, H.; Guo, Q.; Xue, P.; Maleshibek, Y.; Zhao, W.; Guo, J.; Chen, D. Antioxidation and Cytoprotection of Acteoside and Its Derivatives: Comparison and Mechanistic Chemistry. Molecules 2018, 23, 498.

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