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Comparative Study
. 2017 Jul 12;22(7):1165.
doi: 10.3390/molecules22071165.

Role of the p-Coumaroyl Moiety in the Antioxidant and Cytoprotective Effects of Flavonoid Glycosides: Comparison of Astragalin and Tiliroside

Xican Li  1   2 , Yage Tian  3 , Tingting Wang  4   5 , Qiaoqi Lin  6 , Xiaoyi Feng  7 , Qian Jiang  8   9 , Yamei Liu  10 , Dongfeng Chen  11
Affiliations
Comparative Study

Role of the p-Coumaroyl Moiety in the Antioxidant and Cytoprotective Effects of Flavonoid Glycosides: Comparison of Astragalin and Tiliroside

Xican Li et al. Molecules. .

Abstract

The aim of this study was to explore the role of p-coumaroyl in the antioxidant and cytoprotective effects of flavonoid glycosides. The antioxidant effects of astragalin and tiliroside were compared using ferric ion reducing antioxidant power, DPPH• scavenging, ABTS•⁺ scavenging, •O₂- scavenging, and Fe2+-chelating assays. The results of these assays revealed that astragalin and tiliroside both exhibited dose-dependent activities; however, tiliroside exhibited lower IC50 values than astragalin. In the Fe2+-chelating assay, tiliroside gave a larger shoulder-peak at 510 nm than astragalin, and was also found to be darker in color. Both of these compounds were subsequently evaluated in a Fenton-induced mesenchymal stem cell (MSC) damaged assay, where tiliroside performed more effectively as a cytoprotective agent than astragalin. Tiliroside bearing a 6''-O-p-coumaroyl moiety exhibits higher antioxidant and cytoprotective effects than astragalin. The 6''-O-p-coumaroyl moiety of tiliroside not only enhances the possibility of electron-transfer and hydrogen-atom-transfer-based multi-pathways, but also enhances the likelihood of Fe-chelating. The p-coumaroylation of the 6"-OH position could therefore be regarded as a potential approach for improving the antioxidant and cytoprotective effects of flavonoid glycosides in MSC implantation therapy.

Keywords: astragalin; flavonoid glycoside; mesenchymal stem cells; p-coumaroyl; tiliroside.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of astragalin (A) and tiliroside (B).
Figure 2
Figure 2
Dose-response curves of astragalin and tiliroside in various antioxidant assays: (A) FRAP assay; (B) ABTS scavenging assay; (C) DPPH•-scavenging assay; (D) •O2–-scavenging assay. Each value is expressed mean ± SD, n = 3. Trolox was used as the positive control.
Figure 3
Figure 3
UV spectra of astragalin and tiliroside (A); and the physical appearances of the astragalin-Fe and tiliroside-Fe complexes (B).
Figure 4
Figure 4
Ball-and-stick models based on preferential conformation of astragalin (A) and tiliroside (B).
Figure 5
Figure 5
Proposed reaction of tiliroside chelating Fe2+.
Figure 6
Figure 6
Protective effects of astragalin (A) and tiliroside (B) against the •OH-induced damage of MSCs using an MTT assay. The •OH radicals were generated by Fenton reagent (FeCl2 plus H2O2). These data represent the mean ± SD (n = 5). * p < 0.05 vs model.
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