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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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References

    1. Li Y.L., Lu J.X., Li X.H., Han Q., Jiang X.T. The study of active ingredients on 8 traditional Chinese Medicines by the Brine Shrimp Letality Bioassay. Acta Bot. Boreali-Occident. Sin. 1994;4:324.
    1. Le J., Lu W., Xiong X., Wu Z., Chen W. Anti-inflammatory constituents from Bidens frondosa. Molecules. 2015;20:18496–18510. doi: 10.3390/molecules201018496. - DOI - PMC - PubMed
    1. Sheliya M.A., Rayhana B., Ali A., Pillai K.K., Aeri V., Sharma M., Mir S.R. Inhibition of α-glucosidase by new prenylated flavonoids from Euphorbia hirta L. herb. J. Ethnopharmacol. 2015;176:1–8. doi: 10.1016/j.jep.2015.10.018. - DOI - PubMed
    1. Panighel A., De R.M., Dalla V.A., Flamini R. Putative identification of new p-coumaroyl glycoside flavonoids in grape by ultra-high performance liquid chromatography/high-resolution mass spectrometry. Rapid Commun. Mass Spectrom. 2015;29:357–366. doi: 10.1002/rcm.7115. - DOI - PubMed
    1. Tohge T., Zhang Y., Peterek S., Matros A., Rallapalli G., Tandrón Y.A., Butelli E., Kallam K., Hertkorn N., Mock H.P., et al. Ectopic expression of snapdragon transcription factors facilitates the identification of genes encoding enzymes of anthocyanin decoration in tomato. Plant. J. 2015;83:686–704. doi: 10.1111/tpj.12920. - DOI - PubMed

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