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

Li, Xican; Yuan, Tian; Wang, Tingting; Lin, Qiaoqi; Feng, Xiaoyi; Jiang, Qian; Chen, Dongfeng

doi:10.3390/molecules22071165

Cited by 40 publications

(33 citation statements)

References 41 publications

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“…Also anthocyanins with the 6-p-coumaroyl moiety negatively contribute to ORAC. Nevertheless, they displayed positive statistically significant correlations with FRAP, corroborating they are capable of quenching Fe +3 and HO  radicals generated from a Fenton reaction by hydrogen transfer atom (HAT) mechanism with Fe +3 (Li et al, 2017).…”

Section: Compounds Contributing To Antioxidant Activitymentioning

confidence: 77%

Phenolic characterization of aging wine lees: Correlation with antioxidant activities

et al. 2018

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Aging wine lees are water-wastes produced during the wine aging inside wood barrels that can be considered as alternative sources of bioactive compounds. Phenolic characterization and antioxidant activity (AA) measurements of wines lees solid-liquid extracts have been undertaken on a dry extract (DE) basis. Solvents with different polarities (water, methanol, ethanol, two hydroalcoholic mixtures and acetone) were used. Total phenolic (TPC) and total flavonoid contents (TFC) were determined. The mixture of 75:25(v/v) EtOH:HO showed the highest values with 254 mg/g and 146 mg/g respectively. HORAC, HOSC and FRAP were used to determine the AA of the extracts being also highest for the mixture of 75:25(v/v) EtOH:HO (4690 µmol/g, 4527 µmol/g and 2197 µmol/g, respectively). For ORAC method, methanol extract showed the best value with 2771 µmol/g. Correlations between TPC, TFC, phenolic compounds and AA were determined. Most relevant compounds contributing to AA were identified using data from mass spectrometry, being mainly anthocyanins.

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Section: Compounds Contributing To Antioxidant Activitymentioning

confidence: 77%

Phenolic characterization of aging wine lees: Correlation with antioxidant activities

et al. 2018

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“…As an alkaloid, higenamine is reported to have various pharmacological properties, such as anti-thrombotic, anti-apoptotic, anti-inflammatory, and immunomodulatory effects [ 15 ]. According to free radical biology and medicine, these pharmacological properties are associated with antioxidative effects [ 16 , 17 ]. For instance, higenamine decreases the release of cytochrome c (a cellular oxidative promotor), and decreases apoptotic cell death in myocardial ischemia-reperfused rats [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

pH Effect and Chemical Mechanisms of Antioxidant Higenamine

Xie

Chen

et al. 2018

Molecules

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In this article, we determine the pH effect and chemical mechanism of antioxidant higenamine by using four spectrophotometric assays: (1) 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide radical (PTIO•)-scavenging assay (at pH 4.5, 6.0, and 7.4); (2) Fe3+-reducing power assay; (3) Cu2+-reducing power assay; and (4) 1,1-diphenyl-2-picryl-hydrazyl (DPPH•)-scavenging assay. The DPPH•-scavenging reaction product is further analyzed by ultra-performance liquid chromatography, coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) technology. In the four spectrophotometric assays, higenamine showed good dose-response curves; however, its IC50 values were always lower than those of Trolox. In UPLC-ESI-Q-TOF-MS/MS analysis, the higenamine reaction product with DPPH• displayed three chromatographic peaks (retention time = 0.969, 1.078, and 1.319 min). The first gave m/z 541.2324 and 542.2372 MS peaks; while the last two generated two similar MS peaks (m/z 663.1580 and 664.1885), and two MS/MS peaks (m/z 195.9997 and 225.9971). In the PTIO•-scavenging assays, higenamine greatly decreased its IC50 values with increasing pH. In conclusion, higenamine is a powerful antioxidant—it yields at least two types of final products (i.e., higenamine-radical adduct and higenamine-higenamine dimer). In aqueous media, higenamine may exert its antioxidant action via electron-transfer and proton-transfer pathways. However, its antioxidant action is markedly affected by pH. This is possibly because lower pH value weakens its proton-transfer pathway via ionization suppression by solution H+, and its electron-transfer pathway by withdrawing the inductive effect (-I) from protonated N-atom. These findings will aid the correct use of alkaloid antioxidants.

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“…The dose-response curves were plotted using Origin 6.0 professional software (OriginLab, Northampton, MA, USA). The IC 50 value was defined as the concentration required for 50% radical inhibition (or relative reducing power) [58]. It was calculated by linear regression analysis and is expressed as the mean ± SD (n = 3).…”

Section: Discussionmentioning

confidence: 99%

Inhibitory Effect and Mechanism of Action of Quercetin and Quercetin Diels-Alder anti-Dimer on Erastin-Induced Ferroptosis in Bone Marrow-Derived Mesenchymal Stem Cells

Zeng

Liu

et al. 2020

Antioxidants

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In this study, the anti-ferroptosis effects of catecholic flavonol quercetin and its metabolite quercetin Diels-Alder anti-dimer (QDAD) were studied using an erastin-treated bone marrow-derived mesenchymal stem cell (bmMSCs) model. Quercetin exhibited higher anti-ferroptosis levels than QDAD, as indicated by 4,4-difluoro-5-(4-phenyl-1,3-butadienyl)-4-bora-3a,4a-diaza-s-indacene-3-undecanoic acid (C11-BODIPY), 2′,7′-dichlorodihydrofluoroscein diacetate (H2DCFDA), lactate dehydrogenase (LDH) release, cell counting kit-8 (CCK-8), and flow cytometric assays. To understand the possible pathways involved, the reaction product of quercetin with the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH●) was measured using ultra-performance liquid-chromatography coupled with electrospray-ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-ESI-Q-TOF-MS). Quercetin was found to produce the same clusters of molecular ion peaks and fragments as standard QDAD. Furthermore, the antioxidant effects of quercetin and QDAD were compared by determining their 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide radical-scavenging, Cu2+-reducing, Fe3+-reducing, lipid peroxidation-scavenging, and DPPH●-scavenging activities. Quercetin consistently showed lower IC50 values than QDAD. These findings indicate that quercetin and QDAD can protect bmMSCs from erastin-induced ferroptosis, possibly through the antioxidant pathway. The antioxidant pathway can convert quercetin into QDAD—an inferior ferroptosis-inhibitor and antioxidant. The weakening has highlighted a rule for predicting the relative anti-ferroptosis and antioxidant effects of catecholic flavonols and their Diels-Alder dimer metabolites.

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

Cited by 40 publications

References 41 publications

Phenolic characterization of aging wine lees: Correlation with antioxidant activities

Phenolic characterization of aging wine lees: Correlation with antioxidant activities

pH Effect and Chemical Mechanisms of Antioxidant Higenamine

Inhibitory Effect and Mechanism of Action of Quercetin and Quercetin Diels-Alder anti-Dimer on Erastin-Induced Ferroptosis in Bone Marrow-Derived Mesenchymal Stem Cells

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