A combined experimental–theoretical study of the acid–base behavior of mangiferin: implications for its antioxidant activity

Mendoza-Sarmiento, Gabriela; Rojas-Hernándéz, Alberto; Galano, Annia; Gutiérrez, Ana Rosa

doi:10.1039/c6ra06328d

Cited by 16 publications

(6 citation statements)

References 71 publications

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“…29 In addition, mangiferin characterised from the 30EE showed excellent antioxidant power. 30 Previously xanthones and several benzophenone glycosides isolated from A. sinensis leave exhibited a strong α-glucosidase inhibitory activity, 27 which is consistent with our results. In additions, newly reported mangiferin dimer and trimer in A. sinensis leaves were also identified in 75EE to…”

Section: Profiling Of Potential Bioactive Compounds With Ms/ms Mnsupporting

confidence: 90%

Tandem mass spectrometry (MS/MS) molecular networking guided profiling of small molecules from Aquilaria sinensis (Lour.) Gilg leaves and their bioactivity evaluation

Yang,

Sun,

Yang

et al. 2023

Phytochemical Analysis

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IntroductionAgarwood, a fragrant resinous wood mainly formed by Aquilaria spp., is used worldwide as a natural fragrance and traditional medicine. A large amount of Aquilaria sinensis (Lour.) Gilg leaves are underutilised during the process of the agarwood industry, and the development of A. sinensis leaves as tea has recently attracted more and more attention. However, the small molecule profile of A. sinensis leaves and their bioactivities has been rarely reported.ObjectiveTo conduct a rapid untargeted liquid chromatography–mass spectrometry (LC–MS) analysis of A. sinensis leaves with a molecular networking (MN) strategy and evaluate its antioxidant and antidiabetic value.MethodA MN‐assisted tandem mass spectrometry (MS/MS) analysis strategy was used to investigate the small molecule profile of A. sinensis leaves. Additionally, the integration of antioxidant and α‐glucosidase inhibitory assays with MN analysis was executed to expeditiously characterise the bioactive compounds for potential prospective application.ResultsFive main chemical groups including phenol C‐glycosides, organic acids, 2‐(2‐phenylethyl) chromones, benzophenone O‐glycosides and flavonoids were rapidly revealed from the A. sinensis leaves. Eighty‐one compounds were provisionally identified by comparing their MS/MS fragments with canonical pathways. The featured xanthone C‐glycosides and benzophenone C‐glycosides were recognised as the primary components of A. sinensis leaves. Several dimers and a trimer of mangiferin were reported firstly in A. sinensis leaves. Furthermore, 17 and 14 potential bioactive molecules were rapidly annotated from antioxidant and α‐glucosidase inhibitory fraction, respectively.ConclusionOur findings will help expand the utilisation of A. sinensis leaves and thus promote the high‐quality development of agarwood industry.

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Section: Profiling Of Potential Bioactive Compounds With Ms/ms Mnsupporting

confidence: 90%

Tandem mass spectrometry (MS/MS) molecular networking guided profiling of small molecules from Aquilaria sinensis (Lour.) Gilg leaves and their bioactivity evaluation

Yang,

Sun,

Yang

et al. 2023

Phytochemical Analysis

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“…However, it should be noted that such low proportion does not necessarily mean that these species are unimportant for the antioxidant or pro-oxidant activity of PhCs. The product of M f by the rate corresponding rate constant would really matter. − …”

Section: Resultsmentioning

confidence: 99%

Comprehensive Investigation of the Antioxidant and Pro-oxidant Effects of Phenolic Compounds: A Double-Edged Sword in the Context of Oxidative Stress?

et al. 2018

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Oxidative stress (OS) is a health-threatening process that is involved, at least partially, in the development of several diseases. Although antioxidants can be used as a chemical defense against OS, they might also exhibit pro-oxidant effects, depending on environmental conditions. In this work, such a dual behavior was investigated for phenolic compounds (PhCs) within the framework of the density functional theory and based on kinetic data. Multiple reaction mechanisms were considered in both cases. The presence of redox metals, the pH, and the possibility that PhCs might be transformed into benzoquinones were identified as key aspects in the antioxidant versus pro-oxidant effects of these compounds. The main virtues of PhCs as antioxidants are their radical trapping activity, their regeneration under physiological conditions, and their behavior as OH-inactivating ligands. The main risks of PhCs as pro-oxidants are predicted to be the role of phenolate ions in the reduction of metal ions, which can promote Fenton-like reactions, and the formation of benzoquinones that might cause protein arylation at cysteine sites. Although the benefits seem to overcome the hazards, to properly design chemical strategies against OS using PhCs, it is highly recommended to carefully explore their duality in this context.

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“…Mangiferin is a C-glucosyl xanthone present in considerable levels in higher plants and different parts of the mango fruit, such as the peel, stalks, leaves, barks, kernel and stone [3] . Numerous studies confirm that mangiferin, through different mechanisms, has various biological activities such as anti-cancer [4] , antioxidant [5] , anti-inflammatory, anti-diabetic [6] , cardiovascular protection [7] , neuroprotective [8] , antiviral, enhanced immunity, gastroprotective effect, analgesic activity and radioprotection, as seen in the experiments on mice. The neuroprotective effect was patented, also anti-allergic properties and hepatoprotective activity have been published [9] .…”

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confidence: 85%

Development and Validation of High Performance Thin Layer Chromatography Method for Standardization of Polyherbal Formulation Using Mangiferin and Gallic Acid as Markers

Hage¹,

Jadhav²

2022

IJPS

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Hage et al.: Simultaneous Estimation of Mangiferin and Gallic acid by High Performance Thin Layer ChromatographyOxitard capsules, a polyherbal formulation, is an effective natural antioxidant that prevents oxidative stress-related tissue damage and is helpful for coronary artery disease. The aim of the present work was systematic development and validation of the high-performance thin-layer chromatographic method for simultaneous quantitative estimation of mangiferin and gallic acid from oxitard capsules. Both markers, mangiferin and gallic acid were separated on a pre-coated silica gel 60 F 254 thin-layer chromatographic plate, using toluene:ethyl acetate:formic acid:methanol (4:6:0.8:2 v/v/v/v) as mobile phase. The retention factor of mangiferin and gallic acid was found to be 0.28±0.03 and 0.78±0.03, respectively. The linear regression analysis data for the calibration plots of drugs scanned at isosbestic point 299 nm showed a good linear relationship with r 2 =0.9931 and r 2 =0.9901, over the concentration range of 300 to 700 ng/spot and 500 to 900 ng/spot for mangiferin and gallic acid, respectively. The validation parameter followed for simultaneous estimation of these polyherbal drugs were linearity, precision, accuracy, robustness, ruggedness and sensitivity (limit of detection and limit of quantitation). The method was found to be precise, accurate, sensitive and robust meeting all the parameters as per International Council for Harmonisation guideline Q2 (R1). Thus, the developed high-performance thin-layer chromatography method can conveniently be employed for simultaneous detection and quantification of mangiferin and gallic acid in commercial polyherbal formulation.

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A combined experimental–theoretical study of the acid–base behavior of mangiferin: implications for its antioxidant activity

Abstract: The pKavalues of mangiferin have been thoroughly reviewed to calculate theoretically the mechanism and antioxidant features of mangiferin.

Cited by 16 publications

References 71 publications

Tandem mass spectrometry (MS/MS) molecular networking guided profiling of small molecules from Aquilaria sinensis (Lour.) Gilg leaves and their bioactivity evaluation

Tandem mass spectrometry (MS/MS) molecular networking guided profiling of small molecules from Aquilaria sinensis (Lour.) Gilg leaves and their bioactivity evaluation

Comprehensive Investigation of the Antioxidant and Pro-oxidant Effects of Phenolic Compounds: A Double-Edged Sword in the Context of Oxidative Stress?

Development and Validation of High Performance Thin Layer Chromatography Method for Standardization of Polyherbal Formulation Using Mangiferin and Gallic Acid as Markers

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