Monoalkylated Epigallocatechin-3-gallate (C18-EGCG) as Novel Lipophilic EGCG Derivative: Characterization and Antioxidant Evaluation

Minnelli, Cristina; Galeazzi, Roberta; Laudadio, Emiliano; Amici, Adolfo; Rusciano, Dario; Armeni, Tatiana; Cantarini, Mattia; Mobbili, Giovanna

doi:10.3390/antiox9030208

Cited by 32 publications

(32 citation statements)

References 55 publications

(64 reference statements)

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“…All catechins are known to interact with the lipid bilayer, EGCG having higher affinity for membranes than non-esterified catechins [ 31 ]. However, AAPH is a water-soluble compounds and water-soluble antioxidants must be important in scavenging radicals generated by AAPH decomposition, while membrane-interacting antioxidants are crucial for inhibiting the chain process of lipid peroxidation [ 32 ].…”

Section: Resultsmentioning

confidence: 99%

Comparison of Antioxidants: The Limited Correlation between Various Assays of Antioxidant Activity

et al. 2020

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The inhibitory effects a range of synthetic and natural antioxidants on lipid peroxidation of egg yolk and erythrocyte membranes induced by a free radical generator 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH) was compared, with significant differences being found between both systems. When the protection by selected antioxidants against the effects of AAPH on erythrocytes (hemolysis, oxidation of hemoglobin and glutathione (GSH) and generation of reactive oxygen species (ROS)) was studied, most antioxidants were protective, but in some tests (oxidation of hemoglobin and GSH) some acted as prooxidants, inducing oxidation in the absence of AAPH and enhancing the AAPH-induced oxidation. These results demonstrate a diversified action of antioxidants in different systems and point to a need for careful extrapolation of any conclusions drawn from one parameter or experimental system to another.

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Section: Resultsmentioning

confidence: 99%

Comparison of Antioxidants: The Limited Correlation between Various Assays of Antioxidant Activity

et al. 2020

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“…Strategies to enhance the bioavailability of compounds have been employed based on changes in drug formulation, or modification to the chemical structure. Nanoparticle, micelle, and liposome-based drug formulations which encapsulates the drug in the particles have been successful in improving bioavailability [140][141][142][143][144]. Due to their small size and permeability, nanoparticles can improve delivery to membrane barriers, while micelles and liposomes can counter hydrophobicity as they can carry both hydrophilic and hydrophobic molecules [94,116].…”

Section: Discussionmentioning

confidence: 99%

Antiviral Natural Products for Arbovirus Infections

2020

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Over the course of the last 50 years, the emergence of several arboviruses have resulted in countless outbreaks globally. With a high proportion of infections occurring in tropical and subtropical regions where arthropods tend to be abundant, Asia in particular is a region that is heavily affected by arboviral diseases caused by dengue, Japanese encephalitis, West Nile, Zika, and chikungunya viruses. Major gaps in protection against the most significant emerging arboviruses remains as there are currently no antivirals available, and vaccines are only available for some. A potential source of antiviral compounds could be discovered in natural products—such as vegetables, fruits, flowers, herbal plants, marine organisms and microorganisms—from which various compounds have been documented to exhibit antiviral activities and are expected to have good tolerability and minimal side effects. Polyphenols and plant extracts have been extensively studied for their antiviral properties against arboviruses and have demonstrated promising results. With an abundance of natural products to screen for new antiviral compounds, it is highly optimistic that natural products will continue to play an important role in contributing to antiviral drug development and in reducing the global infection burden of arboviruses.

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“…The free radical scavenging activity of nitrones was also determined spectrophotometrically using a previously described method [ 37 , 38 ], with minor modifications. For the spectrophotometric evaluations, nitrones and DPPH solutions were mixed (antioxidant 50 µM, DPPH 100 µM, FC) in two different solvents (methanol and acetonitrile), shaken vigorously and incubated for 30 min and 60 min in the dark.…”

Section: Methodsmentioning

confidence: 99%

Insights into the Antioxidant Mechanism of Newly Synthesized Benzoxazinic Nitrones: In Vitro and In Silico Studies with DPPH Model Radical

et al. 2021

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Synthetic nitrone spin-traps are being explored as therapeutic agents for the treatment of a wide range of oxidative stress-related pathologies, including but not limited to stroke, cancer, cardiovascular, and neurodegenerative diseases. In this context, increasing efforts are currently being made to the design and synthesis of new nitrone-based compounds with enhanced efficacy. The most researched nitrones are surely the ones related to α-phenyl-tert-butylnitrone (PBN) and 5,5-dimethyl-1-pyrroline N-oxide (DMPO) derivatives, which have shown to possess potent biological activity in many experimental animal models. However, more recently, nitrones with a benzoxazinic structure (3-aryl-2H-benzo[1,4]oxazin-N-oxides) have been demonstrated to have superior antioxidant activity compared to PBN. In this study, two new benzoxazinic nitrones bearing an electron-withdrawing methoxycarbonyl group on the benzo moiety (in para and meta positions respect to the nitronyl function) were synthesized. Their in vitro antioxidant activity was evaluated by two cellular-based assays (inhibition of AAPH-induced human erythrocyte hemolysis and cell death in human retinal pigmented epithelium (ARPE-19) cells) and a chemical approach by means of the α,α-diphenyl-β-picrylhydrazyl (DPPH) scavenging assay, using both electron paramagnetic resonance (EPR) spectroscopy and UV spectrophotometry. A computational approach was also used to investigate their potential primary mechanism of antioxidant action, as well as to rationalize the effect of functionalization on the nitrones reactivity toward DPPH, chosen as model radical in this study. Further insights were also gathered by exploring the nitrone electrochemical properties via cyclic voltammetry and by studying their kinetic behavior by means of EPR spectroscopy. Results showed that the introduction of an electron-withdrawing group in the phenyl moiety in the para position significantly increased the antioxidant capacity of benzoxazinic nitrones both in cell and cell-free systems. From the mechanistic point of view, the calculated results closely matched the experimental findings, strongly suggesting that the H-atom transfer (HAT) is likely to be the primary mechanism in the DPPH quenching.

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Monoalkylated Epigallocatechin-3-gallate (C18-EGCG) as Novel Lipophilic EGCG Derivative: Characterization and Antioxidant Evaluation

Cited by 32 publications

References 55 publications

Comparison of Antioxidants: The Limited Correlation between Various Assays of Antioxidant Activity

Comparison of Antioxidants: The Limited Correlation between Various Assays of Antioxidant Activity

Antiviral Natural Products for Arbovirus Infections

Insights into the Antioxidant Mechanism of Newly Synthesized Benzoxazinic Nitrones: In Vitro and In Silico Studies with DPPH Model Radical

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