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

Antioxidants
Cristina MinnelliGiovanna Mobbili

Abstract

Epigallocatechin-3-gallate (EGCG) has the highest antioxidant activity compared to the others catechins of green tea. However, the beneficial effects are mainly limited by its poor membrane permeability. A derivatization strategy to increase the EGCG interaction with lipid membranes is considered as one feasible approach to expand its application in lipophilic media, in particular the cellular absorption. At this purpose the hydrophilic EGCG was modified by inserting an aliphatic C18 chain linked to the gallate ring by an ethereal bond, the structure determined by NMR (Nuclear Magnetic Resonance) and confirmed by Density Functional Theory (DFT) calculations. The in vitro antioxidant activity of the mono-alkylated EGCG (C18-EGCG) was studied by the DPPH and Thiobarbituric Acid Reactive Substances (TBARS) assays, and its ability to protect cells towards oxidative stress was evaluated in Adult Retinal Pigmented Epithelium (ARPE-19) cells. Molecular Dynamics (MD) simulation and liposomal/buffer partition were used to study the interaction of the modified and unmodified antioxidants with a cell membrane model: the combined experimental-in silico approach shed light on the higher affinity of C18-EGCG toward lipid bilayer. Although th...Continue Reading

References

Jan 30, 1991·Biochimica Et Biophysica Acta·R C MacDonaldL R Hu
Oct 28, 1994·Biochemical and Biophysical Research Communications·M InoueY Yabu
Feb 1, 1996·Journal of Molecular Graphics·W HumphreyK Schulten
Jul 2, 1998·Bioscience, Biotechnology, and Biochemistry·T NakayamaK Hashimoto
Dec 28, 1999·Bioscience, Biotechnology, and Biochemistry·F NanjoY Hara
Sep 20, 2000·Journal of Agricultural and Food Chemistry·K KidaY Hara
Feb 15, 2001·Journal of Agricultural and Food Chemistry·Z ChenY Huang
Feb 18, 2003·Critical Reviews in Food Science and Nutrition·Jane V Higdon, Balz Frei
Mar 12, 2003·Mutation Research·Joshua D Lambert, Chung S Yang
Apr 1, 2003·Journal of Computational Chemistry·Maurizio CossiVincenzo Barone
Sep 13, 2003·The Journal of Pharmacology and Experimental Therapeutics·Jaya Bharathi Vaidyanathan, Thomas Walle
Jan 1, 1965·Journal of the American Oil Chemists' Society·W S SINGLETONJ L WHITE
Oct 2, 2003·The Journal of Nutrition·Balz Frei, Jane V Higdon
Jul 15, 2004·Toxicology in Vitro : an International Journal Published in Association with BIBRA·S AzamS M Hadi
Jul 21, 2004·Journal of Computational Chemistry·Eric F PettersenThomas E Ferrin
Oct 4, 2005·Journal of Computational Chemistry·David A CaseRobert J Woods
Feb 3, 2009·Biophysical Journal·Yen SunHuey W Huang
Jun 9, 2009·International Journal of Pharmaceutics·A BarrasN Monfilliette-Dupont
Nov 17, 2009·The Journal of Physical Chemistry. a·Claudia Zavala-OsegueraAnnia Galano
Apr 27, 2010·The Journal of Physical Chemistry. B·Annia GalanoJosé Pedraza-Chaverri
May 26, 2010·The Journal of Physical Chemistry. B·Jeffery B KlaudaRichard W Pastor
May 14, 2011·Physical Chemistry Chemical Physics : PCCP·Annia GalanoJ Raúl Alvarez-Idaboy
Feb 7, 2012·Mini Reviews in Medicinal Chemistry·H M Hügel, N Jackson
Aug 15, 2012·Redox Report : Communications in Free Radical Research·Yannis V SimosAngelos M Evangelou
May 8, 2014·Journal of Chemical Theory and Computation·Callum J DicksonRoss C Walker
Jul 30, 2015·BMC Complementary and Alternative Medicine·Simon Bernard Iloki-AssangaJosé Luis Rubio-Pino
Jul 20, 2017·Physical Chemistry Chemical Physics : PCCP·Takahisa MatsuzakiMotomu Tanaka
Feb 22, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Emiliano LaudadioRoberta Galeazzi
Oct 13, 2018·Food Chemistry·Bingbing Liu, Weidong Yan
Mar 21, 2019·Oxidative Medicine and Cellular Longevity·Simona BungauKazuaki Kadonosono

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Citations

Jun 21, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Vanessa Shi Li GohJustin Jang Hann Chu
Jul 28, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Katarzyna NaparłoIzabela Sadowska-Bartosz
Feb 16, 2021·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Namratha Turuvekere Vittala MurthyHarsh Chauhan
Jul 3, 2021·International Journal of Molecular Sciences·Rosalba SiracusaRosanna Di Paola

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Methods Mentioned

BETA
NMR
column chromatography
size exclusion chromatography
gel filtration
nuclear magnetic resonance

Software Mentioned

Gaussian
SigmaPlot
GROMACS
CHIMERA
VMD
Charmm
GUI

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