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

Antioxidants

Pierluigi Stipa¹  Emiliano Laudadio¹  Tatiana Armeni²  Adolfo Amici²  Roberta Galeazzi³  Mattia Cantarini³  Cristina Minnelli³  Giovanna Mobbili³  Dario Rusciano⁴ 

[1] Department S.I.M.A.U., Università Politecnica delle Marche, via Brecce Bianche, 60131 Ancona, Italy;Department of Clinical Sciences, Section of Biochemistry, Biology and Physics, Università Politecnica delle Marche, via Brecce Bianche, 60131 Ancona, Italy;Department of Life and Environmental Sciences, Università Politecnica delle Marche, via Brecce Bianche, 60131 Ancona, Italy;Sooft Italy SpA, 95100 Catania, Italy;

关键词: epigallocatechin-3-gallate;    antioxidants;    oxidative stress;    molecular dynamics (md) simulation;    free radicals;   

DOI  :  10.3390/antiox9030208

来源: DOAJ

【 摘 要 】

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 the DPPH assay stated that the functionalization decreases the EGCG activity against free radicals, from cellular experiments it resulted that the lipid moiety increases the antioxidant protection of the new lipophilic derivative.

【 授权许可】

Unknown