Antioxidant Activity of Resveratrol Diastereomeric Forms Assayed in Fluorescent-Engineered Human Keratinocytes

Abstract

Resveratrol is a powerful antioxidant molecule. In the human diet, its most important source is in Vitis vinifera grape peel and leaves. Resveratrol exists in two isoforms, cis- and trans. The diastereomeric forms of many drugs have been reported as affecting their activity. The aim of this study was to set up a cellular model to investigate how far resveratrol could counteract cytotoxicity in an oxidant agent. For this purpose, a keratinocyte cell line, which was genetically engineered with jelly fish green fluorescent protein, was treated with the free radical promoter Cumene hydroperoxide. The antioxidant activity of the trans-resveratrol and its diastereomeric mixture was evaluated indirectly in these treated fluorescent-engineered keratinocytes by analyzing the cell number and cell proliferation index. Our results demonstrate that cells, which were pre-incubated with resveratrol, reverted the oxidative damage progression induced by this free radical agent. In conclusion, fluorescent-engineered human keratinocytes represent a rapid and low-cost cellular model to determine cell numbers by studying emitted fluorescence. Comparative studies carried out with fluorescent keratinocytes indicate that trans-resveratrol is more efficient than diastereomeric mixtures in protecting cells from the oxidative stress.

Can l‐ascorbic acid and trans‐resveratrol protect HaCaT cells from fine particulate matter toxicity?

“…17 In vitro studies showed that resveratrol could maintain cellular redox homeostasis and sustain MMP 17 by preventing excessive ROS production. 17 The antioxidant was also found to inhibit PM-induced inflammatory responses in human keratinocytes by suppressing the activation of PM-induced aryl hydrocarbon receptor and reduction of cyclooxygenase-2/prostaglandin 2 and cytokine expression. 14 l-ascorbic acid, being the most biologically active form of vitamin C, is a prototypical antioxidant capable of neutralizing superoxide anion, hydroxyl radical, singlet oxygen, and peroxynitrite.…”

“…Resveratrol (3,4′,5‐trihydroxystilbene) is a polyphenolic compound found in the skin and seeds of grapes, nuts, fruits, and red wine. Due to the presence of three hydroxyl groups in its structure, resveratrol is an efficient antioxidant demonstrating an inhibitory effect on excessive ROS production, aberrant mitochondrial distribution, and lipid peroxidation 17 . In vitro studies showed that resveratrol could maintain cellular redox homeostasis and sustain MMP 17 by preventing excessive ROS production 17 .…”

Resveratrol and Curcumin for Chagas Disease Treatment—A Systematic Review

“…Resveratrol (RVT) is the polyphenol 3,5,4’-trihydroxy- trans -stilbene, a natural compound isolated from the peel of grapes and well known for possessing several beneficial effects to health [ 34 , 35 ], such as anti-inflammatory [ 36 , 37 ] and antioxidant activities [ 38 ], action against chronic diseases, including cardiovascular diseases [ 39 , 40 , 41 ], hypertension [ 42 ], kidney diseases [ 43 ], diabetes mellitus [ 44 ], obesity [ 45 ], neurodegenerative diseases (Parkinson’s, Huntington’s, and Alzheimer’s disease) [ 46 , 47 , 48 , 49 , 50 , 51 ], cancer (breast, colorectal, and multiple myeloma) [ 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 ], and antiviral [ 61 , 62 , 63 ] and antibacterial activity [ 64 , 65 ]. This variety of effects of RVT is attributed to its interactions and modulations with several biological targets in a complex mechanism, lowering the expression of inflammation markers, including inflammatory cytokines, tumor necrosis factor α (TNF-α), nuclear factor-κB (NF-κB), cyclooxygenase 2 (COX-2), a vascular endothelial growth factor (VEGF), an intercellular adhesion molecule (ICAM), a vascular cell adhesion molecule (VCAM), insulin-like growth factor 1 (IGF-1), insulin-like growth factor-binding protein (IGFBP-3), matrix metalloproteinases (MMPs), 5′-AMP-activated protein kinase (AMPK), caspases, and others, and acting as a multi-target compound [ 34 , 35 , 36 , 37 ,…”

Total Syntheses, Absolute Configurations, and Cytotoxicity Evaluation of Ugonstilbenes A, B, and C from the Rhizomes of Helminthostachys zeylanica

“…Until recently no total syntheses of 1 – 3 have been reported, and their absolute configurations have not yet been determined. Naturally occurring stilbenes and synthesized analogues have been reported to have various biological activities including antioxidant, , anti-inflammatory, , cytotoxic, − cardioprotective, , and neuroprotective effects. , They have potential as novel therapeutic agents. This study aimed to stereoselectively synthesize ugonstilbenes A, B, and C in order to further study their biological activities.…”

“…Benzyl phosphonate (24) could be obtained from commercially available 4-hydroxybenzaldehyde via protection to MOM ether, reduction to benzyl alcohol, transformation to benzyl bromide, and finally reaction with triethyl phosphite (P-(OEt) 3 ). Similarly, benzyl phosphonate (29) could be obtained from commercially available 3,5-dihydroxybenzoic acid via esterification to a methyl ester, protection to MOM ether, reduction to benzyl alcohol, transformation to benzyl bromide, and finally reaction with P(OEt) 3 . 19 The starting 4-bromo-3,5-dihydroxybenzioic acid was esterified with MeOH in the presence of 3 N HCl under reflux to afford methyl ester 6, which was converted to 7 by protection of the hydroxy groups with MOMCl.…”