Evaluation of Resveratrol Oxidation<i>in Vitro</i>and the Crucial Role of Bicarbonate Ions

Yang, Nae-Cherng; Lee, Cheng-Hao; Song, Tuzz-Ying

doi:10.1271/bbb.90549

Cited by 50 publications

(52 citation statements)

References 19 publications

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“…These results corroborate widely ignored findings that the stability and oxidation of RSV in physiologically relevant media is strongly influenced by pH and in particular the availability of hydroxyl anions 16,29,32 . Interestingly, RSV reacted also efficiently in tap water (Fig.…”

Section: Rsv Is Unstable Under Physiologically Relevant Conditionssupporting

confidence: 90%

“…S1e). Oxidation of resveratrol at atmospheric oxygen level (21% O 2 , as usually applied in cell culture) 16,29 could potentially be considered as non-physiological (in blood vessels the oxygen amount is roughly 14% and in tissues or tumours even lower (~ 1% O 2 ) 30 . We showed that the auto-oxidation of RSV is highly dependent on the presence of sodium bicarbonate and pH of the solvent 14,31 (see Figure 1 and 2 in Reference 31 ), whereas decreasing oxygen partial pressure seems to have a comparably minor influence on the oxidation efficiency of RSV (see Figure 3 and 4 in reference 31 ).…”

Section: Rsv Is Unstable Under Physiologically Relevant Conditionsmentioning

confidence: 99%

“…Depending on the reaction conditions resveratrol can be (auto-) oxidized to generate semiquinones and the relatively stable 4'-phenoxyl radical, which can produce reactive oxygen species (ROS) 13,14 . (Auto-) oxidative reactions of polyphenols are influenced by changing pH, particularly the presence of hydroxyl anions or organic bases 15,16 . Additionally, metal ions (e.g.…”

Section: Introductionmentioning

confidence: 99%

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Hormetic Shifting of Redox Environment by Pro-Oxidative Resveratrol Protects Cells Against Stress

Plauth

Geikowski

Cichon

et al. 2016

Preprint

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ABSTRACT:Resveratrol has gained tremendous interest owing to multiple reported healthbeneficial effects. However, the underlying key mechanism of action of resveratrol remained largely controversial. Here, we demonstrate that under physiologically relevant conditions major biological effects of resveratrol can be attributed to the generation of oxidation products such as reactive oxygen species (ROS). At low hormetic concentrations (< 50 µM), treatment with resveratrol increased cell viability in a set of representative cell models, whereas application of quenchers of ROS completely truncated these beneficial effects. Notably, application of resveratrol led to mild, Nrf2-specific cellular gene expression reprogramming. For example, in 2 primary human epidermal keratinocytes this resulted in a 1.3-fold increase of endogenous metabolites such as glutathione (GSH) and subsequently in a quantitative reduction of the cellular redox environment by 2.61 mV mmol GSH per g protein.After external application of oxidative stress by using 0.8% (v/v) ethanol, endogenous generation of ROS was consequently reduced by 24% in resveratrol pre-treated cells.In contrast to the common perception that resveratrol acts mainly as a chemical antioxidant or as a target protein-specific ligand, we propose that effects from resveratrol treatment are essentially based on oxidative triggering of cells. In relevant physiological microenvironments this effect can lead to hormetic shifting of cellular defence towards a more reductive state to improve resilience to oxidative stress in a manner that can be exactly defined by the redox-environment of the cell.

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Section: Rsv Is Unstable Under Physiologically Relevant Conditionssupporting

confidence: 90%

Section: Rsv Is Unstable Under Physiologically Relevant Conditionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Hormetic Shifting of Redox Environment by Pro-Oxidative Resveratrol Protects Cells Against Stress

Plauth

Geikowski

Cichon

et al. 2016

Preprint

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show abstract

“…Accordingly, the resulting culture medium after incubation with RSV for 12 hours contained an unexpectedly low level of RSV, and only 1.7% of RSV was recovered from the culture medium (Table 2). Sodium bicarbonate in the culture medium is reported to degrade RSV, and 96% of RSV at a concentration of 200 mM is degraded in base-modified Eagle's medium after 24 hours of incubation (Yang et al, 2010). Thus, extremely low levels of RSV and glycosyl RSVs in the culture medium and cells may be attributed to their degradation by the culture medium.…”

Section: Biological Functions Of Glycosyl Resveratrolsmentioning

confidence: 99%

Differential Cell-Protective Function of Two Resveratrol (Trans-3,5,4′-trihydroxystilbene) Glucosides against Oxidative Stress

Hosoda

Kuno

Hori

et al. 2012

J Pharmacol Exp Ther

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Resveratrol (trans-3,5,49-trihydroxystilbene; RSV), a natural polyphenol, exerts a beneficial effect on health and diseases. RSV targets and activates the NAD 1 -dependent protein deacetylase SIRT1; in turn, SIRT1 induces an intracellular antioxidative mechanism by inducing mitochondrial superoxide dismutase (SOD2). Most RSV found in plants is glycosylated, and the effect of these glycosylated forms on SIRT1 has not been studied. In this study, we compared the effects of RSV and two glycosyl RSVs, resveratrol-3-O-b-D-glucoside (3G-RSV; polydatin/piceid) and resveratrol-49-O-b-D-glucoside (49G-RSV), at the cellular level. In oxygen radical absorbance capacity and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays, the antioxidant activity of 3G-RSV was comparable to that of RSV, whereas the radical-scavenging efficiency of 49G-RSV was less than 50% of that of RSV. However, 49G-RSV, but not 3G-RSV, induced SIRT1-dependent histone H3 deacetylation and SOD2 expression in mouse C2C12 skeletal myoblasts; as with RSV, SIRT1 knockdown blunted these effects. RSV and 49G-RSV, but not 3G-RSV, mitigated oxidative stress-induced cell death in C2C12 cells and primary neonatal rat cardiomyocytes. RSV and 49G-RSV inhibited C2C12 cell proliferation, but 3G-RSV did not. RSV was found in both the intracellular and extracellular fractions of C2C12 cells that had been incubated with 49G-RSV, indicating that 49G-RSV was extracellularly deglycosylated to RSV, which was then taken up by the cells. C2C12 cells did not deglycosylate 3G-RSV. Our results point to 49G-RSV as a useful RSV prodrug with high water solubility. These data also show that the in vitro antioxidative activity of these molecules did not correlate with their ability to protect cells from oxidative stress-induced apoptosis.

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“…[1][2][3] Its effectiveness has been explained by several mechanisms, including increased ATP phosphorylation potential, enhanced sarcoplasmic reticular calcium ion exchange, closure of mitochondrial permeability transition pores, and decreased cytoplasmic NADH/NAD þ ratio (see ref. 4 for a review).…”

mentioning

confidence: 99%

Higher Hypochlorous Acid Scavenging Activity of Ethyl Pyruvate Compared to Its Sodium Salt

Olek

Ziółkowski

Kaczor

et al. 2011

Bioscience, Biotechnology, and Biochemistry

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Evaluation of Resveratrol Oxidationin Vitroand the Crucial Role of Bicarbonate Ions

Cited by 50 publications

References 19 publications

Hormetic Shifting of Redox Environment by Pro-Oxidative Resveratrol Protects Cells Against Stress

Hormetic Shifting of Redox Environment by Pro-Oxidative Resveratrol Protects Cells Against Stress

Differential Cell-Protective Function of Two Resveratrol (Trans-3,5,4′-trihydroxystilbene) Glucosides against Oxidative Stress

Higher Hypochlorous Acid Scavenging Activity of Ethyl Pyruvate Compared to Its Sodium Salt

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