Spectroscopic study on the interaction of resveratrol and pterostilbene with human serum albumin

Nair, Maya S.

doi:10.1016/j.jphotobiol.2015.05.001

Cited by 60 publications

(17 citation statements)

References 40 publications

(46 reference statements)

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“…The poor bioavailability of free trans-resveratrol depends not only on the high first-pass metabolism but also on its elevated protein binding. Albumin, indeed, seems to play a key role in establishing resveratrol-albumin complexes, thus concurring to 98.3% protein binding rate [35][36][37]. Interestingly the gut microbiota was another active major player in the metabolic pathway of resveratrol ( Figure 4).…”

Section: Physico-chemical and Pharmacokinetic Properties Of Resveratrolmentioning

confidence: 90%

Resveratrol in Cancer Patients: From Bench to Bedside

Berretta

Bignucolo

Francia

et al. 2020

IJMS

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Resveratrol (3,5, is a natural phytoalexin that accumulates in several vegetables and fruits like nuts, grapes, apples, red fruits, black olives, capers, red rice as well as red wines. Being both an extremely reactive molecule and capable to interact with cytoplasmic and nuclear proteins in human cells, resveratrol has been studied over the years as complementary and alternative medicine (CAM) for the therapy of cancer, metabolic and cardiovascular diseases like myocardial ischemia, myocarditis, cardiac hypertrophy and heart failure. This review will describe the main biological targets, cardiovascular outcomes, physico-chemical and pharmacokinetic properties of resveratrol in preclinical and clinical models implementing its potential use in cancer patients.properties of resveratrol are, however, marked by a pharmacokinetic profile and by an unfavorable oral bioavailability, which requires a thorough analysis. To date, to the best of our knowledge, scientific papers and reviews summarizing multiple characteristics of resveratrol, its pharmacokinetic, pharmacodynamic profiles and potential drug interaction in oncology are lacking in literature. Therefore, this review aimed to describe the potential use of resveratrol in cancer management presenting the main biochemical pathways involved, issues and potential uses in cancer patients. Moreover, the involvement of resveratrol in cardioncology, its potential use for risk reduction of myocardial ischemia, myocarditis, cardiac hypertrophy as well as heart failure are also discussed. To endorse this review, we made a comprehensive search on PubMed, Web of Science and SciFinder. The search terms were "resveratrol" combined with "cardioncology" or "cancer" or "drug-food" or "cardiology" or "pharmacokinetic" or "pharmacodynamic". Physico-Chemical and Pharmacokinetic Properties of ResveratrolResveratrol is a low molecular weight phyto-polyphenol of 228 Da that appears as an off-white powder with lipophilic properties (octanol/water partition coefficient, log Kow = 3.1). Its melting point is between 253 and 255 • C, and its solubility in water is very low (3 mg/100 mL) [8]. The ethylene bridge due to a limited degree of freedom generates two geometric isomers: cis-resveratrol and trans-resveratrol ( Figure 1) [5]. These isoforms co-exist in resveratrol extracts even if a greater biological activity and stability are attributed to trans-resveratrol. Comparing to the geometric isomers, the nearly planar structure of trans-resveratrol is less flexible than the non-planar structure of cis-resveratrol, but it possesses a lower repulsive energy that ensures it, albeit small, higher stability. Isomerization of trans-resveratrol to cis-resveratrol occurs via molecule breakdown when trans-resveratrol is exposed to UV radiation at a wavelength of 254 or 366 nm, to high pH conditions or in plants during fermentation processes [5,9]. In analyzing some physical-chemical aspects of resveratrol, Zupancic et al. showed how trans-resveratrol is rapidly degradable in high-pH solutions. In par...

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Section: Physico-chemical and Pharmacokinetic Properties Of Resveratrolmentioning

confidence: 90%

Resveratrol in Cancer Patients: From Bench to Bedside

Berretta

Bignucolo

Francia

et al. 2020

IJMS

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“…S2e left), which might explain further the often-reported perplexing low bioavailability of RSV in vivo [33][34][35] . Although RSV could potentially be protected from protein carriers such as serum albumin 36 , the entirety of these data makes it difficult to understand how RSV could exert compound-protein specific effects. These results further indicate that potential metabolisation of RSV, for example by oxidation of the enzymes of the CYP1 family, might play a minor role in physiological context, consistent with the usually extremely low amounts of detected metabolites of resveratrol [33][34][35] .…”

Section: Rsv Is Unstable Under Physiologically Relevant Conditionsmentioning

confidence: 99%

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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“…The fluorescence is an interesting method to characterize the interaction between resveratrol and protein [29,32,33,51]. The BSA contains 2 Trp residues.…”

Section: 7fluorescence Spectroscopymentioning

confidence: 99%

“…Indeed, several molecules can be bound to the hydrophobic pocket of albumin with an affinity constant around 2.10 4 M -1 or 5.10 4 M -1 . This binding occurs via both hydrophillic and hydrophobic interactions and/or hydrogen bonding [30,32,33].…”

Section: Introductionmentioning

confidence: 99%

Going through the wine fining: Intimate dialogue between organics and clays

Trigueiro

Pedetti

Rigaud

et al. 2018

Colloids and Surfaces B: Biointerfaces

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Wine chemistry inspires and challenges with its complexity and intriguing composition. In this context, the composites based on the use of a model protein, a polyphenol of interest and montmorillonite in a model hydroalcoholic solution have been studied. A set of experimental characterization techniques highlighted the interactions between the organic and the inorganic parts in the composite. The amount of the organic part was determined by ultraviolet-visible (UV-VIS) and thermal analysis. X-ray diffraction (XRD) and transmission electronic microscopy (TEM) informed about the stacking/exfoliation of the layers in the composites. Vibrational and nuclear magnetic resonance spectroscopies methods stressed on the formation of a complex between the protein and the polyphenol before adsorption on the clay mineral. The mobility/rigidity of the organic parts were determined by fluorescence time resolved spectroscopy. Changes in the secondary structure of the protein occured upon complexation with polyphenol on clay mineral due to strong interactions. Although not representating faithfully enological conditions, these results highlight the range and nature of mechanisms possibly involved in wine fining.

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Spectroscopic study on the interaction of resveratrol and pterostilbene with human serum albumin

Cited by 60 publications

References 40 publications

Resveratrol in Cancer Patients: From Bench to Bedside

Resveratrol in Cancer Patients: From Bench to Bedside

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

Going through the wine fining: Intimate dialogue between organics and clays

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