Biorelevant physicochemical profiling of (E)- and (Z)-resveratrol determined from isomeric mixtures

Orgován, Gábor; Gonda, Imre; Noszál, Béla

doi:10.1016/j.jpba.2016.09.019

Cited by 16 publications

(16 citation statements)

References 30 publications

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“…The synthetic route is in Scheme 1 (see Section 3, Materials and Methods for the detailed procedures). Confirmation of the structures and purity of all compounds were obtained from 1 H and 13 C-NMR and the geometry of the double bond was established by J-values range from 15 to 16 Hz of trans-olefinic proton respect of cis-stilbene olefinic protons from 7.4 to 8.6 Hz reported in literature [51]. The purity of each compounds was evaluated by HPLC-PDA procedure during the Log P analyses (see Supplementary Materials for the detailed procedures), considering the counter plot results and the peak area values corresponding to analyte maximum wavelength.…”

Section: Chemistrymentioning

confidence: 97%

Synthesis and Biological Evaluation of Halogenated E-Stilbenols as Promising Antiaging Agents

et al. 2020

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The increased risk of illness and disability is related to the age inevitable biological changes. Oxidative stress is a proposed mechanism for many age-related diseases. The crucial importance of polyphenol pharmacophore for aging process is largely described thanks to its effects on concentrations of reactive oxygen species. Resveratrol (3,5,4′-trihydroxy-trans-stilbene, RSV) plays a critical role in slowing the aging process but has a poor bioavailabity after oral intake. In this present work, a series of RSV derivatives was designed, synthesized, and evaluated as potential antioxidant agents. These derivatives contain substituents with different electronic and steric properties in different positions of aromatic rings. This kind of substituents affects the activity and the bioavailability of these compounds compared with RSV used as reference compound. Studies of Log P values demonstrated that the introduction of halogens gives the optimum lipophilicity to be considered promising active agents. Among them, compound 6 showed the higher antioxidant activity than RSV. The presence of trifluoromethyl group together with a chlorine atom increased the antioxidant activity compared to RSV.

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Section: Chemistrymentioning

confidence: 97%

Synthesis and Biological Evaluation of Halogenated E-Stilbenols as Promising Antiaging Agents

et al. 2020

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“…Flieger et al (2017) pointed out that when the temperature reached 75°C or above, heating could induce the isomerization of resveratrol from trans-resveratrol to cis-resveratrol even without light. Also, Orgován et al (2017) found that the solubility of cis-resveratrol was over ten times more than that of trans-resveratrol in water as transresveratrol was more lipophilic than its isomer. Thus, a possible explanation for the increase in GAE observed here could be that some of the trans-resveratrol isomerized to cis-resveratrol and that led to an increase in solubility.…”

Section: Total Phenolic Content By Folin-ciocalteu Methodsmentioning

confidence: 99%

“…Also, according to Orgován, Gonda, and Noszál (2017), the trans-resveratrol is more lipophilic than its isomer. Moreover, they also found that the cis-resveratrol has over ten times more solubility than trans-resveratrol.…”

Section: The Effect Of Light On Resveratrol Solubility and Stabilitymentioning

confidence: 99%

Protective effect of β-lactoglobulin against heat induced loss of antioxidant activity of resveratrol

Guo

Jauregi

2018

Food Chemistry

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Resveratrol exhibits many health benefits however, low water-solubility and instability to processing conditions such as heating can be some of the main challenges for its processing and formulation. Here the complexation of -lactoglobulin (-Lg) with resveratrol was investigated to improve its solubility and stability. The solubility of resveratrol in water was determined as 7mg/100ml. Resveratrol--Lg nanoparticles (181.8 nm) were produced at pH 6 and 75°C for 45 min. Heating resveratrol solutions at 75°C for 45 min resulted in isomerization of resveratrol and reduced antioxidant activity. However, resveratrol--Lg nanocomplexes which had undergone the same heat treatment exhibited improved antioxidant activity. Heating at pasteurisation conditions led to similar results and both native -Lg and nanoparticles exhibited a protective effect against heat induced chemical changes in resveratrol resulting in enhanced antioxidant activity. 2 Fluorescence measurements revealed strong interactions of resveratrol with both, native protein and nanoparticles.

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“…CR is less associated with human health, but it exhibits some properties; however, it is much less potent and has less data than TR. [8] RESV is able to activate and regulate the group of NAD +dependent enzymes known as sirtuins (SIRT). According to Grathwol et al, [9] SIRT2 inhibition is thermodynamically favored by E-isomers insofar as the Z-isomers are metastable forms with decreased biological effects due to the photoisomerization by UV radiation (similar Abbreviations: CR, cis-resveratrol; HPLC, high-performance liquid chromatography; HPLC-DAD, high-performance liquid chromatography with diode array detector; LC-MS/MS, liquid chromatography-mass spectrometry; RESV, resveratrol; TR, trans-resveratrol.…”

Section: Introductionmentioning

confidence: 99%

Resveratrol isoforms and conjugates: A review from biosynthesis in plants to elimination from the human body

Riccio

Spósito

Carvalho

et al. 2020

Archiv der Pharmazie

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The natural isomers of resveratrol, cis-and trans-resveratrol, are natural phenolic substances synthetized via the shikimate pathway and found in many sources, including grapes, peanuts, blackberries, pistachios, cacao, cranberries, and jackfruits. They have functional and pharmacological properties such as anticarcinogenic, antidiabetic, anti-inflammatory, and cardioprotective activities. The aim of this article is to review the data published on resveratrol and its isomers, and their biosynthesis in plants, food sources, health and toxic effects, and the excretion of their metabolites. Due to its contribution to the promotion of human health, it is convenient to gather more knowledge about its functional properties, food sources, and the interactions with the human body during the processes of eating, digestion, absorption, biotransformation, and excretion, to combine this information to improve the understanding of these substances.

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Biorelevant physicochemical profiling of (E)- and (Z)-resveratrol determined from isomeric mixtures

Cited by 16 publications

References 30 publications

Synthesis and Biological Evaluation of Halogenated E-Stilbenols as Promising Antiaging Agents

Synthesis and Biological Evaluation of Halogenated E-Stilbenols as Promising Antiaging Agents

Protective effect of β-lactoglobulin against heat induced loss of antioxidant activity of resveratrol

Resveratrol isoforms and conjugates: A review from biosynthesis in plants to elimination from the human body

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