Does resveratrol retain its antioxidative properties in wine? Redox behaviour of resveratrol in the presence of Cu(II) and tebuconazole

Dytrtová, Jana Jaklová; Straka, Michal; Bělonožníková, Kateřina; Jakl, Michal; Ryšlavá, Helena

doi:10.1016/j.foodchem.2018.04.096

Cited by 17 publications

(9 citation statements)

References 20 publications

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“…The structural analogues include (a) double‐charged complexes [ M ( Pen ) 4 ] 2+ , (b) complexes with Cl − as the counterion [ M ( Pen ) 2,3 Cl] + and (c) complexes with deprotonated penconazole [ M ( Pen ) 0,1,2 ( Pen ‐H)] + , where M stands for Cu(II) or Zn(II). For fewer than four neutral Pen ligands, copper is present as reduced Cu(I), which corresponds to the typical Cu behaviour in the electrospray . The M (II)/ Pen / Pen ‐H complexes also include molecules of ethanol or water.…”

Section: Resultsmentioning

confidence: 95%

Complexation and stability of the fungicide penconazole in the presence of zinc and copper ions

Kovač

Jakl

Fanfrlík

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale:For the risk assessment of penconazole in the environment and the evaluation of the possible consequences of its use, it is important to determine how its reactivity and degradation are influenced by metals commonly found in nature, such as copper and zinc. Methods:Changes in the reactivity of penconazole in the presence of zinc/copper ions were studied using electrospray ionisation mass spectrometry and density functional theory calculations.Results: Many penconazole complexes with copper and zinc ions were created; a comparison of the elements showed that a few complexes were formed analogously (doubly charged complexes with four penconazole molecules, singly charged complexes with chlorine as a counterion and singly charged complexes with deprotonated penconazole as a counterion). The metal complexes with different structures indicated different reactivity of penconazole with copper and zinc. Conclusions:The experimental and computational approaches have revealed different changes in the structure of penconazole. In the Zn(II) complex, penconazole deprotonated to stabilise the bond to Zn(II). In the Cu(II) complex, it loses one chlorine atom, creates an additional ring between the triazole ring and the phenyl ring, and/or creates a double bond in the short aliphatic chain.

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Section: Resultsmentioning

confidence: 95%

Complexation and stability of the fungicide penconazole in the presence of zinc and copper ions

Kovač

Jakl

Fanfrlík

et al. 2020

Rapid Comm Mass Spectrometry

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“…The 1 H NMR spectrum of our starting material 1 E-resveratrol (3,5,4'-trihydroxystilbene, C14H12O3) consists of one set of three aromatic hydrogens coupled in an AX2 system (δ 6.54d, 2H, 4 J=2 Hz and δ 6.28t, 1H, 2 Hz), another set of four aromatic hydrogens coupled in an AA′XX′ system (δ 7.24dm, 2H, 3 J=8. 4 Hz and δ 6.79dm, 2H, 8.4 Hz), and two doublet signals (δ 7.03d, 1H, 3 J=16 Hz and δ 6.89d, 1H, 16Hz) indicating the presence of a HC = CH double bond with E configuration [23].…”

Section: Structure Elucidation Of the Isolated Compoundsmentioning

confidence: 99%

“…The complex pharmacology of resveratrol involves its ability to interact with many important enzymes and receptor signaling pathways, and its ability to prevent damage connected to oxidative stress. Resveratrol is known to scavenge a variety of free radicals [4], i.e., reactive oxygen and nitrogen species (ROS and RNS, respectively, collectively referred to as RONS). Such reactive species are normal byproducts of the aerobic metabolism, and, in physiological conditions, their levels are under tight enzymatic control.…”

Section: Introductionmentioning

confidence: 99%

Oxidized Resveratrol Metabolites as Potent Antioxidants and Xanthine Oxidase Inhibitors

Agbadua¹,

Kúsz²,

Berkecz³

et al. 2022

Preprint

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Resveratrol is a well-known natural polyphenol with a plethora of pharmacological activities. As a potent antioxidant, resveratrol is highly oxidizable, and readily reacts with reactive oxygen species (ROS). Such a reaction not only leads to a decrease in ROS levels in a biological environ-ment but may also generate a wide range of metabolites with altered bioactivities. Inspired by this notion, in the current study, our aim was to take a diversity-oriented chemical approach to study the chemical space of oxidized resveratrol metabolites. Chemical oxidation of resveratrol and a bioactivity-guided isolation strategy using xanthine oxidase (XO) and radical scavenging activities led to the isolation of a diverse group of compounds, including a chlorine-substituted compound (2), two iodine-substituted compounds (3 and 4), two viniferins (5 and 6), an eth-oxy-substituted compound (7) two ethoxy-substituted dimers (8 and 9). Compounds 4, 7, 8 and 9 are reported here for the first time. All compounds without ethoxy-substitution exerted stronger XO inhibition than their parent compound, resveratrol. By enzyme kinetic and in silico docking studies compounds 2, 3 and 4 were identified as potent competitive inhibitors of the enzyme while the viniferins acted as mixed-type inhibitors. Further, compounds 2 and 9 had better DPPH scavenging activity and oxygen radical absorbing capacity than resveratrol. Our results suggest that the antioxidant activity of resveratrol is modulated by the effect of a cascade of chemically stable oxidized metabolites, several of which have significantly altered target specificity as compared to their parent compound.

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“…As thoroughly reviewed by Halliwell (2012) [22], flavonoids as antioxidants have failed in the majority of intervention studies to provide any therapeutic benefit and thus have not passed to further phases of clinical trials, let alone used as antioxidants in medical practice. Interestingly, various studies point to a fact that flavonoids might actually act in a pro-oxidant manner in vivo, rather than as antioxidants (such might be the case of resveratrol [23]). Since the human diet may have been relatively rich in flavonoids, humans must have adapted to this evolutionary pressure.…”

Section: Antioxidant Activity Of Flavonoids and Stilbenesmentioning

confidence: 99%

“…Though showing promise in in vitro studies and animal models, resveratrol has failed to provide any significant therapeutic advantage over placebo in human clinical trials of cancer, cardiovascular disorders, metabolic diseases including diabetes and obesity, nor was it shown to have positive effects on longevity [91][92][93][94]. With regard to antioxidant activity, various studies have pointed out that resveratrol behaves as a strong pro-oxidant in vivo [23,95]. Other problems that hinder its clinical use is its poor water solubility and high rate of metabolism and excretion [96].…”

Section: Stilbenesmentioning

confidence: 99%

Flavonoids and Related Members of the Aromatic Polyketide Group in Human Health and Disease: Do They Really Work?

et al. 2020

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Some aromatic polyketides such as dietary flavonoids have gained reputation as miraculous molecules with preeminent beneficial effects on human health, for example, as antioxidants. However, there is little conclusive evidence that dietary flavonoids provide significant leads for developing more effective drugs, as the majority appears to be of negligible medicinal importance. Some aromatic polyketides of limited distribution have shown more interesting medicinal properties and additional research should be focused on them. Combretastatins, analogues of phenoxodiol, hepatoactive kavalactones, and silymarin are showing a considerable promise in the advanced phases of clinical trials for the treatment of various pathologies. If their limitations such as adverse side effects, poor water solubility, and oral inactivity are successfully eliminated, they might be prime candidates for the development of more effective and in some case safer drugs. This review highlights some of the newer compounds, where they are in the new drug pipeline and how researchers are searching for additional likely candidates.

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Does resveratrol retain its antioxidative properties in wine? Redox behaviour of resveratrol in the presence of Cu(II) and tebuconazole

Cited by 17 publications

References 20 publications

Complexation and stability of the fungicide penconazole in the presence of zinc and copper ions

Complexation and stability of the fungicide penconazole in the presence of zinc and copper ions

Oxidized Resveratrol Metabolites as Potent Antioxidants and Xanthine Oxidase Inhibitors

Flavonoids and Related Members of the Aromatic Polyketide Group in Human Health and Disease: Do They Really Work?

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