ChemInform Abstract: Structure—Activity Relationship of trans‐Resveratrol and Its Analogues.

Ovesná, Z; Horvathova‐Kozics, K.

doi:10.1002/chin.200828249

Cited by 31 publications

(36 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Например, катехольная группа играет ключевую роль в противорадикальной активности [7], и, в нашем случае, обеспечивает более эффективное образование [M -2H] -и H 2 в пицеатанноле. Последний, действи-тельно, является более эффективным антиоксидантом, чем ресвератрол [44][45][46][47], несмотря на то, что наблюдае-мые эффекты полифенольных соединений в организме очень многогранны, и определяются множеством факто-ров, как например, биодоступностью и эффективностью усвоения.…”

Section: Discussionunclassified

Resonance electron attachment to natural polyphenolic compounds and their biological activity

Pshenichnyuk¹,

Asfandiarov²,

Воробьев³

et al. 2015

LoM

View full text Add to dashboard Cite

Resonance low-energy (0-14 eV) electron attachment to natural polyphenolic stilbenes possessing antioxidant properties, namely resveratrol and piceatannol, was investigated by means of dissociative electron attachment spectroscopy. Experimental findings were assigned on base of density functional theory (DFT) calculations of energies and symmetry of vacant molecular orbitals. It was found that characteristic decay of the molecular negative ions of compounds under investigation under gasphase conditions can be associated with elimination of neutral H 2 molecule and formation of quinone-like structure bearing excess electron. These fragment species can be responsible for ability of polyphenolic compounds to scavenge free radicals in the living cells. The gas-phase data were extrapolated to reactions in cellular environment by means of DFT calculations using polarizable continuum model approach. A molecular mechanism for antioxidant activity of polyphenolic compounds in proximity to the mitochondrial respiratory chain under conditions of excess negative charge was suggested. Namely, it is thought that molecular hydrogen, known for its selective antioxidant properties, can be efficiently generated via attachment of electrons ("leaked" from the respiratory chain into mitochondrial intermembrane space) to polyphenolic compound and may be responsible for its antioxidant activity. The corresponding negative fragment, i.e., quinone bearing an excess negative charge, can serve as electron carrier and can return the captured electron back to the respiration cycle. The number of hydroxyl substituents and their relative positions on aromatic rings of polyphenolic molecule are crucial for the present molecular mechanism, because these properties determine dissociative electron attachment cross-section.

show abstract

Section: Discussionunclassified

Resonance electron attachment to natural polyphenolic compounds and their biological activity

Pshenichnyuk¹,

Asfandiarov²,

Воробьев³

et al. 2015

LoM

View full text Add to dashboard Cite

show abstract

“…Thus it was suggested that the cytotoxicity of Pte and its analogues depends significantly on the structural determinants, which are double bond and methylated phenolic hydroxyl (Supplementary Fig. 1: a and e) (34). Therefore Pte can serve as a lead compound to derive other analogues with higher therapeutic efficacy.…”

Section: Discussionmentioning

confidence: 99%

Involvement of the Nrf2 Pathway in the Regulation of Pterostilbene-Induced Apoptosis in HeLa Cells via ER Stress

et al. 2014

View full text Add to dashboard Cite

Abstract. Among the various cancer cell lines, HeLa cells were found to be sensitive to pterostilbene (Pte), a compound that is enriched in small fruits such as grapes and berries. However, the mechanism involved in the cytotoxicity of Pte has not been fully characterized. Using biochemical and free radical biological experiments in vitro, we identified the pro-apoptotic profiles of Pte and evaluated the level of redox stress-triggered ER stress during HeLa cell apoptosis. The data showed a strong dose-response relationship between Pte exposure and the characteristics of HeLa apoptosis in terms of changes in apoptotic morphology, DNA fragmentation, and activated caspases in the intrinsic apoptotic pathway. During drug exposure, alterations in the intracellular redox homeostasis that favor oxidation were necessary to cause ER stressrelated apoptosis, as demonstrated by enzymatic and non-enzymatic redox modulators. A statistically significant and dose-dependent increase (P < 0.05) was found with regard to the unique expression levels of Nrf2/ARE downstream target genes in HeLa cells undergoing late apoptosis, levels that were restored with anti-oxidant application with the Pte treatment. Our research demonstrated that Pte trigged ER stress by redox homeostasis imbalance, which was negatively regulated by a following activation of Nrf2.[ Supplementary Figure and Table: available only at http://dx

show abstract

“…The following elements of a compound chemical structure have the essential meaning for the biological activity of RSV and its derivatives; the number and position of hydroxyl groups, the presence of intramolecular hydrogen bonds, spatial isomerism and double bonds [28].…”

Section: The Resveratrol Analoguesmentioning

confidence: 99%

Resveratrol and Its Analogues – Is It a New Strategy of Anticancer Therapy?

Borys

Khozmi

Kranc

et al. 2017

Advances in Cell Biology

View full text Add to dashboard Cite

Summary: Resveratrol (RSV) is one of the polyphenols -metabolites common in plants,however it does not occur in animals. It occurs mainly in grape skin (Vitisvinifera), peanuts (Arachis hypogeal) and in the roots of (Polygonumcupidatum) a traditional Chinese curative plant. RSV has a preventive property against the most serious diseases of modern world such as cancer, neurodegenerative diseases and cardiovascular diseases. Due to pleiotropy, RSV is currently the main object of many research teams' interest, which is shown by the significant number of publications devoted to this subject. Animal and human conducted studies have shown very low bioavailability of RSV (approx. 2%), which is the result of rapid biotransformation to sulphate and to a lesser extent, to the glucuronide conjugates as well. The studies on the improvement of RSV bioavailability, which have beencarried out for many years, have contributed to the synthesis of the analogues of more chemopreventive and more desirable pharmacokinetic properties. In order to enhance antiproliferative activity and RSV bioavailability, series of methyl analogues were synthesized and this will be described later in more detail. An example of such a derivative is 4,

show abstract

ChemInform Abstract: Structure—Activity Relationship of trans‐Resveratrol and Its Analogues.

Cited by 31 publications

References 0 publications

Resonance electron attachment to natural polyphenolic compounds and their biological activity

Resonance electron attachment to natural polyphenolic compounds and their biological activity

Involvement of the Nrf2 Pathway in the Regulation of Pterostilbene-Induced Apoptosis in HeLa Cells via ER Stress

Resveratrol and Its Analogues – Is It a New Strategy of Anticancer Therapy?

Contact Info

Product

Resources

About