A theoretical study of the structure–radical scavenging activity of trans-resveratrol analogues and cis-resveratrol in gas phase and water environment

Mikulski, Damian; Gorniak, Rafal; Molski, Marcin

doi:10.1016/j.ejmech.2009.11.044

Cited by 99 publications

(63 citation statements)

References 19 publications

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“…Hence, the geometries of t-RES and t-PIC deviate strongly from planarity. This result does not correlate with DFT calculations performed previously [25][26][27]. The MP2 finding obtained for t-RES in this study is in good agreement with previous HF computations.…”

Section: Geometry Analysis Of T-res and T-picsupporting

confidence: 93%

Quantum-mechanical computations on the electronic structure of trans-resveratrol and trans-piceatannol: a theoretical study of the stacking interactions in trans-resveratrol dimers

Mikulski

Molski

2012

J Mol Model

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Accurate quantum-chemical calculations based on the second-order Møller-Plesset perturbation method (MP2) and density functional theory (DFT) were performed for the first time to investigate the electronic structures of trans-resveratrol and trans-piceatannol, as well as to study the stacking interaction between trans-resveratrol molecules. Ab initio MP2 calculations performed with using standard split-valence Pople basis sets led us to conclude that these compounds have structures that deviate strongly from planarity, whereas the DFT computations for the same basis sets revealed that the equilibrium geometries of these bioactive polyphenols are planar. Furthermore, the results obtained at the MP2(full)/aug-cc-pVTZ and B3LYP/aug-cc-pVTZ levels indicated that the geometries of trans-resveratrol and trans-piceatannol are practically planar at their absolute energy minima. The relative energies of the equilibrium geometries of trans-resveratrol on its potential energy surface were computed at the MP2(full)/aug-cc-pVTZ level. According to the results obtained, a T-shaped (edge-to-phase) conformer of trans-resveratrol dimer is the most stable in vacuum. This T-shaped conformer is mainly stabilized by strong hydrogen bonding and weak C-H...π interactions. Stacked structures with parallel-displaced trans-stilbene skeletons were also found to be energetically stable. The vertical separation and twist angle dependencies of the stacking energy were investigated at the MP2(full)/aug-cc-pVTZ, B3LYP/aug-cc-pVTZ, and HF/aug-cc-pVTZ levels. The standard B3LYP functional and the Hartree-Fock method neglect long-range attractive dispersion interactions. The MP2 computations revealed that the London dispersion energy cannot be neglected at long or short distances. The stacked model considered here may be useful for predicting the quantum nature of the interactions in π-stacked systems of other naturally occurring stilbenoids, and can help to enhance our understanding of the antioxidant and anticancer activities of trans-resveratrol.

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Section: Geometry Analysis Of T-res and T-picsupporting

confidence: 93%

Quantum-mechanical computations on the electronic structure of trans-resveratrol and trans-piceatannol: a theoretical study of the stacking interactions in trans-resveratrol dimers

Mikulski

Molski

2012

J Mol Model

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“…ACCEPTED MANUSCRIPT 6 addition, a resveratrol-induced increase in eNOS expression has been attenuated by knockingdown endogenous SIRT1 levels by RNAi [52], and thus it appears that SIRT1 activation by resveratrol mediates both activity and expression of eNOS. AMPK, a major regulator of energy metabolism [53], also regulates NO bioavailability via eNOS.…”

Section: Accepted Manuscriptmentioning

confidence: 97%

“…Resveratrol is considered a phytoalexin, because it is produced by the plant under stress conditions [5]. Although resveratrol exists in either the cis or trans form, it is the trans isomer that is a more effective anti-oxidant [6], is more bioactive [7], and more stable [7,8]. The presence of resveratrol, along with other polyphenolic compounds in red wine has garnered much attention, especially with regards to their potential role in the protection against CVD [9].…”

Section: Introductionmentioning

confidence: 98%

Preclinical and clinical evidence for the role of resveratrol in the treatment of cardiovascular diseases

Zordoky

Robertson

Dyck

2015

Biochimica et Biophysica Acta (BBA) - Molecular Basis of Diseas

275

217

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Cardiovascular disease is the leading cause of death worldwide. Despite advancements in diagnosis and treatment of cardiovascular disease, the incidence of cardiovascular disease is still rising. Therefore, new lines of medications are needed to treat the growing population of patients with cardiovascular disease. Although the majority of the existing pharmacotherapies for cardiovascular disease are synthesized molecules, natural compounds, such as resveratrol, are also being tested. Resveratrol is a non-flavonoid polyphenolic compound, which has several biological effects. Preclinical studies have provided convincing evidence that resveratrol has beneficial effects in animal models of hypertension, atherosclerosis, stroke, ischemic heart disease, arrhythmia, chemotherapy-induced cardiotoxicity, diabetic cardiomyopathy, and heart failure. Although not fully delineated, some of the beneficial cardiovascular effects of resveratrol are mediated through activation of silent information regulator 1 (SIRT1), AMP-activated protein kinase (AMPK), and endogenous anti-oxidant enzymes. In addition to these pathways, the anti-inflammatory, anti-platelet, insulin-sensitizing, and lipid-lowering properties of resveratrol contribute to its beneficial cardiovascular effects. Despite the promise of resveratrol as a treatment for numerous cardiovascular diseases, the clinical studies for resveratrol are still limited. In addition, several conflicting results from trials have been reported, which demonstrates the challenges that face the translation of the exciting preclinical findings to humans. Herein, we will review much of the preclinical and clinical evidence for the role of resveratrol in the treatment of cardiovascular disease and provide information about the physiological and molecular signaling mechanisms involved. This article is part of a Special Issue entitled: Resveratrol: Challenges in translating pre-clinical findings to improved patient outcomes.

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“…Although cis-resveratrol was proved to be less efficient as an antioxidant than trans-resveratrol (Belguendouz, Fremont, & Linard, 1997;Mikulski, Górniak, & Molski, 2010), many other beneficial properties of the former and the related cis-stilbenes were also reported (Leiro et al, 2005;Pettit et al, 2002;Siemann, Chaplin, & Walicke, 2009). For example, Leiro's studies (Leiro et al, 2005) showed cis-resveratrol has anti-inflammatory properties through a significant modulatory effect on the nuclear factor jB related genes.…”

Section: Introductionmentioning

confidence: 94%

Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues

et al. 2012

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A theoretical study of the structure–radical scavenging activity of trans-resveratrol analogues and cis-resveratrol in gas phase and water environment

Cited by 99 publications

References 19 publications

Quantum-mechanical computations on the electronic structure of trans-resveratrol and trans-piceatannol: a theoretical study of the stacking interactions in trans-resveratrol dimers

Quantum-mechanical computations on the electronic structure of trans-resveratrol and trans-piceatannol: a theoretical study of the stacking interactions in trans-resveratrol dimers

Preclinical and clinical evidence for the role of resveratrol in the treatment of cardiovascular diseases

Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues

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