Syntheses of Resveratrol and its Hydroxylated Derivatives as Radical Scavenger and Tyrosinase Inhibitor

Lee, Hyun Suck; Lee, Byung Won; Kim, Mi Ran; Jun, Jong‐Gab

doi:10.5012/bkcs.2010.31.04.971

Cited by 26 publications

(15 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The analytical thin-layer chromatography (TLC) was conducted on Supelco TLC plates (silica gel 60 F 254 , aluminum foil). Structural characterizations of the various stilbenoid derivatives mentioned above are detailed in the Supplementary materials and are in accordance with literature reports [22][23][24][25][26][27][28][29].…”

Section: Chemistrysupporting

confidence: 81%

Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological Activity and Molecular Modelling Evidence for Cooperativity between Viniferin Enantiomers

et al. 2019

View full text Add to dashboard Cite

To improve the current understanding of the role of stilbenoids in the management of diabetes, the inhibition of the pancreatic α-amylase by resveratrol derivatives was investigated. To approach in a systematic way, the mechanistic and structural aspects of the interaction, potential bioactive agents were prepared as single molecules, that were used for the biological evaluation of the determinants of inhibitory binding. Some dimeric stilbenoids—in particular, viniferin isomers— were found to be better than the reference drug acarbose in inhibiting the pancreatic α-amylase. Racemic mixtures of viniferins were more effective inhibitors than the respective isolated pure enantiomers at an equivalent total concentration, and displayed cooperative effects not observed with the individual enantiomers. The molecular docking analysis provided a thermodynamics-based rationale for the measured inhibitory ability and for the observed synergistic effects. Indeed, the binding of additional ligands on the surface of the alpha-amylase was found to decrease the dissociation constant of inhibitors bound to the active site of the enzyme, thus providing a mechanistic rationale for the observed inhibitory synergies.

show abstract

Section: Chemistrysupporting

confidence: 81%

Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological Activity and Molecular Modelling Evidence for Cooperativity between Viniferin Enantiomers

et al. 2019

View full text Add to dashboard Cite

show abstract

“…1 H- and 13 C-NMR spectroscopic data are provided in Table 2. Based on these data and comparison with literature values [22], compound X was identified to be resveratrol. Cochromatography of purified compound X and authentic resveratrol on a TLC plate further verified this identification (Figure 3(c)).…”

Section: Resultsmentioning

confidence: 89%

Isolation of Resveratrol from Vitis Viniferae Caulis and Its Potent Inhibition of Human Tyrosinase

Park

Boo

2013

Evidence-Based Complementary and Alternative Medicine

View full text Add to dashboard Cite

Tyrosinase (TYR) catalyzes rate-limiting reactions of cellular melanin synthesis, and its inhibitors are of commercial interest as potential skin whitening agents. However, the limited availability of human TYR makes the screening of TYR inhibitors difficult. To overcome this hurdle, we transformed nonmelanocytic human embryonic kidney (HEK) 293 cells to express human TYR constitutively. Using these cells as a source of human TYR, the ethanolic extracts of 52 medicinal plants grown in Korea were tested for human TYR activity, and the extract of Vitis Viniferae Caulis (dried stems of the grape tree, Vitis vinifera L.) was found to inhibit human TYR activity potently. An active compound was isolated from this extract by solvent fractionation followed by liquid column chromatography and identified as resveratrol by spectroscopic and chromatographic analyses. Resveratrol was determined to be a highly potent inhibitor of human TYR (IC50 = 0.39 μg mL−1) as compared with p-coumaric acid (IC50 = 0.66 μg mL−1) and arbutin (IC50 > 100 μg mL−1) and inhibited melanin synthesis by human epidermal melanocytes at subtoxic concentrations. This study suggests that resveratrol and resveratrol-containing extracts of Vitis Viniferae Caulis have a potential use as skin whitening agents.

show abstract

“…RV is a small molecule (228 Da), with a quite simple chemical structure and equipped with several functional groups, that includes hydroxyphenyl and benzene diol groups, aromatic rings and a double-bound as a linker. The presence of these functional groups makes RV an attractive molecule to be modified into more effective derivatives (Lee et al, 2010;Li et al, 2016). Numerous synthetic methods can be used to modify the molecular structure of RV and the most common structural modifications founded in the literature are: hydroxylation; amination/amidation/imination; methoxylation; prenylation; and glycosylation (Figure 2).…”

Section: Resveratrol Derivatives (Rvd)mentioning

confidence: 99%

Resveratrol Derivatives as Potential Treatments for Alzheimer’s and Parkinson’s Disease

Arbo

André‐Miral

Nasre-Nasser

et al. 2020

Front. Aging Neurosci.

View full text Add to dashboard Cite

Neurodegenerative diseases are characterized by the progressive loss of neurons in different regions of the nervous system. Alzheimer's disease (AD) and Parkinson's disease (PD) are the two most prevalent neurodegenerative diseases, and the symptoms associated with these pathologies are closely related to the regions that are most affected by the process of neurodegeneration. Despite their high prevalence, currently, there is no cure or disease-modifying drugs for the treatment of these conditions. In the last decades, due to the need for the development of new treatments for neurodegenerative diseases, several authors have investigated the neuroprotective actions of naturally occurring molecules, such as resveratrol. Resveratrol is a stilbene found in several plants, including grapes, blueberries, raspberries, and peanuts. Studies have shown that resveratrol presents neuroprotective actions in experimental models of AD and PD, however, its clinical application is limited due to its rapid metabolism and low bioavailability. In this context, studies have proposed that structural changes in the resveratrol molecule, including glycosylation, alkylation, halogenation, hydroxylation, methylation, and prenylation could lead to the development of derivatives with enhanced bioavailability and pharmacological activity. Therefore, this review article aims to discuss how resveratrol derivatives could represent viable molecules in the search for new drugs for the treatment of AD and PD.

show abstract

Syntheses of Resveratrol and its Hydroxylated Derivatives as Radical Scavenger and Tyrosinase Inhibitor

Cited by 26 publications

References 16 publications

Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological Activity and Molecular Modelling Evidence for Cooperativity between Viniferin Enantiomers

Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological Activity and Molecular Modelling Evidence for Cooperativity between Viniferin Enantiomers

Isolation of Resveratrol from Vitis Viniferae Caulis and Its Potent Inhibition of Human Tyrosinase

Resveratrol Derivatives as Potential Treatments for Alzheimer’s and Parkinson’s Disease

Contact Info

Product

Resources

About