epsilon-ViniferinCAS# 62218-08-0 |
- Viniferin
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- cis-ε-Viniferin
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 62218-08-0 | SDF | Download SDF |
| PubChem ID | 5281728 | Appearance | Powder |
| Formula | C28H22O6 | M.Wt | 454.5 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Solubility | Soluble in methanol; sparingly soluble in water | ||
| Chemical Name | 5-[(2R,3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol | ||
| SMILES | C1=CC(=CC=C1C=CC2=CC(=CC3=C2C(C(O3)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O)O | ||
| Standard InChIKey | FQWLMRXWKZGLFI-YVYUXZJTSA-N | ||
| Standard InChI | InChI=1S/C28H22O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,27-33H/b4-1+/t27-,28+/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Epsilon-viniferin shows a human cytochrome P450 enzymes inhition activity. 2. Epsilon-Viniferin is a bacteriostatic stilbenoid as it antagonized the bactericidal activity of vancomycin. 3. Epsilon-viniferin and epsilon-viniferin pentaacetate slightly reduce cell proliferation but might protect from cell degenerescence. 4. Epsilon-viniferin exhibits good antioxidant capacity in the DMSO/O(-)(2) polar system (IC50= 0.14 mM). 5. (-)-Trans-epsilon-viniferin is an inhibitor of noradrenaline and 5-hydroxytryptamine uptake and of monoamine oxidase activity, it may be of value as a structural template for the design and development of new antidepressant drugs. |
| Targets | 5-HT Receptor | MAO | Antifection |
epsilon-Viniferin Dilution Calculator
epsilon-Viniferin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.2002 mL | 11.0011 mL | 22.0022 mL | 44.0044 mL | 55.0055 mL |
| 5 mM | 0.44 mL | 2.2002 mL | 4.4004 mL | 8.8009 mL | 11.0011 mL |
| 10 mM | 0.22 mL | 1.1001 mL | 2.2002 mL | 4.4004 mL | 5.5006 mL |
| 50 mM | 0.044 mL | 0.22 mL | 0.44 mL | 0.8801 mL | 1.1001 mL |
| 100 mM | 0.022 mL | 0.11 mL | 0.22 mL | 0.44 mL | 0.5501 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Bacteriostatic antimicrobial combination: antagonistic interaction between epsilon-viniferin and vancomycin against methicillin-resistant Staphylococcus aureus.[Pubmed:24783205]
Biomed Res Int. 2014;2014:461756.
Stilbenoids have been considered as an alternative phytotherapeutic treatment against methicillin-resistant Staphylococcus aureus (MRSA) infection. The combined effect of epsilon-Viniferin and johorenol A with the standard antibiotics, vancomycin and linezolid, was assessed against MRSA ATCC 33591 and HUKM clinical isolate. The minimum inhibitory concentration (MIC) value of the individual tested compounds and the fractional inhibitory concentration index (FICI) value of the combined agents were, respectively, determined using microbroth dilution test and microdilution checkerboard (MDC) method. Only synergistic outcome from checkerboard test will be substantiated for its rate of bacterial killing using time-kill assay. The MIC value of epsilon -viniferin against ATCC 33591 and johorenol A against both strains was 0.05 mg/mL whereas HUKM strain was susceptible to 0.1 mg/mL of epsilon-Viniferin. MDC study showed that only combination between epsilon-Viniferin and vancomycin was synergistic against ATCC 33591 (FICI 0.25) and HUKM (FICI 0.19). All the other combinations (epsilon-Viniferin-linezolid, johorenol A-vancomycin, and johorenol A-linezolid) were either indifferent or additive against both strains. However, despite the FICI value showing synergistic effect for epsilon-Viniferin-vancomycin, TKA analysis displayed antagonistic interaction with bacteriostatic action against both strains. As conclusion, epsilon-Viniferin can be considered as a bacteriostatic stilbenoid as it antagonized the bactericidal activity of vancomycin. These findings therefore disputed previous report that epsilon-Viniferin acted in synergism with vancomycin but revealed that it targets similar site in close proximity to vancomycin's action, possibly at the bacterial membrane protein. Hence, this combination has a huge potential to be further studied and developed as an alternative treatment in combating MRSA in future.
epsilon-Viniferin is more effective than its monomer resveratrol in improving the functions of vascular endothelial cells and the heart.[Pubmed:22738966]
Biosci Biotechnol Biochem. 2012;76(5):954-60.
The present study compared the effects of resveratrol and its dimer epsilon-Viniferin on vascular endothelial cells (VECs) functions, and on the blood pressure and cardiac mass of spontaneously hypertensive rats (SHRs). Treatment of VECs with these compounds enhanced cell proliferation via nitric oxide generation and protected the cells from oxidative stress by suppressing increases in intracellular oxygen species. epsilon-Viniferin was more potent than resveratrol in most of these effects. epsilon-Viniferin, but not resveratrol inhibited angiotensin-converting enzyme activity in vitro. Three weeks of epsilon-Viniferin treatment (5 mg/kg) reduced the systolic blood pressure and improved the whole cardiac mass and left ventricle mass indexes in SHRs. In contrast, resveratrol administration (2.5 mg/kg) failed to lower the blood pressure and significantly improve these mass indexes. These data suggest that epsilon-Viniferin as well as resveratrol may be involved in protecting the functions of VECs and the heart.
Inhibition of Pseudomonas aeruginosa and Escherichia coli O157:H7 biofilm formation by plant metabolite epsilon-viniferin.[Pubmed:23819562]
J Agric Food Chem. 2013 Jul 24;61(29):7120-6.
Pathogenic biofilms are associated with persistent infection due to their high resistances to diverse antibiotics. Pseudomonas aeruginosa infects plants, animals, and humans and is a major cause of nosocomial diseases in patients with cystic fibrosis. In the present study, the antibiofilm abilities of 522 plant extracts against P. aeruginosa PA14 were examined. Three Carex plant extracts at a concentration of 200 mug/mL inhibited P. aeruginosa biofilm formation by >80% without affecting planktonic cell growth. In the most active extract of Carex pumila , resveratrol dimer epsilon-Viniferin was one of the main antibiofilm compounds against P. aeruginosa. Interestingly, epsilon-Viniferin at 10 mug/mL inhibited biofilm formation of enterohemorrhagic Escherichia coli O157:H7 by 98%. Although Carex extracts and trans-resveratrol are known to possess antimicrobial activity, this study is the first to report that C. pumila extract and epsilon-Viniferin have antibiofilm activity against P. aeruginosa and E. coli O157:H7.
(-)-Trans-epsilon-viniferin, a polyphenol present in wines, is an inhibitor of noradrenaline and 5-hydroxytryptamine uptake and of monoamine oxidase activity.[Pubmed:16828740]
Eur J Pharmacol. 2006 Aug 7;542(1-3):54-60.
(-)-Trans-epsilon-Viniferin (epsilon-Viniferin, 5-200 microM), a dimer of resveratrol, concentration-dependently inhibited the uptake of [3H]noradrenaline and [3H]5-HT by synaptosomes from rat brain (being slightly but significantly more selective against [3H]noradrenaline) and the uptake of [3H]5-HT by human platelets. On the other hand, epsilon-Viniferin (5-200 microM) concentration-dependently inhibited the enzymatic activity of commercial (human recombinant) monoamine oxidase (MAO) isoform (MAO-A and MAO-B) activity, being slightly but significantly more selective against MAO-B than against MAO-A. Taking into account that the principal groups of drugs used to treat major depression are noradrenaline/5-HT uptake or MAO inhibitors, under the assumption that epsilon-Viniferin exhibits a similar behaviour in humans in vivo, our results suggest that this natural polyphenol may be of value as a structural template for the design and development of new antidepressant drugs with two important biochemical activities combined in the same chemical structure: noradrenaline/5-HT uptake and MAO inhibitory activity.
Antioxidant properties of trans-epsilon-viniferin as compared to stilbene derivatives in aqueous and nonaqueous media.[Pubmed:11853506]
J Agric Food Chem. 2002 Feb 27;50(5):1213-7.
trans-epsilon-Viniferin, the dimer of resveratrol, extracted from Vitis vinifera, has been evaluated for its antioxidant capacity. Its properties have been compared to those of resveratrol and synthetic stilbenic derivatives (4-hydroxystilbene, 4,4'-dihydroxystilbene, 3,5-dihydroxystilbene, and trimethylresveratrol), in regard to their liposolubility using two media with different polarity. The bleaching of beta-carotene by lipoperoxyl (LOO.) radicals in an oil/water (O/W) emulsion and the scavenging of superoxide anions (O(-)(2) in dimethyl sulfoxide (DMSO) using 5,5-dimethyl-1-pyrroline-N-oxide as a spin trap were followed using UV-visible and electron paramagnetic resonance, respectively. epsilon-Viniferin exhibits the best antioxidant capacity in the DMSO/O(-)(2) polar system (IC(50) = 0.14 mM) while 4,4'-dihydroxystilbene presents the highest antioxidant capacity in the O/W/LOO. system (inhibition of beta-carotene bleaching, 82%). Partition coefficients and kinetics of partition between 1-octanol and water were measured to discuss the antioxidant efficiency of the compounds in relation with their chemical structure.
