| Identification | Back Directory | [Name]
epsilon-viniferin | [CAS]
62218-08-0 | [Synonyms]
e-viniferin
Ε-VINIFERIN
trans-ε-Viniferin
epsilon-viniferin
epsilion-Viniferin
ε-Viniferin Standard
(-)-trans-ε-viniferin
(-)-trans-epsilon-viniferin
(2R)-2β-(4-Hydroxyphenyl)-3α-(3,5-dihydroxyphenyl)-4-[(E)-4-hydroxystyryl]-2,3-dihydrobenzofuran-6-ol
(2R)-2β-(4-Hydroxyphenyl)-3α-(3,5-dihydroxyphenyl)-4-(4-hydroxy-trans-styryl)-2,3-dihydrobenzofuran-6-ol
[2R,(-)]-2β-(4-Hydroxyphenyl)-3α-(3,5-dihydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydrobenzofuran-6-ol
5-[(2R,3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydrobenzofuran-3-yl]benzene-1,3-diol
(-)-5-[[(2R)-2,3-Dihydro-6-hydroxy-2β-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)vinyl]benzofuran]-3α-yl]-1,3-benzenediol
1,3-Benzenediol, 5-[(2R,3R)-2,3-dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-[(1E)-2-(4-hydroxyphenyl)ethenyl]-3-benzofuranyl]- | [Molecular Formula]
C28H22O6 | [MDL Number]
MFCD12964987 | [MOL File]
62218-08-0.mol | [Molecular Weight]
454.47 |
| Chemical Properties | Back Directory | [Melting point ]
approximate 157℃ (dec.) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in methanol; | [form ]
Powder | [color ]
Off-white to gray | [Water Solubility ]
sparingly soluble in water | [LogP]
3.802 (est) |
| Hazard Information | Back Directory | [Description]
trans-ε-Viniferin is a stilbene polyphenol and dimer of trans-resveratrol that has been found in various red wines and has diverse biological activities. It induces disaggregation of aggregated amyloid-β (1-42) (Aβ42; ) fibrils in a cell-free assay and decreases Aβ42- and IL-1β-induced release of TNF-α and IL-6 in primary mouse neuron and astrocyte cocultures. trans-ε-Viniferin reduces cytotoxicity induced by truncated huntingtin (Htt) in PC12 cells (EC50 = 30 nM). It also reduces production of reactive oxygen species (ROS), mitochondrial dysfunction, and PGC-1α depletion and increases protein levels and deacetylase activity of sirtuin 3 (SIRT3) in cells expressing mutant Htt. trans-ε-Viniferin inhibits calcium-activated chloride channel currents in HT-29 cells (IC50 = ~1 μM). In vivo, trans-ε-viniferin (2 μg per animal) reduces rotavirus-induced secretory diarrhea in mice without affecting the rotaviral infection. Dietary administration of trans-ε-viniferin reduces hepatic triglyceride accumulation and body weight increases in a mouse model of diet-induced obesity. | [Uses]
ε-Viniferin is a stilbene extract posessing cytotoxic effects and may contain anti-cancer properties. | [Definition]
ChEBI: (-)-trans-epsilon-viniferin is a stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol. It has a role as a metabolite. It is a member of 1-benzofurans, a polyphenol and a stilbenoid. It is functionally related to a trans-resveratrol. It is an enantiomer of a (+)-trans-epsilon-viniferin. | [in vivo]
ε-?Viniferin (5 mg/kg, i.p., 5 days per week for 4 weeks) inhibits tumor growth in A549 cell xenograft nude mice model without hepatic and kidney injury, and inhibits tumor metastasis in A549 cell lung metastasis mouse model[3][4].
ε-?Viniferin (0.2% in diet, 4 weeks) prevents diet-induced obesity in mice[7].
| Animal Model: | A549 cell xenograft nude mice model[3] | | Dosage: | 5 mg/kg | | Administration: | i.p., 5 days per week for 4 weeks | | Result: | Inhibited tumor weight and volume.
Induced apoptosis in tumor sections.
Decreased serum ALT, AST, bilirubin, and creatinine levels. |
| [target]
5-HT Receptor | MAO | Antifection | [IC 50]
CYP2B6: 3 μM (Ki, (BROD)); CYP1A2: 5 μM (Ki, (EROD)); CYP3A4: 10 μM (Ki, (TST)); CYP4A: 15 μM (IC50, (LwOH)); CYP2E1: 25 μM (IC50, (CHZ)); CYP2A6: 60 μM (Ki, (COH)) | [References]
[1] XAVIER VITRAC. Determination of Stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, ε-viniferin) in Brazilian Wines[J]. Journal of Agricultural and Food Chemistry, 2005, 53 14: 5664-5669. DOI: 10.1021/jf050122g
[2] ELODIE VION . Trans ε-viniferin is an amyloid-β disaggregating and anti-inflammatory drug in a mouse primary cellular model of Alzheimer’s disease[J]. Molecular and Cellular Neuroscience, 2018, 88: Pages 1-6. DOI: 10.1016/j.mcn.2017.12.003
[3] JINRONG FU. trans-(-)-ε-Viniferin increases mitochondrial sirtuin 3 (SIRT3), activates AMP-activated protein kinase (AMPK), and protects cells in models of Huntington Disease.[J]. The Journal of Biological Chemistry, 2012: 24460-24472. DOI: 10.1074/jbc.m112.382226
[4] BO YU . Resveratrol dimer trans-ε-viniferin prevents rotaviral diarrhea in mice by inhibition of the intestinal calcium-activated chloride channel[J]. Pharmacological research, 2018, 129: Pages 453-461. DOI: 10.1016/j.phrs.2017.11.016
[5] KAZUAKI OHARA . ε-Viniferin, a resveratrol dimer, prevents diet-induced obesity in mice[J]. Biochemical and biophysical research communications, 2015, 468 4: Pages 877-882. DOI: 10.1016/j.bbrc.2015.11.047 |
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