epsilon-viniferin Chemical Properties

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)

epsilon-viniferin Usage And Synthesis

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

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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