epsilon-viniferin CAS 62218-08-0

Introduction：Basic information about epsilon-viniferin CAS 62218-08-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

epsilon-viniferin Basic information

• Product Name: epsilon-viniferin
• Synonyms: epsilon-viniferin;(-)-5-[[(2R)-2,3-Dihydro-6-hydroxy-2β-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)vinyl]benzofuran]-3α-yl]-1,3-benzenediol;(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)-4-hydroxystyryl]-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;e-viniferin;(-)-trans-epsilon-viniferin
• CAS: 62218-08-0
• MF: C28H22O6
• MW: 454.47
• Mol File: 62218-08-0.mol

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
• Major Application: food and beverages
• 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
• InChIKey: FQWLMRXWKZGLFI-YVYUXZJTSA-N
• SMILES: O1[C@H]([C@@H](c4c1cc(cc4\C=C\c5ccc(cc5)O)O)c3cc(cc(c3)O)O)c2ccc(cc2)O
• LogP: 3.802 (est)

Safety Information

• WGK Germany: WGK 3
• Storage Class: 11 - Combustible Solids

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

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