ε-​Viniferin  (Synonyms: epsilon-Viniferin)

ε-Viniferin (epsilon-Viniferin), the dimer of Resveratrol and can be isolated from Vitis vinifera, displays a potent inhibitory for all the CYP activities, with K_i values from 0.5-20 μM. ε-Viniferin possesses potent antioxidant, anti-inflammatory, anti-diabetic, and anti-neurodegenerative capacity^[1][2][3].

ε-​Viniferin (1-15 μM, 24-72 h) inhibits proliferation of HOS, U2OS, and A549 cells^[3].
ε-​Viniferin (20 μM, 24 h) induces DNA fragmentation and nuclear condensation in HOS, U2OS, A549 cells^[3].
ε-​Viniferin (10 μM, 1 h) inhibits TGF-β1 induced EMT, invasion and migration, and reverses TGF-β1-induced ROS, MMP2, vimentin, Zeb1, Snail, p-SMAD2, p-SMAD3, and ABCG2 expression in A549 cells^[4].
ε-​Viniferin (10 μM, 3 min) inhibits fMLP (0.1 μM)-induced superoxide anion production in human neutrophils, as well as fMLP-induced phosphorylation of ERK, Akt, Src or intracellular calcium mobilization^[5].
ε-​Viniferin (50 nM-10 μM, 48 h) protects cells against Rotenone (HY-B1756)-induced neurotoxicity in SH-SY5Y cells via the SIRT3/FOXO3 pathway^[6].
ε-​Viniferin (1 μM, 24 h) inhibits Rotenone (HY-B1756)-induced mitochondrial depolarization and oxidative stress in SH-SY5Y cells^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

454.47

C₂₈H₂₂O₆

62218-08-0

Solid

Off-white to gray

OC1=CC([C@H]2[C@H](C3=CC=C(O)C=C3)OC4=CC(O)=CC(/C=C/C5=CC=C(O)C=C5)=C24)=CC(O)=C1

Room temperature in continental US; may vary elsewhere.

4°C, sealed storage, away from moisture and light

*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)

• [1]. Piver B, et al. Differential inhibition of human cytochrome P450 enzymes by epsilon-viniferin, the dimer of resveratrol: comparison with resveratrol and polyphenols from alcoholized beverages. Life Sci. 2003 Jul 18;73(9):1199-213.  [Content Brief]

  [2]. XAVIER VITRAC, et al. Determination of Stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, E-viniferin) in Brazilian Wines. J. Agric. Food Chem. 2005, 53, 5664−5669.

  [3]. Huang C, et al. ε-Viniferin and α-viniferin alone or in combination induced apoptosis and necrosis in osteosarcoma and non-small cell lung cancer cells. Food Chem Toxicol. 2021 Dec;158:112617.  [Content Brief]

  [4]. Chiou WC, et al. α-Viniferin and ε-Viniferin Inhibited TGF-β1-Induced Epithelial-Mesenchymal Transition, Migration and Invasion in Lung Cancer Cells through Downregulation of Vimentin Expression. Nutrients. 2022 May 30;14(11):2294.  [Content Brief]

  [5]. Liao HR, et al. The anti-inflammatory effect of ε-viniferin by specifically targeting formyl peptide receptor 1 on human neutrophils. Chem Biol Interact. 2021 Aug 25;345:109490.  [Content Brief]

  [6]. Zhang S, et al. Neuroprotective mechanisms of ε-viniferin in a rotenone-induced cell model of Parkinson's disease: significance of SIRT3-mediated FOXO3 deacetylation. Neural Regen Res. 2020 Nov;15(11):2143-2153.  [Content Brief]

  [7]. Ohara K, et al. ε-Viniferin, a resveratrol dimer, prevents diet-induced obesity in mice. Biochem Biophys Res Commun. 2015 Dec 25;468(4):877-82.  [Content Brief]