ε-Viniferin

ε-Viniferin is a naturally occurring phenol, belonging to the stilbenoids family. It is a resveratrol dimer.

ε-Viniferin

(−)-trans-ε-Viniferin
Names
Preferred IUPAC name
5-{(2R,3R)-6-Hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]-2,3-dihydro-1-benzofuran-3-yl}benzene-1,3-diol
Other names
Viniferin
epsilon-Viniferin
(−)-epsilon-Viniferin
(−)-(E)-epsilon-viniferin
trans-ε-viniferin
(−)-Trans-epsilon-viniferin[1]
Iso-[epsilon]-viniferin[2]
cis-ε-viniferin
Cis-epsilon-viniferin[3]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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 checkY
    Key: FQWLMRXWKZGLFI-YVYUXZJTSA-N checkY
  • InChI=1/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
    Key: FQWLMRXWKZGLFI-YVYUXZJTBS
  • C1=CC(=CC=C1C=CC2=CC(=CC3=C2C(C(O3)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O)O
Properties
C28H22O6
Molar mass 454.478 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

It is found in Vitis vinifera[4] grapevines,[5] in wines,[6] in the Oriental medicinal plant Vitis coignetiae and in the stem bark of Dryobalanops aromatica.[7]
Cis-epsilon-viniferin can be found in Paeonia lactiflora.[3]

It shows a human cytochrome P450 enzymes inhibition activity.[8]

Glycosides

Diptoindonesin A is a C-glucoside of ε-viniferin.

See also

References
  1. Yáñez, M.; Fraiz, N.; Cano, E.; Orallo, F. (2006). "(−)-Trans-ε-viniferin, a polyphenol present in wines, is an inhibitor of noradrenaline and 5-hydroxytryptamine uptake and of monoamine oxidase activity". European Journal of Pharmacology. 542 (1–3): 54–60. doi:10.1016/j.ejphar.2006.06.005. PMID 16828740.
  2. Cornacchione, S.; Sadick, N. S.; Neveu, M.; Talbourdet, S.; Lazou, K.; Viron, C.; Renimel, I.; De Quéral, D.; Kurfurst, R.; Schnebert, S.; Heusèle, C.; André, P.; Perrier, E. (2007). "In vivo skin antioxidant effect of a new combination based on a specific Vitis vinifera shoot extract and a biotechnological extract". Journal of Drugs in Dermatology. 6 (6 Suppl): s8–13. PMID 17691204.
  3. Kim, H. J.; Chang, E. J.; Cho, S. H.; Chung, S. K.; Park, H. D.; Choi, S. W. (2002). "Antioxidative Activity of Resveratrol and Its Derivatives Isolated from Seeds of Paeonia lactiflora". Bioscience, Biotechnology, and Biochemistry. 66 (9): 1990–3. doi:10.1271/bbb.66.1990. PMID 12400706. S2CID 24367582.
  4. Privat, C.; Telo, J. O. P.; Bernardes-Genisson, V.; Vieira, A.; Souchard, J. P.; Nepveu, F. O. (2002). "Antioxidant Properties oftrans-ε-Viniferin As Compared to Stilbene Derivatives in Aqueous and Nonaqueous Media". Journal of Agricultural and Food Chemistry. 50 (5): 1213–1217. doi:10.1021/jf010676t. PMID 11853506.
  5. Langcake, P.; Pryce, R. J. (1977). "A new class of phytoalexins from grapevines". Experientia. 33 (2): 151–152. doi:10.1007/BF02124034. PMID 844529. S2CID 34370048.
  6. Vitrac, X.; Bornet, A. L.; Vanderlinde, R.; Valls, J.; Richard, T.; Delaunay, J. C.; Mérillon, J. M.; Teissédre, P. L. (2005). "Determination of Stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, ε-viniferin) in Brazilian Wines". Journal of Agricultural and Food Chemistry. 53 (14): 5664–5669. doi:10.1021/jf050122g. PMID 15998130.
  7. Wibowo, A.; Ahmat, N.; Hamzah, A. S.; Sufian, A. S.; Ismail, N. H.; Ahmad, R.; Jaafar, F. M.; Takayama, H. (2011). "Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica". Fitoterapia. 82 (4): 676–681. doi:10.1016/j.fitote.2011.02.006. PMID 21338657.
  8. Piver, B.; Berthou, F. O.; Dreano, Y.; Lucas, D. L. (2003). "Differential inhibition of human cytochrome P450 enzymes by ε-viniferin, the dimer of resveratrol: Comparison with resveratrol and polyphenols from alcoholized beverages". Life Sciences. 73 (9): 1199–1213. doi:10.1016/S0024-3205(03)00420-X. PMID 12818727.


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