epsilon-Viniferin

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ε-Viniferin
Epsilon-viniferin.svg
(−)-Trans-epsilon-viniferin
Names
IUPAC name
5-[(2R,3R)-6-Hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-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
62218-08-0 N
ChEMBL ChEMBL1224875 YesY
ChemSpider 4445043 YesY
Jmol-3D images Image
PubChem 5281728
Properties
C28H22O6
Molar mass 454.47 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

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

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[edit]

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

See also[edit]

References[edit]

  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 : JDD 6 (6 Suppl): s8–13. PMID 17691204. 
  3. ^ a b 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. 
  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. 
  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. 

External links[edit]