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epsilon-Viniferin

January 05, 2023

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
  • 62218-08-0 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1224875 Y
ChemSpider
  • 4445043 Y
  • 5281728
UNII
  • 0K8Z2K6Y7O Y
  • 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 Y
    Key: FQWLMRXWKZGLFI-YVYUXZJTSA-N Y
  • 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 YN ?)

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. ^ 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. 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.

External links

  •   Media related to Epsilon-Viniferin at Wikimedia Commons
  • e-viniferin on phenol-explorer.eu


 

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

January 05, 2023
epsilon, viniferin, viniferin, naturally, occurring, phenol, belonging, stilbenoids, family, resveratrol, dimer, viniferin, trans, viniferinnamespreferred, iupac, name, hydroxy, hydroxyphenyl, hydroxyphenyl, ethen, dihydro, benzofuran, benzene, diolother, name. e Viniferin is a naturally occurring phenol belonging to the stilbenoids family It is a resveratrol dimer e Viniferin trans e ViniferinNamesPreferred 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 diolOther names Viniferinepsilon Viniferin epsilon Viniferin E epsilon viniferintrans e viniferin Trans epsilon viniferin 1 Iso epsilon viniferin 2 cis e viniferinCis epsilon viniferin 3 IdentifiersCAS Number 62218 08 0 Y3D model JSmol Interactive imageChEMBL ChEMBL1224875 YChemSpider 4445043 YPubChem CID 5281728UNII 0K8Z2K6Y7O YInChI 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 YKey FQWLMRXWKZGLFI YVYUXZJTSA N YInChI 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 s1Key FQWLMRXWKZGLFI YVYUXZJTBSSMILES C1 CC CC C1C CC2 CC CC3 C2C C O3 C4 CC C C C4 O C5 CC CC C5 O O O OPropertiesChemical formula C 28H 22O 6Molar mass 454 478 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y 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 Contents 1 Glycosides 2 See also 3 References 4 External linksGlycosides EditDiptoindonesin A is a C glucoside of e viniferin See also EditPhenolic content in wineReferences Edit Yanez M Fraiz N Cano E Orallo F 2006 Trans e 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 Cornacchione S Sadick N S Neveu M Talbourdet S Lazou K Viron C Renimel I De Queral D Kurfurst R Schnebert S Heusele C Andre 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 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 S2CID 24367582 Privat C Telo J O P Bernardes Genisson V Vieira A Souchard J P Nepveu F O 2002 Antioxidant Properties oftrans e 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 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 Vitrac X Bornet A L Vanderlinde R Valls J Richard T Delaunay J C Merillon J M Teissedre P L 2005 Determination of Stilbenes d viniferin trans astringin trans piceid cis and trans resveratrol e viniferin in Brazilian Wines Journal of Agricultural and Food Chemistry 53 14 5664 5669 doi 10 1021 jf050122g PMID 15998130 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 Piver B Berthou F O Dreano Y Lucas D L 2003 Differential inhibition of human cytochrome P450 enzymes by e 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 Media related to Epsilon Viniferin at Wikimedia Commons e viniferin on phenol explorer eu This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Epsilon Viniferin amp oldid 1129977480, wikipedia, wiki, book, books, library,

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