Ε-Viniferin: Difference between revisions

ε-Viniferin
	; (-)-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; Iso-[epsilon]-viniferin; cis-ε-viniferin; Cis-epsilon-viniferin
Identifiers
CAS Number	62218-08-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1224875 ;
ChemSpider	4445043 ;
PubChem CID	5281728;
	InChI 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 Key: FQWLMRXWKZGLFI-YVYUXZJTSA-N ; 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;
	SMILES 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
Chemical formula	C28H22O6
Molar mass	454.47 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 20:27, 22 May 2012

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 inhition activity.^[8]

Glycosides

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

References

^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/j.ejphar.2006.06.005, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1016/j.ejphar.2006.06.005 instead.
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External links

e-viniferin on phenol-explorer.eu

Template:Natural-phenol-stub

[1] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/j.ejphar.2006.06.005, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1016/j.ejphar.2006.06.005 instead.

[2] Template:Cite PMID

[Kim-3] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1271/bbb.66.1990, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1271/bbb.66.1990 instead.

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[5] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1007/BF02124034, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1007/BF02124034 instead.

[6] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 15998130, please use {{cite journal}} with |pmid=15998130 instead.

[7] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/j.fitote.2011.02.006, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1016/j.fitote.2011.02.006 instead.

[8] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/S0024-3205(03)00420-X, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1016/S0024-3205(03)00420-X instead.

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@@ Line 10: / Line 10: @@
 |  ImageCaption = (-)-Trans-epsilon-viniferin
 |  IUPACName = 5-[(2''R'',3''R'')-6-Hydroxy-2-(4-hydroxyphenyl)-4-[(''E'')-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
-|  OtherNames = Viniferin<br>''epsilon''-Viniferin<br>(-)-''epsilon''-Viniferin<br>(-)-(E)-epsilon-viniferin<br>trans-ε-viniferin<br>(-)-Trans-epsilon-viniferin<ref>(-)-Trans-epsilon-viniferin, a polyphenol present in wines, is an inhibitor of noradrenaline and 5-hydroxytryptamine uptake and of monoamine oxidase activity. Yáñez M, Fraiz N, Cano E and Orallo F, Eur J Pharmacol., 2006 Aug 7, 542(1-3), pages 54-60, {{PMID|16828740}}, {{doi|10.1016/j.ejphar.2006.06.005}}</ref><br><nowiki>Iso-[epsilon]-viniferin</nowiki><ref>In vivo skin antioxidant effect of a new combination based on a specific Vitis vinifera shoot extract and a biotechnological extract. Cornacchione S, Sadick NS, Neveu M, Talbourdet S, Lazou K, Viron C, Renimel I, de Quéral D, Kurfurst R, Schnebert S, Heusèle C, André P and Perrier E, J Drugs Dermatol., 2007 Jun, 6(6 Suppl), s8-13, {{PMID|17691204}}</ref><br>cis-ε-viniferin<br>Cis-epsilon-viniferin<ref name=Kim>Antioxidative activity of resveratrol and its derivatives isolated from seeds of Paeonia lactiflora. Kim HJ, Chang EJ, Cho SH, Chung SK, Park HD and Choi SW, Biosci Biotechnol Biochem., 2002 Sep, 66(9), pages 1990-1993, {{PMID|12400706}}, {{doi|10.1271/bbb.66.1990}}</ref>
+|  OtherNames = Viniferin<br>''epsilon''-Viniferin<br>(-)-''epsilon''-Viniferin<br>(-)-(E)-epsilon-viniferin<br>trans-ε-viniferin<br>(-)-Trans-epsilon-viniferin<ref>{{Cite doi|10.1016/j.ejphar.2006.06.005|noedit}}</ref><br><nowiki>Iso-[epsilon]-viniferin</nowiki><ref>{{Cite PMID|17691204|noedit}}</ref><br>cis-ε-viniferin<br>Cis-epsilon-viniferin<ref name=Kim>{{Cite doi|10.1271/bbb.66.1990|noedit}}</ref>
 |Section1= {{Chembox Identifiers
 |  CASNo_Ref = {{cascite|changed|??}}
@@ Line 46: / Line 46: @@
 '''ε-Viniferin''' is a naturally occurring [[natural phenol|phenol]], belonging to the [[stilbenoid]]s family. It is a [[resveratrol]] [[Dimer (chemistry)|dimer]].
-It is found in ''[[Vitis vinifera]]''<ref>Antioxidant properties of trans-epsilon-viniferin as compared to stilbene derivatives in aqueous and nonaqueous media. Privat C, Telo JP, Bernardes-Genisson V, Vieira A, Souchard JP and Nepveu F, J Agric Food Chem., 2002 Feb 27, 50(5), pages 1213-1217, {{PMID|11853506}}, {{doi|10.1021/jf010676t}}</ref> grapevines,<ref>A new class of phytoalexins from grapevines. P. Langcake and R. J. Pryce, Cellular and Molecular Life Sciences, 1977, Volume 33, Number 2, pp. 151-152, {{doi|10.1007/BF02124034}} PMID 844529</ref> in [[wine]]s,<ref>{{cite journal |last1=Vitrac |first1=Xavier |last2=Bornet |first2=Aurélie |last3=Vanderlinde |first3=Regina |last4=Valls |first4=Josep |last5=Richard |first5=Tristan |last6=Delaunay |first6=Jean-Claude |last7=Mérillon |first7=Jean-Michel |last8=Teissédre |first8=Pierre-Louis |title=Determination of Stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, ε-viniferin) in Brazilian Wines. |journal=Journal of Agricultural and Food Chemistry |volume=53 |issue=14 |pages=5664–9 |year=2005 |pmid=15998130 |doi=10.1021/jf050122g}}</ref> in the Oriental medicinal plant ''[[Vitis coignetiae]]'' and in the stem bark of ''[[Dryobalanops aromatica]]''.<ref>Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica. Wibowo A, Ahmat N, Hamzah AS, Sufian AS, Ismail NH, Ahmad R, Jaafar FM, Takayama H. Fitoterapia. 2011 Jun, 82(4), pages 676-81, {{PMID|21338657}}, {{doi|10.1016/j.fitote.2011.02.006}}</ref>
+It is found in ''[[Vitis vinifera]]''<ref>{{Cite doi|10.1021/jf010676t|noedit}}</ref> grapevines,<ref>{{Cite doi|10.1007/BF02124034|noedit}}</ref> in [[wine]]s,<ref>{{Cite pmid|15998130}}</ref> in the Oriental medicinal plant ''[[Vitis coignetiae]]'' and in the stem bark of ''[[Dryobalanops aromatica]]''.<ref>{{Cite doi|10.1016/j.fitote.2011.02.006|noedit}}</ref>
 <br>Cis-epsilon-viniferin can be found in ''[[Paeonia lactiflora]]''.<ref name=Kim/>
-It shows a human [[cytochrome P450]] enzymes inhition activity.<ref>Differential inhibition of human cytochrome P450 enzymes by epsilon-viniferin, the dimer of resveratrol: comparison with resveratrol and polyphenols from alcoholized beverages. Piver B, Berthou F, Dreano Y and Lucas D, Life Sci., 2003 Jul 18, 73(9), pages 1199-1213, {{PMID|12818727}}, {{doi|10.1016/S0024-3205(03)00420-X}}</ref>
+It shows a human [[cytochrome P450]] enzymes inhition activity.<ref>{{Cite doi|10.1016/S0024-3205(03)00420-X|noedit}}</ref>
 == Glycosides ==

Revision as of 20:27, 22 May 2012

Glycosides

See also

References

External links