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{{lowercase title}}
{{DISPLAYTITLE:''delta''-Viniferin}}
{{chembox
{{chembox
| Verifiedfields =
| Verifiedfields =
| verifiedrevid =
| verifiedrevid =
| Name = δ-Viniferin
| Name = δ-Viniferin
| Reference = <!-- <ref>http://www.</ref> -->
| Reference = <!-- <ref>{{cite web |url=http://www./ |title=Home |website=}}</ref> -->
| ImageFile = Delta-viniferin.svg
| ImageFile = Delta-viniferin.svg
| ImageSize = 250px
| ImageSize = 250px
| IUPACName = 5-{(E)-2-[(2R,3R)-3-(3,5-Dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]vinyl}-1,3-benzenediol
| PIN = 5-[(2''R'',3''R'')-5-[(1''E'')-2-(3,5-Dihydroxyphenyl)ethen-1-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
| OtherNames = δ-Viniferin<br>trans-δ-viniferin<br>cis-δ-viniferin<br>resveratrol (E)-dehydrodimer<br>Maximol A<ref name=Shikishima>{{Cite journal | last1 = Shikishima | first1 = Y. | last2 = Takaishi | first2 = Y. | last3 = Honda | first3 = G. | last4 = Ito | first4 = M. | last5 = Takeda | first5 = Y. | last6 = Kodzhimatov | first6 = O. K. | last7 = Ashurmetov | first7 = O. | doi = 10.1016/S0031-9422(00)00370-8 | title = Phenylbutanoids and stilbene derivatives of Rheum maximowiczii | journal = Phytochemistry | volume = 56 | issue = 4 | pages = 377–381 | year = 2001 | pmid = 11249105| pmc = }}</ref>
| OtherNames = δ-Viniferin<br />''trans''-δ-Viniferin<br />Resveratrol (''E'')-dehydrodimer<br />Maximol A<ref name=Shikishima>{{Cite journal | last1 = Shikishima | first1 = Y. | last2 = Takaishi | first2 = Y. | last3 = Honda | first3 = G. | last4 = Ito | first4 = M. | last5 = Takeda | first5 = Y. | last6 = Kodzhimatov | first6 = O. K. | last7 = Ashurmetov | first7 = O. | doi = 10.1016/S0031-9422(00)00370-8 | title = Phenylbutanoids and stilbene derivatives of Rheum maximowiczii | journal = Phytochemistry | volume = 56 | issue = 4 | pages = 377–381 | year = 2001 | pmid = 11249105| bibcode = 2001PChem..56..377S }}</ref>
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref =
| ChemSpiderID_Ref =
| ChemSpiderID = 552752
| ChemSpiderID = 552752
| InChI =
| CASNo = 204076-78-8
| CASNo_Ref = <ref>{{cite web |last1=Chambers |first1=Michael |title=ChemIDplus - 0204076788 - LILPTCHQLRKZNG-CKKRXTSSSA-N - delta-Viniferin - Similar structures search, synonyms, formulas, resource links, and other chemical information. |url=https://chem.nlm.nih.gov/chemidplus/sid/0204076788 |website=chem.nlm.nih.gov |language=en}}</ref>
| InChIKey =
| SMILES1 =
| ChEMBL = 4209546
| StdInChI_Ref =
| ChEBI = 76147
| StdInChI =
| StdInChIKey_Ref =
| StdInChIKey =
| CASNo =
| CASNo_Ref =
| ChEMBL_Ref =
| ChEMBL =
| PubChem = 637098
| PubChem = 637098
| SMILES = C1=CC(=CC=C1[C@H]2[C@@H](C3=C(O2)C=CC(=C3)/C=C/C4=CC(=CC(=C4)O)O)C5=CC(=CC(=C5)O)O)O}}
| SMILES = C1=CC(=CC=C1[C@H]2[C@@H](C3=C(O2)C=CC(=C3)/C=C/C4=CC(=CC(=C4)O)O)C5=CC(=CC(=C5)O)O)O
| StdInChI=1S/C28H22O6/c29-20-6-4-18(5-7-20)28-27(19-12-23(32)15-24(33)13-19)25-11-16(3-8-26(25)34-28)1-2-17-9-21(30)14-22(31)10-17/h1-15,27-33H/b2-1+/t27-,28+/m1/s1
| StdInChIKey = LILPTCHQLRKZNG-CKKRXTSSSA-N
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>28</sub>H<sub>22</sub>O<sub>6</sub>
| Formula = C<sub>28</sub>H<sub>22</sub>O<sub>6</sub>
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}}
}}
}}
}}
'''δ-Viniferin''' is a resveratrol dehydro[[dimer (chemistry)|dimer]]. It is an isomer of [[epsilon-viniferin]]. It can be isolated from stressed grapevine (''[[Vitis vinifera]]'') leaves.<ref name=Pezet>{{Cite journal | last1 = Pezet | first1 = R. | last2 = Perret | first2 = C. | last3 = Jean-Denis | first3 = J. B. | last4 = Tabacchi | first4 = R. | last5 = Gindro | first5 = K. | last6 = Viret | first6 = O. | doi = 10.1021/jf030227o | title = Δ-Viniferin, a Resveratrol Dehydrodimer: One of the Major Stilbenes Synthesized by Stressed Grapevine Leaves | journal = Journal of Agricultural and Food Chemistry | volume = 51 | issue = 18 | pages = 5488–5492 | year = 2003 | pmid = 12926902| pmc = }}</ref> It is also found in plant cell cultures.<ref>{{Cite journal | last1 = Waffo-Teguo | first1 = P. | last2 = Lee | first2 = D. | last3 = Cuendet | first3 = M. | last4 = Mérillon | first4 = J. M. | last5 = Pezzuto | first5 = J. M. | last6 = Kinghorn | first6 = A. D. | doi = 10.1021/np000426r | title = Two New Stilbene Dimer Glucosides from Grape (Vitisvinifera) Cell Cultures | journal = Journal of Natural Products | volume = 64 | issue = 1 | pages = 136–138 | year = 2001 | pmid = 11170689| pmc = }}</ref> or in wine.<ref>{{Cite journal | last1 = Vitrac | first1 = X. | last2 = Bornet | first2 = A. L. | last3 = Vanderlinde | first3 = R. | last4 = Valls | first4 = J. | last5 = Richard | first5 = T. | last6 = Delaunay | first6 = J. C. | last7 = Mérillon | first7 = J. M. | last8 = Teissédre | first8 = P. L. | doi = 10.1021/jf050122g | 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 = 5664–5669 | year = 2005 | pmid = 15998130| pmc = }}</ref> It can also be found in ''[[Rheum maximowiczii]]''.<ref name=Shikishima/>
'''δ-Viniferin''' is a resveratrol dehydro[[dimer (chemistry)|dimer]]. It is an isomer of [[epsilon-viniferin]]. It can be isolated from stressed grapevine (''[[Vitis vinifera]]'') leaves.<ref name=Pezet>{{Cite journal | last1 = Pezet | first1 = R. | last2 = Perret | first2 = C. | last3 = Jean-Denis | first3 = J. B. | last4 = Tabacchi | first4 = R. | last5 = Gindro | first5 = K. | last6 = Viret | first6 = O. | doi = 10.1021/jf030227o | title = Δ-Viniferin, a Resveratrol Dehydrodimer: One of the Major Stilbenes Synthesized by Stressed Grapevine Leaves | journal = Journal of Agricultural and Food Chemistry | volume = 51 | issue = 18 | pages = 5488–5492 | year = 2003 | pmid = 12926902}}</ref> It is also found in plant cell cultures<ref>{{Cite journal | last1 = Waffo-Teguo | first1 = P. | last2 = Lee | first2 = D. | last3 = Cuendet | first3 = M. | last4 = Mérillon | first4 = J. M. | last5 = Pezzuto | first5 = J. M. | last6 = Kinghorn | first6 = A. D. | doi = 10.1021/np000426r | title = Two New Stilbene Dimer Glucosides from Grape (Vitisvinifera) Cell Cultures | journal = Journal of Natural Products | volume = 64 | issue = 1 | pages = 136–138 | year = 2001 | pmid = 11170689}}</ref> and wine.<ref>{{Cite journal | last1 = Vitrac | first1 = X. | last2 = Bornet | first2 = A. L. | last3 = Vanderlinde | first3 = R. | last4 = Valls | first4 = J. | last5 = Richard | first5 = T. | last6 = Delaunay | first6 = J. C. | last7 = Mérillon | first7 = J. M. | last8 = Teissédre | first8 = P. L. | doi = 10.1021/jf050122g | 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 = 5664–5669 | year = 2005 | pmid = 15998130}}</ref> It can also be found in ''[[Rheum maximowiczii]]''.<ref name=Shikishima/>


It is a grapevine [[phytoalexin]] following stresses<ref name=Pezet/> like [[Fungal infection in plants|fungal infection]] (by ''[[Plasmopara viticola]]'', the agent of downy mildew),<ref>{{Cite journal | last1 = Timperio | first1 = A. M. | last2 = d’Alessandro | first2 = A. | last3 = Fagioni | first3 = M. | last4 = Magro | first4 = P. | last5 = Zolla | first5 = L. | title = Production of the phytoalexins trans-resveratrol and delta-viniferin in two economy-relevant grape cultivars upon infection with Botrytis cinerea in field conditions | doi = 10.1016/j.plaphy.2011.07.008 | journal = Plant Physiology and Biochemistry | volume = 50 | issue = 1 | pages = 65–71 | year = 2012 | pmid = 21821423 | pmc = }}</ref> [[UV light]] [[irradiation]] or [[ozone]] treatment.<ref>{{Cite journal | last1 = González-Barrio | first1 = R. O. | last2 = Beltrán | first2 = D. | last3 = Cantos | first3 = E. | last4 = Gil | first4 = M. A. I. | last5 = Espín | first5 = J. C. | last6 = Tomás-Barberán | first6 = F. A. | doi = 10.1021/jf060160f | title = Comparison of Ozone and UV-C Treatments on the Postharvest Stilbenoid Monomer, Dimer, and Trimer Induction in Var. 'Superior' White Table Grapes | journal = Journal of Agricultural and Food Chemistry | volume = 54 | issue = 12 | pages = 4222–4228 | year = 2006 | pmid = 16756350| pmc = }}</ref>
It is a grapevine [[phytoalexin]] following stresses<ref name=Pezet/> like [[Fungal infection in plants|fungal infection]] (by ''[[Plasmopara viticola]]'', the agent of downy mildew),<ref>{{Cite journal | last1 = Timperio | first1 = A. M. | last2 = d’Alessandro | first2 = A. | last3 = Fagioni | first3 = M. | last4 = Magro | first4 = P. | last5 = Zolla | first5 = L. | title = Production of the phytoalexins trans-resveratrol and delta-viniferin in two economy-relevant grape cultivars upon infection with Botrytis cinerea in field conditions | doi = 10.1016/j.plaphy.2011.07.008 | journal = Plant Physiology and Biochemistry | volume = 50 | issue = 1 | pages = 65–71 | year = 2012 | pmid = 21821423 }}</ref> [[UV light]] [[irradiation]] or [[ozone]] treatment.<ref>{{Cite journal | last1 = González-Barrio | first1 = R. O. | last2 = Beltrán | first2 = D. | last3 = Cantos | first3 = E. | last4 = Gil | first4 = M. A. I. | last5 = Espín | first5 = J. C. | last6 = Tomás-Barberán | first6 = F. A. | doi = 10.1021/jf060160f | title = Comparison of Ozone and UV-C Treatments on the Postharvest Stilbenoid Monomer, Dimer, and Trimer Induction in Var. 'Superior' White Table Grapes | journal = Journal of Agricultural and Food Chemistry | volume = 54 | issue = 12 | pages = 4222–4228 | year = 2006 | pmid = 16756350}}</ref>


''[[Botryosphaeria obtusa]]'', a pathogen responsible for the black dead arm disease of grapevine, has also been shown to be able to oxidise wood δ-resveratrol into delta-viniferin.<ref>{{Cite journal | last1 = Djoukeng | first1 = J. D. S. | last2 = Polli | first2 = S. | last3 = Larignon | first3 = P. | last4 = Abou-Mansour | first4 = E. | title = Identification of phytotoxins from Botryosphaeria obtusa, a pathogen of black dead arm disease of grapevine | doi = 10.1007/s10658-008-9419-6 | journal = European Journal of Plant Pathology | volume = 124 | issue = 2 | pages = 303 | year = 2009 | pmid = | pmc = }}</ref>
''[[Botryosphaeria obtusa]]'', a pathogen responsible for the black dead arm disease of grapevine, has also been shown to be able to oxidise wood δ-resveratrol into delta-viniferin.<ref>{{Cite journal | last1 = Djoukeng | first1 = J. D. S. | last2 = Polli | first2 = S. | last3 = Larignon | first3 = P. | last4 = Abou-Mansour | first4 = E. | title = Identification of phytotoxins from Botryosphaeria obtusa, a pathogen of black dead arm disease of grapevine | doi = 10.1007/s10658-008-9419-6 | journal = European Journal of Plant Pathology | volume = 124 | issue = 2 | pages = 303 | year = 2009 | s2cid = 37168306 | url = http://doc.rero.ch/record/12212/files/10658_2008_Article_9419.pdf }}</ref>


In cell cultures, the use of [[methyl jasmonate]] and [[jasmonic acid]] as [[elicitor]]s stimulates δ-viniferin [[biosynthesis]].<ref>{{Cite journal | last1 = Santamaria | first1 = A. R. | last2 = Mulinacci | first2 = N. | last3 = Valletta | first3 = A. | last4 = Innocenti | first4 = M. | last5 = Pasqua | first5 = G. | title = Effects of Elicitors on the Production of Resveratrol and Viniferins in Cell Cultures ofVitis viniferaL. Cv Italia | doi = 10.1021/jf201181n | journal = Journal of Agricultural and Food Chemistry | volume = 59 | issue = 17 | pages = 9094–9101 | year = 2011 | pmid = 21751812| pmc = }}</ref>
In cell cultures, the use of [[methyl jasmonate]] and [[jasmonic acid]] as [[elicitor]]s stimulates δ-viniferin [[biosynthesis]].<ref>{{Cite journal | last1 = Santamaria | first1 = A. R. | last2 = Mulinacci | first2 = N. | last3 = Valletta | first3 = A. | last4 = Innocenti | first4 = M. | last5 = Pasqua | first5 = G. | title = Effects of Elicitors on the Production of Resveratrol and Viniferins in Cell Cultures ofVitis viniferaL. Cv Italia | doi = 10.1021/jf201181n | journal = Journal of Agricultural and Food Chemistry | volume = 59 | issue = 17 | pages = 9094–9101 | year = 2011 | pmid = 21751812}}</ref>


Delta-viniferin can also be produced from [[resveratrol]] by human [[PTGS1]] (COX-1, cyclooxygenase-1)<ref>{{Cite journal | last1 = Szewczuk | first1 = L. M. | last2 = Lee | first2 = S. H. | last3 = Blair | first3 = I. A. | last4 = Penning | first4 = T. M. | title = Viniferin Formation by COX-1: Evidence for Radical Intermediates during Co-oxidation of Resveratrol | doi = 10.1021/np049702i | journal = Journal of Natural Products | volume = 68 | issue = 1 | pages = 36–42 | year = 2005 | pmid = 15679314| pmc = }}</ref> or from trans-resveratrol and (−)-[[epsilon-viniferin]] by [[horseradish peroxidase]].<ref>{{Cite journal | last1 = Wilkens | first1 = A. | last2 = Paulsen | first2 = J. | last3 = Wray | first3 = V. | last4 = Winterhalter | first4 = P. | title = Structures of Two Novel Trimeric Stilbenes Obtained by Horseradish Peroxidase Catalyzed Biotransformation oftrans-Resveratrol and (−)-ε-Viniferin | doi = 10.1021/jf100606p | journal = Journal of Agricultural and Food Chemistry | volume = 58 | issue = 11 | pages = 6754–6761 | year = 2010 | pmid = 20455561| pmc = }}</ref>
Delta-viniferin can also be produced from [[resveratrol]] by human [[PTGS1]] (COX-1, cyclooxygenase-1)<ref>{{Cite journal | last1 = Szewczuk | first1 = L. M. | last2 = Lee | first2 = S. H. | last3 = Blair | first3 = I. A. | last4 = Penning | first4 = T. M. | title = Viniferin Formation by COX-1: Evidence for Radical Intermediates during Co-oxidation of Resveratrol | doi = 10.1021/np049702i | journal = Journal of Natural Products | volume = 68 | issue = 1 | pages = 36–42 | year = 2005 | pmid = 15679314}}</ref> or from ''trans''-resveratrol and (−)-[[epsilon-viniferin]] by [[horseradish peroxidase]].<ref>{{Cite journal | last1 = Wilkens | first1 = A. | last2 = Paulsen | first2 = J. | last3 = Wray | first3 = V. | last4 = Winterhalter | first4 = P. | title = Structures of Two Novel Trimeric Stilbenes Obtained by Horseradish Peroxidase Catalyzed Biotransformation oftrans-Resveratrol and (−)-ε-Viniferin | doi = 10.1021/jf100606p | journal = Journal of Agricultural and Food Chemistry | volume = 58 | issue = 11 | pages = 6754–6761 | year = 2010 | pmid = 20455561}}</ref>


== See also ==
== See also ==
* [[Phenolic content in wine]]
* [[Phenolic content in wine]]
* [[Viniferin]] (disambiguous)
* [[α-Viniferin]]
* [[ε-Viniferin]]
* [[R-Viniferin]]
* [[R2-Viniferin]]


== References ==
== References ==
Line 57: Line 58:


== External links ==
== External links ==
* [http://www.biologie.uni-freiburg.de/data/bio2/schroeder/Vitis_vinifera.html Stilbenoids isolated from ''Vitis vinifera'' at Schroeder group website]
* [https://web.archive.org/web/20120430124851/http://www.biologie.uni-freiburg.de/data/bio2/schroeder/Vitis_vinifera.html Stilbenoids isolated from ''Vitis vinifera'' at Schroeder group website]


{{Stilbenoids}}
{{Stilbenoids}}


{{DEFAULTSORT:Viniferin, delta-}}
{{DEFAULTSORT:Viniferin, δ-}}
[[Category:Resveratrol oligomers]]
[[Category:Resveratrol oligomers]]
[[Category:Stilbenoid dimers]]
[[Category:Stilbenoid dimers]]
[[Category:Phytoalexins]]
[[Category:Phytoalexins]]
[[Category:Oxygen heterocycles]]
[[Category:Heterocyclic compounds with 2 rings]]

Latest revision as of 18:40, 15 September 2024

δ-Viniferin
Names
Preferred IUPAC name
5-[(2R,3R)-5-[(1E)-2-(3,5-Dihydroxyphenyl)ethen-1-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Other names
δ-Viniferin
trans-δ-Viniferin
Resveratrol (E)-dehydrodimer
Maximol A[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C28H22O6/c29-20-6-4-18(5-7-20)28-27(19-12-23(32)15-24(33)13-19)25-11-16(3-8-26(25)34-28)1-2-17-9-21(30)14-22(31)10-17/h1-15,27-33H/b2-1+/t27-,28+/m1/s1
    Key: LILPTCHQLRKZNG-CKKRXTSSSA-N
  • C1=CC(=CC=C1[C@H]2[C@@H](C3=C(O2)C=CC(=C3)/C=C/C4=CC(=CC(=C4)O)O)C5=CC(=CC(=C5)O)O)O
Properties
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).

δ-Viniferin is a resveratrol dehydrodimer. It is an isomer of epsilon-viniferin. It can be isolated from stressed grapevine (Vitis vinifera) leaves.[3] It is also found in plant cell cultures[4] and wine.[5] It can also be found in Rheum maximowiczii.[1]

It is a grapevine phytoalexin following stresses[3] like fungal infection (by Plasmopara viticola, the agent of downy mildew),[6] UV light irradiation or ozone treatment.[7]

Botryosphaeria obtusa, a pathogen responsible for the black dead arm disease of grapevine, has also been shown to be able to oxidise wood δ-resveratrol into delta-viniferin.[8]

In cell cultures, the use of methyl jasmonate and jasmonic acid as elicitors stimulates δ-viniferin biosynthesis.[9]

Delta-viniferin can also be produced from resveratrol by human PTGS1 (COX-1, cyclooxygenase-1)[10] or from trans-resveratrol and (−)-epsilon-viniferin by horseradish peroxidase.[11]

See also

[edit]

References

[edit]
  1. ^ a b Shikishima, Y.; Takaishi, Y.; Honda, G.; Ito, M.; Takeda, Y.; Kodzhimatov, O. K.; Ashurmetov, O. (2001). "Phenylbutanoids and stilbene derivatives of Rheum maximowiczii". Phytochemistry. 56 (4): 377–381. Bibcode:2001PChem..56..377S. doi:10.1016/S0031-9422(00)00370-8. PMID 11249105.
  2. ^ Chambers, Michael. "ChemIDplus - 0204076788 - LILPTCHQLRKZNG-CKKRXTSSSA-N - delta-Viniferin - Similar structures search, synonyms, formulas, resource links, and other chemical information". chem.nlm.nih.gov.
  3. ^ a b Pezet, R.; Perret, C.; Jean-Denis, J. B.; Tabacchi, R.; Gindro, K.; Viret, O. (2003). "Δ-Viniferin, a Resveratrol Dehydrodimer: One of the Major Stilbenes Synthesized by Stressed Grapevine Leaves". Journal of Agricultural and Food Chemistry. 51 (18): 5488–5492. doi:10.1021/jf030227o. PMID 12926902.
  4. ^ Waffo-Teguo, P.; Lee, D.; Cuendet, M.; Mérillon, J. M.; Pezzuto, J. M.; Kinghorn, A. D. (2001). "Two New Stilbene Dimer Glucosides from Grape (Vitisvinifera) Cell Cultures". Journal of Natural Products. 64 (1): 136–138. doi:10.1021/np000426r. PMID 11170689.
  5. ^ 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.
  6. ^ Timperio, A. M.; d’Alessandro, A.; Fagioni, M.; Magro, P.; Zolla, L. (2012). "Production of the phytoalexins trans-resveratrol and delta-viniferin in two economy-relevant grape cultivars upon infection with Botrytis cinerea in field conditions". Plant Physiology and Biochemistry. 50 (1): 65–71. doi:10.1016/j.plaphy.2011.07.008. PMID 21821423.
  7. ^ González-Barrio, R. O.; Beltrán, D.; Cantos, E.; Gil, M. A. I.; Espín, J. C.; Tomás-Barberán, F. A. (2006). "Comparison of Ozone and UV-C Treatments on the Postharvest Stilbenoid Monomer, Dimer, and Trimer Induction in Var. 'Superior' White Table Grapes". Journal of Agricultural and Food Chemistry. 54 (12): 4222–4228. doi:10.1021/jf060160f. PMID 16756350.
  8. ^ Djoukeng, J. D. S.; Polli, S.; Larignon, P.; Abou-Mansour, E. (2009). "Identification of phytotoxins from Botryosphaeria obtusa, a pathogen of black dead arm disease of grapevine" (PDF). European Journal of Plant Pathology. 124 (2): 303. doi:10.1007/s10658-008-9419-6. S2CID 37168306.
  9. ^ Santamaria, A. R.; Mulinacci, N.; Valletta, A.; Innocenti, M.; Pasqua, G. (2011). "Effects of Elicitors on the Production of Resveratrol and Viniferins in Cell Cultures ofVitis viniferaL. Cv Italia". Journal of Agricultural and Food Chemistry. 59 (17): 9094–9101. doi:10.1021/jf201181n. PMID 21751812.
  10. ^ Szewczuk, L. M.; Lee, S. H.; Blair, I. A.; Penning, T. M. (2005). "Viniferin Formation by COX-1: Evidence for Radical Intermediates during Co-oxidation of Resveratrol". Journal of Natural Products. 68 (1): 36–42. doi:10.1021/np049702i. PMID 15679314.
  11. ^ Wilkens, A.; Paulsen, J.; Wray, V.; Winterhalter, P. (2010). "Structures of Two Novel Trimeric Stilbenes Obtained by Horseradish Peroxidase Catalyzed Biotransformation oftrans-Resveratrol and (−)-ε-Viniferin". Journal of Agricultural and Food Chemistry. 58 (11): 6754–6761. doi:10.1021/jf100606p. PMID 20455561.
[edit]
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