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δ-Viniferin

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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

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References

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  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.
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