Δ-Viniferin

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]

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
CAS Number	204076-78-8[2]
3D model (JSmol)	Interactive image
ChEBI	CHEBI:76147
ChEMBL	ChEMBL4209546
ChemSpider	552752
PubChem CID	637098
InChI 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
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
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). Infobox references

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

• Phenolic content in wine
• Viniferin (disambiguous)
• α-Viniferin
• ε-Viniferin
• R-Viniferin
• R2-Viniferin