delta-Viniferin

δ-Viniferin

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Names
IUPAC name 5-{(E)-2-[(2R,3R)-3-(3,5-Dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]vinyl}-1,3-benzenediol
Other names δ-Viniferin trans-δ-viniferin cis-δ-viniferin resveratrol (E)-dehydrodimer Maximol A
Identifiers
ChemSpider	552752
Jmol 3D model	Interactive image
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
Properties
Chemical formula	C28H22O6
Molar mass	454.47 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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

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

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.

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

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

See also

• Phenolic content in wine

External links

• Stilbenoids isolated from Vitis vinifera at Schroeder group website