Δ-Viniferin

δ-Viniferin
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
3D model (JSmol)	Interactive image;
ChemSpider	552752;
PubChem CID	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
	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.^[2] It is also found in cell cultures.^[3] or in wine.^[4] It can also be found in Rheum maximowiczii.^[1]

It is a grapevine phytoalexin following stresses^[2] like fungal infection (by Plasmopara viticola, the agent of downy mildew),^[5] UV light irradiation or ozone treatment.^[6]

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.^[7]

In cell cultures, the use of methyl jasmonate and jasmonic acid as elicitors stimulates δ-viniferin biosynthesis.^[8]

Delta-viniferin can also be produced from resveratrol by human PTGS1 (COX-1, cyclooxygenase-1)^[9] or from trans-resveratrol and (-)-epsilon-viniferin by horseradish peroxidase.^[10]

References

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External links

Stilbenoids isolated from Vitis vinifera at Schroeder group website

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See also

References

External links