Astringin

Astringin
Chemical structure of astringin
Names
IUPAC name
(2S,3R,4S,5S,6R)-2-[3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Identifiers
29884-49-9 
ChEBI CHEBI:2899 
ChEMBL ChEMBL358769 Yes
ChemSpider 4445028 Yes
Jmol-3D images Image
PubChem 5281712
Properties
C20H22O9
Molar mass 406.38 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Astringin is a stilbenoid. It is the piceatannol glucoside. It can be found in the bark of Picea sitchensis[1][2] or Picea abies (Norway spruce).[3]

It is also present in Vitis vinifera cells cultures[4] and in wine.[5]


See also

References

  1. Stilbene glucosides in the bark of Picea sitchensis. Masakazu Aritomi, Dervilla M.X. Donnelly, Phytochemistry, Volume 15, Issue 12, 1976, Pages 2006–2008, doi:10.1016/S0031-9422(00)88881-0
  2. Astringin and isorhapontin distribution in Sitka spruce trees. Claudia D. Toscano Underwood and Raymond B. Pearce, Phytochemistry, Volume 30, Issue 7, 1991, Pages 2183–2189, doi:10.1016/0031-9422(91)83610-W
  3. Stilbenes and resin acids in relation to the penetration of Heterobasidion annosum through the bark of Picea abies. M. Lindberg, L. Lundgren, R. Gref and M. Johansson, European Journal of Forest Pathology, May 1992, Volume 22, Issue 2, pages 95–106, doi:10.1111/j.1439-0329.1992.tb01436.x
  4. Antioxidant Activity of the Stilbene Astringin, Newly Extracted from Vitis vinifera Cell Cultures. Jean-Michel Mérillon, Bernard Fauconneau, Pierre Waffo Teguo, Laurence Barrier, Joseph Vercauteren and François Huguet, Clinical Chemistry, June 1997, vol. 43, no. 6, pages 1092-1093 (article)
  5. Vitrac, Xavier; Bornet, Aurélie; Vanderlinde, Regina; Valls, Josep; Richard, Tristan; Delaunay, Jean-Claude; Mérillon, Jean-Michel; Teissédre, Pierre-Louis (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): 5664–9. doi:10.1021/jf050122g. PMID 15998130.