Astringin

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
CAS Number	29884-49-9^N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:2899^N
ChEMBL	ChEMBL358769^Y
ChemSpider	4445028^Y
PubChem	5281712
InChI InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1^Y Key: PERPNFLGJXUDDW-CUYWLFDKSA-N^Y InChI=1/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1 Key: PERPNFLGJXUDDW-CUYWLFDKBH
SMILES O(c2cc(O)cc(\C=C\c1ccc(O)c(O)c1)c2)[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO
Properties
Chemical formula	C₂₀H₂₂O₉
Molar mass	406.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
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]

References

↑ 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
↑ 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
↑ 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
↑ 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)
↑ 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.

Hydroxystilbenes and their glycosides (monomeric forms)

Dihydroxylated

Trihydroxylated

Tetrahydroxylated

O-methylated

4-Methoxyresveratrol Gnetucleistol D (2-methoxyoxyresveratrol) Gnetucleistol E (3-methoxy-isorhapontigenin) Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene) Pinostilbene (3-methoxyresveratrol) Pterostilbene (3',5'-dimethoxyresveratrol) Rhapontigenin (piceatannol 4'-methyl ether)

Combretastatins	Combretastatin A-1 Combretastatin A-4

carboxylated

other acylations

of resveratrol	Piceid (trans-Resveratrol-3-O-glucoside) trans-Resveratrol-3-O-glucuronide Resveratroloside (trans-resveratrol-4'-O-beta-D-glucopyranoside)

of rhapontigenin	Rhapontigenin 3-O-rutinoside 4'-Methoxy-(E)-resveratrol 3-O-rutinoside Rhaponticin (Rhapontigenin glucoside)

Oligomeric forms

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