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Astringin
Names
IUPAC name
3-[(E )-2-(2,3-Dihydroxyphenyl)ethen-1-yl]-5-hydroxyphenyl β-D -glucopyranoside
Systematic IUPAC name
(2S ,3R ,4S ,5S ,6R )-2-{3-[(E )-2-(3,4-Dihydroxyphenyl)ethen-1-yl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Identifiers
ChEBI
ChEMBL
ChemSpider
UNII
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
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
C 20 H 22 O 9
Molar mass
406.387 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Astringin is a
stilbenoid , the 3-β-D -glucoside of
piceatannol .
[1] It can be found in the bark of
Picea sitchensis
[2]
[3] and
Picea abies (Norway spruce).
[4]
It is also present in
Vitis vinifera cells cultures
[5] and in
wine .
[6]
See also
References
^
CID 5281712 from
PubChem
^ Aritomi, Masakazu; Donnelly, Dervilla M.X. (1976). "Stilbene glucosides in the bark of Picea sitchensis". Phytochemistry . 15 (12): 2006–2008.
Bibcode :
1976PChem..15.2006A .
doi :
10.1016/S0031-9422(00)88881-0 .
^ Toscano Underwood, Claudia D.; Pearce, Raymond B. (1991). "Astringin and isorhapontin distribution in Sitka spruce trees". Phytochemistry . 30 (7): 2183–2189.
Bibcode :
1991PChem..30.2183T .
doi :
10.1016/0031-9422(91)83610-W .
^ Lindberg, M.; Lundgren, L.; Gref, R.; Johansson, M. (1992). "Stilbenes and resin acids in relation to the penetration of Heterobasidion annosum through the bark of Picea abies". European Journal of Forest Pathology . 22 (2): 95–106.
doi :
10.1111/j.1439-0329.1992.tb01436.x .
^ Mérillon, J. M.; Fauconneau, B.; Teguo, P. W.; Barrier, L.; Vercauteren, J.; Huguet, F. (1997).
"Antioxidant activity of the stilbene astringin, newly extracted from Vitis vinifera cell cultures" . Clinical Chemistry . 43 (6 Pt 1): 1092–1093.
doi :
10.1093/clinchem/43.6.1092 .
PMID
9191572 .
^ 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 .
Dihydroxylated Trihydroxylated Tetrahydroxylated O-methylated
carboxylated other acylations
Glycosides
of resveratrol of rhapontigenin
Oligomeric forms