Astringin - Misplaced Pages

Astringin
Names

IUPAC name 3--5-hydroxyphenyl β-D-glucopyranoside
Systematic IUPAC name (2S,3R,4S,5S,6R)-2-{3--5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Identifiers
CAS Number	29884-49-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:2899
ChEMBL	ChEMBL358769
ChemSpider	4445028
PubChem CID	5281712
UNII	4ER6YKM4YL
CompTox Dashboard (EPA)	DTXSID401029689
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/s1Key: PERPNFLGJXUDDW-CUYWLFDKSA-N 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/s1Key: PERPNFLGJXUDDW-CUYWLFDKBH
SMILES O(c2cc(O)cc(\C=C\c1ccc(O)c(O)c1)c2)3O((O)(O)3O)CO
Properties
Chemical formula	C₂₀H₂₂O₉
Molar mass	406.387 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of Picea sitchensis and Picea abies (Norway spruce).

It is also present in Vitis vinifera cells cultures and in wine.

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.

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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