A stilbene glucoside with diverse biological activities
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Isomer(s)
27979Astringin
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2,3,5,4'-Tetrahydroxyl-diphenylethylene 2-O-β-D-Glucoside

Item No. 34594

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,4-dihydroxy-6-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl β-D-glucopyranoside
CAS Number
82373-94-2
Synonyms
  • (E)-2,3,5,4’-Tetrahydroxyl-diphenylethylene 2-O-β-D-Glucoside
  • trans-2,3,5,4’-Tetrahydroxyl-diphenylethylene 2-O-β-D-Glucopyranoside
  • (E )-2,3,5,4′-Tetrahydroxystilbene-2-O-Glucoside
  • trans-2,3,5,4′-Tetrahydroxystilbene-2-O-β-d-Glucopyranoside
  • 2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-Glucoside
  • TSG
Molecular Formula
C20H22O9
Formula Weight
406.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
217, 322 nm
SMILES
OC(C=C1)=CC=C1/C=C/C(C=C(C=C2O)O)=C2O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO
InChi Code
InChI=1S/C20H22O9/c21-9-15-16(25)17(26)18(27)20(28-15)29-19-11(7-13(23)8-14(19)24)4-1-10-2-5-12(22)6-3-10/h1-8,15-18,20-27H,9H2/b4-1+/t15-,16-,17+,18-,20+/m1/s1
InChi Key
JAYVHSBYKLLDJC-DSNJPTTOSA-N
Origin
Plant/Fallopia multiflora
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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Download most recent Certificate of Analysis for this product

    25 mg

    $103

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    50 mg

    $173

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    100 mg

    $303

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    250 mg

    $602

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    Product Description

    2,3,5,4’-Tetrahydroxyl-diphenylethylene 2-O-β-D-glucoside (TSG) is a stilbene glucoside that has been found in P. multiflorum and has diverse biological activities.1,2,3,4 It scavenges DPPH (Item No. 14805) radicals in a cell-free assay (IC50 = 40 µM).1 TSG inhibits doxorubicin-induced apoptosis, loss of mitochondrial membrane potential, and generation of reactive oxygen species (ROS) in mouse cardiomyocytes.2 Ex vivo, TSG (30, 60, and 120 mg/kg) increases acetylcholine-induced relaxation of, and nitric oxide (NO) levels in, aortic rings isolated from a rat model of diet-induced atherosclerosis.3 In vivo, TSG (15 and 40 mg/kg) reduces infarct area and neuronal apoptosis in a mouse model of ischemia and reperfusion injury induced by middle cerebral artery occlusion (MCAO).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ryu, G., Ju, J.H., Park, Y.J., et al. The radical scavenging effects of stilbene glucosides from Polygonum multiflorum. Arch. Pharm. Res. 25(5), 636-639 (2002).

    2. Zhang, S.-H., Wang, W.-Q., and Wang, J.L. Protective effect of tetrahydroxystilbene glucoside on cardiotoxicity induced by doxorubicin in vitro and in vivo. Acta Pharmacol. Sin. 30(11), 1479-1487 (2009).

    3. Zhang, W., Xu, X.-L., Wang, Y.-Q., et al. Effects of 2,3,4',5-tetrahydroxystilbene 2-O-β-ᴅ-glucoside on vascular endothelial dysfunction in atherogenic-diet rats. Planta Med. 75(11), 1209-1214 (2009).

    4. Wang, T., Gu, J., Wu, P.-F., et al. Protection by tetrahydroxystilbene glucoside against cerebral ischemia: Involvement of JNK, SIRT1, and NF-ᴋB pathways and inhibition of intracellular ROS/RNS generation. Free Radic. Biol. Med. 47(3), 229-240 (2009).