A modulator of acetylcholine release
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Syringin

Item No. 22387

Technical Information
Formal Name
4-[(1E)-3-hydroxy-1-propen-1-yl]-2,6-dimethoxyphenyl-β-D-glucopyranoside
CAS Number
118-34-3
Synonyms
  • Eleutheroside B
  • NSC 287441
Molecular Formula
C17H24O9
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
221, 266 nm
SMILES
COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(OC)=CC(/C=C/CO)=C1
InChi Code
InChI=1S/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1
InChi Key
QJVXKWHHAMZTBY-GCPOEHJPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Syringin is a phenylpropanoid glycoside first isolated from A. senticosus that enhances acetylcholine release in pancreatic cells leading to an increase in insulin release through the muscarinic M3 receptor.1,2 Syringin dose-dependently (50, 75, and 100 µg/kg, i.v.) decreases plasma glucose levels and increases insulin-like immunoreactivity and C-peptide in rats, and these effects last at least 60 minutes. In a rat model of type 1 diabetes, it decreases plasma glucose and increases β-endorphin release from the adrenal medulla.3 Syringin increases autophagy through AMP-activated protein kinase α (AMPKα) activation concomitant with preventing the progression of cardiac hypertrophy in mice following aortic banding.4 It also has immunomodulatory effects, likely due to its metabolite sinapyl alcohol.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rao, U.S.M., Zin, T., Abdurrazak, M., et alChemistry and pharmacology of syringin, a novel bioglycoside: A review. Asian J. Pharm. Clin. Res. 8(3), 20-25 (2015).

    2. Liu, K.Y., Wu, Y.-C., Liu, I.-M., et alRelease of acetylcholine by syringin, an active principle of Eleutherococcus senticosus, to raise insulin secretion in Wistar rats. Neurosci. Lett. 434(2), 195-199 (2008).

    3. Niu, H.-S., Hsu, F.-L., Liu, I.-M., et alIncrease of β-endorphin secretion by syringin, an active principle of Eleutherococcus senticosus, to produce antihyperglycemic action in type 1-like diabetic rats. Horm. Metab. Res. 39(12), 894-898 (2007).

    4. Li, F., Zhang, N., Wu, Q., et alSyringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy. Int. J. Mol. Med. 39(1), 199-207 (2017).

    5. Choi, J., Shin, K.-M., Park, H.-J., et alAnti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringin. Planta Med. 70(11), 1027-1032 (2004).