Syringin

• CAT Number: R039880
• CAS Number: 118-34-3
• Molecular Formula: C17H24O9
• Molecular Weight: 372.37
• Purity: ≥95%
• Synonyms: 4-[(1E)-3-Hydroxy-1-propen-1-yl]-2,6-dimethoxyphenyl-β-D-glucopyranoside; Eleutheroside B; Ilexanthin A; Ligustrin; Lilacin; Magnolenin; Methoxyconiferine; NSC 287441; Sinapyl alcohol 4-O-glucoside; Siringin; Syringoside
• Target: Autophagy
• Storage: -20°C
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
• InChI: 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
• InChIKey: QJVXKWHHAMZTBY-GCPOEHJPSA-N
• SMILES: COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)OC)C=CCO

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. 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. Syringin increases autophagy through AMP-activated protein kinase α (AMPKα) activation concomitant with preventing the progression of cardiac hypertrophy in mice following aortic banding. It also has immunomodulatory effects, likely due to its metabolite sinapyl alcohol.