| Identification | Back Directory | [Name]
APIGENIN 6-GLUCOSYL-7-O-METHYL ETHER | [CAS]
6991-10-2 | [Synonyms]
Tris(1
SWERTISIN
SWERTISIN(P)
Swertia flavin
Genkwanin 6-C-Glucoside
3-dichloroisopropyl)phosphate
APIGENIN 6-GLUCOSYL-7-O-METHYL ETHER
4',5-Dihydroxy-7-methoxy-6-β-D-glucopyranosylflavone
Swertisin, 98%, from Swertia diluta (Turcz.) Benth. & Hook.f.
4H-1-Benzopyran-4-one, 6-β-D-glucopyranosyl-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-
6-(β-D-Glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one | [Molecular Formula]
C22H22O10 | [MDL Number]
MFCD32003920 | [MOL File]
6991-10-2.mol | [Molecular Weight]
446.4 |
| Chemical Properties | Back Directory | [Melting point ]
245-246℃ | [Boiling point ]
716.6±60.0 °C(Predicted) | [density ]
1.583±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO; sparingly soluble in methanol; | [form ]
powder | [pka]
5.76±0.40(Predicted) | [color ]
White-pale yellow | [Water Solubility ]
slightly soluble in water | [Major Application]
food and beverages | [InChI]
1S/C22H22O10/c1-30-13-7-14-16(11(25)6-12(31-14)9-2-4-10(24)5-3-9)19(27)17(13)22-21(29)20(28)18(26)15(8-23)32-22/h2-7,15,18,20-24,26-29H,8H2,1H3 | [InChIKey]
ABRULANJVVJLFI-UHFFFAOYSA-N | [SMILES]
O1C(C(C(C(C1c2c(c3c(cc2OC)OC(=CC3=O)c4ccc(cc4)O)O)O)O)O)CO |
| Hazard Information | Back Directory | [Chemical Properties]
Swertisin is a flavonoid compound that appears as a light yellow powder or crystalline powder at room temperature. Its chemical formula is C22H22O10, with a molecular weight of 446. it is soluble in organic solvents such as methanol and dimethyl sulfoxide. It has antioxidant,anti-diabetic, anti-depressant, anti-inflammatory, anti-viral, and anti-radiation pharmacological effects. | [Uses]
food and beverages | [Definition]
ChEBI: Swertisin is a flavone C-glycoside that is 7-O-methylapigenin in which the hydrogen at position 6 has been replaced by a beta-D-glucosyl residue. It has a role as a plant metabolite, an adenosine A1 receptor antagonist, an anti-inflammatory agent, an antioxidant and a hypoglycemic agent. It is a flavone C-glycoside, a monosaccharide derivative, a polyphenol, a monomethoxyflavone and a dihydroxyflavone. It is functionally related to an apigenin. | [Biological Activity]
Swertisin is a flavonoid C-glycoside that has been found in Swertia japonica and has diverse biological activities. It inhibits sodium-glucose cotransporter 2 (SGLT2) in HEK293 cells when used at a concentration of 7.5 μg/ml and is an adenosine A1 receptor antagonist (IC50 = 137 μM). Swertisin (0.2-5 μM) inhibits hepatitis B virus (HBV) replication in HepG2 2.2.15 cells. It decreases blood glucose levels in a mouse model of diabetes induced by streptozotocin (Item No. 13104), as well as prevents scopolamine-induced increases in escape latency in the Morris water maze in mice. | [in vivo]
Swertisin (30 mg/kg, orally, single dose) helps improve symptoms of schizophrenia in mice, including sensory motor gating disruptions and cognitive impairments[1].
Swertisin (2.5 mg/kg, intraperitoneally, once daily, days) reduces the expression of SGLT2 in mouse kidney tissue and can quickly lower blood sugar[2].
Swertisin (0-10 mg/kg, intraperitoneally, every other day, 20 days) significantly inhibits HBV replication in a HBV transgenic mouse model[3]. | Animal Model: | Mice induced by MK801 (HY-15084B)[1] | | Dosage: | 30 mg/kg; single dose | | Administration: | Oral gavage (p.o.) | | Result: | Alleviated the pre-pulse inhibition defect, reversed memory recognition impairment, and the elevated phosphorylation levels of Akt and GSK-3β signaling molecules in the prefrontal cortex restore normal function. |
| Animal Model: | BALB/c mice induced by STZ (HY-13753)[2] | | Dosage: | 2.5 mg/kg; daily; 15 days | | Administration: | Intraperitoneal injection (i.p.) | | Result: | Improved overall glucose homeostasis, reduced SGLT2 expression in renal tissue, reduced PKC expression, and had a rapid hypoglycemic effect. |
| Animal Model: | HBV transgenic mice[3] | | Dosage: | 0, 5, 10 mg/kg; every other day; 20 days | | Administration: | Intraperitoneal injection (i.p.) | | Result: | Showed that there was no significant weight loss, no significant changes in serum ALT and AST levels, and reduced serum HBsAg and HBeAg levels. |
| [IC 50]
SGLT2 | [References]
[1] GURPRIT BHARDWAJ . Swertisin, a novel SGLT2 inhibitor, with improved glucose homeostasis for effective diabetes therapy[J]. Archives of biochemistry and biophysics, 2021, 710: Article 108995. DOI:10.1016/j.abb.2021.108995.
[2] K. PATEL D. P. Biological importance and therapeutic benefit of swertisin: An overview of medicinal importance and pharmacological activities[J]. Current Bioactive Compounds, 2022. DOI:10.2174/1573407218666220801113334.
[3] HONG-YAN XU . Anti-hepatitis B virus activity of swertisin isolated from Iris tectorum Maxim[J]. Journal of ethnopharmacology, 2020, 257: Article 112787. DOI:10.1016/j.jep.2020.112787. |
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