Sophoricoside

Names

[ CAS No. ]:
152-95-4

[ Name ]:
Sophoricoside

[Synonym ]:
4-(5,7-Dihydroxy-4-oxo-4H-chromen-3-yl)phenyl β-D-glucopyranoside
Genistein-4'-glucoside
4H-1-Benzopyran-4-one, 3-[4-(β-D-glucopyranosyloxy)phenyl]-5,7-dihydroxy-
Genistein 4'-Glucoside
4'-(β-D-Glucopyranosyloxy)-5,7-dihydroxyisoflavone
4H-1-Benzopyran-4-one,3-[4-(
4',5,7-Trihydroxyisoflavone-4'-D-glucoside
MFCD01075138
Sophoricoside
3-[4-(b-D-Glucopyranosyloxy)phenyl]-5,7-dihydroxy-411-1-benzopyran-4-one

Biological Activity

[Description]:

Sophoricoside is an isoflavone glycoside isolated from Sophora japonica and has anti-inflammatory, anti-cancer and immunosuppressive effects.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Flavonoids

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[In Vitro]

Sophoricoside is an isoflavone glycoside isolated from Sophora japonica and has anti-inflammatory, anti-cancer and immunosuppressive effects. The results show that Sophoricoside (50 μM) significantly inhibits the PMACI-induced histamine release. The inhibition rate reaches up to 30.24%. The maximal rates of TNF-α, IL-8 and IL-6 inhibition by Sophoricoside (50 μM) are approximately 31.42%, 43.43% and 34.24%, respectively. The rates of the levels of Rel/p65 inhibition in nuclear by Sophoricoside (50 μM) is approximately 50.14%. Results show that the enhanced caspase-1 activity induced by PMACI is significantly reduced by Sophoricoside in a dose-dependent manner[1].

[In Vivo]

When the Sophoricoside is orally administered 1 h before compound 48/80 injections, the scratching behaviors is reduced. The inhibition rate of Sophoricoside (2 mg/kg) is approximately 41.21%. Orally administered Sophoricoside inhibits the scratching behaviors by 47.31%. When mice are treated for 2 weeks with Sophoricoside, the atopic dermatitis is recovered to a significant extent[1].

[Kinase Assay]

Cells are incubated with the Sophoricoside for 1 h, and then incubated with PMACI for 2 h. The reaction is stopped by cooling the tubes in ice. The cells are separated from the released histamine by centrifugation at 400×g for 5 min at 4°C. The histamine levels are measured by ELISA using a histamine assay kit according to the manufacturer’s directions. Duplicate aliquots of supernatant are measured for each sample[1].

[Cell Assay]

To test the cell viability by each concentration of Sophoricoside, the MTT colorimetric assay is performed. Briefly, HMC-1 cells (3×105 cells/well) are incubated with Sophoricoside (1 to 50 μM) for 12 h. After the addition of MTT solution, the cells are incubated at 37°C for 4 h. The crystallized MTT (formazan) is dissolved in dimethyl sulfoxide and the absorbance is measured at 540 nm[1].

[Animal admin]

BALB/c mice (5 weeks, 19 to 20 g) are used in this study. The dorsal skin of the BALB/c mice (n=6) is shaved and treated with a depilatory prior to the experiment. The mice are sensitized with 100 μL of 0.15% DNCB in acetone-olive oil (3:1) applied to the dorsal skin twice per week for 5 weeks. Control mice receive vehicle (acetone/olive oil=3:1). After 3 weeks, Sophoricoside (2 mg/kg) is orally administered 2 weeks until the end of the experiment[1].

[References]

[1]. Kim SJ, et al. The ameliorative effect of sophoricoside on mast cell-mediated allergic inflammation in vivo and in vitro. Molecules. 2013 May 22;18(5):6113-27.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
763.3±60.0 °C at 760 mmHg

[ Melting Point ]:
285ºC

[ Molecular Formula ]:
C₂₁H₂₀O₁₀

[ Molecular Weight ]:
432.378

[ Flash Point ]:
271.5±26.4 °C

[ Exact Mass ]:
432.105652

[ PSA ]:
170.05000

[ LogP ]:
0.31

[ Vapour Pressure ]:
0.0±2.7 mmHg at 25°C

[ Index of Refraction ]:
1.717

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
T,C

[ Risk Phrases ]:
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S26-S36-S45-S24/25

[ RIDADR ]:
UN 3276 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
AL7970000

[ Packaging Group ]:
II

[ Hazard Class ]:
8

Sophoricoside

Names

Biological Activity

Chemical & Physical Properties

MSDS

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Safety Information

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Related Compounds