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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.