Sophoricoside

CAS# 152-95-4

Sophoricoside

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Quality Control of Sophoricoside

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Chemical structure

Sophoricoside

3D structure

Chemical Properties of Sophoricoside

Cas No. 152-95-4 SDF Download SDF
PubChem ID 5321398 Appearance White-beige crystalline
Formula C21H20O10 M.Wt 432.38
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Genistein 4'-O-glucoside; 4',5,7-Trihydroxyisoflavone 4'-O-glucoside
Solubility DMSO : ≥ 150 mg/mL (346.92 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 5,7-dihydroxy-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
SMILES C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)OC4C(C(C(C(O4)CO)O)O)O
Standard InChIKey ISQRJFLLIDGZEP-CMWLGVBASA-N
Standard InChI InChI=1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-3-1-9(2-4-11)12-8-29-14-6-10(23)5-13(24)16(14)17(12)25/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20-,21-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Sophoricoside

The fruits of Sophora japonica L.

Biological Activity of Sophoricoside

DescriptionSophoricoside has anti-inflammatory, anti-cancer, anti-bone loss, and immunosuppressive effects. Sophoricoside is an effective regulator of lipogenesis and glucose consumption and may find utility in the treatment of obesity and type 2 diabetes. Sophoricoside exposure reduced the number of implanted embryos in a dose-dependent manner and failed the embryo implantation through altering the morphology of uterine and compromising the endometrial receptivity.
TargetsNF-kB | Caspase | MMP(e.g.TIMP) | Estrogen receptor | COX | IL Receptor | TNF-α | Progestogen receptor
In vitro

Modulation of lipogenesis and glucose consumption in HepG2 cells and C2C12 myotubes by sophoricoside.[Pubmed: 24352018]

Molecules. 2013 Dec 13;18(12):15624-35.

Sophoricoside, an isoflavone glycoside isolated from Sophora japonica (Leguminosae), has been widely reported as an immunomodulator. In this study, the effects of Sophoricoside on lipogenesis and glucose consumption in HepG2 cells and C2C12 myotubes were investigated.
METHODS AND RESULTS:
Treatment with Sophoricoside at concentrations of 1-10 μM inhibited lipid accumulation in HepG2 cells in a dose-dependent manner. At the same concentration range, no effect on cell viability was observed in the MTT assay. Inhibition of lipogenesis was associated with the downregulation of SREBP-1a, SREBP-1c, SREBP-2 and their downstream target genes (FAS, ACC, HMGR) as revealed by realtime quantitative PCR. The lipid-lowering effect was mediated via the phosphorylation of AMPK. Further investigation of the activities of this isoflavone showed that Sophoricoside has the capability to increase glucose uptake by C2C12 myotubes. It also effectively inhibited the activities of α-glucosidase and α-amylase in vitro and remarkably lowered postprandial hyperglycaemia in starch-loaded C57BL6/J mice.
CONCLUSIONS:
These results suggest that Sophoricoside is an effective regulator of lipogenesis and glucose consumption and may find utility in the treatment of obesity and type 2 diabetes.

Effective bioconversion of sophoricoside to genistein from Fructus sophorae using immobilized Aspergillus niger and Yeast.[Pubmed: 25392205]

World J Microbiol Biotechnol. 2015 Jan;31(1):187-97.

In this study, Sophoricoside from Fructus sophorae was highly bioconversed to genistein by co-immobilized Aspergillus niger and Yeast.
METHODS AND RESULTS:
Bioconversion conditions for genistein were optimized with single-factor experiments. The optimal conditions were as follows: microbial concentration 1.5 × 10(7) cells/mL, wet weight of microorganisms beads 10.0 g/g material, pH 5, ratio of liquid to solid 25:1 (mL/g), temperature 32 °C and time 24 h. Under these conditions, a 34.45-fold increase in production of genistein was observed with a bioreactor. Moreover, the antioxidant activities of the extracts from the fermented and untreated F. sophorae were 0.287 ± 0.11, 0.384 ± 0.08 mg/mL (IC50) and 1.84 ± 0.13, 1.28 ± 0.25 mmol Fe(II)/g, according to the DPPH test and FRAP assay, respectively.
CONCLUSIONS:
The results indicated that the method described in the current work were valuable procedure for the production of genistein, which is of most importance for industrial scale applications as well as food industry.

In vivo

Sophoricoside fails the embryo implantation by compromising the uterine endometrial receptivity at implantation [Pubmed: 24877640 ]

Chem Biol Interact. 2014 Aug 5;219:57-63.

Sophoricoside (SOPH) is an isoflavone glycoside isolated from the fruits of Sophora japonica. Since its first isolation in 1961, there are rare findings about the effects of SOPH on reproductive system.
METHODS AND RESULTS:
In the present study, the pregnant mice administrated by different doses of SOPH were used to explore the effect of SOPH on embryo implantation, especially on the endometrial receptivity. The statistical results showed that the number of implanted embryos was gradually declining along the increasing dose of SOPH. When the administrated dose of SOPH was 600 mg/kg per day, great changes were observed in the exposed uterine morphology and up-regulated progesterone receptor (PR) and down-regulated estrogen receptor α (ERα), E-cadherin, matrix metalloproteinase-2 (MMP-2) and integrin β3 were also found in SOPH-exposed uterine.
CONCLUSIONS:
These findings demonstrated that SOPH exposure reduced the number of implanted embryos in a dose-dependent manner and failed the embryo implantation through altering the morphology of uterine and compromising the endometrial receptivity.

Protocol of Sophoricoside

Cell Research

Anti-inflammatory mode of isoflavone glycoside sophoricoside by inhibition of interleukin-6 and cyclooxygenase-2 in inflammatory response.[Pubmed: 12735689]

Arch Pharm Res. 2003 Apr;26(4):306-11.

Soy, high dietary intake for the oriental population, is a main source of isoflavonoids. Sophoricoside (SOP) an isoflavone glycoside was isolated from immature fruits of Sophora japonica (Leguminosae family) and its inhibitory effect on chemical mediators involved in inflammatory response was investigated in this study.
METHODS AND RESULTS:
SOP inhibited the interleukin (IL)-6 bioactivity with an IC50 value of 6.1 microM whereas it had no effects on IL-1beta and TNF-alpha bioactivities. SOP was identified as a selective inhibitor of cyclooxygenase (COX)-2 activity with an IC50 value of 4.4 microM, but did not show inhibitory effect on the synthesis of COX-2. However, SOP had no effect on the production of reactive oxygen species including superoxide anions and nitric oxide. These results revealed that in vitro anti-inflammatory action of SOP is significantly different from that of genistein known as a phytoestrogen of soy products.
CONCLUSIONS:
This experimental study has documented an importance of dietary soy isoflavonoids as multifunctional agents beneficial to human health, and will help to clarify protective mechanisms of SOP against inflammatory conditions.

Animal Research

Effect of Sophoricoside on histomorphology of bone in ovariectomized rats.[Pubmed: 15339615]

The ameliorative effect of sophoricoside on mast cell-mediated allergic inflammation in vivo and in vitro.[Pubmed: 23698058]

Molecules. 2013 May 22;18(5):6113-27.

Sophoricoside exhibits numerous pharmacological effects, including anti- inflammatory and anti-cancer actions, yet the exact mechanism that accounts for the anti-allergic effects of Sophoricoside is not completely understood. The aim of the present study was to elucidate whether and how Sophoricoside modulates the mast cell-mediated allergic inflammation in vitro and in vivo.
METHODS AND RESULTS:
We investigated the pharmacological effects of Sophoricoside on both compound 48/80 or histamine-induced scratching behaviors and 2,4-dinitrochlorobenzene (DNCB)-induced atopic dermatitis in mice. Additionally, to find a possible explanation for the anti-inflammatory effects of Sophoricoside, we evaluated the effects of Sophoricoside on the production of histamine and inflammatory cytokines and activation of nuclear factor-κB (NF-κB) and caspase-1 in phorbol 12-myristate 13-acetate plus calcium ionophore A23187 (PMACI)-stimulated human mast cells (HMC-1). The finding of this study demonstrated that Sophoricoside reduced compound 48/80 or histamine-induced scratching behaviors and DNCB-induced atopic dermatitis in mice. Additionally, Sophoricoside inhibited the production of inflammatory cytokines as well as the activation of NF-κB and caspase-1 in stimulated HMC-1.
CONCLUSIONS:
Collectively, the findings of this study provide us with novel insights into the pharmacological actions of Sophoricoside as a potential molecule for use in the treatment of allergic inflammation diseases.

Zhong Xi Yi Jie He Xue Bao. 2003 May;1(1):44-6.

To evaluate the potential preventive effect of Sophoricoside on bone loss in ovariectomized rats.
METHODS AND RESULTS:
Female SD rats (n=50, 6 months old) were either sham-operated (SHAM group, n=10) or ovariectomized (n=40). Three days after operation, ovariectomized rats were randomly assigned to groups as follows: 10 received Sophoricoside 4 mg.kg(-1).d(-1) (SL group), 10 received Sophoricoside 8 mg.kg(-1).d(-1) (SM group), 10 received Sophoricoside 16 mg.kg(-1).d(-1) (SH group) and 10 were untreated (OVX group). After Sophoricoside were given orally for one month, the histomorphometric parameters in the secondary spongiosa of proximal tibia and lumbar vertebrae were examined. Compared with OVX group, SM and SH two kinds of treatment caused 15.28% and 22.81% increment in percent trabecular area (BV/TV, %) in the secondary spongiosa of proximal tibia, 14.23% and 21.2% increment in lumbar vertebrae. Accordingly in these two groups, there was a significant decrease in trabecular separation (FLAW, microm), but increment in trabecular width (Tb. Th, microm) and conjunction points (JOINT). But in SL group, the preventive effect was not observed.
CONCLUSIONS:
Sophoricoside can be efficient in preventing ovariectomy-induced bone loss in rats.

Sophoricoside Dilution Calculator

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Preparing Stock Solutions of Sophoricoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3128 mL 11.5639 mL 23.1278 mL 46.2556 mL 57.8195 mL
5 mM 0.4626 mL 2.3128 mL 4.6256 mL 9.2511 mL 11.5639 mL
10 mM 0.2313 mL 1.1564 mL 2.3128 mL 4.6256 mL 5.782 mL
50 mM 0.0463 mL 0.2313 mL 0.4626 mL 0.9251 mL 1.1564 mL
100 mM 0.0231 mL 0.1156 mL 0.2313 mL 0.4626 mL 0.5782 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Sophoricoside

Effective bioconversion of sophoricoside to genistein from Fructus sophorae using immobilized Aspergillus niger and Yeast.[Pubmed:25392205]

World J Microbiol Biotechnol. 2015 Jan;31(1):187-97.

In this study, Sophoricoside from Fructus sophorae was highly bioconversed to genistein by co-immobilized Aspergillus niger and Yeast. Bioconversion conditions for genistein were optimized with single-factor experiments. The optimal conditions were as follows: microbial concentration 1.5 x 10(7) cells/mL, wet weight of microorganisms beads 10.0 g/g material, pH 5, ratio of liquid to solid 25:1 (mL/g), temperature 32 degrees C and time 24 h. Under these conditions, a 34.45-fold increase in production of genistein was observed with a bioreactor. Moreover, the antioxidant activities of the extracts from the fermented and untreated F. sophorae were 0.287 +/- 0.11, 0.384 +/- 0.08 mg/mL (IC50) and 1.84 +/- 0.13, 1.28 +/- 0.25 mmol Fe(II)/g, according to the DPPH test and FRAP assay, respectively. The results indicated that the method described in the current work were valuable procedure for the production of genistein, which is of most importance for industrial scale applications as well as food industry.

Modulation of lipogenesis and glucose consumption in HepG2 cells and C2C12 myotubes by sophoricoside.[Pubmed:24352018]

Molecules. 2013 Dec 13;18(12):15624-35.

Sophoricoside, an isoflavone glycoside isolated from Sophora japonica (Leguminosae), has been widely reported as an immunomodulator. In this study, the effects of Sophoricoside on lipogenesis and glucose consumption in HepG2 cells and C2C12 myotubes were investigated. Treatment with Sophoricoside at concentrations of 1-10 muM inhibited lipid accumulation in HepG2 cells in a dose-dependent manner. At the same concentration range, no effect on cell viability was observed in the MTT assay. Inhibition of lipogenesis was associated with the downregulation of SREBP-1a, SREBP-1c, SREBP-2 and their downstream target genes (FAS, ACC, HMGR) as revealed by realtime quantitative PCR. The lipid-lowering effect was mediated via the phosphorylation of AMPK. Further investigation of the activities of this isoflavone showed that Sophoricoside has the capability to increase glucose uptake by C2C12 myotubes. It also effectively inhibited the activities of alpha-glucosidase and alpha-amylase in vitro and remarkably lowered postprandial hyperglycaemia in starch-loaded C57BL6/J mice. These results suggest that Sophoricoside is an effective regulator of lipogenesis and glucose consumption and may find utility in the treatment of obesity and type 2 diabetes.

Anti-inflammatory mode of isoflavone glycoside sophoricoside by inhibition of interleukin-6 and cyclooxygenase-2 in inflammatory response.[Pubmed:12735689]

Arch Pharm Res. 2003 Apr;26(4):306-11.

Soy, high dietary intake for the oriental population, is a main source of isoflavonoids. Sophoricoside (SOP) an isoflavone glycoside was isolated from immature fruits of Sophora japonica (Leguminosae family) and its inhibitory effect on chemical mediators involved in inflammatory response was investigated in this study. SOP inhibited the interleukin (IL)-6 bioactivity with an IC50 value of 6.1 microM whereas it had no effects on IL-1beta and TNF-alpha bioactivities. SOP was identified as a selective inhibitor of cyclooxygenase (COX)-2 activity with an IC50 value of 4.4 microM, but did not show inhibitory effect on the synthesis of COX-2. However, SOP had no effect on the production of reactive oxygen species including superoxide anions and nitric oxide. These results revealed that in vitro anti-inflammatory action of SOP is significantly different from that of genistein known as a phytoestrogen of soy products. This experimental study has documented an importance of dietary soy isoflavonoids as multifunctional agents beneficial to human health, and will help to clarify protective mechanisms of SOP against inflammatory conditions.

Sophoricoside fails the embryo implantation by compromising the uterine endometrial receptivity at implantation "window" of pregnant mice.[Pubmed:24877640]

Chem Biol Interact. 2014 Aug 5;219:57-63.

Sophoricoside (SOPH) is an isoflavone glycoside isolated from the fruits of Sophora japonica. Since its first isolation in 1961, there are rare findings about the effects of SOPH on reproductive system. In the present study, the pregnant mice administrated by different doses of SOPH were used to explore the effect of SOPH on embryo implantation, especially on the endometrial receptivity. The statistical results showed that the number of implanted embryos was gradually declining along the increasing dose of SOPH. When the administrated dose of SOPH was 600 mg/kg per day, great changes were observed in the exposed uterine morphology and up-regulated progesterone receptor (PR) and down-regulated estrogen receptor alpha (ERalpha), E-cadherin, matrix metalloproteinase-2 (MMP-2) and integrin beta3 were also found in SOPH-exposed uterine. These findings demonstrated that SOPH exposure reduced the number of implanted embryos in a dose-dependent manner and failed the embryo implantation through altering the morphology of uterine and compromising the endometrial receptivity.

The ameliorative effect of sophoricoside on mast cell-mediated allergic inflammation in vivo and in vitro.[Pubmed:23698058]

Molecules. 2013 May 22;18(5):6113-27.

Sophoricoside exhibits numerous pharmacological effects, including anti- inflammatory and anti-cancer actions, yet the exact mechanism that accounts for the anti-allergic effects of Sophoricoside is not completely understood. The aim of the present study was to elucidate whether and how Sophoricoside modulates the mast cell-mediated allergic inflammation in vitro and in vivo. We investigated the pharmacological effects of Sophoricoside on both compound 48/80 or histamine-induced scratching behaviors and 2,4-dinitrochlorobenzene (DNCB)-induced atopic dermatitis in mice. Additionally, to find a possible explanation for the anti-inflammatory effects of Sophoricoside, we evaluated the effects of Sophoricoside on the production of histamine and inflammatory cytokines and activation of nuclear factor-kappaB (NF-kappaB) and caspase-1 in phorbol 12-myristate 13-acetate plus calcium ionophore A23187 (PMACI)-stimulated human mast cells (HMC-1). The finding of this study demonstrated that Sophoricoside reduced compound 48/80 or histamine-induced scratching behaviors and DNCB-induced atopic dermatitis in mice. Additionally, Sophoricoside inhibited the production of inflammatory cytokines as well as the activation of NF-kappaB and caspase-1 in stimulated HMC-1. Collectively, the findings of this study provide us with novel insights into the pharmacological actions of Sophoricoside as a potential molecule for use in the treatment of allergic inflammation diseases.

[Effect of Sophoricoside on histomorphology of bone in ovariectomized rats].[Pubmed:15339615]

Zhong Xi Yi Jie He Xue Bao. 2003 May;1(1):44-6.

OBJECTIVE: To evaluate the potential preventive effect of Sophoricoside on bone loss in ovariectomized rats. METHODS: Female SD rats (n=50, 6 months old) were either sham-operated (SHAM group, n=10) or ovariectomized (n=40). Three days after operation, ovariectomized rats were randomly assigned to groups as follows: 10 received Sophoricoside 4 mg.kg(-1).d(-1) (SL group), 10 received Sophoricoside 8 mg.kg(-1).d(-1) (SM group), 10 received Sophoricoside 16 mg.kg(-1).d(-1) (SH group) and 10 were untreated (OVX group). After Sophoricoside were given orally for one month, the histomorphometric parameters in the secondary spongiosa of proximal tibia and lumbar vertebrae were examined. RESULTS: Compared with OVX group, SM and SH two kinds of treatment caused 15.28% and 22.81% increment in percent trabecular area (BV/TV, %) in the secondary spongiosa of proximal tibia, 14.23% and 21.2% increment in lumbar vertebrae. Accordingly in these two groups, there was a significant decrease in trabecular separation (FLAW, microm), but increment in trabecular width (Tb. Th, microm) and conjunction points (JOINT). But in SL group, the preventive effect was not observed. CONCLUSION: Sophoricoside can be efficient in preventing ovariectomy-induced bone loss in rats.

Description

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

Keywords:

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