Saikosaponin C

CAS# 20736-08-7

Saikosaponin C

Catalog No. BCN1087----Order now to get a substantial discount!

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Quality Control of Saikosaponin C

Number of papers citing our products

Chemical structure

Saikosaponin C

3D structure

Chemical Properties of Saikosaponin C

Cas No. 20736-08-7 SDF Download SDF
PubChem ID 3037094 Appearance Powder
Formula C48H72O17 M.Wt 921.1
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in methan
SMILES CC1C(C(C(C(O1)OC2C(C(C(OC2(C3CCC4(C(C3(C)C)CCC5(C4C=CC67C5(CC(C8(C6CC(CC8)(C)C)CO7)O)C)C)C)OC9C(C(C(C(O9)CO)O)O)O)CO)O)O)O)O)O
Standard InChIKey IUZOALRTJNKYRZ-ANYCVEQWSA-N
Standard InChI InChI=1S/C48H78O17/c1-22-30(52)33(55)36(58)39(61-22)63-38-35(57)32(54)24(20-50)64-48(38,65-40-37(59)34(56)31(53)23(19-49)62-40)26-9-12-43(6)25(42(26,4)5)10-13-44(7)27(43)11-14-47-28-17-41(2,3)15-16-46(28,21-60-47)29(51)18-45(44,47)8/h11,14,22-40,49-59H,9-10,12-13,15-21H2,1-8H3/t22-,23+,24+,25?,26?,27?,28-,29+,30-,31+,32+,33+,34-,35-,36+,37+,38+,39-,40-,43-,44+,45-,46?,47?,48+/m0/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 Saikosaponin C

The root of Bupleurum chinense DC.

Biological Activity of Saikosaponin C

DescriptionSaikosaponin C exhibits anti-HBV activity, it has the potential for therapeutic angiogenesis but is not suitable for cancer therapy, it also might be a novel therapeutic tool for treating human AD and other neurodegenerative diseases. It inhibited caspase-3 activation and caspase-3-mediated-FAK degradation, induced matrix metalloproteinase-2 (MMP-2)、vascular endothelial growth factor (VEGF) 、the p42/p44 mitogen-activated protein kinase (MAPK, ERK).
TargetsCaspase | FAK | MMP(e.g.TIMP) | VEGFR | MAPK | ERK | PARP | HBV
In vitro

Saikosaponin C inhibits lipopolysaccharide-induced apoptosis by suppressing caspase-3 activation and subsequent degradation of focal adhesion kinase in human umbilical vein endothelial cells.[Pubmed: 24565837]

Biochem Biophys Res Commun. 2014 Mar 14;445(3):615-21.

Bacterial lipopolysaccharide (LPS) is an important mediator of inflammation and a potent inducer of endothelial cell damage and apoptosis. In this study, we investigated the protective effects of Saikosaponin C (SSc), one of the active ingredients produced by the traditional Chinese herb, Radix Bupleuri, against LPS-induced apoptosis in human umbilical endothelial cells (HUVECs).
METHODS AND RESULTS:
LPS triggered caspase-3 activation, which was found to be important in LPS-induced HUVEC apoptosis. Inhibition of caspase-3 also inhibited LPS-induced degradation of focal adhesion kinase (FAK), indicating that caspase-3 is important in LPS-mediated FAK degradation as well as in apoptosis in HUVECs. SSc significantly inhibited LPS-induced apoptotic cell death in HUVECs through the selective suppression of caspase-3. SSc was also shown to rescue LPS-induced FAK degradation and other cell adhesion signals. Furthermore, the protective effects of SSc against LPS-induced apoptosis were abolished upon pretreatment with a FAK inhibitor, highlighting the importance of FAK in SSc activity.
CONCLUSIONS:
Taken together, these results show that SSc efficiently inhibited LPS-induced apoptotic cell death via inhibition of caspase-3 activation and caspase-3-mediated-FAK degradation. Therefore, SSc represents a promising therapeutic candidate for the treatment of vascular endothelial cell injury and cellular dysfunction.

Saikosaponin C induces endothelial cells growth, migration and capillary tube formation.[Pubmed: 15581913]

Life Sci. 2004 Dec 31;76(7):813-26.

Saikosaponin C is one of the saikosaponins that are consisted in a Chinese herb, Radix Bupleuri. Recently, saikosaponins have been reported to have properties of cell growth inhibition, inducing cancer cells differentiation and apoptosis. However, Saikosaponin C had no correlation with cell growth inhibition. In this study, we investigated the role of Saikosaponin C on the growth of endothelial cells and angiogenesis.
METHODS AND RESULTS:
We found that Saikosaponin C yielded a potent effect on inducing human umbilical vein endothelial cells (HUVECs) viability and growth. In addition to inducing endothelial cells growth, Saikosaponin C also induced endothelial cells migration and capillary tube formation. The gene expression or activation of matrix metalloproteinase-2 (MMP-2), vascular endothelial growth factor (VEGF) and the p42/p44 mitogen-activated protein kinase (MAPK, ERK) that correlated with endothelial cells growth, migration and angiogenesis were also induced by Saikosaponin C.
CONCLUSIONS:
From these results, we suggest that Saikosaponin C may have the potential for therapeutic angiogenesis but is not suitable for cancer therapy.

Protocol of Saikosaponin C

Kinase Assay

Metabolism of saikosaponin c and naringin by human intestinal bacteria.[Pubmed: 18982483]

Arch Pharm Res. 1997 Oct;20(5):420-4.


METHODS AND RESULTS:
By human intestinal bacteria, Saikosaponin C was transformed to four metabolites, prosaikogenin E1 (E1) prosaikogenin E2 (E2), prosaikogenin E3 (E3) and saikogenin E. Metabolic time course of Saikosaponin C was as follows; in early time, Saikosaponin C was converted to E1 and E2, and then these were transformed to saikogenin E via E3. Also, this metabolic pathway was similar to the metabolism of Saikosaponin C by rat intestinal bacteria.Bacteroides JY-6 andBacteroides YK-4, the bacteria isolated from human intestinal bacteria, could transform saiko-saponin c to E via E1 (or E2) and E3. However, these bacteria were not able to directly transform E1 and E2 to saikogenin E.
CONCLUSIONS:
Naringin was mainly transformed to naringenin by human intestinal bacteria. The minor metabolic pathway transformed naringin to naringenin via prunin. By JY-6 or YK-4, naringin was metabolized to naringenin only via prunin.

Cell Research

Cytotoxicity and anti-hepatitis B virus activities of saikosaponins from Bupleurum species.[Pubmed: 14531019]

Planta Med. 2003 Aug;69(8):705-9.

Saikosaponins, the main active constituents of Bupleurum spp., have been shown to possess immunomodulatory, hepatoprotective, anti-tumor and anti-viral activities. In this study, saikosaponins a, c and d were evaluated for cytotoxicity and anti-hepatitis B virus ( HBV) activities.
METHODS AND RESULTS:
Results showed that, with the exception of saikosaponins a and d, HBV-transfected human hepatoma cells (2.2.15 cells) cultured with Saikosaponin C showed a significantly lower level of HBeAg in culture medium. Saikosaponin C also possessed activity in inhibiting HBV DNA replication; this inhibitory effect was not due to the cytotoxicity of Saikosaponin C or its effect on 2.2.15 cell proliferation. Although saikosaponin d exhibited cytotoxicity on 2.2.15 cells, it failed to inhibit HBV multiplication. The cytotoxicity of saikosaponin d against HepG2 human hepatocellular carcinoma cells was due to the induction of apoptosis through the activation of caspases 3 and 7, which subsequently resulted in poly-ADP-ribose-polymerase (PARP) cleavage. DNA fragmentation was clearly noted at more than 6 h after HepG2 cells exposure to saikosaponin d.
CONCLUSIONS:
The present study concludes that Saikosaponin C exhibits anti-HBV activity and saikosaponin d possesses potent cytotoxicity against human hepatocellular carcinoma cells.

Structure Identification
Molecules. 2016 Jan 28;21(2):153.

Binding between Saikosaponin C and Human Serum Albumin by Fluorescence Spectroscopy and Molecular Docking.[Pubmed: 26828474 ]

Saikosaponin C (SSC) is one of the major active constituents of dried Radix bupleuri root (Chaihu in Chinese) that has been widely used in China to treat a variety of conditions, such as liver disease, for many centuries.
METHODS AND RESULTS:
The binding of SSC to human serum albumin (HSA) was explored by fluorescence, circular dichroism (CD), UV-vis spectrophotometry, and molecular docking to understand both the pharmacology and the basis of the clinical use of SSC/Chaihu. SSC produced a concentration-dependent quenching effect on the intrinsic fluorescence of HSA, accompanied by a blue shift in the fluorescence spectra. The Stern-Volmer equation showed that this quenching was dominated by static quenching. The binding constant of SSC with HSA was 3.72 × 103 and 2.99 × 103 L·mol(-1) at 26 °C and 36 °C, respectively, with a single binding site on each SSC and HSA molecule. Site competitive experiments demonstrated that SSC bound to site I (subdomain IIA) and site II (subdomain IIIA) in HSA. Analysis of thermodynamic parameters indicated that hydrogen bonding and van der Waals forces were mostly responsible for SSC-HSA association. The energy transfer efficiency and binding distance between SSC and HSA was calculated to be 0.23 J and 2.61 nm at 26 °C, respectively.
CONCLUSIONS:
Synchronous fluorescence and CD measurements indicated that SSC affected HSA conformation in the SSC-HSA complex. Molecular docking supported the experimental findings in conformational changes, binding sites and binding forces, and revealed binding of SSC at the interface between subdomains IIA-IIB.

Saikosaponin C Dilution Calculator

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Saikosaponin C Molarity Calculator

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Preparing Stock Solutions of Saikosaponin C

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.0857 mL 5.4283 mL 10.8566 mL 21.7132 mL 27.1415 mL
5 mM 0.2171 mL 1.0857 mL 2.1713 mL 4.3426 mL 5.4283 mL
10 mM 0.1086 mL 0.5428 mL 1.0857 mL 2.1713 mL 2.7141 mL
50 mM 0.0217 mL 0.1086 mL 0.2171 mL 0.4343 mL 0.5428 mL
100 mM 0.0109 mL 0.0543 mL 0.1086 mL 0.2171 mL 0.2714 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 Saikosaponin C

Cytotoxicity and anti-hepatitis B virus activities of saikosaponins from Bupleurum species.[Pubmed:14531019]

Planta Med. 2003 Aug;69(8):705-9.

Saikosaponins, the main active constituents of Bupleurum spp., have been shown to possess immunomodulatory, hepatoprotective, anti-tumor and anti-viral activities. In this study, saikosaponins a, c and d were evaluated for cytotoxicity and anti-hepatitis B virus ( HBV) activities. Results showed that, with the exception of saikosaponins a and d, HBV-transfected human hepatoma cells (2.2.15 cells) cultured with Saikosaponin C showed a significantly lower level of HBeAg in culture medium. Saikosaponin C also possessed activity in inhibiting HBV DNA replication; this inhibitory effect was not due to the cytotoxicity of Saikosaponin C or its effect on 2.2.15 cell proliferation. Although saikosaponin d exhibited cytotoxicity on 2.2.15 cells, it failed to inhibit HBV multiplication. The cytotoxicity of saikosaponin d against HepG2 human hepatocellular carcinoma cells was due to the induction of apoptosis through the activation of caspases 3 and 7, which subsequently resulted in poly-ADP-ribose-polymerase (PARP) cleavage. DNA fragmentation was clearly noted at more than 6 h after HepG2 cells exposure to saikosaponin d. The present study concludes that Saikosaponin C exhibits anti-HBV activity and saikosaponin d possesses potent cytotoxicity against human hepatocellular carcinoma cells.

Saikosaponin C induces endothelial cells growth, migration and capillary tube formation.[Pubmed:15581913]

Life Sci. 2004 Dec 31;76(7):813-26.

Saikosaponin C is one of the saikosaponins that are consisted in a Chinese herb, Radix Bupleuri. Recently, saikosaponins have been reported to have properties of cell growth inhibition, inducing cancer cells differentiation and apoptosis. However, Saikosaponin C had no correlation with cell growth inhibition. In this study, we investigated the role of Saikosaponin C on the growth of endothelial cells and angiogenesis. We found that Saikosaponin C yielded a potent effect on inducing human umbilical vein endothelial cells (HUVECs) viability and growth. In addition to inducing endothelial cells growth, Saikosaponin C also induced endothelial cells migration and capillary tube formation. The gene expression or activation of matrix metalloproteinase-2 (MMP-2), vascular endothelial growth factor (VEGF) and the p42/p44 mitogen-activated protein kinase (MAPK, ERK) that correlated with endothelial cells growth, migration and angiogenesis were also induced by Saikosaponin C. From these results, we suggest that Saikosaponin C may have the potential for therapeutic angiogenesis but is not suitable for cancer therapy.

Saikosaponin C inhibits lipopolysaccharide-induced apoptosis by suppressing caspase-3 activation and subsequent degradation of focal adhesion kinase in human umbilical vein endothelial cells.[Pubmed:24565837]

Biochem Biophys Res Commun. 2014 Mar 14;445(3):615-21.

Bacterial lipopolysaccharide (LPS) is an important mediator of inflammation and a potent inducer of endothelial cell damage and apoptosis. In this study, we investigated the protective effects of Saikosaponin C (SSc), one of the active ingredients produced by the traditional Chinese herb, Radix Bupleuri, against LPS-induced apoptosis in human umbilical endothelial cells (HUVECs). LPS triggered caspase-3 activation, which was found to be important in LPS-induced HUVEC apoptosis. Inhibition of caspase-3 also inhibited LPS-induced degradation of focal adhesion kinase (FAK), indicating that caspase-3 is important in LPS-mediated FAK degradation as well as in apoptosis in HUVECs. SSc significantly inhibited LPS-induced apoptotic cell death in HUVECs through the selective suppression of caspase-3. SSc was also shown to rescue LPS-induced FAK degradation and other cell adhesion signals. Furthermore, the protective effects of SSc against LPS-induced apoptosis were abolished upon pretreatment with a FAK inhibitor, highlighting the importance of FAK in SSc activity. Taken together, these results show that SSc efficiently inhibited LPS-induced apoptotic cell death via inhibition of caspase-3 activation and caspase-3-mediated-FAK degradation. Therefore, SSc represents a promising therapeutic candidate for the treatment of vascular endothelial cell injury and cellular dysfunction.

Binding between Saikosaponin C and Human Serum Albumin by Fluorescence Spectroscopy and Molecular Docking.[Pubmed:26828474]

Molecules. 2016 Jan 28;21(2):153.

Saikosaponin C (SSC) is one of the major active constituents of dried Radix bupleuri root (Chaihu in Chinese) that has been widely used in China to treat a variety of conditions, such as liver disease, for many centuries. The binding of SSC to human serum albumin (HSA) was explored by fluorescence, circular dichroism (CD), UV-vis spectrophotometry, and molecular docking to understand both the pharmacology and the basis of the clinical use of SSC/Chaihu. SSC produced a concentration-dependent quenching effect on the intrinsic fluorescence of HSA, accompanied by a blue shift in the fluorescence spectra. The Stern-Volmer equation showed that this quenching was dominated by static quenching. The binding constant of SSC with HSA was 3.72 x 10(3) and 2.99 x 10(3) L.mol(-1) at 26 degrees C and 36 degrees C, respectively, with a single binding site on each SSC and HSA molecule. Site competitive experiments demonstrated that SSC bound to site I (subdomain IIA) and site II (subdomain IIIA) in HSA. Analysis of thermodynamic parameters indicated that hydrogen bonding and van der Waals forces were mostly responsible for SSC-HSA association. The energy transfer efficiency and binding distance between SSC and HSA was calculated to be 0.23 J and 2.61 nm at 26 degrees C, respectively. Synchronous fluorescence and CD measurements indicated that SSC affected HSA conformation in the SSC-HSA complex. Molecular docking supported the experimental findings in conformational changes, binding sites and binding forces, and revealed binding of SSC at the interface between subdomains IIA-IIB.

Metabolism of saikosaponin c and naringin by human intestinal bacteria.[Pubmed:18982483]

Arch Pharm Res. 1997 Oct;20(5):420-4.

By human intestinal bacteria, Saikosaponin C was transformed to four metabolites, prosaikogenin E1 (E1) prosaikogenin E2 (E2), prosaikogenin E3 (E3) and saikogenin E. Metabolic time course of Saikosaponin C was as follows; in early time, Saikosaponin C was converted to E1 and E2, and then these were transformed to saikogenin E via E3. Also, this metabolic pathway was similar to the metabolism of Saikosaponin C by rat intestinal bacteria.Bacteroides JY-6 andBacteroides YK-4, the bacteria isolated from human intestinal bacteria, could transform saiko-saponin c to E via E1 (or E2) and E3. However, these bacteria were not able to directly transform E1 and E2 to saikogenin E. Naringin was mainly transformed to naringenin by human intestinal bacteria. The minor metabolic pathway transformed naringin to naringenin via prunin. By JY-6 or YK-4, naringin was metabolized to naringenin only via prunin.

Description

Saikosaponin C is a bioactive component found in radix bupleuri, targets amyloid beta and tau in Alzheimer's disease. Saikosaponin C inhibits the secretion of both Aβ1-40 and Aβ1-42, and suppresses abnormal tau phosphorylation, but shows no effect on BACE1 activity and expression.

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