CAS 20874-52-6|Saikosaponin D
Introduction：Basic information about CAS 20874-52-6|Saikosaponin D, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Saikosaponin D | ||
|---|---|---|---|
| CAS Number | 20874-52-6 | Molecular Weight | 780.982 |
| Density | 1.4±0.1 g/cm3 | Boiling Point | 893.7±65.0 °C at 760 mmHg |
| Molecular Formula | C42H68O13 | Melting Point | 256- 259ºC |
| MSDS | ChineseUSA | Flash Point | 494.3±34.3 °C |
Names
| Name | Saikosaponin D |
|---|---|
| Synonym | More Synonyms |
Saikosaponin D BiologicalActivity
| Description | Saikosaponin D is a triterpene saponin isolated from Bupleurum, with anti-inflammatory, anti-bacterial, anti-tumor, and anti-allergic activities; Saikosaponin D inhibits selectin, STAT3 and NF-kB and activates estrogen receptor-β. |
|---|---|
| Related Catalog | Signaling Pathways >>Others >>Estrogen Receptor/ERRNatural Products >>Terpenoids and GlycosidesResearch Areas >>CancerResearch Areas >>Inflammation/ImmunologyResearch Areas >>Infection |
| Target | STAT3 NF-κB ERβ |
| In Vitro | Saikosaponin D (Compound 3) is a triterpene saponin, which inhibits E-selectin, L-selectin and P-selectin binding to THP-1 cells, with IC50s of 1.8 µM, 3.0 µM and 4.3 µM, and such effects are not due to cytotoxic action. Saikosaponin D (1, 5, 10 µM) dose-dependently inhibits the THP-1 adhesion to the HUVECs monolayer activated by TNF-α. Saikosaponin D (30 μM) also inhibits the expression of P-selectin ligand (CD162) in THP-1 cells[1]. Saikosaponin D (5 μM) suppresses the proliferation of HSC-T6 cells induced by H2O2 treatment, reduces the expression levels of α-SMA, TGF-β1, Hyp, COL1 and TIMP-1, and increases MMP-1 expressioon, thus inhibiting H2O2-induced excessive extracellular matrix (ECM) formation, with similar effects to estradiol (E2), and these effects are blocked by ER antagonists. Saikosaponin D also inhibits oxidative stress-induced ROS generation and down reduates MAPK signaling pathway, and the inhibition is also suppressed by ER antagonists[3]. |
| In Vivo | Saikosaponin D (2 mg/kg/day, i.p.) shows a protective effect on overdose of acetaminophen (APAP)-induced liver injury of mice. Saikosaponin D affects APAP metabolism, increases GSH levels but does not alter PPARα activation. Saikosaponin D (2 mg/kg/day, i.p.) also suppresses APAP-induced increases in the expression of STAT3 target genes and pro-inflammatory cytokines and inhibits APAP-induced activation of STAT3 and NF-kB[2]. |
| Cell Assay | Cell viability is assessed by morphology and by reduction of the tetrazolium salt (MTT). Briefly, the THP-1 cells (2 × 105 cells/well) and various concentrations of compounds 1-4 (including Saikosaponin D) are added to the 96-well plates, incubated for 48 h at 37°C, and 5 µL of MTT solution (5 mg/mL in PBS) is added to each well of the 96-well plates. After incubation for 4 h at 37°C, the absorbance is measured at 540 nm using a microplate reader with the reference absorbance at 650 nm[1]. |
| Animal Admin | Mice[2] Male 6- to 7-week-old C57BL6 mice are randomly divided into four groups, vehicle/control, Saikosaponin D (SSd)/control, vehicle/APAP, and SSd/APAP, and killed 4 h or 24 h after single APAP injection. For overdose of acetaminophen (APAP) injection, a typical single dose of 200 mg/kg/day is used. Saikosaponin D, 2 mg/kg once daily is used as the dosing regimen. Saikosaponin D powder is dissolved in a saline solution supplemented with 0.1% Tween 20 and is administered by intraperitoneal injection at a dose of 2 mg/kg/day once daily for five days. Saline solution containing 0.1% Tween 20 without Saikosaponin D is administered as a vehicle. APAP is dissolved in warm saline solution (20 mg/mL) and is injected intraperitoneally 30 minutes after the last Saikosaponin D injection. Saline is injected to mice in the control groups[2]. |
| References | [1]. Jang MJ, et al. Saikosaponin D isolated from Bupleurum falcatum inhibits selectin-mediated cell adhesion. Molecules. 2014 Dec 4;19(12):20340-9. [2]. Liu A, et al. Saikosaponin d protects against acetaminophen-induced hepatotoxicity by inhibiting NF-κB and STAT3 signaling. Chem Biol Interact. 2014 Nov 5;223:80-6. [3]. Que R, et al. Estrogen receptor-β-dependent effects of saikosaponin‑d on the suppression of oxidative stress-induced rat hepatic stellate cell activation. Int J Mol Med. 2018 Mar;41(3):1357-1364. |
Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Boiling Point | 893.7±65.0 °C at 760 mmHg |
| Melting Point | 256- 259ºC |
| Molecular Formula | C42H68O13 |
| Molecular Weight | 780.982 |
| Flash Point | 494.3±34.3 °C |
| Exact Mass | 780.466003 |
| PSA | 207.99000 |
| LogP | 3.65 |
| Vapour Pressure | 0.0±0.6 mmHg at 25°C |
| Index of Refraction | 1.617 |
| InChIKey | KYWSCMDFVARMPN-LCSVLAELSA-N |
| SMILES | CC1OC(OC2CCC3(C)C(CCC4(C)C3C=CC35OCC6(CCC(C)(C)CC63)C(O)CC45C)C2(C)CO)C(O)C(OC2OC(CO)C(O)C(O)C2O)C1O |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1530 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 2,60,1981
Safety Information
| Hazard Codes | Xi |
|---|---|
| Risk Phrases | 36/37/38 |
| Safety Phrases | S26 |
| RTECS | VN3099000 |
| HS Code | 29389090 |
Preparation
Synonyms
| β-D-galactopyranoside, (3β,16α)-13,28-epoxy-16,23-dihydroxyolean-11-en-3-yl 6-deoxy-3-O-β-D-glucopyranosyl- |
| β-D-Galactopyranoside, (3β,16α,17α,18α)-13,28-epoxy-16,23-dihydroxyolean-11-en-3-yl 6-deoxy-3-O-β-D-glucopyranosyl- |
| Saikosaponin BII |
| Saikosaponin D |
| (3β,13α,16α,17α)-16,23-Dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-β-D-glucopyranosyl-β-D-galactopyranoside |
| Fluoro nitroaniline |
| (3β,16α)-16,23-Dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-β-D-glucopyranosyl-β-D-galactopyranoside |
| SAIKOSAPONINB2STANDARD |
| Saikosaponin b2 std. |
| SaikosaponinD |
| Saikosaponian D |
| (3β,16α,17α,18α)-16,23-Dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-β-D-glucopyranosyl-β-D-galactopyranoside |
| β-D-Galactopyranoside, (3β,13α,16α,17α)-13,28-epoxy-16,23-dihydroxyolean-11-en-3-yl 6-deoxy-3-O-β-D-glucopyranosyl- |
