Saikosaponin D

Names

[ CAS No. ]:
20874-52-6

[ Name ]:
Saikosaponin D

[Synonym ]:
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-

Biological Activity

[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/ERR

Natural Products >> Terpenoids and Glycosides

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Research 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.

[Related Small Molecules]

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

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VN3099000

CHEMICAL NAME :: Saikosaponins

CAS REGISTRY NUMBER :: 20874-52-6

LAST UPDATED :: 199801

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C42-H68-O13

MOLECULAR WEIGHT :: 781.10

HEALTH HAZARD DATA

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

Precursor & DownStream

Precursor

DownStream

Preparation

Related Compounds

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