Gentiopicroside

Category	HCV Protease
CAS	20831-76-9
Description	Gentiopicroside is isolated from the roots of Gentiana manshurica Kitag.

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Product Information

Synonyms	Gentiopicrin
IUPAC Name	(3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
Molecular Weight	356.33
Molecular Formula	C16H20O9
Canonical SMILES	C=CC1C(OC=C2C1=CCOC2=O)OC3C(C(C(C(O3)CO)O)O)O
InChI	InChI=1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1
InChIKey	DUAGQYUORDTXOR-GPQRQXLASA-N
Boiling Point	667.8±55.0 °C at 760 mmHg
Melting Point	191°C
Flash Point	247.1±25.0 °C
Purity	99%
Density	1.5±0.1 g/cm3
Solubility	In Vitro: DMSO : ≥ 100 mg/mL(280.65 mM) H2O : 100 mg/mL(280.65 mM;Need ultrasonic) In Vivo: 1.Add each solvent one by one:10% DMSO >> 40%PEG300 >> 5%Tween-80 >> 45% saline Solubility: ≥ 2.08 mg/mL (5.84 mM); Clear solution 2.Add each solvent one by one:10% DMSO >> 90% (20%SBE-β-CDin saline) Solubility: ≥ 2.08 mg/mL (5.84 mM); Clear solution 3.Add each solvent one by one:10% DMSO >> 90%corn oil Solubility: ≥ 2.08 mg/mL (5.84 mM); Clear solution
Appearance	Powder
Application	antimalarial; anti-apoptotic
Storage	Powder: -20°C: 3 years; 4°C: 2 years; In solvent: -80°C: 6 months; -20°C: 1 month
Animal Admin	Mice are randomly divided into 6 groups of 10 pcs each. It is administered by intragastric administration once a day for three consecutive days. Mice in normal control and ethanol control (negative control) receive saline at a dose of 2.5 mL/kg; Mice in the cimetidine control group (positive control) received cimetidine at a dose of 100 mg/kg; Mice in the three gentiopicrin study groups received different doses of gentiopicrin (20, 40, and 80 mg/kg); On the third day, mice in the other groups received 70% ethanol orally at a dose of 0.01 mL/g 1 h after the last intragastric dose, except for mice in the normal control group who received saline. 1 h after induction, euthanize the animal under anesthesia by cervical dislocation, remove and cut the stomach longitudinally. Open the stomach along a large curvature and rinse lightly with ice-cold saline to remove gastric contents, after which the severity of damage to the gastric mucosa is assessed by the gastric ulcer index. Subsequently, the stomach of each animal is cut into two parts, one part of which is stored at -80 °C for biochemical evaluation and the other part is immersed in 4% paraformaldehyde solution for histopathological examination.
Complexity	598
Exact Mass	356.11073221
Index Of Refraction	1.623
In Vitro	Gentiopicroside inhibits P450 activity, IC50 and Ki of CYP2A6 are 61 μM and 8.12 μM, and also slightly inhibits CYP2E1 activity with IC50 of 1.6 mM, but has no inhibitory effect on CYP1A2 and CYP3A4. Gentianosside (12.5, 25 and 50 μM) inhibits RANKL-induced osteoclastic formation in mouse bone marrow macrophages (BMMs) in a dose-dependent manner, blocks the expression of osteoclast-associated proteins, and prevents receptor activators of nuclear factor-kappa B ligands (RANKL)-triggered JNK and NF-κB activation. Gentiopicroside (50 μM) also inhibits RANKL-induced bone resorption.
In Vivo	Gentianosside (20, 40, and 80 mg/kg, po) significantly reduces the gastric ulcer index in mice. Gentianoside (20, 40 and 80 mg/kg) can also reduce levels of HSP-70, TNF-α, IL-6, MDA, and increase GSH levels and SOD activity. Furthermore, gentian picrin normalizes EGF and VEGF levels in mice.
PSA	134.91000
Target	Cytochrome P450; HCV
Vapor Pressure	0.0±4.6 mmHg at 25°C
XLogP3-AA	-1.2