ChemicalBook CAS DataBase List 17388-39-5

17388-39-5

Name	Swertiamarine
CAS	17388-39-5
Molecular Formula	C16H22O10
MDL Number	MFCD07783984
Molecular Weight	374.34
MOL File	17388-39-5.mol

Synonyms

SWERTIAMAIN SWERTIAMARIN (4ar-(4a-alpha,5-beta,6-alpha))-ranosyloxy)-4a-hydroxy 1h,3h-pyrano(3,4-c)pyran-1-one,4,4a,5,6-tetrahydro-5-ethenyl-6-(beta-d-glucopy 1H,3H-Pyrano[3,4-c]pyran-1-one,4,4.alpha.,5,6-tetrahydro-5-ethenyl-6-(.beta.-D-glucopyranosyloxy)-4.alpha.-hydroxy-,[4ar-(4.alpha.-.alpha.,5-.beta.,D-.alpha.)]- 3H-Pyrano[3,4-c]pyran-1-one,4,4.alpha.,5,6-tetrahydro-5-ethenyl-6-(.beta.-D-glucopyranosyloxy)-4.1H 4-c)pyran-1-one,4,4a,5,6-tetrahydro-5-ethenyl-6-(beta-d-glucopyranosyloxy)-4a-hydroxy-3h-pyrano(1 Swertiamarin(6CI,7CI,8CI) Swertiamarine Swertiamaroside SWERTIAMARIN, 98+% BY HPLC Swertiamarin std. SWERTIAMARIN(P) (5R,6S)-5-Ethenyl-4a-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[5,4-c]pyran-1-one glucopyranosyloxy)-4,4a,5,6-tetrahydro-4a-hydroxy-,(4aR,5R, 6S)- Swertiamarin，Swertiamarine，Swertiamaroside (4aR)-4aα-Hydroxy-5β-vinyl-6α-(β-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one 4aα-Hydroxy-6α-(β-D-glucopyranosyloxy)-5β-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one 6α-(β-D-Glucopyranosyloxy)-4,4a,5,6-tetrahydro-4aα-hydroxy-5β-vinyl-1H,3H-pyrano[3,4-c]pyran-1-one

Chemical Properties

Melting point	113-114°
alpha	D20 -127° (c = 1 in 96% ethanol)
Boiling point	649.3±55.0 °C(Predicted)
density	1.57±0.1 g/cm3(Predicted)
storage temp.	Sealed in dry,Store in freezer, under -20°C
solubility	DMSO : 250 mg/mL (667.84 mM; Need ultrasonic)
form	neat
pka	11.56±0.60(Predicted)
color	White to Yellow to Orange
λmax	238nm(MeOH)(lit.)
Merck	14,9010
BRN	55278
Stability:	Hygroscopic
Major Application	metabolomics vitamins, nutraceuticals, and natural products
InChIKey	HEYZWPRKKUGDCR-QBXMEVCASA-N
SMILES	OC[C@H]1O[C@@H](O[C@@H]2OC=C3C(=O)OCC[C@@]3(O)[C@H]2C=C)[C@H](O)[C@@H](O)[C@@H]1O
CAS DataBase Reference	17388-39-5(CAS DataBase Reference)

Safety Data

Safety Statements	24/25 less more
WGK Germany	3
RTECS	UQ1366700
HS Code	29389090
Storage Class	11 - Combustible Solids
Toxicity	mouse,LD50,intraperitoneal,> 8gm/kg (8000mg/kg),BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Zhongcaoyao. Chinese Traditional and Herbal Medicine. Vol. 13, Pg. 464, 1982. less more

Hazard Information

Chemical Properties

White crystals, easily soluble in water, methanol, and ethanol, almost insoluble in chloroform, ether, and petroleum ether, derived from Gentiana macrophylla (Tibet), Swertia japonica, Green Leaf Gallbladder, and Houttuynia cordata.

Uses

Swertimarine is an extract from Enicostemma littorale which is an herb used in the treatment of type 1 and 2 diabetes. Used to sensitize the cells to hypolipidemic conditions and insulin.

Definition

ChEBI: Swertiamarin is a glycoside.

Biological Activity

Swertiamarin has shown potential as antiatherogenic agent by inhibiting HMG-CoA reductase activity in high cholesterol fed rats. The high cholesterol fed rats treated with Swertiamarin showed prevention of increased serum total cholesteroltriglyceridesLDLs and VLDLs.

in vivo

Swertiamarin (50, 75 mg/kg; once daily; 7 days; p.o.) has a lipid-lowering effect in hypercholesterolemic rats^[1]. Swertiamarin (100, 200 mg/kg; once daily; 8 weeks; i.g.) has antioxidant and hepatoprotective effects on carbon tetrachloride induced rat hepatotoxicity through the Nrf2/HO-1 pathway^[2]. Swertiamarin (2, 5, 10 mg/kg; once daily; 2 weeks; p.o.) prevents bone erosion in arthritis rats by regulating RANKL/RANK/OPG signaling transduction^[3]. Swertiamarin (2, 5, 10 mg/kg; once daily; 2 weeks; p.o.) attenuates inflammatory mediators by regulating NF - κ B/I, κ B, and JAK2/STAT3 transcription factors in adjuvant induced arthritis rats^[4].

Animal Model:	Male Sprague Dawley (SD) rats with hypercholesterolemia induced by supplementing a diet rich in cholesterol^[1].
Dosage:	50, 75 mg/kg
Administration:	Oral gavage (p.o.); once daily; 7 days
Result:	Reduced serum total cholesterol, triglyceride concentration and atherosclerosis index.

Animal Model:	Male Sprague Dawley (SD) rat model of liver injury induced by CCl₄^[2].
Dosage:	100, 200 mg/kg
Administration:	i.g. ; once daily; 8 weeks
Result:	Reduced the levels of serum marker enzymes ALT, AST, and ALP representing liver damage, and restored antioxidant enzyme activity and GSH content in rat liver.

Animal Model:	Induced arthritis rat model by intradermal injection of 0.1ml Freund's complete adjuvant (FCA) in 1ml paraffin oil into the right hind paw of rats^[3]^[4].
Dosage:	2, 5, 10 mg/kg
Administration:	Oral gavage (p.o.); once daily; 2 weeks
Result:	Reduced calcium and TRAP, ACP, and ALP levels in serum and urine of arthritis rats, and increased phosphorus and collagen levels^[3]. Inhibited paw thickness, lysosomal enzyme levels, and increased body weight in rats^[4].

Spectrum Detail

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