Swertiamarin

Names

[ Name ]:
Swertiamarin

[Synonym ]:
MFCD07783984
(4aR,5R,6S)-5-ethenyl-4a-hydroxy-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl β-D-glucopyranoside
1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(β-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-4a-hydroxy-, (4aR,5R,6S)-
(4aR,5R,6S)-4a-Hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one
(4aR,5R,6S)-5-Ethenyl-4a-hydroxy-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyr-6-yl-β-D-glucopyranoside
4,4a,5,6-Tetrahydro-4aa-hydroxy-1-oxo-5b-vinyl-1H,3H-pyrano[3,4-c]pyran-6-yl b-D-Glucopyranoside
(4aR,5R,6S)-4a-Hydroxy-1-oxo-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl β-D-glucopyranoside
1H,3H-Pyrano(3,4-c)pyran-1-one, 5-ethenyl-6-(β-d-glucopyranosyloxy)-4,4a,5,6-tetrahydro-4a-hydroxy-, (4aR,5R,6S)-
Swertiamarin
[4aR-(4aa,5b,6a)]-5-Ethenyl-6-(b-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-4a-hydroxy-1H,3H-pyrano[3,4-c]pyran-1-one

Biological Activity

[Description]:

Swertiamarin, a secoiridoid glycoside found in genera of Enicostemma Species, confers anti-hyperglycemic and anti-hyperlipidemic effects[1].

[Related Catalog]:

Research Areas >> Cancer

[References]

[1]. Patel N, et al. Curr Drug Targets. 2018;19(16):1958-1967. doi: 10.2174/1389450119666180406113428.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
649.3±55.0 °C at 760 mmHg

[ Melting Point ]:
111ºC

[ Molecular Formula ]:
C₁₆H₂₂O₁₀

[ Molecular Weight ]:
374.340

[ Flash Point ]:
237.7±25.0 °C

[ Exact Mass ]:
374.121307

[ PSA ]:
155.14000

[ LogP ]:
-3.15

[ Vapour Pressure ]:
0.0±4.4 mmHg at 25°C

[ Index of Refraction ]:
1.626

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ1366700

CHEMICAL NAME :: 1H,3H-Pyrano(3,4-c)pyran-1-one, 4,4a,5,6-tetrahydro-5-ethenyl-6-(beta-d-glucopyranosy loxy)-4a-hydroxy-, (4aR-(4a-alpha,5-beta,6-alpha))-

CAS REGISTRY NUMBER :: 17388-39-5

BEILSTEIN REFERENCE NO. :: 0055278

LAST UPDATED :: 199806

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C16-H22-O10

MOLECULAR WEIGHT :: 374.38

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 13,464,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >8 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 13,464,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 13,464,1982

Safety Information

[ Hazard Codes ]:
C

[ Risk Phrases ]:
R23:Toxic by inhalation. R34:Causes burns.

[ Safety Phrases ]:
S26-S36-S45

[ RIDADR ]:
UN 1789

[ WGK Germany ]:
3.0

[ RTECS ]:
UQ1366700

[ Packaging Group ]:
III

[ Hazard Class ]:
8

Articles

Development and validation of a LC-ESI-MS/MS method for the determination of swertiamarin in rat plasma and its application in pharmacokinetics.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 879(19) , 1653-8, (2011)

A new LC-ESI-MS/MS assay method has been developed and validated for the quantification of swertiamarin, a representative bioactive substance of Swertia plants, in rat plasma using gentiopicroside, an...

Hypoglycemic activity of C-glycosyl flavonoid from Enicostemma hyssopifolium.

Pharm. Biol. 49(4) , 383-91, (2011)

Enicostemma hyssopifolium Verdoon (Gentianaceae) has been documented for various therapeutic effects in traditional systems of medicine; the hypoglycemic and hypolipidemic activities are also well rep...

Antihyperlipidaemic activity of swertiamarin, a secoiridoid glycoside in poloxamer-407-induced hyperlipidaemic rats.

J. Nat. Med. 63(4) , 437-42, (2009)

We have investigated antihyperlipidaemic effect of swertiamarin (50 mg/kg, oral once) isolated from the perennial herb Enicostemma littorale Blume in poloxamer 407 (P-407)-induced hyperlipidaemic rats...

Related Compounds

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