Chikusetsusaponin IVa

Names

[ Name ]:
Chikusetsusaponin IVa

[Synonym ]:
Chikusetsusaponin
Chikusetsusaponin Iva
1-O-[(3α,5ξ,9ξ)-3-(β-D-Glucopyranuronosyloxy)-28-oxoolean-12-en-28-yl]-β-D-glucopyranose
GLUCOPYRANOSIDURONIC ACID
Silphioside G
Chikusetsu saponin Ⅳa
β-D-Glucopyranose, 1-O-[(3α,5ξ,9ξ)-3-(β-D-glucopyranuronosyloxy)-28-oxoolean-12-en-28-yl]-
β-D-Glucopyranose, 1-O-[(3β)-3-(β-D-glucopyranuronosyloxy)-28-oxoolean-12-en-28-yl]-
Chikusetsu Saponin IVa
1-O-[(3β)-3-(β-D-Glucopyranuronosyloxy)-28-oxoolean-12-en-28-yl]-β-D-glucopyranose
Calenduloside F
Chikusetsusaponin IV

Biological Activity

[Description]:

Chikusetsusaponin IVa a major active ingredient of triterpenoid saponins, exerts antithrombotic effects, including minor hemorrhagic events. This appears to be important for the development of new therapeutic agents. a novel AMPK activator that is capable of bypassing defective insulin signalling and could be useful for the treatment of T2DM or other metabolic disorders.IC50 Value: 199.4 ± 9.1 μM (inhibiting thrombin-induced fibrinogen clotting) Target: In vitro: Using biochemical and pharmacological methods, it proves that chikusetsusaponin IVa prolongs the recalcification time, prothrombin time, activated partial thromboplastin time, and thrombin time of normal human plasma in a dose-dependent manner; inhibits the amidolytic activity of thrombin and factor Xa upon synthetic substrates S2238 and S2222; inhibits thrombin-induced fibrinogen clotting (50% inhibition concentration, 199.4 ± 9.1 μM); inhibits thrombin- and collagen-induced platelet aggregation. Chikusetsusaponin IVa can also preferentially inhibits thrombin in a competitive manner (K(i)=219.6 μM) [1]. Chikusetsusaponin IVa suppresses the production of iNOS, COX-2, IL-1β, IL-6, and TNF-α in LPS-stimulated THP-1 cells likely by inhibiting NF-κB activation and ERK, JNK, and p38 signal pathway phosphorylation [2].In vivo: Studies were performed on type 2 diabetic mellitus (T2DM) rats given CHS for 28 days to test the antihyperglycemic activity. Oral administration of CHS dose-dependently increased the level of serum insulin and decreased the rise in blood glucose level [3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Terpenoids and Glycosides

Research Areas >> Others

[References]

[1]. Wang H, et al.Inhibitory effects of Chikusetsusaponin IVa on lipopolysaccharide-induced pro-inflammatory responses in THP-1 cells. Int J Immunopathol Pharmacol. 2015 Jul 8.

[2]. Cui J, et al. Insulinotropic effect of Chikusetsu saponin IVa in diabetic rats and pancreatic β-cells. J Ethnopharmacol. 2015 Apr 22;164:334-9.

[3]. Li Y, et al. Chikusetsu saponin IVa regulates glucose uptake and fatty acid oxidation: implications in antihyperglycemic and hypolipidemic effects. J Pharm Pharmacol. 2015 Jul;67(7):997-1007.

[4]. Dahmer T, et al. Antithrombotic effect of chikusetsusaponin IVa isolated from Ilex paraguariensis (Maté). J Med Food. 2012 Dec;15(12):1073-80.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
873.3±65.0 °C at 760 mmHg

[ Melting Point ]:
218-220 ºC (methanol , water )

[ Molecular Formula ]:
C₄₂H₆₆O₁₄

[ Molecular Weight ]:
794.965

[ Flash Point ]:
255.6±27.8 °C

[ Exact Mass ]:
794.445251

[ PSA ]:
232.90000

[ LogP ]:
6.37

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.611

Safety Information

[ Safety Phrases ]:
24/25

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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