Asiaticoside

[Description]:

Asiaticoside, a trisaccaride triterpene from Centella asiatica, suppresses TGF-β/Smad signaling through inducing Smad7 and inhibiting TGF-βRI and TGF-βRII in keloid fibroblasts; Asiaticoside shows antioxidant, anti-inflammatory, and anti-ulcer properties.

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> TGF-beta/Smad

Signaling Pathways >> TGF-beta/Smad >> TGF-beta/Smad

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

Research Areas >> Cardiovascular Disease

Natural Products >> Terpenoids and Glycosides

[Target]

TGF-beta/Smad[1]

[In Vitro]

Asiaticoside (0, 100, 250, and 500 mg/L) dose-dependently inhibits keloid fibroblasts proliferation. Asiaticoside (100, 250, and 500 mg/L) decreases the expression of collagen protein and mRNA, reduces the expression of TGF-bRI, TGF-bRII protein, and mRNA, increases the expression of Smad7, but does not affect Smad2, Smad3, Smad4, phosphorylated Smad2, and phosphorylated Smad3 in keloid fibroblasts[1]. Asiaticoside (12.5 and 50, and 25 and 50 µg/mL) prevents endothelial cells from hypoxia-induced inhibition of cell viability and NO production. Asiaticoside (50 µg/mL) also protects endothelial cells from hypoxia-induced apoptosis and upregulates and phosphorylation of AKT/eNOS in hypoxia-exposed HPAECs[2].

[In Vivo]

Asiaticoside (50 mg/kg daily) blocks the development of hypoxic pulmonary hypertension (PH), cardiovascular remodeling and endothelial cell injury in rats with pulmonary hypertension[2]. Asiaticoside (5, 15 or 45 mg/kg, p.o.) improves the learning and memory deficit, protects hippocampi against the impairment, decreases Aβ deposits in the hippocampus, and ameliorates impaired subcellular structure in rats treated with Aβ oligomers[3].

[Cell Assay]

Cells are seeded at a density of 2-9 × 104 cells/mL into 24-well plates for cell viability, 60-mm plates for RNA and protein analysis in DMEM containing 10% FBS (DMEM/10% FBS). After 24 h, medium is removed and cells are placed in serum-free DMEM. After 48 h, different concentrations of Asiaticoside in DMEM/10% FBS are added simultaneously to cells. Control cells are grown in DMEM/10% FBS without the addition of Asiaticoside. At different time points, the fibroblasts are harvested for analysis[1].

[Animal admin]

Rats[3]Sprague-Dawley rats are used to establish the Alzheimer's disease (AD) model. Asiaticoside is administered orally at 5, 15 or 45 mg/kg body weight per day for 7 days. The learning and memory function of the rats are evaluated by the MWM test 7 days after surgery. The swimming pool (180 cm in diameter) is maintained at 22-24°C, and divided into four quadrants with equal size. A hidden platform is placed in the center of one quadrant. Each of the cardinal points of these four quadrants is randomLy selected as the start location. On the pre-test day, rats are allowed to swim freely for 120 sec. During the test (days 1-4), each rat is subjected to 8 trials each day. The trial begins when a rat is placed in the pool, and ended when the rat finds the platform. The escape latency is recorded. If a rat fails to find the platform within 120 sec, the trial is terminated and the escape latency is recorded as 120 sec, and the rat is guided to the platform. On day 5, the swimming path is recorded by a video recording system, and the digital images are analyzed by the water maze software. In addition, the probe test is performed, in which the platform is removed, and the rat is allowed to swim freely in the pool for 120 sec. The swimming time in the target quadrant is recorded[3].

[References]

[1]. Tang B, et al. Asiaticoside suppresses collagen expression and TGF-β/Smad signaling through inducing Smad7 and inhibiting TGF-βRI and TGF-βRII in keloid fibroblasts. h Dermatol Res. 2011 Oct;303(8):563-72.

[2]. Wang X, et al. Effect of asiaticoside on endothelial cells in hypoxia‑induced pulmonary hypertension. Mol Med Rep. 2018 Feb;17(2):2893-2900.

[3]. Zhang Z, et al. Asiaticoside ameliorates β-amyloid-induced learning and memory deficits in rats by inhibiting mitochondrial apoptosis and reducing inflammatory factors. Exp Ther Med. 2017 Feb;13(2):413-420.

[Related Small Molecules]

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
949.4±65.0 °C at 760 mmHg

[ Melting Point ]:
235-238ºC

[ Molecular Formula ]:
C₄₈H₇₈O₁₉

[ Molecular Weight ]:
959.12

[ Flash Point ]:
268.4±27.8 °C

[ PSA ]:
315.21000

[ LogP ]:
8.34

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

[ Index of Refraction ]:
1.606

Click to get detail MSDS

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YU9625000

CHEMICAL NAME :: Urs-12-en-28-oic acid, 2-alpha,3-beta,23-trihydroxy-, O-6-deoxy-alpha-L-mannopyranosyl- (1-4)-o-beta-D-glucopyranosyl-(1-6)-o-beta-D-glucopyr anosyl ester

CAS REGISTRY NUMBER :: 16830-15-2

BEILSTEIN REFERENCE NO. :: 0078195

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C48-H78-O19

MOLECULAR WEIGHT :: 959.26

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg/52W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 32,1463,1972 *** REVIEWS *** TOXICOLOGY REVIEW CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 60,1171,1976

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
YU9625000

Precursor

DownStream

In vitro modulatory effects on three major human cytochrome P450 enzymes by multiple active constituents and extracts of Centella asiatica.

J. Ethnopharmacol. 130(2) , 275-83, (2010)

Centella asiatica (CA) has been widely cultivated as a vegetable or spice in China, Southeast Asia, India, Sri Lanka, Africa, and Oceanic countries and traditionally used for wound healing and maintai...

Factors affecting the content of pentacyclic triterpenes in Centella asiatica raw materials.

Pharm. Biol. 50(12) , 1508-12, (2012)

Pentacyclic triterpenes, mainly, asiatic acid, madecassic acid, asiaticoside, and madecassoside are the active constituents of Centella asitica (L.) Urban. (Apiaceae). These compounds possess various ...

Matrix metalloproteinase, hyaluronidase and elastase inhibitory potential of standardized extract of Centella asiatica.

Pharm. Biol. 51(9) , 1182-7, (2013)

Centella asiatica (L.) Urban (Apiaceae), a valuable herb described in Ayurveda, is used in the indigenous system of medicine as a tonic to treat skin diseases.Centella asiatica methanol extract and it...

Names

Biological Activity

Chemical & Physical Properties

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

Safety Information

Precursor & DownStream

Precursor

DownStream

Articles

Related Compounds