Madecassoside

Names

[ Name ]:
Madecassoside

[Synonym ]:
Asiaticoside A
MADESOIDE
RederMic
6-Deoxy-α-L-mannopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-1-O-[(2α,3β,6β,14β)-2,3,6,23-tetrahydroxy-28-oxours-12-en-28-yl]-β-D-glucopyranose
β-D-Glucopyranose, O-6-deoxy-α-L-mannopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-1-O-[(2α,3β,6β,14β)-2,3,6,23-tetrahydroxy-28-oxours-12-en-28-yl]-
MADESOSIDE
Madecassoside

Biological Activity

[Description]:

Madecassoside is a pentacyclic triterpene isolated from Centella asitica (L.), as an anti-inflammatory, anti-oxidative activities and anti-aging agent. [1]In vitro: Madecassoside exhibit significant anti-proliferative and anti-invasive effect in HGF-induced HepG2 and SMMC-77 cells. Madecassoside inhibit the HGF-induced activation of cMET-PKC-ERK1/2-COX-2-PGE2cascade. [1]In vivo: Administration of madecassoside, p.o. , exhibit a direct anti-PF effect in mice. Madecassoside increase the expression of hepatocyte growth factor (HGF) in colon tissues, and HGF receptor antagonists attenuated its anti-PF effect. madecassoside in mice are not mediated by its metabolites or itself after absorption into blood. Instead, madecassoside increases the activity of PPAR-γ, which subsequently increases HGF expression in colonic epithelial cells. [2] The reference for administration is 12 mg/kg. [3]

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Terpenoids and Glycosides

Research Areas >> Others

[References]

[1]. Zexin Li et al. Madecassoside suppresses proliferation and invasiveness of HGF-induced human hepatocellular carcinoma cells via PKC-cMET-ERK1/2-COX-2-PGE2 pathway. Int Immunopharmacol. 2016 Apr;33:24-32.

[2]. Xia Y et al. Madecassoside ameliorates bleomycin-induced pulmonary fibrosis in mice through promoting the generation of hepatocyte growth factor via PPAR-γ in colon. Br J Pharmacol. 2016 Apr;173(7):1219-35

[3]. Su Z et al. Protective effects of madecassoside against Doxorubicin induced nephrotoxicity in vivo and in vitro. Sci Rep. 2015 Dec 14

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
1043.6±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄₈H₇₈O₂₀

[ Molecular Weight ]:
975.121

[ Flash Point ]:
295.8±27.8 °C

[ Exact Mass ]:
974.508667

[ PSA ]:
335.44000

[ LogP ]:
1.88

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

[ Index of Refraction ]:
1.637

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
H2O: soluble1mg/mL, clear, colorless

Safety Information

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
YU9625000

Articles

Contact dermatitis due to Centella asiatica.

Contact Dermatitis 62(1) , 54-5, (2010)

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 ...

In vitroinhibitory effects of asiaticoside and madecassoside on human cytochrome P450

Toxicol. In Vitro 25(4) , 890-6, (2011)

The inhibitory effects and types of inhibition of asiaticoside and madecassoside on human CYPs were studied in vitro using recombinant human CYPs. The median inhibitory concentrations (IC 50) of asiat...

Related Compounds

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