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Madecassoside

Catalog Number
ACM34540222-1
CAS
34540-22-2
Structure
IUPAC Name
[6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] 8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
Synonyms
O-6-Deoxy-alpha-L-mannopyranosyl-(1.4)-O-beta-D-glucopyranosyl-(1.6)-beta-D-glucopyranosyl (2alpha,3beta,4alpha,6beta)-2,3,6,23-tetrahydroxyurs-12-en-28-oate
Molecular Weight
975.13
Molecular Formula
C48H78O20
Canonical SMILES
CC1CCC2(CCC3(C(=CCC4C3(CC(C5C4(CC(C(C5(C)CO)O)O)C)O)C)C2C1C)C)C(=O)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)O)O)O)O
InChI
InChI=1S/C48H78O20/c1-19-10-11-48(13-12-46(6)22(28(48)20(19)2)8-9-27-44(4)14-24(52)39(61)45(5,18-50)38(44)23(51)15-47(27,46)7)43(62)68-42-35(59)32(56)30(54)26(66-42)17-63-40-36(60)33(57)37(25(16-49)65-40)67-41-34(58)31(55)29(53)21(3)64-41/h8,19-21,23-42,49-61H,9-18H2,1-7H3
InChI Key
BNMGUJRJUUDLHW-UHFFFAOYSA-N
Flash Point
295.8°C
Purity
98%
Density
1.47 g/cm³
Solubility
water, 18.13 mg/L @ 25 °C (est)
Appearance
White-beige powder
Active Content
95%
Physical State
Solid
Typical Applications
Use as antioxidant.
Use as anti-inflammatory agent.
Spec Sheet
Case Study

Distribution and Metabolism of Madecassoside in Vivo

Distribution and Metabolism of Madecassoside <em>in Vivo</em> Leng, Dan-dan, et al. Journal of ethnopharmacology 150.2 (2013): 601-608.

Centella Asiatica is a commonly used herb in traditional Chinese medicine for the treatment of wounds, keloids, and scars. Madecassoside is the primary active compound in this herb, with a higher content than other triterpenoid components. Understanding the pharmacokinetic characteristics of madecassoside will aid in its development as a therapeutic agent.
Sprague-Dawley rats were administered madecassoside (100 mg/kg) via intravenous injection and oral administration. After a single oral dose, madecassoside was widely distributed in the rat's heart, liver, spleen, lungs, and kidneys, with relatively higher concentrations found in the liver and kidneys. The excretion of madecassoside in bile, urine, and feces was 7.16% (0-12 h), 0.25% (0-72 h), and 24.68% (0-72 h), respectively. The results suggest that hydroxylated madecassoside may primarily be excreted via its metabolites. Co-administration with digoxin or probenecid significantly reduced the excretion of hydroxylated madecassoside in bile in its parent form, indicating that P-glycoprotein and multidrug resistance-associated proteins may be involved in the hepatic and biliary elimination of hydroxylated madecassoside. The existence of enterohepatic circulation was confirmed through the rat model, and the biphasic plasma and tissue concentration-time curves indicated the presence of the drug. Additionally, three metabolites of hydroxylated madecassoside were identified in the rat feces, and potential metabolic pathways were proposed.

Neuroprotective Effects of Madecassoside on MPTP-Induced Early Parkinson's Disease in Rats

Neuroprotective Effects of Madecassoside on MPTP-Induced Early Parkinson's Disease in Rats Xu, Chang-Liang, et al. Fitoterapia 90 (2013): 112-118.

This study investigates the neuroprotective effects of madecassoside, isolated from the traditional Chinese medicine Centella Asiatica, on an early Parkinson's disease rat model induced by MPTP.
During the 7-day oral administration of madecassoside to rats, MPTP was injected on day 7. Over the following 14 days, madecassoside was administered through injection. On day 14, behavioral tests were conducted 1 hour after the administration. The rats were then sacrificed, and the substantia nigra and striatum were dissected. Levels of dopamine (DA), malondialdehyde (MDA), glutathione (GSH), the gene expression of Bcl-2/Bax, and the protein level of brain-derived neurotrophic factor (BDNF) were measured. The results showed that madecassoside treatment improved motor dysfunction and protected dopaminergic neurons by antagonizing MPTP-induced neurotoxicity. madecassoside significantly alleviated the reduction of dopamine in the striatum caused by MPTP. The MDA content in the madecassoside-treated group was significantly reduced, while GSH levels, the Bcl-2/Bax ratio, and BDNF protein expression were significantly increased. These findings suggest that madecassoside can effectively restore the early symptoms of Parkinson's disease induced by MPTP through its neuroprotective effects, including the reversal of DA depletion, antioxidant activity, increased Bcl-2/Bax ratio, and enhanced BDNF protein expression.

Custom Q&A

What is the CAS number of Madecassoside?

The CAS number of Madecassoside is 34540-22-2.

What is the molecular weight of Madecassoside?

The molecular weight of Madecassoside is 975.13.

What is the molecular formula of Madecassoside?

The molecular formula of Madecassoside is C48H78O20.

What is the IUPAC Name of Madecassoside?

The IUPAC Name of Madecassoside is [6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] 8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate.

What are some synonyms for Madecassoside?

Some synonyms for Madecassoside include O-6-Deoxy-alpha-L-mannopyranosyl, beta-D-glucopyranosyl, and 2alpha,3beta,4alpha,6beta.

What is the appearance of Madecassoside?

Madecassoside appears as a white-beige powder.

What is the typical application of Madecassoside?

Madecassoside can be used as an antioxidant and as an anti-inflammatory agent.

What is the purity of Madecassoside?

The purity of Madecassoside is 98%.

What is the physical state of Madecassoside?

Madecassoside is in a solid physical state.

What is the percentage of actives in Madecassoside?

Madecassoside contains 95% actives.

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