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MedKoo Cat#: 575050 | Name: Madecassoside
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Madecassoside is a triterpenoid compound that has anti-inflammatory, wound healing, and anti-oxidant activities. It has been reported to suppress LPS-induced TNF-alpha production via inhibition of ERK, p38, and NF-kappaB activity.

Chemical Structure

Madecassoside
Madecassoside
CAS#34540-22-2

Theoretical Analysis

MedKoo Cat#: 575050

Name: Madecassoside

CAS#: 34540-22-2

Chemical Formula: C48H78O20

Exact Mass: 974.5086

Molecular Weight: 975.13

Elemental Analysis: C, 59.12; H, 8.06; O, 32.81

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
100mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Asiaticoside A; Madecassoside; Redermic
IUPAC/Chemical Name
(2S,3R,4S,5S,6R)-6-((((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl (1S,2R,4aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,12bR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
InChi Key
BNMGUJRJUUDLHW-ODCOUYPHSA-N
InChi Code
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/t19-,20+,21+,23-,24-,25-,26-,27-,28+,29-,30-,31+,32+,33-,34+,35-,36-,37-,38-,39+,40-,41-,42+,44-,45+,46-,47-,48+/m1/s1
SMILES Code
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5[C@H](O)C[C@@]34C)[C@@H]2[C@H]1C)C(=O)O[C@@H]6O[C@H](CO[C@@H]7O[C@H](CO)[C@@H](O[C@H]8O[C@@H](C)[C@@H](O)[C@H](O)[C@@H]8O)[C@H](O)[C@H]7O)[C@@H](O)[C@H](O)[C@H]6O
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Madecassoside is a pentacyclic triterpene isolated from Centella asitica (L.), as an anti-inflammatory, anti-oxidative activities and anti-aging agent.
In vitro activity:
This study aimed to investigate the effect of madecassoside against oxidative stress-induced injury of endothelial cells. Hydrogen peroxide (H(2)O(2), 500 µmol/L) was employed as an inducer of oxidative stress in human umbilical vein endothelial cells (HUVECs). As a result, madecassoside (10, 30, 100 µmol/L) could reverse morphological changes, elevate cell viability, increase glutathione levels, and decrease lactate dehydrogenase and malondialdehyde levels caused by H(2)O(2) in a concentration-dependent manner. These data suggested that madecassoside could protect HUVECs from oxidative injury, which was probably achieved by inhibiting cell apoptosis via protection of mitochondria membranes and downregulation of the activation of caspase-3 and p38 MAPK. Reference: J Biochem Mol Toxicol. 2012 Oct;26(10):399-406. https://pubmed.ncbi.nlm.nih.gov/22829481/
In vivo activity:
A PF model was established in mice by intratracheal instillation of bleomycin. Administration of madecassoside, p.o., but not its main metabolite madecassic acid, exhibited a direct anti-PF effect in mice. Madecassoside increased the expression of hepatocyte growth factor (HGF) in colon tissues, and HGF receptor antagonists attenuated its anti-PF effect. Madecassoside facilitated the secretion of HGF from colonic epithelial cells by activating the PPAR-γ pathway, as shown by an up-regulation of PPAR-γ mRNA expression, nuclear translocation and DNA-binding activity both in vitro and in vivo. Reference: Br J Pharmacol. 2016 Apr;173(7):1219-35. doi https://pubmed.ncbi.nlm.nih.gov/26750154/
Solvent mg/mL mM
Solubility
DMF 25.0 25.64
DMSO 70.0 71.79
Ethanol 52.5 53.84
PBS (pH 7.2) 10.0 10.26
Water 66.7 68.37
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 975.13 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Watanabe S, Hibiya S, Katsukura N, Kitagawa S, Sato A, Okamoto R, Watanabe M, Tsuchiya K. Importance of Telomere Shortening in the Pathogenesis of Ulcerative Colitis: A New Treatment From the Aspect of Telomeres in Intestinal Epithelial Cells. J Crohns Colitis. 2022 Jan 28;16(1):109-121. doi: 10.1093/ecco-jcc/jjab115. PMID: 34180971. 2. Bian D, Liu M, Li Y, Xia Y, Gong Z, Dai Y. Madecassoside, a triterpenoid saponin isolated from Centella asiatica herbs, protects endothelial cells against oxidative stress. J Biochem Mol Toxicol. 2012 Oct;26(10):399-406. doi: 10.1002/jbt.21434. Epub 2012 Jul 24. PMID: 22829481. 3. Xia Y, Xia YF, Lv Q, Yue MF, Qiao SM, Yang Y, Wei ZF, Dai Y. 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. doi: 10.1111/bph.13421. Epub 2016 Feb 25. PMID: 26750154; PMCID: PMC5341335. 4. Sun B, Hayashi M, Kudo M, Wu L, Qin L, Gao M, Liu T. Madecassoside Inhibits Body Weight Gain via Modulating SIRT1-AMPK Signaling Pathway and Activating Genes Related to Thermogenesis. Front Endocrinol (Lausanne). 2021 Mar 9;12:627950. doi: 10.3389/fendo.2021.627950. PMID: 33767670; PMCID: PMC7985537.
In vitro protocol:
1. Watanabe S, Hibiya S, Katsukura N, Kitagawa S, Sato A, Okamoto R, Watanabe M, Tsuchiya K. Importance of Telomere Shortening in the Pathogenesis of Ulcerative Colitis: A New Treatment From the Aspect of Telomeres in Intestinal Epithelial Cells. J Crohns Colitis. 2022 Jan 28;16(1):109-121. doi: 10.1093/ecco-jcc/jjab115. PMID: 34180971. 2. Bian D, Liu M, Li Y, Xia Y, Gong Z, Dai Y. Madecassoside, a triterpenoid saponin isolated from Centella asiatica herbs, protects endothelial cells against oxidative stress. J Biochem Mol Toxicol. 2012 Oct;26(10):399-406. doi: 10.1002/jbt.21434. Epub 2012 Jul 24. PMID: 22829481.
In vivo protocol:
1. Xia Y, Xia YF, Lv Q, Yue MF, Qiao SM, Yang Y, Wei ZF, Dai Y. 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. doi: 10.1111/bph.13421. Epub 2016 Feb 25. PMID: 26750154; PMCID: PMC5341335. 2. Sun B, Hayashi M, Kudo M, Wu L, Qin L, Gao M, Liu T. Madecassoside Inhibits Body Weight Gain via Modulating SIRT1-AMPK Signaling Pathway and Activating Genes Related to Thermogenesis. Front Endocrinol (Lausanne). 2021 Mar 9;12:627950. doi: 10.3389/fendo.2021.627950. PMID: 33767670; PMCID: PMC7985537.
1. Sasmita AO, Ling APK, Voon KGL, Koh RY, Wong YP. Madecassoside activates anti‑neuroinflammatory mechanisms by inhibiting lipopolysaccharide‑induced microglial inflammation. Int J Mol Med. 2018 May;41(5):3033-3040. doi: 10.3892/ijmm.2018.3479. Epub 2018 Feb 9. PMID: 29436598. 2. Dou Y, Luo J, Yu J, Xia Y, Dai Y. Cholinergic system is involved in the therapeutic effect of madecassoside on collagen-induced arthritis in rats. Int Immunopharmacol. 2019 Oct;75:105813. doi: 10.1016/j.intimp.2019.105813. Epub 2019 Aug 9. PMID: 31404889. 3. Xu X, Wang Y, Wei Z, Wei W, Zhao P, Tong B, Xia Y, Dai Y. Madecassic acid, the contributor to the anti-colitis effect of madecassoside, enhances the shift of Th17 toward Treg cells via the PPARγ/AMPK/ACC1 pathway. Cell Death Dis. 2017 Mar 30;8(3):e2723. doi: 10.1038/cddis.2017.150. PMID: 28358365; PMCID: PMC5386545.