Madecassoside | CAS# 34540-22-2 | Biochemical

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

MedKoo CAT#: 575050

CAS#: 34540-22-2

Description: 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

CAS# 34540-22-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 575050
Name: Madecassoside
CAS#: 34540-22-2
Chemical Formula: C48H78O20
Exact Mass: 974.51
Molecular Weight: 975.132
Elemental Analysis: C, 59.12; H, 8.06; O, 32.81

Price and Availability

Size	Price	Availability
25mg	USD 350	2 Weeks
100mg	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. 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

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.

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.

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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.

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