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M6949

Sigma-Aldrich

Madecassoside from Centella asiatica

≥95% (HPLC)

Synonym(s):

Madecassoside, Asiaticoside A, Redermic

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About This Item

Empirical Formula (Hill Notation):
C48H78O20
CAS Number:
34540-22-2
Molecular Weight:
975.12
EC Number:
252-076-1
UNSPSC Code:
12352212
NACRES:
NA.25

assay

≥95% (HPLC)

form

powder

color

white to off-white

solubility

H2O: 1 mg/mL, clear, colorless

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

O1C(C(C(C(C1C)O)O)O)OC2C(OC(C(C2O)O)OCC3OC(C(C(C3O)O)O)OC(=O)C54C(C(C(CC5)C)C)C6=CCC7C8(C(C(CC7(C6(CC4)C)C)O)C(C(C(C8)O)O)(CO)C)C)CO

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

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General description

Madecassoside is one of the major pentacyclic triterpenoid saponin compounds extracted from Centella asiatica.

Application

Madecassoside has been used to study its cytotoxic effects on mouse macrophage cell lines (J774A.1). It has also been used as a potential inhibitor of serine racemase (SR) for in vitro and ex vivo studies.

Biochem/physiol Actions

Madecassoside has a wide range of reported biological activities including, anti-inflammatory, wound healing, and antioxidant activities. It has been reported to suppress LPS-induced TNF-alpha production via inhibition of ERK, p38, and NF-kappaB activity.
Madecassoside has skin hydration properties. It is a well-known collagen inducer that exerts anti-aging and anti-rheumatoid arthritis effects. Madecassoside also elicits neuroprotective activities.
Madecassoside is a triterpenoid compound found in Centella asiatica (Gotu kola), a medicinal herb used in traditional Chinese medicine (TCM), Ayurvedic medicine, and traditional African medicine. Madecassoside has a wide range of reported biological activities including, 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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SLCK6925
SLCH8529
SLCB2376
SLBW2469
SLBV7802

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Jie Song et al.
Burns : journal of the International Society for Burn Injuries, 38(5), 677-684 (2012-03-01)
Keloid is a specific skin scar that expands beyond the boundaries of the original injury as it heals. The invasive nature of keloid and notable migratory activity of fibroblasts are a hallmark, which distinguishes keloids from other common scars. Madecassoside
Feng-Lun Zhang et al.
Biomedical chromatography : BMC, 22(2), 119-124 (2007-08-19)
A high-performance liquid chromatography method with evaporative light scattering detection was established for simultaneous determination of three major triterpenoid glycosides, i.e. asiaticoside, madecassoside and asiaticoside-B, in Centella asiatica extracts. The optimal chromatographic conditions were achieved on a COSMOSIL 5C(18)-MS-II column
Wen-Jing Han et al.
Biomedical chromatography : BMC, 26(1), 26-32 (2011-03-18)
A rapid, sensitive and specific high-performance liquid chromatography/electrospray ionization mass spectrometric (LC-ESI-MS) method was developed and validated for the quantification of madecassoside, a major active constituent of Centella asiatica (L.) Urb. herbs, in rat plasma. With paeoniflorin as an internal
Mercè Bonfill et al.
Biomedical chromatography : BMC, 20(2), 151-153 (2005-10-06)
The identification of the four principal triterpenoid components of Centella asiatica has been achieved by TLC on silica gel plates and mass spectrometry, as a modification of the method described in the European Pharmacopoeia (5th edn). A combination of ethyl
Mingzhe Gao et al.
Se pu = Chinese journal of chromatography, 26(3), 362-365 (2008-08-30)
A high performance liquid chromatographic (HPLC) method was successfully used to separate asiaticoside and madecassoside from the extract of Centella asiatica (L.) Urb. The raw material containing 20% asiaticoside and 45% madecassoside was dissolved in methanol and used for the
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