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A2612

Sigma-Aldrich

Asiatic acid

≥98% (HPLC), from Centella asiatica

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Synonym(s):
2α,23-Dihydroxyursolic acid, Dammarolic acid, NSC 166063
Empirical Formula (Hill Notation):
C30H48O5
CAS Number:
464-92-6
Molecular Weight:
488.70
EC Number:
482-720-9
MDL number:
MFCD00238541
PubChem Substance ID:
329770790
NACRES:
NA.25

biological source

Centella asiatica

Quality Level

200

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white

mp

325-330 °C (lit.)

solubility

methanol: 1 mg/mL, clear, colorless

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

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]5CC[C@@]34C)[C@@H]2[C@H]1C)C(O)=O

InChI

1S/C30H48O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,17-18,20-24,31-33H,8-16H2,1-6H3,(H,34,35)/t17-,18+,20-,21-,22-,23+,24+,26+,27+,28-,29-,30+/m1/s1

InChI key

JXSVIVRDWWRQRT-UYDOISQJSA-N

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General description

Asiatic acid is a naturally occurring pentacyclic triterpenoid, obtained from Centella asiatica.

Application

Asiatic acid has been used in the in vitro study of its cytotoxic potential in glioblastoma cells. It has also been used for the in vivo quantitative analysis of asiatic acid in Centella asiatica L. and in vitro study of enhancement of asiatic acid yield upon using organic elicitors.
Starting material for asiatic acid derivative synthesis for use as:
  • Anticancer agents
  • Glycogen phosphorylase inhibitors
  • Hepatoprotectants

Biochem/physiol Actions

Asiatic acid has been reported to exhibit a pernicious effect on glioblastoma, breast, liver, melanoma, and colon cancers and anti-angiogenic activity. Additionally, it can cross the blood-brain barrier and cause apoptosis in human malignant glioma and hepatoma cells. Asiatic acid also effectively inhibits the Ultraviolet A modulated signal transduction pathways and thereby can be used against UVA-induced photoaging of the skin. It has been noted to show antinociceptive and anti-inflammatory properties plus inhibitory effect on neurotoxicity induced by β-amyloid and glutamate.
Asiatic acid is commonly used in wound healing. Asiatic acid has antioxidant, anti-inflammatory and neuroprotective properties.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Yong Soo Lee et al.
European journal of pharmacology, 476(3), 173-178 (2003-09-13)
Premature aging of the skin (photoaging) is a well-documented consequence of exposure to ultraviolet-A (UVA). Enhanced generation of reactive oxygen species and induction of matrix metalloproteinases (MMPs) appear to be the most important components of UVA-modulated signal transduction pathways, ultimately
Flourina Kumar Thakor et al.
Molecular and cellular biochemistry, 430(1-2), 179-190 (2017-02-17)
Glioblastoma multiforme is the most common and malignant primary brain tumor in adults. Despite current treatment options including surgery followed by radiation and chemotherapy with temozolomide and cisplatin, the median survival rate remains low (<16 months). Combined with increasing drug
Quantification of asiatic acid from plant parts of Centella asiatica L. and enhancement of its synthesis through organic elicitors in in vitro
Mohammadparast B, et al.,
Horticulture, Environment, and Biotechnology, 55(6), 578-582 (2014)
Byung Chul Park et al.
Cancer letters, 218(1), 81-90 (2005-01-11)
Asiatic acid (AA) is a pentacyclic triterpene found in Centella asiatica. In the present study, the mechanism of anticancer effect of AA on skin cancer was investigated. AA decreased viability and induced apoptosis in human melanoma SK-MEL-2 cells in a
S Momtaz et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 51, 38-45 (2012-09-20)
The possible biochemical activities of the acetonic/ethanolic extract of the leaves of Maytenus procumbens (L.M.P), and its isolated compounds were investigated in the present study. In cytotoxicity assay, L.M.P showed IC(50) of 68.79, 51.22, 78.49, 76.59, and 76.64μg/ml on Caco-2
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