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A2612

Sigma-Aldrich

Asiatic acid

≥98% (HPLC), from Centella asiatica

Synonyme(s) :

2α,23-Dihydroxyursolic acid, Dammarolic acid, NSC 166063

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About This Item

Formule empirique (notation de Hill):
C30H48O5
Numéro CAS:
Poids moléculaire :
488.70
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352212
ID de substance PubChem :
Nomenclature NACRES :
NA.25

Source biologique

Centella asiatica

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

protect from light

Couleur

white

Pf

325-330 °C (lit.)

Solubilité

methanol: 1 mg/mL, clear, colorless

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

JXSVIVRDWWRQRT-UYDOISQJSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

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
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)
Sreenath Nandakumar Nair et al.
Rapid communications in mass spectrometry : RCM, 26(17), 1899-1908 (2012-08-01)
Asiatic acid (AA), a pentacyclic triterpene from Centella asiatica (L.) Urban, has shown numerous therapeutic activities. However, none of the published works to date has used high-performance liquid chromatography/tandem mass spectrometry (HPLC/MS/MS) for determination of AA from biological fluids. Therefore
Shyh-Shyun Huang et al.
Evidence-based complementary and alternative medicine : eCAM, 2011, 895857-895857 (2011-05-18)
Asiatic acid (AA), a pentacyclic triterpene compound in the medicinal plant Centella asiatica, was evaluated for antinociceptive and anti-inflammatory effects. Treatment of male ICR mice with AA significantly inhibited the numbers of acetic acid-induced writhing responses and the formalin-induced pain
Vinayagam Ramachandran et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 20(3-4), 230-236 (2012-10-30)
Asiatic acid (AA), a triterpenoid derivative of Centella asiatica, has shown significant biological effects of antioxidant and anti-inflammatory activities. Aim of this investigation was to evaluate the antihyperglycemic effect of AA on the activities of hepatic enzymes of carbohydrate metabolism

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