Asiaticoside

Asiaticoside is a skin whiening agent found in Cetella. It decreases DNA binding by MITF. It also induces apoptosis in breast cancer cells, improves memory and learning deficits, decreases release of pro-inflammatory cytokines, and suppresses LPS-induced inflammation and fever.

Product information

CAS Number: 16830-15-2

Molecular Weight: 959.12

Formula: C48H78O19

Synonym:

Ba 2742

CCRIS8995

NSC166062

BRN-0078195

Emdecassol

Madecassol

Chemical Name: (2S,3R,4S,5S,6R)-6-((((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2S,3R,4R,5R,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,8aR,9R,10R,11R,12aR,12bR,14bS)-10,11-dihydroxy-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

Smiles: C[C@@]12CC[C@]3(CC[C@@H](C)[C@H](C)[C@H]3C1=CC[C@H]1[C@@]2(C)CC[C@H]2[C@](C)(CO)[C@@H](O)[C@H](O)C[C@@]21C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChiKey: WYQVAPGDARQUBT-FGWHUCSPSA-N

InChi: InChI=1S/C48H78O19/c1-20-10-13-48(15-14-46(6)23(29(48)21(20)2)8-9-28-44(4)16-24(51)39(60)45(5,19-50)27(44)11-12-47(28,46)7)43(61)67-42-36(58)33(55)31(53)26(65-42)18-62-40-37(59)34(56)38(25(17-49)64-40)66-41-35(57)32(54)30(52)22(3)63-41/h8,20-22,24-42,49-60H,9-19H2,1-7H3/t20-,21+,22+,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

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

Asiaticoside (0, 100, 250, and 500 mg/L) dose-dependently inhibits keloid fibroblasts proliferation. Asiaticoside (100, 250, and 500 mg/L) decreases the expression of collagen protein and mRNA, reduces the expression of TGF-bRI, TGF-bRII protein, and mRNA, increases the expression of Smad7, but does not affect Smad2, Smad3, Smad4, phosphorylated Smad2, and phosphorylated Smad3 in keloid fibroblasts. Asiaticoside (12.5 and 50, and 25 and 50 µg/mL) prevents endothelial cells from hypoxia-induced inhibition of cell viability and NO production. Asiaticoside (50 µg/mL) also protects endothelial cells from hypoxia-induced apoptosis and upregulates and phosphorylation of AKT/eNOS in hypoxia-exposed HPAECs.

In Vivo:

Asiaticoside (50 mg/kg daily) blocks the development of hypoxic pulmonary hypertension (PH), cardiovascular remodeling and endothelial cell injury in rats with pulmonary hypertension. Asiaticoside (5, 15 or 45 mg/kg, p.o.) improves the learning and memory deficit, protects hippocampi against the impairment, decreases Aβ deposits in the hippocampus, and ameliorates impaired subcellular structure in rats treated with Aβ oligomers.

References:

1. Sun T, Liu B, Li P. Nerve Protective Effect of Asiaticoside against Ischemia-Hypoxia in Cultured Rat Cortex Neurons. Med Sci Monit. 2015 Oct 8;21:3036-41. doi: 10.12659/MSM.894024. PubMed PMID: 26447863; PubMed Central PMCID: PMC4603616.
2. Fong LY, Ng CT, Zakaria ZA, Baharuldin MT, Arifah AK, Hakim MN, Zuraini A. Asiaticoside Inhibits TNF-α-Induced Endothelial Hyperpermeability of Human Aortic Endothelial Cells. Phytother Res. 2015 Oct;29(10):1501-8. doi: 10.1002/ptr.5404. Epub 2015 Jul 14. PubMed PMID: 26171791.
3. Qi FY, Yang L, Tian Z, Zhao MG, Liu SB, An JZ. Neuroprotective effects of Asiaticoside. Neural Regen Res. 2014 Jul 1;9(13):1275-82. doi: 10.4103/1673-5374.137574. PubMed PMID: 25221579; PubMed Central PMCID: PMC4160853.
4. Al-Saeedi FJ. Study of the cytotoxicity of asiaticoside on rats and tumour cells. BMC Cancer. 2014 Mar 25;14:220. doi: 10.1186/1471-2407-14-220. PubMed PMID: 24667059; PubMed Central PMCID: PMC3986932.

Products are for research use only. Not for human use.