Alisol B acetate

CAS# 19865-76-0

Alisol B acetate

Catalog No. BCN2304----Order now to get a substantial discount!

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Chemical structure

Alisol B acetate

3D structure

Chemical Properties of Alisol B acetate

Cas No. 19865-76-0 SDF Download SDF
PubChem ID 14036811 Appearance Cryst.
Formula C32H50O5 M.Wt 514.74
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1S,3R)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(5R,8S,9S,10S,11S,14R)-11-hydroxy-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]butyl] acetate
SMILES CC(CC(C1C(O1)(C)C)OC(=O)C)C2=C3CC(C4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)C)C)O
Standard InChIKey NLOAQXKIIGTTRE-JSWHPQHOSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Alisol B acetate

The tubers of Alisma plantago-aquatica Linn.

Biological Activity of Alisol B acetate

DescriptionAlisol B acetate can induce Bax nuclear translocation and apoptosis in human hormone-resistant prostate cancer PC-3 cells, the Bax activation and translocation from the cytosol to nucleus might be a crucial response to the apoptotic effect. Alisol B acetate exhibits an antiproliferative effect in SGC7901 cells by inducing apoptosis, apoptosis of SGC7901 cells involves mitochondria-caspase and PI3K/Akt dependent pathways.
TargetsBcl-2/Bax | PI3K | Akt | Caspase
In vitro

Alisol B acetate, a triterpene from Alismatis rhizoma, induces Bax nuclear translocation and apoptosis in human hormone-resistant prostate cancer PC-3 cells.[Pubmed: 16399228 ]

Cancer Lett., 2006, 231(2):270-8.

The anti-tumor potential of components from Chinese herbal medicines has been greatly concerned. Alisol B acetate, a triterpene from Alismatis rhizoma, induced apoptotic cell death in human hormone-resistant prostate cancer PC-3 cells in a time- and concentration-dependent manner.
METHODS AND RESULTS:
A good correlation between loss of mitochondrial membrane potential and apoptotic cell death was apparent indicating the participation of mitochondria-related mechanism. Alisol B acetate induced Bax up-regulation and nuclear translocation; it also induced the activation of initiator caspase-8 and caspase-9, and executor caspase-3, suggesting the involvement of both extrinsic and intrinsic apoptosis pathways.
CONCLUSIONS:
Taken together, it is suggested that Alisol B acetate induces apoptosis in PC-3 cells via a mitochondria-mediated mechanism with activation of caspase-8, -9 and -3. Furthermore, the Bax activation and translocation from the cytosol to nucleus might be a crucial response to the apoptotic effect.

Protocol of Alisol B acetate

Kinase Assay

Alisol B acetate induces apoptosis of SGC7901 cells via mitochondrial and phosphatidylinositol 3-kinases/Akt signaling pathways.[Reference: WebLink]

World Journal of Gastroenterology, 2009, 15(23):2870-7.

To examine the effect of Alisol B acetate on the growth of human gastric cancer cell line SGC7901 and its possible mechanism of action.
METHODS AND RESULTS:
The cytotoxic effect of Alisol B acetate on SGC7901 cells was measured by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Phase-contrast and electron microscopy were used to observe the morphological changes. Cell cycle and mitochondrial transmembrane potential (Δψm) were determined by flow cytometry. Western blotting was used to detect the expression of apoptosis-regulated gene Bcl-2, Bax, Apaf-1, caspase-3, caspase-9, Akt, P-Akt and phosphatidylinositol 3-kinases (PI3K). Alisol B acetate inhibited the proliferation of SGC7901 cell line in a time- and dose-dependent manner. PI staining showed that Alisol B acetate can change the cell cycle distribution of SGC7901, increase the proportion of cells in G0-G1 phase and decrease the proportion of S phase cells and G2-M phase cells. Alisol B acetate at a concentration of 30 μmol/L induced apoptosis after 24, 48 and 72 h incubation, with occurrence rates of apoptotic cells of 4.36%, 14.42% and 21.16%, respectively. Phase-contrast and electron microscopy revealed that the nuclear fragmentation and chromosomal condensed, cells shrank and attachment loss appeared in the SGC7901 treated with Alisol B acetate. Apoptosis of SGC7901 cells was associated with cell cycle arrest, caspase-3 and caspase-9 activation, loss of mitochondrial membrane potential and up-regulation of the ratio of Bax/Bcl-2 and inhibition of the PI3K/Akt.
CONCLUSIONS:
Alisol B acetate exhibits an anti-proliferative effect in SGC7901 cells by inducing apoptosis. Apoptosis of SGC7901 cells involves mitochondria-caspase and PI3K/Akt dependent pathways.

Structure Identification
J Liq Chromatogr Relat Technol. 2013 Jan;36(4):513-524.

Optimization of Extraction Condition for Alisol B and Alisol B Acetate in Alismatis Rhizoma using Response Surface Methodology.[Pubmed: 23335845]

Alismatis Rhizoma is a perennial herb originating from the rhizomes of Alisma orientalis (Sam) Juzep and the same species which have been used to treat seborrheic dermatitis, eczema, polydipsia, and pedal edema. We aimed to determine the concentrations of the compounds alisol B and Alisol B acetate present in a sample of the herb using high-performance liquid chromatography coupled with a photodiode array detector.
METHODS AND RESULTS:
We selected methanol as the optimal solvent considering the structures of alisol B and Alisol B acetate. We estimated the proportion of alisol B and Alisol B acetate in a standard extract to be 0.0434% and 0.2365% in methanol, respectively. To optimize extraction, we employed response surface methodology to determine the yields of alisol B and Alisol B acetate, which mapped out a central composite design consisting of 15 experimental points. The extraction parameters were time, concentration, and sample weight.
CONCLUSIONS:
The predicted concentration of alisol B derivatives was estimated to be 0.2388% under the following conditions: 81 min of extraction time, 76% of methanol concentration, and 1.52g of sample weight.

Alisol B acetate Dilution Calculator

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Alisol B acetate Molarity Calculator

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Preparing Stock Solutions of Alisol B acetate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9427 mL 9.7136 mL 19.4273 mL 38.8546 mL 48.5682 mL
5 mM 0.3885 mL 1.9427 mL 3.8855 mL 7.7709 mL 9.7136 mL
10 mM 0.1943 mL 0.9714 mL 1.9427 mL 3.8855 mL 4.8568 mL
50 mM 0.0389 mL 0.1943 mL 0.3885 mL 0.7771 mL 0.9714 mL
100 mM 0.0194 mL 0.0971 mL 0.1943 mL 0.3885 mL 0.4857 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Alisol B acetate

Optimization of Extraction Condition for Alisol B and Alisol B Acetate in Alismatis Rhizoma using Response Surface Methodology.[Pubmed:23335845]

J Liq Chromatogr Relat Technol. 2013 Jan;36(4):513-524.

Alismatis Rhizoma is a perennial herb originating from the rhizomes of Alisma orientalis (Sam) Juzep and the same species which have been used to treat seborrheic dermatitis, eczema, polydipsia, and pedal edema. We aimed to determine the concentrations of the compounds alisol B and Alisol B acetate present in a sample of the herb using high-performance liquid chromatography coupled with a photodiode array detector. We selected methanol as the optimal solvent considering the structures of alisol B and Alisol B acetate. We estimated the proportion of alisol B and Alisol B acetate in a standard extract to be 0.0434% and 0.2365% in methanol, respectively. To optimize extraction, we employed response surface methodology to determine the yields of alisol B and Alisol B acetate, which mapped out a central composite design consisting of 15 experimental points. The extraction parameters were time, concentration, and sample weight. The predicted concentration of alisol B derivatives was estimated to be 0.2388% under the following conditions: 81 min of extraction time, 76% of methanol concentration, and 1.52g of sample weight.

Alisol B acetate, a triterpene from Alismatis rhizoma, induces Bax nuclear translocation and apoptosis in human hormone-resistant prostate cancer PC-3 cells.[Pubmed:16399228]

Cancer Lett. 2006 Jan 18;231(2):270-8.

The anti-tumor potential of components from Chinese herbal medicines has been greatly concerned. Alisol B acetate, a triterpene from Alismatis rhizoma, induced apoptotic cell death in human hormone-resistant prostate cancer PC-3 cells in a time- and concentration-dependent manner. A good correlation between loss of mitochondrial membrane potential and apoptotic cell death was apparent indicating the participation of mitochondria-related mechanism. Alisol B acetate induced Bax up-regulation and nuclear translocation; it also induced the activation of initiator caspase-8 and caspase-9, and executor caspase-3, suggesting the involvement of both extrinsic and intrinsic apoptosis pathways. Taken together, it is suggested that Alisol B acetate induces apoptosis in PC-3 cells via a mitochondria-mediated mechanism with activation of caspase-8, -9 and -3. Furthermore, the Bax activation and translocation from the cytosol to nucleus might be a crucial response to the apoptotic effect.

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