Asiaticoside B

CAS# 125265-68-1

Asiaticoside B

Catalog No. BCN8709----Order now to get a substantial discount!

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Quality Control of Asiaticoside B

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Chemical structure

Asiaticoside B

3D structure

Chemical Properties of Asiaticoside B

Cas No. 125265-68-1 SDF Download SDF
PubChem ID 91618002 Appearance White powder
Formula C48H78O20 M.Wt 975.13
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Asiaticoside B
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(2~{S},3~{R},4~{S},5~{S},6~{R})-6-[[(2~{R},3~{R},4~{R},5~{S},6~{R})-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4~{a}~{S},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{R},8~{a}~{R},9~{R},10~{R},11~{R},12~{a}~{R},14~{b}~{S})-8,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6~{a},6~{b},9,12~{a}-hexamethyl-1,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydropicene-4~{a}-carboxylate
SMILES CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CC(C(C(C8C(CC7(C6(CC5)C)C)O)(C)CO)O)O)C)(C)C)O)O)O)CO)O)O)O
Standard InChIKey NNWMHSNRRWMMBI-PJISEHJASA-N
Standard InChI InChI=1S/C48H78O20/c1-20-28(53)30(55)33(58)40(64-20)67-36-25(17-49)65-39(35(60)32(36)57)63-18-26-29(54)31(56)34(59)41(66-26)68-42(62)48-12-10-43(2,3)14-22(48)21-8-9-27-44(4)15-24(52)38(61)45(5,19-50)37(44)23(51)16-47(27,7)46(21,6)11-13-48/h8,20,22-41,49-61H,9-19H2,1-7H3/t20-,22-,23+,24+,25+,26+,27+,28-,29+,30+,31-,32+,33+,34+,35+,36+,37+,38-,39+,40-,41-,44+,45-,46+,47+,48-/m0/s1
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 Asiaticoside B

1 Cimicifuga sp.

Biological Activity of Asiaticoside B

DescriptionAsiaticoside B has notable cytotoxicity against HepG2 and MCF-7 cancer cell lines.
In vitro

Cytotoxic cycloartane triterpene saponins from Actaea asiatica.[Pubmed: 17067171 ]

J Nat Prod. 2006 Oct;69(10):1500-2.


METHODS AND RESULTS:
Three new 9,19-cycloartane triterpene glycosides, asiaticoside A (1), Asiaticoside B (2), and 25-O-ethylcimigenol-3-O-beta-D-xylopyranoside (3), together with cimiacemoside I (4), 25-O-acetylcimigenol-3-beta-O-D-xyloside (5), and 25-anhydrocimigenol-beta-O-D-xyloside (6) were isolated from the roots/rhizomes extract of Actaea asiatica, and their structures were established by spectroscopic methods (IR, HRESIMS, and NMR).
CONCLUSIONS:
Compounds 1-3, 5, and 6 had notable cytotoxicity against HepG2 and MCF-7 cancer cell lines.

Protocol of Asiaticoside B

Structure Identification
Pharmazie. 2003 Jun;58(6):381-4.

An improved HPLC method for quantitative determination of six triterpenes in Centella asiatica extracts and commercial products.[Pubmed: 12856998]


METHODS AND RESULTS:
An improved HPLC qualitative and quantitative method of six triterpenes (asiaticoside, madecassoside, asiatic acid, madecassic acid, terminolic acid, and Asiaticoside B) in Centella asiatica (raw plant material and preparations) is described in this paper. After 50 minutes the six active triterpenes were separated and detected in the methanolic extract at a limit of 0.01 microg/ml.
CONCLUSIONS:
The method uses a Phenomenex Aqua 5mu C18 (200 A) column as the stationary phase, a gradient mobile phase of water (0.1% TFA), acetonitrile (0.1% TFA), and methyl tert-butyl ether (0.1% TFA), and UV detection at 206 nm. The correlation coefficients for the calibration curves and the recovery rates ranged from 0.995 to 0.999 and from 98.39% to 100.02%, respectively. The qualitative and quantitative results are discussed.

Asiaticoside B Dilution Calculator

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Asiaticoside B Molarity Calculator

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Preparing Stock Solutions of Asiaticoside B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.0255 mL 5.1275 mL 10.255 mL 20.5101 mL 25.6376 mL
5 mM 0.2051 mL 1.0255 mL 2.051 mL 4.102 mL 5.1275 mL
10 mM 0.1026 mL 0.5128 mL 1.0255 mL 2.051 mL 2.5638 mL
50 mM 0.0205 mL 0.1026 mL 0.2051 mL 0.4102 mL 0.5128 mL
100 mM 0.0103 mL 0.0513 mL 0.1026 mL 0.2051 mL 0.2564 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 Asiaticoside B

New 9, 19-cycloartane triterpenoid from the root of Cimicifuga foetida.[Pubmed:24863355]

Chin J Nat Med. 2014 Apr;12(4):294-6.

AIM: To study the 9, 19-cycloartane triterpenes from the roots of Cimicifuga foetida. METHOD: Chromatographic separations by silica gel, C18 reversed phase silica gel, and high-performance liquid chromatography (HPLC) were used. All of the structures were elucidated on the basis of spectroscopic analysis and chemical methods. RESULTS: Five 9, 19-cycloartane triterpenes, (3beta, 12beta, 15alpha, 24R)-12, 2'-diacetoxy-24, 25-epoxy-15-hydroxy-16, 23-dione-3-O-alpha-L-arabinopyranoside (1), actein (2), 23-epi-26-deoxyactein (3), Asiaticoside B (4), and 12beta-hydroxycimigenol (5) were isolated from the roots of Cimicifuga foetida. CONCLUSION: Compound 1 is a new triterpene with two acetoxy groups at C-2' and C-12.

Cytotoxic cycloartane triterpene saponins from Actaea asiatica.[Pubmed:17067171]

J Nat Prod. 2006 Oct;69(10):1500-2.

Three new 9,19-cycloartane triterpene glycosides, asiaticoside A (1), Asiaticoside B (2), and 25-O-ethylcimigenol-3-O-beta-D-xylopyranoside (3), together with cimiacemoside I (4), 25-O-acetylcimigenol-3-beta-O-D-xyloside (5), and 25-anhydrocimigenol-beta-O-D-xyloside (6) were isolated from the roots/rhizomes extract of Actaea asiatica, and their structures were established by spectroscopic methods (IR, HRESIMS, and NMR). Compounds 1-3, 5, and 6 had notable cytotoxicity against HepG2 and MCF-7 cancer cell lines.

Medicinal foodstuffs. XXVII. Saponin constituents of gotu kola (2): structures of new ursane- and oleanane-type triterpene oligoglycosides, centellasaponins B, C, and D, from Centella asiatica cultivated in Sri Lanka.[Pubmed:11605675]

Chem Pharm Bull (Tokyo). 2001 Oct;49(10):1368-71.

Ursane- and oleanane-type triterpene oligoglycosides, centellasaponins B, C, and D, were isolated from the aerial parts of Centella asiatica (L.) Urban cultivated in Sri Lanka together with madecassoside, asiaticoside, Asiaticoside B, and sceffoleoside A. The chemical structures of centellasaponins B, C, and D were determined on the basis of chemical and physicochemical evidence to be madecassic acid 28-O-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside, madasiatic acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyra noside, and 3beta,6beta,23-trihydroxyolean-12-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyra noside, respectively.

Description

Asiaticoside B is a triterpene glycoside isolated from Actaea asiatica, with anti-cancer activity.

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