11-Deoxyalisol B

CAS# 155073-73-7

11-Deoxyalisol B

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Quality Control of 11-Deoxyalisol B

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Chemical structure

11-Deoxyalisol B

3D structure

Chemical Properties of 11-Deoxyalisol B

Cas No. 155073-73-7 SDF Download SDF
PubChem ID 101661274 Appearance Powder
Formula C30H48O3 M.Wt 456.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (5R,8S,9S,10R,14R)-17-[(2R,4S)-4-[(2R)-3,3-dimethyloxiran-2-yl]-4-hydroxybutan-2-yl]-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-3-one
SMILES CC(CC(C1C(O1)(C)C)O)C2=C3CCC4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)C)C
Standard InChIKey FRARORPBMYOKKW-DNRQRXMOSA-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 11-Deoxyalisol B

The tubers of Alisma plantago-aquatica Linn.

Protocol of 11-Deoxyalisol B

Structure Identification
Chinese Journal of Pharmaceutical Analysis, 2015,35(2):210-217.

Determination of triterpenoids in Rhizoma Alismatis extracts.[Reference: WebLink]

To establish ultraviolet-visible(UV-Vis)spectrophotometry and HPLC method for determination of triterpenoids in Rhizoma Alismatis extracts.
METHODS AND RESULTS:
With 5% vanillin-acetic acid and perchloric acid as the developer, the colorimetric method was applied.Total triterpenoids in extracts was determined at 555 nm wavelength by UV-Vis spectrophotometry, and 12 triterpenoids was determined by HPLC with Ultimate XB-C18 column(4.6 mm×150 mm, 5 μm)and the mobile phase consisting of acetonitrile-water(5% methanol)at a flow rate of 1.0 mL · min-1.The detection wavelength was set at 208 nm. With 23-acetate alisol B as the standard, the UV-Vis spectrophotometry method was applied.There was a good linear relationship between the concentration and absorbance of 23-acetate alisol B in the range of 5.9-15.6 μg · mL-1 (r=0.999 1);the average recovery rate was 99.05% and the RSD was 2.3%.By HPLC, the linear range of 12 detected compounds were fine(r>0.999 0), the overall recoveries ranged from 95.89%-99.33%, with the RSD ranging from 2.0%-3.4%.The contents of 12 triterpenoids including alisol A, alisol B, alisol C, alisol G, alisol L, 23-acetate-alisol A, 23-acetate-alisol B, 23-a cetate-alisol C, 16-oxo-23-acetate-alisol A, 16-oxo-24-acetate-alisol A, 11-Deoxyalisol B, 24-a cetate-alisol A were 5.71%-5.95%, 3.47%-3.99%, 2.53%- 2.97%, 3.07%-3.93%, 3.65%-3.99%, 2.39%-3.02%, 10.56%-11.32%, 9.44%-9.86%, 0.63% -3.14%, 1.08%-1.21%, 2.29%-2.85% and 4.04%-5.02%, respectively.
CONCLUSIONS:
The two methods are in accordance with the requirements of the methodology validation, indicating that the ultraviolet-visible(UV-Vis)spectrophotometry method can be used for the detection of the total triterpenoids and the HPLC method can be used for detection of 12 triterpenoids.

11-Deoxyalisol B Dilution Calculator

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11-Deoxyalisol B Molarity Calculator

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Preparing Stock Solutions of 11-Deoxyalisol B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1896 mL 10.9481 mL 21.8962 mL 43.7924 mL 54.7405 mL
5 mM 0.4379 mL 2.1896 mL 4.3792 mL 8.7585 mL 10.9481 mL
10 mM 0.219 mL 1.0948 mL 2.1896 mL 4.3792 mL 5.4741 mL
50 mM 0.0438 mL 0.219 mL 0.4379 mL 0.8758 mL 1.0948 mL
100 mM 0.0219 mL 0.1095 mL 0.219 mL 0.4379 mL 0.5474 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 11-Deoxyalisol B

[Studies on triterpenes chemical constituents in rhizome of Alisma gramineum].[Pubmed:16245905]

Zhongguo Zhong Yao Za Zhi. 2005 Aug;30(16):1263-5.

OBJECTIVE: To investigate the triterpenoids chemical constituents in rhizome of Alisma gramineum. METHOD: Silicon gel chromatography and HPLC techniques were employed for isolation and purification of the constituents, and the structures were elucidated by various spectral analyses such as NMR, MS and IR. RESULT: 5 protostane-type tetracyclic triterpenoids were isolated and identified as 16,23-oxidoalisol B(1), 11-deoxyalisol C(2), alisol F(3), 16beta-methoxyalisol B acetate (4), 16beta-hydroxyalisol B acetate (5). CONCLUSION: All of these compounds were found from A. gramineum for the first time.

Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale.[Pubmed:27615692]

Phytochemistry. 2016 Nov;131:150-157.

Sixteen triterpenoids and nine sesquiterpenoids were isolated from the rhizome of Alisma orientale. Structures of 16-oxo-11-anhydroalisol A 24-acetate, 13beta,17beta-epoxy-24,25,26,27-tetranor-alisol A 23-oic acid, 1alphaH,5alphaH-guaia-6-ene-4beta,10beta-diol, and alisguaiaone were elucidated by comprehensive spectroscopic data analysis. The cytotoxic, antibacterial, antifungal, anti-inflammatory, and alpha-glucosidase inhibitory activities of isolated terpenoids were evaluated. Triterpenoids alisol A, alisol A 24-acetate, 25-O-ethylalisol A, 11-deoxyalisol A, alisol E 24-acetate, alisol G, alisol B 23-acetate and sesquiterpenoids 1alphaH,5alphaH-guaia-6-ene-4beta,10beta-diol, 10-hydroxy-7,10-epoxysalvialane exhibited cytotoxicities against the three tested human cancer cell lines with IC50 values ranging from 11.5 +/- 1.7 muM to 76.7 +/- 1.4 muM. Triterpenoids alisol A, 25-O-ethylalisol A, 11-deoxyalisol A, alisol E 24-acetate, alisol G, and 25-anhydroalisol F showed antibacterial activities against the Gram-positive strains Bacillus subtilis and Staphylococcus aureus with MIC values of 12.5-100 mug/mL. Sesquiterpenoid 4beta,10beta-dihydroxy-1alphaH,5betaH-guaia-6-ene exhibited antibacterial activity against B. subtilis with an MIC value of 50 mug/mL, and 10-hydroxy-7,10-epoxysalvialane exhibited activity against S. aureus with an MIC value of 100 mug/mL. Compounds 16-oxo-11-anhydroalisol A 24-acetate, alisol F, 25-anhydroalisol F, and alisguaiaone exhibited inhibitory effects on lipopolysaccharide-induced NO production in RAW 264.7 macrophage cells. None of the compounds showed obvious inhibitory activity against alpha-glucosidase.

A new triterpenoid from Alisma orientale and their antibacterial effect.[Pubmed:23212633]

Arch Pharm Res. 2012 Nov;35(11):1919-26.

A new triterpenoid, named alisol Q 23-acetate, as well as fourteen known terpenes, alisol B 23-acetate (2), alisol B (3), alismol (4), 10-O-methyl-alismoxide (5), alismoxide (6), 11-deoxyalisol C (7), 13beta,17beta-epoxyalisol B 23-acetate (8), 4beta,12-dihydroxyguaian-6,10-diene (9), alisol C 23-acetate (10), alisolide (11), 16beta-methoxyalisol B monoacetate (12), alisol A (13), 16beta-hydroxyalisol B 23-acetate (14), alisol A 24-acetate (15) were isolated from the rhizomes of Alisma orientale. The structures of compounds (1-15) were identified based on 1D and 2D NMR, including (1)H-(1)H COSY, HSQC, HMBC and NOESY spectroscopic analyses. Among these isolates, antibacterial effect of compounds 2, 3, 10, and 15, major constituents of A. orientale was examined. The MIC values of compounds 2, 10, and 15 were 5-10 betag/mL against eight antibiotic resistant strains, which were lower than those from the positive controls (MICs of chloramphenicol and ampicillin were 5-80 mug/mL). Therefore, compounds 2, 10 and 15 exhibited the potent antibacterial activity.

Effects of sesquiterpenes and triterpenes from the rhizome of Alisma orientale on nitric oxide production in lipopolysaccharide-activated macrophages: absolute stereostructures of alismaketones-B 23-acetate and -C 23-acetate.[Pubmed:10560729]

Bioorg Med Chem Lett. 1999 Nov 1;9(21):3081-6.

The methanolic extract from a Chinese herbal medicine, the rhizome of Alisma orientale, was found to exhibit inhibitory activity of nitric oxide (NO) production in lipopolysaccharide (LPS)activated macrophages. Novel triterpenes, alismaketones-B 23-acetate and -C 23-acetate, were isolated from the active extract together with eight sesquiterpenes and eighteen protostane-type triterpenes. The absolute stereostructures of new triterpenes were characterized on the basis of chemical and physicochemical evidence, which included the chemical correlations with known triterpenes. The guaiane-type sesquiterpenes (alismol, orientalols A and C) and protostane- and seco-protostane-types triterpenes (alisols C monoacetate, E-23-acetate, F, H, I, L-23-acetate, and M-23-acetate, alismaketones-B 23-acetate and -C 23-acetate, alismalactone 23-acetate, and 3-methylalismalactone 23-acetate) inhibited LPS-induced NO production (IC50 = 8.4-68 microM). Other triterpenes (alisols A, A monoacetate, B, B monoacetate, E, G, K-23-acetate, and N-23-acetate and 11-Deoxyalisol B) also showed the potent inhibitory activity, but they showed cytotoxic effects more than 30 microM (MTT assay). In addition, alismol and alisol F were found to suppress iNOS induction.

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