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ent-16beta,17-Isopropylidenedioxykaurane

CAS# 58493-71-3

ent-16beta,17-Isopropylidenedioxykaurane

Catalog No. BCN1408----Order now to get a substantial discount!

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ent-16beta,17-Isopropylidenedioxykaurane: 5mg Please Inquire In Stock
ent-16beta,17-Isopropylidenedioxykaurane: 10mg Please Inquire In Stock
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Quality Control of ent-16beta,17-Isopropylidenedioxykaurane

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Chemical structure

ent-16beta,17-Isopropylidenedioxykaurane

3D structure

Chemical Properties of ent-16beta,17-Isopropylidenedioxykaurane

Cas No. 58493-71-3 SDF Download SDF
PubChem ID 91885200 Appearance Powder
Formula C23H38O2 M.Wt 346.6
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC1(CCCC2(C1CCC34C2CCC(C3)C5(C4)COC(O5)(C)C)C)C
Standard InChIKey KIJYVQFJGWLPQH-NXKRBXPFSA-N
Standard InChI InChI=1S/C23H38O2/c1-19(2)10-6-11-21(5)17(19)9-12-22-13-16(7-8-18(21)22)23(14-22)15-24-20(3,4)25-23/h16-18H,6-15H2,1-5H3/t16-,17-,18+,21-,22+,23+/m1/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 ent-16beta,17-Isopropylidenedioxykaurane

The herb of Siegesbeckia orientalis.

ent-16beta,17-Isopropylidenedioxykaurane Dilution Calculator

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ent-16beta,17-Isopropylidenedioxykaurane Molarity Calculator

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Preparing Stock Solutions of ent-16beta,17-Isopropylidenedioxykaurane

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8852 mL 14.4259 mL 28.8517 mL 57.7034 mL 72.1293 mL
5 mM 0.577 mL 2.8852 mL 5.7703 mL 11.5407 mL 14.4259 mL
10 mM 0.2885 mL 1.4426 mL 2.8852 mL 5.7703 mL 7.2129 mL
50 mM 0.0577 mL 0.2885 mL 0.577 mL 1.1541 mL 1.4426 mL
100 mM 0.0289 mL 0.1443 mL 0.2885 mL 0.577 mL 0.7213 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 ent-16beta,17-Isopropylidenedioxykaurane

The natural diterpene ent-16beta-17alpha-dihydroxykaurane down-regulates Bcl-2 by disruption of the Ap-2alpha/Rb transcription activating complex and induces E2F1 up-regulation in MCF-7 cells.[Pubmed:21850486]

Apoptosis. 2011 Dec;16(12):1245-52.

ent-Kauranes are diterpene-type compounds commonly found in most plant species, especially from the Euphorbiaceae family. These compounds have been studied due to their anti-inflammatory and anti-tumor properties. Regulation of apoptosis, or programmed cell death, is commonly bypassed by tumoral cells, giving rise to uncontrolled proliferating cells, which eventually become carcinogenic. In a previous work, we showed that both mRNA and protein expression levels of the antiapoptotic gene Bcl-2 are reduced in MCF-7 cancer cells by the effect of the natural diterpene ent-16beta-17alpha-dihydroxykaurane (DHK). This effect was not directly associated with the inactivation of NF-kappaB, as has been shown with other diterpenes compounds. Herein, we report that DHK is dissociating the Ap2alpha-Rb activating complex, affecting its binding ability for the Bcl-2 gene promoter. These events down-regulate Bcl-2 and is temporally accompanied by the induction of E2F1 and its target pro-apoptotic gene Puma. Disruption of the Rb-Ap2alpha activation complex was corroborated by chromatin immunoprecipitation and protein immunolocalization, which also revealed that Ap2alpha sorts out from the nucleus and relocalizes in the cell periphery. Taken together, our study confirms the regulation of Bcl-2 gene transcription by the Ap2alpha-Rb complex and describes a singular protein relocalization for Ap2alpha induced by DHK, implicating a new potential therapeutic target to differentially onset apoptosis in tumor cells.

Ent-16beta,17-dihydroxy-kauran-19-oic acid, a kaurane diterpene acid from Siegesbeckia pubescens, presents antiplatelet and antithrombotic effects in rats.[Pubmed:21377851]

Phytomedicine. 2011 Jul 15;18(10):873-8.

The antiplatelet and antithrombotic effects of ent-16beta,17-dihydroxy-kauran-19-oic acid (DDKA) isolated from Siegesbeckia pubescens were investigated with different methods both in vitro and in vivo. We tested the antithrombotic activity of DDKA in arterio-venous shunt model. The effects of DDKA on adenosine diphosphate (ADP)-, Thrombin-, Arachidonic acid-induced rat platelets aggregation were tested in vitro. We also assessed its bleeding side effect by measuring coagulation parameters after intravenous administration for 5 days and investigated the potential mechanisms underlying such activities. In vivo, DDKA significantly reduced thrombus weight in the model of arterio-venous shunt. Meanwhile, DDKA increased plasma cAMP level determined by radioimmunoassay in the same model. Notably, DDKA prolonged PT and APTT in rats after intravenous administration DDKA for successive 5 days. In vitro, pretreatment with DDKA on washed rat platelets significantly inhibited various agonists stimulated platelet aggregation and caused an increase in cAMP level in platelets activated by ADP. These findings support our hypothesis that DDKA possesses antiplatelet and antithrombotic activities. The mechanisms underlying such activities may involve the anticoagulatory effect and cAMP induction.

Cytotoxic and proapoptotic activity of ent-16beta-17alpha-dihydroxykaurane on human mammary carcinoma cell line MCF-7.[Pubmed:15639346]

Cancer Lett. 2005 Jan 31;218(1):109-16.

Here we describe the cytotoxic and proapoptotic effect of an ent-kaurane (ent-16beta-17alpha-dihydroxykaurane), compound isolated from Croton malambo barks, on malignant cell growth. When MCF-7 mammary carcinoma cells were treated with increasing concentrations of the ent-kauranoid, its cytotoxic activity showed an IC50 of 12.5microg/ml, dose that is 2.66-fold lower than the corresponding value for non-malignant cells. At this growth inhibitory dose, both mRNA and protein levels for Bcl-2 as well as mRNA for hTERT were significantly reduced. The observed preapoptotic activity seemed to be triggered by a mechanism that is not directly affecting NF-(kappa)B binding ability. The potential use of this plant-derived compound as a cancer chemotherapy agent is discussed.

Simultaneous quantification of Kirenol and ent-16beta,17-dihydroxy-kauran-19-oic acid from Herba Siegesbeckiae in rat plasma by liquid chromatography-tandem mass spectrometry and its application to pharmacokinetic studies.[Pubmed:24008120]

J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Oct 15;937:18-24.

A rapid and specific liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) method was developed for the simultaneous determination of two active diterpenoids: Kirenol and ent-16beta,17-dihydroxy-kauran-19-oic acid (DHKA) from Herba Siegesbeckiae in rat plasma using osthole as an internal standard (IS). Plasma sample pretreatment involved a one-step liquid-liquid extraction with ethyl acetate. Chromatographic separation was performed on a Waters Symmetry C18 column (2.1mmx100mm, 3.5mum) with isocratic elution using methanol-5mmol/L aqueous ammonium acetate (80:20, v/v) as the mobile phase at a flow rate of 0.2mL/min. The detection was performed on a triple quadrupole tandem mass spectrometer in multiple reaction monitoring (MRM) mode under positive and negative electrospray ionization. The calibration curves were linear over the range of 50.0-25,000ng/mL for Kirenol, and 25.0-12,500ng/mL for DHKA. The extraction recoveries of the two analytes and the IS were all over 85%. The intra- and inter-day precision (relative standard deviation) values were less than 16.8% and the accuracy (relative error) ranged from -10.7 to 10.6% at four quality control levels. The validated method was successfully applied to a comparative pharmacokinetic study of the two diterpenoids in rat plasma after intragastric administration of Kirenol, DHKA and Herba Siegesbeckiae extract. The results showed that there were obvious differences between the pharmacokinetic behaviors after oral administration of Herba Siegesbeckiae extract compared with each of the substances alone.

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