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12-Oleanene-3,6-diol

CAS# 41498-79-7

12-Oleanene-3,6-diol

Catalog No. BCN3903----Order now to get a substantial discount!

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Quality Control of 12-Oleanene-3,6-diol

Number of papers citing our products

Chemical structure

12-Oleanene-3,6-diol

3D structure

Chemical Properties of 12-Oleanene-3,6-diol

Cas No. 41498-79-7 SDF Download SDF
PubChem ID 3084830 Appearance Cryst.
Formula C30H50O2 M.Wt 442.72
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S,4aR,5R,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,5-diol
SMILES CC1(CCC2(CCC3(C(=CCC4C3(CC(C5C4(CCC(C5(C)C)O)C)O)C)C2C1)C)C)C
Standard InChIKey JYNBNJRQZZSLPN-NYVWVNPOSA-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 12-Oleanene-3,6-diol

The herbs of Celastrus orbiculatus Thunb.

Biological Activity of 12-Oleanene-3,6-diol

Description12-Oleanene-3,6-diol has antitumor activity, it can induce apoptosis and has inhibition effect on the proliferation in RKO cell line.
In vitro

Antitumor effects of novel triterpene from Celastrus hypoleucus on human colorectal cancer cell line RKO in vitro.[Reference: WebLink]

China journal of Chinese materia medica, 2006, 31(17):1450-1453.

To investigate the effects of novel triterpene (12-Oleanene-3,6-diol ) from Celastrus hypoleucus on the proliferation and apoptosis of human colorectal cancer cell line RKO.
METHODS AND RESULTS:
The inhibitory effect of the novel triterpene on RKO cell proliferation was assayed by MTT dye reduction. The morphology of apoptotic cells was observed with AO/EB double fluorescence staining and HE staining, DNA fragment with electrophoresis on agarose gels, sub-diploid peak and cell cycle with flow cytometer (FCM). Novel triterpene (12-Oleanene-3,6-diol) from C. hypoleucus significantly inhibited proliferation of RKO cells in dose-dependent and time-dependent manner, the IC50 was (12.20 +/- 0.79) microg x mL(-1) at 48 h. Typical apoptotic changes were observed in RKO cells under the fluorescence microscope and the light microscope. DNA ladder was detected on agarose gels at concentrations from 10 microg x mL(-1) to 20 microg x mL(-1) at 48 h. With FCM methods, dose-dependent apoptosis-induced effect was observed in RKO cell line after treatment of triterpene for 48 h, and the apoptotic rates were increased from(2.93 +/- 0.84) % to (50.79 +/- 6.61) % at concentrations from 2.5 microg x mL(-1) to 20 microg x mL(-1). DNA histograms data from FCM analysis showed that the number of cells was obviously reduced during G0-G1 phase and G2-M phase, but not during S phase for RKO cell line after treatment with various concentrations of the triterpene for 48 hours.
CONCLUSIONS:
Novel triterpene (12-Oleanene-3,6-diol) from C. hypoleucus can induce apoptosis and has inhibition effect on the proliferation in RKO cell line.

Oleanen induces apoptosis of cervical cancer cells by up-regulation of Bim.[Reference: WebLink]

International Journal of Gynecological Cancer, 2012, 22(1):38-42.

Plants belonging to the genus Celastrus exhibit antitumor activity and the ability to reverse multidrug resistance in tumor cells; however, it remains unclear whether the compound oleanen from Celastrus hypoleucus also exhibits antitumor activity. The objective of this study was to explore the inhibitory effect of 12-oleanene-3β, 6α-diol (12-Oleanene-3,6-diol, oleanen) on the proliferation of cervical cancer HeLa cells in vitro, as well as its relative mechanism.
METHODS AND RESULTS:
HeLa cells were treated with different concentrations of oleanen for different times. Cell proliferation was determined by 3-(4,5)-dimethylthiahiazo (-z-y1)-3,5-di-phenytetrazoliumromide assay. Cell apoptosis was evaluated by flow cytometry and caspases activities assay. The expression of several proapoptotic proteins belonging to the Bcl-2 family, such as Bax, Bim, and Bad, was detected by Western blot. RESULTS:Oleanen mainly inhibited the proliferation of HeLa cells at the G0 to G1 and G2 to M phases, and the IC50 of oleanen for cells was significantly higher at 24 hours compared to 48 hours (17.45 ± 3.71 vs 9.02 ± 0.83 μg/mL, respectively; P < 0.05). The significant increase in activity of caspase 3/7, caspase 6 in oleanen-treated HeLa cells indicated that oleanen promoted the apoptosis of HeLa cells. The activity of caspase 9 representing the endogenous apoptotic pathways also increased obviously in oleanen treatment. Furthermore, the increase in the expression of Bim was the most significant among the Bcl-2 family after oleanen treatment.
CONCLUSIONS:
Oleanen up-regulates the expression of Bim and other proapoptotic molecules to activate the endogenous apoptosis pathway, thus promoting apoptosis and inhibiting proliferation of human cervical cancer HeLa cells in vitro.

12-Oleanene-3,6-diol Dilution Calculator

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Preparing Stock Solutions of 12-Oleanene-3,6-diol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2588 mL 11.2938 mL 22.5876 mL 45.1753 mL 56.4691 mL
5 mM 0.4518 mL 2.2588 mL 4.5175 mL 9.0351 mL 11.2938 mL
10 mM 0.2259 mL 1.1294 mL 2.2588 mL 4.5175 mL 5.6469 mL
50 mM 0.0452 mL 0.2259 mL 0.4518 mL 0.9035 mL 1.1294 mL
100 mM 0.0226 mL 0.1129 mL 0.2259 mL 0.4518 mL 0.5647 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 12-Oleanene-3,6-diol

(1S,2E,4S,7E,11E)-2,7,11-Cembratriene-4,6-diol semisynthetic analogs as novel c-Met inhibitors for the control of c-Met-dependent breast malignancies.[Pubmed:27681240]

Bioorg Med Chem. 2016 Nov 15;24(22):5748-5761.

(1S,2E,4S,6R,7E,11E)-2,7,11-Cembratriene-4,6-diol (1) and its 4-epi-analog (2) are the cembranoid precursors to several key flavor ingredients in most Nicotiana (tobacco) species. Nearly 40-60% of 1 and 2 are purposely degraded during the commercial tobacco fermentation. However, 1 and 2 display promising bioactivities, including anticancer. Breast cancer is the most diagnosed cancer in women and ranked second female disease killer. The receptor tyrosine kinase c-Met correlates with aggressiveness of certain breast cancer phenotypes and thus considered a valid therapeutic target. This study reports the discovery and optimization of the tobacco-based cembranoid 1 as a novel c-Met inhibitory scaffold using combined structure- and ligand-based approaches. 1 displayed antiproliferative, anti-migratory and anti-invasive effects against the c-Met overexpressing MDA-MB-231 breast cancer cells at moderate muM concentrations. The Z'-LYTE kinase platform and Western blot analysis identified c-Met as a potential macromolecular target. Rationally designed carbamate analogs were proposed to probe additional targeted c-Met interactions and improve the cellular potency. The 6-phenyl carbamate 3 showed enhanced c-Met inhibitory activity. Structure-activity relationships of different substituents on the 3's phenyl moiety were studied. The most active analog 20 showed potent in vitro anticancer activity against the MDA-MB-231 breast cancer cells at low muM concentrations, with minimal toxicity on the non-tumorigenic MCF-10A mammary epithelial cells. Cembranoid 20 potently inhibited the c-Met catalytic activity in Z'-LYTE kinase assay and various cellular c-Met-driven signaling pathways. Furthermore, 20 displayed a robust antitumor activity in a breast cancer xenograft athymic mouse model and thus promoted to the lead rank. Cembranoids are novel c-Met inhibitors appropriate for future use to control c-Met dependent malignancies.

Neuroprotective activity of (1S,2E,4R,6R,-7E,11E)-2,7,11-cembratriene-4,6-diol (4R) in vitro and in vivo in rodent models of brain ischemia.[Pubmed:25677097]

Neuroscience. 2015 Apr 16;291:250-259.

(1S,2E,4R,6R,-7E,11E)-2,7,11-cembratriene-4,6-diol (4R) is a precursor to key flavor ingredients in leaves of Nicotiana species. The present study shows 4R decreased brain damage in rodent ischemic stroke models. The 4R-pretreated mice had lower infarct volumes (26.2+/-9.7 mm3) than those in control groups (untreated: 63.4+/-4.2 mm3, DMSO: 60.2+/-14.2 mm3). The 4R-posttreated rats also had less infarct volumes (120+/-65 mm3) than those in the rats of the DMSO group (291+/-95 mm3). The results from in vitro experiments indicate that 4R decreased neuro2a cell (neuroblastoma cells) apoptosis induced by oxygen-glucose deprivation (OGD), and improved the population spikes' (PSs) recovery in rat acute hippocampal slices under OGD; a phosphatidylinositol 3-kinase (PI3K) inhibitor, wortmannin, abolished the effect of 4R on PSs recovery. Furthermore, 4R also inhibited monocyte adhesion to murine brain-derived endothelial (bEND5) cells and upregulation of intercellular adhesion molecule-1(ICAM-1) induced by OGD/reoxygenation (OGD/R), and restored the p-Akt level to pre-OGD/R values in bEND5 cells. In conclusion, the present study indicates that 4R has a protective effect in rodent ischemic stroke models. Inhibition of ICAM-1 expression and restoration of Akt phosphorylation are the possible mechanisms involved in cellular protection by 4R.

The tobacco cembranoid (1S,2E,4S,7E,11E)-2,7,11-cembratriene-4,6-diol as a novel angiogenesis inhibitory lead for the control of breast malignancies.[Pubmed:28583806]

Bioorg Med Chem. 2017 Aug 1;25(15):3911-3921.

(1S,2E,4S,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (1) and its 4-epi-analog (2) are diterpene precursors of the key flavor components in most Nicotiana (tobacco) species that purposely degraded during commercial tobacco fermentation. Angiogenesis, recruitment of new blood vessels, is important for tumor growth, survival and metastasis that can be targeted to control cancer. This study shows evidences and potential of the cembranoid 1 as a potent angiogenesis modulator through targeting VEGFR2. In silico study suggested favorable docking scores and binding affinity of 1 at the ATP binding pocket of VEGFR2. The binding mode of 1 was parallel to the standard FDA-approved antiangiogenic drug sunitinib (4). In vitro, cembranoid 1 significantly reduced the activated VEGFR2 levels in multiple breast cancer cell lines. Intraperitoneal 40mg/kg, 3X/week treatment of 1 significantly reduced the MDA-MB-231 cells breast tumor size in mice. Immunohistochemistry and Western blotting analysis of the treated mice tumors showed significant downregulation of the vasculogenesis marker CD31 and suppressed activated VEGFR2-paxillin-FAK pathway. Matrigel study in Swiss albino mice showed similar trend. The tobacco cembranoid 1 is a potential antiangiogenic lead useful for future use to control breast malignancies.

Design and Synthesis of 2-Alkylpyrimidine-4,6-diol and 6-Alkylpyridine-2,4-diol as Potent GPR84 Agonists.[Pubmed:27326330]

ACS Med Chem Lett. 2016 Mar 30;7(6):579-83.

A series of alkylpyrimidine-4,6-diol derivatives were designed and synthesized as novel GRP84 agonists based on a high-throughput screening (HTS) hit 1. 6-Nonylpyridine-2,4-diol was identified as the most potent agonist of GPR84 reported so far, with an EC50 of 0.189 nM. These novel GPR84 agonists will provide valuable tools for the study of the physiological functions of GPR84.

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