TaraxerolCAS# 127-22-0 |
- Epitaraxerol
Catalog No.:BCN4677
CAS No.:20460-33-7
Quality Control & MSDS
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| Cas No. | 127-22-0 | SDF | Download SDF |
| PubChem ID | 92097 | Appearance | White powder |
| Formula | C30H50O | M.Wt | 426.7 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Synonyms | Alnulin; Skimmiol; Tiliadin | ||
| Solubility | Soluble in chloroform and methanol; insoluble in water | ||
| Chemical Name | (3S,4aR,6aR,6aS,8aR,12aR,14aR,14bR)-4,4,6a,6a,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-ol | ||
| SMILES | CC1(CCC2(CC=C3C4(CCC5C(C(CCC5(C4CCC3(C2C1)C)C)O)(C)C)C)C)C | ||
| Standard InChIKey | GGGUGZHBAOMSFJ-GADYQYKKSA-N | ||
| Standard InChI | InChI=1S/C30H50O/c1-25(2)17-18-27(5)13-9-21-29(7)14-10-20-26(3,4)24(31)12-16-28(20,6)22(29)11-15-30(21,8)23(27)19-25/h9,20,22-24,31H,10-19H2,1-8H3/t20-,22+,23+,24-,27-,28-,29-,30+/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. |
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| 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. |
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| 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. | ||
| Description | 1. Taraxerol has potent anti-inflammatory effects,it downregulates the expression of proinflammatory mediators in macrophages by interfering with the activation of TAK1 and Akt, thus preventing NF-κB activation. 2. Taraxerol can produce triterpenoid anti-cancer compound in Agrobacterium-transformed root cultures of butterfly pea (Clitoria ternatea L.). 3. Taraxerol can be used as a lipid biomarker for mangrove input to the SE Atlantic. 4. Taraxerol has inhibitory effects on AGS cell growth through inducing G2/M arrest and promotion of cell apoptosis, taraxeryl acetate has less effect on cell cycle arrest and apoptosis of AGS cells than taraxerol. |
| Targets | NO | PGE | TNF-α | IL Receptor | NF-kB | TGF-β/Smad | Akt |
Taraxerol Dilution Calculator
Taraxerol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.3436 mL | 11.7178 mL | 23.4357 mL | 46.8713 mL | 58.5892 mL |
| 5 mM | 0.4687 mL | 2.3436 mL | 4.6871 mL | 9.3743 mL | 11.7178 mL |
| 10 mM | 0.2344 mL | 1.1718 mL | 2.3436 mL | 4.6871 mL | 5.8589 mL |
| 50 mM | 0.0469 mL | 0.2344 mL | 0.4687 mL | 0.9374 mL | 1.1718 mL |
| 100 mM | 0.0234 mL | 0.1172 mL | 0.2344 mL | 0.4687 mL | 0.5859 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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Production of triterpenoid anti-cancer compound taraxerol in Agrobacterium-transformed root cultures of butterfly pea (Clitoria ternatea L.).[Pubmed:22843061]
Appl Biochem Biotechnol. 2012 Oct;168(3):487-503.
Independent transformed root somaclones (rhizoclones) of butterfly pea (Clitoria ternatea L.) were established using explant co-cultivation with Agrobacterium rhizogenes. Rhizoclones capable of sustained growth were maintained under low illumination in auxin-free agar-solidified MS medium through subcultures at periodic intervals. Integration of T(L)-DNA rolB gene in the transformed rhizoclone genome was verified by Southern blot hybridization, and the transcript expression of T(R)-DNA ags and man2 genes was ascertained by reverse transcription polymerase chain reaction analysis. The major compound isolated and purified from the transformed root extracts was identified as the pentacyclic triterpenoid compound Taraxerol using IR, (1)H-NMR, and (13)C-NMR spectroscopy. The Taraxerol yield in cultured hairy roots, as quantified by HPTLC analysis, was up to 4-fold on dry weight basis compared to that in natural roots. Scanning of bands from cultured transformed roots and natural roots gave super-imposable spectra with standard Taraxerol, suggesting a remarkable homology in composition. To date, this is the first report claiming production of the cancer therapeutic phytochemical Taraxerol in genetically transformed root cultures as a viable alternative to in vivo roots of naturally occurring plant species.
A new taraxerol derivative from the roots of Microcos tomentosa.[Pubmed:24354177]
Nat Prod Commun. 2013 Oct;8(10):1371-2.
A new 3beta-O-vanilloyl-Taraxerol, microcisin (1) and eight known compounds, 3beta-Taraxerol acetate (2), 3beta-Taraxerol (3), cholest-4-en-3-one (4), cholest-4-en-6beta-ol-3-one (5), beta-sitosterol (6), 7-hydroxycadalene (7), mellein (8) and vanillin (9), were isolated from the roots of Microcos tomentosa. The structures were determined by extensive analysis of their spectroscopic data. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cells.
[Effects of taraxerol and taraxerol acetate on cell cycle and apoptosis of human gastric epithelial cell line AGS].[Pubmed:21669168]
Zhong Xi Yi Jie He Xue Bao. 2011 Jun;9(6):638-42.
OBJECTIVE: To investigate the effects of Taraxerol and Taraxerol acetate on cell cycle and apoptosis of human gastric epithelial cell line AGS cells. METHODS: The inhibitory effects of Taraxerol and Taraxerol acetate at different concentrations on AGS cell growth were measured by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) method and the concentrations of Taraxerol and Taraxerol acetate to be used in following experiments were decided. Then, cell cycle analysis was performed by FACScan flow cytometry after culture with Taraxerol or Taraxerol acetate. Annexin V-fluorescein isothiocyanate/propidium iodide staining was used to measure cell apoptosis. RESULTS: Taraxerol significantly inhibited AGS cell proliferation in a dose- and time-dependent manner. Taraxerol arrested the AGS cells at G(2)/M stage. 110 mumol/L Taraxerol elevated the population of AGS cells arrested in G(2)/M phase compared with solvent (P<0.05). Taraxerol also promoted early cell apoptosis in AGS cells. 110 mumol/L Taraxerol increased the early cell apoptosis rate from 4.45% to 10.29%, which was 1.31 times higher than that of the untreated cells. However, Taraxerol acetate had a lower inhibitory effect than Taraxerol, and it showed a tendency of G(2)/M arrest and apoptosis promotion but with no statistical significance (P>0.05). CONCLUSION: Taraxerol has inhibitory effects on AGS cell growth through inducing G(2)/M arrest and promotion of cell apoptosis. Taraxerol acetate has less effect on cell cycle arrest and apoptosis of AGS cells than Taraxerol.
Taraxerol inhibits LPS-induced inflammatory responses through suppression of TAK1 and Akt activation.[Pubmed:23333629]
Int Immunopharmacol. 2013 Feb;15(2):316-24.
Taraxerol, a triterpenoid compound, has potent anti-inflammatory effects. However, the molecular mechanisms are not clear. In the study, Taraxerol concentration dependently inhibited nitric-oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at the protein and mRNA levels and these inhibitions decreased the production of nitric oxide (NO), prostaglandin 2 (PGE2), tumor necrosis factor-alpha (TNF-alpha), interleukin (IL)-6, and IL-1beta induced by LPS. Furthermore, we found that Taraxerol suppressed translocation of nuclear factor-kappaB (NF-kappaB), phosphorylation of IkappaBalpha, blocked the IkappaBalpha degradation as well as IKK and mitogen-activated protein kinase (MAPK) activation by inactivation of TGF-beta-activated kinase-1 (TAK1) and Akt. In addition, Taraxerol significantly inhibited the formation of TAK1/TAK-binding protein1 (TAB1), which was accompanied by inducing degradation of TAK1, decreasing LPS-induced polyubiquitination of TAK1 as well as TAK1 phosphorylation. Taken together, our data suggest that Taraxerol downregulates the expression of proinflammatory mediators in macrophages by interfering with the activation of TAK1 and Akt, thus preventing NF-kappaB activation.
