TriptonideCAS# 38647-11-9 |
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Quality Control & MSDS
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| Cas No. | 38647-11-9 | SDF | Download SDF |
| PubChem ID | 65411 | Appearance | White-beige powder |
| Formula | C20H22O6 | M.Wt | 358.39 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Synonyms | NSC 165677; PG 492 | ||
| Solubility | DMSO : 50 mg/mL (139.51 mM; Need ultrasonic) | ||
| SMILES | CC(C)C12C(O1)C3C4(O3)C5(CCC6=C(C5CC7C4(C2=O)O7)COC6=O)C | ||
| Standard InChIKey | SWOVVKGLGOOUKI-ZHGGVEMFSA-N | ||
| Standard InChI | InChI=1S/C20H22O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14H,4-7H2,1-3H3/t11-,12-,13-,14-,17-,18-,19+,20+/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 | Triptonide is effective in the treatment of autoimmune diseases and has potent antileukemic and antitumor activities, it possesses anti-inflammatory activity, upregulate the expression of IL-37, and this expression was suppressed by ERK1/2 and p38 MAPK inhibitors. |
| Targets | ERK | IL Receptor | GSK-3 | p38MAPK | Wnt/β-catenin |
| In vivo | Effects of triptonide on mouse immune functions.[Pubmed: 8237400]Zhongguo Yao Li Xue Bao. 1993 May;14(3):238-42.
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| Kinase Assay | Triptonide Effectively Inhibits Wnt/β-Catenin Signaling via C-terminal Transactivation Domain of β-catenin.[Pubmed: 27596363]Modulation of IL-37 expression by triptolide and triptonide in THP-1 cells.[Pubmed: 25308753]Cell Mol Immunol. 2014 Oct 13.IL-37 is an anti-inflammatory cytokine that was only recently identified, and it is highly expressed in tissues from patients with inflammatory and autoimmune diseases. Inflammatory cytokines and inflammatory stimuli can induce the upregulation of IL-37. However, it has not been reported whether anti-inflammatory medications induce the expression of IL-37.
Sci Rep. 2016 Sep 6;6:32779.Abnormal activation of canonical Wnt/β-catenin signaling is implicated in many diseases including cancer. As a result, therapeutic agents that disrupt this signaling pathway have been highly sought after. Triptonide is a key bioactive small molecule identified in a traditional Chinese medicine named Tripterygium wilfordii Hook F., and it has a broad spectrum of biological functions. Here we show that Triptonide can effectively inhibit canonical Wnt/β-catenin signaling by targeting the downstream C-terminal transcription domain of β-catenin or a nuclear component associated with β-catenin. In addition, Triptonide treatment robustly rescued the zebrafish "eyeless" phenotype induced by GSK-3β antagonist 6-bromoindirubin-30-oxime (BIO) for Wnt signaling activation during embryonic gastrulation. Finally, Triptonide effectively induced apoptosis of Wnt-dependent cancer cells, supporting the therapeutic potential of Triptonide. |
| Animal Research | Effect of triptonide on inflammation and immunity function.[Reference: WebLink]Chinese Journal of Hospital Pharmacy, 2006, 26(6):695-7.
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Triptonide Dilution Calculator
Triptonide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7903 mL | 13.9513 mL | 27.9026 mL | 55.8051 mL | 69.7564 mL |
| 5 mM | 0.5581 mL | 2.7903 mL | 5.5805 mL | 11.161 mL | 13.9513 mL |
| 10 mM | 0.279 mL | 1.3951 mL | 2.7903 mL | 5.5805 mL | 6.9756 mL |
| 50 mM | 0.0558 mL | 0.279 mL | 0.5581 mL | 1.1161 mL | 1.3951 mL |
| 100 mM | 0.0279 mL | 0.1395 mL | 0.279 mL | 0.5581 mL | 0.6976 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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Triptonide(NSC 165677; PG 492) is dCTP Pyrophosphatase inhibitor.
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Cytotoxic biotransformed products from triptonide by Aspergillus niger.[Pubmed:14598204]
Planta Med. 2003 Sep;69(9):804-8.
The diterpenoid triepoxides are the major active constituents of Tripterygium wilfordii with potent antitumor and immune activities. But the strong toxicity of these compounds has restricted their application to a great extent. In order to find more effective compounds with less toxicity, structural modifications of Triptonide (1) by Aspergillus niger (AS 3.739) were investigated and four biotransformed products were obtained. Based on their chemical and spectral data, their structures were elucidated as 5alpha-hydroxyTriptonide (2), triptolide (3), 17-hydroxyTriptonide (4), and 16-hydroxyTriptonide (5), among which 2, 4 and 5 are new compounds. All the three new transformed products showed cytotoxic activities against the majority of the human tumor cell lines tested, however, they are found to possess less cytotoxic activity when compared with 1. Both compounds 4 and 5 showed similar cytotoxic activity and their IC (50) values were 5-15 fold less than 1, while 2 is about 100 times less active than 1.
Triptonide Effectively Inhibits Wnt/beta-Catenin Signaling via C-terminal Transactivation Domain of beta-catenin.[Pubmed:27596363]
Sci Rep. 2016 Sep 6;6:32779.
Abnormal activation of canonical Wnt/beta-catenin signaling is implicated in many diseases including cancer. As a result, therapeutic agents that disrupt this signaling pathway have been highly sought after. Triptonide is a key bioactive small molecule identified in a traditional Chinese medicine named Tripterygium wilfordii Hook F., and it has a broad spectrum of biological functions. Here we show that Triptonide can effectively inhibit canonical Wnt/beta-catenin signaling by targeting the downstream C-terminal transcription domain of beta-catenin or a nuclear component associated with beta-catenin. In addition, Triptonide treatment robustly rescued the zebrafish "eyeless" phenotype induced by GSK-3beta antagonist 6-bromoindirubin-30-oxime (BIO) for Wnt signaling activation during embryonic gastrulation. Finally, Triptonide effectively induced apoptosis of Wnt-dependent cancer cells, supporting the therapeutic potential of Triptonide.
Effects of triptonide on mouse immune functions.[Pubmed:8237400]
Zhongguo Yao Li Xue Bao. 1993 May;14(3):238-42.
Triptonide (Tri) extracted from Tripterygium wilfordii Hook inhibited the proliferation of mouse splenocytes induced by suboptimal concentration of concanavalin A or lipopolysaccharide at concentrations of 0.02, 0.1, and 0.5 microgram.ml-1. It showed a suppressive effect on one way mixed lymphocyte culture (MLC) at 0.1-0.4 microgram.ml-1. The lymphocytes harvested from the first Tri (0.4 microgram.ml-1)-containing MLC inhibited the second MLC after being washed and irradiated with 60Co source (30 Gy). Serum anti-sheep red blood cell antibody (hemolysin) formation and clearance of charcoal particles were also suppressed by Tri in vivo. Although delayed hypersensitivity (DH) reaction to dinitrofluorobenzene (DNFB) was inhibited by Tri 1.2, 2.5, and 5.0 mg.kg-1 (ip, qd x 5 d), the spleen cell interleukin-2 secretion activities of these mice were not suppressed. Graft vs host reaction (GVHR) was not inhibited by Tri 2.5 and 5.0 mg.kg-1 (ig, qd x 5 d). Helper T cells (Th)/suppressor T cells (Ts) ratio was reduced at 2.5 mg.kg-1. The effects of Tri on mouse thymus and spleen weight were related to the age. Tri (1.2, 2.5, 5.0 mg.kg-1) had no effect on thymus and spleen weights in 8-wk-old mice. However, it increased the thymus and spleen weights in 12-wk-old mice at doses of 1.2 and 2.5 mg.kg-1. The data indicated that Tri had extensive suppressive effects on mouse immune function and its mechanism may be related to the reduction of Th/Ts ratio and the induction of Ts cells.
Modulation of IL-37 expression by triptolide and triptonide in THP-1 cells.[Pubmed:25308753]
Cell Mol Immunol. 2015 Jul;12(4):515-8.
IL-37 is an anti-inflammatory cytokine that was only recently identified, and it is highly expressed in tissues from patients with inflammatory and autoimmune diseases. Inflammatory cytokines and inflammatory stimuli can induce the upregulation of IL-37. However, it has not been reported whether anti-inflammatory medications induce the expression of IL-37. In this work, we uncovered, for the first time, that two main bioactive components, triptolide and Triptonide, from the herb Tripterygium wilfordii Hook f. (TwHF), which possess anti-inflammatory activity, upregulate the expression of IL-37, and this expression was suppressed by ERK1/2 and p38 MAPK inhibitors. Overall, our research demonstrated, for the first time, that anti-inflammatory active components (triptolide and Triptonide) upregulated the expression of IL-37 most likely via activation of the ERK1/2 and p38 MAPK pathways.Cellular & Molecular Immunology advance online publication, 6 October 2014; doi:10.1038/cmi.2014.92.
