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Dihydrocelastrol (DHCE; Triptohypol C) is a terpene derivative synthesized by hydrogenation of celastrol, which is a naturally occurring treterpene isolated from Chinese medicinal plant Tripterygium regelii. Dihydrocelastrol has anticaner activity by inhibiting cell proliferation and promote apoptosis through caspase-dependent way in vitro. DHCE could inhibit cellular proliferation and induce cell apoptosis in myeloma cells mediated through different mechanisms, possibly through inhibiting the IL-6/STAT3 and ERK1/2 pathways. Dihydrocelastrol is also a potent Nur77-targeting anti-inflammatory agent with an Kd value of 0.87 μM, inhibiting inflammatory response by promoting the interactions of Nur77 with TRAF2 and p62/SQSTM1.
| Targets |
Nur77; Natural pentacyclic triterpenoid; anti-inflammatory agent
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| ln Vitro |
Triptohypol C (compound 3a) (2 μM; 1 h) potently counteracts TNFα's ability to cause IκBα degradation and suppresses the inflammatory response via facilitating Nur77's interactions with TRAF2 and p62/SQSTM1[1]. Less hazardous than tripterin, triptohypol C (2 μM; 10 h) causes 3.12% apoptosis in HepG2 cells[1].
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| ln Vivo |
Dihydrocelastrol (Compounds 3a) and 1e displayed similar anti-inflammatory effects as celastrol and were selected for further biological evaluation. 3a was found to be less toxic when its toxicity was assessed in comparison to celastrol in zebrafish model. It is worth noting that celastrol and analogs have been widely studied for their anti-cancer potentials, but less studied for their anti-inflammatory applications. This study will provide insights into the optimization of celastrol derivatives selectively targeting Nur77 for anti-inflammatory therapy.[1]
Dihydrocelastrol/Triptohypol C induced apoptosis in cells at a rate of 3.12%; this was less cytotoxic than tripterin (>10%). |
| Enzyme Assay |
The binding characterization of celastrol to Nur77 was recently reported. It was demonstrated that celastrol binds to Nur77-LBD via specific noncovalent interactions and a reversible covalent bond. It was also showed that covalent bond is formed through Michael addition reaction between celastrol and C551 in Nur77. Furthermore, researchers developed a binding model of celastrol to Nur77 by using molecular modeling and mutagenesis approaches. In this predicted model (Fig. 2A), celastrol fits well to a groove.[1]
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| Cell Assay |
Western Blot Analysis[1]
Cell Types: Lysates from HepG2 cells (incubated with 20 ng/mL TNFα for 30 min) Tested Concentrations: 2 μM Incubation Duration: 1 h Experimental Results: Strongly antagonized the effect of TNFα on inducing IκBα degradation Immunofluorescence[1] Cell Types: HepG2 cells (transfected with Myc-Nur77 and Flag-TRAF2 or Flag-p62) Tested Concentrations: 2 μM Incubation Duration: 1 h Experimental Results: Promoted the interactions between Nur77 and TRAF2 and p62/SQSTM1. Apoptosis Analysis[1] Cell Types: HepG2 cells Tested Concentrations: 2 μM Incubation Duration: 10 h Experimental Results: Caused 3.12% apoptosis in cells, which was less cytotoxic than Tripterin (> 10%). |
| Animal Protocol |
Animal/Disease Models: Zebrafish[1]
Doses: 0.5 μM, 1 μM and 1.25 μM Route of Administration: 72 h Experimental Results: Had less effect than Tripterin on the death rate and malformation of zebrafish either at a concentration of 1.25 μM for 24 h or at a concentration of 0.5 μM for 72 h. |
| References | |
| Additional Infomation |
Triptohypol C is a pentacyclic triterpenoid with formula C29H40O4, originally isolated from the root bark of Tripterygium regelii. It has a role as a plant metabolite and an apoptosis inducer. It is a pentacyclic triterpenoid, a monocarboxylic acid and a member of benzenediols.
Dihydrocelastrol has been reported in Tripterygium wilfordii and Tripterygium hypoglaucum with data available. |
| Molecular Formula |
C29H40O4
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|---|---|
| Molecular Weight |
452.635
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| Exact Mass |
452.292
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| Elemental Analysis |
C, 76.95; H, 8.91; O, 14.14
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| CAS # |
193957-88-9
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| Related CAS # |
34157-83-0 (castrol);193957-88-9 (dihydrocelastrol);
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| PubChem CID |
10411574
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.21±0.1 g/cm3
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| Boiling Point |
596.0±50.0 °C
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| Source |
Tripterygium wilfordii; Tripterygium hypoglaucum
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| LogP |
7.3
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
33
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| Complexity |
881
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| Defined Atom Stereocenter Count |
6
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| SMILES |
CC1=C2CC=C3[C@](C2=CC(=C1O)O)(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4C[C@](CC5)(C)C(=O)O)C)C)C)C
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| InChi Key |
WZAUFGYINZYCKH-JJWQIEBTSA-N
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| InChi Code |
InChI=1S/C29H40O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h8,15,22,30-31H,7,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
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| Chemical Name |
(2R,4aS,6aS,12bS,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid
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| Synonyms |
(-)-Triptohypol C; Dihydrocelastrol; Triptohypol C; 193957-88-9; (2R,4aS,6aS,12bS,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid; CHEMBL1092797; SCHEMBL18850315; CHEBI:132340; DTXSID801346962; DHCE; Triptohypol C.
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2093 mL | 11.0463 mL | 22.0926 mL | |
| 5 mM | 0.4419 mL | 2.2093 mL | 4.4185 mL | |
| 10 mM | 0.2209 mL | 1.1046 mL | 2.2093 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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