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| Targets |
δ-Amyrenone targets inflammatory pathways, acting as a specific inhibitor of cyclooxygenase-2 (COX-2). By inhibiting COX-2, the compound reduces the production of pro-inflammatory prostaglandins, thereby exerting its anti-inflammatory effects. The compound's anti-inflammatory activity may be relevant to the regulation of COX-2 and inflammatory signaling pathways. Further studies are needed to fully characterize its molecular targets and mechanism of action.
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| ln Vitro |
In vitro, δ-Amyrenone exhibits anti-inflammatory effects through inhibition of COX-2. As a pentacyclic triterpene from S. lineare, it may modulate inflammatory cytokine production and reduce inflammatory responses in cell-based assays. The compound's ability to inhibit COX-2 suggests potential activity in reducing prostaglandin synthesis. However, detailed in vitro activity data including IC₅₀ values have not been extensively published.
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| ln Vivo |
In mice, δ-amyrone (4 mg/kg and 8 mg/kg; ip) prevents endotoxic shock by inhibiting inflammatory cytokines generated by lipopolysaccharide[1].
In vivo, δ-Amyrenone (4 mg/kg and 8 mg/kg; intraperitoneal injection) inhibits lipopolysaccharide-induced inflammatory cytokines and protects mice from endotoxin shock. This demonstrates that the compound has significant anti-inflammatory activity in animal models of systemic inflammation. The compound's ability to protect against endotoxin shock suggests potential therapeutic applications in inflammatory conditions. Further studies are needed to evaluate its efficacy in other inflammatory disease models. |
| Enzyme Assay |
In vitro COX-2 inhibition assays for δ-Amyrenone typically involve measuring the enzymatic activity of COX-2 in the presence of varying concentrations of the compound. The enzyme is incubated with arachidonic acid substrate, and prostaglandin production is quantified by ELISA or other immunoassays. IC₅₀ values are calculated from dose-response curves. The compound's structure can be confirmed by NMR and MS. Purity is assessed by HPLC (≥98.50%).
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| Cell Assay |
In vitro cellular assays for δ-Amyrenone typically involve evaluation of anti-inflammatory activity in immune cells such as macrophages. Cells are treated with the compound and stimulated with LPS or other inflammatory stimuli, and cytokine production (TNF-α, IL-1β, IL-6) is measured by ELISA. Nitric oxide production can be measured using the Griess assay. Cytotoxicity is assessed using standard cell viability assays to ensure that observed anti-inflammatory effects are not due to cell death.
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| Animal Protocol |
In vivo animal experiments for δ-Amyrenone have been conducted in mouse models of endotoxin shock. Mice are administered δ-Amyrenone at doses of 4 mg/kg and 8 mg/kg via intraperitoneal injection. Following LPS challenge, inflammatory cytokine levels are measured, and survival is monitored. The compound inhibits LPS-induced inflammatory cytokines and protects mice from endotoxin shock. Endpoints include cytokine quantification and survival analysis.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of δ-Amyrenone have not been extensively characterized. The compound has a molecular weight of 424.70 g/mol and a molecular formula of C₃₀H₄₈O. As a lipophilic pentacyclic triterpene, it is expected to have reasonable membrane permeability and oral bioavailability. The compound is typically stored as a powder under desiccated conditions. Further pharmacokinetic studies including absorption, distribution, metabolism, and excretion would be needed to characterize its in vivo behavior.
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| Toxicity/Toxicokinetics |
The toxicological profile of δ-Amyrenone has not been extensively documented. As a naturally occurring triterpene from S. lineare, it is expected to have a relatively favorable safety profile. However, comprehensive toxicological evaluations including acute toxicity, genotoxicity, and repeated-dose studies have not been reported. Standard laboratory safety precautions should be followed when handling this compound.
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| References |
[1]. Niu X, et al.δ-Amyrone, a specific inhibitor of cyclooxygenase-2, exhibits anti-inflammatory effects in vitro and in vivo of mice. Int Immunopharmacol. 2014 Jul;21(1):112-8.
[2]. Niu X, et al.δ-Amyrone inhibits lipopolysaccharide-induced inflammatory cytokines and protects against endotoxic shock in mice. Chem Biol Interact. 2015 Oct 5;240:354-61. |
| Additional Infomation |
According to reports, 13(18)-oleanene-3-one has been found in Euphorbia species, Eupatorium fortunei, and other organisms with available data.
δ-Amyrenone (CAS# 20248-08-2, molecular formula C₃₀H₄₈O, molecular weight 424.70) is a pentacyclic triterpene compound from S. lineare with anti-inflammatory effects. It is a specific inhibitor of cyclooxygenase-2 (COX-2). Also known as Delta-Amyrone. No clinical trials or regulatory approvals have been identified. Purity ≥98.50%. |
| Molecular Formula |
C30H48O
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|---|---|
| Molecular Weight |
424.70
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| Exact Mass |
424.37
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| CAS # |
20248-08-2
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| PubChem CID |
14079468
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| Appearance |
White to off-white solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
488.8±44.0 °C at 760 mmHg
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| Flash Point |
203.1±23.4 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.534
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| LogP |
10.51
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
31
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| Complexity |
845
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| Defined Atom Stereocenter Count |
6
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| SMILES |
CC1(C)CC[C@]2(C)CC[C@]3(C)C(=C2C1)CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C
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| InChi Key |
KPUDOJPVQQJLGI-CKARLABJSA-N
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| InChi Code |
InChI=1S/C30H48O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h22-23H,9-19H2,1-8H3/t22-,23+,27+,28-,29+,30+/m0/s1
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| Chemical Name |
(4aR,6aR,6bS,8aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-2,4a,5,6,7,8,9,10,12,13,14,14a-dodecahydro-1H-picen-3-one
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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 | 2.3546 mL | 11.7730 mL | 23.5460 mL | |
| 5 mM | 0.4709 mL | 2.3546 mL | 4.7092 mL | |
| 10 mM | 0.2355 mL | 1.1773 mL | 2.3546 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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