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| 1mg |
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| 5mg |
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| Other Sizes |
| Targets |
(5alpha)-Stigmastane-3,6-dione modulates multiple inflammatory pathways, likely through inhibition of pro-inflammatory mediators such as nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor-alpha (TNF-alpha), and interleukin-6 (IL-6) in activated immune cells. Inflammatory signaling pathways such as nuclear factor-kappa B (NF-kappaB) and mitogen-activated protein kinase (MAPK) may be suppressed. Its antimicrobial activity is likely mediated through disruption of bacterial cell membrane integrity, as is common for many sterol compounds. The antifeedant activity against insects suggests interaction with insect chemosensory or digestive systems. The precise molecular targets have not been fully characterized, and further target identification studies are needed.
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| ln Vitro |
In vitro activity assays have demonstrated that (5alpha)-stigmastane-3,6-dione exhibits moderate antimicrobial activity against several bacterial strains. However, specific MIC values and detailed bactericidal profiles have not been extensively reported. Anti-inflammatory activity has been confirmed in cell-based assays using lipopolysaccharide (LPS)-stimulated macrophages, where the compound reduces the production of pro-inflammatory cytokines (TNF-alpha, IL-1beta, IL-6) and nitric oxide (NO) in a concentration-dependent manner. In vitro studies using human or murine immune cells have shown that (5alpha)-stigmastane-3,6-dione inhibits the activation of NF-kappaB and MAPK signaling pathways, which are central to the inflammatory response. The concentration range for these anti-inflammatory effects is typically in the low micromolar range (1-50 uM). Further quantitative in vitro potency data (EC₅0 or IC₅0 values) are limited.
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| ln Vivo |
In vivo studies of (5alpha)-stigmastane-3,6-dione have primarily focused on its anti-inflammatory activity. In rodent models of acute inflammation, such as carrageenan-induced paw edema, administration of the compound (typically intraperitoneally or orally at doses of 5-25 mg/kg) leads to a significant reduction in paw swelling compared to vehicle controls. The anti-inflammatory effect is comparable to standard non-steroidal anti-inflammatory drugs in some studies. Additionally, the compound has shown efficacy in chronic inflammatory models such as adjuvant-induced arthritis, where it reduces joint swelling and inflammatory markers. Antimicrobial efficacy in animal infection models has not been extensively reported. The antifeedant activity has been demonstrated in insect bioassays using boll weevils, where (5alpha)-stigmastane-3,6-dione reduces feeding when incorporated into artificial diet at concentrations of 50-200 ppm.
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| Enzyme Assay |
A typical non-cellular binding assay for (5alpha)-stigmastane-3,6-dione involves testing its ability to inhibit COX-1 and COX-2 enzymes using commercially available fluorometric or colorimetric assay kits. The reaction mixture contains 50 uL of enzyme solution (recombinant human COX-1 or COX-2, 0.1 U/mL in assay buffer), 50 uL of test compound (0-50 uM), and 100 uL of arachidonic acid substrate (1.5 uM). The reaction is initiated by adding heme cofactor (1 uM), and the mixture is incubated at 37degC for 10 min. After incubation, the reaction is terminated by adding stop solution. The product (PGE2) is quantified by ELISA or by direct detection of oxygen consumption using a Clark-type oxygen electrode. Percentage inhibition is calculated relative to vehicle-treated controls. Alternatively, an NF-kappaB binding assay using a fluorescently labeled NF-kappaB oligonucleotide probe and recombinant p50 protein may be used to evaluate modulation of this transcription factor.
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| Cell Assay |
In vitro cell-based assays for (5alpha)-stigmastane-3,6-dione are typically conducted using mouse macrophage RAW 264.7 cells. Cells are cultured in DMEM supplemented with 10% FBS and 1% penicillin-streptomycin at 37degC in 5% CO2. Cells are seeded into 96-well plates at 2 × 10⁵ cells/well and allowed to adhere overnight. For anti-inflammatory studies, cells are pre-treated with (5alpha)-stigmastane-3,6-dione at concentrations of 1, 5, 10, 25, and 50 uM for 1 h, then stimulated with lipopolysaccharide (LPS, 1 ug/mL) for 24 h. After incubation, culture supernatants are collected for measurement of pro-inflammatory cytokines (TNF-alpha, IL-1beta, IL-6) and nitric oxide (NO) using commercial ELISA kits and the Griess reagent assay, respectively. Cell viability is assessed using the MTT assay (0.5 mg/mL, 4 h incubation) to ensure that observed effects are not due to cytotoxicity. Nuclear extracts can be prepared from treated cells to assess NF-kappaB activation by electrophoretic mobility shift assay (EMSA) or ELISA-based transcription factor assay.
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| Animal Protocol |
In vivo animal studies for (5alpha)-stigmastane-3,6-dione are typically performed using adult male Swiss albino mice or Wistar rats (6-8 weeks old, 20-30 g). For the carrageenan-induced paw edema model, mice are orally or intraperitoneally administered the test compound at doses of 5, 10, or 25 mg/kg suspended in 0.5% carboxymethyl cellulose (CMC) vehicle. Indomethacin (10 mg/kg) is used as a positive control. One hour after treatment, 50 uL of 1% carrageenan in saline is injected into the subplantar region of the right hind paw. Paw volume is measured using a plethysmometer at 0, 1, 2, 3, 4, and 6 h post-injection. Percent inhibition of edema is calculated as (Vcontrol - Vtreated) / Vcontrol × 100. At the end of the experiment, animals are euthanized, and paw tissues are collected for histological analysis and cytokine measurement. All studies must be approved by the institutional animal care and use committee.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of (5alpha)-stigmastane-3,6-dione have not been extensively characterized in the literature. As a sterol compound with a molecular weight of 428.69 g/mol and a highly lipophilic steroid core structure (multiple fused rings), the compound is expected to have very low aqueous solubility and potentially poor oral bioavailability without specialized formulation. Following absorption, (5alpha)-stigmastane-3,6-dione is predicted to have a large volume of distribution and extensive tissue binding due to its high lipophilicity. Metabolism likely occurs through phase I oxidative reactions (CYP450-mediated hydroxylation) and phase II conjugation (glucuronidation). The compound is likely eliminated primarily via biliary excretion. Tissue distribution, elimination half-life, and specific metabolic pathways have not been experimentally determined. Experimental studies would be required to fully characterize its pharmacokinetic profile. For research use only.
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| Toxicity/Toxicokinetics |
Toxicological information for (5alpha)-stigmastane-3,6-dione is limited. Given its natural origin as a plant sterol isolated from Ailanthus altissima and Alchornea floribunda, the compound is unlikely to be highly toxic, as many plant-derived sterols are generally considered low-risk. No acute or subchronic toxicity data have been reported in peer-reviewed literature. The compound has not been evaluated in standard genotoxicity assays such as the Ames test or micronucleus assay. No reproductive or developmental toxicity studies are available. In vitro cytotoxicity studies using mammalian cell lines (such as RAW 264.7 macrophages) suggest that (5alpha)-stigmastane-3,6-dione is not cytotoxic at concentrations up to 50 uM, but higher concentrations or longer exposure periods may require further evaluation. Standard laboratory safety precautions (gloves, lab coat, eye protection) should be used when handling this compound. For research use only; not intended for human consumption.
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| References | |
| Additional Infomation |
It has been reported that metasequoia and black pepper contain stigmasterane-3,6-dione, and there is relevant data available.
Toxicological information for (5alpha)-stigmastane-3,6-dione is limited. Given its natural origin as a plant sterol isolated from Ailanthus altissima and Alchornea floribunda, the compound is unlikely to be highly toxic, as many plant-derived sterols are generally considered low-risk. No acute or subchronic toxicity data have been reported in peer-reviewed literature. The compound has not been evaluated in standard genotoxicity assays such as the Ames test or micronucleus assay. No reproductive or developmental toxicity studies are available. In vitro cytotoxicity studies using mammalian cell lines (such as RAW 264.7 macrophages) suggest that (5alpha)-stigmastane-3,6-dione is not cytotoxic at concentrations up to 50 uM, but higher concentrations or longer exposure periods may require further evaluation. Standard laboratory safety precautions (gloves, lab coat, eye protection) should be used when handling this compound. For research use only; not intended for human consumption. |
| Molecular Formula |
C29H48O2
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| Molecular Weight |
428.69
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| Exact Mass |
428.365
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| CAS # |
22149-69-5
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| PubChem CID |
543599
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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 |
519.5±33.0 °C at 760 mmHg
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| Melting Point |
195 - 198 °C
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| Flash Point |
191.5±22.4 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
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| Index of Refraction |
1.501
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| LogP |
8.37
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
31
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| Complexity |
695
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC(=O)[C@@H]4[C@@]3(CCC(=O)C4)C)C)C(C)C
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| InChi Key |
HMMVBUVVQLUGQA-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C29H48O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h18-20,22-26H,7-17H2,1-6H3
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| Chemical Name |
17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
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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 | 2.3327 mL | 11.6634 mL | 23.3269 mL | |
| 5 mM | 0.4665 mL | 2.3327 mL | 4.6654 mL | |
| 10 mM | 0.2333 mL | 1.1663 mL | 2.3327 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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