| Targets |
Peroxisome Proliferator-Activated Receptor Alpha (PPARα): (+)-Dehydrovomifoliol, one enantiomer of the racemic mixture, regulates lipid metabolism by activating PPARα.
Acetylcholinesterase (AChE): Dehydrovomifoliol exhibits moderate acetylcholinesterase inhibitory activities. E2F1/AKT/mTOR Signaling Pathway: An alternative mechanism suggests that the anti-NAFLD activity of dehydrovomifoliol may involve this signaling axis. |
|---|---|
| ln Vitro |
Cytotoxic Activity: Dehydrovomifoliol shows significant cytotoxic activities against three human cancer cell lines, with IC₅₀ values ranging from 3.7-8.1 μM, including HONE-1 nasopharyngeal carcinoma cells, KB oral epidermoid carcinoma cells, and HT29 colorectal carcinoma cells. However, it should be noted that (±)-Dehydrovomifoliol itself shows no significant cytotoxic activity against various human cancer cell lines. One study demonstrated that this compound (1 nM-100 μM, 48 h) has no significant cytotoxicity against MCF-7, H460, HT-29, or CEM human cancer cell lines.
Anti-angiogenic Activity: (±)-Dehydrovomifoliol shows no significant anti-angiogenic activity in the Matrigel endothelial cell tube formation assay, with an IC₅₀ value greater than 10 μM (1 nM-10 μM, 24 h).
Lipid Metabolism Regulation: In hepatic cells, (+)-dehydrovomifoliol activates the PPARα signaling pathway, leading to increased expression of Fibroblast Growth Factor 21 (FGF21). Elevated FGF21 levels inhibit the expression of SREBP1, a master transcriptional regulator of lipogenesis, thereby reducing fatty acid and triglyceride synthesis and alleviating hepatic lipid accumulation. An alternative mechanism suggests that the anti-NAFLD activity of dehydrovomifoliol may involve the E2F1/AKT/mTOR signaling axis.
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| ln Vivo |
Based on its in vitro mechanism of action, (±)-Dehydrovomifoliol may regulate hepatic lipid metabolism via the PPARα–FGF21 signaling pathway in animal experiments, thereby exerting anti-NAFLD effects. Its specific antitumor activity in vivo and other pharmacodynamic data still require further investigation.
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| Enzyme Assay |
For assessing PPARα activation activity, a cell-free system using purified PPARα protein and a luciferase reporter system can be employed. Fluorescence signals are measured to evaluate the compound's activation of PPARα, with known PPARα agonists serving as positive controls.
|
| Cell Assay |
Cytotoxicity Assay: MCF-7, H460, HT-29, or CEM human cancer cell lines are seeded in appropriate culture plates and treated with various concentrations of (±)-Dehydrovomifoliol (1 nM-100 μM) for 48 hours. Cell viability is assessed by MTT or CCK-8 assays to calculate IC₅₀ values for cytotoxicity evaluation.
Anti-angiogenic Assay: In the Matrigel endothelial cell tube formation assay, human umbilical vein endothelial cells are seeded on Matrigel-coated plates and treated with (±)-Dehydrovomifoliol (1 nM-10 μM) for 24 hours. Tube formation is observed and quantified under a microscope, with known anti-angiogenic inhibitors serving as positive controls.
Lipid Metabolism Study: In hepatic cell lines such as HepG2, cells are treated with (+)-dehydrovomifoliol. mRNA expression levels of PPARα, FGF21, SREBP1, and other genes are detected by qPCR, protein expression changes are assessed by Western blot, and intracellular lipid accumulation is evaluated by Oil Red O staining.
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| References | |
| Additional Infomation |
Dehydrovomifoliol is a fenane monoterpene with methyl groups at positions 3, 5, and 5, and a hydroxyl group and a 3-oxobut-1-en-1-yl group at position 4. It is a fenane monoterpene and also an enone.
|
| Exact Mass |
222.126
|
|---|---|
| CAS # |
15764-81-5
|
| Related CAS # |
Dehydrovomifoliol;39763-33-2
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| PubChem CID |
5280662
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.125g/cm3
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| Boiling Point |
367.4ºC at 760mmHg
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| Flash Point |
190.2ºC
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| Vapour Pressure |
6.84E-07mmHg at 25°C
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| Index of Refraction |
1.554
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| LogP |
1.808
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
|
| Heavy Atom Count |
16
|
| Complexity |
388
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| Defined Atom Stereocenter Count |
0
|
| InChi Key |
JJRYPZMXNLLZFH-AATRIKPKSA-N
|
| InChi Code |
InChI=1S/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+
|
| Chemical Name |
4-hydroxy-3,5,5-trimethyl-4-[(E)-3-oxobut-1-enyl]cyclohex-2-en-1-one
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| Synonyms |
Dehydrovomifoliol; (4S)-4-hydroxy-3,5,5-trimethyl-4-[(E)-3-oxobut-1-enyl]cyclohex-2-en-1-one; CHEBI:18429; (4S)-4-hydroxy-3,5,5-trimethyl-4-((E)-3-oxobut-1-enyl)cyclohex-2-en-1-one; ...; 15764-81-5;
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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 |
| 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.) |
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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