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| Targets |
ar-Turmerone induces apoptosis in U937 human lymphoma cells through upregulation of pro-apoptotic proteins Bax and p53, leading to mitochondrial cytochrome c release and subsequent activation of caspase-3.
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| ln Vitro |
ar-Turmerone treatment inhibited the viability of U937 human lymphoma cells in a concentration-dependent manner. After 48 hours of treatment, viability was inhibited by 61%, 68%, 81%, and 84% at concentrations of 40, 80, 120, and 160 μg/mL, respectively.
ar-Turmerone induced nucleosomal DNA fragmentation and increased the percentage of sub-diploid cells in U937 cells, both characteristic of apoptosis. Western blot and RT-PCR analysis showed that ar-Turmerone treatment concentration-dependently increased the expression levels of the pro-apoptotic proteins Bax and p53 at both mRNA and protein levels. The expression levels of anti-apoptotic Bcl-2 and p21 were not changed. ar-Turmerone treatment induced the release of mitochondrial cytochrome c into the cytosol. Caspase-3 activity was increased in a concentration-dependent manner after ar-Turmerone treatment, with fold increases of 1.4, 2.6, and 3.0 at concentrations of 40, 80, and 120 μg/mL, respectively, compared to control. |
| ln Vivo |
Intraperitoneal administration of turmeric oil (containing ar-Turmerone) at doses of 10, 50, and 250 mg/kg body weight for 5 days inhibited phorbol-12-myristate-13-acetate (PMA)-induced superoxide radical generation in peritoneal macrophages of mice. Percentage inhibition was 14.17%, 18.25%, and 22.86% at 10, 50, and 250 mg/kg, respectively.
Oral administration of turmeric oil at 100 and 500 mg/kg body weight for 30 days significantly increased antioxidant enzyme levels in blood and liver of mice. In blood, increases were observed in catalase, superoxide dismutase (SOD), glutathione reductase, and glutathione levels. In liver, increases were observed in SOD, glutathione peroxidase, and glutathione-S-transferase (GST) activities. In carrageenan-induced acute paw edema model, intraperitoneal administration of turmeric oil at 100, 500, and 1000 mg/kg body weight for 5 days produced inhibition of edema by 33.3%, 50%, and 61.1% respectively at the 3rd hour. In dextran-induced acute paw edema model, intraperitoneal administration of turmeric oil at 100, 500, and 1000 mg/kg body weight for 5 days reduced paw edema by 35.3%, 47.1%, and 58.8% respectively at the 3rd hour. In formalin-induced chronic paw edema model, intraperitoneal administration of turmeric oil at 100, 500, and 1000 mg/kg body weight for 5 days inhibited paw edema by 34.17%, 41.67%, and 50% respectively. In the acetic acid-induced writhing test for antinociceptive activity, intraperitoneal administration of turmeric oil at 100, 500, and 1000 mg/kg body weight produced inhibition of writhing by 40.41%, 57.56%, and 69.48% respectively. |
| Enzyme Assay |
Acid Phosphatase (ACP) Activity Assay: The activity of ACP in BMDC lysosomes was measured as an indicator of cellular maturity. After treating BMDCs with ar-Turmerone (25 μg/ml) or control substances for 48 hours, ACP activity was quantified using a testing kit based on the phenol-4-aminoantipyrine (4-AAP) method. The absorbance was measured at OD520 nm, and activity was expressed in units per gram of protein.
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| Cell Assay |
Cell viability was assessed using the MTT assay. U937 cells were seeded in 24-well plates and treated with ar-Turmerone (dissolved in DMSO) at concentrations ranging from 0 to 160 μg/mL for 24 or 48 hours. MTT solution was added, incubated, and the formazan product was dissolved and measured at 540 nm.
DNA fragmentation was assessed by agarose gel electrophoresis. After treatment, cells were lysed, DNA was isolated by phenol-chloroform extraction, treated with RNase A, and electrophoresed on a 1.5% agarose gel. Fragmented DNA was visualized under UV light after ethidium bromide staining. Quantitative analysis of fragmented DNA was performed using a radiolabeled thymidine incorporation method. Cells pre-labeled with ³H-thymidine were treated, lysed, and centrifuged to separate low and high molecular weight DNA. Radioactivity in each fraction was measured by scintillation counting to calculate the percentage of fragmented DNA. mRNA expression levels of Bax, Bcl-2, p53, and p21 were analyzed by RT-PCR. Total RNA was isolated, reverse transcribed into cDNA, and amplified using gene-specific primers. PCR products were separated by agarose gel electrophoresis and visualized. Protein expression levels were analyzed by Western blot. Cell lysates were prepared, proteins were separated by SDS-PAGE, transferred to membranes, and probed with specific antibodies against Bax, Bcl-2, p53, p21, caspase-3, and cytochrome c. Caspase-3 activity was measured using a fluorescence-based assay kit. Cell lysates were prepared, and caspase-3 activity was determined by measuring the fluorescence of the cleaved substrate. Flow cytometry was used to analyze the cell cycle and sub-diploid (apoptotic) cell population. Cells were stained with propidium iodide, and DNA content was analyzed. |
| Animal Protocol |
For in vivo antioxidant studies (PMA-induced superoxide generation), female Balb/C mice were treated intraperitoneally with different concentrations (10, 50, 250 mg/kg body weight) of turmeric oil for 5 days. On the fifth day, peritoneal macrophages were elicited by sodium caseinate and activated by PMA injection. Macrophages were harvested after 3 hours for superoxide measurement.
For long-term antioxidant enzyme level assessment, female Balb/C mice were divided into groups and treated orally with turmeric oil dissolved in paraffin oil at doses of 100 or 500 mg/kg body weight daily for 30 days. Control groups received paraffin oil only. At the end, blood and liver tissues were collected for enzyme analysis. For acute anti-inflammatory models (carrageenan and dextran), female Balb/C mice were divided into groups. Groups received intraperitoneal injections of turmeric oil at 100, 500, or 1000 mg/kg body weight, or diclofenac (10 mg/kg) as standard, for 5 consecutive days. One hour after the last dose, acute inflammation was induced by subplantar injection of carrageenan or dextran. Paw thickness was measured periodically. For chronic anti-inflammatory model (formalin), female Balb/C mice received intraperitoneal injections of turmeric oil (100, 500, 1000 mg/kg) or diclofenac (10 mg/kg) for 5 days. On the fifth day, chronic inflammation was induced by subplantar injection of formalin. Paw thickness was measured for 6 consecutive days. For antinociceptive activity (acetic acid-induced writhing), male Balb/C mice were divided into groups. Groups received intraperitoneal injections of turmeric oil (100, 500, 1000 mg/kg) or aspirin (100 mg/kg) as standard. After 30 minutes, acetic acid was administered intraperitoneally, and the number of writhing movements was counted. |
| Toxicity/Toxicokinetics |
Ar-curcumin (3.125-100 μg/ml) did not significantly inhibit the proliferation of normal human skin fibroblasts (Hs-68), indicating that it did not have selective cytotoxicity to this normal cell line at the tested concentrations.
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| References |
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| Additional Infomation |
(+)-(S)-ar-curcumin is a sesquiterpene compound with the structure 2-methylhept-2-en-4-one, substituted with 4-methylphenyl at the 6-position. It has been isolated from the Ranunculaceae plant Peltophorum dasyrachis. It is an EC 3.1.1.7 (acetylcholinesterase) inhibitor and a plant metabolite. It is a sesquiterpene and enone compound. Curcumin has been reported in Curcuma xanthorrhiza, Akebia trifoliata, and other organisms with relevant data. Curcumin is the main sesquiterpene component of the volatile oil of Curcuma longa L. Studies have shown that the antiproliferative effect of curcumin on U937 cells is mediated by inducing apoptosis via the mitochondrial pathway, which involves Bax upregulation, cytochrome c release, and caspase-3 activation, independent of changes in Bcl-2 and p21. This suggests that curcumin may be a potential anticancer drug targeting the apoptosis pathway.
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| Molecular Formula |
C15H20O
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| Molecular Weight |
216.3187
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| Exact Mass |
216.151
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| CAS # |
532-65-0
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| Related CAS # |
ar-Turmerone-d3
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| PubChem CID |
160512
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| Appearance |
Colorless to light yellow liquid
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| Boiling Point |
326℃
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| LogP |
4.023
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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 |
4
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| Heavy Atom Count |
16
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| Complexity |
253
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC(=CC(=O)C[C@H](C)C1=CC=C(C)C=C1)C
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| InChi Key |
NAAJVHHFAXWBOK-ZDUSSCGKSA-N
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| InChi Code |
InChI=1S/C15H20O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5-9,13H,10H2,1-4H3/t13-/m0/s1
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| Chemical Name |
(6S)-2-methyl-6-(4-methylphenyl)hept-2-en-4-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 |
| 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 | 4.6228 mL | 23.1139 mL | 46.2278 mL | |
| 5 mM | 0.9246 mL | 4.6228 mL | 9.2456 mL | |
| 10 mM | 0.4623 mL | 2.3114 mL | 4.6228 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT03254680 | WITHDRAWN | Dietary Supplement: Turmeric | Dravet Syndrome Epilepsy Focal Seizures Lennox-Gastaut Syndrome Tuberous Sclerosis |
NYU Langone Health | 2018-03 | Not Applicable |
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