Auraptene
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Auraptene is an orally active geranyloxycoumarin that can be isolated from plants in the Brassicaceae family, antibacterial, anti-pathogen, antioxidant, anti-tumor, and neuroprotective effects. Auraptene plays an important role in the treatment of various chronic diseases such as hypertension and cystic fibrosis.
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- Pureté: 99.97%
- CAS No.: 495-02-3
- Formule: C19H22O3
- Masse moléculaire:298.38
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Stockage:
4°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Activité biologique
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Chemical Information
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Solvant et solubilité
- Pureté et documentation
- Références
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Help & FAQs
Activité biologique
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MMP-2 |
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Cell Line
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Type | Value | Description | References |
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| 3T3-L1 | IC50 |
47 μM
Compound: 8, Auraptene
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Anticorpulence activity against mouse 3T3L1 cells assessed as inhibition of lipid droplet accumulation
Anticorpulence activity against mouse 3T3L1 cells assessed as inhibition of lipid droplet accumulation
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[PMID: 19054677] |
| A549 | IC50 |
82 μM
Compound: 1
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Cytotoxicity against human A549 cells after 72 hrs by MTT assay
Cytotoxicity against human A549 cells after 72 hrs by MTT assay
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[PMID: 21696954] |
| BT-549 | IC50 |
24 μM
Compound: 7
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Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay
Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay
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[PMID: 29144746] |
| HT-29 | IC50 |
>500 μM
Compound: 8, Auraptene
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Anticancer activity against human HT-29 cells after 72 hrs by MTT assay
Anticancer activity against human HT-29 cells after 72 hrs by MTT assay
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[PMID: 19054677] |
| Jurkat | IC50 |
55.36 μg/mL
Compound: Auraptene
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Cytotoxicity against human Jurkat T cells after 36 hrs by MTT assay
Cytotoxicity against human Jurkat T cells after 36 hrs by MTT assay
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[PMID: 21546250] |
| LoVo | IC50 |
66 μM
Compound: 1
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Cytotoxicity against human LoVo cells after 72 hrs by MTT assay
Cytotoxicity against human LoVo cells after 72 hrs by MTT assay
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[PMID: 21696954] |
| MDA-MB-231 | IC50 |
80 μM
Compound: 7
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Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT assay
Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT assay
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[PMID: 29144746] |
| MDCK | CC50 |
7 μM
Compound: 13a
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Cytotoxicity against MDCK cells after 48 hrs by MTT assay
Cytotoxicity against MDCK cells after 48 hrs by MTT assay
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[PMID: 28501512] |
| PC-3 | IC50 |
65 μM
Compound: 1
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Cytotoxicity against human PC3 cells after 72 hrs by MTT assay
Cytotoxicity against human PC3 cells after 72 hrs by MTT assay
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[PMID: 21696954] |
| SK-MEL-28 | IC50 |
87 μM
Compound: 1
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Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTT assay
Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTT assay
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[PMID: 21696954] |
| T47D | IC50 |
10.2 μM
Compound: 8, AUR
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Inhibition of mitochondrial ETC complex 1 in human T47D cells assessed as inhibition of 1% O2-induced HIF1 activation incubated for 30 mins prior to 1% O2-challenge measured after 16 hrs by luciferase reporter assay
Inhibition of mitochondrial ETC complex 1 in human T47D cells assessed as inhibition of 1% O2-induced HIF1 activation incubated for 30 mins prior to 1% O2-challenge measured after 16 hrs by luciferase reporter assay
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[PMID: 23434131] |
| T47D | IC50 |
18.8 μM
Compound: 8, AUR
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Inhibition of mitochondrial ETC complex 1 in human T47D cells assessed as inhibition of 1,10-phenanthroline-induced HIF1 activation incubated for 30 mins prior to 1,10-phenanthroline-challenge measured after 16 hrs by luciferase reporter assay
Inhibition of mitochondrial ETC complex 1 in human T47D cells assessed as inhibition of 1,10-phenanthroline-induced HIF1 activation incubated for 30 mins prior to 1,10-phenanthroline-challenge measured after 16 hrs by luciferase reporter assay
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[PMID: 23434131] |
| U-373MG ATCC | IC50 |
82 μM
Compound: 1
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Cytotoxicity against human U373 cells after 72 hrs by MTT assay
Cytotoxicity against human U373 cells after 72 hrs by MTT assay
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[PMID: 21696954] |
Auraptene (0-20 μM, 2 h) reduces the secretion of inflammatory mediators stimulated by lipopolysaccharides in oral epithelial cells and promotes wound healing by promoting cell migration[1]. Auraptene (10 μM, 24 h) inhibits the cell cycle progression of human breast cancer cell line MCF-7 by reducing the expression of cyclin D1 protein and inhibiting IGF-1[2]. Auraptene (10 μM, 4 days) exhibits antiviral activity against human coronavirus OC43 in MRC-5 cells[6]. Auraptene (25-400 μM) protects red blood cells from free radical induced damage by preventing the consumption of intracellular antioxidant GSH and inhibiting protein peroxidation[7].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:Oral epithelial cell line GMSM-K
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Concentration:0-20 μM
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Incubation Time:2 h
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Result:Didn't affect the survival rate of epithelial cells.
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Cell Line:MCF-7 cell
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Concentration:10 μM
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Incubation Time:24 h
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Result:Upregulated gene expression levels of CDKN2B (Cyclin dependent kinase inhibitor 2B), DDIT3 (DNA damage inducible transcript 3), and JUN (JUN oncogene).
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Cell Line:HCoV-OC43-infected human lung fibroblast MRC-5 cells
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Concentration:10 μM
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Incubation Time:4 days
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Result:Decreased viral RNA levels in HCoV-OC43-infected cells.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Mammary carcinogenesis model in female Sprague Dawley rats[3].
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Dosage:200, 500 ppm
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Administration:Oral gavage (p.o.); mixed in the diet
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Result:Delayed median time to tumor by 39 days and reduced Insulin like Growth Factor-1 (IGF-1, 10 ng/mL)-induced cyclin D1 expression by 40% in MCF-7 cells.
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Animal Model:Female C57BL/6 mice[4].
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Dosage:100, 500 ppm
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Administration:Oral gavage (p.o.); mixed in the diet
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Result:Inhibited H. pylori–induced expression and/or production of CD74, macrophage migration inhibitory factor, interleukin-1b, and tumor necrosis factor-a in gastric mucosa, together with serum macrophage inhibitory protein-2.
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Animal Model:Sprague–Dawley rats with moderate myocardial infarction[5].
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Dosage:5, 50 mg/kg
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Administration:Oral gavage (p.o.); 6 weeks
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Result:Suppresses PE-induced hypertrophic responses in cardiomyocytes. Prevented the development of cardiac hypertrophy and fibrosis in rats with myocardial infarction.
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Animal Model:Desoxycorticosterone acetate (DOCA) salt induced hypertensive rats[8].
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Dosage:2, 4, 8, 16 mg/kg
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Administration:Oral gavage (p.o.); 5 weeks
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Result:Reduced the mean systolic blood pressure (MSBP) in DOCA salt treated rats.
Chemical Information
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CAS No. 495-02-3
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Appearance Solid
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Masse moléculaire 298.38
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Formule C19H22O3
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Color Off-white to light yellow
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SMILES
O=C1C=CC2=CC=C(OC/C=C(C)/CC/C=C(C)/C)C=C2O1
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Structure Classification
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Initial Source
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
4°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
Solvant et solubilité
DMSO : 50 mg/mL (167.57 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.08 mg/mL (6.97 mM); Clear solution
This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.08 mg/mL (6.97 mM); Clear solution
This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Pureté et documentation
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Fiche technique (277 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Instruction de manipulation (2659 KB)
Références
[1]. La VD, et al. Anti-inflammatory and wound healing potential of citrus auraptene. J Med Food. 2013 Oct;16(10):961-4. [Content Brief]
[2]. Krishnan P, et al. Effects of Auraptene on IGF-1 Stimulated Cell Cycle Progression in the Human Breast Cancer Cell Line, MCF-7. Int J Breast Cancer. 2012;2012:502092. [Content Brief]
[3]. Krishnan P, et al. Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats. BMC Cancer. 2009 Jul 29;9:259. [Content Brief]
[4]. Sekiguchi H, et al. Auraptene attenuates gastritis via reduction of Helicobacter pylori colonization and pro-inflammatory mediator production in C57BL/6 mice. J Med Food. 2012 Jul;15(7):658-63. [Content Brief]
[5]. Sunagawa Y, et al. Auraptene, a citrus peel-derived natural product, prevents myocardial infarction-induced heart failure by activating PPARα in rats. Phytomedicine. 2022 Dec;107:154457. [Content Brief]
[6]. Min JS, et al. Auraptene Has Antiviral Activity against Human Coronavirus OC43 in MRC-5 Cells. Nutrients. 2023 Jun 29;15(13):2960. [Content Brief]
[7]. Jamialahmadi K, et al. Protective Effects of Auraptene against Free Radical-Induced Erythrocytes Damage. J Pharmacopuncture. 2022 Dec 31;25(4):344-353. [Content Brief]
[8]. Razavi BM, et al. Antihypertensive effect of auraptene, a monoterpene coumarin from the genus Citrus, upon chronic administration. Iran J Basic Med Sci. 2015 Feb;18(2):153-8. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 3.3514 mL | 16.7572 mL | 33.5143 mL | 83.7858 mL |
| 5 mM | 0.6703 mL | 3.3514 mL | 6.7029 mL | 16.7572 mL | |
| 10 mM | 0.3351 mL | 1.6757 mL | 3.3514 mL | 8.3786 mL | |
| 15 mM | 0.2234 mL | 1.1171 mL | 2.2343 mL | 5.5857 mL | |
| 20 mM | 0.1676 mL | 0.8379 mL | 1.6757 mL | 4.1893 mL | |
| 25 mM | 0.1341 mL | 0.6703 mL | 1.3406 mL | 3.3514 mL | |
| 30 mM | 0.1117 mL | 0.5586 mL | 1.1171 mL | 2.7929 mL | |
| 40 mM | 0.0838 mL | 0.4189 mL | 0.8379 mL | 2.0946 mL | |
| 50 mM | 0.0670 mL | 0.3351 mL | 0.6703 mL | 1.6757 mL | |
| 60 mM | 0.0559 mL | 0.2793 mL | 0.5586 mL | 1.3964 mL | |
| 80 mM | 0.0419 mL | 0.2095 mL | 0.4189 mL | 1.0473 mL | |
| 100 mM | 0.0335 mL | 0.1676 mL | 0.3351 mL | 0.8379 mL |
Auraptene Related Classifications
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