Art. -Nr.: HY-N2388

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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Reinheit: 99.97%
CAS. Nr.: 495-02-3
Formel: C₁₉H₂₂O₃
Molecular Weight:298.38

Speicherung:

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Auraptene Chemical Structure

CAS. Nr.: 495-02-3

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target^[1]

MMP-2

Alle MMP Isoform-spezifische Produkte anzeigen :

Alle PPAR Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
3T3-L1	IC₅₀	47 μM Compound: 8, Auraptene	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	[PMID: 19054677]
A549	IC₅₀	82 μM Compound: 1	Cytotoxicity against human A549 cells after 72 hrs by MTT assay Cytotoxicity against human A549 cells after 72 hrs by MTT assay	[PMID: 21696954]
BT-549	IC₅₀	24 μM Compound: 7	Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay	[PMID: 29144746]
HT-29	IC₅₀	>500 μM Compound: 8, Auraptene	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	[PMID: 19054677]
Jurkat	IC₅₀	55.36 μg/mL Compound: Auraptene	Cytotoxicity against human Jurkat T cells after 36 hrs by MTT assay Cytotoxicity against human Jurkat T cells after 36 hrs by MTT assay	[PMID: 21546250]
LoVo	IC₅₀	66 μM Compound: 1	Cytotoxicity against human LoVo cells after 72 hrs by MTT assay Cytotoxicity against human LoVo cells after 72 hrs by MTT assay	[PMID: 21696954]
MDA-MB-231	IC₅₀	80 μM Compound: 7	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	[PMID: 29144746]
MDCK	CC₅₀	7 μM Compound: 13a	Cytotoxicity against MDCK cells after 48 hrs by MTT assay Cytotoxicity against MDCK cells after 48 hrs by MTT assay	[PMID: 28501512]
PC-3	IC₅₀	65 μM Compound: 1	Cytotoxicity against human PC3 cells after 72 hrs by MTT assay Cytotoxicity against human PC3 cells after 72 hrs by MTT assay	[PMID: 21696954]
SK-MEL-28	IC₅₀	87 μM Compound: 1	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	[PMID: 21696954]
T47D	IC₅₀	10.2 μM Compound: 8, AUR	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	[PMID: 23434131]
T47D	IC₅₀	18.8 μM Compound: 8, AUR	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	[PMID: 23434131]
U-373MG ATCC	IC₅₀	82 μM Compound: 1	Cytotoxicity against human U373 cells after 72 hrs by MTT assay Cytotoxicity against human U373 cells after 72 hrs by MTT assay	[PMID: 21696954]

In Vitro

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.

Cell Viability Assay^[1].

Cell Line:

Oral epithelial cell line GMSM-K
Concentration:

0-20 μM
Incubation Time:

2 h
Result:

Didn't affect the survival rate of epithelial cells.

Real Time qPCR^[2].

Cell Line:

MCF-7 cell
Concentration:

10 μM
Incubation Time:

24 h
Result:

Upregulated gene expression levels of CDKN2B (Cyclin dependent kinase inhibitor 2B), DDIT3 (DNA damage inducible transcript 3), and JUN (JUN oncogene).

Real Time qPCR^[6].

Cell Line:

HCoV-OC43-infected human lung fibroblast MRC-5 cells
Concentration:

10 μM
Incubation Time:

4 days
Result:

Decreased viral RNA levels in HCoV-OC43-infected cells.

In Vivo

Auraptene (200, 500 ppm, mixed in the diet, p.o.) delays the tumor progression of breast cancer rats by inhibiting cyclin D1 protein^[3].
Auraptene (100, 500 ppm, mixed in the diet, p.o.) alleviates gastritis by reducing Helicobacter pylori colonization and pro-inflammatory mediator production in C57BL/6 mice^[4].
Auraptene (5, 50 mg/kg, 6 weeks, p.o.) prevents heart failure caused by myocardial infarction by activating peroxisome proliferator activated receptor alpha (PPAR alpha) in rats ^[5].
Auraptene (2, 4, 8, 16 mg/kg, 5 weeks, p.o.) exhibits anti hypertensive effects in hypertensive rats by reducing mean systolic blood pressure^[8].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Mammary carcinogenesis model in female Sprague Dawley rats^[3].
Dosage:

200, 500 ppm
Administration:

Oral gavage (p.o.); mixed in the diet
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.

Animal Model:

Female C57BL/6 mice^[4].
Dosage:

100, 500 ppm
Administration:

Oral gavage (p.o.); mixed in the diet
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.

Animal Model:

Sprague–Dawley rats with moderate myocardial infarction^[5].
Dosage:

5, 50 mg/kg
Administration:

Oral gavage (p.o.); 6 weeks
Result:

Suppresses PE-induced hypertrophic responses in cardiomyocytes. Prevented the development of cardiac hypertrophy and fibrosis in rats with myocardial infarction.

Animal Model:

Desoxycorticosterone acetate (DOCA) salt induced hypertensive rats^[8].
Dosage:

2, 4, 8, 16 mg/kg
Administration:

Oral gavage (p.o.); 5 weeks
Result:

Reduced the mean systolic blood pressure (MSBP) in DOCA salt treated rats.

Chemical Information

CAS. Nr. 495-02-3
Appearance Solid
Molecular Weight 298.38
Formel C₁₉H₂₂O₃
Color Off-white to light yellow
SMILES

O=C1C=CC2=CC=C(OC/C=C(C)/CC/C=C(C)/C)C=C2O1
Structure Classification
- Phenylpropanoids
- Coumarins
Initial Source
- Plants
- other families
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Lösungsmittel & Löslichkeit

In Vitro:

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)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.3514 mL

16.7572 mL

33.5143 mL

5 mM

0.6703 mL

3.3514 mL

6.7029 mL

10 mM

0.3351 mL

1.6757 mL

3.3514 mL

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.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

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.

Protocol 1

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.

Protocol 2

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.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.08 mg/mL (6.97 mM); Clear solution

This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
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

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (277 KB)
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)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[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]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

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

Keywords

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Auraptene

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Cell Cycle/DNA Damage Compound Library

Immunology/Inflammation Compound Library

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Natural Product Library

Anti-Cancer Compound Library

Anti-Aging Compound Library

Alle MMP Isoform-spezifische Produkte anzeigen

Alle PPAR Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Auraptene Related Classifications

HY-N2388 Related Classifications