ChemicalBook Product Catalog Natural Products Coumarin AURAPTENE

AURAPTENE

Product NameAURAPTENE
CAS495-02-3
MFC19H22O3
MW298.38
EINECS
MOL File495-02-3.mol

Chemical Properties

Melting point	91 °C
Boiling point	455.5±45.0 °C(Predicted)
Density	1.079±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Store in freezer, under -20°C
solubility	DMSO: >20mg/mL
form	powder
color	white to off-white
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChI	1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+
InChIKey	RSDDHGSKLOSQFK-RVDMUPIBSA-N
SMILES	C\C(C)=C\CC\C(C)=C\COc1ccc2C=CC(=O)Oc2c1
LogP	5.690 (est)

Safety Information

WGK Germany	3
HS Code	2932990090
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Auraptene (495-02-3) is a bioactive terpenoid occurring in a variety of citrus fruits and possessing therapeutic potential.1 Displays neuritogenic activity2and neuroprotective effects via suppression of inflammation and induction of GDNF and BDNF in neuronal cells3. Attenuates ROS production and enhances mitochondrial respiration which mitigates Parkinson’s disease-like behavior.4Displays hepatoprotective5and chemopreventive activity6.

Chemical Properties

Soluble in methanol, ethanol, DMSO and other organic solvents, derived from the unripe or nearly ripe dried outer pericarp of Hualizhou pomelo or pomelo of the Brassicaceae family; Citrus red.

Uses

antineoplastic, apoptosis inducer

Uses

Auraptene is a natural bioactive monoterpene coumarin ether. Auraptene has shown a remarkable effect in the prevention of degenerative diseases.

Definition

ChEBI: Auraptene is a member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties. It has a role as a plant metabolite, an antineoplastic agent, an apoptosis inducer, a dopaminergic agent, a neuroprotective agent, an antihypertensive agent, a gamma-secretase modulator, a vulnerary, an EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor, a PPARalpha agonist, a gastrointestinal drug, a matrix metalloproteinase inhibitor, an antioxidant and a hepatoprotective agent. It is a member of coumarins and a monoterpenoid. It is functionally related to an umbelliferone.

Synthesis

93-35-6

6138-90-5

495-02-3

Synthesis procedure for Aurapten (5): propylene oxide (159 μL, 0.80 mmol) was added to a stirred mixture of 7-hydroxycoumarin (100 mg, 0.62 mmol) and anhydrous potassium carbonate (171 mg, 1.24 mmol) in anhydrous N,N-dimethylformamide (5 mL) under argon protection. The reaction mixture was stirred under reflux conditions for 3 hours. After completion of the reaction, the reaction mixture was neutralized with 1 M aqueous hydrochloric acid. The brown residue obtained was dissolved in dichloromethane (20 mL), washed sequentially with water (2 x 20 mL), saturated saline (30 mL) and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a brown oil, which was purified by fast column chromatography using diethyl ether-hexane (1:1) as eluent to give a white powdery product 5 (181 mg, 76% yield). The structure of the product was confirmed by 1H NMR, 13C NMR and high resolution fast atom bombardment mass spectrometry (HR-FABMS).

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].

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.

IC 50

MMP-2

References

[1] BAHRAM BIBAK. A review of the pharmacological and therapeutic effects of auraptene[J]. BioFactors, 2019, 45 6: 867-879. DOI:10.1002/biof.1550
[2] YOSHIKO FURUKAWA. Neurotrophic effect of citrus auraptene: neuritogenic activity in PC12 cells.[J]. International Journal of Molecular Sciences, 2012, 13 5: 5338-5347. DOI:10.3390/ijms13055338
[3] YOSHIKO FURUKAWA. Citrus Auraptene Induces Expression of Brain-Derived Neurotrophic Factor in Neuro2a Cells.[J]. Molecules, 2020. DOI:10.3390/molecules25051117
[4] YUNSEON JANG. Auraptene Mitigates Parkinson’s Disease-Like Behavior by Protecting Inhibition of Mitochondrial Respiration and Scavenging Reactive Oxygen Species[J]. International Journal of Molecular Sciences, 2019. DOI:10.3390/ijms20143409
[5] WANG J, FU T, DONG R, et al. Hepatoprotection of auraptene from the peels of citrus fruits against 17α-ethinylestradiol-induced cholestasis in mice by activating farnesoid X receptor[J]. Food & Function, 2019, 7: 3839-3850. DOI:10.1039/c9fo00318e
[6] T TANAKA. Citrus auraptene exerts dose-dependent chemopreventive activity in rat large bowel tumorigenesis: the inhibition correlates with suppression of cell proliferation and lipid peroxidation and with induction of phase II drug-metabolizing enzymes.[J]. Cancer research, 1998, 58 12: 2550-2556.

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