AURAPTENE

AURAPTENE Property

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.

LogP

5.690 (est)

Safety

WGK Germany 

3

HS Code 

2932990090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

AURAPTENE Chemical Properties,Usage,Production

Description

Auraptene (495-02-3) is a bioactive terpenoid occurring in a variety of citrus fruits and possessing therapeutic potential.1?? Displays neuritogenic activity2?and 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.4?Displays hepatoprotective5?and 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ChEBI: Auraptene is a member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group.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

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

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.