Scopolin

CAS# 531-44-2

Scopolin

Catalog No. BCN5701----Order now to get a substantial discount!

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Quality Control of Scopolin

Number of papers citing our products

Chemical structure

Scopolin

3D structure

Chemical Properties of Scopolin

Cas No. 531-44-2 SDF Download SDF
PubChem ID 439514 Appearance White powder
Formula C16H18O9 M.Wt 354.3
Type of Compound Coumarins Storage Desiccate at -20°C
Synonyms 7-Hydroxy 6-methoxycoumarin 7-glucoside; Scopoletin 7-glucoside; Scopoloside
Solubility Soluble in ethanol, methanol and water; practically insoluble in chloroform
Chemical Name 6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
SMILES COC1=C(C=C2C(=C1)C=CC(=O)O2)OC3C(C(C(C(O3)CO)O)O)O
Standard InChIKey SGTCGCCQZOUMJJ-YMILTQATSA-N
Standard InChI InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Scopolin

1 Hedera sp. 2 Hydrophyllum sp. 3 Mentzelia sp. 4 Scopolia sp. 5 Tanacetum sp.

Biological Activity of Scopolin

DescriptionScopolin exhibits significant and dose-related antinociceptive effects, it is a potential acetylcholinesterase (AChE) inhibitor. Scopolin can reduce the clinical symptoms of rat AIA by inhibiting inflammation and angiogenesis, it may be a potent agent for angiogenesis related diseases.Scopolin and related coumarins has fungitoxic effect on Sclerotinia sclerotiorum, which is a way to overcome sunflower head rot.
TargetsVEGFR | IL Receptor | AChR | Antifection
In vivo

Scopolin isolated from Erycibe obtusifolia Benth stems suppresses adjuvant-induced rat arthritis by inhibiting inflammation and angiogenesis.[Pubmed: 19327410]

Int Immunopharmacol. 2009 Jul;9(7-8):859-69.

Despite Scopolin is a main coumarin constituent in the stems of Erycibe obtusifolia Benth, a herb drug that has long been utilized in traditional Chinese medicine for the treatment of rheumatoid arthritis, little information is available about the pharmacological activities of this compound. The present study was performed to investigate the anti-rheumatic effects of Scopolin in adjuvant-induced arthritis (AIA) in rats, and explore the underlying mechanisms of action in views of anti-inflammatory and anti-angiogenic properties in the synovial tissues.
METHODS AND RESULTS:
Scopolin (50, 100 mg/kg), injected intraperitoneally for 10 days from the onset of secondary response, significantly inhibited both inoculated and non-inoculated paw swelling as well as articular index scores in AIA. Meanwhile, the mean body weight of rats treated with Scopolin was higher than that of model group. Rats treated with high dose of Scopolin (100 mg/kg) preserved a nearly normal histological architecture of the joints and showed a significant reduction of the new blood vessels in the synovial tissues. Additionally, Scopolin could reduce IL-6, VEGF and FGF-2 expressions in rat synovial tissues.
CONCLUSIONS:
In conclusion, Scopolin can reduce the clinical symptoms of rat AIA by inhibiting inflammation and angiogenesis, and this compound may be a potent agent for angiogenesis related diseases and can serve as a structural base for screening more potent synthetic analogs.

Fungitoxic effect of scopolin and related coumarins on Sclerotinia sclerotiorum. A way to overcome sunflower head rot.[Reference: WebLink]

Euphytica, 2006, 147(3):451-460.

The content of coumarins, as probable phytoalexins, was analysed in four sunflower genotypes that ranged in responses to head rot from highly susceptible to highly resistant.
METHODS AND RESULTS:
Low levels of all coumarins (Scopolin, scopoletin and ayapin) were detected in the three most susceptible genotypes irrespective of time after inoculation. However, in the resistant genotype there was a clear time-dependent disease-induced increase of all coumarins that reached a maximum after 10–14 days. Detailed comparison of the most susceptible and the resistant genotype showed that in the resistant but not the susceptible, scopoletin peroxidase activity increased during the course of the experiment. Results confirmed a clear negative correlation between coumarin content and disease symptoms and in particular for Scopolin. Furthermore we show for the first time that Scopolin is inhibitory to Sclerotinia at similar doses to scopoletin.
CONCLUSIONS:
As Scopolin is known to be less phytotoxic than ayapin and scopoletin, its accumulation may well confer head rot resistance with minimal plant damage and might be one of the bases for resistance to Sclerotinia.

Protocol of Scopolin

Kinase Assay

Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products.[Pubmed: 15566295]

J Med Chem. 2004 Dec 2;47(25):6248-54.

For the targeting selection of acetylcholinesterase (AChE) inhibitors from natural sources we generated a structure-based pharmacophore model utilizing an in silico filtering experiment for the discovery of promising candidates out of a 3D multiconformational database consisting of more than 110,000 natural products.
METHODS AND RESULTS:
In our study, scopoletin (1) and its glucoside Scopolin (2) emerged as potential AChE inhibitors by the virtual screening procedure. They were isolated by different chromatographic methods from the medicinal plant Scopolia carniolica Jaqc. and tested in an enzyme assay using Ellman's reagent. They showed moderate, but significant, dose-dependent and long-lasting inhibitory activities. In the in vivo experiments (icv application of 2 micromol) 1 and 2 increased the extracellular acetylcholine (ACh) concentration in rat brain to about 170% and 300% compared to basal release, respectively. At the same concentration, the positive control galanthamine increased the ACh concentration to about the same level as 1.
CONCLUSIONS:
These are the first in vivo results indicating an effect of coumarins on brain ACh.

Animal Research

Antinociceptive properties of coumarins, steroid and dihydrostyryl-2-pyrones from Polygala sabulosa (Polygalaceae) in mice.[Pubmed: 16393470 ]

J Pharm Pharmacol. 2006 Jan;58(1):107-12.

We have investigated the possible antinociceptive action of the extract, fractions and pure compounds obtained from the whole plant Polygala sabulosa A. W. Bennett (Polygalaceae) in acetic acid-induced visceral pain in mice.
METHODS AND RESULTS:
Intraperitoneal injection of animals with the hydroalcoholic extract and fractions (CH(2)Cl(2), EtOAc, n-BuOH, aqueous fraction) (1-100 mg kg(-1)) caused a dose-related and significant inhibition of the acetic acid-induced visceral nociceptive response. The CH(2)Cl(2), EtOAc and n-BuOH fractions were more potent than the hydroalcoholic extract and aqueous fraction. The isolated compounds dihydrostyryl-2-pyrones (1, 2, 3), styryl-2-pyrone (7), alpha-spinasterol (9), scopoletin (10) and two esters of the coumarin (scopoletin) obtained semisynthetically, acetylscopoletin (10a) and benzoylscopoletin (10b) (0.001-10 mg kg(-1)), exhibited significant and dose-related antinociceptive effects against acetic acid-induced visceral pain.
CONCLUSIONS:
The results distinguished, for the first time, the extract, fractions and pure compounds obtained from P. sabulosa that produced marked antinociception against the acetic acid-induced visceral nociceptive response, supporting the ethnomedical use of P. sabulosa.

Scopolin Dilution Calculator

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Scopolin Molarity Calculator

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Preparing Stock Solutions of Scopolin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8225 mL 14.1123 mL 28.2247 mL 56.4493 mL 70.5617 mL
5 mM 0.5645 mL 2.8225 mL 5.6449 mL 11.2899 mL 14.1123 mL
10 mM 0.2822 mL 1.4112 mL 2.8225 mL 5.6449 mL 7.0562 mL
50 mM 0.0564 mL 0.2822 mL 0.5645 mL 1.129 mL 1.4112 mL
100 mM 0.0282 mL 0.1411 mL 0.2822 mL 0.5645 mL 0.7056 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Scopolin

Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products.[Pubmed:15566295]

J Med Chem. 2004 Dec 2;47(25):6248-54.

For the targeting selection of acetylcholinesterase (AChE) inhibitors from natural sources we generated a structure-based pharmacophore model utilizing an in silico filtering experiment for the discovery of promising candidates out of a 3D multiconformational database consisting of more than 110,000 natural products. In our study, scopoletin (1) and its glucoside Scopolin (2) emerged as potential AChE inhibitors by the virtual screening procedure. They were isolated by different chromatographic methods from the medicinal plant Scopolia carniolica Jaqc. and tested in an enzyme assay using Ellman's reagent. They showed moderate, but significant, dose-dependent and long-lasting inhibitory activities. In the in vivo experiments (icv application of 2 micromol) 1 and 2 increased the extracellular acetylcholine (ACh) concentration in rat brain to about 170% and 300% compared to basal release, respectively. At the same concentration, the positive control galanthamine increased the ACh concentration to about the same level as 1. These are the first in vivo results indicating an effect of coumarins on brain ACh.

Scopolin isolated from Erycibe obtusifolia Benth stems suppresses adjuvant-induced rat arthritis by inhibiting inflammation and angiogenesis.[Pubmed:19327410]

Int Immunopharmacol. 2009 Jul;9(7-8):859-69.

Despite Scopolin is a main coumarin constituent in the stems of Erycibe obtusifolia Benth, a herb drug that has long been utilized in traditional Chinese medicine for the treatment of rheumatoid arthritis, little information is available about the pharmacological activities of this compound. The present study was performed to investigate the anti-rheumatic effects of Scopolin in adjuvant-induced arthritis (AIA) in rats, and explore the underlying mechanisms of action in views of anti-inflammatory and anti-angiogenic properties in the synovial tissues. Scopolin (50, 100 mg/kg), injected intraperitoneally for 10 days from the onset of secondary response, significantly inhibited both inoculated and non-inoculated paw swelling as well as articular index scores in AIA. Meanwhile, the mean body weight of rats treated with Scopolin was higher than that of model group. Rats treated with high dose of Scopolin (100 mg/kg) preserved a nearly normal histological architecture of the joints and showed a significant reduction of the new blood vessels in the synovial tissues. Additionally, Scopolin could reduce IL-6, VEGF and FGF-2 expressions in rat synovial tissues. In conclusion, Scopolin can reduce the clinical symptoms of rat AIA by inhibiting inflammation and angiogenesis, and this compound may be a potent agent for angiogenesis related diseases and can serve as a structural base for screening more potent synthetic analogs.

Antinociceptive properties of coumarins, steroid and dihydrostyryl-2-pyrones from Polygala sabulosa (Polygalaceae) in mice.[Pubmed:16393470]

J Pharm Pharmacol. 2006 Jan;58(1):107-12.

We have investigated the possible antinociceptive action of the extract, fractions and pure compounds obtained from the whole plant Polygala sabulosa A. W. Bennett (Polygalaceae) in acetic acid-induced visceral pain in mice. Intraperitoneal injection of animals with the hydroalcoholic extract and fractions (CH(2)Cl(2), EtOAc, n-BuOH, aqueous fraction) (1-100 mg kg(-1)) caused a dose-related and significant inhibition of the acetic acid-induced visceral nociceptive response. The CH(2)Cl(2), EtOAc and n-BuOH fractions were more potent than the hydroalcoholic extract and aqueous fraction. The isolated compounds dihydrostyryl-2-pyrones (1, 2, 3), styryl-2-pyrone (7), alpha-spinasterol (9), scopoletin (10) and two esters of the coumarin (scopoletin) obtained semisynthetically, acetylscopoletin (10a) and benzoylscopoletin (10b) (0.001-10 mg kg(-1)), exhibited significant and dose-related antinociceptive effects against acetic acid-induced visceral pain. The results distinguished, for the first time, the extract, fractions and pure compounds obtained from P. sabulosa that produced marked antinociception against the acetic acid-induced visceral nociceptive response, supporting the ethnomedical use of P. sabulosa.

Description

Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades.

Keywords:

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