Isoscopoletin

CAS# 776-86-3

Isoscopoletin

Catalog No. BCN4582----Order now to get a substantial discount!

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Isoscopoletin: 5mg $184 In Stock
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Quality Control of Isoscopoletin

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Chemical structure

Isoscopoletin

3D structure

Chemical Properties of Isoscopoletin

Cas No. 776-86-3 SDF Download SDF
PubChem ID 69894 Appearance White-beige powder
Formula C10H8O4 M.Wt 192.17
Type of Compound Coumarins Storage Desiccate at -20°C
Synonyms Esculetin 7-methyl ether; 6-Hydroxy 7-methoxycoumarin; 7-Methoxyesculetin
Solubility Soluble in chloroform and pyridine
Chemical Name 6-hydroxy-7-methoxychromen-2-one
SMILES COC1=C(C=C2C=CC(=O)OC2=C1)O
Standard InChIKey SYTYLPHCLSSCOJ-UHFFFAOYSA-N
Standard InChI InChI=1S/C10H8O4/c1-13-9-5-8-6(4-7(9)11)2-3-10(12)14-8/h2-5,11H,1H3
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 Isoscopoletin

1 Euphorbia sp. 2 Fraxinus sp. 3 Mentzelia sp. 4 Morinda sp. 5 Olea sp. 6 Saussurea sp.

Biological Activity of Isoscopoletin

DescriptionIsoscopoletin possesses inhibitory activity against hepatitis B virus (HBV) replication; it also shows substantial inhibition against multi-drug resistant CEM/ADR5000 cells and human CCRF-CEM leukaemia cells, with the IC50 value is 1.6 and 4.0 microM, respectively.
TargetsHBV
In vitro

Activity-guided isolation of scopoletin and isoscopoletin, the inhibitory active principles towards CCRF-CEM leukaemia cells and multi-drug resistant CEM/ADR5000 cells, from Artemisia argyi.[Pubmed: 16881019]

Planta Med. 2006 Jul;72(9):862-4.


METHODS AND RESULTS:
The ethyl acetate extract of Artemisia argyi leaves showed substantial inhibition in a cell proliferation assay using human CCRF-CEM leukaemia cells. Bioassay-guided fractionation of the extract led to the isolation of scopoletin and Isoscopoletin as the active principles. Their IC50 values were 2.6 and 4.0 microM, respectively. Additionally the two substances were tested against the multidrug resistant subline, CEM/ADR5000 where they both showed IC50 values of 1.6 microM.
CONCLUSIONS:
In contrast to the standard cytostatic drugs doxorubicin, vincristine, and paclitaxel, CEM/ADR5000 cells therefore did not exhibit cross-resistance to scopoletin and Isoscopoletin.

Evaluation of antiviral activity of compounds isolated from Ranunculus sieboldii and Ranunculus sceleratus.[Pubmed: 16395649 ]

Planta Med. 2005 Dec;71(12):1128-33.


METHODS AND RESULTS:
Nineteen compounds isolated from Ranunculus sieboldii and Ranunculus sceleratus were tested for inhibitory effects on hepatitis B virus (HBV) and Herpes simplex virus type-1 (HSV-1). The results showed that apigenin 4'- O- alpha-rhamnopyranoside, apigenin 7- O- beta-glucopyranosyl-4'- O- alpha-rhamnopyranoside, tricin 7- O- beta-glucopyranoside, tricin, and Isoscopoletin possessed inhibitory activity against HBV replication. Protocatechuyl aldehyde exhibited an inhibiting activity on HSV-1 replication.
CONCLUSIONS:
It is therefore suggested that further investigations on these bioactive compounds might be needed to discover and develop new antiviral agents.

Protocol of Isoscopoletin

Cell Research

Machilusmarin, a new neuroprotective isocoumarin dimer from the stems of Machilus ichangensis Rehd. et Wils.[Pubmed: 23082968 ]

Nat Prod Res. 2013;27(17):1542-7.

A new isocoumarin dimer, Machilusmarin (1), was isolated from the stem of Machilus ichangensis Rehd. et Wils., together with two known coumarins, scopoletin (2) and Isoscopoletin (3).
METHODS AND RESULTS:
The structure of Machilusmarin (1) was elucidated by HRMS and NMR spectrums. Machilusmarin (1) showed significant neuroprotective activity against SH-SY5Y human neuroblastoma cells apoptosis induced by hydrogen peroxide at concentrations ranging from 0.625 to 10.0 μg mL(-1).

Isoscopoletin Dilution Calculator

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Isoscopoletin Molarity Calculator

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Preparing Stock Solutions of Isoscopoletin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.2037 mL 26.0186 mL 52.0373 mL 104.0745 mL 130.0931 mL
5 mM 1.0407 mL 5.2037 mL 10.4075 mL 20.8149 mL 26.0186 mL
10 mM 0.5204 mL 2.6019 mL 5.2037 mL 10.4075 mL 13.0093 mL
50 mM 0.1041 mL 0.5204 mL 1.0407 mL 2.0815 mL 2.6019 mL
100 mM 0.052 mL 0.2602 mL 0.5204 mL 1.0407 mL 1.3009 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 Isoscopoletin

Machilusmarin, a new neuroprotective isocoumarin dimer from the stems of Machilus ichangensis Rehd. et Wils.[Pubmed:23082968]

Nat Prod Res. 2013;27(17):1542-7.

A new isocoumarin dimer, Machilusmarin (1), was isolated from the stem of Machilus ichangensis Rehd. et Wils., together with two known coumarins, scopoletin (2) and Isoscopoletin (3). The structure of Machilusmarin (1) was elucidated by HRMS and NMR spectrums. Machilusmarin (1) showed significant neuroprotective activity against SH-SY5Y human neuroblastoma cells apoptosis induced by hydrogen peroxide at concentrations ranging from 0.625 to 10.0 microg mL(-1).

Activity-guided isolation of scopoletin and isoscopoletin, the inhibitory active principles towards CCRF-CEM leukaemia cells and multi-drug resistant CEM/ADR5000 cells, from Artemisia argyi.[Pubmed:16881019]

Planta Med. 2006 Jul;72(9):862-4.

The ethyl acetate extract of Artemisia argyi leaves showed substantial inhibition in a cell proliferation assay using human CCRF-CEM leukaemia cells. Bioassay-guided fractionation of the extract led to the isolation of scopoletin and Isoscopoletin as the active principles. Their IC50 values were 2.6 and 4.0 microM, respectively. Additionally the two substances were tested against the multidrug resistant subline, CEM/ADR5000 where they both showed IC50 values of 1.6 microM. In contrast to the standard cytostatic drugs doxorubicin, vincristine, and paclitaxel, CEM/ADR5000 cells therefore did not exhibit cross-resistance to scopoletin and Isoscopoletin.

Evaluation of antiviral activity of compounds isolated from Ranunculus sieboldii and Ranunculus sceleratus.[Pubmed:16395649]

Planta Med. 2005 Dec;71(12):1128-33.

Nineteen compounds isolated from Ranunculus sieboldii and Ranunculus sceleratus were tested for inhibitory effects on hepatitis B virus (HBV) and Herpes simplex virus type-1 (HSV-1). The results showed that apigenin 4'- O- alpha-rhamnopyranoside, apigenin 7- O- beta-glucopyranosyl-4'- O- alpha-rhamnopyranoside, tricin 7- O- beta-glucopyranoside, tricin, and Isoscopoletin possessed inhibitory activity against HBV replication. Protocatechuyl aldehyde exhibited an inhibiting activity on HSV-1 replication. It is therefore suggested that further investigations on these bioactive compounds might be needed to discover and develop new antiviral agents.

Description

Isoscopoletin (6-Hydroxy-7-methoxycoumarin) is an active constituent in Artemisia argyi leaves. Isoscopoletin shows substantial inhibition against cell proliferation, with IC50s of 4.0 μM and 1.6 μM for human CCRF-CEM leukaemia cells and multidrug resistant subline CEM/ADR5000, respectively. Isoscopoletin (6-Hydroxy-7-methoxycoumarin) possesses inhibitory activity against HBV replication.

Keywords:

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