Isodiospyrin

CAS# 20175-84-2

Isodiospyrin

Catalog No. BCN4883----Order now to get a substantial discount!

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Quality Control of Isodiospyrin

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Chemical structure

Isodiospyrin

3D structure

Chemical Properties of Isodiospyrin

Cas No. 20175-84-2 SDF Download SDF
PubChem ID 99298 Appearance Red powder
Formula C22H14O6 M.Wt 374.4
Type of Compound Quinones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5-hydroxy-6-(4-hydroxy-2-methyl-5,8-dioxonaphthalen-1-yl)-7-methylnaphthalene-1,4-dione
SMILES CC1=CC(=C2C(=O)C=CC(=O)C2=C1C3=C(C=C4C(=O)C=CC(=O)C4=C3O)C)O
Standard InChIKey OEEOHKZVBKYMBA-UHFFFAOYSA-N
Standard InChI InChI=1S/C22H14O6/c1-9-7-11-12(23)3-4-13(24)19(11)22(28)18(9)17-10(2)8-16(27)20-14(25)5-6-15(26)21(17)20/h3-8,27-28H,1-2H3
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 Isodiospyrin

The herbs of Diospyros morrisiana

Biological Activity of Isodiospyrin

Description1. Isodiospyrin is a novel human DNA topoisomerase I inhibitor, it exhibits cytotoxic activity to tumor cell lines. 2. Isodiospyrin has antibacterial activity, the minimum inhibitory concentrations (MICs) against Gram-positive bacteria ranged from 0.78 to 50 microg/mL. 3. Isodiospyrin shows high antifungal activity against P. obscurans at 30uM with 81.4% growth inhibition, and moderate activity against P. viticola (36.6%).
TargetsTopoisomerase | Antifection

Isodiospyrin Dilution Calculator

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Isodiospyrin Molarity Calculator

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Preparing Stock Solutions of Isodiospyrin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6709 mL 13.3547 mL 26.7094 mL 53.4188 mL 66.7735 mL
5 mM 0.5342 mL 2.6709 mL 5.3419 mL 10.6838 mL 13.3547 mL
10 mM 0.2671 mL 1.3355 mL 2.6709 mL 5.3419 mL 6.6774 mL
50 mM 0.0534 mL 0.2671 mL 0.5342 mL 1.0684 mL 1.3355 mL
100 mM 0.0267 mL 0.1335 mL 0.2671 mL 0.5342 mL 0.6677 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 Isodiospyrin

Antifungal metabolites from the roots of Diospyros virginiana by overpressure layer chromatography.[Pubmed:22162171]

Chem Biodivers. 2011 Dec;8(12):2331-40.

A preparative overpressure layer chromatography (OPLC) method was successfully used for the separation of two new natural compounds, 4-hydroxy-5,6-dimethoxynaphthalene-2-carbaldehyde (1) and 12,13-didehydro-20,29-dihydrobetulin (2) together with nine known compounds, including 7-methyljuglone (3), diospyrin (4), Isodiospyrin (5), shinanolone (6), lupeol (7), betulin (8), betulinic acid (9), betulinaldehyde (10), and ursolic acid (11) from the acetone extract of the roots of Diospyros virginiana. Their identification was accomplished by 1D- and 2D-NMR spectroscopy and HR-ESI-MS methods. All the isolated compounds were evaluated for their antifungal activities against Colletotrichum fragariae, C. gloeosporioides, C. acutatum, Botrytis cinerea, Fusarium oxysporum, Phomopsis obscurans, and P. viticola using in vitro micro-dilution broth assay. The results indicated that compounds 3 and 5 showed high antifungal activity against P. obscurans at 30 muM with 97.0 and 81.4% growth inhibition, and moderate activity against P. viticola (54.3 and 36.6%). It appears that an optimized OPLC system offers a rapid and efficient method of exploiting bioactive natural products.

Antibacterial activity of diospyrin, isodiospyrin and bisisodiospyrin from the root of Diospyros piscatoria (Gurke) (Ebenaceae).[Pubmed:10685108]

Phytother Res. 2000 Mar;14(2):112-7.

Two dimeric naphthoquinones, diospyrin and Isodiospyrin, isolated from the root of Diospyros piscatoria (Gurke), a common ingredient in several folk medicines, have been shown to have a broad spectrum of antibacterial activity. The minimum inhibitory concentrations (MICs) of diospyrin against Streptococcus pyogenes ATCC 12344 and Streptococcus pneumoniae ATCC 33400 ranged from 1.56 to 50 microg/mL. While those against Salmonella choleraesuis serotype typhi (S. typhi), ATCC 6539 and Mycobacterium chelonae ATCC 19977 were between 25 and 100 microg/mL. Isodiospyrin was more active than its racemic isomer diospyrin. The MICs against Gram-positive bacteria ranged from 0.78 to 50 microg/mL. While those against Pseudomonas aeruginosa ATCC 15443 and S. typhi ranged from 50 to 100 microg/mL. The MIC for M. chelonae was between 6.25 and 25 microg/mL. MICs were found to increase with the concentration of cells used for the inoculum. The MICs for Bacillus subtilis ATCC 6633 increased up to the highest concentration of cells tested. The same phenomenon was observed on M. chelonae, but with better effect in the latter. The kinetics of bacteria studies against both B. subtilis and M. chelonae increases with increasing concentration of Isodiospyrin tested. Two tetrameric forms of plumbagin were isolated. The naphthoquinone bisIsodiospyrin, gave MIC values between 300 and 400 micro g/mL. The second, as yet unidentified tetramer, was not active at 500 micro g/mL.

Isodiospyrin as a novel human DNA topoisomerase I inhibitor.[Pubmed:14599556]

Biochem Pharmacol. 2003 Nov 15;66(10):1981-91.

Isodiospyrin is a natural product from the plant Diospyros morrisiana, which consists of an asymmetrical 1,2-binaphthoquinone chromophore. Isodiospyrin exhibits cytotoxic activity to tumor cell lines but very little is known about its cellular target and mechanism of action. Unlike the prototypic human topoisomerase I (htopo I) poison camptothecin, Isodiospyrin does not induce htopo I-DNA covalent complexes. However, Isodiospyrin antagonizes camptothecin-induced, htopo I-mediated DNA cleavage. Binding analysis indicated that Isodiospyrin binds htopo I but not DNA. These results suggest that Isodiospyrin inhibits htopo I by direct binding to htopo I, which limits htopo I access to the DNA substrate. Furthermore, Isodiospyrin exhibits strong inhibitory effect on the kinase activity of htopo I toward splicing factor 2/alternate splicing factor in the absence of DNA. Thus, these findings have important implications on naphthoquinone and its derivatives' cellular mode of actions, i.e. these novel DNA topoisomerase I inhibitors can prevent both DNA relaxation and kinase activities of htopo I.

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