Isojacareubin

CAS# 50597-93-8

Isojacareubin

Catalog No. BCN6883----Order now to get a substantial discount!

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Isojacareubin: 5mg $828 In Stock
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Quality Control of Isojacareubin

Number of papers citing our products

Chemical structure

Isojacareubin

3D structure

Chemical Properties of Isojacareubin

Cas No. 50597-93-8 SDF Download SDF
PubChem ID 9996463 Appearance Powder
Formula C18H14O6 M.Wt 326.31
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 6,10,11-trihydroxy-3,3-dimethylpyrano[2,3-c]xanthen-7-one
SMILES CC1(C=CC2=C3C(=C(C=C2O1)O)C(=O)C4=C(O3)C(=C(C=C4)O)O)C
Standard InChIKey FSTNFJKGRSHPBO-UHFFFAOYSA-N
Standard InChI InChI=1S/C18H14O6/c1-18(2)6-5-8-12(24-18)7-11(20)13-14(21)9-3-4-10(19)15(22)17(9)23-16(8)13/h3-7,19-20,22H,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 Isojacareubin

The roots of Garcinia fusca Pierre.

Biological Activity of Isojacareubin

Description1. Isojacareubin is a potent inhibitor of protein kinase C (PKC), suppresses hepatocellular carcinoma metastasis and induces apoptosis in vitro and in vivo, thus, it as a promising lead compound for the development of new antihepatoma agents. 2. Isojacareubin displays potent activity against H. pylori HP40 clinical isolate with MIC 23.9 uM, which is approximately two times greater than that of the standard drug amoxicillin.
TargetsPKC | MAPK | Antifection

Isojacareubin Dilution Calculator

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Isojacareubin Molarity Calculator

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Preparing Stock Solutions of Isojacareubin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0646 mL 15.3229 mL 30.6457 mL 61.2914 mL 76.6143 mL
5 mM 0.6129 mL 3.0646 mL 6.1291 mL 12.2583 mL 15.3229 mL
10 mM 0.3065 mL 1.5323 mL 3.0646 mL 6.1291 mL 7.6614 mL
50 mM 0.0613 mL 0.3065 mL 0.6129 mL 1.2258 mL 1.5323 mL
100 mM 0.0306 mL 0.1532 mL 0.3065 mL 0.6129 mL 0.7661 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 Isojacareubin

Anti-Helicobacter pylori xanthones of Garcinia fusca.[Pubmed:24155023]

Arch Pharm Res. 2014 Aug;37(8):972-7.

A new geranylated xanthone derivative, fuscaxanthone I (1), along with nine xanthones (2-9 and 11), a biphenyl (10) and three biflavonoids (12-14) were isolated from the roots of Garcinia fusca Pierre. Compounds 8, 10 and 11-14 were reported from this plant species for the first time. Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR and MS. The isolated compounds were evaluated for antibacterial activity against Helicobacter pylori. Cowaxanthone (5) and fukugiside (14) exhibited stronger inhibitory activity against H. pylori DMST reference strain at MICs 4.6 and 10.8 muM, respectively, than that of the control metronidazole. Isojacareubin (8) displayed the most potent activity against H. pylori HP40 clinical isolate with MIC 23.9 muM, which was approximately two times greater than that of the standard drug amoxicillin.

Isojacareubin from the Chinese herb Hypericum japonicum: potent antibacterial and synergistic effects on clinical methicillin-resistant Staphylococcus aureus (MRSA).[Pubmed:22942699]

Int J Mol Sci. 2012;13(7):8210-8.

Through bioassay-guided fractionation of the extracts from the aerial parts of the Chinese herb Hypericum japonicum Thunb. Murray, Isojacareubin (ISJ) was characterized as a potent antibacterial compound against the clinical methicillin-resistant Staphylococcus aureus (MRSA). The broth microdilution assay was used to determine the minimal inhibitory concentrations (MICs) and minimal bactericidal concentrations (MBCs) of ISJ alone. The results showed that its MICs/MBCs ranged from 4/16 to 16/64 mug/mL, with the concentrations required to inhibit or kill 50% of the strains (MIC(50)/MBC(50)) at 8/16 mug/mL. Synergistic evaluations of this compound with four conventional antibacterial agents representing different types were performed by the chequerboard and time-kill tests. The chequerboard method showed significant synergy effects when ISJ was combined with Ceftazidime (CAZ), Levofloxacin (LEV) and Ampicillin (AMP), with the values of 50% of the fractional inhibitory concentration indices (FICI(50)) at 0.25, 0.37 and 0.37, respectively. Combined bactericidal activities were also observed in the time-kill dynamic assay. The results showed the ability of ISJ to reduce MRSA viable counts by log(10)CFU/mL at 24 h of incubation at a concentration of 1 x MIC were 1.5 (LEV, additivity), 0.92 (CAZ, indifference) and 0.82 (AMP, indifference), respectively. These in vitro anti-MRSA activities of ISJ alone and its synergy with conventional antibacterial agents demonstrated that ISJ enhanced their efficacy, which is of potential use for single and combinatory therapy of patients infected with MRSA.

Bioassay-guided isolation of prenylated xanthones and polycyclic acylphloroglucinols from the leaves of Garcinia nujiangensis.[Pubmed:22871217]

J Nat Prod. 2012 Aug 24;75(8):1459-64.

Bioassay-guided fractionation of the acetone extract of the leaves of Garcinia nujiangensis resulted in the isolation of two new prenylated xanthones, nujiangexanthones A (1) and B (2), three new polycyclic polyprenylated acylphloroglucinols, nujiangefolins A-C (3-5), and 10 known related analogues. The structures of compounds 1-5 were elucidated by interpretation of their spectroscopic data. Compounds 3 and 4 are unusual polycyclic polyprenylated acylphloroglucinols in which the enol hydroxy group forms a six-membered ring with a benzene ring carbon. The compounds isolated were evaluated for their cytotoxic effects against 11 cancer cell lines and immortalized MIHA normal liver cells, and the test substances demonstrated selectivity toward the cancer cells. Isojacareubin (6) was found to be the most potent cytotoxic compound of those tested.

Inhibition of protein kinase C by isojacareubin suppresses hepatocellular carcinoma metastasis and induces apoptosis in vitro and in vivo.[Pubmed:26245668]

Sci Rep. 2015 Aug 6;5:12889.

Targeted inhibition of protein kinase C (PKC) inhibits hepatocellular carcinoma (HCC) proliferation and metastasis. We previously reported the cytotoxicity of a series of synthetic phenyl-substituted polyoxygenated xanthone derivatives against human HCC. In the current study, the most potent natural product, Isojacareubin (ISJ), was synthesized, and its cellular-level antihepatoma activities were evaluated. ISJ significantly inhibited cell proliferation and was highly selective for HCC cells in comparison to nonmalignant QSG-7701 hepatocytes. Moreover, ISJ exhibited pro-apoptotic effects on HepG2 hepatoma cells, as well as impaired HepG2 cell migration and invasion. Furthermore, ISJ was a potent inhibitor of PKC, with differential actions against various PKC isotypes. ISJ selectively inhibited the expression of aPKC (PKCzeta) in the cytosol and the translocation of cytosolic PKCzeta to membrane site. ISJ also directly interacted with cPKC (PKCalpha) and nPKC (PKCdelta, PKCepsilon and PKCmu) and thereby inhibited the early response of major MAPK phosphorylation and the late response of HCC cell invasion and proliferation. In a hepatoma xenograft model, ISJ pretreatment resulted in significant antihepatoma activity in vivo. These findings identify ISJ as a promising lead compound for the development of new antihepatoma agents and may guide the search for additional selective PKC inhibitors.

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