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Dehydroglyasperin D

CAS# 517885-72-2

Dehydroglyasperin D

2D Structure

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Dehydroglyasperin D

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Chemical Properties of Dehydroglyasperin D

Cas No. 517885-72-2 SDF Download SDF
PubChem ID 10109594 Appearance Powder
Formula C22H24O5 M.Wt 368.42
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 4-[5,7-dimethoxy-6-(3-methylbut-2-enyl)-2H-chromen-3-yl]benzene-1,3-diol
SMILES CC(=CCC1=C(C=C2C(=C1OC)C=C(CO2)C3=C(C=C(C=C3)O)O)OC)C
Standard InChIKey QHJJASRUTXHRAL-UHFFFAOYSA-N
Standard InChI InChI=1S/C22H24O5/c1-13(2)5-7-17-20(25-3)11-21-18(22(17)26-4)9-14(12-27-21)16-8-6-15(23)10-19(16)24/h5-6,8-11,23-24H,7,12H2,1-4H3
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 Dehydroglyasperin D

The roots of Glycyrrhiza uralensis (G. uralensis).

Biological Activity of Dehydroglyasperin D

Description1. Dehydroglyasperin D exhibits anti-obesity, antioxidant and anti-aldose reductase effects. 2. Dehydroglyasperin D has potent anticancer activity, it inhibits the proliferation of HT-29 human colorectal cancer cells through direct interaction with phosphatidylinositol 3-kinase. 3. Dehydroglyasperin D may be a promising anti-inflammatory agent that mediates suppression of both COX-2 expression and the MLK3 signalling pathway through direct binding and inhibition of MLK3. 4. Dehydroglyasperin D shows strong ferric reducing activities and effectively scavenged DPPH, ABTS(+), and singlet oxygen radicals.
TargetsPI3K | Akt | GSK-3 | COX | PGE | AP-1 | JNK | p38MAPK | ROS

Dehydroglyasperin D Dilution Calculator

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Preparing Stock Solutions of Dehydroglyasperin D

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7143 mL 13.5715 mL 27.1429 mL 54.2859 mL 67.8573 mL
5 mM 0.5429 mL 2.7143 mL 5.4286 mL 10.8572 mL 13.5715 mL
10 mM 0.2714 mL 1.3571 mL 2.7143 mL 5.4286 mL 6.7857 mL
50 mM 0.0543 mL 0.2714 mL 0.5429 mL 1.0857 mL 1.3571 mL
100 mM 0.0271 mL 0.1357 mL 0.2714 mL 0.5429 mL 0.6786 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 Dehydroglyasperin D

Aldose reductase inhibitory compounds from Glycyrrhiza uralensis.[Pubmed:20460778]

Biol Pharm Bull. 2010;33(5):917-21.

We evaluated the inhibitory effects of components from the root of Glycyrrhiza uralensis (G. uralensis) on aldose reductase (AR) and sorbitol formation in rat lenses with high levels of glucose as part of our ongoing search of natural sources for therapeutic and preventive agents for diabetic complications. In order to identify the bioactive components of G. uralensis, 5 prenylated flavonoids (semilicoisoflavone B, 7-O-methylluteone, dehydroglyasperin C, Dehydroglyasperin D, and isoangustone A), three flavonoids (liquiritigenin, isoliquiritigenin, and licochalcone A), and two triterpenoids (glycyrrhizin and glycyrrhetinic acid) were isolated; their chemical structures were then elucidated on the basis of spectroscopic evidence and comparison with published data. The anti-diabetic complication activities of 10 G. uralensis-derived components were investigated via inhibitory assays using rat lens AR (rAR) and human recombinant AR (rhAR). From the 10 isolated compounds, semilicoisoflavone B showed the most potent inhibition, with the IC(50) values of rAR and rhAR at 1.8 and 10.6microM, respectively. In the kinetic analyses using Lineweaver.Burk plots of 1/velocity and 1/concentration of substrate, semilicoisoflavone B showed noncompetitive inhibition against rhAR. The results clearly indicated that the presence of a gamma,gamma-dimethylchromene ring is partly responsible for the AR inhibitory activity of isoprenoid-type flavonoids. Further, semilicoisoflavone B inhibited sorbitol formation of rat lens incubated with a high concentration of glucose, indicating that this compound may be effective for preventing osmotic stress in hyperglycemia.

MLK3 is a novel target of dehydroglyasperin D for the reduction in UVB-induced COX-2 expression in vitro and in vivo.[Pubmed:25176057]

J Cell Mol Med. 2015 Jan;19(1):135-42.

Dehydroglyasperin D (DHGA-D), a compound present in licorice, has been found to exhibit anti-obesity, antioxidant and anti-aldose reductase effects. However, the direct molecular mechanism and molecular targets of DHGA-D during skin inflammation remain unknown. In the present study, we investigated the effect of DHGA-D on inflammation and its mechanism of action on UVB-induced skin inflammation in HaCaT human keratinocytes and SKH-1 hairless mice. DHGA-D treatment strongly suppressed UVB-induced COX-2 expression, PGE2 generation and AP-1 transactivity in HaCaT cells without affecting cell viability. DHGA-D also inhibited phosphorylation of the mitogen-activated protein kinase kinase (MKK) 3/6/p38, MAPK/Elk-1, MKK4/c-Jun N-terminal kinase (JNK) 1/2/c-Jun/mitogen, and stress-activated protein kinase (MSK), whereas phosphorylation of the mixed-lineage kinase (MLK) 3 remained unaffected. Kinase and co-precipitation assays with DHGA-D Sepharose 4B beads showed that DHGA-D significantly suppressed MLK3 activity through direct binding to MLK3. Knockdown of MLK3 suppressed COX-2 expression as well as phosphorylation of MKK4/p38 and MKK3/6/JNK1/2 in HaCaT cells. Furthermore, Western blot assay and immunohistochemistry results showed that DHGA-D pre-treatment significantly inhibits UVB-induced COX-2 expression in vivo. Taken together, these results indicate that DHGA-D may be a promising anti-inflammatory agent that mediates suppression of both COX-2 expression and the MLK3 signalling pathway through direct binding and inhibition of MLK3.

Antioxidant activities of licorice-derived prenylflavonoids.[Pubmed:23346298]

Nutr Res Pract. 2012 Dec;6(6):491-8.

Glycyrrhiza uralensis (or licorice) is a widely used Oriental herbal medicine from which the phenylflavonoids dehydroglyasperin C (DGC), Dehydroglyasperin D (DGD), and isoangustone A (IsoA) are derived. The purpose of the present study was to evaluate the antioxidant properties of DGC, DGD, and IsoA. The three compounds showed strong ferric reducing activities and effectively scavenged DPPH, ABTS(+), and singlet oxygen radicals. Among the three compounds tested, DGC showed the highest free radical scavenging capacity in human hepatoma HepG2 cells as assessed by oxidant-sensitive fluorescent dyes dichlorofluorescein diacetate and dihydroethidium bromide. In addition, all three compounds effectively suppressed lipid peroxidation in rat tissues as well as H(2)O(2)-induced ROS production in hepatoma cells. This study demonstrates that among the three phenylflavonoids isolated from licorice, DGC possesses the most potent antioxidant activity, suggesting it has protective effects against chronic diseases caused by reactive oxygen species as well as potential as an antioxidant food additive.

Dehydroglyasperin D Inhibits the Proliferation of HT-29 Human Colorectal Cancer Cells Through Direct Interaction With Phosphatidylinositol 3-kinase.[Pubmed:27051646]

J Cancer Prev. 2016 Mar;21(1):26-31.

BACKGROUND: Despite recent advances in therapy, colorectal cancer still has a grim prognosis. Although licorice has been used in East Asian traditional medicine, the molecular properties of its constituents including Dehydroglyasperin D (DHGA-D) remain unknown. We sought to evaluate the inhibitory effect of DHGA-D on colorectal cancer cell proliferation and identify the primary signaling molecule targeted by DHGA-D. METHODS: We evaluated anchorage-dependent and -independent cell growth in HT-29 human colorectal adenocarcinoma cells. The target protein of DHGA-D was identified by Western blot analysis with a specific antibody, and direct interaction between DHGA-D and the target protein was confirmed by kinase and pull-down assays. Cell cycle analysis by flow cytometry and further Western blot analysis was performed to identify the signaling pathway involved. RESULTS: DHGA-D significantly suppressed anchorage-dependent and -independent HT-29 colorectal cancer cell proliferation. DHGA-D directly suppressed phosphatidylinositol 3-kinase (PI3K) activity and subsequent Akt phosphorylation and bound to the p110 subunit of PI3K. DHGA-D also significantly induced G1 cell cycle arrest, together with the suppression of glycogen synthase kinase 3beta and retinoblastoma phosphorylation and cyclin D1 expression. CONCLUSIONS: DHGA-D has potent anticancer activity and targets PI3K in human colorectal adenocarcinoma HT-29 cells. To our knowledge, this is the first report to detail the molecular basis of DHGA-D in suppressing colorectal cancer cell growth.

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