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3-Deoxysappanchalcone

CAS# 112408-67-0

3-Deoxysappanchalcone

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Chemical structure

3-Deoxysappanchalcone

3D structure

Chemical Properties of 3-Deoxysappanchalcone

Cas No. 112408-67-0 SDF Download SDF
PubChem ID 5319688 Appearance Powder
Formula C16H14O4 M.Wt 270.3
Type of Compound Chalcones Storage Desiccate at -20°C
Synonyms 2'-O-Methylisoliquiritigenin;51828-10-5
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (E)-1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
SMILES COC1=C(C=CC(=C1)O)C(=O)C=CC2=CC=C(C=C2)O
Standard InChIKey PACBGANPVNHGNP-RUDMXATFSA-N
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 3-Deoxysappanchalcone

The heartwood of Caesalpinia sappan Linn

Biological Activity of 3-Deoxysappanchalcone

Description1. 3-Deoxysappanchalcone is an effective HO-1 inducer at the translational level. 2. 3-Deoxysappanchalcone has anti-inflammatory effects, is a valuable compound for modulating inflammatory conditions. 3. 3-Deoxysappanchalcone has anti-influenza virus activity, the mechanism involved anti-apoptosis and anti-inflammation activities in vitro. 4. 3-Deoxysappanchalcone has inhibitory activity on MMP-9 expression and production in TNF-α-treated cells, is mediated by the suppression of AP-1 and NF-κB activation.
TargetsHO-1 | mTOR | Akt | NO | IL Receptor | TNF-α | AP-1 | NF-kB | MMP(e.g.TIMP)

3-Deoxysappanchalcone Dilution Calculator

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3-Deoxysappanchalcone Molarity Calculator

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Preparing Stock Solutions of 3-Deoxysappanchalcone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.6996 mL 18.498 mL 36.9959 mL 73.9919 mL 92.4898 mL
5 mM 0.7399 mL 3.6996 mL 7.3992 mL 14.7984 mL 18.498 mL
10 mM 0.37 mL 1.8498 mL 3.6996 mL 7.3992 mL 9.249 mL
50 mM 0.074 mL 0.37 mL 0.7399 mL 1.4798 mL 1.8498 mL
100 mM 0.037 mL 0.185 mL 0.37 mL 0.7399 mL 0.9249 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 3-Deoxysappanchalcone

3-Deoxysappanchalcone inhibits tumor necrosis factor-alpha-induced matrix metalloproteinase-9 expression in human keratinocytes through activated protein-1 inhibition and nuclear factor-kappa B DNA binding activity.[Pubmed:21628889]

Biol Pharm Bull. 2011;34(6):890-3.

Tumor necrosis factor alpha (TNF-alpha), which is a primary cytokine responsible for inflammatory responses in skin, induces the synthesis of matrix metalloproteinase-9 (MMP-9), which causes skin aging. The protective effects of 3-Deoxysappanchalcone against TNF-alpha-induced damage was investigated using human skin keratinocytes. The results showed that 3-Deoxysappanchalcone inhibited MMP-9 expression at the protein and mRNA level, by blocking the activation of activator protein-1 (AP-1) and nuclear factor kappa B (NF-kappaB). Taken together, the inhibitory activity of 3-Deoxysappanchalcone on MMP-9 expression and production in TNF-alpha-treated cells was found to be mediated by the suppression of AP-1 and NF-kappaB activation.

Sedative-hypnotic and anxiolytic effects and the mechanism of action of aqueous extracts of peanut stems and leaves in mice.[Pubmed:29572847]

J Sci Food Agric. 2018 Oct;98(13):4885-4894.

INTRODUCTION: Peanut stems and leaves (PSL) have traditionally been used as both a special food and a herbal medicine in Asia. The sedative-hypnotic and anxiolytic effects of PSL have been recorded in classical traditional Chinese literature, and more recently by many other researchers. In a previous study, four sleep-related ingredients (linalool, 5-hydroxy-4',7-dimethoxyflavanone, 2'-O-methylisoliquiritigenin and ferulic acid), among which 5-hydroxy-4',7-dimethoxyflavanone and 2'-O-methylisoliquiritigenin were newly found in Arachis species, were screened by ultrahigh-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC/QTOF-MS). In the current study, quantitative examination of the above four ingredients was conducted. Serious fundamental functional studies were done in mice, including locomotor activity, direct sleep tests, pentobarbital-induced sleeping time tests, subthreshold dose of pentobarbital tests and barbital sodium sleep incubation period tests, to determine the material base for the sedative-hypnotic and anxiolytic effects of aqueous extracts of PSL. Furthermore, neurotransmitter levels in three brain regions (cerebrum, cerebellum and brain stem) were determined using UHPLC coupled with triple-quadrupole mass spectrometry (UHPLC/QQQ-MS) in order to elucidate the exact mechanism of action. RESULTS: Aqueous extract of PSL at a dose of 500 mg kg(-1) (based on previous experience), along with different concentrations of the above four functional ingredients (189.86 microg kg(-1) linalool, 114.75 mg kg(-1) 5-hydroxy-4',7-dimethoxyflavanone, 32.4mg kg(-1) 2'-O-methylisoliquiritigenin and 44.44 mg kg(-1) ferulic acid), had a sedative-hypnotic effect by affecting neurotransmitter levels in mice. CONCLUSION: The data demonstrate that these four ingredients are the key functional factors for the sedative-hypnotic and anxiolytic effects of PSL aqueous extracts and that these effects occur via changes in neurotransmitter levels and pathways. (c) 2018 Society of Chemical Industry.

The anti-inflammatory effect of 3-deoxysappanchalcone is mediated by inducing heme oxygenase-1 via activating the AKT/mTOR pathway in murine macrophages.[Pubmed:25091623]

Int Immunopharmacol. 2014 Oct;22(2):420-6.

3-Deoxysappanchalcone (3-DSC), isolated from Caesalpinia sappan (Leguminosae), is a chalcone that exerts a variety of pharmacological activities. In the present study, we demonstrated that 3-DSC exerts anti-inflammatory activity in murine macrophages by inducing heme oxygenase-1 (HO-1) expression at the translational level. Treatment of RAW264.7 cells with 3-DSC induced HO-1 protein expression in a dose- and time-dependent manner without affecting HO-1 mRNA expression. Mitogen-activated protein kinase inhibitors or actinomycin D, a transcriptional inhibitor, did not block 3-DSC-mediated HO-1 induction. However, 3-DSC-mediated HO-1 induction was completely blocked by treatment with cycloheximide, a translational inhibitor, or rapamycin, an inhibitor of the mammalian target of rapamycin (mTOR). Strikingly, 3-DSC increased the phosphorylation level of mTOR downstream target molecules such as eukaryotic translation initiation factor 4E-binding protein 1 (4E-BP1) and S6 kinase 1 (S6K1), as well as AKT in a dose- and time-dependent manner, suggesting that the 3-DSC induces HO-1 expression by activating the AKT/mTOR pathway. Consistent with the notion that HO-1 has anti-inflammatory properties, 3-DSC inhibited the production of nitric oxide (NO) and interleukin (IL)-6 in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Inhibition of HO-1 activity by treatment with tin protoporphyrin IX, a specific HO-1 inhibitor, abrogated the inhibitory effects of 3-DSC on the production of NO and IL-6 in LPS-stimulated RAW264.7 cells. Taken together, 3-DSC may be an effective HO-1 inducer at the translational level that has anti-inflammatory effects, and a valuable compound for modulating inflammatory conditions.

The protective effect of 3-deoxysappanchalcone on in vitro influenza virus-induced apoptosis and inflammation.[Pubmed:22648377]

Planta Med. 2012 Jun;78(10):968-73.

Influenza virus is one of the most important causes of acute respiratory disease. Viral infection and viral replication activate multiple cell signalling pathways. Apoptosis of infected cells and immune response against viral replication, which are generally considered to be protective mechanisms, are also probably mediated by viruses, which lead to severe health problems. We previously reported that 3-Deoxysappanchalcone (3-DSC), a compound that is isolated from Caesalpinia sappan, exhibited in vitro anti-influenza activity. In the present study, we further identified that 3-DSC inhibited viral genomic replication and transcription only at a relatively high concentration. We then evaluated the effect of 3-DSC on the regulation of virus-induced cellular apoptosis. 3-DSC ameliorated virus-induced DNA fragmentation in a concentration-dependent manner, which tends to be a consequence of its inhibition of upstream caspase activation. 3-DSC also protected host cells against influenza-induced inflammation by suppressing CCL5 and CXCL10 secretions in endothelial cells and reducing the production of IL-6 and IL-1beta in monocytes/macrophages. In conclusion, our results demonstrate that anti-influenza virus mechanisms of 3-DSC involved anti-apoptosis and anti-inflammation activities in vitro. Moreover, 3-DSC could be a promising drug candidate for influenza treatment.

Description

3-Deoxysappanchalcone is a naturally-occurring chalcone compound isolated from Caesalpinia sappan L.

Keywords:

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