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Sappanchalcone
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Product Name Sappanchalcone
Price: $318 / 10mg
CAS No.: 94344-54-4
Catalog No.: CFN97522
Molecular Formula: C16H14O5
Molecular Weight: 286.3 g/mol
Purity: >=98%
Type of Compound: Chalcones
Physical Desc.: Orange powder
Source: The heartwoods of Caesalpinia sappan L.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download: COA    MSDS    SDF    Manual
Similar structural: Comparison (Web)  (SDF)
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According to end customer requirements, ChemFaces provide solvent format. This solvent format of product intended use: Signaling Inhibitors, Biological activities or Pharmacological activities.
Size /Price /Stock 10 mM * 1 mL in DMSO / $135.6 / In-stock
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Related Screening Libraries
Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries
Biological Activity
Description: Sappanchalcone shows xanthine oxidase inhibitory activity, is a xanthine oxidase inhibitor. Sappanchalcone has cytoprotective, and anti-inflammatory effects, it could be used as an anti-inflammatory and bone-protective agent during the treatment of rheumatoid arthritis. Sappanchalcone blocks cell cycle progression in the G2/M phase, it suppresses oral cancer cell growth and induces apoptosis through the activation of p53-dependent mitochondrial, p38, ERK, JNK, and NF-κB signaling, could potentially used to treat periodontal, pulpal , periapical inflammatory lesion and oral cancer. Sappanchalcone possesses the most potent effect against allergic reaction in basophilic leukemic (RBL-2H3) cells with an inhibitory concentration (IC50) value of 7.6 uM, it may have anti-allergic activity.
Targets: TNF-α | IL Receptor | Bcl-2/Bax | Caspase | p53 | NF-kB | ERK | JNK | p38MAPK | HO-1 | Nrf2 | NO | PGE | STAT | NOS
In vitro:
Chin J Nat Med. 2014 Aug;12(8):607-12.
Inhibitory activities of Lignum Sappan extractives on growth and growth-related signaling of tumor cells.[Pubmed: 25156286]
To investigate the active constituents of Lignum Sappan (Caesalpinia sappan L.) on growth-related signaling and cell mitosis.
METHODS AND RESULTS:
The influence of the ethyl acetate (EtOAc) extract of Lignum Sappan and its constituents on growth-related signaling were evaluated by a luciferase assay in cells stably-transfected with NF-κB, STAT1, or STAT3 responsive luciferase reporter plasmid. The inhibitory effect on the cell cycle was determined by flow cytometric analysis. The anti-tumor activities were assessed in vitro and in vivo. The EtOAc extract of Lignum Sappan had inhibitory activities on growth-related signaling and cell mitosis. Three major active compounds were Sappanchalcone, brazilin, and butein. Sappanchalcone blocked cell cycle progression in the G2/M phase, brazilin inhibited TNFα/NF-κB signaling, while butein inhibited IL-6/STAT3 signaling, as well as TNFα/NF-κB signaling. The three compounds all demonstrated cytotoxic activities against human tumor cells in vitro. In a S180 tumor cell-bearing mice model, the anti-tumor efficacy of the EtOAc extract was better than the individual compounds acting alone.
CONCLUSIONS:
These results indicate that Lignum Sappan contains multiple active compounds with different antitumor activities, which act synergistically to enhance their anti-tumor effects. The EtOAc extract of Lignum Sappan may be better than individual active constituent as a novel medicine for the treatment of cancer.
Phytother. Res., 2009, 23(7):1028-31.
Anti-allergic activity of principles from the roots and heartwood of Caesalpinia sappan on antigen-induced β-hexosaminidase release.[Reference: WebLink]

METHODS AND RESULTS:
The dichloromethane extract of the roots and heartwood of Caesalpinia sappan exhibited potent inhibitory activity against beta-hexosaminidase release as marker of degranulation in rat basophilic leukemic (RBL-2H3) cells, with inhibition of 98.7% and 87.5% at concentration of 100 microg/ml, respectively. These extracts were further separated by chromatographic techniques to give two chalcones and seven homoisoflavones. Among the compounds tested, Sappanchalcone (2) possessed the most potent effect against allergic reaction in RBL-2H3 cells with an inhibitory concentration (IC50) value of 7.6 microM, followed by 3-deoxySappanchalcone (1, IC50 = 15.3 microM), whereas other compounds showed moderate and mild effects.
CONCLUSIONS:
The results suggested the following structural requirements of chalcones (1 and 2) and homoisoflavones (3-9) for anti-allergic activity: (i) chalcone exhibited higher activity than homoisoflavone (ii) vicinal hydroxylation at B-ring of chalcone conferred higher activity than one hydroxylation; and (iii) for homoisoflavone, the hydroxyl groups at C-3 and C-4 positions decreased the activity. This is the first report of C. sappan for anti-allergic activity.
In vivo:
Arch Pharm Res. 2015 Jun;38(6):973-83.
Anti-inflammatory activity of sappanchalcone isolated from Caesalpinia sappan L. in a collagen-induced arthritis mouse model.[Pubmed: 25586964]
Sappanchalcone, a bioactive flavonoid isolated from the heartwood of Caesalpinia sappan L. possesses anti-inflammatory effects. We studied the efficacy of Sappanchalcone in attenuating collagen-induced arthritis (CIA) in a mouse model of rheumatoid arthritis.
METHODS AND RESULTS:
Sappanchalcone was purified to homogeneity from the chloroform fraction of the methanolic extract of C. sappan, and identified using mass spectrometry and (1)H-nuclear magnetic resonance spectroscopy. CIA-induced male DBA/1J mice were divided into control, Sappanchalcone-treated, and methotrexate-treated groups (n = 10 per group). Paw swelling, arthritis severity, radiographic and histomorphometric changes were assessed to measure the protective role of Sappanchalcone against chronic disease progression. Sappanchalcone administration significantly reduced clinical arthritis and inflammatory edema in paws. Bone mineral density and trabecular structure were maintained in CIA mice administered Sappanchalcone. The levels of pro-inflammatory cytokines (TNF-α, IL-6, and 1L-1β) were significantly lower in the serum of Sappanchalcone-treated mice as compared with the control group.
CONCLUSIONS:
Our results suggest that Sappanchalcone could be used as an anti-inflammatory and bone-protective agent during the treatment of rheumatoid arthritis.
Sappanchalcone Description
Source: The heartwoods of Caesalpinia sappan L.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

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Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4928 mL 17.4642 mL 34.9284 mL 69.8568 mL 87.321 mL
5 mM 0.6986 mL 3.4928 mL 6.9857 mL 13.9714 mL 17.4642 mL
10 mM 0.3493 mL 1.7464 mL 3.4928 mL 6.9857 mL 8.7321 mL
50 mM 0.0699 mL 0.3493 mL 0.6986 mL 1.3971 mL 1.7464 mL
100 mM 0.0349 mL 0.1746 mL 0.3493 mL 0.6986 mL 0.8732 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Kinase Assay:
Toxicol In Vitro. 2011 Dec;25(8):1782-8.
Mechanism of sappanchalcone-induced growth inhibition and apoptosis in human oral cancer cells.[Pubmed: 21963806]
Sappanchalcone, a flavonoid extracted from Caesalpinia sappan, exhibits cytoprotective activity, but the molecular basis for the anticancer effect of Sappanchalcone has not been reported.
METHODS AND RESULTS:
In this study, we examined whether Sappanchalcone could inhibit the growth of human primary and metastatic oral cancer cells, and we analyzed the signaling pathway underlying the apoptotic effects of the compound in this process using 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyltetrazolium bromide (MTT) assays, fluorescence microscopy, flow cytometry, and Western blotting. Sappanchalcone-treated oral cancer cells showed an increased cytosolic level of cytochrome c, downregulated Bcl-2 expression, upregulated Bax and p53 expression, caspase-3 and -9 activation, and poly (ADP-ribose) polymerase cleavage. Furthermore, Sappanchalcone induced activation of p38, extracellular signal-regulated kinase (ERK), c-Jun amino-terminal kinase (JNK), and Nuclear factor k B (NF-κB), as demonstrated by the phosphorylation of each mitogen-activated protein kinases (MAPKs), the degradation of inhibitor of NF-κα (IκB-α), increased expression of nuclear p65, and NF-κB-DNA binding. Inhibition of the expression of p38, ERK, JNK, and NF-κB by pharmacological inhibitors reversed Sappanchalcone-induced growth inhibition and apoptosis.
CONCLUSIONS:
These results provide the first evidence that Sappanchalcone suppresses oral cancer cell growth and induces apoptosis through the activation of p53-dependent mitochondrial, p38, ERK, JNK, and NF-κB signaling. Thus, it has potential as a chemotherapeutic agent for oral cancer.
Eur J Pharmacol. 2010 Oct 10;644(1-3):230-7.
Effects of sappanchalcone on the cytoprotection and anti-inflammation via heme oxygenase-1 in human pulp and periodontal ligament cells.[Pubmed: 20621084]
Sappanchalcone has been demonstrated to possess several biological effects. However, the molecular mechanism underlying these effects is not fully understood.
METHODS AND RESULTS:
In this study, we examined the effects of Sappanchalcone on hydrogen peroxide (H(2)O(2))-induced cytotoxicity using human dental pulp (HDP) cells, and lipopolysaccharide (LPS)-induced inflammation using human periodontal ligament (HPDL) cells. Sappanchalone concentration proportionately increased heme oxygenase (HO)-1 protein expression and enzyme activity in both HDP and HPDL cells. It also protected HDP cells from H(2)O(2)-induced cytotoxicity and reactive oxygen species production. The cytoprotective effect of Sappanchalcone was nullified by HO-1 inhibitor, Tin protoporphyrin (SnPP). Sappanchalcone is seen to inhibit LPS-stimulated nitric oxide (NO), prostaglandin E(2) (PGE(2)), interlukine-1beta (IL-1beta), tumor necrosis factor-alpha (TNF-alpha), interlukine-6 (IL-6) and interlukine-12 (IL-12) release in addition to inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression in HPDL cells. SnPP, a specific inhibitor of HO-1, partly blocked Sappanchalcone mediated suppression of inflammatory mediator production, in LPS-stimulated HPDL cells. HDP and HPDL cells treated with Sappanchalcone exhibited the transient activation of c-Jun NH2-terminal kinase (JNK) and NF-E2-related factor-2 (Nrf2). The expression of HO-1 protein by Sappanchalcone was significantly reduced by pretreatment with JNK inhibitor.
CONCLUSIONS:
In conclusion, induction of HO-1 is an important cytoprotective mechanism by which Sappanchalcone protects HDP cells from H(2)O(2) and in addition it also exhibits anti-inflammatory effects in LPS-stimulated HPDL cells. Thus, Sappanchalcone could potentially be a therapeutic approach for periodontal, pulpal and periapical inflammatory lesion.
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