Embelin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04074 |
| CAS | 550-24-3 |
| Molecular Weight | 294.39 |
| Molecular Formula | C17H26O4 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04074 | 100 mg | $199 | In stock |
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Add to cartDescription
Embelin, a quinone isolated from the Japanese Ardisia herb, is an inhibitor of X-linked inhibitor of apoptosis (XIAP) with IC50 of 4.1 uM.
Specification
| Synonyms | NSC91874; NSC91874; NSC 91874; Embelin; Emberine; Embelic acid |
| Storage | Store at -20°C, Under Inert Atmosphere |
| IUPAC Name | 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione |
| Canonical SMILES | CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O |
| InChI | InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3 |
| InChI Key | IRSFLDGTOHBADP-UHFFFAOYSA-N |
Properties
| Boiling Point | 431.9°C at 760 mmHg |
| Melting Point | 142-143°C |
| Density | 1.131 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1.Macrophage targeting contributes to the inhibitory effects of embelin on colitis-associated cancer.
Wu T1, Dai Y1, Wang W1, Teng G1, Jiao H2, Shuai X1, Zhang R3, Zhao P4, Qiao L5. Oncotarget. 2016 Jan 21. doi: 10.18632/oncotarget.6969. [Epub ahead of print]
Macrophages are a major component of inflammatory and tumor microenvironment. We previously reported that embelin suppresses colitis-associated tumorigenesis. Here, the role of macrophage targeting in the anti-inflammatory and anti-tumor properties of embelin was investigated. By using colitis-associated cancer (CAC) model, we demonstrated that embelin significantly depleted colon macrophages by blocking their recruitment. Moreover, embelin attenuated M2-like polarization of macrophages within the tumor microenvironment and eliminated their tumor-promoting functions during the development of CAC. Embelin potently inhibited NF-κB signaling in macrophages and decreased the production of key pro-inflammatory cytokines and tumorigenic factors involved in CAC, such as TNFα, IL-6 and COX-2. In addition, embelin directly reduced the polarization of M2 macrophages in vitro even in the presence of Th2 cytokines. These results suggested that targeting macrophages is, at least in part, responsible for the anti-tumor activity of embelin in CAC.
2.Domino Synthesis of Embelin Derivatives with Antibacterial Activity.
Peña R1, Martín P1, Feresin GE2, Tapia A2, Machín F3, Estévez-Braun A1. J Nat Prod. 2016 Feb 29. [Epub ahead of print]
A series of dihydropyran embelin derivatives was synthesized through a direct and highly efficient approach based on a domino Knoevenagel intramolecular hetero-Diels-Alder reaction from natural embelin (1), using unsaturated aldehydes in the presence of organocatalysts such as ethylendiamine diacetate or l-proline. The aliphatic aldehydes yielded exclusively trans adducts, while mixtures of trans and cis isomers were found in reactions with aromatic aldehydes, with the cis form always predominating. Some of the compounds obtained were active and selective against Gram-positive bacteria, including multiresistant Staphylococcus aureus clinical isolates.
3.Effect of embelin against 3-nitropropionic acid-induced Huntington's disease in rats.
Dhadde SB1, Nagakannan P2, Roopesh M2, Anand Kumar SR2, Thippeswamy BS2, Veerapur VP2, Badami S2. Biomed Pharmacother. 2016 Feb;77:52-8. doi: 10.1016/j.biopha.2015.11.009. Epub 2015 Dec 15.
3-Nitropropionic acid (3-NP) causes severe neurotoxicity in animals, which depicts Huntington's disease (HD) in humans. Embelin, the main active constituent of Embelia ribes, has been reported to possess various pharmacological actions, mainly anti-inflammatory, antioxidant, anticonvulsant and neuroprotective. The aim of the present study was to evaluate the neuroprotective effect of embelin against 3-NP induced experimental HD in rats. Adult Wistar rats were pretreated with vehicle/embelin (10 and 20mg/kg p.o.) for 7 days. From 8th day onwards, embelin was co-treated with 3-NP (15mg/kg, i.p.) for 7 days. At the end of the treatment schedule, animals were evaluated for behavioral alterations and brain homogenates were used for estimation of oxidative stress parameters (lipid peroxidation, reduced glutathione, catalase and glutathione-S-transferase). 2,3,5-Triphenyl tetrazolium chloride (TTC) stained brain slices were used for lesion size measurement.
4.Embelin inhibits proliferation, induces apoptosis and alters gene expression profiles in breast cancer cells.
Shah P1, Djisam R1, Damulira H1, Aganze A1, Danquah M2. Pharmacol Rep. 2016 Jan 19;68(3):638-644. doi: 10.1016/j.pharep.2016.01.004. [Epub ahead of print]
PURPOSE: To investigate effect of embelin on proliferation, apoptosis and gene expression profile changes in breast cancer cells.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
