13,21-Didehydrochaparrinone
(1beta,11alpha,12alpha)-1,11,12-trihydroxy-11,20-epoxypicrasa-3,13(21)-diene-2,16-dione
CAS: 981-15-7
Molecular Formula: C20H24O7
13,21-Didehydrochaparrinone - Names and Identifiers
13,21-Didehydrochaparrinone - Physico-chemical Properties
| Molecular Formula | C20H24O7 |
| Molar Mass | 376.4 |
| Density | 1.47 |
| Melting Point | 235-237 °C |
| Boling Point | 641.0±55.0 °C(Predicted) |
| Specific Rotation(α) | (c, 1 in EtOH)+24 |
| Flash Point | 231.6°C |
| Solubility | DMSO : 83.3 mg/mL (221.31 mM; Need warming) |
| Vapor Presure | 3.94E-19mmHg at 25°C |
| Appearance | White-like powder |
| pKa | 11.85±0.70(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.64 |
| In vitro study | Ailanthone is a potent inhibitor of both full-length AR (AR-FL) and constitutively active truncated AR splice variants (AR-Vs). Ailanthone binds to the co-chaperone protein p23 and prevents AR's interaction with HSP90, thus resulting in the disruption of the AR-chaperone complex followed by ubiquitin/proteasome-mediated degradation of AR as well as other p23 clients including AKT and Cdk4, and downregulates AR and its target genes in PCa cell lines and orthotopic animal tumours. In addition, Ailanthone blocks tumour growth and metastasis of CRPC. Ailanthone has been shown to possess an growth-inhibitory effect against several cancer cell lines including HepG2, Hep3B, R-HepG2, Jurkat, HeLa, MCF-7, MDA-MB-231 and A549 cells. Ailanthone inhibits Huh7 cell growth through the induction of mitochondrion-mediated cell apoptosis and G0/G1 cell cycle arrest. Ailanthone-induced apoptosis is mitochondrion-mediated and involved the PI3K/AKT signaling pathway in Huh7 cells. |
| In vivo study | Not only i.p. administration but also p.o. administration of Ailanthone has excellent efficiency for blocking the growth of CRPC xenografts. In pharmacokinetic studies, Ailanthone exhibits good solubility in water and good bioavailability (>20%). In addition, Ailanthone effectively suppresses CRPC tumour growth, despite not reaching a steady state of plasma drug concentration during the course of treatment. |
13,21-Didehydrochaparrinone - Reference Information
| plant extract | Ailanone is a plant extract, which is a substance extracted from the skin of Ailanthus altissima. It has antibacterial, antigenic and anti-tumor effects. 100% decoction has inhibitory effects on Shigella flexneri, Shigella soni and Escherichia coli in vitro. It has a strong inhibitory effect on amoeba and trichomonas vaginalis, and can inhibit the activities of other parasites. The decoction and tannin have astringent and hemostatic effects. Ailanone has cytotoxic activity on human nasopharyngeal carcinoma (KB) cells, and its ED50 is 10-2-10-3ug/ml. at a dose of 0.12-4.00 mg/kg, it shows certain activity on lymphocytic leukemia P388. The bark of Ailanthus altissima is the root bark or bark of the plant Ailanthus altissima. It is mainly produced in Shandong Province, Liaoning Province, Henan Province, Anhui Province and other places. Picking in spring and summer, removing the cork, slicing, drying, raw use, and fresh products. |
| preparation method | fresh bark or fresh root bark of Ailanthus altissima is taken, soaked in alkaline water with a volume of 5-10 times its mass and pH = 9-13 for 24-72 hours, filtered, the filtrate is adjusted to neutral with acid, concentrated, the concentrated solution is adsorbed through macroporous adsorption resin column, washed and removed impurities, elute with 60-85% ethanol, collect 3-8 times the volume of column eluent, recover the ethanol under reduced pressure to the end, refrigerate for 12-36 hours to decrystal, filter, take the filter residue, add acetone for recrystallization, wash and dry to obtain Ailanone. |
| biological activity | Ailanthone (AIL, Δ13-Dehydrochaparrinone) is a natural anti-liver cancer (HCC) component from Ailanthus altissima Ailanthus altissima, which can induce G0/G1 phase cell cycle arrest by reducing the expression of cyclins and CDKs and increasing the expression of p21 and p27. Ailanthone can trigger DNA damage, which is characterized by activation of ATM/ATR pathway. Ailanthone can induce mitochondria-mediated apoptosis involving PI3K/AKT signaling pathway in Huh7 cells. Ailanthone are also inhibitors of full-length Androgen Receptor (AR-FL) and constitutive active truncated AR splice variants (AR-Vs, AR1-651), corresponding IC50 values of 69 nM and 309 nM, respectively. |
| target | TargetValue CDK () AR-FL (cell-free assay) 69 nM AR 1-651 (cell-free assay) 309 nM |
| Target | Value |
| CDK () | |
| AR-FL (Cell-free assay) | 69 nM |
| AR 1-651 (Cell-free assay) | 309 nM |
| in vitro study | Ailanthone is a potent inhibitor of both full-length AR (AR-FL) and constitutively active truncated AR splice variants (AR-Vs). Ailanthone binds to the co-chaperone protein p23 and prevents AR's interaction with HSP90, this resulting in the disruption of the AR-chaperone complex followed by ubiquitin/proteasome-mediated degradation of AR as well as other p23 clients including AKT and Cdk4, and downregulates AR and its target genes in PCa cell lines and orthotopic animal tumours. In addition, Ailanthone blocks tumour growth and metastasis of CRPC. Ailanthone has been shown to possess an growth-inhibitory effect against several cancercell lines including HepG2, Hep3B, R-HepG2, jurkat, HeLa, MCF-7, MDA-MB-231 and A549 cells. Ailanthone inhibits Huh7 cell growth through the induction of mitochondrion-mediated cell apoptosis and G0/G1 cell cycle arrest. Ailanthone-induced apoptosis is mitochondrion-mediated and involved the PI3K/AKT signaling pathway in Huh7 cells. |
| in vivo research | not only I. p. administration but also p.o. administration of Ailanthone has excellent efficiency for blocking the growth of CRPC xenografts. in pharmacokinetic studies, Ailanthone exhibits good solubility in water and good bioavailability (>20%). in addition, Ailanthone effectively suppresses CRPC tumour growth, despite not reaching a steady state of plasma drug concentration during the course of treatment. |
Last Update：2024-04-09 20:49:11
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Product Name: Ailanthone Visit Supplier Webpage Request for quotationCAS: 981-15-7
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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