(5Z)-7-Oxozeaenol
(5Z)-7-Oxozeaenol (CAS: 253863-19-3) is a naturally occurring resorcylic lactone obtained from fungal sources. It functions as a selective inhibitor of transforming growth factor β-activated kinase 1 (TAK-1), a member of the mitogen-activated protein kinase kinase kinase (MAPKKK) family. In biochemical assays, (5Z)-7-Oxozeaenol inhibits purified TAK-1 with an IC50 of approximately 8.1 nM, exhibiting minimal activity against related MAPKKKs. Cellular studies indicate irreversible blockade of IL-1-stimulated TAK-1, NF-κB, and JNK/p38 signaling pathways. This molecule is useful in inflammation research, as demonstrated by its suppression of IL-1-induced COX-2 production and attenuation of inflammatory responses in mouse models.
- 1. Yang Tang, Ying Wang, et al. "Shenbing Decoction III and Apigenin Improve Peritoneal Fibrosis Mediated by Epithelial–Mesenchymal Transition Through TAK1/p38MAPK/NF‐κB Pathways." Research ArticleFirst published: 28 February 2025
- 2. Liuling Luo, Huan Wang, et al. "Echinatin attenuates acute lung injury and inflammatory responses via TAK1-MAPK/NF-κB and Keap1-Nrf2-HO-1 signaling pathways in macrophages." PLoS One. 2024 May 16;19(5):e0303556. PMID: 38753858
- 3. Qifeng Deng, Sidi Yang, et al. "NLRP6 induces RIP1 kinase-dependent necroptosis via TAK1-mediated p38." iScience. 2024 Feb 28;27(4):109339 PMID: 38500819
- 4. Shunjie Xia, Lin Ji, et al. "TAK1 Is a Novel Target in Hepatocellular Carcinoma and Contributes to Sorafenib Resistance." Cell Mol Gastroenterol Hepatol. 2021;12(3):1121-1143. PMID:33962073
- 5. Saleh D, Degterev A. "Chemical Library Screens to Identify Pharmacological Modulators of Necroptosis." Methods Mol Biol. 2018;1857:19-33. PMID:30136227
| Physical Appearance | White solid |
| Storage | Desiccate at -20°C |
| M.Wt | 362.37 |
| Cas No. | 253863-19-3 |
| Formula | C19H22O7 |
| Solubility | <9.06mg/ml in DMSO;insoluble in ethanol |
| Chemical Name | (3S,5Z,8S,9S,11E)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,9,10-tetrahydro-1H-benzo[c][1]oxacyclotetradecine-1,7(8H)-dione |
| SDF | Download SDF |
| Canonical SMILES | O[C@@H](C/C=C/C(C=C1OC)=C(C(O)=C1)C(O[C@@H](C)C/C=C\C2=O)=O)[C@@H]2O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment:[1] | |
|
Cell lines |
Mouse embryonic fibroblast cells |
|
Reaction Conditions |
500 nM (5Z)-7-oxozeaenol for 17.5 h incubation |
|
Applications |
In cell culture, (5Z)-7-oxozeaenol blocked interleukin-1-induced activation of TAK1, JNK/p38 MAPK, IκB kinases, and NF-κB, resulting in inhibition of cyclooxgenase-2 production. |
| Animal experiment:[1] | |
|
Animal models |
Mice repeatedly sensitized by picryl chloride (PC) and subsequently challenged with PC |
|
Dosage form |
10 μl of (5Z)-7-oxozeaenol (1 mg/ml) Painted on each ear 2 h before and 4 h after the second PC challenge (total of twice) or every hour three times before and 4 h after the second PC challenge (total of four times) |
|
Applications |
When (5Z)-7-oxozeaenol was administrated to the PC-challenged ear, ear swelling was reduced by up to 50% of that of the control ear treated with vehicle. Thus, (5Z)-7-oxozeaenol was able to prevent inflammation by inhibiting the catalytic activity of TAK1 MAPKKK. |
|
Note |
The technical data provided above is for reference only. |
|
References: 1. Ninomiya-Tsuji J, Kajino T, Ono K, et al. A resorcylic acid lactone, 5Z-7-oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase. Journal of Biological Chemistry, 2003, 278(20): 18485-18490. |
|
Quality Control & MSDS
- View current batch:
-
Purity = 98.00%
- COA (Certificate Of Analysis)
- MSDS (Material Safety Data Sheet)
Chemical structure
Related Biological Data
