20-Deoxyingenol
(Synonyms: 20-去氧巨大戟醇；20-去氧巨大戟萜醇) 目录号 : GC30011
A diterpenoid with antioxidant and osteoprotective activities
Cas No.:54706-99-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
20-Deoxyingenol is a diterpenoid that has been found in E. kansui and has antioxidant and osteoprotective activities.1,2 It inhibits oxidative stress-induced decreases in autophagic flux and apoptosis in isolated mouse chondrocytes when used at a concentration of 10 mM.2 20-Deoxyingenol (20 mg/kg per day, i.p.) reduces bone erosion and cartilage calcification in joints in a mouse model of injury-induced osteoarthritis.
1.Zhang, J.-S., Weng, H.-Z., Huang, J.-L., et al.Anti-inflammatory ingenane diterpenoids from the roots of Euphorbia kansuiPlanta Med.84(18)1334-1339(2018) 2.Gu, M., Jin, J., Ren, C., et al.20-Deoxyingenol alleviates osteoarthritis by activating TFEB in chondrocytesPharmacol. Res.165105361(2021)
| Cas No. | 54706-99-9 | SDF | |
| 别名 | 20-去氧巨大戟醇；20-去氧巨大戟萜醇 | ||
| Canonical SMILES | O=C1[C@@]2(C=C(C)[C@@H]3O)[C@]3(O)[C@H](O)C(C)=C[C@@]1([H])[C@@]4([H])[C@@](C4(C)C)([H])C[C@H]2C | ||
| 分子式 | C20H28O4 | 分子量 | 332.43 |
| 溶解度 | DMSO : 50 mg/mL (150.41 mM);Water : < 0.1 mg/mL (insoluble) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0082 mL | 15.0408 mL | 30.0815 mL |
| 5 mM | 0.6016 mL | 3.0082 mL | 6.0163 mL |
| 10 mM | 0.3008 mL | 1.5041 mL | 3.0082 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
20-Deoxyingenol alleviates osteoarthritis by activating TFEB in chondrocytes
Pharmacol Res 2021 Mar;165:105361.33460793 10.1016/j.phrs.2020.105361
Osteoarthritis (OA) is an age-related degenerative disease and currently cannot be cured. Transcription factor EB (TFEB) is one of the major transcriptional factors that regulates autophagy and lysosomal biogenesis. TFEB has been shown to be an effective therapeutic target for many diseases including OA. The current study explores the therapeutic effects of 20-Deoxyingenol (20-DOI) on OA as well as its working mechanism on TFEB regulation. The in vitro study showed that 20-DOI may suppress apoptosis and senescence induced by oxidative stress in chondrocytes; it may also promote the nuclear localization of TFEB in chondrocytes. Knock-down of TFEB compromised the effects of 20-DOI on apoptosis and senescence. The in vivo study demonstrated that 20-DOI may postpone the progression of OA in mouse destabilization of the medial meniscus (DMM) model; it may also suppress apoptosis and senescence and promote the nuclear localization of TFEB in chondrocytes in vivo. This work suggests that 20-Deoxyingenol may alleviate osteoarthritis by activating TFEB in chondrocytes, while 20-DOI may become a potential drug for OA therapy.
Total synthesis of ingenol
J Am Chem Soc 2004 Dec 22;126(50):16300-1.15600313 10.1021/ja044123l
A total synthesis of the biologically important diterpene ingenol has been completed. Ring-closing olefin metathesis was used to construct the strained "inside-outside" tetracyclic skeleton, and a series of diastereoselective reactions were employed to complete the synthesis. Another naturally occurring ingenane, 20-Deoxyingenol, has also been prepared.
Identification of Compounds Targeting Hepatitis B Virus Core Protein Dimerization through a Split Luciferase Complementation Assay
Antimicrob Agents Chemother 2018 Nov 26;62(12):e01302-18.30224531 PMC6256781
The capsid of the hepatitis B virus is an attractive antiviral target for developing therapies against chronic hepatitis B infection. Currently available core protein allosteric modulators (CpAMs) mainly affect one of the two major types of protein-protein interactions involved in the process of capsid assembly, namely, the interaction between the core dimers. Compounds targeting the interaction between two core monomers have not been rigorously screened due to the lack of screening models. We report here a cell-based assay in which the formation of core dimers is indicated by split luciferase complementation (SLC). Making use of this model, 2 compounds, Arbidol (umifenovir) and 20-Deoxyingenol, were identified from a library containing 672 compounds as core dimerization regulators. Arbidol and 20-Deoxyingenol inhibit the hepatitis B virus (HBV) DNA replication in vitro by decreasing and increasing the formation of core dimer and capsid, respectively. Our results provided a proof of concept for the cell model to be used to screen new agents targeting the step of core dimer and capsid formation.
Diterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of Xenopus (part 2)
Chem Pharm Bull (Tokyo) 2003 Aug;51(8):935-41.12913231 10.1248/cpb.51.935
Four new ingenane-type diterpenes, 3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoyl-20-O-acetylingenol (1), 3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoyl-20-deoxyingenol (2), 3-O-(2E,4Z-decadienoyl)-20-deoxyingenol (3), and 3-O-(2E,4E-decadienoyl)-20-deoxyingenol (4), two new jatrophane-type diterpenes, kansuinins D (9) and E (10), and four known ingenane-type diterpenes were isolated from the root of Euphorbia kansui. Their structures were elucidated by spectroscopic and chemical analysis, and individual Xenopus cells at the blastular stage were cultured with the diterpenes to test for biological activity. 20-Deoxyingenol diterpenes 3 and 4 induced the greatest cell cleavage arrest (0.5 micro g/ml of each compound resulted in >75% cleavage arrest), but cell cleavage inhibitory activity became weak when C-16 had an acyl residue. In contrast, the jatrophane diterpene kansuinin D (9) showed no activity.