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20-Deoxyingenol Sale

(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

20-Deoxyingenol Chemical Structure

Cas No.:54706-99-9

规格 价格 库存 购买数量
10mM (in 1mL DMSO)
¥982.00
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5mg
¥893.00
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10mg
¥1,607.00
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产品描述

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)

Chemical Properties

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
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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
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Research Update

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.

[Constituents of Euphorbiaceae, 7. 20-Deoxyingenol Monoesters and ingenol diesters from Euphorbia biglandulosa Desf]

Arch Pharm (Weinheim) 1982 Dec;315(12):1026-32.7159190 10.1002/ardp.19823151209