Loganetin
(Synonyms: 马钱苷元) 目录号 : GC32290
Loganetin是一种无毒的天然产物，可用于治疗耐多药革兰氏阴性菌感染的抗菌药物的开发。
Cas No.:29748-10-5
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
Loganetin is a non-toxic natural product that may be applied in the antibacterial drug development for treating multidrug-resistant Gram negative infections.
Although Loganetin does not possess antibacterial activity of its own, but in combination, it appreciably reduces the minimum inhibitory concentration (MIC) of nalidixic acid (NA) against nalidixic acid resistant (NAREC) and nalidixic acid sensitive (NASEC) strains of Escherichia coli. Loganetin, a very common, inexpensive, and non-toxic natural product may finds its application in the antibacterial drug development for treating multidrug-resistant Gram negative infections[1].
[1]. Anupam Maurya, et al. Preparative Isolation of Bioenhancer Loganetin from sf Alstonia scholaris by Fast Centrifugal Partition Chromatography. Separation Science and Technology Volume 49, 2014-Issue 5.
| Cas No. | 29748-10-5 | SDF | |
| 别名 | 马钱苷元 | ||
| Canonical SMILES | COC(C1=CO[C@@H](O)[C@@]2([H])[C@]1([H])C[C@H](O)[C@@H]2C)=O | ||
| 分子式 | C11H16O5 | 分子量 | 228.24 |
| 溶解度 | DMSO: 250 mg/mL (1095.34 mM) | 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 | 4.3814 mL | 21.9068 mL | 43.8135 mL |
| 5 mM | 0.8763 mL | 4.3814 mL | 8.7627 mL |
| 10 mM | 0.4381 mL | 2.1907 mL | 4.3814 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。
Loganetin and 5-fluorouracil synergistically inhibit the carcinogenesis of gastric cancer cells via down-regulation of the Wnt/尾-catenin pathway
J Cell Mol Med 2020 Dec;24(23):13715-13726.PMID:33098378DOI:10.1111/jcmm.15932.
Although most gastrointestinal tumours are sensitive to 5-fluorouracil (5FU), drug resistance is commonly occurred after 5FU therapy in gastric cancer (GC). Loganetin is the primary active compound in Cornus officinali. However, the synergetic effects of Loganetin and 5FU on GC remain unknown. Here, we investigated the synergetic effects and the underlying mechanism of Loganetin and 5FU on proliferation, stem-like properties, migration, and invasion of GC both in vitro and in vivo. We found that Loganetin alone inhibited the proliferation, stem-like properties, migration and invasion of GC cells in vitro. Importantly, the Loganetin remarkably enhanced the anti-cancer effect of 5FU on GC cells and the Wnt/尾-catenin pathway might be involved in this process. Animal experiments further confirmed the synergistic effects of 5FU and Loganetin on inhibiting cell growth and metastasis of GC. These results suggested that Loganetin could synergistically increase the effect of 5FU against GC, which sheds light on effective combinational drug strategies for GC treatment.
Loganetin protects against rhabdomyolysis-induced acute kidney injury by modulating the toll-like receptor 4 signalling pathway
Br J Pharmacol 2019 Apr;176(8):1106-1121.PMID:30706443DOI:10.1111/bph.14595.
Background and purpose: Acute kidney injury (AKI) is a rapid renal dysfunctional disease, for which no effective drugs or therapies are available to improve prognosis. Loganetin is a natural product with unknown bioactivities. Here, we identified a new protective effect and mechanism of Loganetin in a mouse model of AKI induced by rhabdomyolysis. Experimental approach: AKI was induced using glycerol by i.m. injection in mice models. Thirty minutes and 24 and 48 hr after injection of glycerol, the mice received 2 and 18 mg路kg-1 of Loganetin i.p. respectively. Then mice blood and kidney were collected for various biochemical and histopathological studies. Mechanistic studies on modulation of AKI by Loganetin were performed using HK-2 cells and Toll-like receptor 4 (TLR4) knockout mice. Key results: In the Loganetin treated group, kidney damage and mortality rate were declined, and blood urea nitrogen and serum creatinine were much lower. Loganetin prevented damage to the tubular structures induced by glycerol and decreased apoptotic cells at the corticomedullary junction. In HK-2 cells, Loganetin could inhibit NF-魏B pathway and pro-apoptotic genes expression. However, TLR4 was silenced by a specific shRNA, and the inhibitory effect of Loganetin in HK-2 cells vanished. Loganetin also down-regulated the expression of inflammation factors by suppressing TLR4 activity. Conclusion and implications: All the results suggested that TLR4 plays a critical role in AKI development, and Loganetin ameliorates AKI by inhibiting TLR4 activity and blocking the JNK/p38 pathway, which provides a new strategy for AKI treatment.
Gram-Scale Synthesis of Loganetin from S-(+)-Carvone
J Org Chem 2023 Apr 7.PMID:37026980DOI:10.1021/acs.joc.3c00253.
Loganetin is the aglycone moiety of loganin that has a 5,6-fused bicyclic framework and exhibits a wide range of interesting biological activities. A gram-scale synthesis of Loganetin has been accomplished from the readily accessible S-(+)-carvone. The key reactions of the synthesis are a Favorskii rearrangement to introduce four stereocenters and a sulfuric acid-meditated deprotection/cyclization reaction to assemble the sensitive dihydropyran ring with complete stereoselectivity. This work also enables us to synthesize C1 methoxy Loganetin and the enantiomer of Loganetin successfully.
seco-iridoids from Calycophyllum spruceanum (Rubiaceae)
Phytochemistry 2003 Sep;64(2):549-53.PMID:12943773DOI:10.1016/s0031-9422(03)00153-5.
Three seco-iridoids 7-methoxydiderroside, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids Loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochemistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosoma cruzi, with IC(50) values of 59.0, 90.2, 74,2 and 84.9 microg/mL, respectively and were compared to the standard gentian violet (IC(50) 7.5 microg/ml).
Inhibition of GSK_3尾 by Iridoid Glycosides of Snowberry ( Symphoricarpos albus) Effective in the Treatment of Alzheimer's Disease Using Computational Drug Design Methods
Front Chem 2021 Oct 7;9:709932.PMID:34692636DOI:10.3389/fchem.2021.709932.
The inhibition of glycogen synthase kinase-3尾 (GSK-3尾) activity prevents tau hyperphosphorylation and binds it to the microtubule network. Therefore, a GSK-3尾 inhibitor may be a recommended drug for Alzheimer's treatment. In silico methods are currently considered as one of the fastest and most cost-effective available alternatives for drug/design discovery in the field of treatment. In this study, computational drug design was conducted to introduce compounds that play an effective role in inhibiting the GSK-3尾 enzyme by molecular docking and molecular dynamics simulation. The iridoid glycosides of the common snowberry (Symphoricarpos albus), including loganin, secologanin, and Loganetin, are compounds that have an effect on improving memory and cognitive impairment and the results of which on Alzheimer's have been studied as well. In this study, in the molecular docking phase, loganin was considered a more potent inhibitor of this protein by establishing a hydrogen bond with the ATP-binding site of GSK-3尾 protein and the most negative binding energy to secologanin and Loganetin. Moreover, by molecular dynamics simulation of these ligands and GSK-3尾 protein, all structures were found to be stable during the simulation. In addition, the protein structure represented no change and remained stable by binding ligands to GSK-3尾 protein. Furthermore, loganin and Loganetin have higher binding free energy than secologanin; thus, these compounds could effectively bind to the active site of GSK-3尾 protein. Hence, loganin and Loganetin as iridoid glycosides can be effective in Alzheimer's prevention and treatment, and thus, further in vitro and in vivo studies can focus on these iridoid glycosides as an alternative treatment.