Eudesmin
(Synonyms: 桉脂素; (-)-Eudesmin; Eudesmine; (-)-Eudesmine) 目录号 : GC61941
Eudesmin ((-)-Eudesmin) 通过抑制 S6K1 信号通路来干扰成脂分化。Eudesmin 具有多种作用，包括抗肿瘤，抗炎和抗菌活性。
Cas No.:526-06-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Eudesmin ((-)-Eudesmin) impairs adipogenic differentiation via inhibition of S6K1 signaling pathway. Eudesmin possesses diverse therapeutic effects, including anti-tumor, anti-inflammatory, and anti-bacterial activities[1].
Treatment of mesenchymal stem cells (MSCs) with Eudesmin (20, 40, and 80µM) disturbs adipogenesis via suppression of S6K1 signaling pathway. Eudesmin treatment inhibits activation and nuclear translocation of S6K1. S6K1-mediated phosphorylation of H2B at serine 36 (H2BS36p) is reduced upon Eudesmin treatment[1].
References:
[1]. Ki Hong Nam, et al. Eudesmin Impairs Adipogenic Differentiation via Inhibition of S6K1 Signaling Pathway. Biochem Biophys Res Commun. 2018 Nov 10;505(4):1148-1153.
| Cas No. | 526-06-7 | SDF | |
| 别名 | 桉脂素; (-)-Eudesmin; Eudesmine; (-)-Eudesmine | ||
| Canonical SMILES | COC(C=C(C=C1)[C@@]2([H])[C@@]3([H])[C@](CO2)([H])[C@@](C(C=C4)=CC(OC)=C4OC)([H])OC3)=C1OC | ||
| 分子式 | C22H26O6 | 分子量 | 386.44 |
| 溶解度 | DMSO : 100 mg/mL (258.77 mM) | 储存条件 | 4°C, protect from light |
| 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 | 2.5877 mL | 12.9386 mL | 25.8772 mL |
| 5 mM | 0.5175 mL | 2.5877 mL | 5.1754 mL |
| 10 mM | 0.2588 mL | 1.2939 mL | 2.5877 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。
Eudesmin impairs adipogenic differentiation via inhibition of S6K1 signaling pathway
Biochem Biophys Res Commun 2018 Nov 10;505(4):1148-1153.PMID:30316515DOI:10.1016/j.bbrc.2018.09.188.
Eudesmin has been reported to possess diverse therapeutic effects, including anti-tumor, anti-inflammatory, and anti-bacterial activities. However, its molecular action has not been implicated in metabolic disease. In this study, we show that treatment of mesenchymal stem cells (MSCs) with Eudesmin disturbs adipogenesis via suppression of S6K1 signaling pathway. Eudesmin treatment inhibited activation and nuclear translocation of S6K1. Consequently, S6K1-mediated phosphorylation of H2B at serine 36 (H2BS36p) was reduced upon Eudesmin treatment, further inducing the expression of Wnt6, Wnt10a, and Wnt10b, which disturbed adipogenic differentiation. Moreover, Eudesmin promoted myogenic and osteogenic gene expression in MSCs. Taken together, we found a novel small molecule, Eudesmin, to block adipogenesis through down-regulation of S6K1-H2BS36p axis, followed by regulation of cell fate determination genes. This study suggests a promising therapeutic approach with Eudesmin to cure obesity and metabolic diseases.
Transcriptomics-Based Repositioning of Natural Compound, Eudesmin, as a PRC2 Modulator
Molecules 2021 Sep 18;26(18):5665.PMID:34577136DOI:10.3390/molecules26185665.
Extensive epigenetic remodeling occurs during the cell fate determination of stem cells. Previously, we discovered that Eudesmin regulates lineage commitment of mesenchymal stem cells through the inhibition of signaling molecules. However, the epigenetic modulations upon Eudesmin treatment in genomewide level have not been analyzed. Here, we present a transcriptome profiling data showing the enrichment in PRC2 target genes by Eudesmin treatment. Furthermore, gene ontology analysis showed that PRC2 target genes downregulated by Eudesmin are closely related to Wnt signaling and pluripotency. We selected DKK1 as an eudesmin-dependent potential top hub gene in the Wnt signaling and pluripotency. Through the ChIP-qPCR and RT-qPCR, we found that Eudesmin treatment increased the occupancy of PRC2 components, EZH2 and SUZ12, and H3K27me3 level on the promoter region of DKK1, downregulating its transcription level. According to the analysis of GEO profiles, DEGs by depletion of Oct4 showed an opposite pattern to DEGs by Eudesmin treatment. Indeed, the expression of pluripotency markers, Oct4, Sox2, and Nanog, was upregulated upon Eudesmin treatment. This finding demonstrates that pharmacological modulation of PRC2 dynamics by Eudesmin might control Wnt signaling and maintain pluripotency of stem cells.
Bromination of Eudesmin isolated from araucaria araucana induces epimerization and give bromine derivatives with loss of anti-Candida activity
Nat Prod Res 2022 Jun 16;1-6.PMID:35707900DOI:10.1080/14786419.2022.2089140.
Furofuran lignanes show important biological activities for the treatment of infectious diseases, inflammatory and metabolic pathologies. They have been isolated from leaves and barks of many plants. In Chile the native conifer Araucaria araucana produces Eudesmin, matairesinol, secoisolariciresinol and lariciresinol in stemwood, branchwood and knotwood. These compounds were previously isolated by laborious flash chromatography on silica gel. Here we report the easy isolation of Eudesmin by soxhlet extraction from milled knots of Araucaria araucana with hexane, followed by cryo-crystallization at -20 °C. Upon bromination of the isolated Eudesmin epimerization at one benzylic position occurs, giving epieudesmin and the corresponding mono and di-brominated derivatives. The structures were determined by 1D, 2D NMR and X-ray diffraction. The analysis of products against Candida yeast showed that Eudesmin has a moderate activity against different strains of Candida from 62.5 to 500 µg/mL. This activity decreases for epieudesmin, while bromine derivatives are not active.
Eudesmin exerts antitumor effects by down-regulating EZH2 expression in nasopharyngeal carcinoma cells
Chem Biol Interact 2019 Jul 1;307:51-57.PMID:31026422DOI:10.1016/j.cbi.2019.04.028.
Nasopharyngeal carcinoma (NPC) is a head and neck epithelial malignancy with high prevalence and represents a significant disease burden. Eudesmin is a natural lignin that has been reported to exhibit antitumor effect on lung cancer. However, the effect of Eudesmin on NPC has not been investigated. The aim of the present study was to evaluate the role of Eudesmin in NPC and to explore the underlying mechanism. The NPC cell lines CNE-1 and HONE-1 were treated with Eudesmin for 48 h. Cell viability was measured using MTT assay. Cell apoptosis was detected using flow cytometry. The expression levels of enhancer of zeste homolog 2 (EZH2), Akt, and p-Akt were measured using Western blot analysis. We found that Eudesmin inhibited cell viability and induced cell apoptosis of NPC cell lines in a dose-dependent manner. Eudesmin suppressed the expression of EZH2 and blocked the activation of Akt signaling pathway. Inhibition of Akt signaling pathway caused significant decrease in EZH2 expression. Moreover, knockdown of EZH2 attenuated the effects of Akt overexpression on cell viability and apoptosis in NPC cells. In conclusion, Eudesmin exhibited antitumor activity via downregulating EZH2 expression through the inhibition of Akt signaling pathway. Eudesmin could be developed as a new pharmacologic approach for NPC treatment.
Neuroprotective Properties of Eudesmin on a Cellular Model of Amyloid-β Peptide Toxicity
J Alzheimers Dis 2022 Nov 26.PMID:36463456DOI:10.3233/JAD-220935.
Background: Alzheimer's disease (AD) is a neurodegenerative disorder characterized by progressive cognitive impairment and memory loss. One of the hallmarks in AD is amyloid-β peptide (Aβ) accumulation, where the soluble oligomers of Aβ (AβOs) are the most toxic species, deteriorating the synaptic function, membrane integrity, and neuronal structures, which ultimately lead to apoptosis. Currently, there are no drugs to arrest AD progression, and current scientific efforts are focused on searching for novel leads to control this disease. Lignans are compounds extracted from conifers and have several medicinal properties. Eudesmin (Eu) is an extractable lignan from the wood of Araucaria araucana, a native tree from Chile. This metabolite has shown a range of biological properties, including the ability to control inflammation and antibacterial effects. Objective: In this study, the neuroprotective abilities of Eu on synaptic failure induced by AβOs were analyzed. Methods: Using neuronal models, PC12 cells, and in silico simulations we evaluated the neuroprotective effect of Eu (30 nM) against the toxicity induced by AβOs. Results: In primary cultures from mouse hippocampus, Eu preserved the synaptic structure against AβOs toxicity, maintaining stable levels of the presynaptic protein SV2 at the same concentration. Eu also averted synapsis failure from the AβOs toxicity by sustaining the frequencies of cytosolic Ca2+ transients. Finally, we found that Eu (30 nM) interacts with the Aβ aggregation process inducing a decrease in AβOs toxicity, suggesting an alternative mechanism to explain the neuroprotective activity of Eu. Conclusion: We believe that Eu represents a novel lead that reduces the Aβ toxicity, opening new research venues for lignans as neuroprotective agents.